Flavonoids - Markham Harborne Mabry, 1975, (1218 pages)

tổng quan về Flavonoids - Markham, Harborne, Mabry, 1975

The Flavonoids The Flavonoids Edited by J B HARBORNE Reader In Phytochemlstry University of Reading, U.K T J MABRY Professor and HELGA MABRY Research Assistant, Department of Botany University of Texas at Austin, U.S.A Springer-Science+Business Media, B.Y © Springer Science+Business Media Dordrecht Originally published by Chapman and Hall Ltd in 1975 Softcover reprint ofthe hardcover 1st edition 1975 ISBN 978-0-12-324602-8 ISBN 978-1-4899-2909-9 (eBook) DOI 10.1007/978-1-4899-2909-9 All rights reserved No part of this book may be reprinted, or reproduced or utilized in any form or by any electronic, mechanical or other means, now known or hereafter invented, including photocopying and recording, or in any information storage and retrieval system, without permission in writing from the Publisher Library ofCongress Catalog Card Number 74-12868 Contents page Contributors Preface Introduction T A Geissman Isolation techniques for flavonoids vii x XlI Ken R Markharn Ultraviolet-visible and proton magnetic resonance 45 spectroscopy of tlavonoids Ken R Markharn and Tom J Mabry Mass spectrometry of flavonoids 78 Tom J Mabry and Ken R Markharn Synthesis of flavonoids 127 Hildebert Wagner and Lorand Farkas Anthocyanins 214 C F Timberlake and P Bridle Flavones K Venkataraman Flavonols 267 296 Otto Richard Gottlieb Flavone and flavonol glycosides Jeffrey B Harborne and Christine A Williams Cha1cones, aurones and dihydrocha1cones 376 442 Bruce A Bohm 10 Natural proanthocyanidins E Haslam 505 11 Flavanones and dihydroflavonols 560 Bruce A Bohm v CONTENTS vi 12 C-Glycosylflavonoids J Chopin and M L Bouillant 632 13 Biflavonoids Hans Geiger and Christopher Quinn 692 14 743 Isoflavonoids E Wong 15 Neoflavanoids Dervilla M X Donnelly 801 16 Biosynthesis of flavonoids Klaus Hahlbrock and Hans Grisebach 866 17 Metabolism of flavonoids Wolfgang Barz and Wolfgang Hösel 916 18 Physiology and functions of flavonoids Jerry W McClure 970 19 Biochemical systematics of flavonoids J B Harborne 1056 20 Evolution of flavonoid compounds T Swain 1096 Addenda 1130 Author Index 1139 Plant Species Index 1177 Subject Index 1197 Contributors W BARZ Lehrstuhl für Biochemie der Pflanzen, Westfälische-WilhelmsUniversität, 44 Münster/Westf Hindenburgplatz 55, Germany B A BOHM Department of Botany, University of British Columbia, Vancouver, Canada M L BOUILLANT Laboratory of Biological Chemistry, University of Lyon, 69 Villeurbanne, France P BRIDLE Long Ashton Research Station, University of Bristol, U.K J CHOPIN Laboratory of Biological Chemistry, University of Lyon, 69 Villeurbanne, France DERVILLA M X: DONNELLY Chemistry Department, University College, Belfield, Dublin 4, Ireland L FARKAS Institut für Pharmazeutische Arzeimittelehre, 8-München-2, Karlstrasse 29, Germany H GEIGER 1, Universität Fachgruppe Hohenheim, D-7000-Stuttgart70, Windhalmweg 14, Germany T A GEISSMAN Department of Chemistry, University of California, Los Angeles, U.S.A vii viii CONTRIBUTORS O R GOTTLlEB Instituto de Quimica, Universidade de Sao Paulo, Brazil H GRISEBACH Biologisches Institut 11 der Universität, Schänzlestr 9-11, D-7800 Freiburg/Br., Germany H HAHLBROCK Biologisches Institut 11 der Universität, Schänzlestr 9-11, D-7800 Freiburg/Br., Germany J B HARBORNE Plant Sciences Laboratories, The University, Reading, U.K E HASLAM Department of Chemistry, The University, Sheffield, U.K W HÖSEL Lehrstuhl für Biochemie der Pflanzen, Westfälische-WilhelmsUniversität, 44 Münster/Westf., Hindenburgplatz 55, Germany T J MABRY The Cell