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The Biogenesis and Chemistry of Sesquiterpene Lactones 321

The Biogenesis and Chemistry of Sesquiterpene Lactones 321

The Biogenesis and Chemistry of Lactones 321

Acknowledgements: Parts of this work were supported by Grant Number 1-R01-CA- 19800, awarded by the National Cancer Institute, DHEW and by a grant from the National Science Foundation (DEB-76-20585). We are indebted to Professor WERNER HERZ whose contributions to this review went far beyond his editorial duties.

References

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357. GRIECO, P. A., M. NISHIZAWA, T. OGURI, S. D. BURKE, and N. MARINOVIC: Sesqui• terpene Lactones: Total Synthesis of ( ±)-V ernolepin and ( ±)-Vernomenin. 1. Amer. Chern. Soc. 99, 5773 (1977). 358. GRIECO, P. A., T. OGURI, C. L. J. WANG, and E. WILLIAMS: Stereochemistry and Total Synthesis of (±)-Ivangulin. J. Organ. Chern. (U. S.A.) 42, 4113 (1977). 359. GRIECO, P. A., Y. OHFUNE, and G. MAJETICH: Pseudoguaianolides. Stereospecific Total Synthesis of (±)-Ambrosin, (±)-Damsin, and (±)-Psilostachyin C. J. Amer. Chern. Soc. 99, 7393 (1977). 360. GRIECO, P. A., Y. YOKOYAMA, S. GILMAN, and Y. OHFUNE: Conversion of Ketones into Lactones with Benzeneseleninic Acid and Hydrogen Peroxide (Benzeneperoxy• seleninic Acid): A New Reagent for the Baeyer-Villiger Reaction. Chern. Commun. 1977,870. 361. GRIFFIN, T. S.: Acid Color Reactions and Structures of Sesquiterpene Lactones. From Diss. Abstr. Int. B 31, 5875 (1971); Chern. Abstr. 75, 77057e (1971). 362. GRIFFIN, T. S., T. A. GEISSMAN, and T. W. WINTERS: The Chemistry of a Structurally Diagnostic Color Reaction of Xanthinin and Related Sesquiterpene Lactones. Phytochem. 10,2487 (1971). 363. GUERRERO, C., E. DIAZ, M. MARTINEZ, J. TABOADA, S. MIRANDA PLATA, M. GONZA• LEZ DIDDI, and J. TELLEZ: Determination of the Structure of Euparhombin and Its Cytotoxic Activity in Two Cellular Lines. Rev. Latinoamer. Quim. 8, 123 (1977). 364. GUERRERO, J., R. ENRIQUEZ, 1. SALAZAR, and E. DIAZ: Desplazamientos Inducidos Por Lantanidos En RMP De Guayanolidos y Pseudoguayanolidos. Rev. Latinoamer. Quim. 5, 169 (1974). 365. GUERRERO, C., A. IRIARTE, E. DIAZ, J. TABOADA, M. GONZALEZ DIDDI, and J. TELLEZ: Determinacion De La Estructura y Estereoquimica De La Elemenolida Verafinina C y Aislamiento De La Verafinina B, Dos Substancias Citotoxicas Aisladas De Verbesina aff. coahuilensis. Rev. Latinoamer. Quim. 6,119 (1975). 366. GUERRERO, C., M. MARTINEZ, E. DIAZ, and A. ROMO DE VIVAR: Estructura Y Estereoquimica De La Verafinina, Una Nueva Elemenolida Aislada De Verbesina aff. coahuilensis Gray. Rev. Latinoamer. Quim. 6, 53 (1975). 367. GUERRERO, C., A. ORTEGA, E. DIAZ, and A. ROMO DE VIVAR: Estructura De La Viguiestenina y De La Desacetil Viguiestenina. Rev. Lationoamer. Quim. 4, 118 (1973). 368. GUERRERO, C., M. SANTANA, and J. ROMO: Estudio Quimico De La Viguiera augustifolia HBK Blake. Rev. Latinoamer. Quim. 7, 41 (1976). 369. GUY, M. H. P., G. A. SIM, and D. N. J. WHITE: Molecular Mechanics Calculations on Lactones; An Interpretation of the Preferential C-8 Relactonization of Germa• cranolides Containing C-6 and C-8 Lactonizable ex-Oxygen Functions. J. Chern. Soc. Perkin Trans. II 15,1917 (1976). 370. GOREN, K. C., A. ULUBELEN, and S. OKSOZ: Compositae: Santonin from Artemisia fragrans. Phytochem. 11,3542 (1972). 371. HABIB, A. A. M., and A. M. METWALLY: New Sesquiterpene Keto Lactone from Se• necio. Planta Med. 23, 88 (1973); Chern. Abstr. 78, 156620y (1973). 371 a. HALL, 1. H., K. H. LEE, E. C. MAR, C. O. STARNES, and T. G. WADDELL: A Proposed Mechanism for Inhibition of Cancer Growth by Tenulin and Helenalin and Related Cyclopentenones. J. Medicin. Chern. 20, 333 (1977). 372. HAMILTON, J. A., A. T. MCPHAIL, and G. A. SIM: The Structure of Acetylbromo• geigerin. Proc. Chern. Soc. 1960, 278. 373. HARLEy-MASON, J., A. T. HEWSON, O. KENNARD, and R. C. PETTERSEN: Isolation of Centaurepensin, A Guaianolide Sesquiterpene Lactone Ester Containing Two Chlorine Atoms; Determination of Structure and Absolute Configuration by X-Ray Crystallography. Chern. Commun. 1972, 460.

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Germacrane Type from Artemisia balchanorum, H. Krasch. Collect. Czech. Chern. Comm. 26,2612 (1961). 392. HERZ, W.: Sesquiterpene Lactones in Compositae. In: Pharmacognosy and Phyto• chemistry (WAGNER~ H., and L. HORHAMMBR,. eds.). Wien: Springer. 1971. Chern. Abstr. 76, 59761 w (1972). 393. - Biogenetic Aspects of Sesquiterpene Lactone Chemistry. Israel J. Chern. 16, 32 (1977). 394. - Pseudoguaianolides in Compositae. In: Recent Advances in Phytochemistry (MABRY, T. J., R. E. ALSTON, and V. C. RUNECKLES, eds.), Vol. I, p. 229. New York: Appleton-Century-Crofts.1968. 395. - Pseudoguaianolides in Compositae. In: Chemistry in Botanical Classification (Nobel Foundation, Stockholm), Nobel Symposium 25. New York and London: Academic Press. 1973. 396. - Constituents of Helenium Species. XII. Sesquiterpene Lactones of Some South• western Species. J. Organ. Chern. (U. S. A.) 27,4043 (1962). 397. - In: Biology and Chemistry of the Compositae (HEYWOOD, V., B. L. TURNER, and J. B. HARBORNE, eds.). New York and London: Academic Press. 1978. 398. HERZ, W., G. ANDERSON, S. GIBAJA, and D. RAuLAIs: Sesquiterpene Lactones of Some Ambrosia Species. Phytochem. 8, 877 (1969). 399. HERZ, W., K. AOTA, and A. HALL: New Pseudoguaiano!ides from Hymenoxys Species. A New Type of Lactone Closure. J. Organ. Chem. (U.S.A.) 35, 4117 (1970). 400. HERZ, W., K. AOTA, A L. HALL, and A SRINIVASAN: Antileukemic Pseudoguaiano• !ides from Hymenoxys grandiflora (T. & G.) Parker. Application of Lanthanide• Induced Shifts to Structure Determination. J. Organ. Chern. (U. S. A.) 39, 2013 (1974). 401. HERZ, W., K. AOTA, M. HOLUB, and Z. SAMEK: Sesquiterpene Lactones and Lactone Glycosides from Hymenoxys Species. J. Organ. Chern. (U. S. A.) 35, 2611 (1970). 402. HERZ, W., and S. V. BHAT: Woodhousin, a New Germacranolide from Bahia wood• housei (Gray) Gray. J. Organ. Chern. (U. S. A) 37, 906 (1972). 403. -- Isolation and Structure of Two New Germacranolides from Polymnia uved£llia (L.) L. J. Organ. Chern. (U. S. A.) 35, 2605 (1970). 404. -- Maculatin: An Isomer of Uvedalin Epoxide from Polymnia maculata. Phyto• chern. 12, 1737 (1973). 405. HERZ, W., S. V. BHAT, H. CRAWFORD, H. WAGNER, G. MAURER, and L. FARKAS: Bahifolin, A New Sesquiterpene Lactone, and 5,7-Dihydroxy-3,3',4',6-Tetramethoxy• flavone, a New Flavone, from Bahia oppositifolia. Phytochem. 11, 371 (1972). 406. HERZ, W., S. V. BHAT, and A. L. HALL: Parthemollin, A New Xanthanolide from Parthenice mol/is Gray. J. Organ. Chern. (U. S.A.) 35,1110 (1970). 407. HERZ, W., S. V. BHAT, and A SRINIVASAN: Berlandin and Subacaulin, Two New Guaianolides from Berlandiera subacaulis. J. Organ. Chern. (U. S.A.) 37, 2532 (1972). 408. HERZ, W., S. V. BHAT, and V. SUOARSANAM: Sesquiterpene Lactones and Flavones of Ivafrutescens. Phytochem. 11, 1829 (1972). 408 a. HERZ, W., and J. F. BwuNT: Structure of Tirotundin. J. Organ. Chern. (U. S. A.) 43, 1268 (1978). 408b. -- Stereochemistry of.Woodhousin. J. Organ. Chern. (U.S.A.) 43, 4887 (1978). 409. HERZ, W., H. CHIKAMATSU, N. VISWANTHAN, and V. SUOARSANAM: Structure of Ivalbin, a Modified Guaiano!ide from Iva dealbata Gray. J. Organ. Chern. (U. S. A) 32, 682 (1967). 409a. HERZ, W., and R. DE GROOTE: Desacetyleupaserrin and Nevadensin From Helianthus pumilus. Phytochem. 16, 1307 (1977). 410. HERZ, W., C. M. GAST,. and P. S. SUBRAMANIAM: Sesquiterpene Lactones of Helenium alternifolium (Spreng.) Cabrera. Structures of Brevilin A, Linifolin A, and Alternilin. J. Organ. Chern. (U. S. A) 33,2780 (1968). 342 N. H. FISCHER, E. J. OLIVIER, and H. D. FISCHER:

411. HERZ, W., and G. HOGENAUER: Ivalin, a New Sesquiterpene Lactone. J. Organ. Chern. (U. S. A.) 27, 905 (1962). 412. -- Isolation and Structure of Coronopilin, A New Sesquiterpene Lactone. 1. Organ. Chern. (U. S. A) 26, 5011 (1961). 413. HERZ, W., G. HOGENAUER, and A ROMO DE VIVAR: Constituents of Iva Species. III. Structure of Microcephalin, A New Sesquiterpene Lactone. J. Organ. Chern. (U. S. A.) 29, 1700 (1964). 414. HERZ, W., and S. INAYAMA: Constituents of Gaillardia Species. II. Structures of Pulchellin Band Pulchellin C. Tetrahedron 20, 341 (1964). 414a. HERZ, W., and H. B. KAGAN: Determination of the Absolute Configuration of Hydroxylated Sesquiterpene Lactones by Horeau's Method of Asymmetric Esterifica• tion. J. Organ. Chern. (U. S.A) 32, 216 (1967). 414b. HERZ, W., P. JAYARAMAN, and H. WATANABE: Constituents of Helenium Species. IX. The Sesquiterpene Lactones of H. fiexuosum Raf. and H. campestre Small. J. Arner. Chern. Soc. 82, 2276 (1960). 415. HERZ, W., and P. S. KALYANARAMAN: Mikanokryptin in Melampodium divaricatum. Phytochern. 14, 1664 (1975). 416. -- Acanthospermal A and Acanthospermal B, Two New Melarnpolides from Acanthospermum Species. J. Organ. Chern. (U. S. A.) 40, 3486 (1975). 417. HERZ, W., P. S. KALYANARAMAN, G. RAMAKRISHNAN, and J. F. BLOUNT: Sesqui• terpene Lactones of Eupatorium perfoliatum. 1. Organ. Chern. (u. S. A.) 42, 2264 (1977). 418. HERZ, W., Y. KISIDDA, and M. V. LAKSHMIKANTHAM: Constituents of Helenium Species. XVI. Structures of Flexuosin A and Flexuosin B. Tetrahedron 20, 979 (1964). 419. HERZ, W., and M. V. LAKSHMIKANTHAM: Constituents of Helenium Species. XVII. Sesquiterpene Lactones of Helenium thurberi Gray and the Stereochemistry of Bigelovin. Tetrahedron 21, 1711 (1965). 420. HERZ, W., M. V. LAKSHMIKANTHAM, and R. N. MIRRINGTON: Constituents of Helenium Species. XVIII. l-Epiisotenulin and Its Transformations. Tetrahedron 22, 1709 (1966). 420a. HERZ, W., and R. B. MITRA: Correlation of Helenalin and Alloisotenulin. J. Arner. Chern. Soc. 80,4876 (1958). 421. HERZ, W., R. B. MITRA, K. RABINDRAN, and W. A ROHDE: Constituents of Helenium Species. VII. Bitter Principles of H. pinnatifidum (Nutt.) Rydb., H. verna Ie Walt., H. brevi/olium (Nutt.) A Wood, and H. fiexuosum Raf. J. Arner. Chern. Soc. 81, 1481 (1959). 422. HERZ, W., R. B. MITRA, K. RABINDRAN, and N. VISWANATHAN: Constituents of H elenium Species. XI. The Structure of Pinnatifidin. J. Organ. Chern. (U. S. A) 27, 4041 (1962). 423. HERZ, W., M. MIYAZAKI, and Y. KISHIDA: Structures of Parthenin and Ambrosin. Tetrahedron Letters 1961, 82. 424. HERZ, W., J. POPLAWSKI, and R. P. SHARMA: New Guaianolides from Liatris Species. J. Organ. Chern. (U. S.A) 40,199 (1975). 425. HERZ, W., S. RAJAPPA, M. V. LAKSHMIKANTHAM, D. RAULAIS, and J. J. SCHMID: Constituents of Gaillardia Species. V. Isolation and Structure of Spathulin. J. Organ. Chern. (U. S. A.) 32, 1042 (1967). 426. HERZ, W., S. RAJAPPA, M. V. LAKSHMIKANTHAM, and J. J. SCHMID: Constituents of Gaillardia Species. III. The Structure of Gaillardilin, a New Pseudoguaianolide. Tetrahedron 22,693 (1966). 427. HERZ, W., S. RAJAPPA, S. K. RoY, J. J. SCHMID, and R. N. MIRRINGTON: Constituents of Gaillardia Species. IV. The Sesquiterpene Lactones of Gaillardiafastigiata Greene. Tetrahedron 22,1907 (1966). The Biogenesis and Chemistry of Sesquiterpene Lactones 343

428. HERz, W., D. RAuLAIs, and G. D. ANDERSON: Sesquiterpene Lactones of Ambrosia cordifolia. Phytochern. 12, 1415 (1973). 429. HERZ, W., W. A. ROHDE, K. RABINDRAN, P. JAYARAMAN, and N. VISWANATHAN: R~vised Structure of Tenulin. J. Amer. Chern. Soc. 84, 3857 (1962). 430. HERz, W., A. ROMO DE VIVAR, and M. V. LAKSHMIKANTHAM: Structure of Pseudo• ivalin, a New Guaianolide. J. Organ. Chern. (U. S. A.) 30, 118 (1965). 431. HERz, W., A. ROMO DE VIVAR, J. ROMO, and N. VISWANATHAN: Constituents of Helenium Species. xv. The Structure of Mexicanin C, Relative Stereochemistry of its Congeners. Tetrahedron 19, 1359 (1963). 432. ---- Constituents of Helenium Species. XIII. The Structure of Helenalin and Mexicanin A. J. Amer. Chern. Soc. 85, 19 (1963). 433. HERZ, W., and S. K. Roy: New Pseudoguaianolides from Gaillardia pulchella. Phytochem. 8, 661 (1969). 434. HERZ, W., and P. S. SANTHANAM: Virginolide, a New Guaianolide from Helenium virginicum Blake. J. Organ. Chern. (U. S. A.) 32, 507 (1967). 435. -- Arbiglovin. A New Guaianolide from Artemisia bigelovii Gray. J. Organ. Chern. (U.S.A.) 30, 4340 (1965). 436. HERZ, W., and R. P. SHARMA: A trans-l,2-cis-4,5-Germacradienolide and Other New Germacranolides from Tithonia Species. J. Organ. Chern. (U.S.A.) 40, 3118 (1975). 437. -- Complete Stereochemistry of Tenulin. Carbon-13 Nuclear Magnetic Reson• ance Spectra of Tenulin Derivatives. J. Organ. Chern. (U. S. A.) 40, 2557 (1975). 438. -- Pycnolide, a seco-Germacradienolide from Liatris pycnostachya, and other Antitumor Constituents of Liatris Species. J. Organ. Chern. (U. S. A.) 41, 1248 (1976). 439. -- New Germacranolides from Liatris Species. Phytochem. 14, 1561 (1975). 440. -- Seco-germacradienolide from Liatris pycnostachya. J. Organ. Chern. (U. S.A.) 40,392 (1975). 441. -- Sesquiterpene Lactones of Eupatorium hyssopifolium. A Germacranolide with an Unusual Lipid Ester Side Chain. J. Organ. Chern. (U. S. A.) 41, 1015 (1976). 442. HERZ, W., and A. SRINIVASAN: Reexamination of Gaillardia amblyodon. Isolation of New Pseudoguaianolides. Phytochem. 13, 1187 (1974). 443. -- Pseudoguaianolides of Gaillardia amblyodon. Phytochem. 11,2093 (1972). 444. -- Stereochemistry of Spathulin. Phytochem. 13, 1171 (1974). 445. HERZ, W., A. SRINIVASAN, and P. S. KALYANARAMAN: Mikanokryptin, a New Guaianolide from Mikania. Phytochern. 14,233 (1975). 446. HERZ, W., and P. S. SUBRAMANIAM: Pseudoguaianolides in Helenium autumnale from Pennsylvania. Phytochem. 11, 1101 (1972). 447. HERZ, W., P. S. SUBRAMANIAM, and N. DENNIS: Solvent Shift Studies on Pseudo• guaianolides of the Helena1in Series. J. Organ. Chern. (U. S. A.) 34, 3691 (1969). 448. --- Stereochemistry of Flexuosin A and Related Compounds. J. Organ. Chern. (U.S.A.) 34, 2915 (1969). 449. HERZ, W., P. S. SUBRAMANIAM, and T. A. GEISSMAN: 3-Epiisotelekin from Gaillardia aristata Pursh. and the Structure of Farinosin. J. Organ. Chern. (U.S.A.) 33,3743 (1968). 450. HERZ, W., P. S. SUBRAMANIAM, R. MURARI, N. DENNIS, andJ. F. BLOUNT: Microdilin, a Complex Elemenolide from Mikania cordifolia. J. Organ. Chern. (U.S.A.) 42, 1720 (1977). 451. HERZ, W., P. S. SUBRAMANIAM, P. S. SANTHANAM, K. AOTA, and A. L. HALL: Structure Elucidation of Sesquiterpene Dilactones from Mikania scandens (L.) Willd. J. Organ. Chern. (U.S.A.) 35,1453 (1970); Errata: J. Organ. Chern. (U.S.A.) 38, 4217 (1973). 452. HERZ, W., V. SUDARSANAM, and J. J. SCHMID: New Guaianolides from Iva axillaris Pursh. ssp. robustior. J. Organ. Chern. (U. S. A.) 31, 3232 (1966). 344 N. H. FISCHER, E. J. OLIVIER, and H. D. FISCHER:

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628. KUPCHAN, S. M., R. J. HEMINGWAY, D. WERNER, and A. KARIM: Vernolepin, a Novel Sesquiterpene Dilactone Tumor Inhibitor from Vernonia hymenolepis A. Rich. J. Organ. Chern. (U. S. A.) 34, 3903 (1969). 629. KUPCHAN, S. M., R. J. HEMINGWAY, D. WERNER, A. KARIM, A. T. MCPHAIL, and G. A. SIM: Vernolepin, a Novel Elemanolide Dilactone Tumor Inhibitor from Vernonia hymenolepis. J. Amer. Chern. Soc. 90, 3596 (1968). 630. KUPCHAN, S. M., J. E. KELSEY, M. MARUYAMA, J. M. CASSADY, J. C. HEMINGWAY, and J. R. KNOX: Tumor Inhibitors XLI. Structural Elucidation of Tumor-Inhibitory Sesquiterpene Lactones from Eupatorium rotundifolium. J. Organ. Chern. (U.S.A.) 34, 3876 (1969). 630a. KUPCHAN, S. M., J. E. KELSEY, and G. A. SIM: The Stereochemistry of Germa• cranolide Sesquiterpenes. Tetrahedron Letters 1967, 2863. 631. KUPCHAN, S. M., and M. MAYURAMA: Reductive Elimination of Epoxides to Olelins with -Copper Couple. J. Organ. Chern. (U. S. A.) 36, 1187 (1971). 632. KUPCHAN, S. M., M. MARUYAMA, R. J. HEMINGWAY, J. C. HEMINGWAY, S. SHIBUYA, and T. FUJITA: Structural Elucidation of Novel Tumor-Inhibitory Sesquiterpene Lactones from Eupatorium cuneifolium. J. Organ. Chern. (U. S. A.) 38, 2189 (1973). 633. KUPCHAN, S. M., M. MARUYAMA, R. J. HEMINGWAY, J. C. HEMINGWAY, S. SHIBUYA, T. FUJITA, P. D. CRADWICK, A. D. HARDY, and G. A. SIM: Eupacunin, a Novel Anti• leukemic Sesquiterpene Lactone from Eupatorium cuneifolium. J. Amer. Chern. Soc. 93, 4914 (1971). 634. KUROKAWA, T., K. NAKANISHI, W. Wu, H. Y. Hsu, M. MARUYAMA, and S. M. KUPCHAN: Deoxyelephantopin and its Interrelation with Elephantopin. Tetrahedron Letters 1970, 2863. 635. LANE, J. F., W. T. KOCH, N. S. LEEDS, andG. GORIN: On the Toxin ofilliciumanisatum. I. The Isolation and Characterization of a Convulsant Principle: . J. Amer. Chern. Soc. 74,3211 (1952). 636. LEE, K. H., D. C. ANUFORO, E. S. HUANG, and C. PIANTADOSI: Angustibalin, a New Cytotoxic Sesquiterpene Lactone from Balduina angustifolia. J. Pharm. Sci. 61, 626 (1972); Chern. Abstr. 77, 28809j (1972). 637. LEE, K. H., C. M. COWHERD, and M. T. WOLO: Deoxyelephantopin, an Antitumor Principle from Elephantopus carolinianus. J. Pharm. Sci. 64, 1572 (1975); Chern. Abstr. 83, 1608IOf(1975). 638. LEE, K. H., H. FURUKAWA, and E. S. HUANG: Synthesis and Cytotoxic Activity of Helenalin amine. Adducts and Related Derivatives. J. Med. Chern. 15, 609 (1972); Chern. Abstr. 77, 56404s (1972). 639. LEE, K. H., H. FURUKAWA, S. H. KIM, and C. PIANTADOSI: Reaction of Helenalin with Hydrogen Chloride. J. Pharm. Sci. 62, 987 (1973); Chern. Abstr. 79, 53610m (1973). 640. LEE, K. H., H. FURUKAWA, M. KOZUKA, H. C. HUANG, P. A. LUHAN, and A. T. MCPHAIL: Molephantin, a Novel Cytotoxic Germacranolide from Elephantopus mollis. X-Ray Crystal Structure. Chern. Commun. 1973,476. 641. LEE, K. H., and T. A. GEISSMAN: Sesquiterpene Lactones of Artemisia Species. Arte• fransin from A.franserioides. Phytochem. 10,205 (1971). 642. -- Sesquiterpene Lactones of Artemisia. Constituents of A. ludoviciana ssp. mexicana. Phytochem. 9, 403 (1970). 643. LEE, K. H., M. HARUNA, H. C. HUANG, B. S. Wu, and I. H. HALL: Helenalin, an Anti• tumor Principle from Anaphalis morrisonicola Hay. J. Pharm. Sci. 66, 1194 (1977); Chern. Abstr. 87, 145893s (1977). 644. LEE, K. H., H. C. HUANG, E. S. HUANG, and H. FURUKAWA: Eupatolide, a New Cytotoxic Principle from Eupatorium formosanum. J. Pharm. Sci. 61, 629 (1972); Chern. Abstr. 77, 28810c (1972).

Fortschritte d. Chern. ~rg. Naturst. 38 23 354 N. H. FISCHER, E. J. OLIVIER, and H. D. FISCHER:

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23* 356 N. H. FISCHER, E. J. OLIVIER, and H. D. FISCHER:

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Parthenium (Compositae). Systematic and Ecological Implications. Diss. Abstr. Int. B 1976, 37,49; Chern. Abstr. 85, 90l94y (1976). 861. - Ecogeographic Distribution of Secondary Constituents in Parthenium (Composi• tae). Biochem. System. Ecol. 5, 207 (1977). 862. RODRIGUEZ, E., M. O. DILLON, T. J. MABRY, J. C. MITCHELL, and G. H. N. TOWERS: Dermatologically Active Sesquiterpene Lactones in Trichomes of Parthenium hyste• rophorus L. (Compositae). Experientia 32, 236 (1976); Chern. Abstr. 84, 131199d (1976). 863. RODRIGUEZ, E., W. EpSTEIN, and J. C. MITCHELL: The Role of Sesquiterpene Lactones in Contact Sensitivity of Some North and South American Species of Feverfew (Parthenium - Compositae). J. Contact Dermatitis 3,155 (1977). 864. RODRIGUEZ, E., G. H. N. TOWERS, and J. C. MITCHELL: Biological Activities of Sesquiterpene Lactones. Phytochem. 15, 1573 (1976). 865. RODRIGUEZ, E., H. YOSHIOKA, and T. J. MABRY: Sesquiterpene Lactone Chemistry of Partheniumfruticosum and P. schottii. Rev. Latinoamer. Quim. 2, 184 (1972); Chern. Abstr. 76, 153956 k (1972). 866. --- The Sesquiterpene Lactone Chemistry of the Genus Parthenium (Compo• sitae). Phytochem. 10, 1145 (1971). 867. RODRIGUEZ-HAHN, L., M. JIMENEZ, E. DIAZ, C. GUERRERO, A. ORTEGA, and A. ROMO DE VIVAR: The Revised Structure of Mortonin. Tetrahedron 33, 657 (1977). 868. ROGERS, D., G. P. Moss, and S. NEIDLE: Proposed Conventions for Describing Germacranolide Sesquiterpenes. Chern. Commun. 1972, 142. 869. ROGERS, D., and M. UL-HAGUE: The Structure of Bromoisotenulin. Proc. Chern. Soc. (London) 1963, 92. 870. ROJAS GARCIDUENAS, M., X. A. DOMINGUEZ, J. FERNANDEZ, and G. ALANIS: New Growth Inhibitors from Parthenium hysterophorus. Rev. Latinoamer. Quim. 3, 52 (1972). 871. ROMANUK, M., V. HEROUT, and F. SORM: The Constitution of Dehydrocostus• lactone. Collect. Czech. Chern. Comm. 21, 894 (1956). 872. ROMO, J.: Recent Studies on Sesquiterpenes. Pure Appl. Chern. 21, 123 (1970). 873. ROMO, J., P. JOSEPH-NATHAN, and F. DIAZ: The Constituents of Helenium aromaticum (Hook) Bailey. The Structures of Aromatin and Aromaticin. Tetrahedron 20, 79 (1964). 874. ROMO, J., P. JOSEPH-NATHAN, A. ROMO DE VIVAR, and C. ALVAREZ: The Structure of Peruvinin, a Pseudoguaianolide Isolated from Ambrosia peruviana Willd. Tetra• hedron 23,529 (1967). 875. ROMO, J., P. JOSEPH-NATHAN, and G. SlADE: The Structure of Cuman in, a Constituent of Ambrosia cumanensis. Tetrahedron 22, 1499 (1966). 876. ROMO, J., and C. LOPEZ VANEGAS: Stereochemistry Determinations of the Substi• tuents in Position 1 of Some Guaianolides. Bol. Inst. Quim. Univ. Nac. Auton. Mex. 21,82 (1969); Chern. Abstr. 73, 35540k (1970). 877. ROMO, J., T. RIOS, and L. QUIJANO: Ligustrin, A Guaianolide Isolated from Eupatorium ligustrinum DC. Tetrahedron 24,6087 (1968). 878. ROMO, J., and L. RODRIGUEZ-HAHN: Canambrin, A New Sesquiterpene Dilactone from Ambrosia canescens. Phytochem. 9, 1611 (1970). 879. ROMO, J., and A. ROMO DE VIVAR: The Pseudoguaianolides. In: Fortschr. Chern. Organ. Naturstoffe (ZECHMEISTER, L., ed.), Vol. 25, p. 90. Wien: Springer. 1967. 880. ROMO, J., A. ROMO DE VIVAR, and M. AGUILAR: Natural Products from Compo sitae Species. Neohelenalin. Bol. Inst. Quim. Univ. Nac. Auton. Mex. 21, 66 (1969); Chern. Abstr. 73, 25685x (1970). 881. ROMO, J., A. ROMO DE VIVAR, and E. DIAZ: The Guaianolides of Ambrosia cumanensis HBK. The Structures of Cumambrins A and B. Tetrahedron 24, 5625 (1968). 366 N. H. FISCHER, E. J. OLIVIER, and H. D. FISCHER:

