Subject Index Absolute configuration 28, 30, 267 A-Ring protons (NMR), C-6 and C-8 261-265 Acacetin 43, 48, 55, 57 -- -,C-5 264 -, UV spectra of 90 Artemetin 43, 56, 60, 277 Acacetin 7-0-glucoside 43,55, 58 -, NMR spectrum of 308 - -, UV spectra of 91 -, UV spectra of 155 Acetylated aglycone 31,45,271 Astilbin 40, 170, 172, 174, 278 Acetylation of TMS ethers 255, 259 -, NMRspectrum of 327 7-Acetyloxy-6-carbomethoxyisoflavone 277 -, UV spectra of 255 -, NMR spectrum of 312 Aurone 40 Acid hydrolysis 24 Aurones, NMR spectra index 274 Afrormosin 14, 166, 169, 173,278 -, -- interpretation 254--272 -, NMR spectrum of 320 -, numbering system 13, 227 -, structure of 20 -, paper chromatography 13 -, UV spectra of 195 -, thin-layer chromatography 22 Aglycone, degradation 28 -, UV spectra index 230 -, identification 27 -, UV spectra interpretation 227,230 -, methylation and acetylation 31,45 - (see also UV and NMR) Baicalein (5,6,7-trihydroxyflavone) 43,45,57 Aluminum chloride for UV spectroscopy 35 - -, UV spectra of 77 --- -, chalcones and aurones 229 Baicalin (5,6,7-trihydroxyflavone 7-0-glucuronide) --- -,5-deoxy-7-hydroxyflavones 53 43, 55, 57 --- -, flavones and flavonols 50-56 -- -, UV spectra of 78 --- -, isoflavones, flavanones, and Baker-Venkataraman transformation 28 dihydroflavonols 171 Bands land II 41 Amentoflavone 43,46,49,55,58,279 -- -, chalcones and aurones 227 -, NMR spectrum of 343 -- -, flavones and flavonols 42 -, UV spectra of 110 -- -, isoflavones, flavanones and Ammonia, paper chromatographie spot detection dihydroflavonols 166 12,13,21 Baptigenin 169, 173 Amurensin 40 -, UV spectra of 199 p-Anisidine hydrochloride, spray reagent 27 Baptisia australis 20 Anthochlor pigments 227 - lecontei flavonoids 4,7-10,16-18,30 Anthocyanase 25 Bathochromic shifts (see UV and Detection) Anthocyanins 52 Bayin (see 5-Deoxyvitexin) Apigenin 6, 10, 43, 46, 48, 53, 55, 57, 275 4-Benzyloxy-2,5-dihydroxy- -, NMR spectrum of 280 3,6-dimethoxyacetophenone 28 -, structure of 8 4-Benzyloxy-3,6-dimethoxy- -, UV spectra of 81 2,5-di(5-benzyloxy-3,4-dimethoxy benzoyloxy) - 7-0-glucoside 12, 43, 46, 55, 57, 275 acetophenone 29 - -, NMR spectrum of 282 Biochanin A 14,169,171,173,277 - -, structure of 8 -, NMR spectrum of 314 - -, UV spectra of 82 -, structure of 21 - 7-0-neohesperidoside 43,46, 55, 57, 275 -, UV spectra of 190 - -, NMR spectrum of 281 Boric acid for UV spectroscopy 35 - -, NMR spectrum of sugar 270 B-Ring oxygenation, effect on UV spectrum - -, structure of 269 44,166,227 - -, UV spectra of 83 B-Ring protons (NMR), C-2' and C-6' 265-267 - 7-0-neohesperidoside acetate 275 -- -, C-3' and C-5' 265-267 -- -, NMR spectrum of 281 - 7-0-rhamnoglucoside 4 Calycosin (3', 7-dihydroxy-4' -methoxyisoflavone) - -, structure of 8 6, 14 Arabinose identification 32 - -, structure of 9 A-Ring oxygenation, effect on UV spectra - 7-0-glucoside 7 44,45,46 - -, structure of 9 346 Subject Index Calycosin 7-0-rhamnoglucoside 7 C-Glycosides, NMR 267,269,271 - -, structure of 9 -, paper chromatography 11, 12 Carbon tetrachloride (NMR) 255, 267 Circular dichroism 28, 30 2-Carboxy-5,7-dihydroxyisoflavone 169, 171, 173 C-Methyl protons (NMR) 272 -, UV spectra of 178 