Namenverzeichnis. Author Index

Kursiv gedruckte Seitenzahlen beziehen sich auf Literaturverzeichnisse

Page numbers printed in italies refer to References

Abdel-Kader, M. M. 148 Aota, K. 373 Abdurahman, N. 518 Applegate, H. E. 54 Abe, J. 53 Arakawa, H. 206 Abel, H. 462 Archer, R. A. 53 Abeles, R. H. 624,625,626,627 Ardenne,M.von 394,406,466 Abraham, E. P. 53 Arigoni, D. 458,469,624,628 Abrahamsson, S. 114 Arima, K. 117 Achilladelis, B. 109, 114 Aritomi, M. 187,189,206 Achini, R. 114 Armuth, V. 458 Acker, T. E. 274 Arndt, F. 274 Aczel, St. 216 Arndt, H. G. 210 Adams, M. H. 529,578 Arnold, N. H. 280 Adams, P. M. 114 Aron, E. 274 Adams, R. 219,280 Arroyo, E. R. 408, 448, 458, 466 Adamska, M. 184, 189,206 Arth, G. E. 60 Adinarayana 188 Asao, T. 148 Ager, I. 53 Asen, S. 187, 190 Aichner, F. X. 191,209 Ashbrook, C. W. 57 Alberty, R. A. 623 Asselin, A. 372 Alburn, H. E. 56 Atherton, D. R. 576 Alderweireldt, F. C. 458 Aurnhammer, G. 206,211, 214, 215 Aldrich, P. 518 Algar, J. 199,206 Babel, R. B. 56 Allan, J. 201, 206 Babior, B. M. 623,625 Allen, B. 579 Bader, F. E. 518 Allen, S. H. G. 627 Baeyer, A. 275 Allport, D. C. 274,575 Bagnara, J. D. 575 Alston, R. E. 177, 186,206,212,215 Bailar, J. C. 149 Amos 148 Baird, D. B. 570,575 Andersen, N. H. 283,287,293,304,328,346, Baird, R. 299,372 371, 372, 374 Baird, W. M. 455,458 Anderson, E. L. 518 Baker, P. M. 271,275 Ando, K. 117 Baldwin, J. E. 57 Ando, T. 212 Balenovic, K. 275 Andrews, S. I. 59 Balmain, A. 458 Ang, S. K. 518 Baltimore, B. G. 626 Aoki, Y. 211 Bamberg, P. 53 630 Namenverzeichni,. Author Index

Bamburg,1. R. 83, 112,114,148 Bhatia, V. K. 188, 189,206 Ban, Y. 473,518 Bhutani, S. P. 188,206 Barb, M. S. 187 Bickel, H. 55.60.518 Barbesgard, P. 277 Bied-Charreton, C. 629 Barczai-Beke, M. 473,518 Bielka, H. 461 Barczai-Martos, M. 191,206 Bieri, 1. G. 629 Barden, H. 575 Binns, F. 546, 547, 567, 570, 575 BargelJini, G. 195 Biol, M. C. 206 Barger, B. 188,206 Biollatz, M. 148 Barger, G. 148 Birch, A. J. 218,222,223,224,225,226,238, Barker, H. A. 622,623,626,627,628 244,246,250,252,275.372 Barrett, H. C. 314,372 Birkhofer, L. 175,206 Barton, D. H. R. 28,53 Birkinshaw,1. H. 148 Barton, J. E. D. 518 Birnbaum, G. I. 464 Bartosinski, B. 624 Birnbaum, J. 622 Bartsch, H. 458,459,462,463 Black, D. R. 151 Barz, W. 210 Blackley, R. L. 625.626,629 Bassett, C. 148 Bloch, B. 528,530,559,575 Bassett, R. N. 61 Bloch, K. 222,281 Batchelor, F. R. 53 Blois, M. S. 559, 563, 564, 575, 576. 582 Bates, R. B. 374 Blois, M. S. Jr. 575. 576 Battacharyya, S. C. 284,309,313,314,374,376 Blumental, G. 580 Battersby, A. R. 469 Bocian, G. E. 56 Batyuk, V. S. 206 Bodenstein, C. K. 275 Baxter, I. 570, 575 Boehm, R. 380,411,455,459 Bayse, G. S. 532,575 Bogmlr, R. 166, 193, 194, 207, 215. 216 Bear, C. A. 148 Böhme, E. H. W. 54 Beattie, T. R. 54 Böhner, B. 114,115.117 Beck, J. 518 Bollenback, G. N. 191,207 Beck, K. 210 Boltze, K.-H. 275 Beck, W. S. 626 Bonner, T. G. 576 Becker, F. 206 Boole, L. E. 380, 460 Becker, S. W. Jr. 529,577 Borchert, P. 416,418,420 Beckham, T. M. 623,628 Borer, C. 372 Bedford, C. T. 275 Borg, D. C. 565, 577. 582 Beer, R. J. S. 526, 542, 575 Borsche, W. 275 .Beerthuis, R. K. 149 Bose, A. K. 2, 58 Belanger, A. 374 Bouchez, M. P. 169,212 Bell, M. R. 53. 54 Bouchilloux, S. 527, 554,576,579 Benjamin, D. G. 207 Bouillant, M. L. 207.212 Bennet, G. B. 518 Bourquelot, E. 524 Bentley, R. 255,275 Boutard, B. 207 Benzing, E. 279 Boutwell, R. K. 455, 458. 459. 465 Berenblum, I. 379, 380, 384,457,458,459 Bowden, J. P. 64,115 Berger, F. 459 Bowness, J. M. 576 Bergmann, M. 208 Brachmann, I. 462 Bernhard, K. 459 Brackman, W. 576 Bernhauer, K. 624 Bradbeer, C. 625 Bertrand, G. 524 Brady, St. F. 283,374 Bertrand, J. A. 373 Brain, E. G. 54 Bethell, J. R. 244, 275 Bram, G. 229,232,252,275 Beton, J. L. 154,214 Brandl, F. 463 Beyersdorff. P. 2!O Brandt, K. G. 60 Namenverzeichnis. Author Index 631

Braunschweiger, H. 165,209 Carlson, 1. A. 53 Brechbühler, S. 148 Carnaghan, R. B. A. 151 Bredereck, H. 192, 193,209 Carnduff, J. 259,276 Brenneisen, P. E. 274 Carney, R. L. 278 Bresch, H. 458,459,462,463 Carter, L. 190 Brian, P. W. 64,115 Carty, D. J. 625 Bridger, R. F. 151 Casnati, G. 236,276 Bright, H. J. 576 Cathou, R. E. 629 Broadhurst, T. 526,542,575 Cava, M. P. 519 Brown, D. G. 625 Cederbaum, S. 627 Brown, H. W. 576 Chabannes, B. 207 Brown, K. S. 275 Chadenson, M. 207 Brown, L. D. 54 Chan, J. K. 279 Brown, R. T. 518 Chandler, B. V. 175,207 Brownson, C. 625, 626 Chaney, M. O. 58 Brück, D. 465 Chang, C. F. 214 Bruenger, F. W. 576 Chang, S. B. 148 Bruice, T. C. 276 Chapman, R. F. 547,570,575,576 Brunwin, D. M. 54 Chari, V. M. 215 Buchanan, J. M. 629 Chaumont, 1. P. 209 Buchanan, M. 148 Chauvelier, 1. 276 Buchheim, R. 427,459 Chauvette, R. R. 54,57 Büchi, G. 128, 134, 135, 136, 144, 148, 314, Chavin, W. 554, 576 372,491,502,510,513,519 Chen, Y. M. 554,576 Bucourt, R. 410,459 Cheney, L. C. 55,56,59 Budweg, W. 21J, 215 Cheng, F. C. 243,268,276 Bullock, E. 148 Cheng, J. C. 55 Bullot, J. 279 Cherbuliez, E. 380, 460 Bu'Lock, J. D. 274. 276. 526, 527, 540, Chernobrovaya, N. V. 206 541, 543, 545, 553, 566~ 575, 576, Cheung, K. K. 148 578 Chibber, S. S. 206 Bundgaard, H. 54 Chiurdog1u, G. 372 Bundy, G. 372 Chivers, B. R. 465 Burgstahler, A. W. 518 Chopin, J. 177, 179, 184, 189, 191, 197,204, Burkhardt, H. J. 148 205,206,207,212,214 Burnett, J. 580 Chow, A. W. 54 Busch, H. 462 Chow, J. H. S. 214 Bushnell, A. J. 214 Chow, W. Z. 372, 374 Butcher, B. T. 54 Christensen, B. G. 54,56,57 Butenandt, A. 377 Chumbalov, T. K. 187 Butler, T. C. 54 Ciegler, A. 149 Butler, W. H. 148 Cignarella, G. 54 Bycroft, B. W. 271, 275, 276 C1aes, P. 61 By1sma, F. 518,519 Claesen, M. 55 C1ark, D. E. 56 Caine, D. 340,372 Clark, J. M. Jr. 627 Caldwell, S. M. 61 C1arke, E. 460 Cama, L. D. 54 Clarke, H. T. 54 Cameron, D. W. 275 C1ayton, J. P. 54 CampelI, A. D. 151 C1emans, S. D. 54 Canter, F. W. 207 Clements, F. E. 115 Capon, B. 459 Clemo, G. R. 543,576 Carle, A. 181. 209 Coates, R. M. 372 632 Namenverzeichnis. Author Index

Cockle, S. A. 623 D'Arcy, A. D. 207 Codner, R. C. 280 Dave, K. D. 519 Coffen, D. L. 519 Davies, J. E. 149 Cole, R. J. 148 Davies, S. P. 623 Coleman, G. H. 193,212 Davis, W. W. 61 Collie, J. N. 218,219,220,221,222,230,244, Dawson, C. R. 533, 535, 536, 544,577 246,276 Dawson, J. B. 340,372 Colvin, E. W. 99,115 Dean, F. M. 244,277 Combs, C. S. Jr. 278 De Boer, Th. J. 416,465 Corner, F. 53 Decot, J. 372 Corner, F. W. 276, 280 De J~ng, K. 149 Commoner, B. 563,576 Dekker, E. E. 627 Conia, J. M. 304,372 Delaroff, V. 459 Connellan, J. 625 Delaveau, P. 213 Co oper, C. M. 53 Dellamonica, G. 197,207 Co oper, R. D. G. 53, 54, 55, 56, 58 Della Porta, G. 577, 578, 581 Corey, E. J. 372 De Marco, P. V. 53, 55, 58 Corey, H. S. 280 De Mayo, P. 373 Cornelius, H. 276 Demoie, E. 301,372 Cornforth,1. W. 115 Dennen, D. W. 55 Cornforth, R. H. 115 Deshapande, S. S. 277 Coronelli, C. 55 Deslongchamps, P. 331,372,374 Costa, G. 623 Detroy, R. W. 149 Costilow, R. N. 627 Deutsch, E. 622 Costin, C. R. 371 Dewdney, J. M. 60 Craig, L. C. 460, 465 De Weck, A. L. 60, 61 Crandall, T. G. 300,372 Dickens, F. 149 Crast, L. B. 56,59 Dickermann, H. W. 629 Crescenzi, S. 581 Dieckmann, H. 115 Cressman, W. A. 55 Diedrichs, H. H. 207 Cretney, W. J. 518 Dilworth, M. J. 629 Cromartie, R. 1. T. 526, 542, 577 Dingankar, Y. V. 277 Crombie, L. 243,255,269,276,277,404,435, DirscherI, R. 207,210,215 438,440,460,464 Dix, P. A. 282 Crowden, R. K. 187 Djerassi, C. 280,376,460 Crowfoot Hodgkin, D. 622 Dobson, R. L. 581 Crürös, Z. 216 Dobson, T. A. 276 Curd, F. H. 207 Dockner, T. 55 Curtis, P. J. 115 Doi, S. 116 Curtis, R. F. 148 Dolfini, J. E. 54,519 Curtis, R. W. 116 Dolinsky, M. 376 Dolphin, D. 623 Dadabo, K. 55,56 Doluisio, J. T. 55 Dadson, B. A. 519 Donkersloot, J. A. 149 Daehne, W. v. 55, 56, 458 Donnellan, B. 580 Daeniker, H. U. 519 Donnelly, Br. J. 211 Dahl, L. F. 60 Donovan, F. W. 222,275 Daicoviciu, C. 55 Dorp, D. A. van 149 Dane, E. 55 Dörr, F. 465 Danheiser, R. L. 375 Douglas, B. 518 Daniels, C. J. 56 Douglas, J. L. 234,275,277, 280 Danneel, R. 380, 460 Doudoroff, M. 281 Danninger, H. 214,215 Downing, M. H. 117 Namenverzeichnis. Author Index 633

Doyle, F. P. 53,55 Erfle, J. D. 627 Drake, N. L. 380, 460 Erge, D. 149 Dranik, L. 187 Eriksson, P. O. 277 Dreyer, D. L. 281 Esaki, S. 211 Drouet, J. 372 Eskins, M. 276 Drozd, G. A. 189 Essenberg, M. K. 624 Druckrey, H. 460 Essery, 1. M. 55, 56, 59 Ducep,J.-B.61,62 Evans, W. C. 577 Duchon, J. 529,577 Evans, W. H. 179,190,208 Dudley, K. H. 54 Evrard, E. 55 Dufour, J. 207 Ewing, J. B. 54 Du Jassonneix, C. B. 279 Ezekiel, A. D. 208 Duliere, W. L. 527, 577 Düll, P. 215 Falcone, M. S. 371, 372 Duncan, A. 576 Falkenhausen, F. v. 440,460 Dunham, D. J. 307,372 Farkas, 1. 207 Dunham, L. J. 149 Farkas, L. 153, 155, 165, 194, 198, 199,206, Dunlap, W. 212 208, 210, 212, 214, 215, 216 Dunstan, W. R. 380, 460 Farkas-Szabo,1. 207 Durbin, A. K. 55 Farney, R. F. 372 Durix, A. 207 Farnsworth, N. 215 Dürckheimer, W. 55 Faroog, M. O. 208 Dutton, M. F. 149 Fattorusso, E. 524, 535, 537, 544, 545, 548, Dutton, G. J. 207 557,558,561,580 Duxbury, F. K. 543,576 Faugeras, G. 208 Dyer, J. K. 627 Fechtig, B. 55 Feist, F. 219, 230, 277 Eade, R. 180, 189,206,207 Feldman, L. 214 Eagar, R. G. Jr. 626 Fellman, J. H. 533,535,577 Edelstein, L. M. 532, 580 Ferguson, G. 464 Edwards, G. S. 151 Ferrari, C. 61 Edwards, R. L. 277 Fetz, E. 114,115 Egger, K. 207, 209, 214 Fiedler, U. 189 Eggerer, H. 627 Finholt, P. 55 Egli, Chr. 518 Firestone, R. A. 56, 57 Eglington. A. J. 54 Fischer, E. 191,208 Ehninger, E. 460 Fisel, J. 189,208 Eisinger, A. 463 Fisher, J. 56 Eistert, B. 274 Fisher, J. W. 56 Ekström, B. 53,55,58 Fishman, J. 115 Elford, H. L. 629 Fitton, P. 275 EI Khadem, H. 155,207 Fitzpatrick, T. B. 529,575,577,579,582 EI-Kholy,1. E. 281 Flasch, H. 149 Ellert, H. G. 282 Fleischer, E. B. 623 Ellis, J. J. 149 Flaschenträger, B. 380, 398, 440, 441, 459, Eisworthy, G. C. 149 460 Emmelot, P. 459 Flesch, H. 216 Endo, K. 373 FIeseh, P. 531,572,577 Endres, W. 210 Fling, M. 578 Enggist, P. 372 Florkin, M. 581,582 Epstein, D. 580 Flury, E. 117 Erbing, B. 207 Flynn, E. H. 55,56,57 Erdtman, H. 373 Flynn, J. P. 199,206 634 Namenverzeichni,. Author Index

FoJlmann, H. 626 Gatenbeck, S. 226,277,281 F orgacs, J. 148 Gaucher, G. M. 277 Forrester, J. M. 109, 115 Gaudemer, A. 629 Forsyth, W. G. C. 533, 535, 577 Gazzard, D. 53 Fortner, J. G. 581 Gehrke, M. 191,209 Fosker, G. R. 56 Geissman, T. A. 155, 186,209,211,214 Foster, B. J. 56 Gentili, B. 164, 179, 180, 183, 189, 197, 209, Foster, G. H. 519 210 Foster, M. A. 623 Gerees, A. 162, 165, 191,216 Foulkes, D. M. 148 Geuther, A. 219,277 Fourie, L. 150 Geverz, A. 216 Fowlks, W. L. 579 Ghambler, R. K. 625,628 Fox, D. L. 577 Ghiara, G. 579 Fraenkel, G. H. 577 GiJl, J. E. 115 Franck, B. 149 Gillette, J. R. 545,578 Fraser, R. R. 56, 59 Gilman, J. C. 115 Frederiksen, E. 55 GirijavaJlabhan, M. 53 Freeman, G. G. 115 Girotra, N. N. 372 Frei, H. 277 Giuffa, E. 167,209 Frenk, E. 577 Gleason, F. K. 625 Freudenberg, K. 167,192,208 GIen, A. T. 115 Frey, A. J. 518 Gletsos, C. 518 Frey, P. A. 624 Gloggengiesser, F. 210 Friedman,.S. 629 Glombitza, K.-W. 56,59 Fries, E. M. 115 Glotzbach, B. 189 Fujii, T. 53 Glyzin, V. I. 188 Fujimoto, K. 53 Godfrey, J. C. 56,59,61 Fujinuma, Y. 580 Godtfredsen, W. O. 55,56,115,458 Fujioka, R. 374 Goetschel, C. 277 Fujise, S. 194, 208 Goldberg, M. W. 465 Fukui, S. 622,624,626 Goldblatt, L. A. 149, 150 Fukuko, K. 211 Golding, B. T. 623 Funaoka, K. 190, 208 Gomez-Revilla, A. 55 Funke, P. T. 54 Goodson, T. 60 Fürstenberger, G. 411,460 Gordon, J. J. 280 Furter, M. 465 Gordon, M. 528,577,579,582 Fürth 522 Gore, J. 372 Furuya, M. 208 Gore, T. S. 582 Gore, Y. 115 Gaffield, W. 165,208 Gorin, P. A. J. 162, 166,209 Galeffi, C. 209 Gorman, M. 56, 61 GaJlagher, R. T. 148 Gosteli, J. 60,62 Galle, K. 209 Gottlieb, O. R. 277, 280 Galston, A. 208 Gottstein, W. J. 55,56 Games, D. E. 276 Gougoutas, J. Z. 54 Games, M. L. 460,464 Gould, D. C. 623,625 Ganem, B. 375 Gould, St. J. 519 Ganguly, J. 282 Gould, R. F. 60 Gardiner, W. 626 Gourevitch, A. 59 Gardner, D. 83,115 Gouws, L. 150 Gardner, R. L. 188 Grady, F. J. 565,577 Gaskell, A. J. 519 Graffi, A. 461 Gassmann, J. 462,463 Graham, C. 372 Namenverzeichnis. Author Index 635

Grant, N. H. 56 Härri, E. 114, 116 Greenstein, J. P. 577 Harris, C. M. 217,242,247,277,278,279 Greig, D. G. T. 53 Harris, Th. M. 217,235,237,242,255,256, Grethe, G. 519 257,258,261,271,277,278,279,280,282 Griffiths, L. A. 578 Hartley, R. D. 149 Gröger, D. 149 Harwood, A. J. 56 Gross, A. J. 532,578 Hasan, S. K. 61 Gross, H. 207 Hassall, C. H. 148 Grouiller, A. 167, 207, 209, 213 Hassaniali-Walji, A. 276 Grove, J. F. 115 Hatanake, H. 213 Gschwendt, M. 458,461,462,465,466 Hatfield, L. D. 55,56 Guddal, E. 56 Hatsuda, Y. 149,151 Guest, J. R. 629 Hattori, S. 198, 209, 214 Guilford, H. 277, 281 Hauser, C. R. 234, 277, 278, 279, 280, 282 Gundersen, E. 55 Hauser, D. 57,117 Gupta, S. R. 206,208, 209 Hauteville, M. 207 Gumiak, R. 208 Havinga, E. 576 Gutersohn, J. 61 Haworth, R. D. 538, 564, 578 Gutowski, G. E. 56 Hay, J. V. 271,278 Gutzwiller, J. 115,116,117,519 Hayaishi, O. 578,582 Gwynn, R. H. 380, 461 Hayashi, K. 190 Hayes, H. B. 54 Hadfield, J. R. 518 Haynes, L. J. 177,209 Hadley, M. E. 575 Hayon, E. 625 Hague, D. N. 623 Hayton, W. L. 60 Haie, W. J. 277 Heacock, R. A. 578 Hall, N. M. 54 Heathcote, J. G. 149 Halliwell, G. 116 Hecker, E. 377, 390, 408, 411, 413, 415, 416, Hallstrand, A. 55 418,419,420,421,422,427,440,441,447, Halpem, J. 623 448,449,454,456,458,459,460,461,462, Hama, M. 211 463,464,465,466 Hamada, G. 580 Hedgecock, P. F. 278 Hamasaki, T. 149,151 Heidenbluth, K. 275 Hameed, N. 212 Heise, D. 209 Hamilton, J. A. 625,626 Helferich, B. 192, 193,209 Hamilton-Miller, J. M. T. 56,60 Hem, S. L. 58 Hammady, I. M. M. 148 Hemming, H. G. 115 Hampton, K. G. 277 Hemming, R. 209 Hannig, M. 59 Hempel, K. 558,559,574,578,580 Hänsei, R. 190,209, 210 Henderson, R. G. S. 624 Hanson, J. R. 114 Henery-Logan, K. R. 151 Hansson, Y. 277 Henseleit, E. 460 Harbome, J. B. 151,155,170,171,175,187, Herbst, M. M. 626 188,189,190,191,209,210,282 Hermodsson, S. 277 Hardcastle, G. A. Jr. 56,57 Herout, V. 285,291,317,321,328,375,376 Hardegger, E. 165,209 Herrisset, A. 209 Hardy, K. D. 56 Herz, W. 463 Harispe, M. 373 Hesse, M. 469,519 Härle, E. 458,461,462,463 Hesse, O. 279 Harley-Mason, 1. 494, 503, 507, 509, 512, Hesseltine, C. W. 149 518, 519, 526, 540, 541, 542, 543, 545, Hessler, E. J. 582 553,570,576,577,578 Heusler, K. 2,55,57,60,62 Harper, K. A. 175,207 Hewitt, G. 53 636 Namenverzeichnis. Author Index

Hikino, H. 373, 376 Hsieh, D. P. H. 149 Hili, H. A. O. 623,628 Hu, F. 575,577,579,580,581 Hill, J. S. 372 Huber, F. M. 57 Hillis, W. E. 179,181,189,209,210,226,278 Hübner, K. 279 Hindley, K. B. 217,282 Huckin, S. N. 279 Hirai, S. 519 Hudson, C. S. 211 Hirata, Y. 282 Huennekens, F. M. 626,629 Hirose, Y. 304, 374, 375 Huff, G. L. 54 Hirshon, J. M. 577 Huffman, J. W. 373 Hisatsune, K. 279 Huffman, G. W. 54 Hitzier, G. 210,215 Hulyalkar, R. K. 211 Ho, P. P. K. 57 Hünig, S. 279 Ho, R. K. Y. 628 Hunger, A. 519 Hochstetler, A. R. 371,373 Hüper, F. 149 Hodges, R. 148 Hoffman, M. Z. 625 Ibrahim 189 Hogeboom, G. H. 529,578 !ce, C. H. 200,211 Hogenkamp, H. P. C. 623,624,625,626.629 Iguchi, S. 279 Holcomb, J. 408,448, 458 Ilyas, M. 212 Holdrege, C. T. 56,59,61 Imashiro, Y. 59 Holker, J. S. E. '149, 150 Immich, H. 462 Holland, H. L. 623 Indelicato, J. M. 57 Holland, R. J. 622, 623, 624, 627 Ingraham, L. L. 576,622,627 Holldorf, A. W. 461 Ingram, D. J. E. 579 Holmquist, B. 276 Ingwa1son 340 Holmwood, G. M. 150 Inouye, H. 211 Holzapfel, C. W. 150 Iodice, A. A. 626 Holzer, H. 461 Iongh, H. de 150 Honty, K. 518 Irie, T. 374 Hoover, J. R. E. 54,57 Isaka, I. 57, 58 Hoppe, W. 462,463 Isemura, Y. 624 Hopper, M. W. 62 Ishida, M. 151 Horak, V. 545,578 Ishihara, S. 62 Horeau, A. 116,373 Ishikawa, K. 577 Hörhammer, L. 174, 179, 180, 189, 190,206, Ishikura, N. 278 207,208,210,211,212,214,215,462 Ishitani, H. 626 Hori, Y. 578 Islam, K. M. 464 Hörmann, O. 212 Isono, T. 375 Horn, D. H. S. 179,181,210 !toh, M. 116 Horn, G. 578 Iyengar, M. A. 215 Horn, U. 623 Horner, L. 578 Jackman, L. M. 150 Horowitz, N. H. 578 Jackson, A. 519 Horowitz, R. H. 164, 179, 180, 183, 189, Jackson, B. G. 57,59 190,197,209,210 Jackson, J. R. 57 Hösel, W. 210 Jacobi, P. 415, 418, 419, 448, 449, 461, 462, Hostalek, Z. 151 463,466 Hotta, Y. 53 Jacobs, S. 623 Hourfar, A. 213 Jacobsen, D. W. 626 Howard, J. 59 Jacobson, M. 463 Howarth, T. T. 255,278,279 Jacques, J. 290,373 Hozumi, T. 244, 279 Jacquesy, J. C. 463 Hsia, Y. E. 627 Jacquesy, R. 463 Namenverzeichnis. Author Index 637

Jadassohn, J. 575 Kaiser, G. V. 3, 57 Jaenicke, L. 629 Kaiser, R. 302, 350,373,374 Jain, A. C. 211 Kalaus, G. 513 Jain, T. C. 374 Kallmann, R. F. 576 James, A. W. G. 255, 277 Kamen, M. D. 628 Jansen, A. B. A. 57 Kamiya, S. 165, 191, 192, 196,211 Jarboe, C. H. 282 Kaneko, Y. 116 Jarczyk, H. 462 Kannengiesser, G. 61,62 Jasching, W. 463 Kao,J. 464 Jayme, M. 625 Kaplan, M. 519 Jenrette, W. V. 577 Karoglan, J. E. 376 Jensen, E. R. 280 Karrer, P. 463 Jensen, L. H. 281 Karrer, W. 155,211 Jentsch, J. 373 Karsten, U. 175,211 Jentzsch, K. 188 Kashiwagi, T. 57, 58 Jerdan, D. S. 279 Kastenmeier, P. 59 Jerzmanowska, Z. I. 194,211 Kato, K. 282 Joachim, U. H. 280 Kato, T. 244,279 Jobst, J. 279 Katritzky, A. R. 578 Jolfe, A. Z. 150 Katsube, Y. 151 Johnson, A. P. 373 Katz, T. J. 518 Johnson, A. W. 276,623,624 Kauffmann, T. 380, 408, 440, 463 Johnson, B. C. 627 Kawahara, N. 57 Johnson, D. 54,282 Kawahara, S. 57, 58 Johnson, D. A. 56, 57 Kawano, N. 213 Johnson, D. K. 211 Kawamura, T. 575 Johnson, F. 373 Kawase, A. 180, 190,211 Johnson, G. 211 Kawata, K. 519 Johnson, J. R. 54 Keil, M. 207, 214 Johnson, L. F. 53 Kekule, A. 464 Johnson, P. C. 374 Kellermeyer, R. W. 627 Johnson, S. 280 Keller-Schierlein, W. 116 Johnson, S. M. 372 Kennedy, F. S. 628 lohnston, D. B. R. 56, 57 Kertesz, D. 531,544,576,578 Joly, G. 463 Kerwar, S. S. 629 JomB, J. 376 Keuning, R. 149 Jones, E. R. H. 115,116 Kezdy, F. J. 281 Jones, H. E. H. 149 Khokhlov, A. S. 58 Jones, J. K. N. 211 Kiarmuddin, M. 208 Jones, N. D. 55,58 Kierstead, R. W. 518 Jose, F. L. 54, 55, 56 Kimura, T. 318,325,376 Joshi, B. S. 582 King, H. G. C. 185,211 Joule, J. A. 489, 519 King, J. A. G. 550, 551, 567, 575, 578 Julia, M. 279 King, T. J. 276 Julian, E. A. 191,211 King, T. P. 460 Junek, H. 282 Kinget, R. D. 57 Jurd, L. 190, 200, 208, 211 Kinney, R. E. 151 Jürgensen, G. 55 Kinosita, R. 150 Kinzel, V. 466 Kagal, S. A. 149 Kirby, F. B. 279 Kagan, H. B. 116 Kirby, G. W. 551,578 Kagan, J. 213 Kirkaldy, D. 148,149 Kaiser, C. 206 Kirkpatrick, J. C. 518 638 Namenverzeichnis. Author Index