882. ROMO, J., A ROMO DE VIVAR, E. DIAZ, A. VELEZ, E. LEON, and E. URBINA: Distri• bution of Sesquiterpene Lactones in Several Ambrosia Species. In: Recent Advan. Phytochem. (STEELINK, C., and Y. C. RUNECKLES, eds.), Vol. 3, p. 249. New York: Appleton Century Croft. 1970. 883. ROMO, J., A ROMO DE VIVAR, and P. JOSEPH-NATHAN: The Structure of Mexicanin H. Tetrahedron Letters 1966,1029. 884. --- The Constituents of Zaluzania augusta. The Structures of Zaluzanins A and B. Tetrahedron 23, 29 (1967). 885. ROMO, J., A ROMO DE VrvAR, and W. HERZ: Constituents of Helenium Species. XIV. The Structure of Mexicanin E. Tetrahedron 19, 2317 (1963). 886. ROMO, J., A ROMO DE VIVAR, A ORTEGA, E. DIAZ, and M. A CARINO: Las Estruc• turas De La Zinarosina y De La Dihidrozinarosina Componentes De La Zinnia acerosa DC. (Gray). Rev. Latinoamer. Quim. 2, 24 (1971). 887. ROMO, J., and H. TELLO: Estudia De La Artemisia mexicana Armexina, Un Nuevo Santanolido Cuya Lactona Posee Fusion Cis. Rev. Latinoamer. Quim. 3, 122 (1972); Chern. Abstr. 78, 121339m (1973). 888. ROMO, J., A ROMO DE VrvAR, R. TREVINO, P. JOSEPH-NATHAN, and E. DIAz: Constituents of Artemisia and Chrysanthemum Species. The Structure of Chrysarte• mins A and B. Phytochem. 9, 1615 (1970). 889. ROMO, J., A ROMO DE VrvAR, A VELEZ, and E. URBINA: Franserin and Confertin; New Pseudoguaianolides Isolated from Franseria and Ambrosia Species. Canad. J. Chern. 146, 1535 (1968). 890. ROMO DE VIVAR, A: Organic Structure Determination by the Double and Triple Irradiation Technique. Rev. Soc. Quim. Mex. 14, 54 (1970); Chern. Abstr. 74, 42501 x (1971); Chern. Abstr. 73, 88037h (1970). 891. - Sesquiterpene Lactones in Compo sitae. Biogenesis and Taxonomic Implications. Rev. Latinoamer. Quim. 8, 63 (1977); Chern. Abstr. 87, 18934p (1977). 892. ROMO DE VIVAR, A, M. AGUILAR" H. YOSHIOKA, E. RODRIGUEZ, A. HIGO, J. A. MEARS, and T. J. MABRY: New Pseudoguaianolides from Parthenium confertum Gray (Compositae). Tetrahedron 26,2775 (1970). 893. ROMO DE VIVAR, A., E. A BRATOEFF, and T. RIOs: Structure of Hysterin, a New Sesquiterpene Lactone. J. Organ. Chern. (U. S. A) 31,673 (1966). 894. ROMO DE VIVAR, A., A. CABRERA, A ORTEGA, and J. ROMO: Constituents of Zaluzania Species - II. Structures of Zaluzanin C and Zaluzanin D. Tetrahedron 23,3903 (1967). 895. ROMO DE VIVAR, A., and G. GoNZALEZ: Aislamiento De La Lactona Dihidrocostus. Preparacion De Espiroepoxidos De Lactones Sesquiterpenicas. Rev. Latinoamer. Quim. 2, 142 (1971); Chern. Abstr. 76, 46326h (1972). 896. ROMO DE VIVAR, A, C. GUERRERO, and G. WITTGREEN: Los terpenoides de Parthenium incanum H. B. K. Rev. Latinoamer. Quim. 1, 39 (1970); Chern. Abstr. 74, 88165u (1971). 897. ROMO DE VIVAR, A, C. GUERRERO, E. DIAZ, and A. ORTEGA: Structure and Stereo• chemistry of Zexbrevin A3 (2 H) Furanone Germacranolide. Tetrahedron 26, 1657 (1970). 898. ROMO DE VIVAR, A, C. GUERRERO, E. DIAZ, E. A BRATOEFF, and L. JIMENEZ: The Germacranolides of Viguiera buddleiaeformis. Structures of Budlein-A and -B. Phytochem. 15, 525 (1976). 899. ROMO DE VIVAR, A., J. GUEVARA, C. GUERRERO, and A ORTEGA: Los Terpenoids De Mortonia gregii Gray. Estructura De La Mortonina A Rev. Latinoamer. Quim. 3, I (1972); Chern. Abstr. 77, 140326a (1972). 900. ROMO DE VIVAR, A., and H. JIMENEZ: Structure of Santamarine, a New Sesquiterpene Lactone. Tetrahedron 21,1741 (1965). The Biogenesis and Chemistry of Sesquiterpene Lactones 367

900a. ROMO DE VIVAR, A., and F. OLMOS: Chemical Study of Achillea millefolium. Rev. Soc. Quim. Mex. 12, 212A (1968); Chern. Abstr. 71, 3493q (1969). 901. ROMO DE VIVAR, A., and A. ORTEGA: Structures of Bahia-I and Bahia-II: Two New Guaianolides. Canad. J. Chern. 47, 2849 (1969). 902. ROMO DE VIVAR, A., A. L. PEREZ, H. FLORES, L. RODRIGUEZ-HAHN, and M. JIMENEZ: Confertdiolide, A Novel Sesquiterpenoid Lactone from Parthenium. Phytochemistry 17,279 (1978). 903. ROMO DE VIVAR, A., L. RODRIGUEZ-HAHN, J. ROMO, M. V. LAKSHMIKANTHAM, R. N. MIRRINGTON, J. KAGAN, and W. HERZ: Constituents of Helenium Species ~ XIX. Further Transformations of Helenalin and its Congeners. The l-Epihelenalin and 1- Epiambrosin Series. Tetrahedron 22,3279 (1966). 904. ROMO DE VIVAR, A., and J. ROMO: Constituents of Helenium mexicanum H. B. K. Chern. and Ind. 1959, 882. 905. ROMO DE VIVAR, A., F. VAZQUEZ, and C. ZETINA: Sesquiterpene Lactones of Arte• misia m('xicana var. angustifolia. Rev. Latinoamer. Quim. 8, 127 (1977). 906. Ross, J. 'M., D. S. TARBELL, W. E. LOVETT, and A. D. CROSS: The Chemistry of Fumagillin. IV. The Presence of an Epoxide Grouping and Other Observations on the Nature of the Oxygen Functions. J. Amer. Chern. Soc. 78, 4675 (1956). 907. ROSSMAN, M. G., and W. N. LIPSCOMB: Molecular Structure and Stereochemistry of an Iresin Diester. J. Amer. Chern. Soc. 80, 2592 (1958). 907a. RUBAN, G., V. ZABEL, K. H. GENSCH, and H. SMALLA: The Crystal Structure and Absolute Configuration of Lactucin. Acta Crystall B 34, 1163 (1978). 908. RUSTAIYAN, A., and L. NAZARIANS: Isolation of the Sesquiterpene Lactone Deacetoxymatricarin from Achillea eriophora DC. Fitoterapia 48, 175 (1977). 909. RUCKER, G.: Sesquiterpene. Angew. Chern. 85, 895 (1973). 910. RUESCH, H., and T. J. MABRY: The Isolation and Structure of Tetraneurin-A, a New Pseudoguaianolide from Parthenium alpinum var. tetraneuris (Compositae). Tetra• hedron 25,805 (1969). 911. RUZICKA, L.: a. The Isoprene Rule and the Biogenesis of Terpenic Compounds. Experientia 9,357 (1953). 912. ~ Faraday Lecture ~ History of the Isoprene Rule. Proc. Chern. Soc. (London) 1959, 341. 913. RUZICKA, L., P. PIETH, T. REICHSTEIN, and L. EHINANN: Zur Kenntnis der Alanto• lactone. Synthese des 1,4-Dimethyl-6-isopropyl und des 1,5-Dimethyl-7-isopropyl• naphthalins. Helv. Chim. Acta 16, 268 (1933). 914. RYBALKO, K. S.: Isolation of Mibulactone from Artemisia taurica. Khim. Prir. Soedin. 1965,142; Chern. Abstr. 63, 6786f (1965). 914a. RYBALKO, K. S., A. N. BANKOVSKAYA, and R. 1. EVSTRATOVA: Sesquiterpene Lactone from Artemisia austriaca. Med. Prom. SSSR. 16, 13 (1962); Chern. Abstr. 58, 2474 (1963). 915. RYBALKO, K. S., A. 1. BAN'KOVSKII, and P. N. KIBALCIC: Grosshemine, a New Sesquiterpene Lactone from Grossheimia macrocephala. Zhurn. Obshchei Khimii 34,1358 (1964); Chern. Abstr. 61, 1896h (1964). 916. RYBALKO, K. S., A. 1. BAN'KOVSKII, and V. 1. SHEICHENKO: Natural Sesquiterpenoid Lactones. Medicinal Plants (Russia) 15, 168 (1969); Chern. Abstr. 75, 20632j (1971). 917. RYBALKO, K. S., and L. DOLEJS: Structure of Tauremisin, A Sesquiterpenic Lactone of Santonine Type from Artemisia taurica Willd. Collect. Czech. Chern. Comm. 26, 2909 (1961). 918. RYBALKO, K. S., O. A. KONOVALOVA, N. D. ORISHCHENKO, and A. 1. SHRETER: Lactones of Some Species of the Genus Saussurea DC. Rastit. Resur. 12, 387 (1976); Chern. Abstr. 85, 174252d (1976). 368 N. H. FISCHER, E. J. OLIVIER, and H. D. FISCHER:

919. RYBALKO, K. S., O. A. KONOVALOVA, and E. F. PETROVA: Orientin, a New Sesqui• terpene Lactone from Siegesbeckia orientalis. Khim. Prir. Soedin. 1976, 394; Chern. Abstr.85, 124182k (1976). 920. RYBALKO, K. S., M. N. MUKHAMETZHANOV. V. 1. SHEICHENKO, and O. A. KONO• VALOVA: Sesquiterpene Lactones of Stizolophus balsamita. Khim. Prir. Soedin. 12, 467 (1976); Chern. Abstr. 86, 5643x (1977). 921. RYBALKO, K. S., V. 1. SHEICHENKO, G. A. MASLOVA, E. Y. KISELEVA, and 1. A. GUBANOV: Britanin, a Lactone from Inula britannica. Khim. Prir. Soedin. 4, 251 (1968); Chern. Abstr. 70, 47618t (1969). 922. RYBALKO, K. S., E. A. TRUTNEVA, and P. N. KIBAL'CHICH: A Crystalline Substance Isolated from Arnica foliosa. Aptechn. Del0 14, 32 (1965); Chern. Abstr. 63, 18541 a (1965). 922a. SABER, A. H., H. ABU SHADY, and M. S. EL-ANTABLY: Judaicin. Bull. Fac. Pharm. Cairo Univ. 3,119 (1964); Chern. Abstr. 64, 12729d (1966). 923. SAITBAEVA, I. M., and G. P. SIDYAKIN: Artemisin from Artemisia cina. Khim. Prir. Soedin. 7,120 (1971); Eng!. edit.: p. 113. 924. SAITOH, T., T. A. GEISSMAN, T. G. WADDELL, W. HERZ, and S. V. BHAT: Sesqui• terpene Lactones of Eriophyllum confertiflorum (DC.) Gray. Rev. Latinoamer. Quim. 2,69 (1971); Chern. Abstr. 75, 129952q (1971). 925. SAKABE, N., Y. HIRATA, A. FURUSAKI, Y. TOMIIE, and I. NITTA: X-Ray Structure Determination of Bromonoranisatinone, A Derivative of Anisatin. Tetrahedron Letters 1965, 4795. 926. SALEH, A. A., G. A. CORDELL, and N. R. FARNSWORTH: Acanthamolide, a Melampo• !ide Amide from Acanthospermum glabratum (Compositae). Chern. Commun. 1977,376. 927. SALMON, M., E. DIAZ, and A. ORTEGA: Christinine, a New Epoxyguaianolide from Stevia serrata Cav. J. Organ. Chern. (U. S. A.) 38, 1759 (1973). 927 a' --- Epoxylactonas de Stevia serrata Cav. Rev. Latinoamer. Quim. 8, 172 (1977). 928. SALMON, M., A. ORTEGA, and E. DIAZ: Structure and Stereochemistry of a New Germacrane Sesquiterpene Lactone. Rev. Latinoamer. Quim. 6, 45 (1975); Chern. Abstr. 83, 193528y (1975). 929. SAMEK, Z.: The Determination of the Stereochemistry of Five-membered IX,~-Un­ saturated Lactones with an Exomethylene Double Bond, Based on the Allylic Long• Range Couplings of Exomethylene Protons. Tetrahedron Letters 1970, 671. 929a. - On the Validity of the "cis/trans" Lactone Rule for Allylic Coupling Constants of the IX-Exomethylene Protons in Natural Sesquiterpenic IX-Exomethylene y-Lacto• nes. Collect. Czech. Chern. Comm. 43,3210 (1978). 930. SAMEK, Z., M. HOLUB, E. BLOSZYK, B. DROZDZ, and V. HEROUT: Relative and Absolute Configuration of the Sesquiterpenic Lactone Erivanin. Collect. Czech. Chern. Commun. 40, 2676 (1975). 931. SAMEK, Z., M. HOLUB, B. DROZDZ, and H. GRABARCZYK: Arctolide - A New Sesquiterpenic Lactone from Arctotis grandis Thunb. Collect. Czech. Chern. Comm. 42, 2217 (1977). 932. SAMEK. Z., M. HOLUB, B. DROZDZ, H. GRABARCZYK, and B. HLADON: Xerantho• !ide - A New Cytotoxically Active Sesquiterpene Lactone from Xeranthenum cylindraceum. Collect. Czech. Chern. Comm. 42, 2441 (1977). 933. SAMEK, Z., M. HOLUB, B. DROZDZ, G. JOMMI, A. CORBELLA, and P. GARIBOLDI: Sesquiterpenic Lactones of the Cynara scolymus L. Species. Tetrahedron Letters 1971, 4775. 934. SAMEK, Z., M. HOLUB, H. GRABARCZYK, B. DROZDZ, and V. HEROUT: Structure of Sesquiterpenic Lactones from Tanacetum vulgare L. Collect. Czech. Chern. Comm. 38, 1971 (1973). The Biogenesis and Chemistry of Sesquiterpene Lactones 369

935. ----- The Structure of Hydroxyisonobilin - A Cytostatically Active Sesquiterpene Lactone from the Leaves of Anthemis mobilis L. Collect. Czech. Chern. Comm. 42, lO65 (1977). 936. SAMEK, Z., M. HOLUB, V. Herout, and F. SORM: Revision of the Structure of Cnicin. Tetrahedron Letters 1969, 293l. 937. SAMEK, Z., M. HOLUB, V. J. NOVIKOV, J. N. FOROSTJAN, and D. P. POPA: The Structure of Ivoxanthin, a Sesquiterpenic Lactone from Cyclachaena xanthifolia Fresen. Collect. Czech. Chern. Comm. 35, 3818 (1970). 938. SAMEK, Z., M. HOLUB, K. VOKAC, B. DROZDZ, G. JOMMI, P. GARIBOLDI, and A. COR• BELLA: The Structure of Grosheimin. Collect. Czech. Chern. Comm. 37, 2611 (1972). 939. SANCHES PARAREDA, I., J. SANCHES PARAREDA, and J. M. VIGUERA: Stenophyllolide, a New Sesquiterpene Lactone. An. Chim. 64, 633 (1968); Chern. Abstr. 70, 37933c (1969). 940. SANCHEZ-VIESCA, F., and J. ROMO: Estafiatin, a New Sesquiterpene Lactone Isolated from Artemisia mexicana (Willd). Tetrahedron 19, 1285 (1963). 941. SASAKI, T., and S. EGUCHI: Reactions of Isoprenoids. Revised Structure of Pyro• lumisantonin. Bull. Chern. Soc. Japan 42, 2736 (1969); Chern. Abstr. 72, 32044v (1970). 942. SATHE, R. N., N. R. DESHPANDE, G. H. KULKARNI, G. R. KELKAR, and K. G. DAS: Correlation of Structure and Fragmentation Modes of Costunolide and Its Deri• vatives. Org. Mass Spectrom. 5, 197 (1971); Chern. Abstr. 74, 142092h (1971). 943. SATHE, R. N., G. H. KULKARNI, and G. R. KELKAR: Catalytic Hydrogenation Products of Dihydrocostunolide. Indian J. Chern. 9, lOl (1971); Chern. Abstr. 74, 112234p (1971). 944. SATHE, R. N., G. H. KULKARNI, G. R. KELKAR, and K. G. DAS: Fragmentation of Costunolide and Its Derivatives Under Electron-Impact. Org. Mass Spectrom. 2, 935 (1969); Chern. Abstr. 72, 32045w (1970). 945. SATODA, I., N. YOSHIDA, and E. YosHn: Isolation of Lumisantonin from Artemisia kurramensis. Yakugaku Zasshi 79,267 (1959); Chern. Abstr. 53, 11532h (1959). 945 a. SCHAFFNER, K.: Photochemische Umwandlungen ausgewahlter Naturstoffe. In: Fortschritte der Chemie organischer Naturstoffe (ZECHMEISTER, L., ed.), Vol. 22, p. l. Wien: Springer. 1967. 946. SCHENCK, G., H. GRAF, and W. SCHREBER: Bitter Substances from the Latex of Lactuca virosa. Isolation of Lactucin and Lactucopicrin. Arch. Pharm. Deutsch. 277,137 (1939); Chern. Abstr. 33, 7041-8. 947. SCHMALLE, H. W., K. H. KLASKA, and O. JARCHOW: Die Kristall- und Molekiil• struktur von Arteglasin A, 8ot-Acetoxy-3,4-epoxy-4~-guaia-l(10), 11 (13)-dieno-6ot, 12- lacton. Acta Crystallogr. B33, 2213 (1977). 948. SCHNEIDER, G., and K. THIELE: Properties and Determination of the Bitter Principle Cynaropicrin in Cynara. Planta Med. 25, 149 (1974); Chern. Abstr. 81, 35534b (1974). 949. -- Distribution of the Bitter Principle Cynaropicrin in Cynara. Planta Med. 26, 174 (1974); Chern. Abstr. 82, 54198g (1975). 950. SCHULZ, K. H., B. M. HAUSEN, L. WALLHOEFER, and P. SCHMIDT-LoEFFLER: Chrysanthemum Allergy. Experimental Studies on the Causative Agents. Arch. Dermatol. Forsch. 251, 235 (1975); Chern. Abstr. 82, 110222z (1975). 951. SEAMAN, F. C., and N. H. FISCHER: Longipin, a New Melampolide from Melampo• dium longipes (Heliantheae, Compositae). Phytochem. 18, lO65 (1979). 952. -- Longipilin, A New Melampolide from Melampodium longipilum (Heliantheae, Compositae). Phytochem. 17, 2131 (1978). 953. SEAMAN, F. c., G. P. JUNEAU, D. R. DIFEO, S. JUNGK, D. F. BLOOMENSTIEL, and N. H. FISCHER: Repandin A, B, C, and D, Four New Germacranolides from Tetra• gonotheca repanda (Compositae). J. Organ. Chern. (U.S.A.) 44,3400 (1979).

Fartschritte d. Chern. argo Naturst. 38 24 370 N. H. FISCHER, E. J. OLIVIER, and H. D. FISCHER:

954. SEAMAN, F. C., T. F. STUESSY, and N. H. FISCHER: The Chemistry and Biochemical Systematics of the Subtribe Melampodiinae (Heliantheae, Compositae). To be published. 955. SEGAL, R., S. SOKOLOFF, B. HARAN, D. V. ZAITSCHEK, and D. LICHTENBERG: New Sesquiterpene Lactones from Artemisia herba alba. Phytochem. 16, 1237 (1977). 956. SEKITA, T., and S. INAYAMA: The Complete Structures ofPulchellidine and Pulchellin; A Crystallographic Study of 11, 13-Dibromopulchellin. Tetrahedron Letters 1970, 135. 956a. -- The Crystal Structure and Absolute Configuration of 1l,13-Dibromopul• chellin. Acta Cryst. B27, 877 (1971). 957. SEMMLER, F. W., and J. FELDSTEIN: Zur Kenntnis der Bestandteile der atherischen Ole. COber das Vorkommen einer Saure ClsH2202 und zweier Lactone ClsH2202 und ClsH2002 im Costuswurzelii!.) Ber. dtsch. chern. Ges. 47, 2433 (1914). 958. -- Zur Kenntnis der Bestandteile atherischer Ole. (Uber Bestandteile des Costuswurzel-Oles.) Ber. dtsch. chern. Ges. 47, 2687 (1914). 959. SERKEROV, S. V.: 11,13-Dehydroopodine from Ferula oopoda roots. Khim. Prir. Soedin. 5,490 (1969); Chern. Abstr. 73, 25677w (1970). 960. - A New Sesquiterpene Hydroxylactone from Ferula oopoda. Khim. Prir. Soedin. 7,838 (1971); Eng!. edit.: p. 817; Chern. Abstr. 76, 151049t (1972). 961. - Structure of Feropodin. Khim. Prir. Soedin. 1971, 667; Chern. Abstr. 77, 5623 e (1972). 962. - Feropodin, Sesquiterpene Lactone from Ferula oopoda roots. Khim. Prir. Soedin. 5,245 (1969); Chern. Abstr. 72, 63618q (1970). 963. - Unpublished. 964. - Sesquiterpene Lactone, Semopodin, from Ferula oopoda seeds. Khim. Prir. Soedin. 5,241 (1969); Chern. Abstr. 72, 63626r (1970). 965. - The Structure of Badkhysinin. Khim. Prir. Soedin. 7, 590 (1971); Eng!. edit.: p. 570; Chern. Abstr. 77, 5622d (1972). 966. - Badkhysidin - A New Sesquiterpene Lactone from the Roots of Ferula oopoda. Khim. Prir. Soedin. 8,176 (1972); Engl. edit.: p. 181; Chem. Abstr. 77, 58787t (1972). 967. - Lactones of Ferula badghysi. Khim. Prir. Soedin. 1976, 393; Chem. Abstr. 85, 139718p (1976). 968. - The Structure of Oopodin and Dehydro-oopodin. Khim. Prir. Soedin. 8, 63 (1972); Eng!. edit.: p. 57; Chern. Abstr. 77, 48652f(1972). 969. - The Structure of Ferulin. Khim. Prir. Soedin. 6, 371 (1970). 970. - The Sesquiterpene Lactone Ferulin from the Roots of Ferula oopoda. Khim. Prir. Soedin. 6, 134 (1970); Chem. Abstr. 73, 73111 d (1970). 971. - Structure of Semopodine and Hydroxylactone. Khim. Prir. Soedin. 1976, 392; Chern. Abstr. 85, 124181j (1976). 972. - Structure of Ferulidin: A New Sesquiterpene Lactone. Khim. Prir. Soedin. 6,428 (1970). 973. SERKEROV, S. V., and R. M. ABBASOV: Sesquiterpene Lactones of Artemisia chasarica. Khim. Prir. Soedin. 11, 657 (1975); Eng!. edit.: p. 691; Chern. Abstr. 84, 71431m (1976). 974. SERKEROV, S. V., R. M. ABBASOV, and A. N. ALESKEROVA: Sesquiterpene Lactones from Artemisia hanseniana. Khim. Prir. Soedin. 12, 661 (1976); Chem. Abstr. 86, 103081 g (1977). 975. SERKEROV, S. V., and V. 1. SHEICHENKO: Structure of Isobadkhysin. The Stereo• chemistry of Badkhysin and Isobadkhysin. Khim. Prir. Soedin. 6, 425 (1970); Chern. Abstr. 74, 17843c (1971). 976. SESHADRI, V., A. K. BATTA, and S. RANGASWAMI: A New Crystalline Lactone from Bombax malabaricum. Indian J. Chern. Sect. B 14B, 616 (1976); Chem. Abstr. 86, 27674k (1977). The Biogenesis and Chemistry of Sesquiterpene Lactones 371

977. SHAFIZADEH, F., and N. R. BHADANE: Sesquiterpene Lactones of Sagebrush. New Guaianolides from Artemisia cana ssp. viscidula. J. Organ. Chem. (U. S. A.) 37, 3168 (1972). 978. -- Sesquiterpene Lactones of Artemisia arbuscula and A. tridentata. Phytochem. 12, 857 (1973). 979. -- Badgerin, a New Germacranolide from Artemisia arbuscula ssp. arbuscula. J. Organ. Chem. (U. S. A.) 37, 274 (1972). 980. SHAFIZADEH, F., N. R. BHADANE, and R. G. KELSEY: Sesquiterpene Lactones of Sagebrush. Constituents of Artemisia tripartita. Phytochem. 13,669 (1974). 981. SHAFIZADEH, F., N. R. BHADANE, M. S. MORRIES, R. G. KELSEY, and S. N. KHANNA: Sesquiterpene Lactones of Big Sagebrush. Phytochem. 10,2745 (1971). 982. SHAM'YANOV, 1. D., A. MALLABAEV, V. RAKHMANKULOV, and G. P. SIDYAKIN: Sesqui• terpene Lactones of Saussurea elegans. Khim. Prir. Soedin. 12, 819 (1976); Chem. Abstr. 86, 136305 m (1977). 983. SHEICHENKO, V. 1., and K. S. RYBALKO: NMR-Spectra, Structure and Stereo• chemistry of Grossheimin. Khim. Prir. Soedin. 8, 724 (1972); Engl. edit.: p. 708; Chem. Abstr. 78, 84562f (1973). 984. -- The Structure of Grossheimin. Khim. Prir. Soedin. 6, 687 (1970); Engl. edit.: p. 699; Chem. Abstr. 74, 112237 s (1971). 985. SHEICHENKO, V. 1., V. F. ZAKHAROV, V. P. ZVOLINSKII, R. 1. EvsTRATovA, and K. S. RYBALKO: Use of the Paramagnetic Shift Agent Eu(DPMh to Study the PMR Spectra and Stereochemistry of Arnifolin. Khim. Prir. Soedin. 9, 630 (1973); Engl. edit.: p. 595. 986. SHIRAHATA, K., T. KATO, Y. KITAHARA, and N. ABE: Constituents of Genus Petasites. Bakkenolide-A, A Sesquiterpene of Novel Carbon Skeleton. Tetrahedron 25, 3179 (1969). 987. ---- Mass Spectra of Bakkenolides and Their Derivatives. Tetrahedron 25, 4671 (1969). 987 a. SILVA, M.: Constituents of Helenium plantagineum. J. Pharm. Sci. 56, 922 (1967). 988. SIM, G. A.: X-Ray Diffraction. Natural Products and Related Compounds. Mol. Struct. Diffr. Methods 4, 134 (1976); Chem. Abstr. 86, 138854p (1977). 989. - X-Ray Diffraction. Natural Products and Small Biological Molecules. Mol. Struct. Diffr. Methods 2,131 (1974); Chem. Abstr. 82, 169551j (1975). 990. SIMS, J. J., and K. A. BERRYMAN: Virginin. A Sesquiterpene Lactone from Encelia virginensis. Phytochem. 11, 444 (1972). 991. SIMONOVIC, D. M., A. S. RAO, and S. C. BHATTACHARYYA: The Synthesis of Tetra• hydrosaussurea Lactone. Tetrahedron 19, 1061 (1963). 991 a. SIMONSEN, J., and D. H. R. BARTON: The Terpenes, Vol. III, The Sesquiterpenes, Diterpenes and their Derivatives. Cambridge: At the University Press. 1952. 991 b. SMOLENSKI, C. L. BELL, and L. BAUER: Isolation of Achillin from Achillea millefolium. Lloydia 30,144 (1967). 992. SNATZKE, G.: Stereochemistry ofSesquiterpenes and Circular Dichroism. Mezhdunar. Kongr. Efirnym. Maslam. [Mater.], 4th, 1968, 316; Chem. Abstr. 78, 124746c (1973). 992a. - Application of Circular Dichroism to the Stereochemistry of Essential Oils. Riechstoffe, Aromen, K6rperpfiegemittel 19, 98 (1969); Chem. Abstr. 71, 42157c (1969). 993. SOKOLOFF, S., and R. SEGAL: Eudesmanolides Derived from Herbolide B. Tetra• hedron 33, 2837 (1977). 994. SORIA, E. L.: Analytical Study of the Distribution of Sesquiterpene Lactones in Different Species of Ambrosia. Bol. Soc. Quim. 41, 52 (1975); Chem. Abstr. 84, 28052b (1976). 995. SORM, F.: Medium Ring Terpenes. In: Fortschritte der Chemie organischer Natur• stoffe (ZECHMEISTER, L., ed.), Vol. 19, p. I. Wien: Springer. 1961.