Research Institute and Department of Botany, University of Texas at Austin, Texas 78712, U.S.A K R MARKHAM Chemistry Division, Petone, New Zealand McCLURE Department of Botany, Miami University, Oxford, Ohio, U.S.A C QUINN School of Botany, University of New South Wales, Kensington, NSW 2033, Australia T SWAIN Biochemical Laboratory, Royal Botanic Gardens, Kew, Surrey, U.K C F TIMBERLAKE Long Ashton Research Station, University of Bristol, Bristol, U.K D.S.I.R., CONTRIBUTORS ix K VENKATARAMAN National Chemical Laboratory, Poona 8, India H WAGNER Institut für Pharmazeutische Arzeimittelhre, 8-München-2, Kar1strasse 29, Germany CHRISTINE A WILLIAMS Plant Sciences Laboratories, The University, Reading, U.K E WONG Applied Biochemistry Division, D.S.I.R., Palmerston North, New Zealand Preface The flavonoids, one of the most numerous and widespread groups of natural constituents, are important to man not only because they contribute to plant colour but also because many members (e.g coumestrol, phloridzin, rotenone) are physiologically active Nearly two thousand substances have been described and as a group they are universally distributed among vascular plants Although the anthocyanins have an undisputed function as plant pigments, the raison d'etre for the more widely distributed colourless flavones and flavonols still remains a mystery It is perhaps the challenge of discovering these yet undisc10sed functions which has caused the considerable resurgence of interest in flavonoids during the last decade This book attempts to summarize progress that has been made in the study of these constituents since the first comprehensive monograph on the chemistry of the flavonoid compounds was published, under the editorship of T A Geissman, in 1962 The present volume is divided into three parts The first section (Chapters 1-4) deals with advances in chemistry, the main emphasis being on spectral techniques to take into account the re cent successful applications of NMR and mass spectral measurements to structural identifications Recent developments in isolation techniques and in synthesis are also covered in this section Advances in chemical knowledge of individual c1asses of flavonoid are mentioned inter aha in later chapters of the book The main section of the volume (Chapters 5-15) is concemed with providing a comprehensive account of the known structural variation among the fifteen c1asses of flavonoid compound The need for a modem listing of all the known flavonoids has become more and more acute since so many new substances have been reported in re cent years Although the various contributors in this section have interpreted their tasks in different ways, this part of the book should 1190 THE FLA VONOIDS Olea 411, 450 europaea 247,380,411,463, 1003 Oleaceae 247 Olearia nummularifolia 324 Onagraceae 243 Ononis spinosa 757 Onopordum acanthium 274 Ophioglossum 1113 vulgatum 327, 422 Opopanax 638 Opuntia lindheimerii 431 Orchidaceae 254 Orchis 254 Oreodoxa regia 415, 421 Orlaya 1068 Ormosia excelsa 748 Orobanchaceae 1064 Orobanche 1064 arenaria 1064 ramosa 1064 Oroxylum indicum 70, 412 Orthantha lutea 409, 423 Oryza 412, 640 sativa 996, 998 Oryzias latipes 1036 Osmanthus 411 Osmundaceae 1102 Ougeinia dalbergioides 760 Ouratea 541, 542, 552 Ovidia pillopillo 271, 406, 408, 409 Oxalidaceae 444, 485, 637 Oxalis 468, 469, 471, 637 cernua 471, 485 ortgiesii 1008 Pachyrrhizus erosus 749, 760, 763, 782 Paeonia 447 albiflora 41 decora 414 trollioides 482 Palmae 411, 552, 640, 1063, 1064 Panax ginseng 414 Papaver 397, 1060 samniferum 234 Papaveraceae 230, 234, 1060 Paraboea cordata 251 Parkinsania 637 