Kirksey, 1. W. 148 Kung, H. F. 627 Kis,Z. 116 Kunz,F.628 Kishaba, A. N. 116 Kurabayashi, M. 374 Kitagawa, I. 370,373 Kuratomi, K. 628 Klein, E. 460 Kurono, M. 148 Klein, W. 193,209 Kurosawa, E. 375 Kleiner, E. M. 58 Kutney,J. P. 502,505,509,518,519,520 Klyne, W. 460 Kuwano, D. 373 Knauber, H. 208 Kuwano, H. 62 Knight, J. A. 150 Kuyama, S. 149 Knight, M. H. 276 Knorr, E. 193, 194, 195, 198, 199, 201, 203, Ladd, J. N. 622,623 204,211 Lafontaine, J. 374 Koch, W. 461 Lakshmikantham, M. V. 463 Kocor, M. 116 Lammert, S. R. 58 Kocsis, K. 519 Lancini, G. C. 55 Koda, A. 57, 58 Langseth, L. 466 Kodja, A. 527, 554, 576, 579 Lansbury, B. T. 373 Koe,B. K. 58 Lanzi, G. 581 Koeppen, B. H. 179, 188, 192, 193,211 Larkin, J. 276 Koesnikov, D. G. 206 Larrabee, A. R. 629 Kögl, F. 279 Lavagnino, E. R. 59 Kohnle, J. 622 Law, P. Y. 625 Koide, T. 53 Lawton, R. G. 300, 307,372 Komae, H. 374 Laxer, G. 579 Komatsu, M. 180, 189,211 Leanza, W. J. 54 Komninos, T. 246,279 Lebreton, F. 169,212 Kompis, I. 469,519 Lebreton, P. 207 Kondo, M. 624 Lee, H. A. Jr. 624 Königs, W. 193,194,195,198,199,201,203, Lee, H. L. 519 204,2lJ Lee, L. P. 623 Kopil, D. N. 277 Lee, W. S. 61,62 Koppel, G. A. 57 Leeh, W. 210 Körösy, F. 191, 206 Lefeuvre, A. 279 Korth, T. 519,520 Legator, M. S. 150 Kosmol, H. 206 Legrand, M. 459 Kovacs, O. K. J. 58 Lehnartz, E. 460 Krämer, H. 208,210 Leiba 188 Kranen-Fiedler, U. 212 Leigh, T. 58 Kratel, G. 629 Lemmon, R. M. 576 Kreibich, G. 413, 458, 459, 462, 463, 464, Lendle, L. 380, 459 465,466 Lenhardt, K. 463 Kretney, W. J. 520 Lenhert, P. G. 622 Kriesmair, G. 210 Lentz, K. 628 Kristiansen, H. 55 Le Quesne, P. 518,520 Kropp, P. J. 373 Lerner, A. B. 529, 577, 579 Kroschewsky, J. R. 188,212 Lettre, H. 461,464,465,466 Kubinyi, H. 427, 458, 459, 462, 463 Levi, L., 374 Kuchinskas, E. J. 58 Levine, B. B. 58 Kukita, A. 579 Levy, G. N. 58 Kukolja, S. 3, 42, 58 Levy, H. L. 627 Kulsa, P. 519 Lewak 189 Kumai, S. 214 Lewin, L. 464 Namenverzeichnis. Author Index 639

Lewis, Y. S. 189 Maheshwari, M. L. 374,376 Lewis, R. G. 519 Maitland, P. 244,275 Li, J. P. C. 580 Major, A. 208 Licari, T. 623 Maksyutina, N. P. 166,212 Liebermann, C. 212 Malhotra, A. 212 Lien, E. L. 625 Maling, 1. E. 576 Light, R. J. 278,279 Mangum, J. H. 629 Lijinsky, W. 380,464 Manhas, M. S. 2, 58 Lillehoj, E. B. 149 Mania, D. 57 Lilljequist, A. C. 627 Manske, R. H. F. 520 Lindberg, B. 207 Marcus, E. 236,279,281 Lindbiom, R. O. 576 Marhall, T. B. 212 Lindquist, 1. A. 207 Markey, F. X. 376 Lindsay, R. E. 58 Markham, K. R. 173, 187,212 Link, S. 373 Marsden, C. D. 579 Linstead, R. P. 410,464 Marsh, C. A. 212 Lipmann, F. 281 MarshalI, A. C. 60 Lissitzky, S. 576 MarshalI, J. A. 283,374 Litvinenko, V. I. 166,190,212 Martin, E. 575 Ljungdahl, L. 628 Marxer, A. 380, 466 Lo, Y. S. 58 Masaiti, Y. 188 Loeffier, W. 116 Masamune, S. 374,496 Lonay, V. 459 Mason,H.S.526,527,533,537,540,543,545, Long, A. A. W. 58 549, 552, 553, 564, 570, 579, 580. 581. 582 Long, J. W. 207 Mason, J. H. 519 Longridge, J. L. 58 Massart, L. 582 Longuet-Higgins, H. C. 579 Massy-Westropp, R. A. 275 Looker, B. E. 53 Mateles, R. I. 149 Looney, F. D. 626 Mathew, C. T. 372 Loughlin, R. E. 629 Mathieu, G. 466 Lowe, G. 54, 115, 116 Matous, B. 577 Lowe, J. N. 627 Matsumoto, K. E. 519 Lozano, D. 213 Matsumoto, N. 61 Lucente, G. 53 Matsuo, T. 61 Ludwig, B. J. 536,577 Mauli, R. 115,117 Lukiewicz, S. 579 McBride, B. C. 628 Lund, F. 55,58 McCarry, B. E. 275 Lund, N. A. 538,579 McCloskey, Ch. M. 193,212 Lundin, R. E. 151 McClure, J. W. 186, 190,212 Lustig, E. 151 McClure, R. J. 373 Lutomski, J. 184,206 McCormick, J. R. D. 274,280 Lynen, F. 279,627 McCurry, P. M. Jr. 333, 334, 364, 373 McDonald, D. 206 Mabry, T. J. 184, 186, 189, 207, 212, 213, McDougall, B. M. 629 214,215 McEachan, C. E. 290,373 Machida, Y. 116 McGookin, A. 208 Macierewicz, Z. 279 McGovern, V. J. 579,581 Mac1eod, W. D. Jr. 373 McGowan, J. G. 64,115 MacMillan, J. 116 McGregor, D. N. I Macsweeny, D. F. 373 McKague, B. 520 Magalhaes, M. T. 280 McKeown, J. M. 149 Magno, S. 524, 535, 537, 545, 548, 557, 580 McMillan, I. 59 Mahesh, U. B. 212 McPhail, A. T. 116,373 640 Namenverzeichnis. Author Index

Mea,D.373 Morin, R. B. 26,58, 59, 60 Melchert, T. E. 187 Morita, N. 212 Meiera, A. 458 Morley, C. G. D. 627 Mellor, J. M. 374 Morrison, M. 532, 575 Mentzer, C. 214, 277, 279 Morrlson, R. I. 115 Mervyn, L. 624 Mors, W. B. 277,280 Merwe, K. J. van der 150 Mortimer, P. H. 115 Mester, L. 216 Morton, R. A. 576 Mestichelli, L. 623 Mosbach, K. 277 Mestroni, E. 623 Moser, G. H. 179,205,215 Mestroni, G. 623 Moss, T. H. 623,625 Metzsch, F. A. von 466 Mossman, B. T. 465 Meyer, G. A. 282 Motl, O. 372, 374 Meyer, J. G. 462,464 Mottram, J. C. 379, 464 Meyer, U. 114 Moye, C. J. 275 Meyer-Bertenrath, J. G. 380, 388, 392,426, Mrugasiewicz, K. 189 464 Mudd, S. H. 627 Micetich, R. G. 59 Mucheirn, L. J. 149, 150 Michaely, W. J. 624 Mueller, R. A. 59 Michalska, M. J. 211 Muggleton, P. W. 624 Miles, M. L. 280 Mühlbock, O. 459,577,578,581 Miller, G. A. 280 Mühlemann, H. 244, 280 Miller, J. A. 276 Müller, B. 114 Miller, P. A. 280 Müller, G. 622 Miller, T. L. 582 Müller, O. 622,624 Miller, W. W. 627 Munavalli, S. 374 Milne, G. 148 Munk,R.275 Minamida, I. 59 Murakami, M. 57,58 Minato, H. 292, 374 Murakami, T. 212 Minor, W. F. 56, 59 Murphy, G. P. 261,278, 279, 280 Mirrington, R. N. 463 Murray, T. P. 235,280 Misco, P. F. 56 Murti, V. V. S. 212 Mishima, H. 374 Musgrave, O. C. 275 Mishra, S. N. 567,575 Myers, W. S. 246, 276 Misra, R. 62 Misuraca, G. 579,581 Naegeli, P. 62, 302, 350, 373, 374 MitchelI, G. F. 148 Näf,F.519 Mitt, T. 519 Nagahori, H. 374 Mitui, S. 208 Nagata, W. 519 Miyamoto, M. 61, 577 Nair, A. G. R. 215 Miyawaki, T. 61 Nairn, P. M. 580 Miyazaki, T. 213 Nakahara, W. 464 Mizelle, J. 212 Nakano, K. 57 Mohamed, Y. S. 155,207 Nakaoki, T. 189,212 Moll, F. 59 Nakatsuka, N. 518 Mollberg, R. 55 Nakatsuka, T. 375 Monache, E. M. delle 209 Nakayama, E. 62 Money, T. 109,115,234,238,253,259,261, Nakazaki, M. 206 275,276,277,280 Narasimhachari, N. 212 Mongrain. M. 372.374 Naves. Y. R. 374 Montagna, W. 575,577,579,580,581 Nayler, J. H. C. 53, 54, 55, 56, 58, 59 Montgomery, H. 529,577 Nelson, R. M. 580 M,rch, P. 55,56 Nesbitt, B. F. 149,150 Namenverzeichnis. Author Index 641

Nespiak, A. 64,116 Olechnowicz-Stepien, V. 212 Neubert, M. E. 56, 59 Oliver, L. K. 520 Neumann, H. 463 Ollis, W. D. 209,280,519 Neville, G. A. 374 Omote, Y. 580 Newman, G. E. 627 Oppolzer, W. 62 Newberne, P. M. 151 Or, N. 580 Nicolaus, R. A. 522,523,535,537,544,545, Ord, W. O. 149 548,555,557,558,561,570,579,580,581 Orris, L. 466 Niebergall, P. J. 55, 56 Ostermayer, J. 210 Niemann, G. J. 187 O'Sullivan, W. I. 280 Nieschlag, H. 210 Overath, P. 627 Nigam, I. C. 374 Overend, W. G. 208 Nilsson, B. 114 Overman, L. E. 370, 376 Nilsson, E. 187 Oxley, P. 464 Nishiie, K. 53 Oyamada, T. 199,213 Nishikawa, Y. 212 Nishimura, H. 519 Paal, C. 420, 464 Nixon, P. F. 625 Paal, Z. 208 N6gnldi, M. 199,208, 210, 212, 214, 215 Pacheco, H. 198,207,209,213 Nölken, E. 282 Paech, K. 582 Nomine, G. 466 Pailes, W. H. 629 Nonhebel, D. C. 276 Pake, G. E. 563, 576 Nordgren, L. 580 Paknikar, S. K. 374 Norin, T. 373,460 Pallanza, R. 55 Norpoth, K. 116 Pallenbach, D. 56,59 Norris, G. L. F. 115 Pallos, L. 198,208,214 Novak, L. 59 Panetta, C. A. 56, 57 Nozoe, S. 116 Paris, R. R. 180, 187, 188, 189,208,209,213 Numasaki, Y. 57 Parker, D. J. 628 Numata, M. 59 Parker, W. 374 Parry, D. R. 148 O'Brien, D. H. 465 Partyka, A. 59 O'Brien, J. R. 627 Paschal, J. W. 58 Ocken, P. R. 464 Patel, R. P. 580 Oekedon, D. J. 188 Pathak, M. A. 577 Oelrichs, P. J. 190,212 Paukstelis, J. V. 464 Oesterlin, R. 53, 54 Paul, D. 463,464 Oettle, A. G. 150 Paul, I. C. 372 Ogasawara, K. 519 Pawelkiewicz, J. 624 Ogiso, A. 176,213,374 Pearson, M. J. 54, 59 Ogunkoya, L. 551,578 Pearson, R. G. 623 Ohloff, G. 460 Pechan,Z.529,577 Ohmori, H. 626 Pechmann, H. v. 276 Ohnsorge, U. 149 Pelt, J. G. van 150 Ohta, N. 213 Penfold, A. R. 374 Ohta, T. 213 Pennington, P. A. 54 Ohta, Y. 304,371,374 Percheron,F.214 Ohumura, T. 519 Percival, A. 550,551,567,575,576,578,580 Oishi, T. 518 Pereira, S. 213 O'Kelly, J. 149,150,151 Perkin, A. G. 179 Okigawa, M. 213 Perlin, A. S. 162, 166,209 Okuchi, M. 116 Perlman, I. D. 57 Okun, M. R. 532, 580 Perron, Y. G. 59,61

Fortschritte d. ehern. org. Naturst. XXXI 41 642 Namenverzeichnis. Author Index

Perrottet, E. 374 Quirin, M. 213 Perry, M. B. 211 Qureshi, I. H. 280 Petcher, T. J. 116 Peter, H. 60 Raap,R.59 Peterkofsky, A. 624 Rabate, J. 166, 168,213 Petersen, H. J. 55 Rabe, A. 208 Peterson, D. C. 579 Radecka, C. 374 Peterson, E. 579 Radunz, H. E. 519,520 Peterson, E. W. 553, 570, 582 Rahman, W. 208,212 Petri, E. 464 Raick, A. N. 465 Pettersen, R. C. 464 Ramage, R. 62,373,374 Pfäffii, P. 116 Ramsay, B. G. 54, 59 Pferdeman, A. F. 151 Ranganathan, S. 62 Pfau, A. SI. 316,321,322,375 Rance, M. J. 150 Piatelli, M. 524, 535, 537, 545, 548, 555, 557, RandalI, W. C. 623 558,561,580 Rao, P. S. 190 Piers, E. 341,375,518,520 Raper, H. S. 524, 525, 526, 527, 528, 540, Pifferi, G. 54 543, 545, 552,57~581 Pike, D. G. 280,281 Raphael, R. A. 115 Pike, M. T. 374 Rasmusson, G. H. 60 Pizzolato, G. 519 Rassweiler, C. F. 219,280 Placeway, C. 520 Rauen, H. M. 116 Plattner, P. A. 316,322,375 Ravindranath, B. 209 Pliva, J. 375 Redfield, B. G. 629 Plouvier, V. 180,188,213 Reese, C. 519 Pointer, D. J. 460,464 Refojo, F. 213 Pollak, J. 280 Reichei, L. 213 Pomerantz, S. H. 580 Reichert, E. 279 Pons, W. A. Jr. 150 Reichwald, W. 213 Popjak, G. 115 Reiner, R. 60 Porter, L. J. 212 Reininger, W. 281 Post, O. 465 Reiser, A. 375 Postescu, D. 55 Renbutsu, M. 149 Poston, J. M. 628 Rendina, M. C. 209 Praill, P. F. G. 278,280 Resplandy, A. 281 Prasad, K. N. 582 Retey, J. 624,628 Pratt, J. M. 624,628 Reusch, W. 376 Preobrazhenskii, N. A. 195,213,214 Reyno1ds, G. F. 60 Preston, N. C. 116 Renz, P. 628 Price, K. E. 2, 3, 59 Ribas, J. 213 Pridham, J. B. 155,213 Ricca, A. 276 Prota, G. 571, 579, 580, 581 Richards, J. H. 625,626,627 Prox, A. 213 Rickards, R. W. 275 Pryor, M. G. M. 581 Ridsdale, S. 628 Puar, M. S. 54 Riesner, H. 520 Pugh, C. E. M. 581 Riley, V. 575,576,578,579,580,581,582 Pullman, A. 581 Rittenberg, D. 222,281 Pullman, B. 581 Roberts, E. C. 148 Purchase, I. F. H. 150,151 Roberts, J. B. 577 Pushkas, 1. 59 Roberts, J. C. 119,148,149,150,276 Roberts, J. S. 115,374 Quesnel, V. C. 533, 535, 577 Robertson, A. 207, 208, 526, 538, 542, 575, Quilico, A. 276, 538, 581 579 Namenverzeichnis. Author Index 643

Robertson, A. M. 628 Salasoo, A. I. 207 Robinson 343 Salemink, C. A. 279 Robinson, J. B. 149 Sallay, S. J. 517,520 Robinson, O. P. W. 61 Sammes, P. G. 53 Robinson, R. 54, 201, 206, 221, 222, 281 Samokhvalov, G. T. 200,213 Robinson, W. G. 626 Sargeant, K. 150,151 Robson, N. C. 547, 550, 551, 567, 570, 575, Sarkar, S. K. 518 578,581 Sarkisian, G. M. 369,376 Rodricks, J. V. 151 Sasaki, Y. 376 Rodrigo, R. 623 Sato, A. 213 Roe, F. J. C. 465 Sato, K. 622, 626 Roets, E. 61 Sato, S. 213 Roffey, P. 148,150 Satoh, S. 53 Rogers, D. 60 Satter, A. 373 Roholt, K. 55 Scanlon, W. B. 59 Röhrl, M. 462, 463 Scartazzini, R. 60 Rohrschneider, L. R. 465 Schaaf, F. 559 Rl'lhwedder, W. K. 151 Schaafsma, S. E. 416,465 Rolinson, G. N. 53 Schaffner, K. 465 Romanuk, M. 317,321,328,375 Schaich, E. 207 Rooze, V. 626 Schairer, H. U. 390,458,459,461,462,463, Rorsman, H. 580 465,466 Rosati, R. 519 Schantz, E. J. 64,115 Rosen, C. G. 628 Scheibe, G. 465 Rosenberg, L. E. 627 ScheibeI, E. G. 460 Rosengren, A. M. 580 Schelechow, N. 56 Rosengren, E. 580 Schenker, K. 519 RosenthaI, S. 629 Scherer, J. R. 375 Rösler, H. 208, 213 Schiemenz, G. P. 520 Rosprim, L. 215 Schindler, H. 465 Roth, K. 420, 464 Schindler, O. 622 Roux, B. 207 Schmid, H. 277,469,519 Roux, D. G. 179,211 Schmidt, C. G. 466 Rubin, E. M. 623. 629 Schmidt, R. 377, 411, 421, 422, 440, 441, Rüdiger, H. 629 447,453,454,465 Rueff, L. 279 Schmidt, R. D. 170,213 Ruhemann, S. 281 Schmidt, U. 232,236,281 Rüsch, M. E. 116 Schmitt, S. M. 57 Rush, J. E. 623 Schmitt, W. 60 RusselI, P. 579,581 Schnaare, R. L. 57 RusselI, T. J. 57 Schneider 522 Ruzicka, L. 117, 284, 342, 375, 410, 465 Schneider, C. H. 60.61 Ryan, C. W. 54.56 Schneider, R. S. 148 Ryan, J. J. 280,281 Scholz, H. 274 Rydon, H. N. 55 Schönsiegel, I. 214 Schormüller, I. 461 Sacchi, S. 581 Schorno, K. S. 373 Sachiko, E. 211 Schorr, M. 55, 60 Sachs 189 Schossberger, E. 281 Saffiotti, U. 465 Schrauzer, G. N. 583, 622, 623, 624, 626. Sakrikar, S. 623 627,628.629 Sakuma, R. 375 Schreiber, K. 466 Salaman. M. H. 465 Schroeder, H. W. 148

41" 644 Namenverzeichnis. Author Index

Schulman, M. 628 Silverman, R. B. 623 Schulz, J. 463 Silvestri, H. H. 57 Schumacher, R. 117 Sim, G. A. 116, 148, 373 Schwartz, L. 579 Sime, 1. G. 464 Schwartz, M. A. 57,60,61 Simes, J. J. H. 207 Schochau,M.232,236,281 Simmens, St. C. 117 Scott, A. I. 56, 234, 240, 241, 243, 253, 255, Simon, G. L. 60 257, 258, 259, 263, 264, 265, 266, 269, Simonsen, J. L. 374 276,27~280,281,465,469 Simpson, T. H. 154, 214 Scott, de B. 150 Simpson, T. J. 116 Scrimgeour, K. G. 629 Singh, R. K. 364,373 Seck, J. A. 623,624,628 Sinn, M. 186, 187, 188, 189, 190, 191, 214, Sedgwick, J. A. 458 215 Segal, A. 466 Sivak, A. 465,466 Seggery, P. 56 Sizer, I. W. 532,578,581 Seibi, J. 624 Sjöberg, B. 53,55,58 Seiji, M. 575 Sjöland, S. 281 Seikel, M. K. 183, 184, 186, 190, 191, 211, Sjolander, N. O. 280 214 Skingle, D. 277,281 Selby, K. 117 Slooten, J. van 463 Seligmann, O. 214,215 Smalley, E. B. 148 Semmler, F. W. 281 Smart, M. L. 60 Sensi, P. 55 Smiley, K. L. 624 Senoh, S. 569, 581 Smit, C. 1. B. 211 Senyavina, L. B. 58 Smith, D. C. C. 275 Seshadri, T. R. 165,206,208,209,211,212, Smith, E. Lester 624 214 Smith, G. F. 520 Sessa, G. 467 Smith, H. 58, 60, 275 Seto, H. 151 Smith, H. G. 276 Shakhova, M. K. 213 Smith, J. T. 60 Shakir, M. H. 576 Smith, P. 1. 581 Shalaby, A. F. 187,214 Smith, R. R. 57 Shamma, M. 518 Smith, S. E. 371,375 Shankland, D. L. 116 Smithey, R. J. 60 Shannon, G. M. 151 Smyth, E. 624 Shaw, N. 624 Smyth, R. D. 622,626 Shear, M. J. 465 Snatzke, G. 117, 459, 465 Sheehan, J. C. 7, 41, 58, 60 Snell, J. F. 275 Shepherd, M. G. 277 Snell, R. S. 581 Sheppard, A. H. 150 Sobel, H. 623 Sheridan, A. 150,151 Sobolov, M. 624 Shibata, S. 188 Soeder 187 Shikata, T. 150 S;est, T. C. van 151 Shimizu, S. 622,624,626 Soff, K. 208 Shimokoriyama, M. 189, 198,214 Soliman, G. 281 Shoji, E. 62 Soma, N. 62 Shotwell, O. L. 149,151 Songstad, J. 623 Shubik, P. 379,459,465 Sonnet, P. E. 519 Sibert, J. W. 623, 624, 628 Sorm, F. 284, 285, 288, 289, 290, 291, 292, Sice, 1. 380, 465 318,372,374,375,376 Siewinski, A. 116 Sosa, F. 214 Sigg, H. P. 57,114,115,116,117 Southgate, R. 54,59 Sikorski, J. 579 Sparreboom, S. 149 Namenverzeichnis. Author Index 645

Spensley, P. C. 151 Sugimoto, Y. 624 Spies, J. R. 380,460,465 Sugita, E. T. 55,56 Spietschka, W. 578 Sugiyama, N. 580 Spitzer, W. A. 57,60 Sulser, H. 375 Spitzner, E. B. 520 Sunko, D. 275 Spray, G. H. 627 Sunthankar, S. V. 582 Sprecher, M. 626 Süss, R. 466 Sprinson, D. B. 626 Sussmann 544 Sproxton, F. 281 Sutheriand, I. O. 280 Spry, D. O. 55,60 Sutheriand, R. 61 Stadtman, E. R. 281,627,628 Sutherland, S. 212 Stadtman, T. C. 627, 628 Sutheriand, S. A. 56 Stähelin, H. 116 Suzuki, A. 214 Stambouli, A. 180, 189,213 Suzuki, F. 626 Stanfield, M. K. 54 Suzuki, M. 375 Stavely, H. E. 54 Suzuki, S. 117 Stavrianopoulos, J. 629 Svedberg, D. P. 371 Stedman, R. J. 57 Swan, G. A. 521, 543, 544, 545, 546, 547, Steele, B. D. 276 549,550,551,567,568,570,575,576,578, Steelink, C. 564, 582 581 Steere, D. E. 275 Swenson, C. A. 623 Steglich, W. 281 Switzer, R. L. 626 Steinberg, H. 416,465 Sykora, V. 375 Steinegger, E. 214 Syrdal, D. D. 293, 304, 353, 371, 372, 375 Steinfelder, K. 466 Szabo, L. 513 Stelfox, A. R. 275 Szab6, G. 577 Stephen,1. F. 236,279,281 Szantay, Cs. 473,486,487,513,518 Stetter, H. 236,281 Szczepanski, Ch. v. 458,462,463,466 Stevens, K. L. 375 Szekely, I. 216 Stewart, A. W. 221,281 Szezö, L. 216 Stewart, F. T. 54,61 Steyn, P. S. 150 Tabor, C. W. 578,580 Stich, L. 210 Tabor, H. 578,580 Stjernholm, R. 626,627 Tada, M. 279 Stockdale, B. R. 276 Tadeka, R. 373 StoU, Ch. 114,116 Tagishita, K. 213 Stoloff, L. 151 Takahashi, H. 582 Stoodley, R. J. 54,57,59,61 Takahashi, K. 58 Stork, G. 333, 334, 340, 375, 506, 519 Takahashi, S. 376 Stotz, E. 282 Takanobu, K. 58 Stoughton, R. B. 575 Takatsuki, A. 117 Stout, G. H. 281 Take, T. 53 Stove, E. R. 54,56 Takeda 190 Stover, B. J. 576 Takeda, K. 374 Stowe, B. B. 208 Takemoto, T. 373 Strague, P. W. 519 Takemura, K. 53 StreU, I. 463 Taku, E. P. 189 Strominger, J. L. 61 Tamao, Y. 624,626 Strong, F. M. 83, 112, 114, 148 Tamm, Ch. 63,114,115,116,117 Stubblefield, R. D. 149,151 Tamm, R. 518 Stubbs, A. L. 576 Tamoni, G. 55 Suarato, A. 581 Tamura, G. 117 Subramanian, S. S. 188,215 Tamura, S. 214 646 Namenverzeichnis. Author Index

Tan, S. F. 243, 268, 276 Trost, B. M. 368, 376 Tanabe, M. 151 Tsai, L. 627 Tanaka, N. 151 Tschirsch, A. 466 Tanenbaum, S. W. 274 Tsiang, H. G. 623 Tarnura, Ch. 213 Tsingaridas, K. 214 Tarpley, W. B. 533, 535, 536, 544, 577 Tsushima, S. 61 Tarusova, N. 195, 214 Tullen, P. 372 Tarusova, N. T. 214 Tümmler, R. 466 Taylor, C. G. 519 Turner, F. C. 577 Taylor, M. V. 53 Turner, W. B. 115 Taylor, R. T. 629 Tutt, D. E. 61 Taylor, T. 58 Tybring, L. 55,56,58 Teoule, R. 195,214 Terao, S. 61 Ueno 187 Terashima, N. 149 Umani-Ronchi, A. 624 Tessier, J. 459 Underwood,1. G. 148, 150 Testa, E. 54 Underwood, W. G. E. 53 Tettamanti, A. K. 164,216 Urbach, F. 575 Thathachari, Y. T. 563,582 Uskokovic, M. R. 519 Thelin, H. 55 Usmani, I. N. 212 Thielmann, H. W. 421, 422, 458, 459, 462, 465,466 Vanderhaeghe, H. 55, 61 Thieme, H. 214 van der Hoeven, M. G. 6,61 Thies, P. W. 214 Van der Merwe, K. J. 150 Thomas, A. F. 380,466 van der Zuiden, A. S. M. 149 Thomas, F. 282 van Dorp, D. A. 149 Thomas, M. 582 Van Duuren, B. L. 426,465,466,467 Thomas, R. 145,151,281 Vanek, Z. 151 Thompson, K. V. A. 117 Vangedal, S. 56,115,458 Thomson, P. J. 275 Van Heyningen, E. H. 54 Thomson, R. H. 522, 533, 539, 582 Van Pelt, J. G. 150 Thumm, K. 465 Van Potter, R. 466 Timms,D.58 Van Scott, E. J. 575 Tilak, B. D. 582 van S~est, T. C. 151 Tipper, D. 1. 61 van Slooten, J. 463 Tipson, R. S. 213 Vanstone, A. E. 116 Tobias, P. S. 281 Van Tamelen, E. E. 218, 282, 470, 475, 476 Toeplitz, B. 54 483,495,518,520 Töke, L. 518 Van Woert, M. H. 582 Tolliday, P. 54 Varenne, P. 213 Tollin, G. 564,582 Varma, K. R. 376 Tominori, T. 180,211 Velluz, L. 410,466 Tomita, B. 292,375 Venkataramani, P. S. 376 Toohey, J. I. 622 Vercauteren, R. 582 Toraya, T. 624 Vermes, B. 208,215 Towers, G. H. N. 281 Verrett, M. J. 151 Towner, R. D. 57 Vestner, S. 236,281 Townsend, J. 563,576 Vetvov, A. N. 214 Tracey, M. V. 582 Vignau, M. 459 Traut, M. 466 Ville, A. 207 Traxler, P. 117 Vince, T. D. 62 Treibs, W. 373 Vining, L. C. 580 Troll, W. 467 Vita-Finzi, P. 276 Namenverzeichnis. Author Index 647