24* 372 N. H. FISCHER, E. J. OLIVIER, and H. D. FISCHER:

996. SORM, F.: Sesquiterpenes with Ten-Membered Carbon Rings. 1. Agric. Food. Chern. 19,6(1971). 997. ~ Advances in Terpene Chemistry. Pure Appl. Chern. 21, 263 (1970). 99S. SORM, F., and L. DOLEJS: Guaianolides and Germacranolides. In: Chimie des substances naturelles (LEDERER, E., ed.). Paris: Herman. 1966. 999. SORM, F., M. SUCHY, M. HOLUB, A. LINEK, 1. HADINEC, and C. NOVAK: Crystalline Structure of the Addition Compound of Costunolide with Silver Nitrate. Tetrahedron Letters 1970, 1893. 1000. SOUCEK, M., V. HEROUT, and F. SORM: Constitution of Parthe noli de. Collect. Czech. Chern. Comm. 26, 803 (1961). 1001. SRIVASTAVA, S. C., S. K. PAKNIKAR, and S. C. BHATTACHARYYA: Simple Procedure for the Regeneration of a-Methylene-y-Lactones from the Amine-Adducts. Indian J. Chern. 8,201 (1970); Chern. Abstr. 72, 121727n (1970). 1002. ~ ~ ~ Biogenetic-Type Synthesis of Santamarin and Its Identity with Balchanin. Indian J. Chern. 8, 850 (1970); Chern. Abstr. 73, 131145f (1970). 1003. STAGNO D'ALCONTRES, G., M. GATTUSO, M. C. AVERSA, and C. CARISTI: The Structure of Graveolide, A New Sesquiterpene Lactone. Gazz. Chim. Ital. 1973, 239; Chern. Abstr. 79, 53614r (1973). 1004. STAHL, E., and S. N. DATTA: New Sesquiterpenoids of the Ground Ivy (Glechoma hederacea). Liebigs Ann. Chern. 1972, 757, 23; Chern. Abstr. 77, 98721 y (1972). 1005. STEELE, J. W., J. B. STENLAKE, and W. D. WILLIAMS: The Structure of Aristolactone. J. Chern. Soc. (London) 1959, 3289. 1006. STEELINK, C., and J. C. SPITZER: Sesquiterpene Lactones in Chemotaxonomy. Phytochem. 5, 357 (1966). 1007. STEFANOVIC, M., A. JOKIC, A. BEHBUD, and D. JEREMIC: New Sesquiterpenic Lactones from Ambrosia artemisiifoZia L. 8-acetoxy-3-oxopseudoguaian-6,12-olide and 4- hydroxy-3-oxopseudoguaian-6,12-olide. Bull. Acad. Serbe. Sci. Arts Cl. Sci. Math. Nat. Sci. Nat. 1976, 54; Chern. Abstr. 87, 35891 q (1977). ]oOS. STEFANOVIC, M., S. SOLUJIC, D. JEREMIC, A. JOKIC, D. MILJKOVIC, and S. VELIMIROVIC: Chemical Transformations of Arteannuin B ~ Cadinane Sesquiterpenic Lactone ~ Isolated from Artemisia annua L. Glas. Hem. Drus. Beograd. 42, 227 (1977); Chern. Abstr. 87, 168213s (1977). 100S a. STERNHELL, S.: Correlation of Interproton Spin-Spin-Coupling Constants with Structure. Quart. Rev. (Chern. Soc. London) 23, 236 (1969). 1009. STEVENSON, D. S., and C. J. W. BROOKS: Separation and Characterization of A3 _ and A4l1SI-Cyclopyrethrosin Acetates Via Chromatography on a Lipophilic Dextran Gel. J. Chromatogr. 75, 308 (1973); Chern. Abstr. 78, 84558j (1973). 10]0. ST. PYREK, J. : Isolation of Gaillardin from Flowers of Inula britannica L. Rocz. Chern. 51, 1277 (1977); Chern. Abstr. 87, 197230a (1977). ]o10a. ~ Terpenes of Compo sitae Plants. Part V. Sesquiterpene Lactones of Lactuca serriola L. The Structure of 8-Deoxylactucin and the Site of Esterification of Lactu• picrin. Rocz. Chern. 51, 2165 (1977). 1011. STOCKLIN, W., T. G. WADDELL, and T. A. GEISSMAN: Circular Dichroism and Optical Rotatory Dispersion of Sesquiterpene Lactones. Tetrahedron 26, 2397 (1970). 1012. SUCHY, M.: The Structure of Balchanin, a Sesquiterpenic Lactone of Santonin Type from Artemisia balchanorum H. Krash. Collect. Czech. Chern. Comm. 27, 2925 (1962). 1013. SUCHY, M., L. DOLEJS, V. HEROUT, F. SORM, G. SNATZKE, and J. HIMMELREICH: The Constitution of Jurineolide, a New Germacranolide from Jurinea cyanoides (L.) Rchb. Collect. Czech. Chern. Comm. 34, 229 (1969). 1014. SUCHY, M., and V. HEROUT: Calendin ~ The Bitter Principle from Calendula offici• naZis L. Collect. Czech. Chern. Comm. 26, 890 (1961). The Biogenesis and Chemistry of Sesquiterpene Lactones 373

1015. -- Identity of the Bitter Principle from Centaurea stoebe (L.) Sch. et Theil. Collect. Czech. Chern. Comm. 27, 1510 (1962). 1016. SUCHY, M., V. HEROUT, and F. SORM: Proof of Structure of Arctiopicrin with a Note on its Stereochemistry. Collect. Czech. Chern. Comm. 24, 1542 (1959). 1017. --- On the Nature of Arctiopicrin - The Unsaturated Lactone from Arctium minus Bernh. Collect. Czech. Chern. Comm. 22, 1902 (1957). 1018. --- On Hydrogenation Products of Cynaropicrin, The Bitter Principle of Artichoke (Cynara scolymus L.). Collect. Czech. Chern. Comm. 25, 507 (1960). 1019. --- Structure of Cynaropicrin. Collect. Czech. Chern. Comm. 25,2777 (1960). 1020. --- Lactones of the Germacranolide Group and Their Stereochemical Relationship. Collect. Czech.·Chem. Comm. 28,1715 (1963). 1021. --- The Proof of Existence and Structure of Hydroxycostunolide, a Sesqui• terpenic Lactone of Germacrane Type in Artemisia balchanorum H. Krash. Collect. Czech. Chern. Comm. 28, 1618 (1963). 1022. --- On Terpenes CLV. Structure of Damsine, a Sesquiterpenic Lactone from Ambrosia maritima L. Collect. Czech. Chern. Comm. 28,2257 (1963). 1023. --- Isolation and Structure of Scabiolide, Further Sesquiterpene Lactone with a Ten-Membered Ring in Molecule. Collect. Czech. Chern. Comm. 27, 1905 (1962). 1024. --- Absolute Configuration of Cnicin and Scabiolide. Collect. Czech. Chern. Comm. 27, 2398 (1962). 1025. --- Geometry of Double Bonds in the Ten-Membered Ring of Costunolide. Collect. Czech. Chern. Comm. 31, 2899 (1966). 1026. --- Proof of Structure of Guaianolides Artabsin and Arborescin. Collect. Czech. Chern. Comm. 29, 1829 (1964). 1027. --- The Structure of Salonitolide, A Sesquiterpenic Lactone of Germacrane Type from Centaurea salonitana Vis. Collect. Czech. Chern. Comm. 30, 2863 (1965). 1028. SUCHY, M., V. HEROUT, F. SORM, P. DE MAYO, A. N. STARRATT, and J. B. STOTHERS: The Constitution of Arctiopicrin. Tetrahedron Letters 1964, 3907. 1029. SUCHY, M., Z. SAMEK, V. HEROUT, and F. SORM: The Structure of Salonitenolide, a Sesquiterpenic Lactone of Germacrane Type from Centaurea salonitana Vis. Collect. Czech. Chern. Comm. 32, 2016 (1967). 1030. ---- The Structure and Absolute Configuration of Scabiolide. Collect. Czech. Chern. Comm. 33, 2238 (1968). 1031. ---- Revision of Structure of Artiopicrin, Cnicin and Scabiolide. Collect. Czech. Chern. Comm. 30, 3473 (1965). 1032. ---- Constitution and Configuration of Albicolide, a New Germacranolide from Jurinea albicaulis. Collect. Czech. Chern. Comm. 32, 3934 (1967). 1033. SUCHY, M., Z. SAMEK, V. HEROUT, R. B. BATES, G. SNATZKE, and F. SORM: Consti• tution and Configuration of Pelenolides, a New Group of Sesquiterpene Lactone Germacranolides. Collect. Czech. Chern. Comm. 32, 3917 (1967). 1034. SUMI, M.: The Constitution and Stereochemistry of Artemisin. J. Amer. Chern. Soc. 80, 4869 (1958). 1035. SUNDARARAMAN, P., and R. S. McEWEN: Crystal and Molecular Structure of Parthe• mollin [3,3a,4,5,6,81X-Hexahydro-7 -(I-hydroxy-3-oxobutyl)-6-methyl-3-methylenecyc• lohepta[b]furan-2-one. J. Chern. Soc. Perkin Trans. II 1975,440. 1036. SUNDARARAMAN, P., R. S. McEWEN, and W. HERZ: Constituents of Iva Species. Stereochemistry of Parthemollin and Related Xanthanolides. Tetrahedron Letters 1973, 3809. 1037. SUTHERLAND, J. K.: Regio- and Stereo-Specificity in the Cyciization of Medium Ring 1,5-Dienes. Tetrahedron 30, 1651 (1974). 1038. SUZUKI, T., M. TANEMURA, T. KATO, and Y. KITAHARA: Synthesis of Cinnamolide. Bull. Chern. Soc. Japan 43, 1268 (1970); Chern. Abstr. 73, 25681 t (1970). 374 N. H. FISCHER, E. J. OLIVIER, and H. D. FISCHER:

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References (Addendum)

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1213. CANE, D. E., and R. B. NACHBAR: Stereochemical Studies of Isoprenoid Bio• synthesis. Biosynthesis of Fomannosin from [1,2-13 C 21 Acetate. 1. Amer. Chern. Soc. 100, 3208 (1978). 1214. CICCI6, J. F., and J. G. CALZADA: Glabberin, a New Heliangolide from Eupatorium glaberrimum. Abstract Book, V. International Symposium for the Chemistry of Natural Products, Monterrey, , April 26-29, 1978. 1215. CORBET, J. P., and C. BENREZA: Allergenic a-Methylene-y-butyrolactones. A One• Carbon Degradation of Isoalantolactone via Pummerer Rearrangement of Sulfoxides. Canad. J. Chern. 57, 213 (1979). 1216. CORTES, E., M. C. ROMERO, and 1. ROMO: Mass Spectrometry of Sesquiterpenic Lactones of the Pseudoguaianolide Series II. Rev. Latinoamer. Quim. 8, 168 (1977). 1217. DANISHEFSKY, S., M. HIRAMA, K. GOMBATZ, T. HARAYAMA, E. BERMAN, and P. SCHUDA: Stereospecific Total Synthesis of DL-Pentalenolactone. J. Amer. Chern. Soc. 100,6536 (1978). 1217a. DE BERNARDI, M., G. FRONZA, G. MELLERIO, G. VIDARI, and P. VITA-FINZI: New Sesquiterpene Hydroxylactones from Lactarius Species. Phytochem. 18, 293 (1979). 1218. DEL AMO, S., and A. L. ANAYA: Effect of Some Sesquiterpenic Lactones on the Growth of Certain Secondary Tropical Species. J. Chern. Eco!. 4, 305 (1978). Chern. Abstr. 89, 103933y (1978). 1219. DEL AMO, R. S., and A. GOMEZ-POMPA: Variability in Ambrosia cumanensis (Com• po sitae). Syst. Bot. 1, 363 (1976); Chern. Abstr. 89, 39436j (1978). 1220. DOMINGUEZ, X. A., O. R. FRANCO, G. CANO, S. GARCIA, and V. PENA: Mexican Medicinal Plants. XXXII. Terpenoids of the Ether Extracts of Two Celastraceae, Mortonia greggi Gray and M. palmeri Hems!. Rev. Latinoamer. Quim. 9, 33 (1978). 1221. EDGAR, M. T., A. E. GREENE, and P. CRABBE: Stereoselective Synthesis of (-)• Estafiatin. J. Organ. Chern. (USA) 44, 159 (1979). 1222. EDWARD, J. T., and M. J. DAVIS: Reaction of Santonin with Hydroxylamine. J. Organ. Chern. (USA) 43, 536 (1978). 1223. EL-FERALY, F. S., and Y. M. CHAN: Isolation and Characterization of the Sesqui• terpene Lactones Costunolide, Parthenolide, Costunolide Diepoxide, Santamarine, and Reynosin from Magnolia grandiflora L. J. Pharm. Sci. 67, 347 (1978). 1224. FROBORG, J., and G. MAGNUSSON: Construction of the Vellerane Skeleton with Total Syntheses of Racemic Velleral, Vellerolactone and Pyrovellerolactone, Revised Structures. J. Amer. Chern. Soc. 100, 6728 (1978). 1225. FURUKAWA, H., M. ITOIGAWA, N. KUMAGAI, K. ITO, A. T. MCPHAIL, and K. D. ONAN: Isolation and Structure Determination of 4-0-Tigloyl-II,13-Dihydro• autumnolide, a New Sesquiterpene Lactone from North Carolina Helenium autumnale L. Chern. Pharm. Bull. 26, 1335 (1978). 1226. GONZALEZ, A. G., J. M. ARTEAGA, B. M. FRAGA, M. G. HERNANDEZ, and J. FAYOS: The Structure of Jhanilactone. Experientia 34, 554 (1978); Chern. Abstr. 89, 75406h (1978). 1227. GONZALEZ, A. G., J. T. BARROSO, H. LOPEZ DORTA, J. R. LUIS, and F. RODRIGUEZLUIS: Compounds from Umbelliferae 20. Components of Heracleum pyrenaicum Lam. An. Quim. 74, 832 (1978). 1228. GONZALEZ, A. G., 1. BERMEJO, J. M. AMARO, G. M. MASSANET, A. GALINDO. and I. CABRERA: Sesquiterpene Lactones from Centaurea linifolia Yah!. Canad. J. Chern. 56,491 (1978). 1229. GONZALEZ, A. G., 1. BERMEJO, J. L. BRETON, A. GALINDO, and G. M. MASSANET: Cu-Hydroxylation of Eudesmanolides. Rev. Latinoamer. Quim. 9, 78 (1978). 1230. GONZALES, A. G., 1. BERMEJO, I. CABRERA, G. M. MASSANET, H. MANSILLA, and A. GALINDO: Two Sesquiterpene Lactones from Centaurea canariensis. Phytochem. 17, 955 (1978). 384 N. H. FISCHER, E. J. OLIVIER, and H. D. FISCHER:

1231. GONZALEZ, A G., J. BERMEJO, H. MANSILLA, A GALINDO, 1. M. AMARO, and G. M. MASSANET: Structure and Absolute Configuration of Gallicin, a New Ger• macranolide from Artemisia. J. Chern. Soc. Perkin Trans I 1978, 1243. 1232. GONZALEZ, A G., 1. BERMEJO, and G. M. MASSANET: Contribution to the Chemo• taxonomical Study of the Genus Centaurea. Structural Determination of Sesquiter• penic Lactones Present in Centaurea of the Canary Islands and the Iberian Peninsula. Rev. Latinoamer. Quim. 8, 176 (1977). 1233. GONZALEZ, A G., and A GALINDO: Sesquiterpene Lactones in Umbelliferae. Contrib. Pluridiscip. Syst., Actes Symp. Int., 2nd 1977, 178, p. 365. 1234. GONZALEZ, A G., and B. GARCIAMARRERO: Stereochemistry of Sesquiterpenic Lactones of Amberboa /ippii DC. An. Quim. 74, 1121 (1978). 1235. GOVINDAN, S. V., and S. C. BHATTACHARYYA: Oxymercuration of Some Sesquiter• pene Lactones, Costunolide, Dihydrocostunolide, Dehydrocostuslactone and Di• hydrodehydrocostuslactone. Indian J. Chern. Sect. B 16, I (1978). 1236. -- Transformations of Isoalantolactone and Oxidation of 8,11 a-H-Eudesm-4- en-S,13-olide. Indian J. Chern. Sect. B 16, 271 (1978). 1237. GRIECO, P. A., T. OGURI, S. BURKE, E. RODRIGUEZ, G. T. DE TITTA, and S. FORTIER: Structure, Absolute Configuration, and Synthesis of Stramonin-B, a New Cytotoxic Pseudoguaianolide.1. Organ. Chern. (USA) 43, 4552 (1978). 1238. GRIECO, P. A, T. OGURI, S. GILMAN, and G. T. DE TITTA: Total Synthesis of(±)-Erio• lanin. J. Amer. Chern. Soc. 100, 1616 (1978). 1239. HERZ, W., R. DE GROOTE, R. MURARI, and 1. F. BLOUNT: Sesquiterpene Lactones of Eupatorium recurvans. 1. Organ. Chern. (USA) 43, 3559 (1978). 1240. HERZ, W., and N. KUMAR: Sesquiterpene Lactones of Baltimora recta. Phytochem., submitted. 1241. HERZ, W., R. MURARI, and J. F. BLOUNT: Revised Structures of Pleniradin and Baileyin and their Bearing on the Biogenesis of Helenanolides. J. Organ. Chern. (USA),44, IS73 (1979). 1242. HERZ, W., R. MURARI, and S. V. GOVINDAN: Sesquiterpene Lactones of Eupatorium anomalum and Eupatorium mohrii. Phytochem.18, 1337 (1979). 1242a. HOFFMANN, J. J., S. D. JOLAD, S. J. TORRANCE, D. 1. LUZBETAK, R. M. WIEDHOPF, and J. R. COLE: Odoratin and Paucin: Cytotoxic Sesquiterpene Lactones from Baileya pauciradiata (Compositae). J. Pharm. Sci. 67, (II) 1633 (1978). 1243. HOLUB, M., O. MOTL, and Z. SAMEK: The Structure and Relative and Absolute Configurations of the Sesquiterpenic Lactones Gradolide and Polhovolide from Laserpitium siler L. Collect. Czech. Chern. Commun. 43, 2471 (1978). 1244. HOLUB. M .. Z. SAMEK, S. VASICKOVA, and M. MASOJIDKOVA: II-Hydroxy-I~H, 5~H, 6aH, 7aH-Guaian-6,12-olides: Relative and Absolute Configurations of the Sesquiterpenic Lactones Montanolide, Isomontanolide, Acetylisomontanolide and Related Substances. Collect. Czech. Chern. Commun. 43, 2444 (1978). ! 245. IMAKURA, Y.. K. H. LEE, D. SIMS, and 1. H. HALL: Structural Elucidation of the Novel Antitumor Sesquiterpene Lactone, Microlenin, from Helenium microcephalum. 1. Pharm. Sci. 67, 1228 (197S). 1246. INAYAMA, S., T. KAWAMATA, and T. OHKURA: The Chemical Transformation to Pulchellon from Pulchellin. Tetrahedron Letters 18, 1557 (1978). 1247. ISOBE, M., H, lIO, T. KAWAI, and T. GOTO: Synthesis of Sesquiterpene Anti• tumor Lactones. A New Stereo controlledTotal Synthesis of (±)-Vernolepin. 1. Amer. Chern. Soc. 100, 1940 (197S). 1248. ITO, T., T. SHIMIZU, Y. FUJIMOTO, and T. TATSUNO: 5a-Hydroxy-4aH,I,6,II~H­ guai-2, I 0(15)-dien-6, 12-olide. Acta Crystallogr. B, 34, 1009 (1978). 1248a. JANKOWSKI, K.: Utilisation de la Simulation dans l'Analyse des Spectres RMN Enregistres en Presence de Reactifs Depla9ants. Rev. Latinoamer. Quim. 9, 175 (1978). The Biogenesis and Chemistry of Sesquiterpene Lactones 385

1249. JIZBA, J., Z. SAMEK, L. NOVOTNY, E. NAJDENOVA, and A BOEVA: Components of Sene• cio nemorensis Var. bulgaricus (Vel. Pro. Sp.). Collect Czech. Chern. Commun. 43, 1113 (1978). 1250. JosEPH-NATHAN, P.: Carbon-13 NMR of Pyrethrosin from Chrysanthemum. Rev. Latinoamer. Quim. 9, 36 (1978). 1251. KARAWYA, M. S., S. H. HILAL, M. S. HIFNAWY, and S. S. EL-HAWARY: Isolation and Preliminary Pharmacological and Microbiological Screening of Cnicin from Centaurea calitrapa L. growing in Egypt. Egypt. J. Pharm. Sci. 16, 445 (1977); Chern. Abstr. 89, l60096b (1978). 1252. KARLSSON, B., A M. PILOTTI, and A C. SODERHOLM: Structure of the Hydrogen Adduct of Spicatine, a Sesquiterpenoid Lactone. Acta Crystallogr. B, 35, 244 (1979). 1253. KARWE, M. V., N. R. DESHPANDE, S. V. HIREMATH, G. H. KULKARNI, and G. R. KELKAR: Preparation of some Sesquiterpenic Conjugated Endo- and Exo-cr-Methy• lene-y-Lactones. Indian J. Chern. Sect. B 16, 539 (1978). 1254. KIECZYKOWSKI, G. R., and R. H. SCHLESSINGER: Total Synthesis of (±)-Verno• lepin. J. Amer. Chern. Soc. 100, 1938 (1978). 1255. KUPCHAN, S. M., J. W. ASHMORE, and A T. SNEDEN: Structure-Activity Relation• ships Among in vivo Active Germacranolides. 1. Pharm. Sci. 6, 865 (1978). 1256. LANSBURY, P. T., and A K. SERELIS: A Facile Entry to Pseudoguaianes. Total Synthesis of Damsinic Acid. Tetrahedron Letters 22, 1909 (1978). 1257. LEE, K. H., T. IBuKA, E. C. MAR, and 1. H. HALL: Antitumor Agents. 31. Hele• nalin Sym-Dimethylethylenediamine Reaction Products and Related Derivatives. J. Med. Chern. 21, 698 (1978). 1258. LEQUESNE, P. W., S. B. LEVERY, M. D. MENACHERY, T. F. BRENNAN, and R. F. RAFFAUF: Novel Modified Germacranolides and Other Constituents of Eremanthus elaeagnus Schultz - Bip (Compositae). J. Chern. Soc. Perkin Trans I 1978, 1572. 1259. LEVAN, N., and N. H. FISCHER: Three New Melampolide Sesquiterpenes, Polymatin A, Band C, from Polymnia maculata Cav. var. maculata. Phytochem. 18, 851 (1979). 1260. LINEK, A., and C. NOVAK: Refinement of the Structure of the Costunolide-Silver Nitrate Complex. Acta Crystallogr. B 34, 3369 (1978). 1261. LOPEZ DE LERMA, J., J. FAYOS, S. GARCIA-BLANCO, and M. MARTINEZ-RIPOLL: Centaurepensin. A Redetermination of its Absolute Configuration by X-Ray Crystal• lography. Acta Crystallogr. B 34, 2669 (1978). 1262. MALLABAEV, A., U. RAKHMANKULOV, and G. P. SIDYAKIN: Lactones from Achillea santolina. Khim. Prir. Soedin 1978, (4), 530; Chern. Abstr. 89, 193848b (1978). 1263. MANE, B. M., S. V. HIREMATH, and G. H. KULKARNI: Selenium Dioxide Oxidation of Saussurealactone. Curro Sci. 47, 677 (1978); Chern. Abstra. 90, 39056f (1979). 1264. MANCHAND, P. S., and 1. F. BLOUNT: Stereo structures of Neurolensins A and B, Novel Germacranolide Sesquiterpenes from Neurolaena lobata (L.). R. Br. J. Organ. Chern. (USA) 43, 4352 (1978). 1265. MARSHALL, J. A., and P. G. M. WUTS: Stereocontrolled Total Synthesis of cr- and ~­ Santonin. J. Organ. Chern. (USA) 43, 1086 (1978). 1266. MASAYOSH!, A, K. TAJlMA, and K. TAKAsE: Total Synthesis of Saussurea Lactone. Chern. Letters 1978, 617. 1267. MATSUEDA, S., M. NAGAKI, 1. ICHITA, Y. MASUCH!, and M. KOREEDA: Structure of Meridianone. Abstract Book, ACS-CSJ Chemical Congress, Honolulu, Hawaii, April 2-6, 1979. Organic Chemistry, paper 571. 1268. MUKHAMETZHANOV, M. N., ABDRAKHMANOV, O. A., and S. M. ADEKENOV: Sesqui• terpene Lactones from Artemisia austisca. Teor. Osnovy Pererab. Mineral'n. i Organ. Syr'ya. 4, 73 (1977); Chern. Abstr. 89, 39281 n (1978).