aculeata 646, 655-657 Parthenium tomentosum 334 Parthenocissus tricuspidata 241, 1023 Passiflora 638, 660 quadrangularis 242 Passifloraceae 242, 638 Pastinaca sativa 423, 1001 Pectinophora gossypiella 1031 Pedaliaceae 1061 Pedalium 1061 murex 405, 409, 410 Pelargonium hortense 990 Peltophorum 564, 574 inermis 604 Penicillium 948 Pentachondra ericaefolia 245 Pericopsis 747, 748, 787 angolensis 768 Perilla 1018 nankinensis 248 ocymoides 974 Perityle vaseyi 333 Persea gratissima 544 Persica vulgaris 61 Petrocoma hoefftiana 662 Petrocosmea 469 kerrii 485 Petroselinum crispum 396,401, 404, 405, 408,409,421,875,877,880, 886-895,927,973,975,976,986 Petunia 400,415,416,421, 586 hybrida 248, 461, 607, 870, 877, 879, 924,932,975,981,990,997 Peumus boldus 328, 423 Phalaris arundinacea 253 Phallus impudicus 493, 494, ll06-1108 Pharbitis nil 24 Phasealus 418 aureus 238, 782, 881, 884-887, 901, 902,906-908,927,935,938,946, 997, 1003 vulgaris 238,414, 427, 759, 760, 776, 779,883,901,938,975,977,999, 1001,1004,1024,1025,1028 Phellodendron 585, 589, 618 amurense 325, 346, 589, 590, 606 chinense 325 japonicum 325 lavallei 325, 590, 606 pyriforme 325 sachalinense 325, 346, 590, 606 Philanthelium deusturn 486 Phleum pratense 423 Phlox 639, 1086 drummondii 644, 646, 651, 655, 661, 664,668,1086 Phyllocladus 231 aspleniifolius 231 Phyllodoce 1076 empetriformis 328 Phyllogeiton 474 zeyheri 473, 726, 734, 736 Phytolacca americana 230, 420 dioica 330, 424 Phytophthora megasperma 999 Picea 231,619 abies 930 sitchensis 30 Pieris 494, 497 floribunda 497 japonica 245, 497 Pilgerodendran 61 uviferum 608 Pinaceae 230, 231, 478, 608, 619, 635, 736, ll01, 1114, ll23 Pinguicula vulgaris 72 Pinus 231, 269,445, 563, 570, 582, 583, INDEX OF PLANT SPECIES 587,599,609,619, 1057, 1058, 1071, 1072 cembra 569 excelsa 324, 452, 478 gri[[ithii 324 kremp[ii 570,619 ponderosa 326 radiata 1005 strobus 276 Mper445,447,452,563,570,605,640 methysticum 458, 482 peepuloides 71 Piperaceae 482, 605, 640 Mscidia erythrina 750, 763, 766, 788 Mstacia 586, 618 chinensis 347, 600 Msum 416,421,979 sativum 27,238,415,416,420,421, 774,873,924,938,975,978-980, 982,985,990,994,996-999,1001, 1003, 1004, 1019-1023, 1025, 1027, 1029 Mtyrogramma 445, 447, 476, 493, 494, 496 calomeianos457,477,478, 1006 chrysoconica 14, 324, 477 chrysophylia 452,457,477,478, 1113 tartarea 325, 1006 trianguiaris 453, 476, 478, 1083 Plantaginaceae 1061 Plantaga 407, 1061, 1089 asiatica 173, 405 major 270 maritima 409, 1090 Platanaceae 60 Piatanus 583-585 Plathymenia 448, 568, 579 reticuiata 461, 481, 604 Piatycodon grandi[lorum 25 I Piatymiscium 445, 563, 564, 572, 583 praecox 346,481,491, 582,604, 748 trinitatis 768 Plectranthus marrubioides 336 Plumbagelia micrantha 246 Plumbaginaceae 246, 482, 485, 638, 1058, 1071-1073, 1087 P/umbago 1079 capensis 246, 328, 1063 coerulea 246 europea 246, 331,428 pulchel/a 246, 328 rosea 246 scandens 328 zeyianica 328 Plumeria acuminata 247 rubra 247 Plummera ambigens 334 [loribunda 422 Podocarpaceae 230,231,609, 619,724, 732, 746, 1101, 1102 Podocarpus 231,619,732 chinensis 724 1191 [a lcatus 71 gracilior 724 lawrencii 231 macrophyllus 724 montanus 724 nagi 724 spicatus 609,747,749,1114 taxifolius 724 Poecilanthe 565, 574 parvi[lora 604, 749, 760 Pogonia japonica 254 Poinsettia 239 Polemoniaceae 639, 1061 Polygonaceae 230, 232, 635, 1061 Polygonum 635, 1061 avicuiare 395, 419 hydropiper 328, 329, 401, 424 orientale 645, 654, 655 polystachyum 419 recumbens 417 thunbergii 328 Polypodiaceae 478, 1101 Polypodium vulgare 55 Polyporus versicolor 952 Polystichum 1113 Poncirus tri[oliata 61 Pongamia g/abra 280, 347, 348 pinnata 285 