Vitols, E. 625,626 Weissenberger, H. W. O. 6,61 Vittimberga, B. M. 117 Weissenfeis, N. 380,460 Vittimberga, J. S. 117 Weissmann, G. 467 Vlattas, J. 518 Welch, St. C. 117 Vles, R. O. 150 Wender, S. H. 200,211,212 Vlietinck, A. 61 Wenkert, E. 473,513,519,520 Volcani, B. E. 622 Wenninger, J. A. 376 Volk, O. 215 Wessely, F. 179,205,215 Vorbrüggen, H. 62 Wetter, O. 466 Vorländer, D. 282 Whalley, W. B. 538,579 Vorster,L.J.151 Wheeler, A. W. 60 Vrkoc, J. 219,376 Whewell, C. S. 579 Vydeeswaran, S. 214 White, L. P. 582 White, W. L. 117 Wachter, M. P. 257,258,278,282 Whitear, A. L. 278,280 Waggott, A. 547,549,551,567,570,575,581 Whiting, M. C. 115 Wagner, E. S. 61 WhitIock, H. W. Jr. 370,376,627 Wagner, G. 461,464,465,466 Wiek, E. L. 148 Wagner, H. 153,174,177,179,180,187,188, Wickberg, B. 520 189, 190, 206, 207, 208, 210, 211. 212, Wiesinger, D. 116 214,215,462 Wigner, G. 460 Wagner, O. W. 624 Wildi, G. 210 Waiss, A. C. Jr. 151, 165,208 Wiley, M. 151 Wakil, S. J. 282 Wiley, R. H. 282 Walerych, W. 624 Williams, A. L. 151 Walkowiak, M. 519 Williams, D. H. 190,212 Wallace, J. W. 186,215 Williams, D. L. 627 Walling, C. 577 Williams, F. R. 628 Wallwork, S. C. 149 Williams, J. R. 369,376 Ward, N. 58 Williams, K. K. 518 Waring, W. S. 115 Williams, N. R. 208 Warren, G. H. 62 Williams, R. J. P. 623,628 Wassermann, H. P. 565,582 Williamson, W. R. N. 208 Wasson, F. I. 61 Wilmarth, W. K. 623 Watanabe, T. 53 Wilson, D. V. 277 Waters, J. M. 148 Wilson, K. G. 186,212 Waters, T. N. 148 Wilson, M. C. 116 Waters, W. A. 533,582 Wilson, N. D. V. 519 Waynforth, H. B. 149 Wilson, R. M. 626 Weber, F. 463 Windgassen, R. J. 622,623,626,629 Weber, H.-P. 116 Winfield, M. E. 626 Weber, J. H. 622,628 Winstein, S. 299,372 Webster, G. R. B. 280 Winterfeldt, E. 469,519,520 Wehmer, C. 467 Winzheimer, E. 282 Weichet, J. 59 Wiseman, G. A. 278 Weiler, L. 279 Witkop, B. 569,581 Weinreb, S. M. 148 Witte, I. 464 Weisbach, J. A. 518 Wittek, P. J. 239,282 Weisblat, D. A. 625 Witter, R. F. 282 Weisleder, D. 151 Witz, D. F. 582 Weiss, U. 275 Wogan, G. N. 148,150, 151 Weissbach, H. 622,624,626,629 Wolfe, J. F. 282 Weissbluth, M. 576 Wolfe, R. S. 628 648 Namenverzeichnis. Author Index

Wolfe, S. 61,62 Yamaoka, M. 59 Wolffersdorff, R. v. 460 Yamasaki, M. 303,376 Wolfner, A. 208,210 Yamazoe, Y. 373 Wolfrom, M. 213 Yasunari, Y. 518 Wolinsky, J. 518 Yasunobu, K. T. 553,582 Wolman, M. 579 Yates, R. L. 376 Wong, E. 155,215 Yazaki, Y. 278 Wong, R. Y. 117 Yeboah, S. K. 116 Wood, B. J. B. 576 Yim, N. C. 518 Wood, H. C. S. 276 Yoshikoshi, A. 375 Wood, H. G. 626,627,628 Y oshimoto, M. 62 Wood, J. M. 625,628 Yoshioka, H. 207,212 Woodland, S. 212 Yosioka,1. 318,325,373,376 Woods, D. D. 629 Yurchenko, J. A. 62 Woods, H. J. 579 Woods, L. L. 282 Zahlan, A. B. 576 Woodward, R. B. 38, 60, 62, 469, 487, 497, Zähner, H. 115 518,519 Zalkow, L. H. 291,373,376 Work, S. D. 282 Zanotti, L. 581 Worster, P. M. 341,375 Zechmeister, K. 463 Wright, C. 1. 527, 579 Zeller, P. 60 Wright, D. 544,545, 567, 568, 581 Zemelman, R. 54 Wright, 1. G. 54,60,280,470,520 Zemph~n, G. 162, 164, 165, 166, 191, 192, Wu,G.-M.60 193, 194, 195, 196, 198,200,202,215,216 Wyard, S. J. 575 Ziegler, E. 282 Ziegler, F. E. 509,518,519,520 Yagishita, K. 211 Zirner, J. 193, 209 Yalpani, M. 277 Zito, R. 531,578 Yamada, K. 366, 376 Zürcher, W. 117 Yamada, R. 626 Zwitkowits, P. M. 255,275 Yamamura, S. 234, 240, 258, 282 Zygmunt, W. A. 54 Sachverzeichnis. Subject Index Von· By

A. SIEGEL, Wien

Acacetin 156, 157, 160, 161 ß-L-Acetobrom-arabopyranose 191, 193, -, -7-0-diglucuronid 173 205 -, -di-C-glykoside 185 et-Acetobrom-D-galaktopyranose 191,201, -, -7-g1ucosid 200 205 -, -glucuronid 173 et-Acetobrom-gentiobiose 193 -, -7-0-neohesperidosid 161 et-Acetobrom-D-glucose 179,191, 193, 199, -, -7-0-rutinosid 160, 162 200,202,204,205 Acaciin -+ Linarin 160, 162 et-Acetobrom-glucuronsäuremethylester 191, Aceraceae 187 201 Acer palmatum 187 et-Acetobrom-neohesperidose 192, 195, 197 Acetaldehyde 98, 509, 594, 598, 599 et-Acetobrom-primverose 193 -, -dimedone 98 et-Acetobrom-rhamnose 191, 192, 193, 205 Acetate 143, 611, 614 et-Acetobrom-rutinose 195 -, Biosynthesis 614f, 617 et-Acetobrom-sophorose 193 -, 13C-Iabelled 141 et-Acetobrom-vicianose 193 -, 14C-Iabelled 102,104, 144 et-Acetobrom-D-xylopyranose 191, 205 -, incorporation in verrucarin A 104 Acetobromzucker 194, 195, 196, 201, 203 -, synthetase 613 -, Darstellung 19lf Acetessigester s. acetoacetic acid, ester et-Acetochlor-et-L-rhamnose 192 Acetic acid 36, 39, 40, 41, 90, 91, 93, 102, et-Acetochlor-et-L-rhamnosido-6-0-glucose 104,132,135,136, 138, 140, 162, 191, 195, 191 218,221,223,225,260,272,322,337,341, Aceton s. Acetone 366,367,368,371,395,418,420,421,422, Acetondicarboxylic acid, mixed carbonic 434,436,441,449,450,451,514,558,586, anhydride 234 614 Acetondicarboxylic acids, diethyl esters 244 -, methyl ester 229 Acetone 5, 24, 78, 79, 90, 92, 101, 194, 197, -, mixed anhydrides 4, 6 198,246,311,316,370,383,384,387,388, Acetic anhydride 26, 27, 28, 30, 31, 33,41, 393,395,403,404,408,424,426,440,441, 71, 92, 133, 135, 136, 138, 140, 173, 191, 555 195,198,202,228,233,234,236,237,240, Acetonitrile 92,93, 191, 192, 368 241,247,248,251,252,322,323,324,329, Acetophenonderivat, glykosidiertes 194 333,335,338,339,341,367,368,398,411, Acetoxycrotophorbolone 436, 437 412,413,416,423,431,432,433,434,435, -, -20-acetate 436 437,439,441,442,448,453,500 [et-Acetoxycyc1opropyl]-carbinol group, Acetoacetate, hemithioketal-protected 236 homoallyl rearrangement 437 Acetoacetic acid 221, 222 20-Acetoxy-9-hydroxy-13, 15-seco-4etH- -, ester 228, 470 1,6, 14-tiglia-triene-3, 13-dione 442 Acetoacetylimidazole 229 2et-Acetoxymethylpenam 32 Acetobromapiobiose 193 2ß-Acetoxymethylpenam 28, 32 650 Sachverzeichnis. Subject Index

Acetylacetone 228, 229, 236, 239, 271 Acorenone B, X-ray analysis 291 -, -monoketal 236 Acorolone 285 4-0-Acetyl-9,10-anhydrophorbol-12,13,20- -, dehydration 285 tridecanoate 418 Acoronene 292, 358 Acetylcoenzyme A 222,226 Acorones 284, 285, 287, 292, 356, 357, 359 2-0-Acetyl-l',3-di-O-benzyl-D-apio-D- -, p-bromophenylhydrazon derivative 290 furanosylbromid 168, 193 -, degradation 286 3-Acetyl-5-formylpyrrole 71 -, dipole moment 289 3-Acetyl-4-hydroxy-methylpyrrole -+ verru- -, infrared spectra 285 carin E 71 -, monobenzylidene derivative 285 Acetylierung 201 -, mono-ethylene-thioketal derivative 287 l-Acetyl-4-methyl-cyclohex-3-ene 109 -,optical rotatory dispersion 289 l-Acetyl-2-methylcyclopentane 307 -, reduction 286, 288 3-Acetyl-4-methylpyrrole 72, 102 -, stereochemistry 288f 4-Acetyl-2-methylpyrrole 71 -, syntheses 298f, 306f Acetylmigration 420, 421 -, X-ray structure analysis 290 Acetylphloroglucinol 223, 252, 255, 259 Acoronol 280 Acetylphorbol 380, 398, 405, 411 Acorus calamus -+ sweet flag 285, 358, 359, 12-0-Acetylphorbol-13-decanoate 425 360 4-0-Acetylphorbol-12, 13,20-tridecanoate Acrolein 510 418 Acrylate 605 3-Acetylpyrrole 71, 72 Actinomyces 523 Achillea !ragrantissima 182, 187 Acupuncture 379 Achorion 112 Acylchlorides 411 Acinos thymoides 160 Acylcobalamins 607 Acocanthera spectabilis 166 Acylcobaloximes 607 Acoradienes 295,304,305,347,354,355,356, Acylglykoside, innermolekulare 176 357 3-Acyl-4-hydroxy-2-pyrones 228,231 -, dehydrogenation 286 6-a-Acyloxypenicillanates 16 a-Acoradiene 292, 293, 355 6-~-Acyloxypenicillanates 16 ~-Acoradiene 294, 348, 356 Acyloin reduction 418 y-Acoradiene 293, 294, 355 Acylphloroglucinol 252, 257 II-Acoradiene 293, 294, 355 Acyl polymalonate route in biosynthesis of Acoradiols 287 polyketides 218 Acoradiones 359, 360 ·4-Acylresorcinol 259 Acoranes 284, 285f, 291, 294, 309, 346, 353, Adams catalyst 420 357 Addison's disease 528 -, infrared spectra 293 Adenine 589, 590, 595 -, mass spectra 296f Adenochrome 565,566 -, structure elucidation 285f Adenochrome-Melanin 523, 565f -, syntheses 298f, 304 Adenosine 601 Acoranone, hydroxymethylene derivative 5'-Adenosine aldehyde 591 287 Adenosine triphosphate -+ ATP 591, 593, ~-Acoratriene 302, 303, 354 611, 612, 613 /19-Acorene 348,350 Adenosylhomocysteine 619 Acorenes 322, 350, 355 Adenosylmethionine 613, 618, 621 a-Acorenol 292, 293, 359 Adenosyl phosphates 591 ~-Acorenol 294, 359 5'-Adenosyltosylate derivatives 591 Acorenone 291, 292, 358 Adipic acid 84, 92, 98, 104 -, hydrogenation 291 -, derivatives 322 Acorenone B 291, 292, 358 Adonis sp. 189 -, dihydroderivative 291 Adonis vernalis 183, 184 -, -p-iodo-o-nitrophenylhydrazone 291 Adonivernith 184 Sachverzeichnis. Subject Index 651

Adrenal glands, hypofunction 528 Air oxidation 71 Adrenaline .... epinephrine 565, 566, 567 Ajmalicin 475, 476, 478, 481, 482 Adrenaline black 565 Ajmalin 495, 497 Aerobacter aerogenes 592, 593 Ajmalin-Typ von Indolalkaloiden 469 Aesculus hippocastanum 167 Akuammicin 481,482 Aflatoxicosis 120, 122, 147 Akuammicin-Gruppe von Indolalkaloiden Aflatoxin-B I 120, 121, 123, 128, 129, 130, 470 131, 132, 134, 137 D-Alanine 17 -, -acetate 132 Alaskanes 285f, 292f, 346f, 353, 358 -, biogenesis 143, 144f -, structure elucidation 285f -, synthesis 134, 135, 136 ent-Alaskane 357 -, trithioketal 130, 131 IX-Alaskene 293,294,295,296,348,349,351, Aflatoxin-B2 121, 123, 128, 131, 132, 133 355, 357 -, biogenesis 146 ß-Alaskene 293,294,295,347,348,349,354, -, synthesis 136f 357 Aflatoxin-B2a 121, 123, 132 -, hydrogenation product 295 -, -acetate 132 ent-ß-Alaskene 355 Aflatoxin-G I 121, 123, 128, 131, 132, 133 Alaskenes 284, 304 -, -acetate 132 Alaternin 170, 171 -, synthesis 136, 137 Albino skin 528 Aflatoxin-G 2 121, 123, 128, 131 Alcohol, denaturing 379 -, biogenesis 146 Alcohol phorbol 404, 409, 431, 434, 440, Aflatoxin-G2a 121, 123, 132 444, 445, 451 -, acetate 132 Aldehyde, aromatische 198 Aflatoxin-M 1 121, 123, 131, 132 Alditolacetate, methylierte 170 -, synthesis 136, 137f Alditole, methylierte 174 Aflatoxin-M 2 121, 123, 131, 132 Aldol condensation 243 Aflatoxins 119f, 128 Aldol cyclization 244, 247, 252, 253, 257, -, carcinogenic properties 120 263, 264, 268, 269, 274 -, melting points 121 Aigae 187 -,optical rotation 121 Alimentary toxic aleukia 120 -, structures 121 Alkali amides 227, 232 -, syntheses 134 Alkali metal ion 592, 593 -, toxicity 147 Alkoholextraktion 163, 173 -, UV-fiuorescence 123 Alkylation 17 Afrosin 182 N-Alkylation 5 Agar diff~sion plaque inhibition method 112 Alkylcobalamins 585,614 Agarofuran 313, 314 Alkylcobaloximes 614 Agarospirane 328 Alkylcobalt derivatives 585 Agarospirol 284, 285, 309f, 330, 363 Alliaria officinalis"" Sisymbrium Alliaria -, -acetate 313 187 -, biogenesis 326 AIliarosid 186 -, degradation 310, 312 Allocedrol 348 -, epoxide 333 Allomelanins 522,523, 532f, 550, 565, 575 -, hydrogenation 311 -, natural 537f -, infrared spectrum 311 Allophorbol 446 -, nmr-spectrum 313 Allylic oxidation 79 -, stereochemistry 313, 326 Allyl-magnesium bromide 138 -, structure 313, 314 Ainus-Arten 167 -, synthesis 333 Alternariol 224, 226, 271, 272, 273 Agar-wood, fungus infected 284 Alumina 7, 82, 101, 123, 292, 293, 294, 318 Agrostis canina 190 Aluminium 36 Agryolobium sp. 188 Aluminiumalkoholat 501 652 Sachverzeichnis. Subject Index

Aluminium chloride 125, 135, 137, 138,233, Anthracene dicarboxylic acid 265 234, 239, 436 Anthraquinone 143, 144, 145, 225 Aluminium isopropylate 414, 415, 437 Antibacterial activity 112 Aluminium oxide s. Alumina Antibiotic activity 64, 112 Ameisensäure s. formic acid Antifungal activity 64, ll2 Amidacetal-Kondensation 478 Antimicrobial activity 4 6-Amidinopenicillin 4 Antimon pentachloride 15 Amines, N-penicilloyl derivatives 21 Antiviral activity ll2 Amino-acetaldehyde hydrochloride 72 D-Äpfelsäure 165 Amino acids, N-penicilloyl derivatives 21 L-Äpfelsäuredimethylester 165 Amino-catecho1 537 Apiaceae 187 Aminochromes 525, 569 Apigenin 156, 157, 160, 161 2-Aminoethanol 599 -, Anhydrohexahydroxy-hexylderivat 179 Amino groups, blocking to prevent acylation -, 14C-markiert 186 4 -, -7-(p-cumaroyl)-ß-D-glucosid 176 5-Aminolevulinic acid 102 -,6,8-Di-C-glykoside 184 Aminomutases 609f -, 6-C-D-Glucopyranosylderivat 179 6-Aminopenicillanic acid 2, 3f, 5, 13, 15, 23 -, 8-C-D-Glucopyranosylderivat 179 -, alkylation 17 -, -4'-glucosid 201 -, benzyl esters 14 -, -4'-glucosid-7-methyläther 201 -, diazotation 16 -, -5-0-glucosid 202, 203 -, methoxymethylesters 14 -, Ci-Glucosyl-Cs-xylosylderivat 184 -, polymerization 22 -, -glucuronid 173, 201 ex-Amino-propionaldehyde hydrochloride 72 -, -7-0-monoglucosid 195,200 Amino-quinone 537 -, C-Monoglykoside 178, 179 Ammonia 48, 93, 103, 200, 228, 231, 232, -, -7-0-neohesperidosid 161 299,329,330,342,367,491,524,538,555, -, -7-0-rutinosid 160, 162 588, 598 -, -6-C-xylosid 184 Ammonium ion 593 -, Ci-Xylosyl-Cs-glucosylderivat 184 Ampicillin 5, 9, 22 Apiin -+ 2-0-(D-Apiofuranosyl)-ß-D-gluco• Andrographis echioides 202 pyranosyl-7 -0-4' ,5,7 -trihydroxytlavon Anethum graveolens -+ Peucedanum 168, 169 graveolens 187 Apiobiose -+ 2-0-ex-D-Apiofuranosyl-ß-D• Angiospermae 187, 188, 190 glucopyranose 159, 168 2-Anhydro-2,3-epoxyroridinic acid 73 Apiofuranose 168 cis-Anhydro-mevalonate 106, 107 2-0-ex-D-Apiofuranosyl-ß-D-glucopyranose Anhydropenicillins 45 159, 168 -, chlorination 43, 45, 46 2-0-(D-Apiofuranosyl)-ß-D-glucopyranosyl- -, reactions 45 7-0-4',5,7-trihydroxytlavon 168, 169 -, rearrangement 44 D-Apiose 155, 169 2-Anhydrororidinic acid 73, 95 Apium graveolens 169 -, dimethyl ester 95 Apium petroselinum 168 Anhydro-ß-rotunol 362 Apium sp. 168 Anionotropic rearrangement, acid catalyzed Apotrichothecane 78, 81, 82, 83 99 -, derivatives ll4 Anisaldehyd 197 -, ketones, c. d. 83 ex,ex' -Annelation to spirodecanes 308 Aquilaria agallocha 309, 363 Anthemis-Arten 168 Aquilaria lancea 363 Anthemis nobilis 176 Aquocobalamin 586 Anthemosid 176 6-0-(ex- L-Arabinopyranosyl)-ß-D• Anthocyanidin-acylglykoside 175 glucopyranose -+ Vicianose 159, 169 Anthocyanreihe, Acylverbindungen 174 L-Arabinose 155, 184, 185 Anthracene derivatives 265 Arabinosyl-galactose 159 Sachverzeichnis. Subject Index 653

3-Arabinosyl-7-glucosid 159 Autoxidative dopa-melanin 542 3-Arabinosyl-rhamnosid 159 Avena-Arten 190 Araceae 186, 190 Averantin 141 Arachidonic acid 427 Aversin 141, 142 Arecaceae 190 A verythrin 141 Arginine 609 Avicularin 155, 156 Aromadendrin-7-0-glucosid -+ Dihydro- Axolotls 530, 562 kämpferol-7-glucosid 199 Azaleatin -+ 5-Methyl-quercetin-3- Aromatization 263, 264, 269 glucuronid 173,201 Arsenate 617 Azide as amine precursor 4 Arsenite 617 Azide ion 45, 46 Artemisia transsiliensis 187 Azido compounds 35 Artischocke 171 -, reduction to amines 45 Arum-Arten 190 Aziridine 516 Ascomycetes 539 Azo compounds 30 Ascorbic acid 526, 531, 554, 564 Azukia angularis 166 Aspalathin -+ 3' -ß-D-Glucopyranosyl- Azulenes 309,315,408,428 3,4,2',4' ,6' -pentahydroxy-dihydro• Azulenic compounds 287 chalkon 182 Aspalathus acuminatus 179 Bacillus salmonicida 523 Aspalathus linearis 182, 188 Bacterial free suppuration 379 Aspartic acid 557, 558 Bacterium symbioticum 523 Aspergillin 538, 539 Baeyer-Villiger oxidation 288 Aspergillus jlaviceps 226 Baicalein 157 Aspergillus jlavus 120, 123, 132 -, -glucuronid 173 -, toxins 120 Banana 567 Aspergillus niger 538 Baptisia-Arten 162 Aspergillus parasiticus 123 Baptisia lecontei 160 Aspergillus sp. 112 Baptisia sphaerocarpa 163 Aspergillus versicolor 120, 123, 124, 128, 141 Barakol 224, 270, 271 Aspertoxin 122, 128, 132 Barbilophozia barbata 355 -, monoacetate 128 Barium, binding by eumelanins 554 Aspidospermidin 509 Barium hydroxide 220, 221, 230, 404, 414, Aspidospermin 501, 505, 507, 510 415 Asteraceae 174, 187 Barium oxide 414, 415 Astragalin 169 Barium sulfate 404 Äthanol 36, 101, 155, 158, 167, 169, 196, Baumwollblüten 202 197, 229, 287, 294, 329, 337, 380, 396, Bayin 178 404, 407, 411, 427, 430, 538, 542, 556 BCD s. ß-Cyc1odextrin Äthylacetate s. Ethyl acetate Beckmann rearrangements 92,93,517 Äthyljodid 497 Beckmann-Umlagerung s. Beckmann ATP s. Adenosin triphosphate rearrangements Atractylodes lancea 361 Bellis-Arten 168 Atropa belladonna 166 Benzalcumaran-3-on s. Auron Atsinosid -+ Didymin 160 Benzalcumaranonglykosid-acetate 198 Aureusidin 157,158 Benzaldehyde 285, 286 -, -glucoside 157 Benzazulenes 428 -, -6-rutinosid 198 Benzene 66,67,101, 138, 140, 193,320,331, Auron -+ Benzalcumaran-3-on 154, 155 473 -, -glykoside 157, 158 Benzene ring, oxidative fission 545 -, -rutinosid 163 cx-Benzobromrhamnose 192 Aurone, selektive Glykosidierung 198 Benzoic acid 411 Autoxidation 563, 564, 568 Benzol s. Benzene 654 Sachverzeichnis. Subject Index

Benzonitrile oxide 236 Biochanin A-7-glucosido-5-maleat 176 Benzopersäure 86 Biological activity Benzophenones 264, 272 Croton oil factors 386f, 398 Benzopyran derivatives 261 Diterpenes 455 o-Benzoquinones 532, 533, 534, 540, 563 Phorbol esters 379f Benzothiazole 574 Roridins 112, 114 Benzoylacetaldehyde 243 Trichothecane derivatives 112, 114 Benzoylacetone 228, 236, 243 Verrucarins 112, 114 -, dilithium salt 236 Biological cyclization reactions of poly- Benzoylated melanin 567,568 carbonyl compounds 255 Benzoylation 237,478 Biphenylcarbonsäure 177 Benzoyl chloride 413, 437, 439, 448, 549, ot-Bisabolene 305 567 ~-Bisabolene 304, 305 Benzoylierung s. benzoylation y-Bisabolene 109,110,111,302,304,305 Benzoyl initiation of polycarbonyl chains Bisabolenes 304 252 ot-Bisabolol 109, 349 m-Benzoyloxyphloracetophenon 201 ~-Bisabolol 347,348,349 2-Benzoyl-phloracetophenon 196 2,5-Bis-(ß-aminoethyl)-benzoquinone 570 Benzoylphloroglucinol 247, 249, 250 Bisdehydrophorbol 414, 431, 432, 441, 442 Benzoylwanderung 200 -, -12,20-diacetate 414,415,431,434 Benzyl alcohol 138 Bisdehydrororidinic acid 94 Benzylation s. Benzylierung Bis-dimethylglyoximatocobalt 584, 587 3-Benzylcephem ring system 38 Bis-Glykosid-Kombinationen 158, 159 Benzylchlorid 202, 230, 365 Bishemithioketal 236 Benzyl 6-diazopenicillanate 14, 16 Bis-isoxazole 236 Benzyl esters 4 Bis-pyranopyrandione 241,265 Benzylierung 133, 135, 138,200,202 -, cleavage-recyclization 266 -, partielle 201,203 N,O-Bis-(trimethylsilyl)-acetamide (BSA) 11 p-Benzyloxybenzoesäure-anhydrid 201 Bisulfate salts 28 Benzylpenicillenic acid 21 Black tea 539 Benzylpenicillin ..... Penicillin G 2 Blastomyces 112 Benzylpenicilloic acid, thioester epimers 21 Bleitetraacetat s. Lead tetraacetate Benzyl 6ot-phenoxyacetoxypenicillanate 16 Boehmeria nipononivea 160 Benzyl-thiolat 498 Boranate s. Sodium borohydride Benzyl-3,5,6-tri-O-benzyl-ot-D-gluco- Borhydrid-Reduktion 173, 174 furanosid 193 Boron hydride 307 Benzylurethan 517 Boron trifluoride 291,324,436,492,509,510 Berenblum experiment 379, 384 -, etherate 301,302,304,329,368 Beta vulgaris 188 Bothriochloa intermedia 358 Betula-Arten 167 Bracteatin 157, 158 &2.2'_ Bi-(2H-1 ,4-benzothiazine) 572 -, -O-glucosid 157 Bicyclo[4.1.0]-heptane 410 Brassicaceae 187 Bicyclo[3.I.I]heptane system 439 Brassica napus 162 Bicyclo[3.2.0]heptane system 439 Brassicosid 203 Bicyclo[4.1.0]heptane system 431,435, 436f, Braunstein 494 441,442,443,444 Bredereck-Verfahren 192 Bicyclo[IO.l.O]tridecanyl-13-acetate 408 Briza media 190 Bicyclo[4.5]undecenone 369 Brom s. Bromine Bicyclovetivenol 317,318,328 Bromide ion, nucleophilic reactivity 588 tert. Bicyclovetivenol 318 Bromierung 194,203,337,420,421,437 Bignoniaceae 174 Bromination s. Bromierung Bignonosid 175, 176 Bromine 15, 105, 106, 202, 284, 420, 421 Biochanin A-glucosid 176 -, in natural products 284 Sachverzeichnis. Subject Index 655

Brom-nicotin-amid 509 Carbon monoxide 597 p-Bromobenzoyl chloride 413 Carbon tetrachloride 65, 301, 386, 387, 388, 3-0-[p-Bromobenzoyl]-neophorbol-13,20- 389,390,401,402,403,420,421,444,446 diacetate 416 I, I' -Carbonyldiimidazole 3 5-Bromofuroyl chloride 413 Carboxamido group 4, 6 I-Bromo-4-methyl-pent-3-ene 109 6-Carboxamidopenicillanic acids 9 6-a.-Bromopenicillanate 15 N-Carboxy-a.-amino acid anhydrides 3 N-Bromosuccinimide 24,45, 46, 420 ß-Carboxyethylcobaloxime 606 Bromwasserstoff s. hydrogen bromide Carboxylation 236 Bromus erectus 190 Carboxylic acid, blocking groups 4 Bryonia dioica 188 l-Carboxy-2-methyl-cyc1opent-l-ene-3-one Bryophyllosid 175 80 Bryophyllum daigremontianum 175 Carboxymethylderivatives 616 Bryophyta 187 I-Carboxy-2-methyl-I-propenyl-ester group BSA s. N,O-Bis-(trimethylsilyl)-acetamide 35,36 Buddleia-Arten 160 Carcinogenic activity 120, 122, 147, 380, 386 Bupleurum Jalcatum 162 Carcinogenic aromatic hydrocarbons 379 Butadiencarbonester 488 Cardamine pratensis 167 Butanediols 592 Carex-Arten 190 1,4-Butanedithiols 608,615 Cariophyllaceae 186, 188 Butanethiol 329 Carotenoids 571 I-Butanol 6,204,444 Carotol 302 -, Extraktion 204 Castanospermum australe 180, 189 t-Butanol s. tert. Butyl alcohol Catalase 544,545,546,548,551 Butan-l-01-3-one derivative 106 Catalpa bignonioides 175 3-Butenylmagnesium bromide 306 Catechol 104, 523, 528, 531, 532, 533, 534, tert-Butyl alcohol 10,46,83,337,416,491 536,539,544,546,560 -, deuterated 12 -, enzymatic oxidation 535, 536, 544, 552 t-Butyl hypochlorite 42 Catecholase activity 531 Butyl lithium 228,229,365 Catechol-Melanin 532f, 552, 562, 563 t-Butyl mercaptan 42, 43 Catechol-melanoproteins 537 Butyric acid 288 Cathartic activity 380 Butyryl-phorbol-dodeanoate 402, 427 Catharticin 170 Cation-exchange capacity of melanins 554 Cadalene 286 Cedradiene 302 Calcium, binding by eumelanins 554 Cedrene 284,290,346,349,351 Calcium carbonate 14, 138,412 -, biosynthesis 299, 304, 342 Calcium methoxide 256, 257 -, 2-epimer 302 Calycotome spinosa 188 -, precursors 292f Camellia sinensis 171 -, synthesis 300,301 Camouflage 554 ~2-Cedrene 348,350 Campnosperma brevipetiolata 244 a.-Cedrene 293,295, 301, 302, 304, 305, 347, Candida albicans 112 348 Capsella bursae-pastoris 160, 200 ß-Cedrene 295 Capsicum-Arten 168 Cellulase 64 Carbobenzyloxy group 4 Cellulolytic properties 64 Carbohydrates 221,225 Cellulose, treatment during the production of 5-Carbomethoxypyrrole-2,3-dicarboxylic textiles 64 acid 557, 558 Centaurea-Arten 168 Carbon dioxide 23, 48, 102, 104, 145, 228, Centaurea cyanus 187 229, 231, 232, 237, 316, 332, 440, 524, Centaurein 194 536, 543, 545, 548, 549, 555, 557, 568, Cephalaria leucantha 180, 188 610, 611, 614, 615 Cephalosporins 31,33 656 Sachverzeichnis. Subject Index