Fartschritte d. Chern. arg. Naturst. 38 25 386 N. H. FISCHER, E. 1. OLIVIER, and H. D. FISCHER:

1269. MURAl, A., M. ONO, A. ABIKO, and T. MASAMUNE: Synthesis of Phytuberin. J. Amer. Chern. Soc. 100,7751 (1978). 1270. NADGOUDA, S. A., G. K. TRIVEDI, and S. C. BHATTACHARYYA: Sensitized Photo• oxygenation of IX-Cyc1ocostunolide and Dihydro IX-Cyc1ocostunolide: A Biogenetic Type Transformation of Costunolide to Santonin. Ind. J. of Chern. Sect. B 16, 16 (1978). 1271. NAIDENOVA, E., and E. BLOSHIK: Parthenolides in Inula aschersoniana Ika, Variety Aschersoniana Staj., Stef., and Kitan. Farmatsiya (Sofia) 28, 26 (1978); Chern. Abstr. 89, 193899u (1978). 1272. NAIDENOVA, E., N. L. DRYANOVSKA, and B. DROZDZ: Nitrogen-Containing Deri• vatives of the Sesquiterpene Lactone Grossheimin. Probl. Farm 5, 85 (1977); Chern. Abstr. 89, l100l4c (1978). 1273. NARAIN, N. K.: Spectroscopic Studies of Fasciculide-B, a New Sesquiterpene Lactone from the Leaves of Vernonia Jasciculata Michx. Spectrosc. Letters 11, 267 (1978). 1274. OGURA, M., G. A. CORDELL, and N. R. FARNSWORTH: Anticancer Sesquiterpene Lactones of Michelia compressa (Magnoliaceae). Phytochem. 17, 957 (1978). 1275. OHFUNE, Y., P. A. GRIECO, C. L. J. WANG, and G. MAJETICH: Stereospecific Total Synthesis ofDL-Helenalin. A General Route to Helenanolides and Ambrosano• lides. J. Amer. Chern. Soc. 100,5946 (1978). 1276. OHNO, N., and T. 1. MABRY: Germacranolides from Helianthus moWs Lam. Phyto• chern. 18, 1003 (1979). 1276a. OHSAWA, T.: Root Formation and Physiologically Active Substances. Kagaku to Seibutsu 16 (10),644 (1978); Chern. Abstr. 90, 5l345g (1979). 1277. ORTEGA, A., R. MARTINEZ, and A. ROMO DE VIVAR: Elemanolides of Verbesina Aff Stricta. Structure of Zempoalines A and B. Rev. Latinoamer. Quim. 8, 166 (1977). 1278. PAKNIKAR, S. K., J. VEERAVALLI, and J. K. KIRTANY: Revised Structures for Iselin and Iliensin and the Identity of the Former with Archangelin. Experientia 34, 553 (1978). 1279. PETTIT, G. R., C. L. HERALD, M. S. ALLEN, R. B. VON DREELE, L. D. VANELL, J. P. Y. KAO, and W. BLAKE: The Isolation and Structure of Aplysistatin. J. Amer. Chern. Soc. 99, 262 (1977). 1280. PICMAN, A. K., R. H. ELLIOTT, and G. H. N. TOWERS: Insect Feeding Deterrents Property of Alantolactone. Biochem. Systematics and Ecology 6, 333 (1978). 1281. QUIJANO, L., D. BLOOMENSTIEL, and N. H. FISCHER: Tetraludin A, Band C, Three New Melampolides from Tetragonotheca ludoviciana (Compo sitae, Heliantheae). Phytochem. 18, 1529 (1979). 1281a. QUIJANO, L., and N. H. FISCHER: New Melampolides from Tetragonotheca ludo• viciana. To be published. 1282. -- Melfusin, a New Germacrolide from Melampodium diffusum (Compo sitae, Heliantheae). To be published. 1283. QUIJANO, L., A. ROMO DE VIVAR, and T. RJOs: Calea zacatechichi Components. Structure of Calein A and B. Rev. Latinoamer. Quim. 9, 86 (1978). 1283a. --- Revision of the Structures of Calein A and B. Phytochem., in press. 1284. RANIERI, R. L., and G. 1. CALTON: Quadrone, A New Antitumor Agent from Aspergillus terreus. Tetrahedron Letters 6, 499 (1978). 1284a. RODRIGUEZ, E.: Allergenic and Irritant Plant Constituents. Rev. Latinoamer. Quim. 9, 125 (1978). 1284b. RODRIGUEZ-HAHN, L., M. JIMENEZ, E. DIAZ. C. GUERRERO, A. ORTEGA, and A. ROMO DE VIVAR: The Revised Structure of Mortonin. Tetrahedron 33, 657 (1977). 1284c. ------Photolysis of Mmtonin. Tetrahedron 33, 661 (1977). The Biogenesis and Chemistry of Sesquiterpene Lactones 387

1285. RODRIGUEZ-HAHN, L., M. JIMENEZ, M. OLIVEROS, and E. DIAZ: Isolation and Struc• ture of Mortonins B, C and D. Rev. Latinoamer. Quim. 8, 161 (1977). 1286. ROMO, J., L. RODRIGUEZ-HAHN, and C. VICHIDO: Oxidation Experiments in Sesqui• terpenic Lactones. Rev. Latinoamer. Quim. 8, 149 (1977). 1286a. ROMO DE VIVAR, A., G. DELGADO, C. GUERRERO, J. RESENDIZ, and A. ORTEGA: Estudio de Viguieras. Estructura de la Viguiepinina y Correcion de la Viguiestenina. Rev. Latinoamer. Quim. 9, 171 (1978). 1287. ROQUE, N. F., Z. S. FERREIRA, O. R. GOTTLIEB, R. L. STEPHENS, and E. WENKERT: The Structure of Ocotealactol, a New Eudesmanolide. Rev. Latinoamer. Quim. 9, 25 (1978). 1288. RUECKER, G., and M. SCHIKARSKI: Conversion ofIsofuranodien to Germacranolide. Arch. Pharm. 311, 754 (1978); Chern. Abstr. 90, 23293v (1979). 1288a. RUSTAIYAN, A., L. NAZARIANS, and F. BOHLMANN: Two New Germacranolides from Onopordon leptolepis DC. Phytochem. 18, 883 (1979). 1288b. --- Two New Elemanolides from Onopordon leptolepis. Phytochem. 18, 879 (1979). 1288c. RUSTAIYAN, A., A. NIKNEJAD, W. H. WATSON, V. ZABEL, T. J. MABRY, G. YABUTA, and S. B. JONES, Jr.: Dihydroelephantopin, a New Tumor Inhibitor from Elephan• topus tomentosus L. (Compositae). Rev. Latinoamer. Quim. 9, 200 (1978). 1289. SAIDKHODZHAEV, A. I.: Structure of Tenuferin, Tenuferinin and Tenuferidin. Khim. Prir. Soedin. 14, 70 (1978); eng!. edit.; p. 55. 1290. SAMEK, Z., and J. HARMATHA: Use of Structural Changes for Stereochemical Assignments of Natural ()(-Exomethylene y-Lactones of the Germacra-I(l0),4-Dieno• lide Type on the Basis of Allylic and Vicinal Couplings of Bridgehead Protons. Hydrogenation of Endocyclic Double Bonds. Collect. Czech. Chern. Commun. 43, 2779 (1978). 1291. SEAMAN, F. c., and N. H. FISCHER: New Sesquiterpene Lactones from Melampodium linearilobum (Compositae, Heliantheae). To be published. 1292. -- New Melampolides from Tetragonotheca helianthoides (Compo sitae, Helian• theae). To be published. 1293. SEMMELHACK, M. F., A. YAMASHITA, J. C. TOMEscH, and K. HIROTSU: Total Synthesis of Confertin via Metal-Promoted Cyclization-Lactonization. J. Amer. Chern. Soc. 100, 5565 (1978). 1294. SERKEROV, S. V.: A Study of Badkhyzinin. Khim. Prir. Soedin. 13, 787 (1977); eng!. edit.: p. 663. 1295. SERKEROV, S. V., and A. N. ALESKEROVA: The Structure of A Sesquiterpene Lactone from Artemisia/ragrans. Khim. Prir. Soedin. 14,75 (1978); eng!. edit.: p. 59. 1296. SETO, H., T. SASAKI, H. YONEHARA, and J. UZAWA: Studies on the Biosynthesis of Pentalenolactone. Part I. Application of Long Range Selective Proton Decoupling (LSPD) and Selective 13C_{' H) Noe in the Structural Elucidation of Pentaleno• lactone G. Tetrahedron Letters 10, 923 (1978). 1297. SHAM'YANOV, I. D., A. MALLABAEV, and G. P. SIDYAKIN: Structure of the Sesqui• terpene Lactone Elegin. Khim. Prir. Soedin. 14,442 (1978); Chern. Abstr. 89, 197740h (1978). 1298. SHIBATA, H., and S. SHIMIZU: Three Chemovars of Petasites japonicus Maxim. Agric. Bio!. Chern. 42, 1427 (1978); Chern. Abstr. 89, 193827u (1978). 1299. SINGH, A. N., V. V. MHASKAR, and S. DEV: Synthesis of Jalaric Ester-I, Possible Key Compound in the Elaboration of Lac Resin by Laccifer lacca Kerr. Tetra• hedron 34, 595 (1978). 1300. TARAsov, V. A., N. D. ABDULLAEV, S. Z. KASYMOV, G. P. SIDYAKIN, and M. R. YAGUDAEV: Structure of Hanphyllin. Khim. Prir. Soedin. 14, 78 (1978); eng!. edit.: p.62.

25* 388 N. H. FISCHER, E. J. OLIVIER, and H. D. FISCHER:

1301. TORII, S., K. UNEYAMA, and H. ICHIMURA: Synthesis of (±)-Norisoambreinolide and (±)-Isoambrox. J. Organ. Chern. (USA) 43, 4680 (1978). 1302. TOWERS, G. H. N., J. C. MITCHELL, E. RODRIGUEZ, F. D. BENNETT, and S. P. V. RAo: Biology and Chemistry of Parthenium hysterophorus L, a Problem Weed in India. J. Sci. Ind. Res. 36, 672 (1977); Chern. Abstr. 89, 72943v (1978). 1302a. ULUBELEN, A., N. ATES, and T. NISHIDA: Istanbulin C, a Novel Sesquiterpene Lactone from Smyrnium connatum. Phytochem. 18, 338 (1979). 1303. URMANOVA, F. F., S. Z. KASYMOV, and G. P. SIDYAKIN: Sesquiterpene Lactones from Pseudohandelia (Umbellifera). Khim. Prir. Soedin. 14, 530 (1978); Chern. Abstr. 89, 176474j (1978). 1304. WENDER, P. A., and J. C. LECHLEITER: A Photochemically Mediated [4C+2C] Annelation. Synthesis of (± )-lO-Epijuneno!. J. Amer. Chern. Soc. 100, 4321 (1978). 1305. WILSON, S. R., and D. T. MAo: An Intramolecular Diels-Alder Route to Eudes• mane Sesquiterpenes. J. Amer. Chern. Soc. 100, 6289 (1978). 1306. YABUTA, G., J. S. OLSEN, and T. J. MABRY: Sesquiterpene Lactones from the Genus Zaluzania (Compositae: Heliantheae). Rev. Latinoamer. Quim. 9, 83 (1978). 1307. YAMAKAWA, K., K. NISHITANI, and K. AZUSAWA: Chemical Transformation of a• Santonin into Sesquiterpene a-Methylene-y-Lactones, Douglanin, and Ludovicin A and B. Heterocycles 9, 499 (1978). 1308. YAMAKAWA, K., K. NISHITANI, and A. MURAKAMI: Chemical Transformation of a-Santonin into Yomogin, Pinnatifidin, and 8-Epiartimisin. Abstract Book, ACS• CSJ Chemical Congress, Honolulu, Hawaii, April 2-6, 1979. Organic Chemistry, paper 535. 1309. YAMAKAWA, K., and T. TOMINAGA: ll-Exo-Methylene-a-Tetrahydrosantonin. Japan. Kokai 78, 759 (1978); Chern. Abstr. 89, 24563z (1978). 1310. -- ll-Exo-Methylenesantonin. Japan Kokai 78, 758 (1978); Chern. Abstr. 89, 24564a (1978). 1310a. YUNUSOV, A. I., G. P. SIDYAKIN, and D. KURBANOV: Cumambrins A and B from Tanacetum santolina. Khim. Prir. Soedin 5, 656 (1978); Chern. Abstr. 90, 51410z (1979). 1311. YusuPov, M. I., S. Z. KASYMOV, N. D. ABDULLAEV, G. P. SIDYAKIN, and M. R. YAGUDAEV: A New Lactone, Isoridentin, from Achillea biebersteinii. Khim. Prir. Soedin. 13,800 (1977); eng!. edit.: p. 674. 1312. ZAKHAROV, P. I., P. B. TERENTLEV, O. A. KONOVALOVA, and K. S. RYBALKO: Mass-Spectrometric Study of the Sesquiterpene Lactone Grossmisin and Its Derivatives. Khim. Prir. Soedin. 13, 344 (1977); eng!. edit.: p. 293. 1313. ---- Mass-Spectrometric Study of the Sesquiterpene Lactone Germanin A and its Derivatives. Khim. Prir. Soedin 14, 337 (1978); Chern. Abstr. 89, 147083a (1978).

Index of Charts Tabulating the Different Structural Types of Sesquiterpene Lactones

Bakkenolides (Fukinanolides) (Chart VIII-5) ...... 261 Drimanolides (Chart IX-2) ...... 266 Elemanolides and biogenetic derivatives (Chart VI-I) ...... 214 Addendum ...... 304 Eremophilanolides and biogenetic derivatives (Chart VIllA) 259 Addendum ...... 305 The Biogenesis and Chemistry of Sesquiterpene Lactones 389

Eudesmanolides and biogenetic derivatives (Chart IV-I) ...... 134 Addendum ...... 299 Fukinanolides (Chart VIII-5) ...... 261 Furanogermacranolides (Chart 1II-6) ...... 73 Addendum ...... 293 cis,cis-Germacranolides (Chart 1II-6) ...... 73 Addendum ...... 293 Germacranolides, special structural types, and stereochemically unestablished com- pounds (Chart III-8) ...... 76 Addendum ...... 293 Germacrolides, 7,6-lactonized (Chart III-2) ...... 61 Addendum ...... 293 Germacrolides, 7,8-lactonized (Chart III-3) ...... 65 Addendum ...... 293 Guaianolides and biogenetic derivatives (Chart V-I) ...... 166 Addendum ...... 300 seco-Guaianolides (Xanthanolides) (Chart V-2) ...... 187 Heliangolides and biogenetic derivatives (Chart III-5) ...... 69 Addendum ...... 293 Melampolides and biogenetic derivatives (Chart 1II-4) ...... 67 Addendum ...... 293 Picrotoxins (Chart IX-3) ...... 270 Pseudoguaianolides and biogenetic derivatives (Chart VII-I) ...... 224 Addendum ...... 304 Sesquiterpene lactones, special structural types (Chart IX-4) ...... 274 Addendum ...... 305 Tutinanolides (Chart IX-3) ...... 270

Index of Tables Containing the Various Structural Types of Sesquiterpene Lactones

Bakkenolides (Fukinanolides) (Table VIII-2) ...... 264 Drimanolides (Table IX-I) ...... 269 Elemanolides and Biogenetic Derivatives (Table VI-I) ...... 221 Addendum...... 317 Eremophilanolides and Biogenetic Derivatives (Table VIII-I) .. 262 Addendum ...... 319 Eudesmanolides and Biogenetic Derivatives (Table IV-2) ...... 157 Addendum ...... 314 Eudesmanolides and Derivatives of Known X-Ray Structures (Table IV-I) ...... 149 Fukinanolides (Table VIII-2) ...... 264 Germacranolides and Biogenetic Derivatives (Table 1II-3) ...... 116 Addendum ...... 308 390 N. H. FISCHER, E. J. OLIVIER, and H. D. FISCHER: Sesquiterpene Lactones

Germacranolides of Known X-Ray Structure (Table 111-2) ...... 95 Guaianolides and Biogenetic Derivatives of Known X-Ray Structures (Table V-I) ... 198 Guaianolides and Biogenetic Derivatives (Table V-2) ...... 199 Addendum ...... 315 Picrotoxins (Table IX-2) ...... 272 Pseudoguaianolides of Known X-Ray Structure (Table VII-I) ...... 239 Pseudoguaianolides and Seco-Derivatives (Table VII-2) ...... 246 Addendum ...... 318 Sesquiterpene Lactones, Common Side Chains in (Table II-I) ...... 56 Sesquiterpene Lactones, Special Structural Types (Table IX-3) ...... 282 Addendum ...... 320 Sesquiterpene Lactones of Undetermined Structure (Table X-I) ...... 286 Tutinanolides (Picrotoxins) (Table IX-2) ...... 272

(Received August 4. 1978) Author Index By

A. SIEGEL, Wien

Page numbers printed in italics refer to ReferenceS

Abbasov, R. M. 370 Amano, Y. 340 Abdakhmanov, O. A. 385 Amaro, J. M. 336,337,383,384 Abdel-Baset, Z.H. 321,355 Ananthasubramanian, L. 381 Abdullaev, N. D. 375,380,381,387,388 Anaya, A. L. 383 Abe, N. 321,371 Anchel, M. 333, 359 Abe, Y. 321 Andersen, N. H. 361 Abiko, A. 386 Anderson, G. D. 322, 336, 341, 343, 380 Abraham, W. R. 326, 332 Anderson, L. A. P. 322 Abu Shady, H. 321, 368 Anderson, W. K. 44 Achari, R. G. 321 Ando, M. 322,381 Acklin, W. 377 Andrews, G. C. 333 Adam,J.41 Anuforo, D. C. 353 Adams, R. 321 Aota, K. 322,341,343 Adams, T. W. 325, 338 Aoyama, K. 375 Addicott, F. A. 335 Appel, H. H. 322 Adekenov, S. M. 385 ApSimon, J. W. 340 Agafonova, N. V. 321 Aragon, R. 332 Aguilar, M. 365, 366 Aratani, T. 322,323 Aikman, M. J. 43 Arenson, K. R. 355 Akahane, A. 381 Arigoni, D. 322,377 Akiba, M. 34, 43, 44 Arkhipova, L. I. 322 Akyev, B. 321,358 Arteaga, J. M. 336, 383 Alanis, G. 365 Asada, Y. 359 Alauddin, M. 359 Asahina, Y. 322 Aleman, E. 322 Asaka, Y. 322 Aleskerova, A. N. 370,387 Asakawa, Y. 322,323,381,382 Ali, E. 322 Asher, J. D. M. 323 Aliev, R. K. 322 Ashmore,J. W. 352,385 Allen, G. R. Jr. 43 Asplund, R. O. 323, 358 Allen, M. S. 386 Aston, B. C. 333 Allison, A. J. 322 Ates, N. 388 Alper, H. 322 Aubad, Y. 332 Alston, R. E. 341 Auerbach, J. 44 Alvarado, S. 381 Aumeer, P. S. 323 Alvarez, C. 365 Aversa, M. C. 372 392 Author Index

Ayer, W. A. 323 Bertelli, D. J. 324 Aynehchi, Y. 352 Bertran, J. F. 322 Azuma, S. 358 Betancov, C. 324 Azusawa, K. 379,388 Beth Wu, 1. 362 Betkouski, M. 325,338,375 Babakhodzhaev, A. 323 Bezanson, G. S. 43 Bachelor, F. W.323 Bhacca, N. S. 325,378 Baehr, W. 359,378 Bhadane, N. R. 325, 349, 371 Baer, H. 379 Bhanot, O. S. 325 Bagirov, V. Y. 382 Bhat, K. L. 382 Bailey, J. H. 328 Bhat, S. V. 341,368 Baker, P. M. 335 Bhattacharyya, S. C. 291,324,325,348,352, Balasubramaniyan, P. 332 355,364,371,372,381,384,386 Baldwin, J. E. 31,44 Bhedi, D. N. 325 Banh-Nhu, C. 382 Bialecki, M. 325 Bankar, N. S. 220, 323 Bialek-Grygiel, G. 333 Bankovskaya, A. N. 367 Bianchi, E. 379 Ban'kovskii, A. 1. 327.328, 333, 334, 350, Bierner, M. W. 325 351,358.364,367,375 Birnbaum, G. L 325 Banks, C. M. 347 Bischt, N. P. S. 382 Bapat, B. V. 362 Bjeldanes, L. F. 325 Baranowska, E. 323 I Blake, W. 386 Barbatschi, F. 41 Bloomenstiel, D. F. 369,386 Barkemeyer, H. 351 Bloszyk, E. 325,368, 386 Barroso, J. T. 383 Blount, J. F. 45,341,342,343,377,384,385 Barton, D. H. R. 146, 149, 154, 323, 371 Blum, S. 290,382 Baruah, N. C. 382 Bobkiewicz, T. 325,344 Basey, K. 323 Bockman, O. C. 323 Basset, C. 349 Boeva, A. 385 Bates, R. B. 323,324,364,373 Bogucka-Ledochowska, M. 325,351 Batta, A. K. 370 Bohlmann, F. 290, 325, 326, 327, 330, 382, Batterham, T. J. 324 387 Bauer, L. 371,382 Bohonos, N. 41 Bawdekar, A. S. 324, 348 Bolliger, G. 363 Baxter, R. L. 352 Bond, R. P. M. 322 Beecham, A. F. 324 Bonde, E. K. 335 Begleiter, A. 4, 5, 42, 43 Borges, J. 382 Begley, M. J. 324 Borisov, V. N. 327 Behare, E. S. 324, 357 Borowski, E. 325,351 Behbud, A. 347. 372 Boryaev, K. 1. 359 Bell, C. L. 371 Bose, A. K. 377 Benesova, V. 324 Bosshard, H. 322 Bennett, F. D. 388 Boville, M. J. 327 Benreza, C. 292,382 Brackman, J. C. 330 Bentley, R. K. 324 Bradner, W. T. 18,43 Berger, D. 382 Braga de Oliveira, A. 382 Bergy, M. E. 41 Bratoeff, E. A. 366 Berman, E. 383 Braz Filho, B. 382 Bermejo Barrera, J. 324,336,337,383,384 Brecknell, D. J. 327 Bernady, K. F. 44 Brennan, T. F. 364,385 Bernal, 1. 324,378 Breton Funes, J. L. 324, 327, 336, 337, 338, Berryman, K. A. 371 383 Author Index 393

Brewster, J. W. 327 Chatterjie, N. 43 Brieger, G. 327 Chavez, P. 1. 356 Brindopke, G. 325 Chedekel, M. R. 376 Brink, C. V. D. M. 322 Chee, T. L. 329 Britton, R. W. 352 Cheer, C. J. 324 Brooks, C. J. W. 327,372 Chen, C. H. 328 Broschard, R. W. 42 Chen, H. H. 336 Brown, E. D. 327 Cheng, L. 42 Brown, P. 363 Chiang, C.-K. 352 Browning, H. 364 Chidester, C. G. 355 Bruderer, H. 322 Chien, M. K. 328 Brutschy, F. J. 379 Chikamatsu, H. 328,341 Bryan, R. F. 327,352 Chi Man Ho 376 Buchanan, T. G. S. C. 324 Chizhov, O. S. 349 Budzinski, J. C. 363 Chodera, A. 344 Buechi, G. 322,328 Chugunov, P. V. 328,333,364 Bui, A. M. 327 Chuiko, O. V. 362 Bukreeva, T. V. 327,350 Cicci6, J. F. 381,382,383 Burke, S. D. 338,339,360,384 Cimino, G. 329 Burlingame, A. L. 352 Clardy, J. 328 Burnstein, S. 330,332 Clarke,E. P. 329 Butcher, D. N. 322 Clemo, G. R. 153,329 Butruille et Aquilino, D. 332 Cloyd, J. C. 43 Coates, R. M. 329 Cabrera, A. 366 Cocker, W. 149,329 Cabrera, 1. 337, 383 Cocuzza, A. J. 45 Caine, D. 328 Coggon, P. 329,356 Calton, G. J. 386 Cohen, N. 355 Calzada Alan, J. G. 380,381,382,283 Cole, J. R. 347,379,384 Camp, B. J. 344,350 Connolly, J. D. 322,329 Cane, D. E. 328, 383 Conroy, H. 329 Cano, G. 383 Corbella, A. 328,329,368,369,377 Canonica, L. 328 Corbet, J. P. 292,383 Capen, R. G. 377 Corbett, R. E. 329 Carazza, F. 382 Cordell, G. A. 329,368, 386 Cardenas, G. E. 332 Corey, E. J. 156,330 Carino, M. A. 366 Corey, P. F. 44 Caristi, C. 372 Correa, J. 329 Carman, R. M. 327 Cortes, E. 238, 330, 383 Casagrande, C. 328 Cosulich, D. B. 42 Cassady, J. M. 352,353 Court, W. E. 321 Castille, A. 328 Cowherd, C. M. 353,354 Caughlan, C. N. 322,328,333,377 Cox, M. R. 352 Cavallito, C. J. 328 Cox, P. J. 327,330,362 Cave, A. 327 Crabbe,P.330,383 Cekan,Z.323,328,364 Crabtree, J. H. 324 Cervera, M. L. 329 Cradwick, P. D. 327, 330, 353 Cetina, R. 328 Cragg, G. M.332, 363 Chan, Y. M. 333,383 Craven, B. M. 330 Chao, O. 328 Crawford, H. 341 Chapman, O. L. 328 Crooke, S. T. 18,43 Chatani, J. 348 Cross, A. D. 367 394 Author Index

Crout, D. H. G. 335 Dollahite, 1. W. 379 Culvenor, C. C. 1. 330 Dominguez, B. 336, 337 Currie, M. 330 Dominguez, X. A. 332,361,365,380,383 Cutting, 1. 44 Dorfman, L. 354 Czerson, H. 325,326,330 Dorman, D. 340 Doskotch, R. W. 50, 108, 114,332,333 Daloze, D. 330 Douglas, 1. L. 333 Damirov, 1. A. 322 Draffan, G. H. 327 Daniewski, W. M. 323,325, 330, 331 Dreele, R. B. von 332, 333, 386 Danishefsky, S. 31,44,331,383 Dreiding, A. S. 354 Dann, M. 41 Drozd, B. 325, 329, 332, 333, 338, 344, 358, Das, B. C. 376 368,369,386 Das, K. G. 369 Dryanovska, N. L. 386 Da Silva, A. 1. R. 335 Duchamp, D. 1. 355 Datta, S. N. 372 Ducombs, G. 323 Dauben, W. G. 331 Dudka, V. V. 377 Dauter, Z. 325,351 Duffield, A. M. 322 David, R. E. 378 Dugan, J. 1. 333 Davies, V. H. 352 Dullforce, T. A. 333 Davis, M. 1. 383 Dupont, W. 44 Davis, R. E. 362 Du Preez, 1. C. 331 De Bernardi, M. 331,377,383 Durham, L. J. 322 De Clerq, P. 331 Dutta, L. N. 382 De Groote, R. 341,345,384 Dutta, P. C. 325 De Kock, W. T. 322,331 Del Amo, S. 383 De la Rosa, A. D. 337 East, D. S. R. 333 Delgado, G. 387 Easterfield, T. H. 333 De Lourdes Moreira Fernandes, M. 331 Eble, T. E. 41 De Mayo, P. 149,323,333,355,373 Edgar, M. T. 383 Dennis, N. 343,380 Edward, 1. T. 383 Deodhar, K. D. 381 Edwards, O. E. 333 De Oliveira, A. B. 331 Eggert, 1. H. 43 De Oliveira, G. G. 331,382 Eguchi, S. 369,378 Dermanovic, M. 331 Ehinann, L. 367 Deshpande, N. R. 385 Ehlers, D. 326 Desiderio, D. M. 363 Einck, 1. J. 333 De Silva, G. A. 382 Ekwuribe, N. M. 43 De Silva, L. B. 331 EI-Antably, M. S. 368 Despande, N. R. 369 EI-Feraly, F. S. 50, 114,332,333,383 De Stefano, S. 329 El-Hawary, S. S. 385 De Titta, G. T. 384 Ellestad, G. A. 335 Deuel, P. G. 331,335,375 Elliot, R. H. 386 Dev, S. 387 Ellison, R. H. 355 De Villiers, 1. P. 331 Emerson, M. T. 322,328,333, 377 Devon, T. K. 331 Engel, O. 375 Diaz, E. 339,348,362,365,366,368.386,387 Enomoto, Y. 378 Di Feo, D. R. 334,369 Enriquez, R. 339 Dillon, M. O. 365 Epstein, W. 365 Djerassi, C. 330, 332 Estevez Reyes, R. 337 Doehner, R. 44 Etheredge, S. 1. 331 Dolejs, L. 332, 367, 372 Evans, D. A. 333 Author Index 395

Evstratova, R. 1. 333,334,362,363,367,371, Ganter, C. 340 381 Garcia, M. 335, 355, 364 Garcia, S. 383 Fairchild, E. H. 332, 333, 334 Garcia Blanco, S. 385 Fajardo, M. 324, 336 Garcia Marrero, B. 327,337,338,384 Farkas, L. 334,341 Garcia Tello, P. 355 Farnsworth, N. R. 329,368, 386 Gariboldi, P. 328,329,368, 369, 377 Fayos, J. 337, 383, 385 Garlaschelli, L. 377 Feldstein, J. 370 Gasanova, R. Y. 382 Feng-Yung, Fu 335 Gast, C. M. 341 Ferenczy, L. 376 Gattuso, M. 372 Fermin, C. M. 355 Gaudemer, A. 376 Fernandez, 1. 365 Gawell, L. 335 Ferrari, G. 328,329 Gehret, 1. C. E. 44 Ferreira, Z. S. 387 Geissman, T. A. 53, 109, 198,221, 290, 325, Fiedler, L. 326 331,335,336,339,343,346,353,354,356, Filho, D. D. S. 377 362,368,372,376,377,378,379,380 Finer, J. 328 Gensch, K. H. 367 Fischer, H. D. 47 Georget, P. 330 Fischer, N. H. 47, 293, 325, 330, 334, 361, Geraghty, M. B. 363 363,369,370,378,380,385,386,387 Germeraao, P. 44 Flores, H. 367 Gharbo, S. A. 349 Forostyan, F. N. 360 Ghosh Dastidar, P. P. 322 Forostjan, J. N. 369 Giacobbe, T. J. 352 Fortier, S. 384 Gibaja, S. 341 Fost, D. L. 43 Gilbert, B. 335,375,377 Foussereau,l. 323,351 Gilham, P. T. 323 Fraga, B. M. 383 Gill, St. 364 Franck, R. W. 1,44,45 Gilman, S. 339, 384 Franco, O. R. 383 Gilmore, C. J. 327,352 Frazer, R. R. 334 Gindin, V. A. 327,350 Froborg, J. 383 Gitany, R. 322,336 Frohlich, A. 335 Glotter, E. 349 Fronza, G. 331,377,383 Gnecco, S. 336 Fuehrer, H. 338 Go, K. T. 348, 349 Fuhrer, H. 348 Gombatz, K. 383 Fujita, T. 352, 353 Gomez-Pompa, A. 383 Fujimoto, Y. 41, 156,335,384 Gonzalez, A. G. 324,327,383,384 Fukuchi, G. 359 Gonzalez, G. 366 Fukui, T. 335, 348 Gonzalez Diddi, M. 339 Fukumoto, K. 43,44,45 Gonzalez Gonzalez, A. 151, 194, 290, 292, Fukuyama, T. 45 336,337,338 Fulmor, W. 42 Goodlet, V. W. 336 Funakoshi, K. 377 Gopalakrishna, E. M. 338 Fung, St. 323 Gorin, G. 353 Furukawa, H. 335, 353, 356, 357, 383 Goryaev, M. 1. 338 Furusaki, A. 349,368 Goto, T. 384 Gottlieb, O. R. 331,387 Govindachari, T. R. 338, 348 Gabe, E. 1. 335 Govindan, S. V. 291,381, 384 Gacs-Baitz, E. 382 Grabarczyk, H. 333, 338, 344, 368 Galindo, A. 337, 383, 384 Graf, H. 369 396 Author Index