Pontederia crassipes 1008 Pontederiaceae 252 Populus 269, 494, 496, 563, 584, 586 alba 606 balsamifera 493 deltoides 592, 606 nigra 280, 324, 325, 328, 572, 606, 1006 yunnanensis 399, 416 Pore/la 635 platyphylla 65 3, 660 Paria weirii 76 Potamogeton 640 natans 647, 657 Potamogetonaceae 640 Potentil/a 1069 reptans 421 Poupartia 618 axillaris 600 Primula 246, 268, 269, 397, 584, 1060, 1067, 1072, 1079 acaulis 269 algida 415 alpicola 338 clarkei 246 [lorindae 268, 271 imperialis 269 malacoides 71 modesta 269 rosea 246 sinensis 269,398,414,415,420,421, 428, 605 vulgaris 340, 355, 426 waltonii 71 1192 THE FLA VONOIDS Primulaceae 246, 605, 1006, 1060, 1072 Prosapis 1061,1087 alba 1089 chilensis 1089 reptans 1089 spicigera 333, 425 Proteus vulgaris 1032 Prunus 236, 269, 563-567, 569, 573, 574, 583,584,588,591, 599,605,758, 923 aequinoctialis 412, 610 avium 235,332,335,570, 610, 1000 campanulata 610 cerasus 235,236, 563, 570,610 communis 584,610 cornuta 610 domestica 235, 338,610,929 donartium 610 jamasakura 610 lanne siana 61 mahaleb 610 maximowiczii 610 mume 326,584,588,610 nippon 326 nipponica 610 persica 236, 580,610, 1000, 1022 pseudocerasus 610 puddum406,457,482, 586,610,748, 756, 760 serotina 610 serrata 406, 610 serratula 610 speciosa 61 o spinosa 414,415,418,610 spinulosa 610 succedanea 236 ssiori 610 verecunda 610 vu lgaris yedoensis 610 Pseudomonas 952, 953 Pseudorlaya 1068 pumila 411,431 Pseudotsuga 231,565, 568,619 menziesii 576, 609, 1005 japonica 609 taxifolia 609 Psiadia altissima 60 Psidium guaijava 419 Psilotum 1100, 1102, 1111, 1113, 1123 triquetrum 721, 728, 1111 Psoralea 446, 566, 637, 650, 653, 656, 657, 660, 662-665 corylifolia 456,481, 572,604,782 Psylliostachys suvorovii 246 Ptaeroxylon obliquum 344, 356 Pteridaceae 635 Pteridium aquilinum 400 Pterocarpus 445, 747, 768, 769 ango/ensis 748, 749, 787 dalbergioides 481, 747, 769 erinaceus 747, 787 indicus 481, 787, 1083 macrocarpus 481 osum 748 santalinus 481, 748 Pterodon apparicioi 748 pubescens 748, 749 Pterospermum acerifolium 326 Pti/anthelium 468 Pueraria 418, 637, 747, 757 thunbergiana 647, 658, 665 tuberosa 658, 665, 757 Pulicaria dysenterica 335 Pullularia fermentans 950 Punicum granatum 743 Punicaceae 243 Putranjiva roxburghii 726, 734 Pyrus 407,409,447,497, 1072, 1079, 1088, 1090 communis 235, 411, 423 Quercus 552 incana 419 peduncu/ata 873, 1008 tinctoria 41 Quintinnia 86 serrata 606 Ranunculaceae 232, 426, 482, 636, I 060 Ranunculus 636, 1060 /ingua 664 Raphanus sativus 234 Reaumuria palastenia I 010 Reboulia 635 hemispherica 396, 406, 645, 654, 663, I II Rechsteineria macrorhiza 50 Remirea 468, 568 maritima 486, 582, 607 Reseda lutea 271 luteola 408 Restio 252, I 060 Restionaceae 252, I 060 Reticulitermes flavipes 848 Reynoutria japonica 419 Rhabdothamnus so/andri 250 Rhamnaceae 726, 737 Rhamnus 424 alaternus 416 cathartica 325, 328, 329, 417, 422 dahurica 325, 328, 329 erythroxylon 325, 328, 329 frangula 325, 328, 329 Rheum rhaponticum 232 tataricum 232 Rhizoctonia solani 1025 Rhododendron 245, 325, 328, 329, 331, 380,431,566,584,586 ,587,601, 618,619, 1060, 1072, 1075, 1076, 1088 INDEX OF PLANT SPECIES calostrotum 1063 catawbiense 331 dauricum 327 farrerae 60 formosum 601 grande 601 japonicum 3 kaempferi 601 mucronatum 327, 422 obtusum 327, 331, 428 racemosum 325, 416 russatum 416 simiarum 601 simsii 245, 428, 601 Rhodothamnus 1076 chamaecistus 325 Rhodotypos kerrioides 424 Rhus346,447,459,468,470,477,585, 586,618 coriaria 39 cotinus 484, 600 glabra 600 javanica 346, 478, 484, 600 semialata 1024 succedanea 346, 404, 429, 600, 724, 734 tricocarpa 600 vernicifera 600 Rhynchotechum parviflorum 250 Rhytidophyl/um