Cephalosporins, synthesis 38 A5-Cholesten-3,7-dione 428 Cephalosporin series 19, 24 Chorio-allantoic membrane 113 Cephaloxin 30 Charisia-Arten 161 Cepham 28 Choroid 554 Cephams 34, 35, 50 Chromane derivatives 66, 68, 69 Cephem 28 Chromatographie Cephems 37,39,40,41 Afiatoxins 123, 132 Chalkon 154,269 Apotrichothecan derivatives 82 -, -2',4'-diglykoside 202 Croton oi! factors 380, 386, 402, 452 -, -glykoside 158, 163, 164, 195, 197, 199, Epiorientin 179 204 C-Glykoside in Weizenkeimen 185 -, -C-glykoside 206 Hinesol 318 -, 2' -O-glykoside 202 Hinesol isomers 338 -, Glykosidierung 194 Isoviolanthin 185 Chamaeeyparis nootkatensis 293, 354, 355 Isovitexin 186 Chamaeeytisus-Arten 188 Melanin fractions 571 Chamaedorea sp. 190 Naringenin-glykoside 204 Chamaerops humilis 190 Orientin 179 Chamigrenes 296 Polyamidchromatographie 203 Chaotropic effect 602 Pyrrolidinderivate 503 Characeae 187 Roridins 65 Charcoal 419,420,428,439 Schaftosid 185 Chenopodiaceae 188 Tigliane derivatives 420 Chick embryo fibroblasts 112 Triketoesters 232 Chininhydrochlorid 164 Verrucarins 65 Chinolin s. Quinoline Vetiven derivatives 322 Chinolizidin-Inversion 481 Vicenine 185 Chinon 488 Violanthin 185 Chlorbutenon 510 Chromatography s. Chromatographie et-Chlorbuttersäure-anhydrid 494 Chromic acid 338 Chloride ion, nuc1eophilic reactivity 588 Chromic trioxide 68, 69, 72, 78, 81, 82, 86, Chlorination 225 90,91,92,97,98, 108, 131,301,307,311, Chlor-Indolenin 482 320, 321, 324, 329, 339, 367,411,416 Chlorine 42, 43, 46 Chromones 244,261 Chloroacetic anhydride 27,28 Chromosomes 113 Chlorobenzene 125 Chrysanthemum-Arten 168 3-Chlorobenzoic acid 25 Chrysanthemum morifal. 160 l-Chlorobenzotriazole 24,43 Chrysin 156, 157, 161 p-Chlorobenzoyl chloride 413 -, -7-0-glucuronid 173,201 Chloroform 65, 66, 67, 101, 126, 397, 400, -, -7-0-neohesperidosid 161 434, 445, 449, 568 -, -7-0-rutinosid 161,162 Chloroformic acid esters 19, 30, 38, 39, 49, Chrysoeriol 156, 157 50,51,52 -, -di-C-glykoside 185 Chloroolefin annelation to spirodecanes 309 -, -7-0-glucoarabinosid 169 m-Chloro-peroxybenzoic acid 100, 108, 337, -, -8-C-ß-D-glucopyranosylderivat 180 422 -, -glucuronid 173 Chloroquine 563, 565 Chrysoeriol-(3' -MethylIuteoIin)-7 -O-apio- Chloropromazine 563, 565 glucosid 169 et-I-Chlor-ß-6-L-rhamnosido-D-galaktose- Cieer arietinum 169 [l,5]-hexaacetat 192 Cichoriaceae 188 l-Chlor-2,3,4-triacetyl-ß-D-galaktose 192 Cinnamoylphloroglucinol 255 et-l-Chlor-2,3,4-triacetyl-glucose 191 Circular dichroism Chlorwasserstoff s. hydrogen chloride Apotrichothecane ketones 83 Sachverzeichnis. Subject Index 657

Cedrenes 294 Orientin 186 Cryptoacorone 360 Phenethylamine 570 Flavanonglykoside 197 Phenylalanin 186 Myrochromanole 70 Precursons of trichothecanes 103 Phorbobutanone 439 D,L-Proline 102 Phorbol 405,406,407,408 Roridin A 105 Roridins 87 Roridinic acid 104 Trichothecane ketones 83 L-Serine 102 Tricyclovetivanone 346 Tumor tissue 559 Verrucarins 87 Tyrosine 543, 554, 555, 574 Cirsium-Arten 160, 161 Verrucarin E 102 Citratpufl"erlösung 196 Verrucarol 107 Citrofoliol ...... Isosakuranetin 160, 161 Vitexin 186 Citrus-Arten 160, 161, 162, 189 Cladium mariscus 190 Citrus-Früchte 163, 194 Claisen condensation 222, 223, 236 Citrus /imonum 163 Claisen cyclization 247, 250, 255, 257, 261, Citrus paradisi 161, 171,203 264,265,269,272,273 Citrus sinensis 160 Claisen rearrangement 255, 257, 258, 302, 13C-labelled compounds 334 Acetate 141 Claviceps purpurea 120 NMR-spectroscopy 103,140 Clematis terniftora 176 14C-labelled compounds Clerodendron trichotomum 173 Acetate 102, 104, 144 Clostridium barkeri 593 1_14C-Acetic acid 226 Clostridium sp. 593, 598, 605 Afiatoxin-B 1 144 Clostridium sticklandii 593, 609 5-Aminolevulinic acid 102 Clostridium tetanomorphum 593, 603 Apigenin 186 Clostridium thermoaceticum 613,614,615 Benzoyl chloride 549, 567 C-13-markierte Verbindungen s. 13C-Iabelled Biosynthetic precursors of verrucarin E compounds 102 C-14-markierte Verbindungen s. 14C-labelled I-Bromo-4-methyl-pent-3-ene 109 compounds Carbon dioxide 104, 548 Cobalamins 584, 606 Cysteine 574 Cobaloximes 584,587,588,606,608,612,620 Diphenylketone 106 -, Co(II)-derivatives 589 Dopa 543, 545, 547, 548, 551, 558, 559, -, nucleophilic activity 588, 589 574 Cobalt chelates 587,589 Dopamine 568 Cobalt in tetradentate, strongfield complexes [2-3H,2-14C]-Geranyl pyrophosphate 109 583, 584 D,L-Glutamic acid 102 Cobalt, nucleophilic activity 586, 587 Glycine 102 Cobalt porphyrins 587 5-Hydroxy-dihydrosterigmatocystin 146 Cobalt(II)-cobalt(I)-reduction potential 587, Isoorientin 186 589 Isovitexin 186 Cocarcinogenic activity 379, 384, 386, 388, Luteolin 186 389,390,391, 392, 398, 401, 402, 452, Melanin 543f, 559 455f L-Methionine 102 Cocarcinogens of Croton tig/ium 377f Methylmagnesium iodide 109 Coenzyme A ester of a triketo acid 252 Methyl-14C-methionin 144 Coenzyme B12 583f [5,6-14C]-4-Methyl-pent-3-ene- -, biosynthesis 591 magnesium bromide 109 -, dependent enzymatic reactions 592f Mevalonate 102, 103, 104, 105, 107 -, dependent mutases 603f 2-rHl-2[14C]-Mevalonic acid 99 -, photolysis 590 Muconic acid 104 -, reactions 589f

Fortschritte d. ehern. org. Naturst. XXXI 42 658 Sachverzeichnis. Subject Index

Coenzyme B12, structure 585 Cresolase activity 531 -, 4' -substituted derivatives 597 Crotalaria-Arten 188 Coenzyme M 611,612,613 Crotin 379 Collidine 301 Crotonic acid 427 Combretaceae 188 Croton oil 380f, 420 Combretum micranthum 188 -, activated hydrophobie portion 399 Commelinaceae 190 -, active principles, resolution 380 Commelina communis 190 -, earcinogenic activity 380 Compositen-Pamilie 157 -, ehromatography 380f, 386, 387 Compound 379 Y 64 -, cocarcinogenic activity 384, 456 Condyfolin 494 -, diterpene esters 333f,454f Condylocarpin-Typ von Indolalkaloiden 470, -, diterpenes 444f,454f 488 -, fractionation 38lf Conium maculatum 160 400,403 Conjunctivitis 379 -, hydrophilic portion 385, 386, 392, 399, Copaene 349 400,403 Cope-rearrangement 304 -, hydrophobie portion 385, 398f Copper 331,332,531 -, irritant aetivity 383f, 399, 456 Copper-bronze catalyst 259 -, mass spectrometry 394f Copper-protein complexes 530 -, toxicity 383, 456 Copper-secondary amin complex 530 Croton oil factor A 386, 388, 389, 392, 396, Coreopsidinae 157 397, 398, 403, 425, 426, 452, 455, 456 Coronaridin 505 Croton oil factor A' 401,402, 403, 425, 455 Corrin 583f Croton oil factor B 386, 390, 391, 392, 395, -, dependent enzymatic reaction 583f, 610f 396,397,402,425,426,452,455 -, methylation 620 Croton oil factor B' 401,402,403,425, 455 -, properties 584f Croton oil factor D 45lf -, propylation 614 Croton oil factor D' 45lf -, reactions 584f Croton oil faetor E 45lf Corrinoid coenzymes 583f Croton oil factor E' 451 f Corylus-Arten 167 Croton oil factors 403, 404f, 410, 416 Corynantheidin, Totalsynthese 471f -,IR-spectra 396f,427 Corynanthein, Synthese 470f -, mass-spectra 397, 425, 426, 427 Corynanthein-Typ von Indolalkaloiden 469, -, NMR-spectra 396f, 422 495 -, structure 42lf Cosmos bipinnatus 200 -, synthesis 413 Cosmosiin 200 -, UV-spectra 396f Cotoin -+ Phloroglucinol methyl ether 252, Crotonol 380 253,258 Crotonol acid 380 Cotton effects 83, 165, 197 Crotonoside -+ Isoguanine-D-riboside 378 Coumaran-3-one system 138 Croton resin 380, 420 Coumarins 261,269,272,273 Croton tiglium 377f Coumarin synthesis 136, 137 Croton zambezicus 188 Counterirritant 379 Crotophorbolone 436,440,441,442,443 Craig distribution 382, 387, 388, 389, 390, -, -enol-13,20-diacetate 436,437 391, 392, 400, 401, 402, 403, 444, 445, -, -20-acetate 436,441,442 446,452,453 Crotyl bromide 334 Crataegus-Arten 189 Cruciferen 186 Crataegus curvisepala 184 Cryptoacorone 288,289,360 Crataegus oxyacantha 182 Cryptotaenia canadensis 187 Cratenacin 184 Cucurbitaceae 186, 188 Creatinurea 113 Cu(II)-glycine chelate 23 p-Cresol 531 Cumaranon-glykoside 198 Sachverzeichnis. Subject Index 659 p-Cumaroyl-glucose 175 Cyperus longus 190 7-p-Cumaroyl-kämpferol-3-glucosid 174 Cyperus rotundus 362 p-Cumarsäure 175 Cyrtandra pendula 189 Cuminum cymium 168 Cysteic acid 557, 558 Cupric acetate 17 Cysteine 523,524, 553, 558, 571, 573, 574 Cupric sulfate 35 Cytisosid 178, 180 Cuprous chloride 139, 140 Cytisus-Arten 188 Curcumenes 304, 348 Cytisus communis 161 y-Curcumene 305,347,349 Cytisus commutatus 165 Curie law 564 Cytisus laburnum 180 Curtius .reaction 38, 48 Cytisus linifolia 189 Curvulinate 270,271 Cytisus purgans 161, 165 Cuttlefish -+ Sepia officinalis 554, 555 Cytisus scoparius 189 Cyanessigester s. cyanoacetic ester Cytostatic activity 64, 112, 113 Cyanidin-glykosid 167 Czapek-Dox medium 65 Cyanoacetamide 311,312 Cyanoacetic ester 311, 312, 473 Cyatheaceae 187 Dahlia tubers 524 Cyathea fauriei 187 Dahlia var. 160 Cyclization 145,219,221,222,223,227,228, Daidzein -+ 7,4'-Dihydroxyisoftavon 181 232, 234, 241, 243, 246, 247, 248, 250, -,8-Formylderivat 181 252,253,260,262,263,266,270,271,272, Dalbergia lanceolaria 169 273,274 Dalbergia paniculata 188 Cyclization, dehydrative 246 Daldinia concentrica 539 ß-Cyc1odextrin -+ BCD 23 Daucane type sesquiterpene 302 Cyc1oheptaamylose 23 Daucene 303, 304 Cyc1oheptatrienyl-system 418 DDQ -+ 2,3-Dicyano-5,6-dichloro-l,4- Cyc1oheptenone 302 benzoquinone 329 2,4-Cyc1ohexadienone rearrangement 328 Deacetylierung 168 Cyclohexane 391,392 Decahydrovetivazulene 317 Cyc1ohexanone chromophores, cotton effect Decanoic acid 395 83 12-0-Decanoylphorbol-13-acetate 425, 426 Cyc1ohexanone derivatives 285, 286, 287, Decarboxylation 72, 126,234, 312, 334, 470, 288, 305, 322 473,525,545,548,555,615 Cyc10hexylamin 9 Decarboxylative dimerization 240 Cylopentane-fused cyc1ohexanone 316 Decarboxylierung s. decarboxylation Cyc1opentanone chromophores, cotton Dedoublement partiel 70 effect 83 Dehydrierung s. dehydrogenation Cyc1opentanone derivatives 285, 286, 287, Dehydroacetic acid 219, 221, 229, 236, 244 288,290,322 -, transformations 220, 228 Cyc1opentenone 145 Dehydrobromierung 195,203 Cyc1opentenone-coumarin ring system 136 Dehydrogenation 285, 286, 287, 316, 322, Cyc1opentylidenecyc1opentanone 369 428,473,479 Cyclopropane ring, c1eavage with HBr 109 Dehydrolinalool 302, 303 Cyc1opropane ring, opening 437 2'-Dehydroverrucarin A 65, 66, 73, 74, 84f, Cyclopropane ring, UV -absorption 420 86,88, 111 Cyc1opropanols, tertiary 416, 417 -, NMR-spectrum 76, 77 Cyc1opropyl ketones 322,331,333 -, structure 88 Cyc1opropylmethyl ketone 109 -, thin layer chromatography 101 Cyc1opropyl vinyl carbinol 368 2-Dehydro-verrucarinate 106, 107 Cynara scolymus 160, 162 Demethylation 234 Cynarotriosid 171 Demethylsterigmatocystin 122, 123, 127 Cyperaceae 190 Denaturing of alcohol 379

42* 660 Sachverzeichnis. Subject Index

3-Deoxo-3 ß-[p-bromobenzoyloxy]phorbol- Deuterium incorporation during epimeriza• 12,13,30-triacetate 411 tion of penicillins 11, 12, 14, 25 3-Deoxo-3ß-hydroxyditerpenes, acylated Deuterium labelIed compounds 453 t-Butanol 12 3-Deoxo-3ß-hydroxyphorbol 408, 410, 411, Chloroform 76, 126, 397, 434, 443, 449, 416,417,428 568 -, -3,9,12,13,20-pentaacetate 411 Deuterium oxide 47, 397, 405, 406, 434 -, -9,12,13,20-tetraacetate 411 Dimethyl sulfoxide 434 -, -12,13,20-triacetate 411,428,429 Dopa 545, 550 3-Deoxo-3ß-hydroxy-4cx-phorbol 448 Dopamine 545 -, -3,12,13,20-tetraacetate 453 Exchange studies 250 -, -12,13,20-triacetate 448 Glykoside, perdeuteromethylierte 170 3-Deoxo-3ß-hydroxy-l ,~-dihydro-4cx­ Incorporation in penicillin D 11 phorbol448 Melanin 550,551 3-Deoxo-3ß-hydroxytiglophorbol-3,12,20- Methylaspartate 604 triacetate 433 Pyridine 405, 406, 434, 443 5'-Deoxyadenosine 591, 599, 600, 601, 602, Trichothecane derivatives 83 608 Diacetongalaktose 192 5' -Deoxyadenosyl radical 590 12ß, 13-Diacetoxy-4,9-dihydroxy-l ,6(20),7- 20-Deoxy-/X;, 7-dihydro-phorbol 420 tigliatrien-3-one 418 6-Deoxyhexose ->- L-Rhamnose 155, 166, Diacetylacetone 220, 221, 235, 237, 238, 170, 180, 184, 185 240,244,245,246 5'-Deoxyinosine 600 Di-O-acetyldihydroverrucarol 82 5' -Deoxyinosylcobalamin 600 Di-O-acetyl roridinic acid dimethyl ester 90 4-Deoxylumiphorbol-12, 13,20-triacetate -,ozonide 90 449,451 Di-O-acetyl-verrucarin A 74 20-Deoxy-20-oxophorbol Di-O-acetylverrucarol 65, 67, 74, 82, 83, -, -12,13-diacetate 416 107 -, -didecanoate 419,420 -, antifungal properties 112 -, -2,4-dinitro-5-iodophenylhydrazone 416 -, NMR-spectrum 76, 77 12-Deoxy-12-oxophorbol-13,20-diacetate Diacetylzucker in Glykosiden 176 416 1,3-Dialkylcyc1opentanones 290 -, -mono-2,4-dinitrophenylhydrazone 416 Dialysis 555, 611 4-Deoxyphorbol 450f, 453 1,4-Diaminobutane 104 -, -12,13-diesters 452 1,2-Diaminopropane 104 -, -esters 451,453 4,5 ;9, 10-Dianhydrophorbol-12, 13,20- -, -triacetate 418 tridecanoate 418 20-Deoxy-phorbol derivatives 418 Dianthus-Arten 188 4-Deoxy-4cx-phorbol 450f, 453, 454 Diarylmethane 244 -, -12,13-didecanoate 452 1,5-Diazabicyclo[4.3.0]non-5-ene ->- DBN -, -diesters 452, 454, 455 11, 13 -, -12,13,20-triacetate 445, 446, 449, 450, Diazoalkane 5,414,415 451 Diazo compounds 35 2' -Deoxyribonucleotides 600, 602 Diazoethane 414 20-Deoxy-l ,~,/X;, 7-tetrahydro-phorbo- Diazoketones 50 butanone 439 Diazomethane 14, 15, 17,36,52,80,81,86, 20-Deoxy-l,~,/X;, 7-tetrahydro-phorbol 419 97, 98, 180, 228, 232, 236, 249, 250, 332, -, -12,13-diacetate 419 414, 437, 536, 538, 545, 548, 549, 556, 20-Deoxy-tetrahydrophorbol-13-acetate 408 558,568 20-Deoxy-tetrahydrophorbol-12,13-diacetate Dibenzoyl-D-Weinsäure 473 408 7,4' -Dibenzyl-fiavonol-acetate 200 6-Deoxyversicolorin A 141, 142 7,4'-Dibenzyl-kämpferol 201 Desoxyajma1in 496 4',7-Dibenzyl-quercetin 201 Sachverzeichnis. Subject Index 661

Diborane 301 2,3-Dihydro-isoorientin 182 Dibromäthan 510 Dihydro-kämpferol-7-glucosid 199 Di-n-butyl ether 383,391,392 Dihydrokeyakinin ...... Keyakinol 181 3,5-Di-t-butyl-4-hydroxy-benzyl esters 4 Dihydrolipoate 597,600,601 ß-Dicarbonyl compounds, enamine derived Dihydro-O-methylsterigmatocystin 122, 123 from 4 -, synthesis 139 2,4-Dichlorophenyl malonate 239,240,241 Dihydronortluorocurarin 494 Dicotyledoneae 187,188 Dihydropentaketo diacid 269 2,3-Dicyano-5,6-dichloro-l ,4-benzoquinone Dihydropinosylvin 246 (DDQ) 329 Dihydropolyketides, syntheses with 267 N,N'-DicycJohexylcarbodiimide 3 Dihydropyrone 243, 266, 267 4' ,5' -Didehydro-5' -deoxyadenosine 591, Dihydrosterigmatocystin 126, 134 594,597,601,602 3-Dihydrotetra-acetic acid 242,243 3,13-Dideoxo-3, 13-dihydroxybisdehydro• 5-Dihydrotetra-acetic acid 242, 243 phorbol-3,12,20-triacetate 433 Dihydro-l,4-thiazin-3-one 15 12,20-Dideoxy-12-oxo-tetrahydrophorbol- Dihydroverrucarol 84, 96 13-monoacetate 408 Dihydro-ß-vetivol 316 Didymin -+ Atsinosid 160, 162, 165, 194 meso-Dihydro-ß-vetivone 318, 321,322 Dieckmann-Cyclisierung 498 2ß-13-Dihydroxy-~9 -apotrichothecenes 83 Diels-Alder addition 331 2,3-Dihydroxybutenal 589,590 Dien-Addition 331,488,502,513 Dihydroxychalkon-2'-0-glucosid 157,158 3,3-Diethoxypopyne, lithium salt 99 2',4'-Dihydroxy-chalkon-4' -glucosid 199 Diethyl carbonate 299 o-Dihydroxy-compounds, oxidation 530 Diethyl ether 16, 393 4 ß, 15-Dihydroxy-12, 13-epoxy- ~9 -trichothe• Diethyl ethoxymethylenemalonate 243 cene ...... verrucarol 78 Diethyl malonate 331, 332 Dihydroxy-flavone 194 Diglucoside 159 7,4-Dihydroxy-flavon-8-C-ß-D-glucopyrano• Diglucuronid 159 sid ...... Bayin 180 Diglyme 302 7,4' -Dihydroxyflavon-7-0-glucosid 197, 199 Dihalomethylmethyläther 191 5,6-Dihydroxyindole 524, 525, 526, 527, 529, 6,6-Dihalopenicillanic acids 14, 15 537,542,543,544,546,552,556,557,558, Dihydroacorenone 291 560,561,562,570 Dihydroatlatoxin-M 1 ...... Atlatoxin-M 2 132 -, -2-carboxylic acid 524,525, 550, 556, 558, Dihydroagarofuran 313,314 561 Dihydroagarospirol 311 -, -4,7-dicarboxylic acid 556 Dihydro-a.-alaskene 357 -, -glucuronoside 529 Dihydrocatharanthin 505 -, -sulphate 529 Dihydrochalkone 154 5,6-Dihydroxyindole-melanin 540, 543, 545, Dihydrochalkon-C-glucosid 182 546,554,556,557,567 Dihydrochalkon-C-glykoside 186, 197 5,6-Dihydroxyindoline 570 Dihydrochalkon-2' -O-mono-glucosid 157 7,4'-Dihydroxyisotlavon ...... Daidzein 157, Dihydrochalkon-neohesperidosid 164 181 Dihydrocorynanthein 472 2,4-Dihydroxyisophthalsäure 180 Dihydro-a.-curcumene 304, 305 5,2' -Dihydroxy-7-methoxy-flavon-2' -0- 2,3-Dihydrofuran 126,485 monoglucosid -+ Echioidin 202 Dihydrofuran ring 141 5, 7-Dihydroxy-4' -methoxy-isoflavon-7-0- Dihydrofuro[2,3-bJbenzofuran 132. 133. apioglucosid ...... Lanceolarin 169 147 3,8-Dihydroxy-l-methoxyxanthone 124, 125 Dihydrofurofuran function, formation 144 7-4' -Dihydroxy-3' -methoxy-flavon-7-0-glu• Dihydrohinesol 318,363 cosid 197 Dihydro-5-hydroxysterigmatocystin 126, (2S,3R)-2,5-Dihydroxy~3-methyl-valeric 146 acid 85 Dihydroindane 238 1,8-Dihydroxynaphthalene 537,538 662 Sachverzeichnis. Subject Index

3,4-Dihydroxyphenethylamine -+ Dopamine 5,7-Dimethyl-epiorientin 180 522,543,544,545,560,567,568,569,570 Dimethyl-2'3' -epoxy-2' -anhydro-roridinate, 3,4-Dihydroxyphenylalanine -+ Dopa 522, NMR 76,77 523,524,525,526,527,528,529,530,531, Dimethyl formamide 15, 17, 160, 199, 202, 532,539,543,545,546,547,548,550,551, 257,412,413,414,415,448 552,553,554,558,559,560,561,562,564, Dimethyl hexahydromyrothecinate 98 567,574 Dimethylhydroazulenones 320 6,7-Dihydroxy-phorbol-12,13-diacetate 420 2,3-Dimethylindole-5,6-quinone 527 -, -4,9,12,13,20-pentaacetate 421 4,7-Dimethyl-2-isopropyl-5-indanol 316 -, 12,13,20-triacetate 420 1,7-Dimethyl-4-isopropylnaphthalene 286 6,6-Diiodopenicillanic acid 14 7,3' -Di-O-methylluteolin-4' -O-apioglucosid Di-isobutyl-aluminium hydride 136 -+ Homoflavoyadorinin B 169 Di-isopentyl-borane 135, 140 5-0-Methyl-orientin -+ Parkinsonin A 180 Diisopropylamine 228 Dimethylmaleate 605 N ,N'- Diisopropylhydrazine, amides of 4 Dimethylmercury 617,618 1,2,3,5-Di-isopropyliden-cx-D-glucofuranose Dimethyl3-methylglutarate 98 -+ Isodiacetonglucose 192 Dimethyl-myrothecinate 76, 77 3,5-Diketo acids 246 4', 7-Di-O-methyl-orientin-(6-0-acetyl)-O• -, syntheses 227f rhamnosid -+ Linosid B 184,186 3,5-Diketo esters, syntheses 227f 4',7-Di-O-methyl-orientin-O-rhamnosid -+ ß-Diketones 227,228,235 Linosid A 184, 186 -, acylation 230 (2S,5 R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenyl• Diketo thiolacids 228 acetamido)-4-thia-l-azabicycJo[3.2.0]• Dilithio-acetylacetone 228 heptane-2-carboxylic acid 3 Dilithio-diketones 230 3,4-Dimethylphenol 531 5,7-Dimethoxy-coumarin 129 2,2-Dimethyl-6 ß-phenylacetamidopenam- . 5,7-Dimethoxy-cycJo-penteno[c]courmarin 3cx-carboxylic acid 3 129 Di-O-methyl-4cx-phorbol-12,20-diacetate 448 5,7-Dimethoxy-cyclo-pentenone-coumarin 4, 13-Di-O-methylphorbol-12,20-diacetate 130 415 Dimethoxy-flavonole 156 4,20-Di-O-methylphorbol-12,13-diacetate 5,6-Dimethoxyindoline 568 415 3,4-Dimethoxyphenetylamine 568 2,6-Dimethyl-4-pyrone 220,221,226 Dimethyl acetonedicarboxylate 244 7,4' -Dimethyl-quercetin-3-rutinosid -+ Om- 6-Dimethylaminopenicillanic acid 11 buosid 162 Dimethyl-2' -anhydrororidinate 76,77 Dimethylroridinate, NMR 76, 77 4'-7-Di-O-methylapigenin-6-C-(xx' -di-O• Dimethylspiro[4.5]decanones, synthesis 342 rhamnosyl)-ß-D-glucopyranosid -+ Embi• Dimethyl sulfate 138, 473 nin 184 Dimethyl sulfoxide 10, 16,41,330,331,335, Dimethylarsine 616,617 364,414,415,434,502,515 7,4'-Di-O-methylbayin 206 Dimethyl tetrahydrororidinate 92 7,12-Dimethylbenz[a]anthracene (DMBA) Dimethyltetraketone 235, 259 384,386,390 2,4-Dinitrobenzaldehyde 97,98 5,6-Dimethylbenzimidazole 601,618 3,5-Dinitrobenzoic acid chloride 397 cx( 5,6-Dimethylbenzimidazolyl)-Co-5-deoxy- Dinitrogen monoxide 597,600,602 adenosylcobamide -+ Coenzyme B12 583f 2,4-Dinitrophenol, esters 3 Dimethyl carbonate 228, 232, 333 2,4-Dinitrophenylhydrazine 6,97,98 Dimethylcatechol 531 2,4-Dinitrophenylhydrazones 416 N ,N-Dimethylchloroformiminium chloride 3 -, of aldehydes from croton oil 393 2,6-Dimethylcyclohexanone 312 Dioldehydrases 592f, 599, 600, 602, 608 2,6-Dimethylcyclohexenone 368 Diosma-Arten 160 2,3-Dimethyl-5,6-dihydroxy-indole 527 Diosmetin 156, 157, 160, 161 Dimethyl-5,6-dihydroxy-indole 542 -, -di-C-glykoside 185 Sachverzeichnis. Subject Index 663