Granelli, 1. 338 Hayashi, N. 340 Greene, A. E. 338, 383 Hayashi, S. 340 Grenz, M. 326, 327. 382 Hayes, W. K. 331 Grieb, R. 354 Heathcock, C. H. 340 Grieco, P. A. 111, 151.338.339.360,384, Heckel, E. 340 386 Heinz, D. E. 375,381 Grisebach, H. 329, 363 Hemingway, J. C. 353 Griffin, S. 336 Hemingway, R. J. 352,353 Griffin, T. S. 335. 339 Hempel, A. 325,351 Gubanov, 1. A. 368 Hendrickson, J. B. 50,153,340 Giiren, K. C. 339 Herald, C. L. 333, 363, 386 Guerrero, C. 339,361.362,365.366,386,387 Herald, D. L. 363 Guerrero, J. 339 Hernandez, M. G. 383 Guerriero, A. 329 Hernandez, R. 340 Guevara, J. 366 Herout, V. 323,324,328,332,333,340,344, Gust, D. 363 345,350,351,360.361,363,365,368.369, Gutierrez, M. 332 372,373,378 Guy, M. H. P. 327, 339 Herr, R. R. 41 Herran, J. 332 Habaguchi, K. 359 Herrera Velazquez, J. 337 Habib, A. A. M. 339 Herrmann, H. D. 379 Hadinec, 1. 372 Herz, W. 48, 52, 53, 87, 96, 100, 221, 238, Haegele, K. D. 334 242,288,293,321,322.328.329.330.333. Hagaman, E. W. 331 334,341,342,344,347,348,363.366,367, Hahn, E. A. 375 368,373,377.380,382,384 Hall, A. L. 341.343 Hewson, A. T. 339 Hall, 1. H. 339, 353, 384. 385 Heywood, V. 341.344 Halsall, T. G. 324 Hifnawy, M. S. 385 Hamada, F. 351 Highet, R. J. 377 Hamilton, J. A. 339 Higo, A. 344.366,380 Hammam, Z. 344 Hikino, H. 344 Hammond, G. S. 328 Hikino, Y. 344 Hance, P. D. 331 Hilal, S. H. 385 Harada, Y. 41 Hill, D. W. 344 Haran, B. 370 Himmelreich, J. 372 Harayama, T. 383 Hiraga, N. 351 Harborne, J. B. 340,341 Hirai, H. 361 Hardy, A. D. 353 Hirama, M. 383 Harley-Mason, J. 339 Hirata, T. 44 Harmatha, J. 288,340,387 Hirata, Y. 368,379,380 Harris, D. L. 354 Hiremath, S. V. 355,385 Harrison, D. A. 348 Hirose, Y. 358, 359 Hart, N. K. 324 Hirotsu, K. 387 Harukawa, T. 321 Hitt, J. C. 378 Haruna, M. 353, 354 Hladon, B. 325, 344, 368 Hasenhuettl, G. 328 Ho, C. M. 344, 358 Hata, T. 1,41.42,44 Ho, Y.-K. 45 Hausen, B. M. 340,369 Hochmannova, J. 344,345 Hausmann, W. K. 41 Hodges, R. 345 Haworth, R. D. 329 Hiigenauer, G. 342 Hayashi, K. 340 Hoeneisen, M. 338 Hayashi, M. 349, 359 Hiirhammer, L. 340,341 Author Index 397

Hoffmann, 1. J. 384 Ivanenko, O. F. 360 Hoffmann, R. 45 Ivie, G. W. 347,379 Holly, S. 376 Iwai,1. 377 Holub, M. 325, 329, 333, 341, 344, 345, 363, Iyer, V. N. 14,42 368,369,372,377,384 Holzer, K. 345 Jahnke, H. K. 41 Honwad, V. K. 345 Jain, T. C. 347 Hope, H. 375 Jakupovie, J. 326.382 Horak, M. 332,351 Jamieson,' A. T. 347 Horeau, A. 98, 345 Jamieson, G. R. 347 Horibe, 1. 357, 374, 376 Jankowski, K. 384 Hornemann, U. 12,43,45 Janot, M. M. 327 Hortmann, A. G. 156,330 Jarchow, O. 340,369 Hoshi, T. 41 Jayaraman, P. 342,343 Hsiung, H. 43 Jeffrey, C. 382 Hsu, H. Y. 353 Jeger, O. 154,322 Huang, C. 332 Jeremie, D. 347,372 Huang, E. S. 353,354 Jetzer, A. 340 Huang, H. C. 353,354,357 Jimenez, H. 366 Huang, P. K. C. 364 Jimenez, L. 366 Huber, C. P. 325, 329, 346 Jimenez, M. 365.367,386, 387 Hudson, C. S. 346 Jimenez, S. J. 332 Hufford, C. D. 332 Jizba, J. 347,361,385 Johnson, A. E. 347 Iavarone, C. 358 Johnson, D. 43 Ibuka, T. 354, 357, 385 Johnson, J. H. 347 Iehimura, H. 388 Johnston, L. D. 363 Iehita, J. 385 Jokie, A. 347, 372 Ihara, M. 43. 44, 45 Jolad, S. D. 347,384 Iida, T. 349 Jommi, G. 328,329,347,368,369,377 Iio, H. 384 Jones, S. B. 355 Iitaka, Y. 346 Jones, S. B. Jr. 321,325,387 Imagawa, T. 359 Joseph-Nathan, P. 347, 348, 365, 366, 385 Imai, J. 351 Joshi, B. S. 338,348,349 Imakura, Y. 354,384 Judd, G. F. 363 Imawaki, T. 348 Juneau, G. P. 369 Inayama, S. 322,342,344,346,370,380,384 Jungk, S. 369 Ingham, C. F. 346 Inubushi, Y. 346 Iriarte, A. 339 Kabanov, V. S. 351 Iriuehijima, S. 346 Kabuto, C. 348 Irwin, M. A. 335, 336, 346, 380 Kadival, M. V. 348 Ishii, H. 346 Kagan, H. B. 98, 334, 342, 345. 348, 355 Ishikawa, K. 321, 335, 346 Kagan, J. 348,367 Ishikawa, M. 348,374 Kalabin, G. A. 350 Ishizaki, Y. 346,347,375 Kallen, J. 348 Isobe, M. 384 Kaloshina, N. A. 360 Ito, K. 383 Kalyanaraman, P. S. 342, 343, 344 Ito, S. 323 Kamada, H. 41 Ito, T. 384 Kamat, P. L. 382 ltoh, T. 44 Kamat, V. N. 338,348 Itoigawa, M. 383 Kametani, T. 23, 34,43, 44, 45 398 Author Index

Kamiya, K. 360 Kieczykowski, G. R. 385 Kamnev, M. I. 349 Kiesel, R. J. 354 Kanamori, K. 41 Kigana, Y. 44 Kanazawa, R. 359 Kim, H. L. 344, 350, 363 Kaneko, H. 348 Kim, S. H. 353,357 Kannan. R. 347 Kimura, T. 354 Kanno, S. 350 King, R. M. 326 Kao, J. P. Y. 386 King, T. J. 350 Karawya, M. S. 385 Kinoshita, K. 350 Karim, A. 352,353 Kinoshita, S. 16,42 Karimian, K. 334 Kirby, G. W. 329,363 Kariyone, T. 348 Kirchner, F. K. 328 Karlsson, B. 348,385 Kirsch, E. J. 43 Kartha, G. 348, 349 Kirtany, J. K. 386 Karube, A. 349, 355, 356 Kir'yalov, N. P. 327, 350 Karwe, M. V. 385 Kiseleva, E. Y. 333, 350, 368 Kasai, T. 359 Kishi, Y. 37, 38, 42, 45 Kashman, Y. 349 Kishida, Y. 342,344 Kasymov. S. Z. 321.322,323,349,358,375, Kisiel, W. 350, 375 380,381,387,388 Kitagawa, I. 350 Katarao, E. 346 Kitahara, G. 331 Katayama, C. 349 Kitahara, Y. 321,348,349,350,359,371,373, Kato, E. 41 380 Kato, T. 321,349,350,371,373,380 Klaska, K. H. 340,369 Katsumura, S. 359 Klyne, W. 351 Kawaguchi, Y. 359 Knight, D. W. 351 Kawai, M. 359 Knoche, H. 351 Kawai, T. 384 Knoll, K. H. 326 Kawamata, T. 346,380, 384 Knox, J. R. 353 Kawano, N. 361 Kobayashi, M. 359 Kawatani, T. 349 Koch, W. T. 353 Kechatova, N. A. 349 Kocor, M. 325,330,331 Keeley, D. E. 45 Komatsu, K. 43 Keely, S. L. Jr. 332 Komissarenko, N. F. 349 Kehrer, 1. P. 43 Kondo, Y. 351 Kelkar, G. R. 324,348.352,355,364,369,385 Konik, A. 325 Kelly, T. R. 340 Konitz, A. 351 Kelsey, 1. E. 59, 333, 352, 353 Konovalova, O. A. 350, 351, 360, 367, 368, Kelsey, R. G. 325,349,371 375,381,388 Kempton, R. J. 44 Koreeda, M. 385 Kennard, O. 339 Korp, J. D. 378 Kepler, J. A. 349 Korshalla, J. D. 43 Kerimov, S. Sh. 349 Korte, F. 48,351 Keung, E. C. H. 322 Korte, I. 351 Khafagi, S. M. 349 Kosugi, H. 351 Khalmatov, K. K. 375 Kosugi, Y. 44 Khanna, S. N. 371 Kotva, K. 361 Kholyupak, 1. O. 362 Kovacs, O. 351,376 Khvorost, P. P. 349 Koyama, H. 346,351 Kiba1cic, P. N. 367 Kozuka, M. 352, 353, 354, 357 Kibal'chich, P. N. 368 L. J. 322 Kidokoro, S. 379 Krepinsky, J. 328 Author Index 399

Kretchmer, R. A. 352 Lichtenberg, D. 370, 382 Krishnaswami, N. R. 352 Lin, H. N. 334 Krol, J. 331 Lindauer, R. F. 379 Krull, 1. S. 352 Linde, H. H. A. 354 Kruse, L. 44 Linek, A. 372, 385 Kubota, T. 322 Link, H. 340 Kudo, S. 41 Lipscomb, W. N. 367 Kulkarni, A. B. 322 Lipsett, ~. N. 43 Kulkarni, G. H. 220,323. 348, 352, 355, 362. Lisio, A. 43 363,369,385 Liu, C. B. 361 Kulshreshtha, D. K. 362 Lonitz,~. 326,327 Kumagai, N. 383 Lopes, 1. N. C. 377 Kumar, N. 384 Lopez de Lerma, J. 385 Kupchan,S.~. 59,333.352,353,385 Lopezdorta, H. 383 Kurbanov, D. 388 Lopez Vanegas, C. 365 Kurihara, T. 321 Lovett, W. E. 367 Kuriyama, K. 376 Lown,1. W. 4,5, 14, 16, 18,42,43,44 Kurokawa, T. 353 Lucas, A. J. 336 Kusano, G. 344.351 Lucas, R. A. 354 Kushner, L. E. 321 Lugovskaya, S. A. 354 Kuwano, T. 344 Luhan, P. A. 353,356 Kuyama, S. 346 Luis, J. R. 383 Kuzovkov, A. D. 321 Luning, B. 338 Luzbetak, D. J. 384 Lakshmikantham, ~. V. 342. 343, 348, 367 Lamberton, J. A. 324 Mabry, T. J. 48,85,114,148,221,238,321, Lancaster, J. E. 42 324,325,334,335,338,341,344,348,354, Lane, 1. F. 353 355,356,357,361,362,363,364,365,366, Langenheim, J. H. 355 367,375,376,378,380,386,387,388 Lansbury, P. T. 385 ~acaira, L. A. 355 Lavie, D. 349 ~achado, L. 377 Leadbetter, G. 43 ~ackey, J. K. Jr. 45 Leander, K. 335, 338 ~acPhillamy, H. B. 354 Lechleiter, J. C. 388 ~adhusudanan, K. P. 382 Lederer, E. 372 ~aeda,~. 328 Lee, J. 344 ~aeda, S. 348, 350, 359 Lee, K. H. 335, 336, 339, 346. 352. 353, 354, ~agalhaes, ~. T. 331 356,357,384,385 ~agnusson, G. 355,383 Leeds, N. S. 353 ~ahanta, P. K. 326,382 Lefemine, D. V. 41 ~ainero, R. ~. 329 Leon, E. 366 ~ajetich, G. 339,386 Leon, S. 328 ~ajor, R. T. 359 Leonteva, L. 1. 360 ~akiyama, Y. 359 Leppard, D. C. 354 ~akoto, F. 350,349 LeQuesne, P. W. 291,364.385 ~akowska, B. 338 LeVan, N. 326,385 ~aleville, J. 351 Levery, S. B. 364.385 ~allabaev, A. 371, 381, 385, 387 Levisalles, J. E. D. 323 ~anchand, P. S. 385 Levy, J. 336 ~andell, L. 31, 35, 44 Leyter, L. 332 ~ane, B. ~. 385 L'Homme, ~. F. 354 ~anitto, P. 347 Liberalli, C. T. ~. 331 ~anresa, ~. T. 382 400 Author Index

Mansilla, H. 337,383, 384 Mears, J. A. 366 Mao, D. T. 291,388 Meck, R. 335,354, 356 Mar, E. C. 339,385 Meguro, K. 344 Marcano Fermin, C. 355 Meisels, A. 356 Marinovic, N. 338, 339 Mellerio, G. 383 Marshall, J. A. 355,385 Menachery, M. D. 385 Marshall, W. S. 42 Mercado, C. M. 43 Martelli, A. 359 Metwally, A. M. 339, 349 Martin, C. L. 344 Metz, W. 360 Martin, D. G. 355 Meyer, W. E. 42 Martin, E. B. 377 Mhaskar, V. V. 387 Martin, J. L. 382 Miki, T. 321 Martin, S. S. 355 Miljkovic, D. 372 Martin-Smith, M. 355 Miller, H. E. 348, 355, 357, 380 Martinez, M. 339 Miller, R. B. 357 Martinez, R. 362, 386 Miller, R. W. 356 Martinez-Ripoll, M. 385 Mills, R. W. 357 Marumo, H. 41 Minale, L. 329 Maruyama, M. 352,353,355,359 Minato, H. 346,357, 374, 375 Marx, J. N. 355,378 Mincione, E. 358 Masako, U. 350 Miranda, R. 330 Masamune, T. 388 Miranda Plata, S. 339 Masayoshi, A. 385 Mirrington, R. N. 342,367 Maslova, G. A. 368 Mitchell, J. C. 365,388 Masojidkova, M. 384 Mitchell, R. D. 358 Mason, J. E. 349 Mitra, R. B. 342 Massanet, G. M. 336, 337, 383, 384 Mitsuhashi, H. 340 Massiot, G. 358 Miyakado, M. 324 Massy-Westropp, R. A. 346,355 Miyano, K. 45, 358 Masuchi, Y. 385 Miyazaki, M. 342, 344 Mathur, S. B. 355 Miyoshi, Y. 359 Matsubara, 1. 42 Mizsak, S. 355 Matsueda, S. 238, 336, 354, 356, 377, 385 Mizuno-Tsukuda, Y. 351 Matsui, M. 42, 43, 44 Mladenovic, S. 331 Matsumae, A. 41,42 Mnatsakanyan, V. A. 358 Matsumoto, T. 358 Moiseeva, G. P. 358 Matsuura, T. 340, 356 Momose, T. 322 Maurer, G. 341 Mompon, B. 356, 358, 376 Mazur, Y. 356 Monder, C. 377 McCloskey, J. E. 347 Money, T. 357, 358 McClure, R. J. 356 Monnikendam, P. 41 McEwen, R. S. 322,336,373 Monti, S. A. 362, 378 McFarland, J. W. 331 Moore, H. W. 42, 44 McGaughey, S. M. 355 Mootoo, B. S. 333 McKean, M. L. 360 Mora-Arellano, V. 355 McKee, M. 323 Morales, A. 337 McMillan, C. 356 Moreira Bacha, C. T. 382 McMorris, T. C. 359 Morgan, A. R. 43 McMurry, T. B. H. 149, 323, 329, 333, 335, Mori, H. 359 346,356,364 Mori, M. 356 McPhail, A. T. 93, 339, 349, 352, 353, 354, Moriguchi, 1. 43 356,357,383 Morikawa, K. 358 Author Index 401

Morimoto, H. 358 Nel, W. 322 Moriyama, Y. 346,358 Nes, W. R. 360 Morris, M. S. 349, 371 Neshta, 1. D. 360 Morton, G. O. 42 Newcombe, F. 321 Moss, G. P. 59,323,358,365 Niknejad, A. 387 Motl, O. 345,358,384 Nikonov, G. K. 350,360 Mowat, J. H. 42 Nikonova, L. P. 360 Mozdzanowska, A. 338 Nisbet, A. 329 Mukhametzhanov, M. N. 358.359. 368, 385 Nisbet, M. 333 Muller, J. C. 323, 338, 363 Nishida, T. 388 Munakata, K. 378 Nishino, T. 350 Munk, M. E. 42 Nishitani, K. 380,388 Murai, A. 386 Nishizawa, M. 111,338,339,360 Murakami, A. 388 Nitta, 1. 349,360,368 Murakami, T. 375 Nogi, N. 359 Murani, R. 382 Nogradi, M. 334 Murari, R. 343, 377. 384 Noll, K. 42 Murayama, S. 336 Nomura, S. 42 Murkherjee, R. 336 Nordman, C. E. 335 Norman, J. O. 347 Nachbar, R. B. 328. 383 Nosaka, S. 357 Nadgouda, S. A. 386 Novak, C. 372,385 Naemura, K. 359 Novikov, V,J. 360,369 Nagaki, M. 385 Novotny, L. 340,345,347,350,360,361.385 Nagakura, E. 379 Noyes, W. A. 328 Nagakura, 1. 359 Nozoe, S. 358 Nair, M. S. R. 359 Nunez. C. S. 43 Naito, M. 359 Naito, S. 348 Ode, R. H. 332 Naidenova, E. 384,385,386 Oksiiz, S. 339, 377 Nakadaira, Y. 359 Ogawa, Y. 374 Nakamura, H. 340, 359 Ogura, H. 361 Nakamura, S. 359, 379 Ogura, K. 356 Nakanishi, K. 353, 359 Ogura, M. 386 Nakanishi, M. 359 Oguri, T. 339, 384 Nakano, K. 42 Ohashi, A. 361 Nakatani, N. 362 Ohfune, Y. 339,358,386 Nakatsubo, F. 45 Ohkura, T. 346, 384 Nakazaki, M. 328, 359 Ohno, N. 361,386 Nanao, H. 359 Ohsawa, T. 45, 386 Nano, G. M. 359 Ohta, T. 359 Narain, N. K. 386 Ohta, Y. 361 Narayanan, C. R. 323, 359 Ohtsuru, M. 374,376 Naruto, S. 348 Okamoto, M. 354 Nash, R. D. 357 Okamoto, T. 361 Natsume, M. 361 Okigawa, M. 361 Natu, A. A. 326, 382 Okuda, T. 361 Naya, K. 349, 359 Ok una, T. 380 Nazarenko, M. V. 324, 360 Okuyama, M. 44 Nazarians, L. 367, 387 o lishevets, L. 1. 377 Negron, G. 360 Oliveros, M. 387 Neidle, S. 59,335,360,365 Olivier, E. J. 47,361

Fortschritte d. Chern. org. Naturst. 38 26 402 Author Index

Olmos. F. 367 Pidacks, C. 42 Olsen, 1. S. 388 Piers, E. 363 Olson, J. 43 Pieth, P. 367 Olszewski, J. 344 Pi lotti, A-M. 348,385 Omar, A A. 349 Pimenov, M. O. 321,327,351,382 Omoto, T. 348 Pinder, A R. 48, 257, 363 Omura, S. 355 Pinhey, J. T. 148,323,363 Onaka, T. 361 Piotrowski, J. 333 Onan, K. D. 93,352,354,356,357,361,383 Pitts, J. N. 328 Ono, M. 386 Pivnenko, O. P. 362 Onoda, R. 321 Plambeck, J. A. 42 Orishchenko, N. D. 367 Plekhanova, N. V. 354 Orovbaev, K. Y. 354 Plettman, S. O. 356 Ortega, A 339,361,362,364,365,366,367, Poletto, J. F. 43 368,386,387 Politz, S. M. 334 Oshio, H. 358, 360 Polyakov, P. P. 338 Otaki, Y. 356 Popa, D. P. 345,360, 369 Ourisson, O. 323,338,351,363 Poplawski, J. 342,345,363 Overton, K. H. 322, 349, 357 Popova, A L 363 Porter, T. H. 354, 363, 380 Pachler, K. O. R. 322,331 Post, M. L. 325 Padolina, W. O. 321,355, 362, 375, 378 Potier, J. 327 Pakaln, D. A 382,350,351,358,359,362,364 Potter, J. L. 363 Paknikar, S. K. 364,372,386 Power, F. B. 364 Pakrashi, S. C. 322 Poyser, J. P. 336 Pal, R. 362 Prabhakar, S. 363 Palafox, A. 361 Pregosin, P. S. 358,364 Parello, J. 327 Primukhamedov, L 375 Parker, B. A. 362 Prochazka, V. 323,328,364 Parker, W. 362 Quick, A. 364 Pascard, C. 362 Quijano, L. 364, 365, 386 Pascual, C. 382 Pashchenko, M. M. 362 Rabi, J. A 146, 194,335,355,364,377 Patel, A R. 359 Rabindran, K. 342, 343 Pathak, S. P. 362, 363 Radics, L. 382 Patra, A 374 Raffauf, R. F. 364, 385 Patrick, 1. B. 42 Ragab, M. S. 354 Pattenden, O. 324,351 Raghavan, R. 364 Payne, W. W. 336,344,357 Rajappa, S. 342 Pelizzoni, F. 347 Rakhmankulov. V. 371,381,385 Pelletier, S. W. 363 Ramage, R. 362 Perez, A L. 367 Ramakrishnan, O. 342 Perez, F. M. 332 Randall, E. W. 358,364 Pena, V. 383 Rane, D. F. 356 Perez, J. 337 Rangaswami, R. 370 Perold, O. W. 351,363 Ranieri, R. L. 43,386 Perry, D. L. 334, 363, 378 Rao, A. S. 325,345,348,364,371 Petrova, E. F. 368 Rao, O. M. 42 Pettersen, R. C. 339, 363 Rao, S. P. V. 388 Pettit, O. R. 332, 333, 363, 386 Rastogi, R. C. 325, 326 Piantadosi, C. 335, 353, 354, 356, 357 Rastogi, R. P. 362 Picman, A K. 386 Raszeja, W. 364 Author Index 403

Raulais, D. 341,342,343,344 Ruecker, G. 290,367,387 Ravindranath, K. R. 364 Ruesch, H. 367, 380 Rebek, J. Jr. 44 Runeckles, V. C. 335,341,366 Reichstein, T. 367 Rushing, D. D. 347 Reid, E. H. 347 Rustaiyan, A. 367, 387 Reinecke, M. G. 378 Ruzicka, L. 50, 367 Remers, W. A. 23,42,43,44, Rybalko, K. S. 328,333,334,349,350,351, Renold, W. 348, 354, 355, 364, 380 358,359,360,362,363,367,368,371,375, Resendiz, J. 387 381,388 Restivo, R. J. 352 Rzazade, R. Y. 333 Revazova, L. V. 358, 364 Rey, M. 354 Saber, A. H. 368 Reynolds, G. D. 346,355 Sadgopal, A. P. 364 Rindone, B. 329 Safir, D. 379 Rios, T. 364,365,366,386 Saidkhodzhaev, A. I. 350, 387 Ro, K. 321 Saitbaeva, I. M. 368 Roberts, E. C. 44 Saitoh, T. 336, 368 Roberts,1. C. 350 Sakabe, N. 368 Roberts, J. S. 330,362,364 Sakaguchi, R. 379 Robinson, D. L. 364 Salazar, I. 339 Robinson, H. 326 Saleh, A. A. 368 Robinson,1. R. 325,333 Salmon, M. 368 Rodrigues, A. A. S. 364 Samek, Z. 87, 148, 195, 288, 324, 325, 329, Rodriguez, E. 364,365,366,380,384,386,388 333,340,341,345,347,361,363,368,369, Rodriguez, L. F. 337 373,378,380,384,385,387 Rodriguez, M. 322 Sammes, P. G. 336 Rodriguez, R. M. 337 Sanches Parareda, I. 369 Rodriguez-Hahn, L. 360,365,367,386,387 Sanches Parareda, J. 369 Rodriguez Rincones, M. 337 Sanches-Viesca, F. 369 Rodriguezluis, F. 383 Sancin, P. 359 Rogers, D. 59, 335, 360, 364, 365, 377 Sandoval, A. 340 Rohde, W. A. 342, 343 Sanno, Y. 358 Rojas Garciduenas, M. 365 Sano, Y. 41 Romanuk, M. 365, 374 Santana, M. 339 Romero, M. C. 383 Santhanam, P. S. 343 Romo, J. 48, 221, 240, 328, 330, 339, 340, Sarg, T. M. 349 343,348,360,361,362,364,365,366,367, Sarti, S. J. 377 369,383,387 Sasada, Y. 361 Romo de Vivar, A. 48, 221, 328, 339, 342, Sasaki, S. 356 343,361,362,364,365,366,367,38~387 Sasaki, T. 369, 387 Roque, N. F. 387 Sata, Y. 356 Rosado, A. 322 Sathe, R. N. 82,369 Rosanske, R. C. 377 Satoda, I. 369 Rosenthal, D. 328 Sawada, M. 359 Ross, J. M. 367 Sazonova, R. N. 338 Ross, W. F. 331 Schaffner, K. 369 Rossmann, M. G. 367 Schenck, G. 369 Roth, R. H. 44 Schikarski, M. 290, 387 Rovinski, S. 354 Schlesinger, R. H. 385 Rowe, L. D. 347, 350 Schmalle, H. W. 340,369 Roy, S. K. 342, 343 Schmid, 1. J. 342,343 Ruban, G. 367 Schmidt-Loeffler, P. 369

26* 404 Author Index

Schneider, G. 369 Sim, G. A. 59, 323, 327, 329, 330, 333, 339, Schnoes, H. K. 352 349,352,353,356,357,362,371,378 Schoneweiss, S. 326 Simonovic, D. M. 371 Schreiber, VV. 369 Simonsen, 1. 149,371 Schuda, P. F. 331,383 Simpson, R. F. 346, 354 Schulz, K. H. 340, 369 Sims, C. L. 333 Schwarz, 1. S. P. 331 Sims, D. 354,384 Scolastico, C. 329,347 Sims, 1. 1. 371 Scott, A. 1. 331 Singh, A. N. 387 Seaman, F. C. 334,369,370,387 Singh, R. 382 Sedmera, P. 345 Singh, S. P. 348 Segal, R. 370, 371. 382 Sinyukhin, A. M. 334 Sekita, T. 370 Siqueira, N. C. S. 382 Semmelhack, M. F. 387 Siskovic, E. 345 Semmler, F. VV. 370 Sisti, M. 329 Sengupta, P. 332 Siuta, G. 1. 44 Serelis, A. K. 385 Sleptsova, L. V. 324 Serkerov, S. V. 350,370,387 Siomp, G. 355 Seshadri, T. R. 352 Smalia, H. 367 Seshadri, V. 370 Smillie, R. D. 363 Seto, H. 387 Smirnov, P. N. 349 Shafizadeh,F.325,349,371 Smith, D. H. 352 Shah, G. D. 42 Smith, R. G. 354 Shah, L. G. 42 Smith, S. 1. 355 Shaligram, A. M. 325,382 Smolenski, C. 371 Sham'yanov, 1. D. 371,387 Snatzke, G. 371, 372, 373 Shannon, 1. S. 345 Sneath, T. C. 324 Sharma, R. P. 96, 100, 342, 343, 347, 382 Sneden, A. T. 352,385 Sheichenko, V. 1. 328, 333, 334, 349, 350, Soderholm, A. C. 385 351,358,359,367,368,370,371,375,382 Solagdenhauffen. F. 340 Shibata, F. 355 Soine, T. O. 321 Shibata, H. 387 Sokoloff, S. 370,371,382 Shibuya, H. 350 Solujic, S. 372 Shibuya, S. 353 Soria, E. L. 371 Shima, T. 41 Sorm,F.48,324,328,332,333,340,344,345, Shimizu, G. 41 350,351,360,361,365,369,371,372,373, Shimizu, M. 42, 361 378 Shimizu, S. 387 Soucek, M. 332,372 Shimizu, T. 335,384 Southwick, L. 321 Shingu, T. 335,357 Spitzer, 1. C. 372 Shinoda, N. 359 Spotswood, T. M. 355 Shirahata, K. 321,349,371 Srinivasan, A. 341,343 Shreter, A. 1. 321, 328, 358, 367, 375 Srivastava. S. C. 45,372 Shreter, A. M. 328 Stagno d'Alcontres, G. 372 Shretev, A. 1. 350 Stahl, E. 372 Shuhuma, 1. K. 377 Starnes, C. O. 339 Siade, G. 365 Starratt, A. N. 373 Sidhaye, A. R. 338 Steele, 1. VV. 372 Sidyakin, G. P. 321,322,323,349,358,368, Steelink, C. 366,372 371,375,380,381,385,387,388 Stefanovic, M. 331,347,372 Silberman, L. 44 Stenlake, 1. B. 355,372 Silva, M. 336,338, 371 Stephens, R. L. 387 Author Index 405