tomentosum 250 Ribes nigrum 234 Ricinocarpus muricatus 150, 339, 340 stylosus 148, 331, 339, 340 Ricinuscommunis 1008,1018 Robinia 445, 448, 465, 587 pseudacacia 270,415,418, 490, 511, 552,594,604,870 Rodgersia podophylla 235 Rosa 237 multiflora 237, 1003 rugosa 996, 1000 spinosissima Rosaceae 235, 426, 482, 605, 636, 746, 1061, 1063 Rosmarinus officinalis 273 Rottlera 450 tinctoria 454, 479 Rubiaceae 247, 605, 810, 1061 Rubus 236, 237 fruticosus idaeus 236 loganobaccus 237 occidentalis 237 Rudbeckia hirta 333,334,425, 1017 Rumex 635 crispus 232, 986, 990 hydrolapathum 986 sanguineus 986 thyrsiflorus 232 Rungia repens 398, 414, 446, 477, 478 Ruta graveolens 420, 941 1193 Rutaceae 239, 272, 277, 482, 605, 618, 637, 1060 Sabina chinensis 72 sargentii 723 Saccharum 1023 officinarum 402, 412, 413 Sagittaria 639 Salicaceae 232, 482, 606 Salix 232, 446, 564, 574, 1023 acutifolia 457, 482, 606 amygdalina 232 alba 424 arbuscula 427 bakko 408 caesia 408 caprea 409, 53 daphnoides 232, 457 elburzensis 457 purpurea 181, 216,232,457,482,606 Salmonella enteritidis 1013, 1032 typhosa 1032 Salvia horminum 248 o fficinalis splendens 248 triloba 272 Sanguisorba officinalis 237 Santalaceae 606 Sambucus 1068 Saponaria 636 officinalis 660 Sapotaceae 606 Sargentia greggii 269, 272 Sarothamnus scoparius 646, 657 Sarmienta repens 250 Satureja douglasii 74 Saxifragaceae 234, 606, 1059 Scabiosa 639, 660 japonica 251 Schinopsis 468, 470, 473, 474, 477, 585, 587, 618 Schizandraceae 233 Schizeilema 1091 Schoenus 468 apogon 498 Sciadopitys 733 verticillata 24 Scirpus 468 nodosus 468 Scrophu/aria 1061 grossheimii 232 Scrophulariaceae 249, 444, 487, 488, 607, 639, 1061 Secale cereale 253, 975 Sedum acre 1060 album 338, 567, 934, 987, 1060 altissimum 601 sexangulare 338, 354, 417 THE FLA VONOIDS 1194 Selaginella 14, 1112, 1122 nipponica 721 pachystachys 721 tamariscina 721, 728 Selinum 565 vaginaturn 575, 607 Semecorpus anacardium 726, 734 Senecio 639, 650, 653, 1088 radicans 327 Serratula 725 Sesamum 1061 indicum 273, 410 Sesuvium portulacastrum 332 Sequoia 619, 733 gigantea 609 sempervirens 724 Sequoiadendran 732 giganteum 724 Shigella paradysenteriae 1032 Silene 636 conica 653 hoefftiana 662 schafta 650, 653 Silybum 587, 593 marianum 593, 601, 987 Simaroubaceae 638 Sinapis 997 alba 931, 943, 975, 980, 981, 996, 1004, 1005 arvensis 427 Skimmia japonica 239 Smilax 494 excelsa 496 glauca 496 glycyphylla 496, 1083 megalantha 496 rotundifolia 496 Solanaceae 248, 426, 607, 1008 Solanum chacoense 1083 melongena 248 nigrum 248 soukupii 428 stoloniferum 1083 tuberosum 248,398,415,416,421, Soymida 587 febri[uga 331, 594, 604 Sparattosperma 563, 569 vernicosum 600 Spartium 637 junceum 10, 407, 408 Spathadia campanulata 249 Spergularia 636 rubra 652, 655 Sphagnum nemoreum 216 Sphenomeris 635 Spinacea oleracea 333-335, 1009, 1028, 1061 Spiraea bumalda 419 ulmaria 419 Spirodela 640, 663 intermedia 253,660,975,983,984, 1003 oligorhiza 660, 902, 975, 989, 991, 994, 995, 1003 polyrhiza 902, 903, 989, 1003 Stachys annua 272, 396, 405 neglecta 270,413 palustris 413 Staehelina 639 dubia 273 Stangerioparadoxa 729 Stapelia 247 Staphyleaceae 240 Staphylococcusaureus 1014, 1032 Stauracanthos 637 Stellaria 636 Sterculia [oetida 242 kunstleri 24 parviflora 242 Sterculiaceae 242, 1060 Stereospermum suaveolens 409, 1061 Stipa 640 lemonii 664 Streptocarpus 487 Stromatopteridaceae 1102 578,581,604 Swartzia leiocalycina 769, 782 madagascariensis 768, 769, 775, 782 Swertia 639, 653 japonica 645, 646, 653, 656 Symphoricarpos 1068 Syntrichopappus 488, 489 Syrenia siliculosa 420 1004, 1008, 1029, 1031 Tabebuia 249 Tagetes 418 erecta 333, 