Column chromatography 2-Carbethoxy-5, 7-dihydroxy-4'-methoxy- - -, aglycones 19 6-methylisoflavone 278 - -,general 17 -, NMR spectrum of(CCI4) 318 Complexes - AICl3/flavones and flavonols -, NMR spectrum of(CDCI3) 319 51 2-Carbethoxy-5,7 -dihydroxy-4' -methoxy- Cotton efTect 30 8-methylisoflavone 277 Coumarins 18 -, NMR spectrum of (CCI4) 317 Coupling constants (see proton of interest under -, NMR spectrum of(CDCI3) 318 chemical shift) 2-Carboxy-6,7-dihydroxy-4'-methoxyisoflavone C-Ring protons (NMR) 267 169, 173 -- -, IX- and ß-protons (chalcones) 267 -, UV spectra of 194 -- -, benzylic protons (aurones) 267 8-Carbomethoxy-5-hydroxy-6-methylisoflavone -- -, C-2, C-3 262, 267 277 Cytisoside 263,275 -, NMR spectrum of(CDCI3) 310 -, NMR spectrum of 284 -, NMR spectrum of (DMSO-d6) 311 C. A. T. (see time-averaging computer) Daidzein 6, 9, 166, 169, 173 Celite 17, 18 -, structure of 21 Cellulose, column chromatography 17 -, UV spectra of 179 -, thin-Iayer chromatography 21, 22 - 7-0-glucoside (Daidzin) 7, 173 Centaurein 42, 56, 59, 277 -- -, structure of 9 -, NMR spectrum of 307 -- -, UV spectra of 180 -, UV spectra of 150 - 7-0-rhamnoglucoside 7 Chalcones, NMR spectra index 274 - -, structure of 9 -, -- interpretation 254-272 Degradation technique 28 -, numbering system 13, 227 Demethoxysudachitin 21,275 -, paper chromatography 13 -, NMR spectrum of 290 -, thin-Iayer chromatography 22 -, structure of 19 -, UV spectra index 230 Demethylation, selective 29 -, -- interpretation 227-230 5-Deoxy-flavonoids, NMR spectra 264-265 Chalcone 40 -, relative Rfvalues 10 - IX,ß-epoxide 279 -, UV spectra 44,53,56,166,169 - -, NMR spectrum of 339 5-Deoxyvitexin (Bayin) 43, 46, 48, 53, 57 Charcoal 16 - -, UV spectra of 72 Chelation 50 Desalting 32 Chemical shifts, IX and ß-protons (chalcones) 267 Detection (UV) of, 3,4'-dihydroxyl system 47, - -, acetylated C-glycosides 271 167 - -, benzylic protons (aurones) 267 -- 6,7-dioxygenated isoflavones 166 - -, C-methyl protons 272 -- ortho-dihydroxyl groups 50,52,169-171, - -, C-2 protons 267 228 - -, C-2' and C-6' protons 265-267 -- 3,3',4'-trihydroxyl system 47,50 - -, C-3 protons 262, 267 -- 5,6,7; 5,7,8; and 3',4',5'-trihydroxyl systems - -, C-3' and C-5' protons 265-267 47,50,168-170,228,229 - -, C-5 protons 264 -- offree hydroxyl groups, 3-hydroxyl 45, - -, C-6 and C-8 protons 261-265 48,52-55 - -, downfield on acetylation 31,45 ---- -, 4-hydroxyl 228 - -, hydroxyl protons 254 ---- -,5-hydroxyl 52-55,169-172 - -, methoxyl and acetoxyl protons 271 ---- -,6-hydroxyl 51,52,169,170, - -, solvent induced 267, 272 228 - -, sugar protons 268 ---- -,7-hydroxyl 48,51,169 - -,table of 260 ---- -, 8-hydroxyl 51, 52, 169 - -, TMS ether protons 272 ---- -, 2'-hydI:oxyl 229 Chlorophyll, removal 19 ---- -,3'-hydroxyl 50,169 Chromatography cabinet 4, 5 ---- -,4'-hydroxyl 45,48-50,169, Chrysin 43, 48, 55, 57 228 -, UV spectra of 68 Determination of Rfvalues 9 Chrysoeriol 43, 46, 49, 55, 58 De-trimethylsilylation 258, 259 -, UV spectra of 101 Deuteriochloroform solvent (NMR) 254, 267 C-Glycosides, identification of sugar 31' Deuteriodimethyl sulfoxide solvent (NMR) - in Lemna minor 12 254-267 - isomerization 11, 24 Diaxial protons 