Sternhell, S. 148,363,372 Takeno, H. 350 Stevens, C. L. 42 Takeshita, H. 359 Stevens, C. S. 344 Takeuchi, S. 374 Stevenson, D. S. 372 Takeuchi, T. 349 Stewart, T. 336 Talapatra, B. 374 Stockel, J. 337 Talapatra, S. K. 374 Stocklin, W. 372,378 Talekar, R. R. 333,356 Stoessl, A. 325 Talipova, M. A. 375 Stothers, J. B. 325,373 Tamas, J. 382 St. Pyrek, J. 372 Tamura, S. 346,361 Strike, D. P. 378 Tamura, Y. 376 Stuessy, T. F. 350,370 Tanabe, K. 377 Subramaniam, P, S. 341,343 Tanahashi, Y. 346, 347, 375 Suchy, M. 340,372, 373 Tanaka, N. 375 Sudarsanam, V. 334,341,343,344 Tanemura, M. 350, 373 Sugawara, R. 41 Tarasov, V. A. 375, 387 Sumi, M. 321,373 Tarbell, D. S. 367 Sumi, Y. 344 Tatee, T. 375 Sundararaman, P. 373 Tatsuno, T. 335, 384 Sutherland, J. K. 327,373 Taylor, D. 361 Suwita, A. 326,382 Teraoka, M. 374 Suwita, An. 326, 382 Taylor, I. F. Jr. 325, 375 Suzuki, A. 361 Taylor, K. G. 42 Suzuki, M. 379 Taylor, W. G. 42. 43 Suzuki, T. 349,350,373 Tellez, J. 339 Swain, T. 340 Tello, H. 366 Sykora, V. 374 Thyagarayan, G. 382 Synackova, M. 340 Terent'ev, P. B. 381,388 Szwemin, S. 325 Tether, L. R. 348 Szybalski, W. 14,42 Tettweiler, K. 375 Thaller, V. 324 Taboada, J. 339 Thayer, P. S. 363 Tada, H. 374,376 Theobald, D. W. 364 Tadahiro, K. 350 Thiele, K. 369 Tajima, K. 381.385 Thiessen, W. E. 375 Takabatake, A. 360 Thomas, J. W. 349 Takada, N. 348 Thomas, R. C. 44 Takada, S. 379 Thompson, D. J. 350 Takada, T. 43,44 Thompson, W. J. 352 Takagi, I. 359 Thoms, H. 375 Takahashi, K. 43, 44 Thoren, S. 331,355 Takahashi, N. 346 Thornton, I. M. S. 382 Takahashi, S. 348 Thyagarayan, G. 382 Takahashi, T. 42, 346, 347, 358, 375 Tien-Ming Shang 335 Takai, K. 359 Tillyaev, K. S. 375 Takakuwa, T. 379 Timmermann, B. N. 48, 85, 221, 238, 344, Takase, K. 322,381,385 380 Takashina, H. 359 Toga, T. 321 Takayanagi, H. 361 Tolstykh, L. P. 349, 362, 375 Takeda, K. 88, 110,374,376 Toman, J. 325,345,361 Takeda, R. 350 Tomassini, T. C. B. 375 Takemoto, T. 344,351,381.382 Tomasz, M. 15, 18,43 406 Author Index

Tomczyk, H. 375 Uzawa, J. 387 Tomesch, J. C. 387 Uzu, K. 41,42 Tomiie. Y. 360,368 Tomimori, T. 351 Van den Hende, J. H. 3,42 Tominaga, T. 380,388 Vandewalle, M. 331 Tomita, Y. 375 Vanell, L. D. 363,386 Tomoka, K. 41 Vanhaelen, M. 377 Tori, K. 90,347,374,375,376 Vanhaelen-Fastre, R. 377 Toribio, F. P. 336, 376 Van Lear, G. E. 42 Torii, S. 388 Van Tonder, G. 322 Torrance, S. J. 376,384 Vargas, C. 362 Toth, J. 376 Vasickova, S. 324,384 Toubiana, M. J. 376 Vazquez, F. 367 Toubiana, R. 344,356,358,376 Vazquez, P. 382 Towers, G. H. N. 365,377,386,388 Vedantham, T. N. C. 352 Toyota, M. 323, 382 Veech, J. A. 347 Tozyo, T. 346 Veeravalli, J. 386 Traynor, S. G. 356 Velez, A. 366 Trehan, I. R. 377 Velimorovic, S. 372 Trevino, R. 366 Venkatasubramanian, N. K. 359 Triana, J. 337 Verzar-Petri, G. 382 Trivedi, G. K. 364, 382, 386 Vichido, C. 387 Trutneva, E. A. 368 Vichnewski, W. 377 Tsai, L. 377 Vidari, G. 331,377,383 Tseng, K. F. 328 Viehoever, A. 377 Tsuda, K. 377 Viguera, J. M. 369 Tsuda, Y. 346 Villar del Fresno, A. 324 Tulinsky, A. 3, 42 Vining, L, C. 43 . Turley, R. 336 Viswanathan, N. 338,341,342,343,344 Turnbull, K. W. 377 Vita-Finzi, P. 331,377,383 Turner, B. L. 341,357 Vlasov. M. I. 349 Turner, B. P. 347 Vokac, K. 195,369,378 Tursch, B. 330 Tyler, T. W. 336 Wada, K. 378 Uchimaru, F. 361 Waddell, T. G. 336,339,354,368,372,378 Ueda, K. 344 Wagner, H. 340,341 Uemoto, M. 323 Wahlberg, I. 87,344,348 Ueno, M. 359 Wakagi, S. 41 Ueyama, M. 376 Wall, M. E. 349 Ujszaszy, K. 382 Wallhoefer, L. 369 Ukita, T. 322 Walls, E. 332 Ul-Haque, M. 322, 328, 377 Walton, E. 329 Ulubelen, A. 339, 377, 388 Wander, J. D. 334 Umeswara, I. 42 Wang, C. L. J. 339,386 Umino, N. 379 Ward.E. W.B. 325 Uneyama, K. 388 Warden. K. 348 Uomori, A. 375 Watanabe, H. 342, 344 Urbina, E. 366 Watanabe, M. 378 Urmanova, F. F. 388 Watkins, S. F. 324, 378, 379 Uskokovic, M. R. 377 Watson, K. J. 346 U synina, R. V. 377 Watson, T. J. 349 Author Index 407

Watson, W. H. 325,338,362,375,378,381, Yahashi, R. 42 387 Yamada, K. 379 Webb, J. S. 42 Yamada, Y. 41,43,44 Wedekind, E. 375 Yamakawa, K. 291,388,380 Wehrli, F. W. 325 Yamamoto, A. 379 Weinges, K. 359,378 Yamamoto, M. 42 Weiss, M. J. 23,43,44 Yamamura, S. 380 Weissbach, A. 43 Yamashita, A. 387 Welbaneida, F. 377 Yamazoe, Y. 350 Wells, R. J. 323 Yanagawa, H. 380 Wender, P. A. 388 Yanagita, M. 346.380 Wenkert, E. 331,378,387 Yazawa, T. 375 Werner, D. 352,353 Yen-Yang Chen 335 Wessels, P. L. 331 Yokohama, Y. 339 White, D. N. J. 327,333,339,378 Y onehara, H. 374.387 White, E. H. 355,378 Yoshida, N. 369 White, E. P. 345 Yoshida, T. 361 Whittle, 1. A. 323 Y oshii, E. 369 Wichmann, G. 378 Y oshikoshi, A. 378 Wiedhopf, R. M. 347, 379, 384 Yoshino, A. 361 Wiehager, A. C. 348 Yoshioka, H. 48,85,149,221,238,321.324, Wiley, R. A. 325, 334 344,354,361,362,363,364,365,366.376, Williams, E. 339 380 Williams, R. P. 42 Y oshitake, A. 380 Williams, T. H. 377 Yoshizaki, F. 351 Williams, W. D. 355, 372 Y osioka, 1. 350 Willuhn, G. 379 Y osioka, T. 344 Wilson, S. R. 291,388 Young, M. 379 Winter, R. E. K. 378, 379 Yunusov, A. 1. 380,381,388 Winters, T. E. 336, 379 Yusupov, M. 1. 381,388 Winters. T. W. 339 Witt, M. E. 379 Witters, R. W. 333 Wittgreen, G. 366 Zabel, V. 367,381,387 Witzel, D. A. 347,379 Zaitschek, D. V. 370 Wolf, C. F. 42 Zakharov, P. 1. 351,381,388 Wolo, M. T. 353 Zakharov, V. F. 371 Woods, M. C. 321,359 Zakirov, S. K. 381 Woodward, R. B. 45.153,379 Zarghami, N. 375, 381 Wooley, J. G. 323 Zavarin, E. 355 Wu, 1. B. 378 Zbinovsky, V. 41 Wu, B. S. 353 Zdero, C. 290, 326, 337, 382 Wu, W. 353 Zechmeister, L. 351,365.369,371 Wuts, P. G. M. 385 Zetina, C. 367 Zinke, A. 345 Yabuta, G. 387,388 Zoltowska, B. 331 Yagudaev, M. R. 375,381.387,388 Zvolinskii, V. P. 371 Subject Index

By

A. SIEGEL, Wien

Absinthin 178,199 Adenocarcinoma 18 Acanthamolide 68, 116 Aduncin 271,272 Acanthospermal A 68, 94, 116 Ageratina petiolaris 207 Acanthospermal B 68, 94, 116 Aguerin A 300, 315 Acanthospermum australe 116 Aguerin B 300,315 - glabratum 116 Akihalin 186, 199 - hispidum 116 ~- 2 Acetic acid 8,9,21, 100, 103, 105, 106, 150, Alantolactone 142,149,150,157 154, 155, 192, 242, 244, 259 -, dihydro- 143, 157 Acetic anhydride 28, 39, 106, 240 -, dihydro-, epoxide 257 Acetone 100, 257 -, lo:,8o:-dihydroxy- 135,157 Acetophenone 290 -, 1~-hydroxy- 142,157 Acetoxypentanal 26 -, 2o:-hydroxy- 142, 157 Achillea asplenifolia 207 -, lo:-hydroxy-8o:-(2-hydroxymethyl- - biebersteinii 158,208,311 acryloxy)- 135, 157 cartilaginea 205, 206 -,8o:-hydroxy-lo:-(2-hydroxymethyl- - collina 207 acryloxy)- 135, 157 - eriophora 206 -, iso- 142, 148, 149, 150, 157,291,292 - lanulosa 199,205,206,207 -, iso-dihydro- 143, 157 - micrantha 286 -, iso-3~-hydroxy-2o:-senecioyloxy- 142, - millefolium 117, 128, 199, 206, 207, 286, 157 315 -, neo- 143, 157,300 - monogyna 286 -,2-oxo- 142, 158 - santolina 206 Alatolide 62, 95, 116 - sibirica 207 Albicolide 62,116 - stricta 207 -, 8-(2-methylbutyryloxy)- 294, 308 - vermicularis 206 Alkhanin 299,314 Achillea lactone 286 Alkylation, bioreductive 13 Achillicin 302, 315 D-Allosamine 21 Achillin 174, 199 Altamisin 304, 318 -, acetoxy- 174, 199 Alternilin 228, 246 -, 1,10-epoxy- 175,199 D-Altrosamine 20, 21 -, 1,10-epoxy-8o:-hydroxy- 175,199 Aluminium chloride 24 -, hydroxy- 174,191,199 Aluminium hydride III Acroptilin 170, 199 Aluminium hydroxide 241 Acroptilon repens 199,208 Aluminium oxide 1, 37 Subject Index 409

Amarantacea 265 Angeiate 96 Amarilin 228, 246 Angianthus tomentosus 213 Amberboa lippii 199, 204, 205 Angustibalin 230, 246 - muricata 202,207,315 Aniline 25 Amberboin 177,199 Anisatin 280, 282 -, iso- 177, 199 -, neo- 280, 282 Amblyodin 228, 246 -, pseudo- 280, 282 Amblyodiol 229, 246 Anthemis cotula 282 Ambrosanolides 49, 223, 236 - cretica 119, 128, 129 -, biogenesis 236f - cupaniana 129 -, chemical transformations 239 - nobilis 128 -, seco-derivatives 237,244 Anthemis, lactone from 274, 282 -, structure elucidation 238 Anthemoidin 234, 247 Ambrosia acanthicarpa 117,202,248,254 Antibacterial activity 16 - ambrosioides 249,250 Antibiotic 0-253 7 - arborescens 200, 248, 249, 254 Antitumor activity 17,18, 19 - artemisiifolia 116,125,129,248,249,253, Apachin 187,212 254 Aplysia angasi 320 - camphorata 157 Aplysistatin 305, 320 - canescens 247 Apoludin 225, 247 - castanensis 116 Arabsin 139, 158 - chamissonis 117,118,119,125,132 Arbiglovin 172, 200 - chenopodiifolia 249 Arborescin 175,200,315 - confertiflora 116, 118, 128, 131, 163, 165, Arbusculin A 136, 158 248,253,254 -,4-epi- 136, 158 - cordifolia 248, 254 -, 1/3-hydroxy- 136, 158 - cumanensis 202,246,249,254,318 Arbusculin B 135, 158 - deltoidea 249, 254 -, ent- 146, 158 - dumosa 117,128,246,247,248,254 Arbusculin C 135, 158 - hispida 246, 249 Arbusculin D 139, 158 - jamaicensis 246, 249, 254 Arbusculin E 136, 158 - maritima 246, 249 Archangolide 177, 200, 292, 303 - peruviana 246, 253, 254 Arctiopicrin 62, 105, 116 - polystachya 161, 162,249 Arctium lappa 116 - psilostachya 125, 246,248,249,253,254 - minus 116 - pumila 248, 254 - nemorosum 116 - tenuifolia 254 - tomentosum 116 Ambrosiinae 236 Arctolide 184,200 Ambrosin 224, 239, 240, 246 Arctotis aspera 128,210 -, 2,3-H-2,3-epoxy- 224,246 .- grandis 200 -, mono bromide 239 - repens 128 -, neo- 225, 246 - revoluta 210,211 - tetrahydro- 225, 246 Arginine 21 Ambrosiol 225, 239, 246 Arglanin 136, 148, 158 -, 3-tosyl- 239 Aristalin 286 Aminoquinones 2 Aristolactone 75, 116 Ammonia 3, 23, 24, 29, 38 Aristolochia serpentaria 116 Anabsinthin 178, 200 Armexifolin 135, 158 Anamirta cocculus 272 Armexin diacetate 139, 158 - paniculata 272 Arnicafoliosa 212,247 Anaphalis morrisonicola 251 - longifolia 212, 251 Andrographis paniculata 283 - montana 247,251,286 410 Subject Index

Arnicolide 186 incana 164, 206 Arnico lide A 231, 247 jacutica 129,200, 209 Arnico lide B 231, 247 judaica 162 Arnicolide C 231,247 juncea 206 Arnicolide D 231,247 kemrudica 159 Arnicolide E 286 klotzchiana 199,201,205,206 Arnifolin 229,247 kurramensis 163, 164 Aromaticin 228, 247 lagocephala 199 Aromatin 230, 247 lanata 199 Arsanin 139, 158 lercheana 206 Arsantin 139, 158 leucodes 205, 206 Arsubin 138, 158 ludoviciana 160, 162, 163, 199,206,286 Artabin 64, 116 macrophylla 208 Artabsin 178, 192, 195, 196, 197, 198, 200 maritima 159, 164, 165,309 -, tetrahydro- 192 mexicana 117,132,158,159,160,164,201, Arteannuin B 275,281,282 203 Artecalin 136, 158 meyriana 164 Artecanin 172, 200 mogoltavica 164 Artefransin 171, 200 monogyna 163, 164, 286 Arteglasin A 166, 198, 200 nova 128,200,202 Arteglasin B 169,200 princeps 165 Artemexifolin 136, 159 ramosa 161, 164 Artemin 138,140,150,151, 159 rothrockii 163 Artemisia absinthium 116, 129, 158, 159, 195, rupicola 130 199, 200 rutafolia 286 anethifolia 129 salina 116, 165, 200 annua 282,283 santolina 158, 159 arborescens 200 schrenkiana 164, 165 arbuscula 117,125,130,158 sibirica 206 ashurbajevii 124, 161 siversiana 199, 200, 208, 209 - austriaca 206 sp. 165 balchanorum 117, 119, 120, 159 - spicata 163 - bigelovii 200 - stelleriana 164 - caerulescens 164 - sublessingiana 158 - californica 158 - szovitsiana 164 - cana 116, 129,200,201,205,206,209 taurica 159, 165 canariensis 165 tenuisecta 159, 164 caruthii 205, 207 tilesii 200,205,206 caucasica 204, 206, 286 transiliensis 164 chasarica 164, 165 tridentata 116, 121, 125, 129, 130, 131, Gina 159,165,221,287 158, 160, 163, 164, 205, 206, 207 compacta 165 tripartita 116,128,129,130,159,163,199, douglasiana 158, 160, 200 201,202,205,206,208 - feddei 314,317 verlotorum 132,133,165 - jinita 161,164 vulgaris 165 - fragrans 160, 164,314 Artemisiifolin 65, 96, 97, 99, 102, 103, 116 - franserioides 200 -, C-15-acetyl- 65, 116 - granatensis 161, 165 -, cis,cis-15-

Artevasin 76, 116 Bakkenolide E 261,264 Artilesin 200 Bakkenolides 48,49,52, 257f Artilesin B 174 Baichanin 134, 159 Ashurbin 143, 159 Balchanolide 64, 117 Asperilin 142, 149, 159 -, acetate 64, 117 Aster tataricus 262 -, hydroxy- 64, 117 Athanasia coronopifolia 205 -, iso- 66,117 - linifolia 283 Balduilin 230,247 Atripliciolide, 9ct-( angeloyloxy )-15-hydroxy- Balduina angustifolia 246, 251 8-0-(2-methylacrylate) 295,308 - uniflora 247 -, 9ct-hydroxy-8-0-(2-methylacrylate) 295, Baldverin 286 308 Balsamin 80, 117 -, isobutyrate 71, 117 Baltimora recta 314 -, 9ct-(isovaleryloxy)-15-hydroxy-8-0- Bedfordia salicina 263 (2-methylacrylate) 295, 308 Bemadienolide 267,269 -, 2-methylacrylate 71, 117 Bemarivolide 267, 269 -, isovalerate 71, 117 Benzene 105,106,113,115,244,290 -, 9ct-(senecioyloxy)-15-hydroxy-8-0- Benzomitosenes 26 (2-methylacrylate) 200,295, 308 Benzyichloride 36 -, tiglate 71,117 Berlandiera subacaulis 200, 209 Autumnolide 233, 239, 247 Berlandin 166, 198, 200 Axivalin 180, 198,200 Bigelovin 228,247,318 -, monohydrate 198 -, iso-desacetyl- 304,318 Azidoquinones 27 Bilobalide 279, 282, 285 Aziridines 2, 4, 7, 8, 10, 13, 14, 16, 19, 20, Biological activities 50 21, 23, 28, 30, 38 Bipinnatin 224,239,240, 247 Aziridinobenzomitosane 33 Bisabenolides 49 Aziridinomitosene 30 -, biogenesis 281 -, oxidized 281 Badgerin 77, 117 2,5-Bisdimethylaminobenzoquinone 2 Badkhysidin 138, 159,291 Blennin A 277, 282 Badkhysin 174, 200 Blennin B 277,282 -, iso- 179, 200 Blennin C 277,282 Badkhysinin 136, 159,233,247,291 Bombax, lactone from 276, 282 Baeyer-Villiger oxidation 237,244 Bombax malabaricum 282 Bahia I 169,200 Boron trifluoride 37, 107, 194,223 Bahia II 169,200 Brevilin A 231,247 Bahia oppositifolia 200 Britannin 232,247 - pringlei 200 Bromination 240 - woodhousei 133 N-Bromosuccinimide 240 Bahifolin 169,200 N-Brosy1mitomycin A 3 Baileya multiradiata 247, 249, 251, 253, 255 Budlein A 71, 117 - pauciradiata 253,318 Budlein B 61,117 - pleniradiata 117,207,247,253, 255 Burrodin 226, 247 Baileyin 66, 117, 288, 293, 298, 308 Baileyolin 229,247 Cacalia delphiniifolia 282 Bakkenolide A 258,259,261,264 - hastata 264 -, 2-hydroxy- angeloyl- 261,264 Cacalolide 276, 282, 284 -, 3-hydroxy- tigloyl- 261,264 Cadinane lactones 108 Bakkenolide B 261,264 Cadinanolides 52,281,284 Bakkenolide C 261,264 -, biosynthesis 281 Bakkenolide D 261,264 Calaxin 71, 117 412 Subject Index

Calea axillaris 117 -,ovina 119 - urticifolia 308 -, pullata 221 - zacatechichi 133, 308 -, repens 201 Calein A 297,308 -, salonitana 130 Calein B 297, 308 -, scabiosa 130 Calendin 286 -, seridis 116, 130 Calendula officinalis 286 -, solstitialis 130,131,201,209 Callitrin 216,218,219,221 -, stoebe 119 Callitris columellaris 125,159,201,221 -, sventenii 315 Callitrisin 143,147,159,218,219 -, webbiana 203 -, dihydro- 143, 147, 159,218 Centaurepensin 195, 198,201 Calocephalin 186, 200 Chamazulenogen 195, 196 Calocephalus brownii 200, 204 Chamissarin 65, 117 Canambrin 227,247 Chamisselin 117 Canellaceae 265 Chamissonin 65, 97, 105, 113, 117 Canin 172, 201 -, -diacetate 148 Capenicin 271,272 -, 1(10)-epoxy- 65, 118 Carabrone 189, 191,212 -,4,5-epoxy- 66, 118 -, -4H 189,212 Chapliatrin 79, 118 Carbamates 7,8,9,10,14,16,21,23 -, acetyl- 79, 118 Carbon dioxide 32, 196 -, iso- 79, 118 Carmelin 64, 113, 117 Chartolepis intermedia 204 Carolenalin 185, 198, 201 Chiapin A 224,247 -, mono acetate 198 Chiapin B 224,247 Carolenalone 185, 198,201 Chichuahuin 62,97,99,113,118 Carolenin 185, 201 Chlorochrymorin 179, 194, 198,201 Carpesia lactone 182,201 Chlorohyssopifolin A 171,194,195,201,315 Carpesin 143, 159 Chlorohyssopifolin B 171,201,315 Carpesiolin 226, 247 ~ Chlorohyssopifolin C 170,201,315 Carpesiumabrotanoides 161, 162,201,212,247 Chlorohyssopifolin D 171,201,315 - eximium 159, 162, 165,212 Chlorohyssopifolin E 171,201,315 Cation exchange resin 105 1, 102, 104,241,289,290 CD-spectra m-Chloroperbenzoic acid 102, 103, 104 Eudesmanolides 148 Christinin 174,201 Germacranolides 92, 96 Christinin II 174, 201 Guaianolides 292 Christinin III 174,201 Pseudoguaianolides 238 Chromatography 1,37,99, 146 Centaurea americana 202 Chromium dichloride 99, 100 - aspera 286 Chromium trioxide 102, 103, 193,244, 245 - calcitrapa 119, 130, 308 Chromolaena glaberirma 118 canariensis 315 Chromolaenide 70, 118, 308 diffusa 119 -,4,5-trans-3-desacetyl-20-tiglyl- 62, 118 hyrcanica 199,208 -,3-epi-20-acetoxy- 69,118 hyssopifolia 165, 201 -,20-hydroxy- 118 iberica 119 -, 20-tiglinoyloxy- 70, 118 - janeri 205 Chrymoranolide 52 kurdica 119 Chrysanin 141,159 linifolia 201,314,315,316 Chrysanolide 77, 118 melitensis 221 Chrysanthemum achillea 119 micranthos 119 cinerariaefolium 118,129,159,160 - millitensis 130 coccineum 129 -, nigra 201 indicum 200, 209 Subject Index 413

- morifolium 201 Cordilin 227,248 - parthenium 128,163,201 Coriamyrtin 271,272 - poteriifolium 120 Corianin 271, 272 Chrysartemin A 167,201 Coriaria angustissima 273 Chrysartemin B 172,198,201 - arborea 272 Cichorium intybus 205 - japonica 272, 273, 287 Ciliarin 71,118 - lurida 273 Cinerenin 69, 118 - myrtifolia 272 Cinnamolide 265, 267, 269 - ruscifolia 273 Cinnamosmafragrans 269 - sp. 268 - sp. 265 - thymifolia 273 Cinnamosmolide 267,269 Coronopilic acid 242 Circular dichroism s. CD-spectra Coronopilin 224, 242, 244, 245, 248 Citrulline 21 -, anhydro- 248 C14 -labelled compounds -, dihydro- 249 Glucosamine 19 Coryamyrtin 271,272 Mitomycin 19 Cosmos hybridus 119 Pyruvic acid 21 - sulphureus 119 U reido-citrulline 21 Costunolide 51,53,54,60,61. 82, 83, 90, 92, Claisen rearrangement 33, 36 95,96,98,102,104,105,107,111,112,114, Clibadium surinamense 120 119, 288, 308 Clitocybe illudens 282 -, cis,cis-3cx-acetoxy-8~-hydroxy- 73, 119 Cnicin 62, 96, 97, 119, 308 -, 4,5-cis-14-acetoxy-8~-( 4-hydroxy- Cnicothamnus lorentzii 308,312,317 tiglinoyloxy)- 70, 119 Cnicus benedictus 119, 130 -, diepoxide 294, 308 Cocculus indicus 272 -, 11,13-dihydro- 64,90,98,112, 113, 119, Colartin 138, 159 156 Collidine 152, 153 -, 3~-9cx-dihydroxy-8~-angeloyloxy- 62, Collumelarin 183,201 120 -, dihydro 186,201 -, 3~-9~-dihydroxy-8~-(2-methylbutanoyl- -, iso- 280, 282 oxy)- 293, 308 Collybia maculata 282 -, I,IO-epoxide 102,146 Collybolide 280, 282 -, hexahydroderivative 98 -, iso- 280, 282 -, 4,5-cis-14-hydroxy-8 ~-( 4-hydroxy- Colorata-4(l3),8-dienolide 266, 269 tiglinoyloxy)- 70, 120 Commiferin 59,144,159 -, cis,cis-2cx-hydroxy- 73, 120 Commiphora myrra 159 -, 8-hydroxy- 61, 120 Compositae 49, 236 -, 9~-hydroxy- 120 Compressanolide 303, 315 -, 14-hydroxy- 61, 100, 120 Conchosin A 224,247 -, 14-hydroxy-8~-( 4-hydroxytiglinoyloxy)- Conchosin B 224,247 62,70, 120 Confertdiolide 145,148,227,245,248 -, 15-hydroxy-8cx-isobutyryl- 293, 309 Confertiflorin 224, 248 -, 15-hydroxy-8cx-(cx-methylacryloyl)- 293, -, desactyl- 224, 248 309 Confertifolin 267, 269 -, 9~-isobutyroyloxy- 62, 120 Confertin 226, 248, 318 -, 3~-isovaleroyloxy- 62,120,293,309 -,4cx-H 226,248 -, 15-isovaleroyloxy- 62,120 Confertiphyllide 214, 222 -, 9~-(2-methylbuturyloxy)- 62, 120 Confertolide 80, 119 -, I-peroxy- 76, 113, 114, 120 Conocephalum conicum 313,317 -, 9-propionyloxy- 62, 121 Cope rearrangement 110,112,214,217,218, -, 15-senecioyloxy 62, 121 289,290 Costuslactone, dehydro- 171,201,315 414 Subject Index