424 patula 333 Taiwania 733 cryptomerioides 724 Talauma 328 Tamarindus 637 Tamarix 401 africana 1008, 1014 wrightii 248 Sophora 269, 446, 448, 450, 462, 566, 568, 572,637,652,655 angusti[olia 325, 456, 462, 481, 490, japonica 414, 757, 769 microphylla 660, 661 Subprostrata 456, 481, 604, 769 Sorbaria 1061 sorbifo lia 40 stellipila 71 Sorbus pendula 41 Sorghum durra 253,271 vulgare 253,874,975, 1001, 1003, INDEX OF PLANT SPECIES aphylla 329 dioica 329 gallica 329 laxa 329 troupii 329, 424 Tanacetum 1077 corymbosum 409 niveum 404 vulgare 406 Taxaceae 724, 1102 Taxodiaceae 609,619,724,732, 1101, 1102 Taxodium 732 distichum 422, 724 mucronatum 724 Taxus baccata 404, 724 cuspidata 724 floriana 724 Teclea 637 Teeoma 1061 austra/is 273 garrocha 249 stans 946 Te/ine 637 Tephrosia 284, 763, 794, 1061 lanceo/ata 285 maxima 747, 748 polystachyoides 284 vogelii 331, 417 Tetracera 328 akara 328 portobellensis 328, 1063 Tetrahymena pyriformis 1018 Teucrium polium 72 Thalictrum 636 rugosum 328, 660 thunbergii 404 Thea 638 sinensis 653, 660, 881 Theaceae 638 The/esperma 488, 489, 1080 simplicifolium 1080 Theobroma cacao 242, 509, 537, 933 Thermopsis 757, 758, 1079, 1080 montana 748 Therorhodion 1076 Thespesia populnea 338 Thevetia nerifolia 329 peruviana 156, 70 Thuja 619 occidentalis 273, 412, 723 orientaUs 608, 723, 731 plicata 231,608,723,731 standishii 72 Thujapsis dolabrata 723, 731 Thunbergia alata 487 grandif/ora 249 mysorensis 487 Tilia 584, 585 1195 argentea 400, 415, 416, 420 japonica 173, 406 platyphyllos 418, 607 Tiliaceae 607 Titanotrichum oldhamii 250 Tithonia tubaeformis 270 Tmesipteris 72 8, 1111 Torilis 407, 1068, 1079 arvensis 432, 1063 Torreya nucifera 724 Toxy/on parniferum 344 Trachy/obium 450 verrucosum 463, 473, 481, 491 Tragapogon 639, 652, 653, 655, 656 dasyrhynchus 408 dubius 660 Trecu/ia africana 344 Trema 635 aspera 654, 663 Tribulus terrestris 416 Trifolium 28, 446, 448, 747, 748, 756-758,782,898,993 ,1069 pratense 358,414,757,768,791, 881, 893, 1003 repens 269,270, 781,782,793,999, 1037 subterraneum 270, 346, 347, 413, 429, 455,459,481,750,791 ,881,988, 989, 993, 1003, 1037 Trig/ochin 640 Trigone/la 637 corniculata 649, 654, 668 foenumgraecum 661 Triostemma 1068 Trip/eurospermum 1077 Triticum 640, 653, 662 aestivum 253, 652, 656, 663 dicoccum 273, 412, 656 monococcum 660, 1063 vulgare 999, 1020, 1022-1024 Tro/lius 636 Tropaeolum majus 975 Tsuga 231,619 heterophyl/a 231,540,609 Tsusiophyllum 1076 Tulipa 415,421,448,461,483 ,900,931, 971 hybrida 1008 Turgenia 1068 /atifolia 404, 411, 431 Typha latifolia 398, 420 U/ex 446, 637 europaeus 420, 455,481 galli 481 nanus 757 Ulmaceae 607, 635 U/mus 1086, 1091 americana 553, 1086 laevis 1086 parvifolia 1086 Umbelliferae 407, 431, 607, 638, 1063, 1067, 1078 1196 THE FLA VONOIDS Uncaria gambir 552 Urginea 586 maritima 607 Uvularia sessi/iflora 1064 Vitaceae 240, 607, 638 Vitex 336, 639, 1061 Vaccaria 636 segetalis 660 Vaccinium 638 corymbosum 245 macrocarpon 245, 428, 986, 1001, 1003 myrtil/us 245 vitis-idaea 245, 532, 543 negundo 336 trifo/ia 336 Vitis 240, 241, 638 cinerea 218, 240 vinifera 28,218,220, 240, 506, 1013 agnus-castus 3 lucens 10, 643, 644, 648, 649, 651-656,661,662,664,666 Valerianaceae 1069 Va/erianella 1061, 1068, 1072, 1088 Vanieria cochinchinensis 344 Venturia inaequalis 948, 1026 Verbenaceae 248, 639, 1061 Verbesina iyricephala 416 Vernonia baldwinii 18 cinerea 327 interior 1084 lindheimeri 1084 patens 327 Veronica 1061 Veronicastrum sibiricum 408 Vestia lycoides 420 Viburnum 494, 496, 734, 1068 davidi 493, 496 prunifo/ium 726 trilobum 51 Vicia faba 1006 Victoria regia 3 Vigna 418 Viguiera 447,448, 468,469, 