267,268 Subject Index 347 Diazomethane 30, 259 4',7-Dihydroxyflavone 7-0-rhamnoglucoside, 5',7-Dibenzyloxy-3',4',5,6,8-pentamethoxyflavone -, structure of 8 28,29 -, UV spectra of 71 5' -7-Dibenzyloxy-6-(5-benzyloxy- 2',4' -Dihydroxy-3,4-dimethoxychalcone 279 3,4-dimethoxybenzoyloxy)-3',4',5,8-tetra­ -, NMR spectrum of 337 methoxyflavone 29 5,7 -Dihydroxy-3',4' -dimethoxyflavanone 278 Diequatorial protons· 269 -, NMR spectrum of 334 4',7-Di-O-ethylvitexin 40 5,7-Dihydroxy-3',4'-dimethoxyflavone 43,49, Diglycosides, column chromatography 17, 20 55,58,275 -, distinction from tri- and mono- 27 -, NMR spectrum of 287 -, hydrolysis 24 -, UV spectra of 104 -, NMR 269, 271 5,7-Dihydroxyisoflavone 166, 169, 171, 173 -, paper chromatography 7, 10, 11 -, UV spectra of 176 -, thin-Iayer chromatography 20-22 2' ,4-Dihydroxy-4' -methoxychalcone 279 Dihydrofisetin 170, 174, 278 -, NMR spectrum of 335 -, NMR spectrum of 326 5,7-Dihydroxy-2'-methoxyflavone 43,48,55, -, UV spectra of 220 58,275 Dihydroflavonols, absolute configuration 28, -, NMR spectrum of 284 30 -, UV spectra of 92 -, column chromatography 17-20 3', 7-Dihydroxy-4' -methoxyisoflavone -, 3-0-glucosides 30 (see Calycosin) -, NMR spectra index 274 5,7-Dihydroxy-4' -methoxyisoflavone -, -- interpretation 254-272 (see Biochanin A) -, paper chromatography 13 6,7 -Dihydroxy-4' -methoxyisoflavone -, thin-Iayer chromatography 20-22 (see T exasin) -, UV spectra index 173 4',7-Dihydroxy-5-methoxyisoflavone 40 -, -- interpretation 165-173 5,7 -Dihydroxy-4' -methoxy-8-methylisofla vone Dihydrokaempferol 40, 172, 174, 278 277 -, NMR spectrum of 325 -, NMR spectrum of 316 -, UV spectra of 222 5,7-Dihydroxy-3' ,4' ,5' -trimethoxyfla vone 43, Dihydroquercetin 278 49, 55, 58 -, NMR spectrum of 327 -, UV spectra of 106 Dihydrorobinetin 170, 174, 278 3',5-Dihydroxy-3,4',7,8-tetramethoxyflavone 258 -, NMR spectrum 328 4,4'-Dimethoxychalcone 279 -, UV spectra of 226 -, NMR spectrum of 335 3',4'-Dihydroxyaurone 40,229,230 3',4'-Dimethoxyflavone 43,57 -, UV spectra of 243 -, UV spectra of 67 4',7-Dihydroxyaurone 279 3,4-Di-O-methylgallic acid 28 -, NMR spectrum of 340 5,7-Dimethoxyisoflavone 173 5,7-Dihydroxyaurone 227,230 -, UV spectra of 176 -, UV spectra of 244 5,7 -Dimethoxy-8-methylisoflavone 277 6,7-Dihydroxyaurone 227,229,230 -, NMR spectrum of 313 -, UV spectra of 245 Dimethyl sulfate 30, 259 2,2'-Dihydroxychalcone 229,230 Diosmetin 40, 43, 49, 55, 58, 275 -, UV spectra of 235 -, NMR spectrum of 287 2',4-Dihydroxychalcone 229,230 -, UV spectra of 103 -, UV spectra of 236 - 7-0-rutinoside (see Diosmin) 3,4-Dihydroxychalcone 229,230 - triacetate, structure of 45 -, UV spectra of 234 Diosmin 270,271,275 (+ )-4',7-Dihydroxy-dihydroflavonol 7 -, NMR spectrum of 288 -, structure of 8 -, structure of 269 4',7-Dihydroxyflavonol 6 - acetate 275 -, structure of 8 - -, NMR spectrum of 288 5,7-Dihydroxyflavanone (see also pinocembrin) Distinguishing, 6-C- and 8-C-glycosides 11, 12, 40,45 263 2',3-Dihydroxyflavone 40 -, 6-C- and 8-C-methyl groups 272 3',4'-Dihydroxyflavone 40,43,46,50,57 -, neohesperidosides and rutinosides 269 -, UV spectra of 66 -, C-2 protons 269 4',7-Dihydroxyflavone 6,43,46,48,57 -, C-3, C-6 and C-8