Diosmetin-6-C-glucosid 178, 180 Eburnamin 512 -, -8-C-glucosid 178,180 Eburnamonin 513 -, -glucuronid 173 Eburna-Reihe der Indolalkaloide 512 -, -7-0-monoglucosid 195 Echioidin 202 -, -7-0-rutinosid 160,162 Egyptian mummies 565 Dioxane 66,67,70,83,381,407,428,431 Ehrlich ascites tumor 113 o-Diphenols 530,531,537,544 Einschlußverbindungen mit Jod 186 -, oxidation 523 Elbs persulphate reaction 126 Diphenyl ether linkage, formation 139 Electron microscopy 529 Diphenyl ketone 106 Electron spin resonance spectra Diphenyltetraketone 234, 235, 259, 260 Cobaloximes 589,601 Dipsacaceae 186, 188 Ethanolamine desaminase 598 Dipsacus-Arten 188 Glycerol dehydrase 598, 601 Dipyranopyrantrione 237,238,239,261,263 Melanins 563, 564, 565 Dipyrones 238, 240, 263, 265 Ribonuc1eotide reductase 598,601 -, aromatization 264 Vitamin B12 589 Dirhamnosid 159 E1ectrophoresis of sepiomelanoprotein 555 Disaccharide in Flavonoid-glykosiden 159 E1eutherinol, dimethyl ether 244, 245, 271 Disiamylborane-hydrogen peroxide 334 ß-Elimination, base induced 594 Disulfides 43 Elisanthe-Arten 188 Diterpene esters in croton oil 444, 454 f Embigenin -+ 4',7-Di-O-methyl-saponacetin -, biological activity 455f 180 Diterpenes in croton oil 444, 454f Embinin 180, 184 -, biological activity 455f Embryotoxic affect 113 Dithioerythritol 600,615 Emodin 244,245 Dithiols 597,600,601,602,611,617 Emulsin 167 DMBA s. Dimethylbenzanthracene Endocrocin 225, 244 DNA, doubling 113 Endoperoxide group 144 Dodecanoic acid 395 Enol ethers, IR spectra 250 Dogs 113 ö-Enollactones 246 Dolichandrone falcata 161 Entbenzylierung, katalytische 201 Dopa s. 3,4-Dihydroxyphenylalanine Enzymatic reactions, corrin dependent 610f Dopachrome 525,526,527,552,556,557,558 Enzymes for polyketide synthesis 227 Dopa-Melanin 540f, 545, 546, 548, 549f, 554, Enzymes for synthesis of aromatic metabo- 555,556,557,562,563,567,569 lites 226 -, autoxidative 542, 549, 550, 551, 552 Enzymes in melanogenesis 530f -, enzymic 549, 550, 552 Enzymhydrolyse 156,165,167,168,169 -, methylated 547,548 Enzymic dopa-melanin 542 Dopamine -+ 3,4-Dihydroxyphenethylamine Enzymic hydroxylation 531 522,543,544,545,560,567,568,569, 19-Epi-ajmalicin 482 570 6-Epi-aminopenicillanic acid 6,7,13 Dopamine-Melanin 543, 567 -, methoxymethyl esters 14 Dopaminequinone 569 Epieburnamonin 513 Dopa oxidase 528, 530, 567 2-Epi-cx-cedrene 295,301,304,305,348 Dopaquinone 525, 526, 530, 559, 560, 571, Epidermal hyperplasia in mice 380 573,574 4,10-Epieudesmanes 342,343,345,346,350, Dopa semiquinone 564 351 Dothistromapini 147 -, intermediates 344 Dothistromin 147 Epi-y-eudesmols 343 Double sulfoxide rearrangement 31 6-Epihetacillin 6,7,11, 12, 13 Douglastanne 202 Epihinesol 333 Ducks 120 Epi-ibogamin 516 Dufour-Reaktion 186 Epimerization 250 664 Sachverzeichnis. Subject Index

Epimerization of sulfoxides 28 Ethyl acetylpyruvate 72 Epi-N-Methyl-rhynchophyllan 475 Ethylacrylate 606, 607 Epinephrine -+ Adrenaline 559,560,565,566, Ethylamine 333,341,365 567 Ethylarsines 616,617 Epinephrine-like compounds 528 Ethyl benzoylacetate 238,239,240,241 Epi-orientin 178, 180 Ethyl (X-bromoisobutyrate 334 -, -tetramethyläther 180 Ethylcobalamin 616,617 6-Epipenicillin G 13 Ethylcobaloxime 617 6-Epipenicillins 9, 13 Ethyldiisopropyl amine 19 Episulfonium ion 28 Ethylene chloride 65 Epi-ulein 490, 492 Ethylene dithiol 368 Epi-ß-vetivone 334, 336 Ethylene glycol 299,332,367,592,599 -, synthesis 335, 364 Ethylene oxide 41, 331 3-Epiyohimbin 486 Ethyl orsellinate 252, 255 Epoxidation 107,109, 110 Ethyl oxalate 234 2,3-Epoxy-anhydromevalonic acid 107 12-0-Ethyl-phorbol-20-tritylether 417 2',3',-Epoxy-2'-anhydrororidinic acid 94 13-0-Ethyl-phorbol-20-tritylether 417 12,13-Epoxy-trichothecenes 75,83, 110 Ethyl-proline 562 -, mass spectra 83 Ethyl sodiobenzoylacetate 236 -, rearrangement 81,83 p,Ethyltoluene 287 12,13-Epoxy-trichoth-9-ene 110 Eucalyptus 226 Erbsenblätter 175 Eucalyptus hemiphloia 181, 189 Eremophilane 345, 352 Eudalene 309 Ergosterol 66, 68 Eudalin s. Eudalene -, thin layer chromatography 101 Eudesmane-nootkatane biogenetic Ergotism 120 conversion 370 Ericaceae 176, 188 Eudesmanes 345,351 Eriocitrin 160,163,165,195,198 ß-Eudesmol 344,346 Eriodendrum anfractuosum 160 Eugenol-glykosid 169 Eriodictyol 157, 158, 160, 161 Eumelanins 522,523,529,539, 540f, 553, 561, -, Benzylderivat 195 562,562,563,570,571,575 -, -7-0-neohesperidosid 161 -, natural 554f -, -7-0-rutinosid 160 Euonymus-Arten 203 Eriphorum-Arten 190 Euonymus lanceifolia 171 Erythema formation 379 Euphorbiaceae 188,378,380 Erythritol 592 Erythrocytes 379 Fabaceae 174, 188 Erythrose 221 Fagaceae 189 Escherichia coU 112, 618, 621 Fagopyrum-Arten 162 Essigsäure s. acetic acid Fagus-Arten 167 Essigsäureanhydrid s. acetic anhydride Fagus silvatica 175 Estrogenic hormones 455 Farnesol 284, 304 Ethane dithiol 131,291 -, pyrophosphate 109 Ethanol s. Äthanol Farn-Pflanzen 187 Ethanolamine 598 Fattyacids 218,225 Ethanolamine deaminase 593, 598f, 602, 608 -, biosynthesis 222, 226 Ethanolamine ammonialyase s. Ethanolamine -, of croton oil 380 deaminase F atty alcohols, long chain, NPAD ethers 398 Ethanolysis 228, 255 Fehling's reagent 404,408,416,417,431,433 Ether 101,386,387,404,420,421,440,524 Ferricyanide solution 526 Ethylacetate 65, 101, 138, 173,400,404,414, Ferrirhodin 89 415,417,445 Feru1oy1g1ucosen 175 Ethyl acetoacetate 219,244 Fischer-Synthese 489,507 Sachverzeichnis. Subject Index 665

FL-I060 4 Flavonoid-Glykoside, Tri-O-glykoside 169f Flaschenträger reaction 440, 443 -,O-Trioside 169f Flavanoid metabolites, degradation 246 -, Verbreitungen 186 Flavanone 154,158 Flavonole 154,156,158 -, Cotton-Effekt 165 -, benzylierte 200 -,2,3-Dihydroverbindungen 162 -, -glucosylrutinosid 170 -, -5,7-diglykoside 196 -, -glucuronide 173, 175 -, -C-glykoside 181 -, -glykoside 154,158,165,167,171 -, -5-0-g1ykoside 202 -, -glykosid-Vollacetale 203 -, -5-0-glykoside-Vollacetate 195 -, -7-0-glykoside 198,199 -, -7-0-g1ykoside 194,195,197,199 -, -tetraglykoside 171 -, -glykoside 158,195 4' -Fluoroadenosine 597 -, Glykosidierung 194 4' -Fluoro-deoxyadenosylcobalamin 597 -, -7-0-neohesperidoside 160[' 164, 194, 197 Foeniculin 156 -, Optische Aktivität 165 Foeniculum vulgare 156 -, -7-0-rutinoside 160f. 162, 164, 194 Fontanella-Arten 161 -, -tri glykosid 204 Fontanella crassi/olia 161 Flavanones 255 Formaldehyde 72, 104,311,470,610,620,621 Flavanonol-Glykoside 154 Formate 335,610 Flavanonol-Verbindungen 199 Formic acid 125,294,300,304,307,318,325, Flavasperone 224 351,365,370,427,470 Flaviolin 270, 271 -, ester 287, 329,471,476,482 Flavone 154,157,244 Fomosanin 482 -, -Diglykoside 185 Formylacetic acid 243 -, -C-glucosid 180 N-Formyl-D-penicillamine 21 -, -glucuronide 174 Fortunellin 161,164,195 -, -8-C-glykoside 205, 206 Fraxinus-Arten 167 -, -5-0-g1ycoside 202 Fungi 112, 120 -, -7-0-g1ykoside 195,196,197,200 -, human pathogenic 112 -, Glykosidierung 194 -, imperfecti 64 -, -monoside 156 2-Furaldehyde, esters of (E)-oximes 4, 6 -, -7-0-neohesperidoside 160f Furanoide Form 155 -, -7-0-rutinoside 160f, 162 Fusarium sp. 74 Flavonoide, 7-0-acylderivate 201 Fusigenin 89 Flavonoide, benzoylierte 201 Flavonoide, O-benzylierte 204 Gabriel-Synthese 516 Flavonoid-Glykosid.: 153f Gaillardia pulchella 187 -, Acyl-O-glykosidc 174f O-ß-D-Galaktopyranosyl-(I-+ 6)-O-a-L- -, Apiobioside 16~, 169 rhamnopyranosyl-(1-+ 3)-a-L-rhamno• -, O-Bioside 159f pyranose 172 -,O-Bisglykoside 203f O-ß-D-Galaktopyranosyl-(1-+6)-O-a-L• -, Di-C-glykoside 184f,203f rhamnopyranosyl-(1-+4)-a-L-rhamno• -, Disaccharide 159 pyranose -+ Rhamninose 170, 172 -, Glucuronide 173 D-Galaktose 155,170 -, C-Glucoside 177f,204f Galaktosyl-arabinose 159 -, Glykosidierungsmuster 153f Galaktosyl-galaktose 159 -, O-Glykuronide 173 Galaktosyl-7 -glucosid 159 -, Heteroside 170 Galaktosyl-glucosyl-glucose 172 -, makrocyclische 176 Galaktosyl-rhamnose 159 -,O-Monoside 155f Galaktosyl-7 -rhamnosid 159 -, Polysaccharid 173 Galaktosyl-xylosyl-glucose 172 -, Strukturtypen 153f D-Galakturonsäure 155, 173 -, Synthese 19lf Galanthus nivalis 167 666 Sachverzeichnis. Subject Index

Gallophaeomelanin fractions 571,572,574 hydroxy-dihydrochalkon -+ Aspalathin Gardenia 64 182 Gaschromatographie O-ß-D-Glucopyranosyl-(I-+ 3)-O-(X-L• Agarospirol derivatives 311 rhamnopyranosyl-(I-+ 3)-(X-L-gluco• Croton oil factors 401,402 pyranose -+ 2'-Rhamnosyl-Iaminaribiose Hinesol isomers 339,340 172 Gas-liquid chromatography 2-0-(ß-D-glucopyranosyluronsäure)-ß-D- Croton oil factors 383, 389, 391 glucuronsäure 159 Long chain fatty acids 395 D-Glucose 65,155, 157, 169,170,180,181,185 Methyl esters of fatty acids 383 Glucosidacetate 179 Roridin C 102 ß-Glucosidase-Spaltung 171, 175, 176 Sesquiterpene alcohols 102 C-Glucosidierung 204 Trichothecanes 102 Glucosyl-arabinose 159 Verrucarol 102 3-Glucosyl-7-arabinosid 159 Gastroenteritis 379 Glucosyl-glucopyranosyluronsäure 159 Gaultheria-Blätter, Fermentpräparat 168 Glucosyl-glucosyl-glucose 172 Gein 169 3-Glucosyl-7-rhamnosid 159 Geissoschizin 471 Glucosyl-rhamnosyl-xylose 172 Geissoschizolin 494 26 -Glucosylrutinose 172 Gelfiltration 538 36 -Glucosylrutinose 172 Genista pi/osa 188 D-Glucuronsäure 155,173,174 Genistein 157 Glutacondialdehyde 428,429,430 -, Benzylderivat 202 Glutaconester 470 -, -4' -glykosid 202 Glutamate 603, 604 -, -4'-O-neohesperidosid 165,201 Glutamate mutase 593,603f -, -7-0-rhamnoglucosid 163 D,L-Glutamic acid 102 Genistin-+ 5, 7,4' -Hydroxyisoflavon-7-0- Glutathione 553 monoglucosid 194 Glutarimide 312 Gentianaceae 189 Glutinosin 64 Gentiobiose 159,166, 167, 169 Glycerin 185,404,444,445 -, -acetat 193 Glycerol s. Glycerin Gentiotriose 169, 172 Glycerol dehydrase 592,593,598,601 Gentiotrioside 171 Glycidester-Kondensation 483 [2-3Hl-Geranyl phosphate 110 Glycidic acids 107 [2-3 H,2-14C]-Geranyl pyrophosphate 109 Glycine 102,557,558,604 Gesneriaceae 189 Glycol derivatives 594 Geum urbanum 169 Glycolysis 113 Glaucophanic acid 242, 243 Glycosides 539 Glaucophanic enol 268, 269 Glykoside, Acetylzuckerkomponenten 176 2-0-(ß-D-Glucopyranosyl)-glucopyranose -+ Glykoside, perdeuteromethylierte 170 Sophorose 159,166,167,170,171,175,192 C-Glykoside, Vorkommen im Pflanzenreich 6-0-(ß-D-Glucopyranosyl)-glucopyranose -+ 187 Gentiobiose 159, 166, 167, 169 Glykuronsäuren, glykosidisch gebundene 173 O-ß-D-Glucopyranosyl-( 1-+6)-O-ß-D-gluco• Glyoxal 48 pyranosyl-( 1-+2)-(X- L-rhamnopyranose-+ Gnidia-Art 175 26 -Glucosylrutinose 172 Gossypetin-Glykoside 156 O-ß-D-Glucopyranosyl-( 1-+ 2)-O-ß-D-gluco• Gossypium barbadense 167 syl-(1-+2)-ß-D-glucopyranose -+ Sopho• Gossypium herbaceum 200 rotriose 172 Gramineen 186 O-ß-D-Glucopyranosyl-(1 ...... 6)-O-ß-D-gluco• Gram-negative bacteria 112 syl-(1-+6)-ß-D-glucopyranose -+ Gentio• Gram-negative organisms, activity against 4 triose 172 Gram-positive bacteria 112 3' -ß-D-Glucopyranosyl-3,4,2',4' ,6' -penta- Gratida officinalis 190 Sachverzeichnis. Subject Index 667

Graveobiosid A 168 Hexahydro-2'-anhydrororidinic acid 96 Graveobiosid B 169 Hexahydromyrothecinic acid 96, 97 Grignardierung von subst. Benzol 206 Hexahydrororidin A 90 Grignard reagents 585,615 Hexahydroverrucarin A 84 Grignard-Reaktion 502,509,516 Hexaketide chain, undegraded 264 Griseofulvin 224, 225 Hexaketo acids 271 Griseophenone C 272, 273 1,3,5,7,9,1 I-Hexaketones, synthesis 239, 271 Ground nut (pea nut) 120 Hexose 221,222 Grünalgen 185 Hibiscus-Arten 189 Guajaverin 155, 156 Hibiscus mutabilis 167 Guajazulene 428 Hinesane 345,362 Guanidin hydrochloride 598 Hineso1 316,317,318,324,325,326,327,328, Gymnospermae 187 330,336,338,344,346,363 -, -acetate 340 Haferkeimlinge 186 -, p-bromopheny1urethane derivative 336 Hakamori-Permethylierung von Glykosiden -, degradation 319 173 -, oxidation 320 Halogenzucker 196,203,204 -, synthesis 338f, 345, 366f -, acetate 198 Hippophae' rhamnoides 162 6-Halopenicillanic acids 13 Hippuric acid 21 Hamster melanoma 531 Hofmann-Abbau 502, 509 Harding-Passey mouse melanoma 529, 554, Homoallyl rearrangement 418,437 558 Homocephem derivative 40 Helenium-Arten 187 Homocysteine 618,619 Helferich-Zirner-Methode 191, 192, 193 Homoflavoyadorinin B 169 Heliantheae 157 Homoorientin 178 Helichrysin ~ Salipurposid 165, 202, 203 Hordeum-Arten 191 Helichrysum arenarium 203 Hordeum vulgare 182 Helicobasidin 110 Horeau method 70 Helleborus foetidus 176 Horseradish peroxidase 532 Helleborus niger 167 Howeaforsteriana 190 Hemiphloin 181, 182 Huang-Minlon-Reduktion 516 Hemolysis 379 Hudson-Klyne-rule 155,288 Hepaticae 187 Humulus japonicus 189 Hepatocarcinogen 120 Humulus lupulus 165 Heptaacetic acid 224, 240 Hydridocobalamin 586, 610 -, natural derivatives 226 Hydridocobaloxime 606 ß-Heptacarbonyl compounds 239f, 264 Hydridocorrin 610 Heptaketo diacid 241,265 Hydrierung s. hydrogenation Heptaketones 239,264 Hydroazulenes 284,318 Heptene-2,6-dione 242 Hydroazu1enols 320 Herniaria glabra 162 Hydroazulenone 342 Herpex simplex 112 Hydroborierung 517 Hesperetin 157,158,160,161,165 Hydrobromination 420 -, -7-0-neohesperidosid 161 Hydroformylation 607 -, -7-0-rutinosid 160 Hydrofuro[2,3-b]benzofuran structure 141, Hesperidin 160, 162, 165, 194 147 Hetacillin 5, 10, 11, 12 -, bio genesis 142 -, -sulfoxide 30 Hydrogenation 5,7,8,13,14,16,18,51,71,75, Heterocyclic c10sures 223 79,84,89,90,95,96,97,98, 114,124, 128, Hexaacetic acid derivatives 238 131, 132, 133, 134, 135, 136, 138, 164, 168, Hexaacetic acid, protected 263 203,243,291,292,293,295,302,303,309, Hexaacetyl-salipurposid 203 311,316,318,320,322,323,324,328,329, 668 Sachverzeichnis. Subject Index

337,338,342,351,408,419,420,437,439, 7-Hydroxyflavonol-monoglykosidacetat 203 473,478,479,482,486,492,495,500,513, Hydroxylamine 92 537,556 2-Hydroxy-5-methyl benzoic acid 69 Hydrogen bromide 109, 192, 420, 421, Hydroxymethylene derivative 329 517 5-Hydroxy-3-methyl-2-pentenoic acid 89 Hydrogen chloride 13, 14, 15,30,50,65,75, -, lactone 73, 89 81,90,92,97,98,102,135,174,196,200, 6-Hydroxymusizin 224, 270, 271 201,204,220,221,251,252,260,294,300, 5-Hydroxy-2-oxo-3-methyl-valerolactone 73 337,367,404,440,536,538,543,547,549, 3-Hydroxypenam system 38 550,555,556,558,561,567,568 6-Hydroxypenicillanic acid 16 Hydrogen fluoride 247 8-Hydroxypenillic acid 23 Hydrogen iodide 274 Hydroxyphorbobutanone 442 Hydrogenolysis 14,15,71,180,204,272,341, -, -20-acetate 442,443 364,419,502,510 Hydroxyphorboisobutanone-9,13-semiketal- -, ofphenolic hydroyl groups 225 20-acetate 410,442,443 Hydrogenolytische Entbenzylierung 201 Hydroxyphorbolactone-semiacetal 433, 435 Hydrogen peroxide 24, 69, 90, 126, 174, 175, 6-ß-Hydroxyphorbol-7ß,9,12ß,13,20-penta• 199,416,510,523,532,536,539,544,545, acetate 421 546,548,558,565,568 4-Hydroxypyrano[4,3-b]pyran-2,5-diones Hydrogen sulfide 43 234,252 Hydrogen transfer 110 4-Hydroxy-2-pyrones 228, 229, 234, 246 Hydrolysis 72,73,74,84,86,88,89,90,94,95, Hydroxyquinol 533, 535 96,98,99,107,136,137,138,139,155,162, Hydroxy-p-quinone 533, 535 1~1~1~1~1~1~1~1~1~ Hydroxyzimtsäurezuckerester, natürlich vor- 184,191,200,202,203,204,234,252,259, kommende 175 307,312,329,331,332,334,366,368,383, Hymenophytum flabellatum 187 413,420,437,455,481,482,483,494,516, Hyperosid 156 538,555,559,567,585,609 Hypochlorit-Oxidation 482, 504 Hydronaphthalenic sesquiterpenes 342f Hyssopus officinalis 160 Hydroxocobalamin 584,587,589,601 2-Hydroxy-acetophenon-C-glykosid 206 Ibogain 513 2-Hydroxyalkyl-cobaloximes 594 Ibogamin 513,516,517,518 Hydroxybenzaldehyd 203 Iboga-Typ von Indolalkaloiden 513,514 -, -glucopyranosid 204 Imidazole 620 p-Hydroxy-benzoyl-vitexin 184 Imidazolide 232 -, Hepta-O-acetyl-Derivat 184 Imidazolidinone structure 5 -, Hepta-O-methyl-Derivat 184 Indanes 238 Hydroxybisdehydrophorbol-semiketal 432 Indanol 322 -, 12,13,20-triacetate 434 Indolalkaloide 469 f. 2' -Hydroxy-chalkonglykoside 198 Indole 540 3-Hydroxy-4 3. 5-cholestadien-7-one 430 Indolenin 494 Hydroxy-cumaran-3-one 198 Indole-5,6-quinone 525,526, 527, 541, 545, 6-Hydroxy-cumaranon-6-ß-D-glucosid- 548,552,553,559,560,567 tetraacetat 198 -, -2-carboxylic acid 559 5-Hydroxy-dihydrosterigmatocystin 126,146 -, polymers 540, 555 5-Hydroxy-2,3-epoxy-3-methyl-valerolac• Indole, urinary 529 tone 73 Indolinecarboxylic acid 549 4-ß-Hydroxy-12, 13-epoxy- 4 9 -trichothecene ß-Indolyl-äthylbromid 479,481 -- Roridin C 78 Indolyl-benzoquinones 526 Hydroxyethylate anion 594 Indolylessigsäure 502 Hydroxyethy1coba1oximes 594 -, -anhydrid 517 Hydroxyethylcobinamide 594 -, -ch1orid 496,514 7-Hydroxyflavonol-diglykosidacetat 203 Indolylquinones 540 Sachverzeichnis. Subject Index 669

Infrared spectra Irritant activity 383, 388, 390, 391, 392, 398, Acorane 293 399,401,402,427,452,455 Acorenone 291 Irritant dose 50 384,401 Acorolone derivatives 285 Irritant unit 383, 399, 400 Acorone 285 -, determination 384 Acoronol 288 IR-spectra s. infrared-spectra Aflatoxin BI 130, 132 Isoacoradiene 286 Aflatoxin GI 131 Isoacorone 285,286,287,288,289,292,294, Aflatoxin MI 132 295,354,355,356,359 Agarospirol derivatives 309, 311, 3-Iso-ajmalicin 482 312 p-Isobutyltoluene 287 Alaskene 293 Isocalamenene 294,295,296 Aspertoxin 128 Isocoumarin 271 Biochanin-A-glykosid 176 Isodiacetonglucose 192 Croton oil factors 396f,427 Isoelectric point 6 Dihydro-ß-vetivone 321 Isoembigenin 178,180 5,7-Dimethoxycyclopentenone-coumarin Isoflavone 154,155,157 130 -, Glykoside 156,165 Enol ethers 250 -, Glykosidierung 194 Hinesol 326 -, Monoside 156 Isovetivane 317 -, Rhamnoglucoside 162 ß-Lactam carbonyl 45 Isoguanine-D-riboside -+ Crotonoside 378 Melanins 562 Isohemiphloin 181,182 -, benzoylated 567,568 Isoorientin 178 -, methylated 568 -, -O-arabinosid 184 Myrochromanol 69 -, 14C-Iabelled 186 Myrochromanone 69 -, -7-0-glucosid -+ Lutonarin 182, 187 Phorbo1405 -, -7'-O-methyläther 180 -, derivatives 424, 425, 427 -, -7-0-rutinosid -+ Wyomin 182 Roridin E 95 -, Xylosylderivat 184 Selinane 309 1.lo-Isophorbol 447,451,452,454 Sterigmatocystin 124 -, -12,13,20-triacetate 445,446 Tetrahydrodeoxo-aflatoxin-B 1 129 Isoporiolid 176, 177 Verrucarin A 84 Isoprenoidmoietyin verrucarinsandroridins 111 Verrucarin B 88 Isopropenyl acetate 237 Verrucarinolactone 84 Isopropenyl-isopropylidene-isomerization 442 Verrucarol 75 Isopropenylmagnesium bromide 306, 341 Vetivane 317 Isopropyl alcohol 411 Vetivone degradation product 321 2-Isopropylidene-l,4-dichlorobutane 340 Insecticidal activity 113 Isoquercetin-Monoglykoside 156 Inverse octant rule 408 Isoquercitrin 156, 169 Invertebrates 524, 529 Isoquinoline alkaloids 221 Iodide ion, nuc1eophilic reactivity 588 3-Isoreserpin 488 Iodine 47,48,101,195,420 Isorhamnetin 158,201 Iodobenzene dichloride 42 -, -3,7-diglucosid 203 Iodoform reaction 90 -, -3-glykoside 201 Ion-exchange chromatography 571 -, -3-rutinosid 162,201 Iridaceae 190 Isorhoifolin 160, 195 Iris-Arten 190 Isosakuranetin -+ Citrofoliol 157, 158, 160, Iris germanica 180 161, 162 Iron 538 -, -7-0-neohesperidosid 161 -, binding by eumelanins 554 -, -7-0-rhamno-glucosid 162 Iron pentacarbonyl 367,368 -, -7-0-rutinosid 160 670 Sachverzeichnis. Subject Index