472, 488, 489 multi[lora 479, 485 Vinca minor 418, 421, 428 Vincetoxicum officinale 419, 420 Viola 420, 428, 638 cornuta 869, 870 tricolor 242, 649, 652, 653, 656 Violaceae 242, 638 Viscum album 408 Webera corymbosa 141, 273 Wedelia calendulaceae 782 Weigelia 1068 decora 251 Wistaria 587, 758 sinensis 540, 604 Wolffia 640, 653 Xanthium pennsylvanicum 334, 944, 987, 991 spinosum 277 Xanthorrhoea 446, 447, 458 austra/is 456, 483 preissii 48 Xanthorrhoeaceae 483 Xanthoxylum 561, 579, 618 acanthopodium 339, 354, 393, 426, 1060 avicennae 606 cuspidatum 606 parvi[lorum 606 Zamia 729 angustifolia 721 Zamiaceae 721, 72 Zea mays 253, 901, 975, 978-990, 999, 1000, 1008, 1024, 1026 Ze/kova 584, 635 serrata 589, 607, 647, 658 Zeyhera tuberculosa 270, 272 Zingiberaceae 483, 607 Subject Index Acacetin glycosides 406 Acetobromsugars preparation of 166 Acetophenones used in flavonoid synthesis 132 Afrormosin 748, 752 glycosides 758 methyl ethers 748 Agathisflavone 730 and derivatives 696, 698 Amentoflavone 728 and derivatives 69 5, 700 mass spectrum of methyl ether 110 Amorphogenin biosynthesis 908, 910 metabolism 940 Anthochlors distribution in the Compositae 489 Anthocyanidins 215, 316 naturally occurring 217 Anthocyanins acylated 218 and flower colour 224 biosynthesis 877, 902, 997 chemistry 220 chromatography 12, 28, 30 classes of 21 dimerization 228 effect of light on accumulation 982 in bryophytes 1109 isolation 219 metabolism 229, 932, 956 natural occurrence 230-254, 1106 new sugars of 216 of gymnosperms 231 of the Archichlamydeae 232-243 of the monocotyledons 252-254 ofthe Sympetalae 245-251 peroxide oxidation 227 physiology 981 quantitative measurement 21 reactions with bisulphate 227 reduction 228 spectra 55, 69 structural changes with pH 223 structure 221 synthesis 165,221 systematics 1072, l 088 Antibiotic effects of flavonoids 1032 Antioxidant properties of flavonoids 1011 Apigenin 270 biosynthesis 891 distribution in Chrysanthemum 1077 glycosides 404-406, 891 mass spectrum 84 metabolism 928 Apigeninidin 217,222 biosynthesis 1004 in the monocotyledons 253 Apiin 404 biosynthesis 897 photocontrol of biosynthesis 973 Apiosyltransferase 897 Apulein 2' -methyl ether mass spectrum 98 Aromatic amino acid metabolism 941 Arthraxin 285 mass spectrum 87 Artocarpetin 278 and related compounds 278, 279 Artocarpin, 79 mass spectrum 86 4-Arylchromans 817,853 acid catalysed transformations 854 biosynthesis 855 3-Arylcoumarins 788 4-Arylcoumarins of the Leguminosae 840 spectra of 841 synthesis 842 3-Aryl-4-hydroxycoumarins alkaline degradation 786 natural occurrence 785 spectra 786 structure 785 synthesis 786, 787 Aspalathin 659 Atanasin 35 Aureusidin 470 Aurones chromatography 28, 30 metabolism 926 natural occurrence 468, 469, 484-486 spectra 51, 108 structure 467 systematics 476 et seq synthesis 179, 183 with one B-ring hydroxyl 467 with three B-ring hydroxyls 472 1198 THE FLA VONOIDS Aurones (Cont.) with two B-ring hydroxyls 470 without B-ring hydroxylation 467 Azaleatin natural occurrence 327, 328, 1062, 1079, 1113 Benzoic acid metabolism 944, 959 decarboxylation 946 demethylation 945 ring fission 945 Bergenin 1116 Betalains, biosynthesis 943 Bifla vonoids chemistry 693-696 chromatography 26, 710-713 countercurrent distribution 713 demethylation of 717 derivatives 713 detection 712 evolution of 735-738 isolation 709 natural occurrence 721-727, 1106, 1111 of angiosperms 726-727, 735-738 of cycads 721 of gymnosperms 722-725, 729-733 of pteridophytes 721, 728 spectra 74, 108-112, 714 structure 697-708, 713 synthesis 159,716-718 systematics 718-735 Bisulphates of flavones and flavonols 402 Brazilin 