Costuslactone, dehydrodihydro- 176, 202 Decipienin A 137,160 -, dehydro-1-epi-8Cl-senecioyloxy 181,202 Decipienin B 140, 160 -, dehydro-8Cl-senecioyloxy- 171, 202 Decipienin G 137, 160 Cotton effect Decipienin H 137,160 Cyclohexadienes 94 Dehydrogenation 149,151 Eudesmanolides 148 Dehydroquinic acid 21,22 Heliangolides 93, 94 Deiminomytomycin 37 Melampolides 93 Demercuration 290 Cl-Methylene-y-Iactone 93 Dendramine 268, 270, 272 Pyrazoline derivatives 96 Dendrine 268, 270, 272 Cotula hispida 309, 316 Dendrobine 268, 270, 272 Critonia morifolia 119, 159 -, 2-hydroxy- 270, 272 - sexangularis 119 Dendrobium aduncum 272 Critonilide 145,159 - findlayanum 272 -, iso- 145, 159 - nobile 272 Croptdon divaricatum 202 - sp. 268 Cumambrin A 172, 202, 315 Dendroxine 270, 272 Cumambrin B 172,202,315 - 6-hydroxy- 270, 272 -,8-desoxy 172,202 Dentatin A 135, 160 -, iso- 181,202 Dentatin B 76, 121 -, 3,4-oxide 172, 202 Desaziridinomitomycin 36 Cumanin 226, 249 Desmotroposantonin 153,154 -, 3-acetate 226, 249 Desoxyribonucleic acid 13, 14, 15, 16, 17, 18 -, diacetate 226,249 Deuterated pyridine 5 -, dihydro- 226, 249 Diatomaceous earth 2 Cupressaceae 218 Diazabicyclohexane 34 Cyanomethyllithium 36 Diazomethane 23,24,96, 195 Cyciachaena xanthifolia 248, 252 2,3-Dichloro-5,6-dicyanobenzoquinone 290 Cyclization reactions 105 Dicoma anomala 121 Cyclocostunolide 314 Dicomanolide, 14-acetoxy- 65, 121 Cl-Cyclocostunolide 105,134,159,291 -, 14-oxo- 65,121 ~-Cyclocostunolide 105, 135, 160 Dieckmann condensation 23 -, (+ )-cis- 146, 160 Diels-Alder reaction 238, 291 -, dihydro- 138, 160 3,6-Dihydrochamazulene 195, 196 Cyclodecadiene ketones 107, 108 5,6-Dihydrochamazulene 196 Cyclodecadienes 92, 94 11,13-Dihydroeudesmanolides 282 Cyclodeca-1,5-dienic sesquiterpenes 110 Dihydrotamaulipin acetate 110, III cis,cis-Cyclohexadienes 58 Dimethylamine 112, 113 trans,trans-Cyclohexadienes 92, 100 2- Dimethylamino-5-methoxy-benzo- ~-Cyclopyrethrosin 141, 160 quinone 2 -, dihydro- 141, 152, 160 Dimethyl sulfate 18 Cynara cardunculus 202 Diphenyldiselenide 150,151 - scolymus 202, 204 Diplophyllin 146, 160 Cynaropicrin 171,194,195,202,315 Diplophyllolide A 146,160 -, desacetyl- 300,315 Diplophyllolide B 286 -, de hydro- 170,202 Diplophyllum albicans 160, 289 - taxifolium 160 Damsin 224, 236, 237, 239, 240, 244, 249 Disidea pallescens 283 -, 3-hydroxy- 224, 249 Diversolide 280, 282 Decachaeta thieleana 317 Divinylcyclohexane derivatives 110 Decarbamoylmitomycin 10 Douglanin 134, 148, 149, 160 Decarboxylation 195,238,284 -, bromoacetate of tetra hydro- Subject Index 415

derivative 149 Eremophila-I,7 -dien -8, 12-olide, 3-oxo-8a-H Drimanolides 49, 265, 266 305, 319 -, biogenesis 265 -,8a-ethoxy- 305,319 Drimenin 266, 269 -, 8a-hydroxy- 305, 319 -, 6a-7~-dihydroxydihydro- 266,269 -,8a-methoxy- 305,319 -, 7~-hydroxydihydro- 266, 269 Eremophilafreelingii 282 -, iso- 266, 269 Eremophilanes 257 -, 7-ketodihydro 266, 269 Eremophilanofurans 258 Drimys confertifolia 269 Eremophilanolides 48, 49, 52, 55, 257f, 284 - winteri 269 Eremophil-7(1l)ene-12,8a-14~,6a-diolide Dugaldia hoopesi 251 , 260,262 Dugesialactone 259, 262 -, 8~-hydroxy- 260, 262 Dugesia mexicana 262 Eremophilene lactam 276, 282 Eremophilenes 284 Eleganin 71,88, 121 Eremophilenolide 257,260, 262 Elegin 286, 300, 315 -, 6~,8 ~-dihydroxy- 260, 262 Elemadienes III, 112 -,6-hydroxy- 260,262 Elemadienolides 218 -, 3~-hydroxy-6~-angeloyloxy-7 ,8-epoxy- Elemanolides 49,52, 214f, 290 305,319 -, monoepoxides 220 -, 3~-hydroxy-6~-tiglyloxy-7,8-epoxy- 305, Elephantin 63,95,97, 121 319 Elephantol 97 Eriofertin 61,102,107,113,121 Elephantopin 63,95,97, 101, 121 -, diacetate 105,106 --, deoxy- 62, 100, 101, 121 Eriofertinic acid 106 -, deoxydihydro- 100, 101 Eriofertopin 61, 121 -, 3' -dihydro- 298, 309 -,2-0-acetyl 61, 121 -, isodeoxy- 62, 121 Erioflorin 70, 99, 121 Elephantopus carolinianus 121 -, acetate 70, 121 - elatus 121 -, methacrylate 70, 121 - mollis 128, 129 Eriolangin 134,145, 149,160 - scaber 121 Eriolanin 134, 145, 149, 160, 314 - tomentosus 309 Eriolin 81, 122 Emmotin D 276, 282, 284 -, hydroxy- 81, 122 Emmotum nitens 282 Eriophyllin 70, 122 Enceliafarinosa 160, 161 Eriophyllin B 70, 122 - virginensis 161,165 Eriophyllin C 71, 122 Encelin 142,160,314 Eriophyllum confertiflorum 121, 122,221 Enhydrafluctuans 121, 123 - lana tum 160 Enhydrin 68,90,95,99,121,309 Erlangea inyangana 208 -, 11, 13-dihydroderivative 99 - remifolia 123 Epoxidation 104,220,258 Erivanin 138, 160 I,IO-Epoxygermacrolides 107, 146 Estafietin 169, 203, 315 Eregoyazidin 176, 202 -, isoepoxy- 167,203 Eregoyazin 168, 202 Estafietone, dihydro 177, 203 Eremanthin 168, 194,202 Ethanol 154,155,193,194,195 Eremantholide A 73,95, 121,291,309 Ethidium fluorescence method 17, 18 Eremantholide B 286, 295, 309 Ethyl acetate 244, 245 Eremantholide C 296, 309 Eucannabiolide 70, 122 Eremanthus elaeagnus 121, 202, 286, 309 Eudalene 149, 150 - goyazensis 124,202 Eudesma-4(15), 7(11)-diene-8~,l2-olide 144, Eremofrullanolide 262 161 -, dihydro- 262 Eudesma-5,7(11 )-diene-8~-12-olide 144, 161 416 Subject Index

Eudesma-5,7(11)-diene-13-o1-8f1,12-olide - semiserratum 122 144,161 Eupatoroxin 169,203 Eudesmanolides 49, 52, 103, 105, 106, 107, -, 10-epi- 170, 203 134,223,257,290,291 Eupatundin 169,203 -, biogenesis 134f -, acetate 169,203 -, biosynthesis 134f Euperfolide 167,203 -, chemical transformations 149f -, Ilcr-13-dihydro- 175,203 -, hydroperoxides 146, 147 Euperfolin 64, 88, 123 -, C-I f\-hydroxylated 290 Euperfolitin 64,88, 123 -, structure 134 f Eurecurvin 297,309 seco-Eudesmanolides 52, 134, 146, 147 -, 15-deshydroxy- 297,309 Eudesm-4-en-6,12-olide, I-hydroxy- Euryops brevipapposus 262 6f\,7cr,l1f\-H 137,161 Eudesm-4-en-6,12-olide, I-oxo- 6,7f\,llf\-H 137,161 Farinosin 143,161 Eufoliatin 184, 203 Farnesols 50, 59, 268, 281 Eufoliatorin 175, 198,203 -, epoxide 265 Eupachlorin 172,203 50,51, 53, 274, 281, -, acetate 172, 203 284 Eupachloroxin 172,203 Fasciculide B 298, 309 Eupacunin 80,95,122 Fastigilin A 229, 249 Eupacunolin 80, 122 Fastigilin B 229,249 Eupacunoxin 80,95, 122 Fastigilin C 228,249 Eupaformonin 69,91,93,95, 122 Favorski rearrangement 258 Eupaformosanin 69, 122 Ferolide, I-peroxy- 76, 113, 114, 123 Eupahyssopin 95, 122 Feropodin 137, 161 Euparhombin 70, 122 Ferreyanthus lactone 181,203 Euparotin 169, 198, 203 Ferreyanthus verbascifolius 203 -, acetate 169,203 Ferric chloride 24 -, bromoacetate 198 Ferula badghysi 159, 163 Eupasserin 61, 113, 122,309 - diversivittata 282 -, desacetyl 61, 122,309 - grigorjevii 200, 204, 247 Eupassofilin 63,82, 88, 122 - malacophylla 316 Eupassopilin 63,83,84, 88, 122 -- olgae 205,207,209 Eupassopin 63, 88, 122 - oopoda 140, 159, 161, 163, 165,200, 203 Eupatocunin 70, 122 - tenuisecta 315, 316 Eupatocunoxin 70, 122 Ferula hydroxylactone 140, 161 Eupatolide 61,93,95,97, 122 - hydro lactone 140, 161 Eupatoriopicrin 61,97, 123 Ferulidin 187,203,315 Eupatoriwn anomalum 309,316 Ferulin 187,203,315 - cannabinum 122, 123 Finitin 138, 161 - cuneifolium 122 Flexuosin A 228, 249 - formosanum 122 -, 2-acetate 228, 249 - glaberrimum 308 Flexuosin B 230, 249 - hyssopifolium 119,120,122 Floribundin 249 - jahanii 320 Floribundin A, dihydro- 249 - ligustrinum 205 Florigrandin 230, 250 - mohrii 120, 308, 309, 316 Florilenalin 185, 191, 198,203 -- perfolia tum 123, 203 -,4-0-acetyl-2-0-p-iodobenzoate 198 recurvans 309 -, dihydro- 186,191, 198,203 rhomboideum 122 Fluctuadin 68, 123 rotundifolium 120,203,207,208 Fluctuanin 68, 123 Subject Index 417

Fomannosin 279,282, 320 ~,monobromide 198 Fomes annosus 282 ~,neo- 185, 191,203 Formaldehyde 19,36,243 Gaillardipinnatin 228, 250 Formic acid 240,257 ~,desacetyl- 228,250 Formosanolide 315 D-Galactosamine 21 Fragrolide 267, 269 Gallicin 289, 290, 298, 309 Franserin 225, 250 Gazania krebsiana 314 Freelingnite 274, 282 Gazaniolide 299,314 Freelingyne 274, 282 ~, 8Q(-isovaleroyloxy- 299,314 ~,dihydro- 275,282 Geigeria africana 203, 212, 250, 256 Fremy's salt 23, 24 ~ aspera 203,250 Frullania dilatata 158, 160, 161, 262 ~ filifolia 203, 250, 256 ~ nisqualensis 134 Geigerin 186, 198,203 ~ tamarisci 119, 134, 158, 159, 160, 161 ~,monobromideacetate 198 ( - )-Frullania lactone 139 Geigerinin 232, 250 ( + )-Frullanolide 134, 145, 161 Germacradienes 51,105,217,274 ~,dihydro- 145, 161 ~, biogenesis 51 ~,oxy- 145, 161 ~, 2,3-epoxidized dilactones 217 (-)-Frullanolide 134, 161 Germacra-l (l 0)-4-dien-6, 12-olides 87, 214, Frutescin 69, 123 288 Fruticosin 188,212 Germacranolides 48,49, 51, 52, 58f, 76, 82, Fuegin 267, 269 88,93,156,214,288 Fukinanolides 49, 52, 257f, 261, 264 ~, chemical transformations 96f ~, 9-acetoxy- 261,264 ~,endocyclic 289 Fukinanolide F 319 cis,cis-Germacranolides 49,58,73, 89 Fukinolide 261,264 Germacranolide, 4,5-cis-3~-hydroxy- 69, 123 ~,dihydro- 261, 264 seco-Germacranolides 52, 59 Fukinolide F 319 Germacrene A 53, 54 Fukinolide S 261,264 Germacrene B 55 Fukinone 258, 259 Germacrene D lactone 78. 123 Furanoeremophilanes 257 Germacrolides 49, 58, 82, 88, 89, 92, 94, 95, Furanoeremophilan-14~,6Q(-olide 261,262 96, 100, 113,293 Furanogermacradiene 290 ~,4,5-epoxides 189, 191,237,238 Furanogermacranolides 74, 88,92, 95 ~, 7,6-lactonized 61,87,88,96, 102 Furanosesquiterpenes 55 ~, 7,8-lactonized 93,96 Futronolide 266, 269 2,3-seco-Germacrolides 49 Germafurenolide, iso- 217,221 Gafrinin 188,212 ~,iso-hydroxy- 217,221 Gaillardia amblyodon 246, 250 Germafurenolides 49 ~ aristata 163, 165,255 Germanin A 62, 123 ~ fastigiata 249 Germanin B 80, 123 ~ grandiflora 255, 286 Ginkgoaceae 285 ~ megapotamica 250 Ginkgo biloba 282, 285 ~ mexicana 253, 255 Glaucolide A 81,95, 123 ~ multiceps 250 ~, 19-hydroxy- 81, 123 ~ parryi 249 Glaucolide B 81, 123 ~ pinnatifida 247, 250, 253 Glaucolide D 64,95, 123 ~ pulchella 163,203, 255, 286 Glaucolide E 64,95,123 ~ spathulata 255 Glaucolide G 64,95, 124 Gaillardilin 229, 250 Glechoma hederacea 124 Gaillardin 183, 191, 198,203 Glechomanolide 67, 124 ~,p-bromoacetate 198 Globicin 175,204

Fortschritte d. Chern. org. Naturs!. 38 27 418 Subject Index

D-Glucosamine 19,20,21,22 Helenanolides 49,223,236 Glucose 21,22 --, biogenesis 237, 238, 288, 293 Goyazensolide 73, 88, 124 seco-Helenanolides 237,238 -, 15-deoxy- 73, 124 Helenium alternifolium 246,247 Gradolide 303,316 - amarum 246, 247, 255 Graminichlorin 172, 204 - arizonicum 255 Graminiliatrin 169,204 - aromaticum 247,250,252,253 -, deoxy- 169,204 - autumnale 199, 201, 203, 204, 247, 249, Grandicin 189,212 250,251,252,253,255 Grandulin 161 - bigelovii 247, 255 Granilin 142, 161 - bloomquistii 250 Graveolide 143, 161 - brevifolium 247 Greenein 234, 238, 250 - campestre 250 Griesenin 189,212 - elegans 255 -, dihydro- 189,212 - flexuosum 249 Grilactone 182, 204 laciniatum 250 Grossheimia lactone 286 - linifolium 252 Grossheimia macrocephala 204 - mexicanum 250,251,252,253,286 - ossica 286 - microcephalum 250,251,252,253 Grossheimin 171,204,316 - ooclinium 250 Grossmisin 174, 204, 292 - pinnatifidum 163 Guainanolides 48,49,52,107, 108, 153, 154, - plantagineum 252, 253 166~ 187,292,302 - puberulum 316,318 -, biogenesis 166f - quadridentatum 212,250 -, chemical transformations 192 - scorzoneraeJolium 250, 252, 286 -,9,lOo:-epoxides 194 tenuifolium 250,253,255 -, structural types 166f - thurberi 255, 256 seco-Guaianolides 52, 165f, 187, 190 - vernale 250 Guaianolide la 107,302,316 - virginicum 209 Guaianolide4a 301,316 Helenium lactone 186, 204 Guaianolide 6a 302,316 Heliangin 70,91,95,99, 124 Guaianolide 6b 302,316 Heliangolide from Eupatorium recurvans Guanine 17, 18 295,309 Guanosine 17 Heliangolides 49, 58, 60, 69, 82, 88, 89, 91, 93, 94, 95, 99 Helianthus ciliaris 118 Haageanolide 62, 124 - moWs 309,311 Halshalin 186, 204 - pumilus 122 Handelia trichophylla 124, 201, 202, 204 - tuberosus 124 Handelin 178, 204 Hepaticae 134 Hanphyllin 62, 124, 309 Herbolide A 64, 124,290 Haplopappus rigideJolia 202 Herbolide B 64, 107, 124 Helenalin 205,230,238,239,241,250,318 Herbolide C 64, 124 -, dihydro- 251 Hirsutinolide-13(O)-acetate, 8 J3-acetoxy-1 013- -, dihydro-2-methoxy- 229,251 hydroxy- 298, 309 -, dihydroneo- 243 -, 8J3-(2-hydroxymethacryloyloxy)- 78, 124 -, I-epiallo- 239 -, 8J3-(2-methacryloyloxy)- 78, 124 -, iso- 230,251,286 -, 8J3-(2-methyl-2,3-epoxypropionyloxy)- -, mono bromide 239 78, 124 -, neo- 235,251 -, 8J3-propionyloxy-I0J3-hydroxy- 298, 309 -, oxide 239 -, 8J3-propionyloxy-l 0J3-hydroxy-1 (0)- -, tetrahydro- 230, 251 methyl- 298,310 Subject Index 419

Hirsutinolide, I, 13-0-diacetate, 8~-acetoxy- Hypochaerin 178, 198, 204 10~-hydroxy- 298,310 -, monohydrate 198 -, 8~-propionyloxy-IO~-hydroxy- 298,310 Hypochaeris setosus 161, 199, 204, 206 Hirsutinolide, 15-hydroxy-8~-(2-methyl­ Hypochlorous acid 194 acryloyloxy)- 78, 125 Hysterin 225, 252 Hirsutinolide, iso-8~-(2-methylacryloyloxy)- -, acetate 225, 252 78, 125 Hirsutinolide, 8~-(2-methylacryloyloxy)- 78, 125 Ienancin 272 Hirsutinolide, 8~-(2-methyl-2,3-epoxy- -, iso- 272 propionyloxy)- 78, 125 Igalan 216,221 Hirsutolide 286 Igalin 286 Homofukinolide 261, 264 Illicium anisatum 282 Homogyne alpina 264 Illudalic acid 278, 282 Hybrifarin 143, 161 Indoles 13, 16,23,25,27,37 Hydrazine 32 Indolines 26 Hydrogenation 12, 37, 98, 99, 115, 151, 156, Indolohydroquinones 14 192,289 Indoloquinones 3, 14, 15, 27 Hydrogen chloride 7, 9, 28, 109, 110, 193, Inula britannica lI6, 157, 163,203,247 239,241,289,290 - aschersoniana 311 Hydrogen peroxide 39, 150, 151,259 - germanica 123 Hydroperoxides 113, 146, 237 - grandis 157, 161, 162,212,221,286 Hydroquinones 13,14,15,26 - graveolens 161 10-Hydroxyguaianolides 195 - helenium 119,120,123,125,157,159,161, 3-Hydroxy-2-methyl but- 2-enoate 96 162,204,212,213,248 Hydroxyproline 26 - japonica 252 Hyenanche globosa 272, 273 - magnifica 157 - sp. 268 oculus-christi 203 Hyenancin 271,272 - racemosa 125, 157,310 -, iso- 271,272 - royleana 120,125,157,158,162,204,212, Hymenin 224, 239, 240, 245, 251 213 Hymenoclea monogyra 119,246 - viscosa 204, 213 - salsola 246,248,249,251,255 Inulicin 235,252 Hymenoflorin 232,251 -, desacetyl- 235, 252 Hymenograndin 230. 251 Inulolide 53,54,66, 125,218,295 Hymenolane 231,239,251 -, dihydro- 218,310 Hymenolide 233,251 -, 1~,lOa-epoxy,I,IO-H- 67,125 Hymenolin 225,251 -, 4~,5a-epoxy-4,5-H- 67, 125 Hymenoratin 230,251,318 Inuvisculide 184,204 Hymenovin 233, 251 -,4a,5a-epoxy-IOa,14a-H 184,204 Hymenoxon 233,239,251 -, iso-4-epi- 183,204 Hymenoxynin 234,251 Iodine azide 29 Hymenoxys acaulis 249 Iresin 265, 268, 269 - anthemoides 247, 255, 256 -, dihydro- 268, 269 - grandij70ra 250,251,253 -, iso- 267, 269 - greenei 250 Iresine celosioides 269 linearifolium 252 Iresone, dihydro- 268, 269 linear is 253 Isabelin 65, 90, 99, 102, 103, 104, 113, lI5, odorata 251 125 richardsonii 251,255,256 -, lI,13-dihydro- lI5 - rusbyi 253,255 Iso butyrate 96 - subintegra 255 Isocarpha atriplicifolia 117

27* 420 Subject Index

Isocarpha oppositifolia 118 Lactarius blennius 282, 320 Isophotosantonic lactone 154, 192 - necator 282, 283 Isopropyl 113 - pallidus 320 Istanbulin A 260,262 - pergamenus 283 Istanbulin B 286 - rufus 283 Istanbulin C 305,319 - scrobiculatus 282, 283, 320 Iva acerosa 248 - sp, 284 - ambrosiaefolia 212,213 - vellereus 283 angustifolia 162 Lactarius epoxylactone 278, 283 asperifolia 159,162 Lactarius lactone I 277, 283 axillaris 200, 204, 286 Lactarius lactone II 277, 283 dealbata 212 Lactarius lactone III 277,283 - frutescens 123 Lactarolide A 307, 320 - imbricata 162 -, 3-0-ethyl- 307, 320 - microcephala 162, 163,204 Lactarolide B 307, 320 - nevadensis 248,253,286 -, 3-0-ethyl- 307, 320 - texensis 159,162 Lactaronecatorin 277, 283 - xanthifolia 246, 248, 252 Lactarorufin A 278, 283 Iva1batin 187, 190,212 -, anhydro- 278,283,285 Iva1bin 189,212 -, 3-deoxy- 278, 283 Ivalin 142, 162 Lactarorufin B 278, 283 -, acetate 142, 162 Lactarorufin, iso- 278, 283, 285 -, pseudo- 185, 198,204 Lactuca serriola 205, 316 -, pseudo-, bromoacetate 198 - virosa 205 -, pseudo-, acetate 185,204 Lactucin 180, 198, 205, 316 -, pseudo-, dihydro- 185,204 -,8-deoxy- 301,316 Ivambrin 187,212 Lactucopicrin 180, 205, 316 Ivangulin 134,145,147,162 Laferin 174, 205 I vangustin 141, 162 Lanuginolide 64,107, 125, 310 -, 1-desoxy-8-epi- 141,162 -, 11,13-dehydro 63,125 -, 8-epi- 141, 162 Laserolide 64, 105, 113, 125 -, iso-8-epi- 141, 162 -, iso- 215,221 Ivasperin 142, 148, 162 Laser trilobum 162, 125,209,221,287 I vaxillarin 180, 190, 191, 193, 204 Laserpitium archangelica 200 -, anhydro- 180, 204 - prutenicum 208 I vaxillin 204, 286 - siler 165,207,316 Ivoxanthin 224, 252 Lasiosperman, E-7, 12, 13-H-5-dehydro-12- oxo- 274, 283 Jacquinelin 181,204 -, Z-7,12,I3-H-5-dehydro-12-oxo- 274, lanerin 170, 205 283 -,chloro- 171,205 Lasolide 140, 162 Ihanilactone 305,320 Laurenobiolide 65,88,90,91,105,113,125, ludaicin 162 218 Jurinea alata 116, 286 -, 6-desacetoxy-dihydro- 66, 125 albicaulis 116 -, des acetyl 65, 103, 104, 125 - cyanoides 125 Laurus nobilis 119, 125 - maxima 130, 199,205,207 Lead tetraacetate 29 1urinea lactone 286 Lemnalactone 275,283 lurineolide 62, 125 Leucanthin A 68, 125 lurmolide 183,205 Leucanthin B 68, 103, 104, 125 Leucanthinin 67, 126 Kuhn-Roth oxidation 21 Leucodin 205 Subject Index 421

--, dehydro- 166,205,316 Linearilobin F 294,310 Leucomisin 205 Linearilobin G 294,310 Leukopenia 19 Linearilobin H 295,310 Liatrin 72, 82, 95, 126 Linearilobin I 295,311 Liatripunctin 72, 126 Linichlorin A 300, 316 Liatris chapmanii 118, 126 Linichlorin B 300,316 -- elegans 121 Linichlorin C 300,316 -- graminifolia 204 Linifolin A 228,252 -- gracilis 118 Linifolin B 228, 252 -- provincialis 129 cis-Linifolon 274, 283 -- punctata 126, 129 trans-Linifolon 274, 283 -- pycnostachya 129, 209 Linifolon, Z-2,3-dihydro-3-acetoxy- 274,283 -- scabra 121 Lipidiol 177, 205 -- secunda 126 --, iso- 177,205 -- spicata 209 Lipiferolide 63,113,114,126 -- tenuifolia 118, 209 Liriodendron tulipi{era 123,126,132,162,221 Libanotis intermedia 286 y-Liriodenolide 135, 162 Libanotis lactone 286 Liscundin 71, 126 Lidbeckia lactone 316 Liscunditrin 71, 126 Lidbeckia pectinata 205 Lithium aluminium hydride 10, 11, 37, 39 Ligolide 260, 262 Lithium azide 39 Ligucalthaefolin 261, 262 Lithiumdiisopropylamide 150, 151 Ligularenolide 260, 262 Litseaculane 74, 112, 126 --, 6~-acetoxy- 260, 262 Litsealactone 74, 112, 126 --, 6~-hydroxy- 260, 262 Longipilin 68, 126,311 Ligularia calthaefolia 262 Longipin 67, 126 -- fauriei 262 Ludalbin 134, 162 -- fischeri 262 Ludartin 166,205 -- hodgsoni 262, 264 --,dihydro- 174,205 -- macrophylla 262 Ludovicin A 134, 162 -- sp. 262 Ludovicin B 135,162 Ligulatin B 224, 252 Ludovicin C 135, 163 Ligustrin 168, 205 Ludovicin D 286 Linderadine 74, 126 Lumidihydroisabelin 115 Linderalactone 74, 88, 92, 95, 99, 100, Ill, Lumisantonin 134, 144, 149, 154, 155, 163, 112, 126, 217 --, 2-bromoderivative 149 --, iso- 88,217,221 2,4-L utidine 151 --,neo- 74,92,112,126 Linderane 74,88, 92,99, 10~ 126 --,neo- 74,112,126 Maculatin 68,99,126 --, pseudo-neo- 74, 126 --, 13-13-dihydro- 99 Lindera strychnifolia 126, 162,221 Magnolia grandiflora 117, 120, 129, 132, 308, Lindestrenolide 144, 162 314 --,dehydro- 144,162 Malaphyl 302,316 --,hydroxy- 144,162 Malaphylin 302, 316 Linearifolin A 230, 252 Manganese dioxide 100,290,291,292 Linearifolin B 235, 252 D-Mannosan).ine 20 Linearilobin A 294,310 Marasmic acid 279, 283, 285 Linearilobin B 294,310 Marasmius conigenus 283 Linearilobin C 294,310 Marginatin 64,126 Linearilobin D 294,310 Markovnikov cyclization 237 Linearilobin E 294,310 Maroniolide 298, 311 422 Subject Index

Mass spectra Melcanthin B 73, 85, 127 Ambrosanolides 238 Melcanthin C 73, 127 Costunolide 83 Melfusin 293,311 Eupassopilin 83 . Melitensin 214,221 Germacranolides 82 --, 11(13)-dehydro- 214,221 Helenanolides 238 --, dehydro-15-dehydro-8(O)-[4' -hydroxy- Melampolidin 84 methacrylate] 304, 317 Melcanthin B --, 11 (13)-dehydro-~-hydroxyisobutyrate Mexicanin A 243 214,222 Mitomycin antibiotics 5, 19 --, dehydro-8(O)-[4' -hydroxymethacrylate] Matricaria chamomilla 205, 207 304, 317 -- globifera 200,204 --, 4~-hydroxyisobutyrate 214,221 -- nigellaefolia 119 Mellitoxin 272 -- suffructicosa 129, 199, 206 Melnerin A 69,95, 127 -- zuurbergensis 211 --, 9-acetoxy- 69, 127 Matricarin 174, 205 Melnerin B 69,95, 127 --, II, 13-dehydro- 166, 205 --, 9-acetoxy- 69, 127 --, desacetoxy- 174, 206 Mercuric chloride 38 --, des acetyl- 174, 206 Meridianone 299,314 --, 11-epi- 207 Methanol 5,8,9,11,13,34,35,84,96,112, --, II-epi-desacetyl 207 239,241,244,291 Matricin 182,207 Methionine 21 Maximolide 207 Methylation 248 McLafferty rearrangements 82 N-Methylaziridine derivatives 5 Melampodin A 68, 88, 90, 93, 95, 102, 103, a-Methyl-n-butyrate 96 126 Methylene blue 113, 114 --, acetate 68, 103, 104, 127 a-Methylene-y-Iactones 148, 151, 195,288 --, 1I,13-dihydro-, 9~-methylbutyrate 68, Methyl iodide 3, 10, 100, 101, 112 127 a-Methyl-y-Iactones 151 Melampodin B 69,88,95,100,127 N-Methylmitomycin A 3,5,11 --,4,5-dihydro- 69, 127 N-Methylmitomycin C 2 Melampodin C 69,127 N-Methylmitomycins 6, 11 Melampodin D 69, 127 --, analogs 13 Melampodinin 68,88, 127, 311 --, derivatives 17 Melampodinin B 68, 88, 127 Methyl sulfonyl chloride 156,193 Melampodinin, 9-desacetyl- 127 Methyl thiol 37 Melampodium americanum 127 Mexicanin A 230,239,240,241,252 -- argophyllum 118, 127 --, dihydro- 243 - cinereum 118, 127 Mexicanin B 286 -- diffusum 311 Mexicanin C 231,252 -- divaricatum 207 Mexicanin D 252 -- leucanthum 125, 126, 127 Mexicanin E 235,238,239,240,241,243,252 -- linearilobum 310, 311 --, dihydro- 235, 252 -- longipes 126, 127 --, mono bromide 239 -- longipilum 121, 126, 127 Mexicanin H 232, 243, 252 -- perfolia tum 121 Mexicanin I 228, 253 Melampolides 49,58,67,84,87,89,91,93,94. Mibulactone 140, 163 95,96, 100, 112, 146, 188 Michael addition 31,40,153,240,291 --, 4,5-epoxide 238 Michelenolide 311 Melampolidin 67,84, 127 Michelia champaca 128 Melanoselinum decipiens 160 -- compressa 308,310,311,314,315,316 Melcanthin A 73, 127 -- lanuginosa 125, 128, 129 Subject Index 423