Isosalipurposid -+ 2'4'6'4-Tetrahydroxy• Kämpferol-3-0-ß-D-glucosid 169 chalkon-2' -O-glucosid 202, 203 -, -7-glucosid -+ Populnin 199 Isosaponarin -+ Saponaretin-4' -O-glucosid -, -glucuronid 173,201 182 -, Glykoside 166 Isosarothanosid 161,165,194 -, 3-0-glykoside 167, 201 Isoscoparin -+ 3'-Methyl-Iutonarin 178, 180 -, Monoglykoside 156 -, -7-0-glucosid 180 -, -7-0-neohesperidosid 199 Iso-sterigmatocystin 125, 126 -, -3-0-(p-oxybenzoyl)-glucosid 176 -, -di-O-methyl ether 125 -, -3-0-rhamnodiglucosid 170,171 Isostrychnin 500 -, -3-rhamnogalactosid 166 Isoswertisin 178 -, -3-0-ß-D-[cx-L-rhamnopyranosyl-(1-+3)]- -, -4' -O-glucosid 182 D-glucopyranosid 165 Isovelbanamin 505 -, -3-0-rhamnosid 165,166 Isovetivane 317,318,327,328,362 -, -7-0-rhamnosyl-3-0-xylosyl-galactosid Isovetivene 318, 326, 328 168 cx-Isovetivene 361, 362 -, -3-rutinosid 162 cx-Isovetivenene 316,317,328,361 -, -3-0-sophorosid 167 ß-Isovetivenene 316, 317, 361 -, -3-0-sophorosyl-7-glucosid 167 -, synthesis 366f -, -3-0-(triglucosidyl)-p-cumarat 175 Isoviolanthin 185,205 -, -xylosyl-glucoside 167 Isovitexin -+ Saponaretin 178, 179, 181, 186 Karplus equation 409 Itaconate 605 Ketal 236 Ketenes 257,258 Jacein 194 -,dimer 244 Jatropha gossypifolia 188 -, polymers 221 Jod s. Iodine ß-Ketoaldehydes 243 Jodessigester 513 cx-Ketobutyricacid 90,91 Jodierung 195 Keto-dipyrone 269 Jod-Jodkalium 186 ß-Keto esters 228,235,237,244,257 Jonesreagent 38,338 Keyakinin -+ 7-0-Methyl-kämpferol-6-C-ß- Juglans-Arten 167 D-glucosid 181 Juniperus rigida 292, 294, 355, 356, 359 Keyakinol-+ Dihydrokeyakinin 181 Juniperus sp. 293,347 Khumisol 346 Juniperus virginiana 355 Khumisyl p-bromobenzoate 346 Kidney beans 64 Kaliumacetat s. Potassium acetate Klyne-Regel 155 Kalium-acetylid 491 Kohlensäuredimethylester 510 Kalium-bicarbonat s. Potassium hydrogen cx- Kojibioseoctaacetat 183 carbonate Kolkwitzia amabilis 160 Kaliumhydroxid s. Potassium hydroxide Königs-Knorr-Synthese 193, 195, 198, 199, Kalium-permangant s. Potassium permanga- 201,203,204 nate Konproportionierung 200 Kalium-t-butylat s. Potassium t-butoxide Korte-Umlagerung 476,482 Kämpferol 156 Krebs-Ringer solution 113 -, -3-0-(benzoyl)-glucosid 176 Kuhn-Roth-oxidation 102 -, -4' -O-p-cumaroylarabinosid 175 -, -4' -O-p-cumaroyl-3-diglucosid 175 Labat test for methylenedioxy groups 546, -, -3-(p-cumaroylglucosid) 174,175 556 -, 3-0-feruloyl-sophorosid 175 Laburnum anagyroides 189 -, -gentiobiosid 167 ß-Lactamase enzymes 23 -, -3-0-ß-D-glucopyranosyl-(I-+ 3)-O-cx-L- ß-Lactam opening 6, 20 rhamnopyranosyl-(I-+2)-D-glucopyrano• ß-Lactam ring ofpenicillins 3 sid 171 Lactobacillus acidophi/us 85, 600 Sachverzeichnis. Subject Index 671

Lactobacillus leichmannii 593, 598, 600 Linum maritimum 184 Lactobacillus sp. 592, 593 Lipase 379 Lactoperoxidase 532 Lipids of croton seeds 379 Lamiaceae 173, 174 Lipofuscin 567 Laminariobiose 171 Liquid-liquid partition Lanceolarin -+ 5,7-Dihydroxy-4' -methoxy- Croton oil fractions 381,403 isoflavon-7-0-apio-glucosid 169 Roridins 65 Lanosterol 99 Verrucarins 65 Laretia acaulis 187 Liquiritigenin 157,158, 165 Larix laric.ina 187 -, -O-glucosid 157 Lathyrus vernus 188 Liquorice 539 Latyrose-+2-0-(ß-D-Xylopyranosyl)-ß-D- Lithio cyc1opropyl phenyl sulfide 368, 369 galactopyranose 159, 167, 168, 171 Lithium 299, 329, 330, 333, 341, 342, 365, Latyrus odoratus 168 367,491 Lead dioxide 417, 431 Lithium-acetylid 491 Lead tetraacetate 75,81, 179,408,410,417, Lithiumalanat s. Lithium aluminium hy• 428,431,432,434,435,436,441,482,516 dride Lebermoos -+ Monocleafosteri 173 Lithium aluminium hydride 71, 75, 79, 82, 84, Leguminosen 156 85,94,95,105,106,114,133,287,288,311, Lemna-Arten 186,190 331,332,333,337,338,339,340,366,367, Lemnaceae 186,190 410,433,436,453,473,475,485,492,494, Leonurus quinquelobatus 176 502,505,507,509,511,515,517 Lespecapitosid -+ Isoorientin 178 Lithium amide 230, 232 Lespedeza-Arten 188 Lithium diisopropyl amide 228, 230, 231, Leucanthosid 180 232,235,237,238,239,240,241,256,257, Leucodopachrome 525,526,557,560 271,340 Leucojum vernum 167 Lithium dimethylcopper 336, 338 Leucosid 167 Lithium hydride 256, 257, 258 Leucothoe keiskei 176 Lithium hydrido tri-t-butoxy-aluminate 99 Leucovernid 167 Lithium iodide 137,496 Leukämie-Mittel 502 Lithium-jodid s. Lithium iodide Leukopenia 113 Lithium-methoxid 204, 205 Levojunenol 348 Lithium thiophenolate 365 Lichens 221 Lithium tri-t-butoxyaluminohydride 288, Lichexanthone 224,271,272 337,338 Light petroleum 123 Loganin 469,470 Lignin 187, 537 Long, chain fattyacids 411 Liliaceae 186, 190 -, chlorides 423 Lilium auratum 162 Lonicerajaponica 160,162 Limonene 109,303,304 Lonicerin 160, 162, 195,200 Linaceae 186, 189 Lucenin 1 184, 185 Linaria-Arten 161 Lucenin 2 184 Linaria genistifolia 160 Lucenin 3 184, 185 Linaria vulgaris 160, 162 Lucenin 4 184 Linarin 160,162 Lucenin 5 184 -, -isovalerianat 176 Luffa echinata 169 Lincomycin 562 Luft-Oxydation 181, 198 Linoleic acid 427 Lumiphorbol-12,13,20-triacetate 449, 450 Linosid A -+ 4',7-Di-O-methyl-orientin-O• Lupinus-Arten 161, 188 rhamnosid 184,186 Luteolin 156, 157, 160, 168 Linosid B -+ 4',7-Di-O-methyl-orientin-(6- -, -7-apiosylg1ucosid 168 O-acetyl)-O-rhamnosid 184,186 -, 14C-Iabelled 186 Linum-Arten 189 -, -7-(p-cumaroyl)-O-ß-D-glucosid 175 672 Sachverzeichnis. Subject Index

Luteolin, Di-C-glycoside 184 Massenspektroskopie -, -6-C-ß-D-g1ucopyranosyl-derivat 179 Acorane derivatives 296f -, -g1ucoronid 173 Chamigrenes 296 -, -7-0-monoglucosid 194,195 Croton oil factors 394 f, 397, 40 1,402,403, -, C-Monoglykoside 178,179 425,426,427 -, -7-0-neohesperidosid 161 Di-C-glykoside 170 -, -7-0-rutinosid 160,162,200 Electron addition mass spectroscopy 394 -, -7-ß-rutinosid-4' -ß-D-g1ucopyranosid 171 Electron impact mass spectroscopy 394 -, -6-C-xylosid 184 12, 13-Epoxy-trichothecenes 83 -, -6-xylosid-8-g1ucosid 185 Glykoside, perdeuteromethylierte 170 -,7-0-xylosyl-g1ucosid 168 Myrochromanol 69 Lutexin ~ Orientin 178, 179, 180, 183 Myrochromanone 69 Lutonaretin ~ Isoorientin 178 Myrothecinic acid 98 Lutonarin ~ Isoorientin-7-0-glucosid 182 4a.-Phorbol 447 Lygos-Arten 188 Phorbol derivatives 395, 398,405,406,424 Lymphatic system 113 Roridin C 74, 83 Lysine 609,610 RoridinH 96 Lysine aminomutase 609 Spiro[4,51decane derivatives 296 D-a.-Lysine aminomutase 593 Verrucarin E 70 L-ß-Lysine aminomutase 593 Verrucarol 74,83 Violanthin 185 Mass spectroscopy s. Massenspektroskopie Macrolides 225 Mastocytom P-815 112 Magnesium 109 Matricaria-Arten 168 -, binding by eumelanins 554 McIlvain-Pufferlösung 196 Magnesium chelates 251, 253, 255, 261, 269 Melandrium suaveolens 188 Magnesium hydroxide 250 Melanic acid 546 Magnesium ion 255, 593, 609 Melanins 52lf Magnesium methoxide 251, 253, 254, 255, -, cation-exchange capacity 554 256,257,258,259,261,268,269 -, decarboxylated 546, 548, 549 Magnesium oxide 418 -, electron spin resonance 563, 564, 565 Magnetische Kernresonanz s. nuclear mag- -, from axolotl 562 netic resonance spectra -, from theeye 561 Madothecaplatyphylla 187 -, from the hair 561 Maleic anhydride 125 -, investigations by physical methods 562 Malefizöl 379 -, IR-spectra 562 Malonate 224, 228, 234 -, methylated 549, 568 -, a.-substituted 228 -, methylation 545, 556 Malonic acid 176 -, oxidation 546f -, dichlorophenyl ester 234, 240, 241 -, reduction 554 -, diethyl ester 244 -, synthetic 523 -, ester 236,481 -, UV-spectra 562 Malonsäure s. malonic acid -, X-ray diffraction 562, 563 Malonyl chloride 234 Melanochrome 525, 526 Malonyl coenzyme A 226 Melanocytes 529,530,531,570 Malvaceae 189 Melanogenesis 523, 524f, 540, 543f, 562, 563 Malus-Arten 157 Melanogenuria 529 Mammalian peroxidase 532 Melanoma 528,530,531,574 Mammalians 113 -, melanins 558f Mandelsäurenitrilglykosid 169 Melanoma tyrosinase 526 Manganese dioxide 393,416 Melanoproteins 537,560,561 Manganeseion 593,609 -, structure 553f Mannich-Kondensation 494,495 Melanosomes 529, 567 Sachverzeichnis. Subject Index 673

Melanuria 528, 529 8-Methoxy-5,7-3' ,4' -tetrahydroxyftavon 173 Mellitic acid 538, 539 Methoxytryptamin 488 Mentha-Arten 161 Methyl acetate 228, 231 Mentha crispa 160 Methyl acetoacetate 228, 236, 238, 244 M entha pulegium 160 -, enamine 4 Mercaptans 32, 33, 43 -, ketal 236 Mercaptoethanol 592, 604 Methyl adipic acid semialdehyde 98 Mercaptoethylamine 531 Methylalditolacetate 170 N-(2-Mercaptoethyl)dimethylamine hydro- Methyl 6Ot-allyl-6ß-dimethylamino-penicilla- chloride 531 nate 17 Mercuric acetate 45, 191, 192,503,513 Methylamine 102,620 Mercuric ion 618 Methylanthrone 274 Mercuric salts 617,618 4' -Methylapigenin 193 Mercury 36,617 -, -7-0-apiobiosid 193 -, pollution 618 -, 7-0-(3-0-benzyl-4,6-0-benzyliden)-ß-D- Mesaconate 605 glucopyranosid 168 Meso-cycloheylidenecyanoacetate isomer 312 -, -7-0-glucosid 193 Meso-dihydrovetivol 363 4'-0-Methylapiin 168 Meso-dihydro-ß-vetivone 362 Methylarsines 616,617 -, bis-benzylidene derivative 362 -, biosynthesis 616f -, 2,4-dinitrophenylhydrazone 362 Methylarsine synthetase 613 -, semicarbazone 362 Methylaspartate 604 Mesylchloride 80, 337, 338, 367,418, 436, 437 Methylate arsenate 616 4-0-Mesyl trichothecolone 79 Methylate arsenite 616 Metabolite CHT 387 66, 68 Methylation 154, lM, 167; 180,272,274,473, Metal porphyrins 588 545,561,568,617,619 M etarrhizium glutinosum 64 -, selective 133, 135 Methacillin 20 C-Methylation 204 Methane 617 N-Methylation 548 -, biosynthesis 602, 61Of, 617 Methyl benzylpenicillanate 41, 42 -, synthetase 613 Methylbenzoate 233, 234, 235 Methanobacterium M.O.H. 611,613,616, 4-0-Methylbisdehydrophorbol-12,20-di- 617 acetate 415 Methanogenic bacteria 615 -, -12,13-diacetate 415 Methanol 9, 15,36,46,51,65,66,69,89,98, Methyl-Ot-(I-bromomethyl) acrylate 307 101,123,135,156, 160, 161, 198,204,205, (+ )-S-2-Methylbutanamide 131 247,249,251,252,253,254,255,256,257, (+ )-S-2-Methylbutanoic acid 131 259,261,262,264,269,272,367,388,389, 2-Methylbutanolide 105 390,401,402,403,404,412,413,423,443, Methyl butyric acid 395 444,446,447,452,453,477,526,536,538, Methyl carbanion 611,615 549,556,588,610 ß-Methyl-y-carboxy-y-butyrolactone 85 Methanolyse 488 4-Methylcatechol 556 Methanolysis, photochemical 228 Methyl 6Ot-chloropenicillanate 15 Methanosarcina barkeri 610,613 Methylcobalamin 611, 614, 615, 617, 619 Methansulfosäurechlorid 509 Methylcobaloximes 602,611, 612, 615, 617, L-Methionine 102,144,618 618,619,620 Methionine biosynthesis 615, 618f Methylcobalt derivatives 614,618 Methionine synthetase 613,620 Methylcobinamide 618,620 Methoxymethyl esters 4 Methylcorrins 610f, 614f, 620 6Ot-Methoxypenicillin G 19 Methyl curvulinate 270, 271 4-Methoxy-2-pyrones 228 5-Methyl-cyclohexane-l ,3-dione 340 5-Methoxy-sterigmatocystin 122, 123, 127, 3-Methylcyclohexanone, hydroxymethylene 128 derivatives 306

Fortschritte d. ehern. org. Naturst. XXXI 43 674 Sachverzeichnis. Subject Index

1-Methyl-I ,2-cyclopropane-dicarboxylate Methylpenicillanate 15 605 3-Methyl-pentane-I ,2,5-triol 84 Methyl 6,6-dibromopenicillanate 15 [5,6-14C)-4-Methyl-pent-3-ene-magnesium Methyl-5,6-dihydroxyindoles 542 bromide 109 Methyl-2,5-dihydroxy-4-methylbenzoate 80 Methyl 6-phenylacetamidopenicillanate-l- MethyI6,7-dihydroxy-octanoate 98 (S)-oxide 28 Methylene chloride 10,65,101,126,135,139, 2-Methyl-6-phenyl-4-pyrone 247 387,393,395,403,424,425,426 4-0-Methylphorbol-12,13-diacetate 415 Methylenedioxy group 546, 548, 556 4-0-Methylphorbol-13,20-diacetate 415 ex-Methylene glutarate 593,605 4-0-Methylphorbol-12,13-20-triacetate 415 -, mutase 605 4-0-Methylphorbol-12,13,20-tridecanoate 5, 10-Methylenetetrahydrofolate 621 415 2-Methyl-4-ethylpyrrole 71 20-0-Methylphorbol-12,13-diacetate 415 ex-Methylglutaric acid 320, 324, 336 20-0-Methylphorbol-9, 12, 13-triacetate 415, ~-Methylglutaric acid 85 416 3-Methylglutaric acid semialdehyde 98 4-0-Methyl-4ex-phorbol-12,20-diacetate 448 -, -2,4-dinitrophenylhydrazone 98 4-0-Methyl-4ex-phorbol-12, 13,20-triacetate Methyl group rearrangements 110 448 Methyl group transfer reactions 619 Methyl6-phthalimidopenicillanate '10, 12,25 2-Methyl-4-hydroxybutanal 104 -, (R)-sulfoxide 32 Methylierung s. methylation 6-Methylpretetramid 273, 274 I-Methyl-indole-5,6-quinone 566,567 7-Methyl pyranopyrandione 253 Methyl iodide s. Methyljodid 5-Methylquercetin-3-galactosid 201 ~-Methylitaconate 605 5-Methyl-quercetin-3-glucuronid -+ Azalea- Methyljodid 205,230,369,414,415,417,418, tin 173 448,548,588,614 6-Methyl-quercetin-3-glucuronid -+ Patuletin 7-0-Methyl-kämpferol-6-C-~-D-glucosid -+ 173 Keyakinin 181 Methyl radicals 615,619 7-0-Methylkämpferol-3-0-trioside 170 Methyl-L-rhamnosid 164 Methyllithium 299, 329, 330, 334, 335, 337, N-Methyl-rynchophyllan 475 338,339,365,366,367,368,369 6-Methylsalicylic acid 225,226,241,266,267 3'-Methyl-Iutonarin -+ Iso-scoparin 178,180 O-Methylsterigmatocystin 122,123,125,127, Methylmagnesium-bromid 330, 331, 502 144 Methyl magnesium chloride 99, 300 -, synthesis 139,140 Methyl magnesium iodide 287, 332, 333, 340 Methylsuccinic acid 104, 105 [14C)-Methylmagnesium iodide 109 (R)-( + )-Methylsuccinic acid 85 Methylmalonate 607 Methylsulfonyl chloride 51 Methylmalonic acid 604· 5-Methyltetrahydrofolate 615,622 Methylmalonic aciduria 604 5-Methyltetrahydrofolic acid 610, 614, 618, Methylmalonyl-CoA 604, 608 619,620,621 -, -mutase 593, 604, 607, 608 Methylthioethers 620 Methylmercuric halides 618 6-Methyl-5, 7,4' -trihydroxyflavanon 117 Methylmercuric ion 617 Methyl-I,3,8-trimethoxyanthone-4-carboxy- Methylmercury 618 late 124, 125 -, derivatives 618 Methyltriphenoxyphosphonium iodide 366, -, formation 617 368 2-Methyl-2-(o-nitrophenoxy)-propionyl N-Methyl-tryptamin 510 group 4 N-Methyl-tryptophan 495 5-0-Methyl-orientin -+ Parkinsonin A 180 y-Methylvaleric acid 288 5-Methylorsellinate 244,245,252,253 Methylvinylketon 501,502,507 -, synthetase 226 Methylzucker 167 5-Methylorsellinic acid 226 Mevalölactone 85, 89 N-Methyl-oxytryptamin 475 Mevalonate s. mevalonic acid Sachverzeichnis. Subject Index 675

Mevalonic acid 99, 102, 103, 104, 105, 106, MyrochromanoI65,66,67,69f 107, 108, 109, 110,225 -, conformation 70 Mexican bean beetles 113 -, mono-acetyl derivative 69 Michael addition 299, 307, 312, 331, 481 Myrochromanone 65, 66, 69f Microspira tyrosinatica 523 Myrothecin 64 Milk toxin 131,132,137,138 Myrothecinic acid 73,96,97,98 Mineral salts 65 -, hydrogenation 98 Minovin 509 -, mass spectra 98 Mitosis 113 -, methyl ester 98 Mnium-Arten 187 -, structure 98 M onarda didyma 160 Myrothecium-Arten 64, 65, 66, 95, 103, 110, Moniliales 64 111 Monkeys 113 Myrotheciumroridum 64,65,66,67,89,94,109 Monoacetylzucker in Glykosiden 176 Myrothecium verrucaria 64, 66, 67, 84, 102 M onoclea Josteri 173 Myrtaceae 189 Monocotyledoneae 190 Monocyc\ofarnesol 109 Monodehydrororidin A 90 Naphthalene derivatives 263,265,271 Monoethyl malonate, magnesium salt 229, Naphthalenediols 221,244,269 232 Naphthalenes 287 Monohydroxyflavone 194 Naphthalenetriols 263 Monomethoxy-flavonole 156 Naphthol 269 Monomethyladipate semialdehyde 92 IX-Naphthol 244 Mono-O-methylphloroglucinol 125 Naphthol-gluco-furanosiduronsäure-3,6- I-Monopalmitine 389,400,401 lacon-diacetat 173 Monosaccharide 155 Naphthol-gluco-pyranosiduronsäure-3,6- O-Monoside 155 lacton-diacetat 173 Mono-tert. butyl-malonester 483 Naphthopyrone 271 Moos-Pflanzen 187 1,4-Naphthoquinone 566 Moraceae 189 Narcissin 162 Moulds 120,123, 147 Narcissus poeticus 176 Mouldy rice toxicosis 120 Narcissus tazetta 162 cis-trans-Muconic acid 73,84,86,88,89,103, Naringenin 157, 158, 160, 161, 165, 195,203 104 -, -4' -glucosid 204 -, esters, NMR-spectra 90 -, -5-0-glucosid 157,203 Muconomycin A 64 -, -4' -ß-D-glucosyl-7-ß-rutinosid 203 Muconomycin B 65 -, -5-glykoside 204 Murolene 348,349 -, -hexaacetat 203 Musci 187 -, -7-monoglucosid 196 Mushroom 524,526,530 -, -7-ß-neohesperidosyl-4' ß-D-glucopyra- -, polyphenol-oxidase 532, 542, 553, 574 nosid 171 Mutase action, mechanism 605f -, -7-0-neohesperidosid 161 Mycobacteria 112 -, -7-0-rutinosid 160 Mycotoxicosis 119, 120 -, -7-ß-rutinosyl-4' -ß-D-glucopyranosid 171 Mycotoxins 119,147 Naringin 161, 163, 164, 165, 194, 195, 196, -, biogenesis 140f 197, 199 -, characterization 123 -, -chalkon-neohesperidoside 164 -, chromatography 123 Narirutin 160, 165, 194 -, isolation 123 -, hexaacetat 203 -, structural elucidation 124 Natrium s. Sodium -, synthesis 132f Natrium-acetat s. Sodium acetate Myeloperoxidase 532 Natriumamid s. Sodium amide Myricetin-glykoside 156, 166 Natriumäthylat s. sodium ethoxide

43* 676 Sachverzeichnis. 'Subject Index

Natriumazid s. sodium azide 4-(-4-Nitrophenylazo-) benzoic acid (NP AB) Natriumbismutat s. sodium bismuthate 393,424 Natriumboranat s. sodium borohydride -, chloride 393 Natriumbromid s. sodium bromide -, mono esters 393 Natriumcarbonat s. sodium carbonate o-Nitrophenylsulfenyl group 4 Natriumchlorid s. sodium chloride Nitrous acid 13,14,15 Natriumhydrid s. sodium hydride NMR-spectra s. nucIear magnetic resonance Natriumhydrogencarbonat s. sodium hydro- spectra gen carbonate ß-Nonacarbonyl compounds 241,265 Natriumhydrogensulfid s. sodium hydrogen Nootkatane -+ Valencane 328, 345, 352 sulfide Nootkatene 343 Natriumhydrogensulfit s. sodium hydrogen Nootkatone 327,343 sulfite Norepinephrine 560,567 Natriumhydroxid s. sodium hydroxide Norroridinic acid 105 Natriumjodid s. sodium iodide 1'-N or-tetrahydro-13' -dehydrororidinic Natriummethylat s. sodium methoxide acid 104,105 Natriumnitrit s. sodium nitrite Nothofagusfusca 189 Natriumperiodate s. sodium periodate NPAB s. 4-(4-Nitrophenylazo-)benzoic acid Neoacorone 360 NucIear magnetic resonance spectra Neohesperidin 161,163,165,196,197 Acetobromzucker 193 -, -dihydrochalkon 164 3-Acetyl-5-formylpyrrole 71 -, -disaccharid 164 3-Acetylpyrrole 71 Neohesperidose -+ Sophorabiose 159, 163, Aflatoxin-B I 130 164, 165, 192 Aflatoxin-G 1 131 -, -acetat 192 Aflatoxin-M I 132 -, -heptaacetat 192 Agarospirol derivatives 309, 311, 312, 313, Neophorbol 416,428,436 333 -, -20-acetate 443 Aspalathin 182 -, -13,20-diacetate 408,416,442,443 Aspertoxin 128, 132 -, -13,20-diacetate-3-benzoate 418 Apigenin-glucuronide 173 -, 12, 13-ketol rearrangement 443 Bayin 180 Neoponcirin 161 13C-labelled compounds 103, 140 Nerolidol 301,304,305 Croton oil factors 396f, 422 (- )-trans-Nerolidol 348,349,351 CycIization products of phenyltrioxo- Neuromelanin 567 heptanoic acid 247,250 Neurospora crassa 531 2,3-Dihydrofuran 126 Neviusia alabamensis 160 3,4-Disubstituted pyrroles 71 Nicotiflorin 162 Dopamine-melanin 568 Nicotinamide-adenine dinucIeotide 565 Flavonoid-C-glucoside 179 Nicotinic acid 405 Glucosidacetate 179 Niederenergie-Phytochrom-System 186 6-Halopenicillanic acids 13 Nitella Hookeri 187 ß-Hydroxybenzoylvitexin-derivate 184 Nitric acid 324 Isohemiphloin 181 p-Nitrobenzene sulfonyl chloride 51 Isoorientin 179 p-Nitrobenzoyl chloride 423 Lumiphorboltriacetate 450 p-Nitrobenzyl esters 4 O-Methyl-sterigmatocystin 128 p-Nitrobenzylidene group 4 Monodehydrororidin A 90 p-Nitrocarbobenzyloxy group 4 Muconic acid esters 90 Nitrogen s. Stickstoff Myrochromanol 69 Nitrogen dioxide 16 Myrochromanone 69 Nitrogen ylide 17 Myrothecinic acid methyl ester 98 Nitromethane 192,391,392 Naphthol-glucuronide 173 p-Nitrophenol, esters 3 Orientin 179 Sachverzeichnis. Subject Index 677

Peltatosid 169 Propanediol 596 Penicillin sulfoxides 24 Water 107 Phenylcylohexylcarbinole 179 Olefin oxides 594 Phorbobutanone 439,443 Olefins 32, 33 PhorboI405,406,409 Oleic acid 380, 427 4ex-Phorbol 447,449,450 Ombuosid -+ 7,4' -Dimethyl-quercetin-3- Phorbol-derivatives 405, 408, 431, 435, rutinosid 162 443, 449 Oncogenic actitivity 379 Roridin A 90 Opopanax chironium 187 Roridin C 74 Optical rotation Roridin E 95 Acoradienes 354, 355, 356, 357 Roridin H 96, 98 Acoradione 359,360 Roridins 76, 77, 90 Acorane 357 Roridinic acid esters 90 Acoratriene 354 Saponaretin 179 Acorene 355 Spin-spin decoupling experiments 98 Acorenol 359 Sterigmatocystin 126, 130 Acorenone 358 Trichodermin 79 Acorone 359 Trichothecan derivatives 85 Aflatoxin-B I 128 Trichothecolone 79 Agarospirol 363 Verrucarin A 86 Alaskane 358 Verrucarin B 88 Alaskene 355 Verrucarin E 71 Avicularin 155 Verrucarin J 89 Croton oil fractions 312, 383, 385, 387, Verrucarinolactone 85 389 Verrucarins 76,77,90 Cryptoacorone 360 -, derivatives 87 Dihydro-ex-alaskene 357 Verrucarol 74,75,79 Dihydrohinesol 318,363 Vetivane derivatives 318 Epiorientin 180 Violanthin 185 Flavanone 165 Vitexin 179 Flavanon-7-0-glykoside 197 Vitexinderivate 183 Flavanon-neohesperidoside 161 Nucleophilicity 586, 587 Flavanon-rutinoside 160 Nucleophilic reactivity constants 588 Flavon-neohesperidoside 161 Nucleosides 597 Flavon-rutinoside 160 Nucleotides 600 Guajaverin 155 Nucleotide triphosphate 601,602 Hinesol 363 Nymphaea alba 189 -, degradation products 322 Nymphaeaceae 189 Isoacorone 359 Nymphoides peltata 169 Isovetivane 362 Isovetivene 361 Isovetivenene 361 ß-Octacarbonyl compounds 240, 265 Neoacorone 360 Octahydrororidin D 96 Orientin 180 Octahydrororidin E 95 Peltatosid 169 Octahydrororidin H 96, 98 Polystachosid 155 Octaketone 240,241,265 Quercetin-3-0-diglucosid 167 Octanoic acid 395 Reynoutin 157 Oedema formation 379 Roridins 66, 67 0' Keeffe distribution 38Jf, 385, 388, 399,444, Verrucarins 66,67 445,453 Vetispirene 361 180-labelled compounds Vetivane-derivatives 318 Molekular oxygen 531 ß-Vetivone 316, 362 678 Sachverzeichnis. Subject Index