817, 853, 854 Butein 459 Calophyllic acid 825, 856 Calophyllolide 804, 819, 856 acid hydrolysis 821 alkaHne hydrolysis 820 biosynthesis 910 isomer of 826 Calycopterin 356 Carbohydrates and flavonoid Ievels 991 Caryatin 1062 in Ericaceae 1075, 1076 natural occurrence 329 Catechins see flavan-3-ols Centaureidin 335 as anti-cancer agent 1033 Ceroptin 453, 476 Chalcone-flavanone isomerase 884, 890, 892 chalcones as substrates 885 isoenzymes 886 isolation 884 reaction catalyzed 884 Chalconefflavanone oxidase 894 Chalcone-flavanone synthetase 890, 892 Chalcones as biosynthetic intermediates 878 chromatography 28, 30 incorporation into other flavonoids 880, 881 in ferns 477 metabolism 923, 947 natural occurrence 445 450, 478-483, 1106 spectra 51, 69,105-108 structures 465 synthesis 131, 466 systematics 476, 1075 with no B-ring hydroxyls 444-454 with one B-ring hydroxyl455-458 with three B-ring hydroxyls 463 with two B-ring hydroxyls 458-465 Chaplashin 282 Chemical interconversions of flavonoids 152 alkylation 155, 158 isomerization 52 nuclear oxidation 15 Chemical races of flavonoids in plants 1083 Chlorflavonin 322 Chrysoeriol 271 glycosides 409 Chrysosplenetin 352 Cinnamic acid 4-hydroxylase 873 mechanism of action 874 requirements 874 Cinnamic acids distribution 1107 metabolism 944 Citromitin 580 Classification of plants, 1100 Column chromatography of flavonoids in Baptisia 13 with alumina with cellulose with ion exchange resins 19 with magnesium silicate with polyamide 11 with Sephadex 14 with silica gel Columnidin struct ure of 216 p-Coumarate: CoA ligase 875 purification 875 relation catalyzed 876 Coumarinic acids 818, 856 Cournestans chemistry 780 degradation of 784 metabolism 937 natural occurrence 782 spectra 782 structure 783, 784 Cournestrot 781, 793, 1000 biosynthesis 906 metabolism 936 Cryptocaryone 451, 453 Cupressuflavone 730, 731 and derivatives 696, 699 mass spectrum of methyl ether 109 Cycloartocarpin 280 Cycloheterophyllin 282 SUBJECT INDEX Daidzein 747,751,793 biosynthesis 906 gly cosides 57 metabolism 939, 956 methyl ethers 747 physiology 898 Dalbergin 810 and derivatives 810 Dalbergiones 812, 843 biological properties 848 of the Leguminosae 844 ORD curves 846 spectra 845 stereochemistry 845 synthesis 847 Dalbergiquinols 815, 849 in the Leguminosae 850 ORD curves 852 rearrangements 85 l stereochemistry 85 l synthesis 85 Dihydrochalcones chemistry 492 C-glycosyl 648 in fungi 1107 metabolism 925, 947 natural occurrence 494, 496-497, 1106 structure 493, 496 synthesis 131 systematics 496, 497, 1083 Dihydroflavonols biosynthesis 902, 903 chromatography 16, 17 metabolism 928, 950 natural occurrence 583-587, 600-609, 1106 of gymnosperms 608 of Prunus 610 optical properties 598 spectra SO, 68, 103-105 stereochemistry 594-599 synthesis 146 systematics 1076 with one B-ring hydroxyl 588-590 with three B-ring hydroxyls 594 with two B-ring hydroxyls 591-594 without B-ring hydroxylation 582 Dihydrogossypetin intermediate in catechin degradation 953 Dihydrokaempferol 583, 588 metabolism 928 Dihydromyricetin 586, 594 Dihydroquercetin 585, 591 metabolism 928 ,4' -Dimethylbayin synthesis of 672 Diosmetin 271 glycosides 409 Distribution of flavonoids in plants 1106 Ellagitannins 1116 Enzymeinhibition by flavonoids 1012 1199 Enzymes of general phenylpropanoid metabolism 872 activities effected by light 889 photocontrol of 976 Equol metabolic product 957 Erianthin 351 Eriodictyol 567, 579 Eucomin 855 Eupatoretin as anti-cancer agent 1033 Evolution of angiosperms 1104 of flavonoids 1117, ll of high er plants 110 l of plants 1097 Exostemin 839 Extraction of flavonoids Ficine, 286 Fis