Micheliolide 301,316 Mortonia gregii 283,320 Micordilin 214,216,221 Mortonin 283 Micranthin 286 Mortonin A 279, 306, 320 Microcephalin 142, 148, 163 Mortonin B 306, 320 -, dihydro- 152 Mortonin C 305, 320 Microhelenin A 230, 253 Mortonin D 306, 320 Microhelenin B 231,253 Multigilin 228,253 Microhelenin C 231,253 Multiradiatin 232, 253 Microlenin 234, 238, 239, 253 Multistatin 232, 253 Miel em poi sonne 272 Munchnone 26 Mikania cordifolia 221,311,312 Munnozia gigantea 315 - monogasensis 127 - moroni 311 - scandens 127,130,221 Muricatin 171,207 - sp. 207 Myelo suppression 18 Mikanocryptin 184, 207 Myocalia reticulata 265,269 Mikanolide 66, 127 -, deoxy- 65, 103, 104, 127 -, dihydro- 66,95, 127 Naphthoquinone 34 Millefin 64, 128 Nenitzescue indole-synthesis 25 Millefolide 286 Neoleonin 232,253,272 Miscandenin 214,217,218,221 Neolitsea aciculata 126,133,221 Mitiromycin 2, 5, 7 - sericea 222 Mitomycin A 1, 2, 3,4, 5, 10, 11, 16, 23, 35, - zeylanica 126,133 36,40 Nerolidyl pyrophosphate 50 Mitomycin B 1,2, 3,4, 5, 7, 10, 11, 13, 16, Neurolaena lobata 311 21,35 Neurolenin A 297,311 -, methyl ether 10 Neurolenin B 297, 311 Mitomycin C I, 2, 3, 5, 8, 9, 10, 11, 12, 16, Nevadivalin 286 18,21, 36,40 Nidulariaceae 265 -, I-hydroxy-2-amino-derivative 7 Nitrogen 244, 245 Mitomycins 1f Nitroindoline 25 -, analogs 13 NMR-spectra -, biosynthesis 19 Dihydroinunolide 218 -, derivatives 17 Eudesmanolides 148 -, isolation 1 Furanogermacranolides 88 -, mechanism of action 13 Germacranolides 82, 85, 102 -, structure 1 Germacrolides 88, 100 -, synthetic studies 22 Guaianolides 292 -, transformation products 7 Heliangolides 88 Mitosanes 22, 23, 31, 34 10-Hydroxyguaianolides 195 Mitosenes 5, 22, 23, 26, 28, 30 Melampolides 88 Mokko lactone 176, 207 Mitomycin antibiotics 4 Molephantin 79, 95, 128 Pseudoguaianolides 238 Molephantinin 79, 128 Santonin derivatives 148 Mollisorin A 293, 311 Sesquiterpene lactones 48, 49, 57 Mollisorin B 293,311 Unsaturated ring aldehydes 100 Monogynin 286 Nobilin 60,61,69, 128,270,272 Montanoa tomentosa 132 -, 3-dehydro- 70, 128 Montanolide 183,207,292,303 -, 3-epi- 69,128 -, iso- 183,207,292,303 -, 1,1 O-epoxy- 70, 128 -, iso-acetyl- 183,207,292, 303 -, iso-hydroxy- 76, 128 Moquinea velutina 158, 159, 160 N orhelenanolides 238 424 Subject Index

Norpseudoguaianolides 243, 244 Parthemollin 187, 198,212 Novanin 62, 105, 128 -, acetyl- 187,212 Nuclear magnetic resonance s. NMR-spectra Parthenice mollis 212 Nuclear Overhauser effect 90 Parthenin 224,239,240,245,253 Parthenium alpinum 255. 256 Oaxacin 224, 253 - bipinnatifidum 246,247,249, 252 Ocotea guianensis 314 - cineraceum 255 Ocotealactol 300, 314 - confertum 247,248,251, 252, 255, 256 Oferin 174, 207 - fruticosum 212,247,255,256 Olgin 174,207 - hysterophorus 253 Olgoferin 174,207 - incanum 246, 248, 252 Onopordon acanthium 128 - integrifolium 256 - algeriensis 128 - ligula tum 252, 256 - alexandrinum 128 - lozanianum 256 - brackteatum 128 - schottii 248, 256 - illyricum 128 - sp. 236 - leptolepis 309,311,317 - tomentosum 212,252,253, 318 - nervosum 128 Parthenolide 60, 63, 95, 107, 113, 128, 311 - tauricum 128 -, 9o:-acetoxy- 63, 129 Onopordopicrin 62, 128, 311 -, 9~-acetoxy- 63, 129 Oopodin 138, 163 -, dihydro- 64, 107, 109, 110, 113, 129. 311 -,dehydro- 135,163 -, I-peroxy- 76. 113, 129 Orchidaceae 368 Partition chromatography 2 Orientin 80, 128 Paucin 229,239,253,318 Orizabin 71, 128 -, monohydrate 239 Osmitopsin 179,207 Pectorolide 62, 99, 129 -, 1,8-epoxy- 179, 207 -, 11 ~-dihydro- 103 -, 4,5-epoxy- 179, 207 Pelenolide, hydroxy 81, 95, 129 Osmitopsis asteriscoides 207 Pelenolide A, keto- 81,129 Osmium tetroxide 39 Pelenolide B, keto- 81, 129 Osmylation 38 Penicillium purpurogenum 265, 269 Othonna cylindrica 283 Pentalenolactone 279, 283, 320 Othonna, lactone from 276, 283 Pentzia elegans 203 Ovatifolin 61,95, 128 Peracetic acid 237, 244 Oxalate 23 Peracids 102,192,194,220,291 Oxazines 5, 6, 7 Perchloric acid 105 Oxazolines 26, 29 Periodate cleavage 19 C-15-0xo-germacrolide 290 Permanganate oxidation 3, 12 12-0xolemnacamol 275, 283 Peruvin 226, 253 Oxygen 31, 34, 35, 37, 54. 114,244,245 Peruvinin 226, 253 Oxymercuration 290 Petasites albus 262, 264 Ozonolysis 12 - fragrans 264 - hybridus 262, 264, 282 Palladium 37,98,99,115,149,150,151,156, - japonicus 262,264,319 192 - officinalis 262, 263 Pallescensin 3 275, 281, 283 Petasitolide A 260, 262 Paniculide A 275,281,283 Petasitolide B 260, 263 Paniculide B 275,281,283 Petiolaride 173, 207 Paniculide C 275,281. 283 Peucephyllin 69,91, 95, 129 Paralemnarin digitoformis 283 Peucephyllum schottii 129 -, thyrsoides 283 Phantom olin 78,95, 129 Parishin C 174,207 Phenylchloroformate 23, 24, 37 Subject Index 425

Phenylselenium bromide 39 Provincialin 70, 82, 99, 129 Phosgene 8 Prutenin 173, 208 Phosphorous acid trimethylester 38, 39 Pruteninone, 4-acetoxy- 208 Photochemical reactions 113, 244, 245, 257. ~,8-acetoxy- 174,208 290 --, 8-ange1oyloxy- 174, 208 Photoisabelin 115 ~,iso-8-acetoxy- 176, 208 Photooxidations 34, 113, 114,291 Pseudoguaianolides 48. 49. 52. 153. 223[ Photosantonic acid 154 238,288,293 Picridin 167,207 ~, biogenesis 223f ~,dihydro- 175,207 ~, structural elucidation 238 Picridium cristallinum 206, 207 ~, structural types 22lf ~ ligula tum 207 Pseudoguaian-6,12-olide, 8-acetoxy-3-oxo- Picrohelenin 230, 253 226,253 Picrotin 270, 272 ~, 4-hydroxy-3-oxo- 226, 254 Picrotoxinin 271, 273 seco-Pseudoguaianolide 52 Picrotoxins 268 Pseudohandelia umbellifera 309 Pinnatifidin 141,148,163,291 Pseudowintera colorata 269 Plagiochila yokogurensis 320 Psilostachyanolides 236, 237 Plagiochilide 306, 320 Psilostachyin 227.244.254.318 Platinum 12,192 ~, an hydro- 244, 245 Platium oxide 98,99,151 Psilostachyin B 227, 254, 318 Platycarpha glome rata 130 Psilostachyin C 227,236,237,254,318 Platyphyllide 276, 283, 284 Psilostrophe cooperi 255 Pleniradin 186,207,292,293,303,316 Psilotropin 233, 255 Plenolin 231,239,253 Ptarmica cartilaginea 206 ~,p-iodobenzoate 239 Puberolide 303,316 Pluchea dioscorides 163 Pu1chellidine 229. 255 Pluchea, lactone from 134,163 --, neo- 231,255 Podanthus ovatifolius 121, 128,211 Pu1chellin 228,239,255.318 Podochaenium eminens 201,210,211 --, dibromide 239 Polhovolide 303,316 ~. neo- 230,255 Polydalin 67,94,129,311 Pulchellin B 142, 163 Polygonum hydropiper 269 Pulchellin C 19,142.163 Polymatin A 296,311 ~,diacetate 149 Polymatin B 296, 311 Puichellin D 286 Polymatin C 296, 311 Pu1chellin E 142, 163 Polymnia maculata 126, 309, 311 Pulchellin F 142, 163 ~ uvedalia 121, 129, 132 Pummerer rearrangement 292 Polynuc1eotides 17. 18 Punctaliatrin 72, 129 Porella sp. 265. 269 Purpuride 267, 269 Porfiromycin 2,3,5,10. 11,21,36,38 Pycnolide 59,81, 129 Potassium t-butylate 28 Pyrazoline derivatives 96 Potassium carbonate 3, 96 Pyrethrosin 65, 95, 106, 107, 129 Potassium hydrogencarbonate 243 Pyridine 5, 192. 193, 240, 242. 259 Potassium hydroxide 108, 193 Pyrovallerolactone 277 Potassium permanganate 3, 293 Pyrrole Grignard reagent 34 Preeupatundin-2-acetate, 8~-angeloyloxy- Pyrroles 34 5cr-hydroxy- 180, 207 Pyrrolo-(l,2-a)-indole 23.26 Preeupatundin, 8~-angeloyloxy- 180,207 Pyruvic acid 21,22 ~,5cr-hydroxy-8~-tiglinoyloxy- 180, 208 ~. 8~-tiglinoyloxy-. 1O,15-epoxide 169,208 C!uadrone 306,320 Prins reaction 221 C!uing Hau Sau 275.283, 284 426 Subject Index

o-Quinone methides' 13,15,18 Sant-4(14)-en-6,12-olide C, I~-hydroxy- Quinones 14, 15, 16, 21, 23, 25, 31, 34, 35, 138, 164 36,38,40 Santonic acid 153, 154 Cl-Santonin 137,146, 148, 153, 154, 155, 164, Radiatin 229, 239, 255 291,292, 314 Red cation 289, 290 --, 2-bromoderivative 149 Repandin A 78, 129 --, derivatives, NMR 148 Repandin B 78, 129 --,1,2-dihydro- 137,164 Repandin C 78, 129 --, 4,5-epoxide 153 Repandin D 78, 129 --, II-oxy- 137, 164 Repin 170, 208 ~-Santonin 137, 148, 164, 199,314 Retroaldol reaction 238, 242, 243 --,2-bromoderivative 149 Reynosin 135,146,148,151,163,314 'l'-Santonin 139, 165 --, dihydro- 220,223,299,314 --, deoxy- 139, 165 --, tetrahydro- 151 Saupirin 181,208 Ridentin 76, 129 Saurin 181,208 --, dihydro- 76, 130 Saussurea aegypticus 286 Ridentin B 135, 163 -- elegans 286, 315 Ridentin, iso- 297, 311 -- elongata 131 Rose Bengal 291 -- lappa 119,201,202,221 Rothin A 135,163 -- neopulchella 208 Rothin B 135, 163 -- pulchella 208 Rupicolin A 167,208 Saussurea lactone 214,220,221,286,317 --, 15-acetoxy-1 ~-hydroxy-8-(2Cl-acetoxy­ Scabiolide 65, 130 ethyl)-acrylate 167,208 Scandenolide 65, 130 --, 3Cl,4Cl-diacetoxy-3,4-dihydro-8-(2Cl- --, dihydro- 66, 130 acetoxyethyl)-acrylate 168,208 Scolypopa australis 272 Rupicolin B 168,208 Selenium 149, 150 Rupin A 173, 208 Selenium dioxide 258, 259 Rupin B 173, 208 Selenoxide elimination 38 Russulaceae 284 Selianolides 114 Rutifolin 286 Semopodin 140, 165 Senecio aegyptius, keto lactone from 286 Salonitenolide 62, 96, 97, 130 Senecio nemorensis 319 --, 8-desoxy- 62, 100, 130 -- platyphylloides 283 --, 8-desoxy-15-(2,3-dihydroxy-isobutyryl- -- pyramidatus 319 oxy)- 293, 311 -- vellereus 262 --, 8-desoxy-15-(hydroxyisobutyryloxy)- Sen mokko 207 293, 311 Senoxepin 276, 283, 284 --, 8-desoxy-15-(3-hydroxy-2-methylacryl• Sericealactone 217, 221 oxy)- 293,312 --, desoxy- 217,221 --, 8-desoxy-15-(2,3-epoxy-isobutyryloxy)- Sesquiterpene lactones 47f 293,312 --, biosynthesis 50 --, ~-ll, 13-dihydro-8-desoxy- 64, 130 --, conformational considerations 88 --,8(O)-2-methylbutyrate 293,312 --, epoxides 50 Salonitolide 66, 130 --, ester side chains 56 Salsolin 225,255 --, hydroperoxides 50 Santamarin 146,163,314 --, sceletal types 50 --, dihydro- 137, 163, 220, 223 --, structure determination 82 --, I ,2-dihydro-ll, 13-dehydro- 292 Sesquiterpene hydro peroxides 113 --, epoxy 134, 163 Sesquiterpenes, biogensis 113 Sant-3-en-6,12-olide C, I~-hydroxy- 163 Sieversin 182, 208 Subject Index 427

Sieversinin 209 Subacaulin 166,209 Sigesbeckia orientalis 128 Subluteolide 170, 209 Silerolide 139, 165 Substance C 271, 273 Silica gel 37,107,108,146 Substance D 271, 273 Silver oxide 32, 35 Sulferalin 232, 255 Simsia dombeyana 130 Sulfuric acid 102, 103, 195, 196, 239, 242 Simsiolide 67,130 Symmetric lactone from Bedfordia halicina Smyrnium connatum 319 132 - olusantrum 262, 286 Sodium 29 Tabarin 138, 165 Sodium acetate 102, 104 Tachillin 165, 287 Sodium azide 28 Tagitinin A 72, 131 Sodium borohydride 10, 11,24,39,98,99, Tagitinin B 71,131 150,151,195 Tagitinin C 79, 131 Sodium dithionite 12 Tagitinin D 131 Sodium hydrogencarbonate 112 Tagitinin E 298,312 Sodium hydride 10,39 Tagitinin F 72,131 Sodium hydroxide 97,195,196 Talassia transiliensis 209 Sodium iodide 156 Talassin 316 Sodium methoxide 10, 12,26,29, 36, 39 Talassin A 174,209 Sodium sulfite 12 Talassin B 174, 209 Sodium thiosulfate 15 Tamaulipin A 61, 88, 90, 95, 99,131 Solstitialin 177, 198,209 -, dihydro-, acetate 110, 111 -, acetate 177,209 Tamaulipin B 62, 99, 113, 131 Sonchus hierrensis 163 Tamirin 77,131 - jacquini 204 Tanachin 77 - pinnatus 204 Tanacetin 135,150, 151, 165 - radicatus 204 Tanacetum balsam ita 160 - tuberifer 165 - chilliophyllum 131 Spathulin 228, 238, 239, 255 - myriophyllum 131,209 -, diacetate 239 - pseudoachillea 131, 165, 287 Spicatin 169, 198,209,316 -- santolina 315 -,epoxy- 169,209 - tanacetioides 123, 163 -, hydro bromide 198 - vulgare 158, 163, 165,287 -, hydrochloride 172, 209 Tanacetum lactone I 287 Spiciformin 66, 103, 104, 130 Tanacetum lactone II 287 Stenophyllolide 286 Tanacetum lactone III 287 Stevia rhombifolia 255 Tanachin 77,131 - serrata 117, 201 Tanacin 65, 107, 131 Stevin 226, 255 Tanamyrin 187,209 Stizolicin 63, 131 Tanapsin 141, 165 Stizolin 63, 131 Tatridin A 77, 131 Stizolophus balsam ita 117,131 Tatridin B 77,131 - coronopifolius 131 Tatridin C 77,131 Stramonin B 293,304,318 Tauremisin 138, 165 Streptomyces 8403-MC 283 Taurin 137, 165 caespitosus 1 Telekia speciosa 157,165 - reticula var. shimofusaensis 7 Telekin 142, 165 - verticillatus 2 -, 3-epi-iso-l,2-dehydro- 299,314 Streptoverticillatium ardus 2 -, 3-epi-iso-l,2-dehydro-, acetate 299,314 Strontium carbonate 192 -, 3-epi-iso-ll, 13-dihydro- 300, 314 Styrene oxide 34 -, iso- 142, 165,291 418 Subject Index

Telekin, iso-dehydro- 299,314 Trichloroacetyl isocyanate 85 -, iso-3-epi- 142, 165 Trifloculoside 173, 209 Temisin 215,221 Trilobolide 182,209 -, dihydro-iso- 287 -, iso- 287 Tenuferidin 316 Tripenyl phosphine 113, 114 Tenuferin 316 Tritium labelled guanine 18 Tenuferinin 316 Trixikingolides 306, 320 Tenulin 231,238,239,242,255,318 Trixis sp. 320 -, bromoderivative 239 Tuberiferin 136, 148, 165 -, iso- 229,255 Tulipdienolide, epi- 214,221 -, iso-des acetyl- 229, 242, 255 Tulipinolide 61, \05, 132, 313 Terpenoids, hydroxylated 50 -, desacetyl- 61,132 Tetragenotheca helianthoides 312 -, epi- 61, 98, 105, \07, 108, 113, 132, 222, ~~ ludoviciana 311,312,313 313 ~~ repanda 129,311 -, epi-, diepoxide 63, 132 Tetrahelin A 216,296 Tutin 271,273 Tetrahelin B 212,297 -, pseudo- 287 Tetrahelin C 296, 312, 316 Tutinanolides 49,268, 270 Tetrahelin D 212,296 -, biosynthesis 268 Tetrahelin E 212,296 Tetrahelin F 212,297 Ugandensolide 266,269 Tetrahydrofuran 39, 150 Un symmetric lactone from Bedfordia salicina Tetraludin A 312 Tetraludins B, C and D 312,396 263 Ureido-citrulline 21 Tetraludins E, F, G, H, L ], K, L, M, and N Urospermal A 62,90,102,132 296,313 Urospermal B 62,102,132 Tetraneurin A 224, 255 Urospermum dalechampii \32 Tetraneurin B 224, 244, 256 Ursinia anthemoides 287 Tetraneurin C 225, 256 Ursiniolide A 287 Tetraneurin D 225, 256 Ursiniolide B 287 Tetraneurin E 225, 256 Ursiniolide C 287 Tetraneurin F 225, 256 Uvedalin 67,94,99,132 Themoidin 234, 256 -, 11,13-dihydro- 99 Thiele acetoxylation 23, 24 -, 4,5,11,13-tetrahydro- 99 Thieleanin 303, 317 -, hexahydro- 99 Thionyl chloride 192,242,259 UV-spectra Thrombocytopenia 19 Germacranolides 92 Thurberilin 229, 256 Mitomycins 2 Tifruticin 79, 131 -, deoxy- 79, 131 Tiglate 96 Vahlenin 136, 165, 314 Tirotundin 72, 131, 313 Valdiviolide 267,269 -, ethyl ether 72, 95, 132 Vallerolactone 277, 320 Tithonia diversifolia 131, 313 -, pyro- 277, 320 - fruticosa 131 Vanillosmin 209 ~- rotundifolia 131, 132,312 -, 8C(-senecioyloxy- 168, 209 - tubaeformis 128 Vanillosmopsis erythropappa 124, 202, 209 p-Toluenesulfonic acid 105,106,193,240 Venidium decurrens 204 Tomentosin 62,132, 188, 189,212 - hirsutum 286, 287 -, 8-epi- 213 Venidolide 287 -,4-H- 188,213 Verafinin 216, 221 Toxicodendrum capense 272, 273 Verafinin B 287 Subject Index 429

Verafinin C 216,221 Viguiestenin 73, 133, 313 Verbesina aft coahuilensis 221,287 -, desacetyl- 73, 133,313 - aft stricta 222 Vilsmaier-Haack formylation 23,24 Verlotorin 132 Vinylindoles 29 -,anhydro- 76,133 Virginin 143, 165 Vermeerin 233,238,256 Virginolide 185, 209 Vermeerin B, dihydro- 256 Viscidulin A 176, 209 Vernodalin 214,221 Viscidulin B 176, 209 Vernodalol 217,221 Viscidulin C 176, 209 Vernodesmine 134, 144, 149, 165 Vulgarin 165 Vernoflexin 171,209 Vernoflexuoside 171, 209 Waddel-Stocklin-Geissman rule 148 Vernolepin 214,222,317 Wagner-Meerwein rearrangement 242 Vernolide 63,95, 133 Warburgia ugandensis 269 -,hydroxy- 63,133 Wedelia rugosa 162 Vernomenin 214,215,222 Winterin 266, 269 Vernomygdin 80,133 Wolf-Kishner reduction 24 Vernonia amygdalina 133,221 Woodhousin 71,95, 133 ~ angulifolia 124, 125 Wormwood oil 195 - anisochaetoides 210 - anthelmintica 221 Xanthanene 259,263 - arkansana 126 Xanthanodiene 259, 263 - baldwini 123, 286 Xanthanol 188, 213 - colorata 133 -, iso- 188,213 - conferta 119 Xanthanolides 49,52, 156f, 189 - fasciculata 126 -, chemical transformations 192 - flexuosa 209 Xanthatin 188,189,213 - glauca 123 Xanthinin 188, 189,213 - guineensis 221,222 -,2-desacetoxy- 213 - hirsuta 120, 121, 124,201, 202, 210 Xanthinosin 188,213 - hymenolepis 223 Xanthium canadense 263 leiocarpa 124 commune 213 - marginata 126,309 italicum 213 - natalensis 203 occidentale 213 - noveboracensis 125,210 orientale 213 - nudij70ra 133,202,209 - pennsylvanicum 213 - oligocephala 202, 209 - riparium 213 - pectoralis 129,133,165 -' sp. 213 - saltensis 309,310 - spinosum 213 - scorpioides 309,310,317 - strumarium 213 - sp. 286 Xanthumin 188,213 - sublutea 209 -, desacetoxy- 188,213 - trij7oculosa 209 Xanthuminol 188,213 - unij70ra 123 Xeranthemum cylindraceum 209 Vernopectolide A 63, 133 Xerantholide 184, 209 Vernopectolide B 62, 133 X-ray investigations Vernudifloride 66, 133 Enhydrin 90 Viguiepinin 295,313 Eudesmanolides 149 Viguiera angustifolia 117 Eupatolide 93 - buddleiaeformis 117 Germacranolides 96 - pinnatilobata 313 Germacrolides 87, 91, 96 - stenoloba 133 Guaianolides 198,292 430 Subject Index

Heliangolides 96 -,71X-hydroxy-3-desoxy- 171,210 Melampolides 87,90,96,100 -, 71X-hydroxy-3-desoxy-II~, 13-dihydro- Mitomycin antibiotics 3, 12, 34 177, 210 Pleniradin 293 -, 81X-hydroxy-ll~, 13-dihydro-3-dehydro- Pseudoguaianolides 292 177,210 Sesquiterpene lactones 96 -, senecioyl- 171,210 Xylene ILl -, 4~, 14, 11 IX, 13-tetrahydro-3-dehydro- 210 Yejuhua lactone 181,209 -, 4~, 15, II~, 13-tetrahydro-3-dehydro- Yomogiartemin 301,317 177,210 Zaluzanin D 171, 2ll, 317 Yomogin 142, 148,165 -, 81X-acetoxy 300, 317 Zacatechinolide, I ~-acetoxy 71, 133 Zempoalin A 216,222 -, I-oxo- 71, 133 Zempoalin B 216,222 Zaluzania angusta 209,210,211,317 Zexbrevin 72, 133 - montagnifolia 308, 314, 317 Zexbrevin B 71, 133 - pring lei 313 Zexbrevin C 81, 133 - robinsonii 210 Zexmenia brevifolia 133 - triloba 162,201,210,211,301,317 - phyllocephala 157 Zaluzanin A 187,192,193,209,317 Zeylanane 75, 92, 133 -, anhydroderivative 193 Zeylanicine 75, 133 Zaluzanin B 187,209,317 Zeylanidine 75, 133 Zaluzanin C 171,210,317 Zeylanine 75, 92, 133 -,81X-acetoxy- 300, 317 Zinaflorin I 215, 222 -, 13-acetoxy-lI, 13-dihydro-7, II-dehydro- Zinaflorin II 215, 222 3-desoxy- 173, 210 Zinaflorin III 215, 222 -, anhydro- 193 Zinarosin 216, 223 -, de hydro- 170,210 -, dihydro-, diacetate 216,223 -, dehydro-9~-hydroxy- 301, 317 Zinc 156 -, desoxy- 210 Zinc-copper couple 99, 100, 101, 194, 195 -, 4~-14-dihydro-3-dehydro- 171,210 Zinnia acerosa 222 -, II, 13-dihydro-7, II-dehydro-3-desoxy- - haageana 124 173,210 - paucij70ra 222 -, 3-epi- 171,210 Zuurbergenin 166,211

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Volume 34: 63 figures. X, 620 pages. 1977. ISBN 3·211-81415-9. Contents: C. R. ENZELL, I. WAHLBERG, and A. J. AASEN, Iso• prenoids and Alkaloids of Tobacco - A. R. PINDER, The Chemistry of the Eremophilane and Related Sesquiterpenes - D. GROSS, Phyto• alexine und verwandte Pflanzenstoffe - K. H. OVERTON and D. J. PICKEN, Studies in Secondary Metabolism with Plant Tissue Cul• tures - D. P. CHAKRABORTY, Carbazole Alkaloids - J. JACOB, Biirzeldriisenlipide - W. VOELTER, Hypothalamus-Regulationshor• mone - Author Index - Subject Index.

Volume 35: VIII, 589 pages. 1978. ISBN 3-211-81460-4. Contents: O. R. GOTTLIEB, Neolignans - K. HERRMANN, Hydroxy• zimtsauren und Hydroxybenzoesauren enthaltende Naturstoffe in Pflan• zen - G. PATTENDEN, Natural 4-Ylidenebutenolides and 4-Ylidene• tetronic Acids - R. D. H. MURRAY, Naturally Occurring Plant Coumarins - G. OHLOFF, Recent Developments in the Field of Naturally-Occurring Aroma Components - Author Index - Subject Index.

Volume 36: 11 figures. VII, 425 pages. 1979. ISBN 3-211-81472-8. Contents: F. W. WEHRLI and T. NISHIDA, The Use of Carbon-13 Nuclear Magnetic Resonance Spectroscopy in Natural Products Chemistry - G. OHLOFF and I. FLAMENT, The Role of Heteroatomic Substances in the Aroma Compounds of Foodstuffs - A. J. WEIN• HEIMER, C. W. J. CHANG, and J. A. MATSON, Naturally Occurring Cembranes - Author Index - Subject Index.

Volume 37: 8 figures. IX, 367 pages. 1979. ISBN 3-211-81528-7. Contents: J. M. BRAND, J. CHR. YOUNG, and R. M. SILVERSTEIN, Insect Pheromones: A Critical Review of Recent Advances in Their Chemistry, Biology, and Application - M. McNEIL, A. G. DARVILL, and P. ALBERSHEIM, The Structural Polymers of the Primary Cell Walls of Dicots - U. SCHMIDT, J. HAuSLER, ELISABETH OHLER, and H. POISEL, Dehydroamino Acids, a-Hydroxy-a-amino Acids and a-Mercapto-a-amino Acids - Author Index - Subject Index.

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