OpticaI rotatory dispersion 8-0xo-5-thia-l-aza-bicyclo[4.2.0]oct-2-ene Acoradien derivatives 294, 295 ring system -+ Cephem 28 Acorone 289 Oxygen 17,393,404,510,524,525,526,529, ß-Alaskene derivatives 294, 295 597,602 Apiin 168 Oxymercurierung 478,481 Cryptoacorene 360 Ozon 24,36,86,87,90,94, 109, 125, 165, 179, Cryptoacorone 289 238,287,291,311,312,316,318,322,323, Isoacorone 289 324,498 Isocalamenene 294 Naringenin 165 Paeonia arabica 160 Zizanoic acid, degradation product 346 Paeonia-Arten 161 Optische Drehung s. optical rotation Palasitrin 198 OrangenschaIen 183 Palladium 7,8,13,14,16,18,51,97,128,136, Oricinol 220, 221, 226, 246, 253, 255, 258 164,203,292,300,316,324,329,337,338, Orcinyl triketo esters 271, 272 342,408,419,420,428,439,473,563,556 ORD-spectra s. opticaI rotatory dispersion Pancreatic digestion 561 Organocobalamin intermediates 598 Papaver somniferum 167 Organocobaloximes 602 Paper chromatography -, intermediates 620 Croton oil 380 Organocorrins 602 Indole derivatives 556 -, intermediates 606,607, 609 Melanins 574 Organomagnesium halides 585 Mycotoxins 123 Orientin 178, 179, 180, 183 Oxidationsprodukte von Catechol 533 -, -O-arabinosid 186 Pyrrole carboxylic acids 546,547 -, 14C_Iabelled 186 Papierchromatographie s. paper chromato- -, -3'-methyläther 180 graphy -, -5-methyläther 180 Paradisiol 352 -, Xylosylderivat 184, 186 Paramagnetism 60 I Omithine 609 -, in melanins 563, 564 Omithine aminomutase 593, 609 Parkinsonia aculeata 179, 180 Ornithogalum-Arten 190 Parkinsonia-Arten 188 Orsellinic acid 221, 222, 223, 226, 251, 252, Parkinsonin A -+ 5-0- Methyl-orientin 178, 253,255,258 180 Oryza sativa 191 Parkinsonin B -+ 5,7-Di-0-methyl-Iuteolin- Osmi um tetroxide 36,69, 106, 138,420,422,429 8-C-g1ucosid 178, 180 Oxalic acid 90, 91, 368 Partridge 120 Oxalidaceae 189 Passiflora-Arten 189 Oxalis cernua 189 Passifloraceae 189 Oxazillin 8, 9 Patuletin -+ 6-Methyl-quercetin-3-glucuronid Oxazolone 21 173 Oxazolines 41,45 -, -3-rutinosid 162 Ox-choroid melanin 561 Patulin 225 Oxetane ring 75, 83 Peanut 120 2 ß-13-0xidoapotrichothecanes 83 Pechmann condensation 133, 134, 135, 136, Oxidation, spontane 163 '.137 Oxidative ring cleavage 145 Pectolinarigenin 161 Oxindol-Alkaloide 469 -, -7-0-rutinosid 162 Oxiranes 410 Pectolinarin 161 Oxiran ring 75, 83 Peltatosid 169 -, c1eavage 81,107 Penam 28, 34, 35 5-0xohexenoic acid 242 Penama1dic acid 21 8-0xo-5-thia-I-aza-bicyc1o[4.2.0Joctane ring Penicillanic acid 2, 3, 14, 23 system -+ Cepham 28 -, chlorination 42, 43 Sachverzeichnis. Subject Index 679

Penicillanic acid, Curtius reaction 38 Penicilloic acids, oxidation 47 -, derivatives, base-catalyzed rearrangement Penicilloylating agents 20 12 Penicilloyl-specific antigens 21 -, Raney nickel desulfurization 47 Penillic acid 21 Penicillanyl alcohols 50 Penilloic acid 21 -, transformations 51 Pentaacetic acid 222, 236, 237 Penicillenic acids 20, 21 -, ester 236 Penicillin -, masked 261 -, acylation ofthe 6-amino group 3 4,7 a, 12ß, 13,20-Pentaacetoxy-1 O-bromo- -, aldehydes 50 6aH-1-tiglien-3-one 420 -, alkylation ofthe 6-amino group 5f 4,9, 12ß, 13,20-Pentaacetoxy-7ß, 10-dibromo- -, allergenicity 20, 22 6aH-I-tiglien-3-one 420 -, antimicrobial activity 4,6,13,16,17,19, 4,7a, I 2ß, I 3,20-Pentaacetoxy-l a,2,6-tri• 21,28,38,39 bromo-9-hydroxy-2ßH, 6aH-tiglian-3- -, base treatment 9 one 420 -, chemical c1eavage of side chains 4 Penta benzoyl-quercetin 200 -, cleavage ofthe C7-N4-bond 20f 1,4-Pentadiene 236 -, conversion to diazoketones 50 4,9, 12ß, 13,20-Pentahydroxy-I ,6-tigliadien-3- -, diazotation ofthe 6-amino group 13 one -+ Phorbol 409 -, epimerization ofthe 6-position 9f Pentaketide natural products 261 -, hydrolysis of the 6-amido group 6f 3,5,7,9,1 I-Pentaketo acids, synthesis 238f ~, iodometric determination 47,48 Pentaketo diacid 240, 264 -, ß-Iactam ring, opening 20f 3,5,7,9,1l-Pentaketo esters, synthesis 238f -, ß-Iactam ring, reactions 3f 1,3,5,7,9-Pentaketones 237f, 240 -, nomenclature 2f -, acetyl-terminated 263 -, nuclear transformations 47 -, cyclization 263 -, pharmacological properties 6 Pentane 304 -, polymerization 22 2-Pentene-l,5-dione 241 -, Raney nickel desulfurization 47 Peptides, N-penicilloyl derivatives 21 -, rearrangement via diazo and azide com- Peptidoglycan synthesis 17 pounds 35 Peptone 65 -, substitution at the 6-position 17 Peracids 24,421,422 -, thiazolidine ring, cleavages 35 Perbenzoic acid 421 -, thiazolidine ring, reactions 23f Perchloric acid 423 -, thioacids 50 Perhydroazulene-system 435,444 -, transpeptidase inhibition 18,20 Perhydro-benzazulene structure 410 Penicillin G 2, 6, 16, 19 Perhydrocyc1opropabenzazulene 409 -, benzyl ester 7 -, structure 457 Penicillin V 11 Perhydroperylene 538, 539 Penicillin-3-carboxylic acid 48 Periodic acid 84,85,97,98, 105, 106, 162, 168, -, acylmethyl esters 48 179,185,412,483,488,495,502,505,512 -, amides 48 Perjodsäure s. periodic acid -, hydroxamic acids 48 Permethylierung von Glykosiden 155, 164, -, modification 48f 167,170 Penicillin sulfones 24 -, nach Hakamori 174 Penicillin sulfoxides 24f Pemicious anemia 604 -, hydrazides 45 Peroxidase 532 -, rearrangements 24,28,29,31,33 Peroxyphthalic acid 288 -, transformations 27 Perylene 539 Penicillin-thiocarboxylic acid 49 Perylenequinone 539 Penicillium griseofulvum 226 Petroleum ether 65, 403, 453 Penicillium Wortmannii 65 Petroselinum-Arten 168 Penicilloic acids 20, 21 Petunia hybrida 175 680 Sachverzeichnis. Subject Index

Petunosid 175, 176 Phloracetophenonglykoside 164, 195, 197 Peucedanum graveolens 187 -,4-0-glykosid 196 Peucedanum ostruthium 160, 162 -,4-neohesperidosid 196,197,204 Phaeomelanins 522, 523, 524, 561, 570f, 575 Phloroglucinol derivatives, synthesis 244,246, -, biogenesis 573 247 Phaseolus-Arten 166 Phloroglucino1s 253,255,257,259,261 Pheasant 120 -, methylated 258 Phegopolin 201 -, methyl ether ...... Cotoin 252, 253, 258 Phenacyl esters 4 Phlorrhizin ...... Dihydroxychalkon-2' -mono- Phenacyl pyrones 255 D-glucosid 157,158,202,203 -, cJeavage and recyclization 256 Phlox drummondii 184, 189 Phenethylamine 568, 570 Phoenix dactyliJera 190 7-Phenetyl-pyranopyrandiones 255 Phorbobutanone 428,438,439,440,441 Phenol 530,561 -, -20-acetate 438 Phenolase 530 -, -20-benzoate 438, 443 Phenole s. phenols -, -20-tritylether 438 Phenolic bromo esters 299 Phorboisobutanone 438, 439 Phenolic compounds, biogenetic type syn- -, -semiketal 440,441 theses 265 PhorboI380,398,404,446,447,452,454,455, -, biosynthesis 222 456 Phenol-Kohlenhydrat-Verbindungen 155 -, -12,13-acetate-acylates 423f -, Glykoside 177 -, acetates 412,413,414,438 Phenol melanogens 529 -, acetylation 380,398,413,423 Phenol-polysaccharid 173 -, alkylation 414 Phenols 193,200,202,219 -,-20-benzoate 438 -, annelation with ß-keto esters 244 -, bromination 420,421 -, enzymic oxidation 522, 539 -, -20-(5-bromofuroate) 409 -, monohydric 531 -, catalytic hydrogenation 419 -, synthesis from two ketide fragments 245 -, circular dichroism 405,406,407,408 Phenoxid-Anion 199 -, dehydration 408 Phenoxykoh1ensäurech1orid 496 -, dehydrogenation 408,428 6-Phenylacetamidopenicillanic acid 2 -, 20-deoxy-tetrahydro-derivatives 420 6-Phenylacety1hydrazinopenicillanic acid 16 -, derivatives, UV-spectra 408 6-Phenylacetylhydrazonopenicillanic acid 16 -, epoxidation 421 Phenylalanine 186,555,559,560,561 -, -6,7-epoxides 410 -, metabolism 560 -, esters 411,413,416,423,452 Phenylcyclohexylcarbinole 179 -, ethers 414f p-Phenylendiamine 565 -, ethyl derivatives 414 Phenyl-C-glykosid 206 -, -12-ethyl-20-trity1ether 415 I-Phenyl-1,3,5-hexanetrione 235,238 -, -13-ethyl-20-tritylether 415 -, trilithium salt 232 -, Flaschenträger reaction 440 Phenylhydrazin 507 -, functional derivatives involving the Phenylketonuria 561 C=C-bonds 419 Phenyl-magnesium iodide 105 -, functional derivatives of the carbonyl Phenyl methyl tetraketone 235, 259, 260 group 410f 7-Phenyl-pyranopyrandiones 255 -, functional derivatives of the hydroxyl 7-Phenyl-3,5,7-trioxoheptanoic acid 247,231, groups 411 248 -, higher esters 398f -, methyl ester 249 -, hydrobromination 420 9-Phenyl-3,5,7-trioxo-8-nonenoic acid 226 -, infrared-spectra 405, 424, 425 Ph1egmonous inflammation 379 -, mass-spectrometry 395,398,405,406,424 Ph1oracetophenon 195 -, monoacetates 413,423 -,2,4-diglykosidacetate 195 -, NMR-spectra 405,406,408, 409 Sachverzeichnis. Subject Index 681

Phorbol, oxidation 420f 6-Phthalimidopenicillanoyl-diazomethane 52 -, oxidation of single hydroxyl groups 416 Phytochrom-System 186 -, oxidative ring opening 428f Phytolacca dioica 162 -, pentaacetate 405,411,412,413,416,420, Phytotoxin 379 421,422,427,437 Pig 113 -, preparation 445 Pimelic acid derivative 316, 322 -, reactions alteringthe tigliane skeleton 428f Pinaceae 187 -, rearrangements 436 Pinacol rearrangement 438,441 -, stereochemistry 405f Pineneedle blight 147 -, structure 405f Pine trees 252 -, substitution and elimination of hydroxy Pinocembrin 161, 162, 165, 251, 252, 255 groups 418 -, -2,3-dihydroverbindungen 162 -, -4,12,13,20-tetraacetate 412,413 -, -7-rhamnogiucoside 165 -, -9,12,13,20-tetraacetate 411,412,413 -,7-0-rutinosid 161 -, tetraacetates 445, 448 Pinosylvin 246,251,252,255 -, triacetate 398,408,410,411,412,413,414, Piperidine 37 415,417,418,419,420,421,422,423,428, Piperidonring 491 429,436,438,445,448,449,450,451,452, Pisum-Arten 167 455,456 Pisum sativum 170 -, triacy1ates 423, 427 Pivalic acid, mixed anhydrides 3 -, -12,13,20-tribenzoate 410,413,427 Plagiochila asplenoides 187 -, -tridecanoate 415,418,419 Plantaginin 200 -, triesters 427,428,455 Plantago asiatica 200 -, -20-tritylether 414,415,417,438 Platanus acerifolia 175 -, ultraviolet-spectra 405, 407, 409, 447 Platinum 291,367,419 -, X-ray diffraction analysis 408,409 Platinum dioxide 5 4~-Phorbol 444,446,447f Plummera ambigens 162 -, mass-spectroscopy 447 Pluricarcinogenesis 457 -, NMR-spectra 447,449, 450 Poaceae 190 -, pentaacetate 448,450 Poa compressa 191 -, stereochemistry 449 Polemoniaceae 189 -, tetraacetate 445, 448, 450 Polyacetylenic compounds 539 -, tetrabenzoate 450 ß-Polycarbony1 compounds 227, 243f -, triacetate 445,448,449,450,451 -, biological cyclization reactions 255 -, -20-trityl ether 448 -,reduced 241,265 -, ultraviolet-spectra 447,449 -, partially cyclized 269 10ß-Phorbol 451,452,454 -, syntheses 227f, 270 Phorbo1actone-semiacetal 433, 434, 435 ß-Polycarbonyl intermediates in biosynthesis -, -12,20-diacetate 442 ofpolyketides 218,219,220,226 Phorbol-C2HsOH s. alcohol phorbol Polycarpon tetraphyllum 188 Phorbo1ester 377f Po1ycyclic compounds, biogenetic type syn- Phorbol reaction 404 theses 271 Phosphate buffer 542 Polyethylene glykol 383 Phosphoric acid 303 Polygonaceae 189 Phosphor pentachloride 6,8,9,43 Polygonum aviculare 155 Phosphor tribromide 27 Polygonum orientale 179, 189 Phosphorus oxychloride 337, 339, 344, 367, Polygonum polystachum 156 368,438 Polygonum reynoutria 157 Phosphorus pentoxide 542 Polyhydroxyanthraquinones 141, 142, 147 Photosynthetic bacteria 587 Polyhydroxy-fiavone 154 Photochemische Umwandlung 182 Polyhydroxy-fiavonoide 153 6-Phthalimido-penicillanate 25 Polyhydroxy-flavonole 154, 199, 200, 201 6-Phthalimido-penicillanic acid 38 -, C3-OH-Glykosidierung 100 682 Sachverzeichnis. Subject Index

Polyhydroxy-flavonole peracetate 200 Primverose -+ 6-0-(ß-D-Xylopyranosyl)-ß- Polyhydroxynaphthacene 144 D-glucopyranose 159, 167, 168 Polyketide 111 Primveroside 168 Polyketide metabolites, biogenetic-type syn- DL-Proline 102 theses 217f DL-Propanediol 592, 596 Polyketides 141,142,143,145 DL-Propanediol hydrolase 592f -, reduced 243 1,3-Propanedithiol ditosylate 368,369 Polyketide xanthones 265 n-Propanol 600 ß-Polyketo acids 219,223,224,227 2-( 1-Propenyl)-4-hydroxy-6-methyl-chro• Polyketo carbinols 265 mone -+ Myrochromanol 69 ß-Polyketo esters 257 2-(I-Propenyl)-4-oxo-6-methyl-chromone -+ Polyketone intermediates 225 Myrochromanone 69 ß-Polyketones 219,221,227 Propionaldehyde 592, 596 -, carboxylation 228 Propionibacteria 604 Polyketo olefins 265 Propionibacterium shermanii 593 Polymerization reactions 6 Propionic acid 90, 91 Polymethacrylate 563 Propionyl carbonium ion 607 Polyphenol oxidases 530, 531, 532 Propyl chloride 588 Polysaccharid vom Hemicellulose-Typ 173 1,2-Propylenglykol 185 Polystachosid 155 Propylhygric acid 562 Poncirin 161, 162, 165, 194, 197 Propyl-proline 562 Poncirus trifoliata 160, 162 Proteins 523, 529 Populnin -+ Kämpferol-7-glucosid 199 -, corrin binding 609 Populus yunnanensis 170 -, hydrolysis 555 Porella platyphylla 187 -, of croton seeds 379 Poriolid 176, 177 Protetrone 273, 274 Porphyrins 587, 588 Proteus mirabilis 112 Potamogetonaceae 191 Protocatechua1dehyd-3-glucosid 198 Potamogeton natans 191 Protocatechuic acid 536, 537 Potassium acetate 195,369 Prunin -+ 5,7,4'-Trihydroxy-flavanon-7-0- Potassium amide 230, 231, 232 glucosid 158, 196,.199 Potassium borohydride 16 Prunus -Arten 157 Potassium bromide 396, 424 Pseudoguaianolide type compounds 447 Potassium t-butoxide 10, 12, 37,46, 83, 299, Pseudomonas aeruginosa 112 300,337,339,478,510 Pseudomonas denitrificans 587 Potassium ferricyanide 554 Pseudovincadifformin 505 Potassium hydrogen carbonate 72, 388 Psidium guaijava 155 Potassium hydrogen sulfate 89 Psoralea-Arten 188 Potassium hydroxide 89, 91, 92, 94, 96, 97, Pteridaceae 187 108,125,164,194,195,196,197,202,203, Pteridophyta 187 204,249,250,252,253,254,255,256,257, Pueraria hirsuta 166 258,259,260,261,262,263,264,266,267, Pueraria Thunbergiana 180, 188 269,272,300 Puerarin 180,181 Potassium ion 592, 593 -, -4',6"-diacetat 181,184 Potassium permanganate 36,37,85,104,125, Pustules formation 379 546,556 Pyranoide Form 155 Potato 524, 530 Pyranopyrandiones 234, 236, 237, 240, 241, Poultry 120 252,253,258,259,263,265,268 Pretetramid 225,241,273,274 -, cIeavage-recyclization 254 Prezizaene 347,348,349 Pyridine 8, 28, 37, 51, 66, 69, 72, 80, 92, 95, Primula-Arten 167 138, 139, 140, 160, 161,180, 193, 197, 199, Primula sinensis 169 200,201,203,324,333,335,341,344,364, Primulaceen-Familie 171 367,368,398,405,406,411,412,413,414, Sachverzeichnis. Subject Index 683

415,416,418,423,431,432,433,434,435, Quercetin-4' -glucosid 202 436,437,438,439,441,442,443,448,453, -, -5-0-glucosid 202 500,542,565,688 -, -7-glucosid 200 Pyridiniumsalze 473 -, -glucuronid 173,201 y-Pyridone structure 71 -, -glykoside 166 Pyridoxal 610 -, Kaliumsalz 200 -, phosphate 593, 609 -, -O-monoside 156 Pyrone acids 234, 237, 239, 240, 241, 258 -, -3-mono-xylosid 157,201 -, methyl ether 259 -, -3-0-neohesperidosid 165 -, ring-cleavage-recycJization 265 -, -3-cx-L-rhamnopyranosyl-7-ß-D-gluco- Pyrone derivatives 219,222,223,232,234,236 pyranosid 203 Pyrones 230,231,237,246,247,257,259 -, -3-rhamnosid 200,201 -, ester 252 -, -3-0-rutinosid 162, 191,201 -, methyl ethers 257 -, -3-ß-rutinosid-7-ß-D-glucosid 171 -, monocycJic 255 -, -3-ß-rutinosyl-7-ß-D-glucosid 203 Pyrrol black 557 -, -3-0-sophorosid 167,201 Pyrrol derivatives 66, 68, 70f -, -3,7,4' -tribenzyläther 202 -, biosynthesis 102 -, -3-ß-D-xylopyranosyl-7-ß-D-gluco- -, detection 101 pyranosid 203 Pyrrole-2-carboxylic acid 546 Quercimeritrin 156, 199,200 Pyrrole-3-carboxylic acid 546 Quercitrin 156 Pyrrole-2,3-dicarboxylic acid 546, 552, 557, Quinhydrone 565 558,561 o-Quinoid structures 525 Pyrrole-2,4-dicarboxylic acid 546, 556, 558 Quinol 560 Pyrrole-2,5-dicarboxylic acid 546, 556, 558 Quinoline 72,194,195,196,198,199,200 Pyrrole, oxidation 557 Quinone 274 Pyrroles, 3,4-disubstituted 71 o-Quinones 530,531,537 Pyrrole-2,3,4,5-tetracarboxylic acid 546, 548, p-Quinones 525 557,558,561 Pyrrole-2,3,4-tricarboxylic acid 557 Racemization 70 Pyrrole-2,3,5-tricarboxylic acid 546, 547,548, Rainbow trout 120 552,556,557,561 Rana esculenta 383 Pyrrolidine derivatives 334 Raney nickel 50, 287, 291, 321, 323, 324, Pyruvate 593,609,610 368,418,500,539 Raney nickel desulfurization 47,131 Quebrachamin 501,504,507 Ranunculaceen-Familie 171,189 Quecksilberacetat s. mercuric acetate Ranunculus-Arten 189 Quecksilberbromid 191 Rats 113, 120 Quecksilbercyanid 191 Reformatskyaddition 334 Quecksilbersalze 193 Reserpin 487 Quercetagetin-glykosid 156 Resorcinols 252,255,259,260,261,263,265, Quercetin 154,156, 158 269 -, -3-0-arabinoglucosid 169 -, by cycJization of triketones 246 -, -3-arabinosid 156,201 y- Resorcylic acid 125 -, -cx-L-arabofuranosid 155 Resorcylic acids 247,252,255 -, -cx-L-arabopyranosid 155 Resorcylic ester 250,255,257 -, -3-0-(cafTeoylsophorosid)-7-glucosid 176 -, methylated 252,257,259 -, -4,7'-dibenzyläther 202 Retroaldol-Spaltung 502 -, -3,7-diglucosid 203 Retro-Mannich-Kondensation 507 -, -3-0-galactosid 201 Retro-Michael cJeavage of a diketone 79 -, -gentiobiosid 167,201 Reynoutrin 157 -, -3-0-glucosid 201 Rhamnazin 170 -, -3'-O-glucosid 202 Rhamnetin 170 684 Sachverzeichnis. Subject Index

Rhamninose 170, 172 Roridin A, hexahydroderivative 90 Rhamnodiastase 162, 165, 191 -, hydrolysis 73, 90 6-0-(0(-L-Rhamnopyranosyl)-ß-D-galacto• -, insecticidal activity 113 pyranose -+ Robinobiose 159, 165, 170, -, LDso 113 l7l,192 -, NMR-spectrum 76,77 2-0-(0(-L-Rhamnopyranosyl)-ß-D-giuco• -, oxidation product 94 pyranose -+ Sophorabiose 159, 163, 164, -, production 65 165,192 -, spectral data 89 3-0-(0(-L-Rhamnopyranosyl)-ß-D-giuco• -, structure 89f pyranose 159 -, tetrahydroderivative 90 6-0-(0(-L-Rhamnopyranosyl)-ß-D-gluco• -, thin layer chromatography 101 pyranose -+ Rutinose 159, 162, 163, 165, -, UV -spectrum 90 191 Roridin B -+ Ergosterol 66, 68 L-Rhamnose-+6-Deoxyhexose 155, 166, 170, -, thin layer chromatography 101 180,184,185 Roridin C 67,74, 75f, 78, 83, 109, 111 Rhamnosyl-arabinose 159 -, -p-bromobenzoate 75 -arabinosid 159 -, cytostatic activity 112 -galactopyranosyluronsäure 159 -, gas-liquid chromatography 102 -galactose 159, 172 -, mass spectrum 83 -galactosyl-galactose 172 -, mesylation 79 -glucose 159,162 -, NMR-spectrum 76,77 -glucosid 159 -, structure 78 Rhamnosyl-glucosyl-galaktose 172 -, thin layer chromatography 101 Rhamnosyl-glucosyl-glucose 172 -, total synthesis 99f Rhamnosyl-Iaminaribiose -+ O-ß-D-Gluco- Roridin D 66, 74, 94f, 96, 111 pyranosyl-( 1-+3)-0-0(-L-rhamnopyrano• -, hydrolysis 73, 94 syl-( 1-+2)-0(-L-rhamnopyranose 172 -, mono-O-acetyl derivative 94 Rhamnosyl-rhamnose 159 -, NMR-spectrum 76, 77 Rhamnosyl-xylose 159 -, production 65 Rhamnus alaternus 170 -, structure 94 Rhamnus catharticus 170 -, thin layer chromatography 101 Rhamnus infectorius 170 Roridin E 66, 74, 95f, 111 Rhamnus tinctoria 170 -, hydrogenation 95 Rhizobium meliloti 600 -, hydrolysis 73, 95 Rhodium 295 -, IR-spectrum 95 -, nuc1eophilicity 587 -, mono-O-acetyl derivative 95 Rhoifolin 161, 164, 195 -, NMR-spectrum 76,77,95 Rhus succedania 161 -, production 65,95 Ribonucleotide reductase 583, 598, 600f. -, thin layer chromatography 101 Ribonuc1eotide reduction 598 Roridin H 67,73,74, 96f, 111 Ribonuc1eotides 600,601,602 -, diastereoisomers 98 Ring cleavage 225, 228 -, hydrogenation 96 Ringisomerisierung 204 -, hydrolysis 96 -, nach Wessely-Moser 179 -, mass spectrum 96 Robinill pseudacacia 160, 162, 166 -, NMR-spectrum 76,77,96,98 Robinin 165, 166 -, structure 96 Robinobiose 159,165,170, l7l, 192 -, thin layerchromatography 101 Röntgenstrukturanalyse s. X-ray analysis Roridinicacid 73,90,91,92,94,103,104,105 Roridin A 64,66,74,91,95,96,105,111,112 -, di-O-acetyl dimethyl ester 90 -, biosynthesis 103 -, dimethyl ester 90 -, cytostatic activity 112, 113 -, NMR-spectrum 90 -, di-O-acetyl derivative -, tetrahydrodimethyl derivative 90 -,9,IO-epoxide 94 -, UV-spectrum 90 Sachverzeichnis. Subject Index 685

Roridins 63f Salicylic acid 536, 537 -. antihilltic actil it) 112 Salipurposid -+ Helichrysin B 158, 165,202, -. antifungal properties 112 203 --'--, biological activity 112, 114 Salivary flush 379 -, biosynthesis 102f Salix bakko 169 -, chemical transformations 68 Salix caesia 168 -, chromatography 65 Salix purpurea 202 -, circular dichroism 87 Salix repens 168 -, hydro lysis, base catalyzed 73 Salmonella abortus equi 112 -, liquid-liquid partition 65 Salzsäure s. hydrogen chloride -, mass spectra 83 Sambubiose -+ 2-0-(ß-D-Xylopyranosyl)-ß• -, methods of assay 100f D-glucopyranose 159,167,168,171,183, -, NMR-spectra 76, 77 193 -, optical rotation 66 Sambucus nigra 167 -, production and isolation 65 Sanguineous diarrhoea 379 -, structure 68f Saponaretin -+ Isovitexin 178,179,181,186 -, thin layer chromatography 101 -, -4'-0-glucosid -+ Isosaponarin 182 -, total synthesis 99f Saponaretin-Typ 205' -, toxicity 112,113 Saponaria-Arten 188 -, UV-spectra 100,101 Saponaria officinalis 179, 182 Rosa-Arten 167 Saponarin 179,180, 182, 183, 186 Rosaceae 189 Sarcoma 37 113 Roßkastanie 202 Sarothamnus s. Cytisus Rotationsdispersion s. optical rotation dis- Sarothamnus scoparius 180,189,539 persion Sarothanosid 161,165, 194 Rotenone 380 Sarpagin-Typvon Indolalkaloiden 469 ß-Rotunol 344, 345, 352, 362 Sauerstoff s. oxygen Roxburghin D 482 Schaftosid 185 Rubidium ion 593 Schichtchromatographie, präparative 495 Rubrofusarin 224 Schiff bases 4, 5, 6, 17 Rungia repens 165 Schmidt degradation 105 Rungiose 159, 165 Schwefelsäure s. sulfuric acid Russula nigricans 524 Schwefel-Ylid-Kondensation 494 Rutaceae 162, 189 Scintillation counting 558 Ruta graveolens 162 Scirpus-Arten 190 Rutin -+Quercetin-3-0-ß-rutinosid 162,191, Scolymosid -+ Lonicerin 160, 162, 195 200 Scoparin 178, 180 Rutinose -+ 6-0-«(1.-L-rhamnopyranosyl)-ß• Scoparosid s. Scoparin D-glucopyranose 159, 162, 163, 165, 191, Scrophulariaceae 174,190 192 Scrophularia nodosa 160 7-0-Rutinoside 164 Scutellarein 156, 157 Rutinosyl-galactose 172 -, -7-glucosid 200 Rynchophyllan 475 -, -glucuronid 173, 200 Rynchophyllin 473 Scutellaria altissima 200 Rynchospora alha 190 Scutellaria-Arten 173, 174 Scutellarin 200 Secologanin 469,501 Saccharin 164 Selendioxid s. selenium dioxide Saccharomyces carlsbergensis 112 Selenite 616,617 Saccharomyces cerevisiae 112 Selenium 316, 323,428 Saccharose 378 Selenium dioxide 79, 108, 133, 197,206,416, Sakuranetin 157,158,165 500 -, -5-0-glucosid 157, 165 Selina-4(l4),7(l1)-diene 343 686 Sachverzeichnis. Subject Index

Sakuranin 165 Sodium borohydride 16,39,50,51,70,86,87, Selinane 309 329,333,338,341,366,367,411,416,421, ß-Selinene 352 429,431,439,441,473,476,478,481,482, ö-Selinene 325,343,352 487,488,489,502,503,505,507,509,513, Semiquinones 564, 565 535 - from catechol 533, 534, 544 Sodium bromide 13,14 Sephadex 538,571 Sodium carbonate 72,81,386,388 Sepia officinalis (cuttlefish) 554,555 Sodium chloride 542, 543 Sepiomelanin 554f, 565 Sodium dithionite 554 -, decarboxy1ated 557 Sodium ethoxide 196, 332 -, methylated 557 Sodiumhydride 10,17,25,228,229,230,235, Sepiomelanoprotein 555 238,239,241,244,256,299,307,333,365 L-Serine 102 Sodium hydrogen carbonate 23, 51, 136, 198, Serosangineous inhibition 379 247,249,250,261,262,330 Serratia mareseens 112 Sodium hydrogen sulfide 50 Sesquiterpene alcohols 114 Sodium hydrogen sulfite 199 -, esters 78 Sodium hydroxide 47,65,69,72,80,173,194, -, gas-liquid chromatography 102 198,201,220,259,266,330,331,335,369, Sesquiterpenes 283f 404,556,565,567,571 -, biosynthesis 349 Sodium iodide 14,79,204,368 [2,3]-Sigmatropic rearrangement 17 Sodium methoxide 15,36, 191, 194, 195, 198, Silberacetat 191 199,200,203,204,205,257,269,271,300, Silbercarbonat 194, 199,200,201 308,311,367,369,412,423,443,447,452 Silbemitrat 339,402,418 Sodium nitrite 13, 14, 15, 16 Silberoxid 194, 195, 196, 198, 199, 201, 414, Sodium periodate 24, 75, 81, 106, 138, 410, 415,417,448 428,431,432,433,434,435 Silberperchlorat 192 Sodium-potassium alloy 311, 312 Silbersalze 193,200 Sodium sulfate 404 Silver- s. Silber• Solanaceeen-Familie 171 Silena schafta 185 Solanum-Arten 167 Silene-Arten 188 Solanum tuberosum 170, 171 Silene suaveolens 188 Sophorabiose - Neohesperidose 159, 163, Silica 123 164, 165, 192 Silicage1 101, 232, 259, 263, 335, 339, 381, -, -acetat 192 382,383,386,387,388,393,395,400,402, -,-heptaacetat 192 403,418,424,426,445 Sophorabiosid 165,166,201 Silky fowl 562 Sophorajaponica 162, 165, 166 Sily1ating agents 11 Sophoricosid 202 Sily1esters 4, 6 Sophorose - 2-0-(ß-D-Glucopyranosyl)• Sinapinsäure-Ester 185 glucopyranose 159, 166, 167, 170, 171, Sisymbrium alliaria 187 175, 192 Skin carcinogenesis 379 Sophorotriose 170, 172 Skin inftammation 113 Sophorotrioside 171 Skin irritation 113 Sorbus aucuparia 167 Snapdragons 64 Sparattosperma vemicosum 161 Sodium 181,316 Spartium junceum 189 Sodium acetate 28, 102, 173, 196,203, 241, Spectroscopical investigations 247,249,272,329,412 Hinesol derivatives 340 Sodium amide 228,229,231,232,235 Melanins 562 Sodium azide 15,38,39,46,49,51 Oxidation of dihydroxindol derivatives Sodium bicarbonate s. sodium hydrogen 526 carbonate Oxidation of dopa 525, 553 Sodium bismuthate 435 Oxidation products oftyrosin 553 Sachverzeichnis. Subject Index 687

Prezizaene 348 Stilbens, biosynthesis 226 ß-Vetivone 335 Stipa-Arten 191 Sphaerobiosid 163 Streptomyces aureofaciens 274 Sphaeropsidales 147 Streptomyces lincolnensis 562 Sphenomeris chusana 187 Streptomyces olivaceus 587 Spiraea ulmaria 202 Strychnin 469,497,500 Spiraeosid 156,202 Strychnos-Typ von Indolalkaloiden 470 Spiroaurenone 284, 285 7-Styryl-pyranopyrandiones 255 Spiro[4.5]decadienones 368 Substantia nigra 567 -, synthesis 299 Succinate 605, 607 Spiro[4.5]decanes 308,349, 351f Succinyl-CoA 604, 605, 608 -, derivatives, mass spectra 296f Succisa pratensis 188 -, naturally occurring 353f Sulfamic acid 28 -, sesquiterpenes 283f Sulfate esters 28 -, syntheses 298f,368f Sulfenic-acetic anhydride 28 Spiro[4.5]decanonecarboxylicester 307 Sulfenic acids 28, 33 Spiro[4.5]decanones 305, 306, 369 -, in sulfoxide rearrangement 33 Spirodecene 370 -, reaction with olefins and mercaptans 32 Spiro[4,5]decyl cation 371 Sulfonic acids 28 Spirodela 186 Sulfoxide rearrangement 28, 30, 33 Spirodela-Arten 190 Sulfur 316 Spirodela oligorrhiza 182 Sulfuretin 157,158 Spiro-cyclization 304 -, -O-glucosid 157 Spirodienes 351 Sulfuricacid 13,28,75,78,81,83,90,92,97,98, Spirodienone 345 101,173,180,228,229,253,255,311,312, Spiro[3.5]nonenone 368 371,388,389,404,440,441,444,538 Spiro[5.5]undecanes 296 Sulfur trioxide 335, 364 Spirovetivanes 309f, 327, 328, 342, 347, 352, Sulphurous acid 524 361,362 Sulphydryl compounds 553 -, syntheses 328f,368f Süßersatzmittel 164 Squid ..... Loligo opalesens 554 Süßkraft 164 Stannic chloride 301,302,303,320 Sweet flag ..... Acorus calamus 285, 358, 359, Stannous chloride 42 360 Stannous esters 4 Sweet flag oil 284,291 Stärke, lösliche 186 Swertia japonica 180, 189 Stearic acid 427 Swertiajaponin ..... Isoorientin-7-0-methyl• Sterigmatocystins 119f, 122, 123, 134, 146 äther 178, 180 -, biogenesis 140f, 143, 145 Swertisin 178, 180 -, p-brombenzoate derivatives 127, 133 Syncarcinogenic action 457 -, carcinogenic activity 120 -, catalytic hydrogenation 124 -, infrared spectra 124 Tabersonin 509 -, me1ting points 122 Tamarindus indica 189 -, monomethyl ether 124,127,128 Taurine 557,558 -, NMR-spectra 126, 130 Teline linifolia ..... Cytisus linifolia 189 -, optical rotation 122 Tenebrio molitor 524 -, stereochemical forms 127 Terniflorin 176 -, structural elucidation 124f Tetraacetic acid 222,226,231,247,251,259 -, toxicity 147 -, -ester 232 -, ultraviolet spectra 124 - -, hemithioketal protected 232 -, X-ray cristallography 127, 133 -, -methyl ester 232 Sterols 66, 68 Tetraacetic lactone 223, 226, 233, 234, 236, Stickstoff 197,404 240,243,244,251,252,255,258,259 688 Sachverzeichnis. Subject Index

1,3,4,6-Tetra-O-acetyl-ß-D-glucopyranose Thalictrum-Arten 189 192, 193 Thiazepine 12 1,2,3,4-Tetra-O-acetyl-ß-D-glucose 191 1,3-Thiazines 13 2-(Tetraacetyl-glucosido)-2-benzoyl- Thiazolidine ring cleavages 35, 38, 43, 45 phloracetophenon 203 Thiazolidine ring of penicillins 3, 23 5,7,3' ,4'-Tetraacetyl-quercetin 200 Thiazolidine ring, Raney-nickel desulfuri- 3,5,3' ,4' -Tetrabenzoylquercetin 200, 202 zation 47 3,7,3',4'-Tetrabenzoylquercetin 202 Thick layer chromatography 389, 391, 392 Tetracyclic products 265 Thienyl acetic acid 37 Tetracycline 274 Thin layer chromatography Tetradecanoic acid 395 Croton oil fractions 383, 388, 389, 391, 12-0-Tetradecanoylphorbol-20-acetate 412 426,444,452 Tetrahydroalstonin 481,482 Diterpenes 444, 453 Tetrahydro-deoxo-aflatoxinB 1 128,129,130, Mycotoxins 123, 124 134 Phorbol derivatives 441,452 Tetrahydrofolic acid 619 Roridins 101 Tetrahydrofuran 10, 101,228,232,257,294, Verrucarins 101 301,411,491 Thioglycollic acid 530,561 Tetrahydrofuro[2,3-b]benzofuran 132, 133, Thioketal derivatives 367 139, 147 Thioketals, formation 324 Tetrahydroharman-Derivat 510 Thiol groups, oxidation 531 Tetrahydro-4-hydroxy-6-methoxy-furo[2,3-b] Thiols 21,600,602,608,609,611,614,617, benzofuran 126, 133, 134, 136 619,620 1,2~,ßH, 7-Tetrahydrophorbol-12, 13-di- Thionyl chloride 28,29, 37, 44, 82, 92, 105, decanoate 420 335,341,418,435 Tetrahydrororidin A 90 Thioprotein 609,611,617 -, Monodehydroderivat 90 Thioredoxins 600 Tetrahydrororidinic acid 104 Thiosulfate ion, nucleophilic reactivity 588 4,6,3' ,4' -Tetrahydroxy-auron-6-rutinosid 163 Thypafatifolia 165 Tetrahydroxy-biphenyls 533, 536 Tigliane -+ 1,laa.,1 bß,2,3,4,4aß,6,7,7aa.,7bp, 5,5' ,6,6' -Tetrahydroxybiphenyl-3,3' -ylene• 8,9,9aa.-Tetradecahydro-l, 1,3~,61;,8a.­ dialanine 552 pentamethyl-5H-cyclopropa[3,4]benz• 2' ,4' ,6',4-Tetrahydroxy-chalkon-2' -O-gluco- [1.2-e]azulene 405,409, 428 sid -+ Isosalipurposid 202, 203 Tiglic acid 395 5,5' ,6,6' -Tetrahydroxyindigo 540 Tiglophorbol 431,432,433,434,444 Tetrahydroxynaphthalene 271 -, -13,20-diacetate 433 3,5,7,9-Tetraketo acids Tiglophorbol B 435 cyclizations 261,262,263 12-0-Tiglyl-phorbol-13-butyroate 427 syntheses 236f 12-0-Tiglyl-phorbol-13-dodecanoate 427 3,5,7,9-Tetraketo esters Tilia-Arten 160 cyclization 261 Tilia argentea 174 syntheses 236f Tilia japonica 200 Tetraketones 236,237,239,240 Tilianin 200 -, cyclization 259,260 Tilirosid 174, 175 -, syntheses 234f Tollens' reagent 404,408,416,417,431,433, 5,7,3',4'-Tetramethylguaijaverintriacetat 155 434 4,9,13,20-Tetra-0-methylphorbol-12-acetate Toluene 101 414 p-Toluene-sulfonate derivative 312 Tetramethylquercetin 155 p-Toluenesulfonicacid 16,30,37,50,51,411, Tetramethyl silane 76, 126 416,433,434,435,437,442,448,498,505 Tetramethyl urea 30 -, chloride 51,320,330,331,365 Tetrapyranopyrantetraone 240,264 p-Toluolsulfosäuremethylester 196 Teucrium montanum 160 Tomatoes 64 Sachverzeichnis. Subject Index 689

Tosylierung 180,483 Trichothecane derivatives, gas liquid chro- Toxicity 113,147,380,383,388,392,398,456 matography 102 Tragopogon sp. 183, 188 -, incorporation of mevalonic acid 107 Transacylierungen 201,202 -, macrocyclic esters 74f Transacylierungsmethode 199,200 -, toxicity 113 Transesterification, acid-catalyzed 398, 399 -, trimethyl silyl esters 102 Transesterification, base-catalyzed 404 Trichothecane ketones 83 Transpeptidase catalyzed reaction 17 Trichothecene alcohol 114 Transpeptidase inhibition 18,20 Trichothecene derivatives, biological acti- Trema aspera 180, 190 vity 112 Tremasperin 180 Trichothecin 75, 107, 109 -, acetate 180 Trichothecium roseum 109, 110 Triacetic acid 221,222,229,246 Trichothecium sp. 74, 109 -, chloride 246 Trichothecolone 75, 78, 83, 110 -, ester, total protected 232 -, NMR-spectrum 79 -, ethyl ester 228, 229 Tricyclovetivane - Zizaane 346 -, methyl ester 228 Tricyclovetivan-6-one 346 -, synthesis 228 Tricyclovetivan-7-one 346 Triacetic lactone 226,228,229,234,239,243 Tricyclovetivene 317,318 -, -3-methyl derivative 226, 228 Triethylamine 10,11,12,13,16,25,32,33,42, 12ß, 13,20-Triacetoxy-7ß,9-dihydroxy-4, 7- 44,307,505 epoxy-6,7-seco-l-tigliene-3,6-dione 429 Triethyl phosphite 32,502 12ß, 13,20-Triacetoxy-9-hydroxy-4-oxo-3,4- Triftuoressigsäure s. triftuoroacetic acid seco-l,6-tigliadien-3-al 428 Triftuoroaceticacid37, 39,41,42,49,82,169,174, 2,3,4-Tri-O-acetyl-Il-D-xylosylbromid 193 234,271,293,294,304,330,331.351.483 Triäthylamin s. triethylamine Trifolium prutense 176 Triäthylphosphit s. triethyl phosphite Trigonella phoenum graecum 184, 189 3,5,3' -Tribenzoyl-quercetin 200 5,7,4'-Trihydroxy-ftavanon-7-0-glucosid - 2,3,4-Tri-O-benzoyl-Il-L-rhamnosylbromid Prunin 199 192 5,7,4' -Trihydroxyftavon-8-C-6" -O-acetyl• Tribulosid 175 (4-0-1l-L-rhamnopyranosyl)-D-gluco• Tribulus terrestris 175 pyranosid - Cratenacin 186 Tri-n-butyl-phosphine 588 7,3',4' -Trihydroxyflavon-7-0-glucosid 197 Trichloroethanol 39 5,7,4' -Trihydroxy-isoftavon-7-0-mono• 2,2,2-Trichloroethoxycarbonyl group 4 glucosid - Genistin 194 2,2,2-Trichloroethyl 6-phenoxy-acetamido- 2' ,4' ,6' -Trihydroxy-4-methoxy-chalkon-4'• penicillanate II neohesperidosid 197 -, (S)-sulfoxide 28 2S-3' ,5-7-Trihydroxy-4' -methoxyftavanon- Trichoderma 109 7-0-rutinosid 162 Trichodermin 75, 78 2,4,5-Trihydroxyphenethylamine 569, 570 -, NMR-spectrum 79 5,7,3' -Trihydroxy-3,6,4' -trimethoxyftavon -, total synthesis 99f 194 Trichodermol s. Roridin C 5,7,4' -Trihydroxy-3,6,3' -trimethoxyftavon Trichodiene 110, 111 194 Trichodiol A 110 4,9,20-Trihydroxy-15, 16, 17-trinor-l ,6- Trichophyton 112 tigliadiene-3,13-dione 440,443 Trichophyton asteroides 112 1,3,8-Trihydroxyxanthone 124 Trichosiderin 571,572 -, -4-carboxylate 125 Trichothecane 78 3,5,7-Triketo acids 247 Trichothecane derivatives 66, 68, 111 -, cyclizations 234,246,248,251,263 -, acid catalyzed rearrangement 83 -, syntheses 231 -, biosynthesis 103f 3,5,7-Triketo esters 247,249,251 -, detections 101 -, acyclic protected, cyclizations 253

Fortschritte d. ehern. org. Naturs!. XXXI 44 690 Sachverzeichnis. Subject Index

3,5,7-T riketo esters, cyclizations 249, 251, 271 Precursors oftrichothecanes 103 --, syntheses 231 Propionaldehyde 592 1,3,5-Triketones 232,236,237,246 Ribonucleotide reductase 600 --, carboxylation 231 Roridin A 105 --, lithium salts 232 Sodium borohydride 416 --, syntheses 230f Trichodiene HO Triketone, unsaturated 243 Trichodiol A HO Trimethoxybenzoylchlorid 488 Trichothecolone HO Trimethoxy-ftavonole 156 Verrucarinic acid 105 1,3,8-Trimethoxy-xanthone-4-carboxylic Verrucarinolactone 105 acid 125 Verrucarol 107, 108 Trimethylamine 547,558 Water 601 2,3,4-Tri-O-methyl-arabinose 155 Wortmannin 99 2,3,5-Tri-O-methyl-arabinose 155 Tritium-markierte Verbindungen s. tritium- 2,3,5-Tri-0-methyl-arabonsäure 155 labelIed compounds Trimethylarsine 617 6-Tritylaminopenicillanic acid 11 3,4,6-Tri-O-methyl-ß-D-glucose 164 Tritylchloride 414,415,448 1,6,7-Trimethyl-4-isopropylnaphthalene 287 Trityl esters 4 Trimethyl-phenyl-ammonium bromide 138 Trityl group 4 4,13,20-Tri-0-methylphorbol-12-acetate 0-Trityl-ß-I ,2,3,4-tetra-0-acetyl-ß-D-glu- 414,415 cose 192 Trimethylphosphit 33 Trollius europaeus 189 2,3,4-Tri-0-methyl-L-rhamnose 164 Trypsin 379 Trimethylsilyl acetoacetate, lithium salt 234 Tryptamin 470, 483, 507 Trimethyl silyl esters 102 Tryptophan 469,555 Triphenyl germanate(II)-ion 588 Tuberculariaceae 64 Triphenyl-methyl-lithium 320 Tubofolidin 494 Triphenyl-methyl-natrium 497 Tumefaction 379 Triphenylphosphin 306 Tumor cells of mice, growth-inhibition 112 Triphenylphosphin-ylid 300, 367 Tumorigenesis of mouse skin 379 Triphenyl phosphite 418 Tumor rate 384,386,390,401,456 Triphenyl phosphonium bromide 368 Tumor yield 384,386,390,401,456 Triphenyl stannate(II)-ion 588 Turkey X disease 120 Tripolyphosphate 591 Tyndall blues 561 Tripyranopyrantetraone 239, 263 Tyramine 522 --, aromatization 264 Tyrosinase 522,524,526,529,530,531,532, Triticum aestivum 182 539,543,545,551,552,563 Triticum-Arten 191 Tyrosine 522,523,524,526,527,528,529,530, Tritium-Iabelled compounds 531,532,539,543,546,552,553,554,559, 2-Aminoäthanol 599 560,561,571,574 Coenzyme of dioldehydrase 592, 594 Tyrosine-melanin 547 Dopa 551,558,561 Tyrosylglycin 553 12,13-Epoxy-trichoth-9-ene 110 [2-3H]-Geranyl phosphate 110 [2-3H,2-14C]-Geranyl pyrophosphate 109 Ulein 488,490,491,492 Kinetic isotope effect 107 Ulex-Arten 189 2-(3H]-Lanosterol 99 Ullmann xanthone synthesis 139, 140 Melanin 559 Ulmaceae 190 Methyleneglutarate mutase 605 Ultraviolett-Spektren s. UV -Spectra Methylsuccinic acid 105 Ustilago maydis 537, 563 Mevalonates 105, 107, 108, 109, 110 Ustilago melanin 537,563 2-[3H]-2-[14C]-Mevalonic acid 99 UV-ftuorescenceofaftatoxins 123,124 Phorbol derivatives 414,416 UV -irridations of penicillin sulfoxides 25 Sachverzeichnis. Subject Index 691

UV-Spectra Verrucarin A, biosynthesis 103.104 Aflatoxin-B I 128, l32 -, cytostatic activity 112, 113 Aflatoxin-G I l31 -, effects on chromosomes 113 Aflatoxin-MI l32 -, hexahydro derivative 84 Aspertoxin 128 -, hydrolysis 84 Azulenes 428 -, insecticidal activity 113 Benzazulenes 428 -, o-iodobenzenesulfonate, X-ray inv. 87 Bicyc1o[1 O.1. 10)-tridecanyl-l3-acetate 408 -, IR-spectrum 84 Catechol-melanin 535 -, LDso 113 Croton oil fractions 388, 396f -, mono-O-acetyl derivative 84 Cyclization product of phenyl trioxohep- -, NMR-spectrum 76,77 tanoic acid 247,250 -, oxidation 86 Cyc1opropan ring 420 -, production 65 20-Deoxy-tetrahydrophorbols 420 -, structure elucidation 84f 5,7-Dimethoxycoumarin 129 -, thin layer chromatography 101 5,7-Dimethoxycyc1openteno[c)coumarin -, UV-spectrum 84,90 129 Verrucarin B 64,65,66,74,89,95, 111 Glutacondialdehyde 430 -, cytostatic activity 112, 113 Guaiazulene 428 -, fungistatic affect 112 Hinesol derivatives 325 -, hydrolysis 73, 88 Hydroxycholestadienone 430 -, IR-spectrum 88 Melanins 562 -, LDso 113 Myrochromanol 69 -, NMR-spectrum 76,77,88 Myrochromanone 69 -, production 65, 88 Oxidation of dopa 570 -, structure 88 Phorbol 405,407,409 -, thin layer chrOOlatography 101 4cx-Phorbol 447,448 Verrucarin C 67 Phorbol derivatives 408f -, thin layer chromatography 101 Roridinic acid 90 Verrucarin D 67 Roridins 90, 100, 101 -, thin layer chromatography 101 Selinene 325 Verrucarin E 66, 68, 70f Sterigmatocystin 124 -, biosynthesis 102 Tetrahydrodeoxoaftatoxin-B I 129 -, Kuhn-Roth oxidation 102 Verrucarin A 84,90 -, mono-O-acetyl derivative 71,72 Verrucarin E 102 -, synthesis 72, 100 Verrucarins 100, 101 Verrucarin F 66 Verrucarol 75 -, thin layer chromatography 101 Verrucarin G 66,74 Yaccinium bracteatum 188 -, thin layer chromatography 101 Valencane 345 Verrucarin H 65 Valencene 342,352 Verrucarin J 65,66,74,88,89,95,111,113 Valeranone 345 -, hydrolysis 73, 89 Valeriana wallichii 176 -, LDso 113 Vanillin 388,389,444 -, NMR-spectrum 76,77,89 Velbanamin 502,505 -, octahydroderivative 89 Verbascum phJoimoides 160, 162 -, production 65 Verbenaceae 173,190 -, structure 89 Veronicastrosid 161, 164, 195 -, thin layer chromatography 101 Veronicastrum sibiricum 161 Verrucarinicacid 85,86,87,92,105,106,107, Verrucarin A 64,65,66,74,88,89,95,111 111 -, antibacterial activity 112 -, phenylhydrazide 84 -, antifungal activity 112 Verrucarinolactone 73,84,85,86,88,90,92, -, antiviral activity 112 103,104, 105

44' 692 Sachverzeichnis. Subject Index

Verrucarinolactone NMR-spectrum 85 IX-Vetivone 317,327,342,343 Verrucarins 63 f ß-Vetivone 284,285, 314f, 318, 319, 322, 325, -, antibiotical activity 112, 114 327,328,329,331,336,342,343,346,362, -, antifungal properties 112 363,364 -, biological activity 112 -, degradation 315,321,323 -, biosynthesis 102f -, dehydrogenation 316 -, chemical transformations 68 -, reduction 317 -, chromatography 65 -, stereochemistry 323,324 -, circular dichroism 87 -, synthesis 329,330, 334f, 340, 366f -, cytostatic activity 112 Vicenin 1 184, 185 -, hydrolysis, base catalyzed 73 Vicenin 2 184 -, liquid-liquid partition 65 Vicenin 3 184,185 -, mass spectra 83 Viciafabra 539 -, methodsofassay 100f Vicia hirsuta 168 -, NMR-spectra 76,77,90 Vicianose -+ 6-0-(IX-L-Arabinopyranosyl)-ß- -, optical rotation 66 D-glucopyranose 159, 169 -, production and isolation 65 Vicia sativa 169 -, structure 68f Vicianin 169 -, thin layer chromatography 101 Vinblastin 502 -, total synthesis 99f Vinca herbacea 166 -, toxicity 112, 113 Vinca major 166 -, UV-spectra 100, 101 Vinca minor 166 Verrucarol -+ 4ß, 14-Dihydroxy-12, 13-epoxy• Vincamin 501,513 ~-trichothecene 73f, 78, 81, 83, 84, 86, Vincristin 502 87, 88, 89, 90, 94, 95, 96, 103, 104, 105, Vindorosin 510 107, 108, 109, 110, 111 Vinyl bromide 136 -, chlorohydrin 75 Vinylmagnesium bromide 302 -, conformation 81 Violaceae 190 -, dihydro derivative 75, 79 Violanthin 185,205 -, -4,15-di-o-mesyl derivative 79 Viola tricolor 185, 190 -, epoxide 107 Violets 64 -, gas liquid chromatography 102 Viscontini-Abbau 185 -, hydrogenation 79 Viscum album 169 -, NMR-spectrum 76,77,79 Vitaceae 190 -, rearrangement 83 Vitamin B12 584,597,598 -, structure 78,80 -, chemistry 584f -, thin layer chromatography 101 -, ESR-spectra 589, 598 Versicolorin C 141,142,144 -,modelcompounds 584,587~597 Vertebrates 526,527, 528f Vitex-Arten 190 Vesicant activity 380 Vitexin 178,179,183,184,186 Vestia lycioides 167 -, 14C-labelled 186 Vetiselinene 343 -,7,4-Di-O-methyl-tetraacetyl-derivat 180 Vetiselinenol 343 -, Mono-methy1äther 180 IX-Vetispirene 328, 340, 341, 344, 346, 361 -, -4'-O-rhamnosid 182 ß-Vetispirene 328,344,361,364 -, -O-xylosid 183,184, 186 Vetivanes 317,318,327,328 Vitexin-Typ 205 Vetivane sesquiterpenes 284 Vitex lucens 179,183,184 Vetivazu1ene 315,316,317,322,327,328 Vitiligo 528 ß-Vetivenene 344 Vitis cinerea 190 y-Vetivenene 344 Vetiveria zizanoides 354, 361, 362 Wagner-Meerwein rearrangement 344, 348, Vetiver oil 316, 318, 327, 342, 343, 344, 346, 351 347,348 Waiden-Umkehr 193 Sachverzeichnis. Subject Index 693

Walker carcinoma 113 Triehodermol p-bromobenzoate 75 Wasser s. water Verruearin A p-iodobenzenesulfonate 87 Wasserstoffperoxid s. hydrogen peroxide W ortmannin 99 Water 16,24,36,37,48,49,74,82,83,91,105, Xylene 312 106,107,135,173,249,250,253,254,256, 2-0-(ß-D-Xylopyranosyl)-ß-D-galaeto• 261,263,264,266,272,286,308,330,331, pyranose-+ Latyrose 159,167,168,171 335,365,367,368,383,388,389,390,401, 2-0-Q(-D-X ylopyranosyl-D-glucopyranose 402,403,404,421,428,430,431,444,446, 193 453,533,537,587,601,605 2-0-(ß-D-Xylopyranosyl)-ß-D-glueopyra• Weizenkeime 185 nose -+ Sambubiose 159, 167, 168, 171, Wittig-Olefinierung 517 183, 193 Wittig reaction 99 2" -O-ß-D-Xylopyranosylvitexin 183 Wolffia-Arten 190 D-Xylose 155, 183 Wolff-Kishner reduction 301, 302,475,494, Xylosidierung 184 513,516 Xylosyl-glueopyranosyluronsäure 159 Wortmannin 65,67,68,99 Xylosyl-glueose-Disaceharid 167 Wyomin -+ Isoorientin-7-0-rutinosid 182 3-Xylosyl-7-glueosid 159 O-Xylosylvitexin-nonamethyHither 183 Xanthones 244, 264, 265, 272 Xanthone system 139, 141 Xanthophanic acid 242, 243 Yeast extraet 65 Xanthophanic enol 268, 269 Yohimbin 483,485,486,487 Xanthorhamnin 170 ß-Yohimbin 485,487 Xanthoxylum-Arten 160 Y oshida sarcollla 11 ~ X-rayanalysis Aeorenone 291 Aeorone 290 Zeisel-determination 548, 549 Aflatoxin-B2 131, 133 Zelkowa serrata 181, 190 Aflatoxin-G I 131,133 Zimtsäure 181 Hetaeillin 6 Zine 30,36,39,40,41,79,109,135,366,367, Hinesol derivatives 336 368,418,441,449,450,451,516,586 Khumisyl p-bromobenzoate 346 -, binding by eumelanins 554 ß-Lactam nitrogen 45 Zinc carbonate 136, 137, 138 Lumiphorbol triacetate 450 Zine chloride 131 Melanins 562, 563 Zincions 525,526 Penicillin sulfoxides 24 Zinc silicate 102 Phorbol 408,409 Zitronenschalen 180 Phorbol derivatives 409,411, 413, 416 Zizaane -+ TricycJovetivane 346 Poriolid 177 Zizaenes 317,347,348,350 Sterigmatocystin-p-bromobenzoate 127, -, biosynthesis 346 133 Zizanoic acid 346 Fortschritte der Chemie organischer Naturstoffe Progress in the Chemistry of Organic Natural Products

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Contents.' M. J. Cormier, J. E. Wampler, K. Hori, Bioluminescence: Chemical Aspects. - L. Jaenicke, D. G. Müller, Gametenlockstoffe bei niederen Pflanzen und Tieren. - J. Polonsky, Quassinoid Bitter Principles. - B. Franck, H. Flasch, Die Ergochrome (Physiologie, Isolierung, Struktur und Biosynthese. - H. D. Locksley, The Chemistry of Biflavanoid Compounds. - W. Keller-Schierlein, Chemie der Makrolid-Antibiotica. - R. Tschesche, G. Wulff, Chemie und Biologie der Saponine. - Author Index / Namenverzeichnis. - Subject Index / Sachver• zeichnis.

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