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Thực vật chứa hợp chất phenol
METHODS IN PLANT BIOCHEMISTRY Series Editors P M DEY Department J Plant B of Biochemistry, Royal Η olio way and Bedford HARBORNE Science Laboratories, University of Reading, UK Plant Phenolics: J B H A R B O R N E Carbohydrates: P M D E Y Enzymes of Primary Metabolism: P J LEA New College, UK Methods in Plant Biochemistry Series editors P M D E Y a n d J B HARBORNE Volume Plant Phenolics Edited by J B HARBORNE Plant Science Laboratories University of Reading, UK ACADEMIC PRESS Ηarcourt Brace Jovanovich, Publishers London San Diego N e w York Berkeley Boston Sydney Tokyo Toronto A C A D E M I C PRESS LIMITED 24-28 Oval Road London N W 7DX US edition published by A C A D E M I C PRESS I N C San Diego, CA 92101 Copyright © 1989, by A C A D E M I C PRESS L I M I T E D All Rights Reserved No part of this book may be reproduced in any form, by photostat, microfilm or any other means, without written permission from the publishers This book is printed on acid-free paper @ British Library Cataloguing in Publication Data is available ISBN 0-12-461011-0 Filmset by Bath Typesetting Limited, Bath, Avon Printed by Galliard (Printers) Ltd, Great Yarmouth, Norfolk Contributors D Barron U F R de Pharmacie de Grenoble, Universite Joseph Fourier, 38706-La Tronche, France J J A van den Berg Farmaceutisch Laboratory, Catherijnesingel 60, 3511 G H Utrecht, Netherlands B Bohm University of British Columbia, Vancouver, C a n a d a V6R 1W5 C F Culberson D u k e University, D u r h a m , N o r t h Carolina 27706, USA J A Elix The Australian National University, Canberra A C T 2601, Australia J Gorham School of Plant Sciences, University College of N o r t h Wales, Bangor, Gwynedd, LL57 U W , Wales R J Grayer School of Plant Sciences, University of Reading, Whiteknights, Reading, R G 2AS, U K J B Harborne School of Plant Sciences, University of Reading, Whiteknights, Reading, R G 2AS, U K K Hostettmann Ecole de Pharmacie, Universite Lausanne, Rue Vuillermet 2, C H 1005, Lausanne, Switzerland M Hostettmann Ecole de Pharmacie, Universito Lausanne, Rue Vuillermet 2, C H 1005, Lausanne, Switzerland R Ibrahim Plant Biochemistry Laboratory, Concordia University, Montreal, C a n a d a H G 1M8 R P Labadie Faculty of Pharmacy, University of Utrecht, Catherijnesingel 60, 3511 G H Utrecht, Netherlands K R Markham Chemistry Division, D.S.I.R., Petone, New Zealand B Monties Institut National de la Recherche Agronomique, Laboratoire Chimie Biologique, CBAI, 78850 Thiverval-Grignon, France L J Porter Chemistry Division, D.S.I.R., Petone, New Zealand D Strack Institut fur Pharmazeutische Biologie der Technischen Universitat, O-3300 Braunschweig, Federal Republic of Germany C F Van Sumere Laboratorium voor Plantenbiochemie, Rijksuniversiteit Gent, K.L Kedeganckstraat 35, B-9000 Gent, Belgium C A Williams School of Plant Sciences, University of Reading, Whiteknights, Reading R G 2AS, U K V Wray Gesellschaft fur Biotechnologische Forschung (GBF), D-3300 Braunsch weig, Federal Republic of Germany Preface to the Series Scientific progress hinges on the continual discovery and extension of new laboratory methods and nowhere is this more evident than in the subject of biochemistry The application in recent decades of novel techniques for fractionating cellular constituents, for isolating enzymes, for electrophoretically separating nucleic acids and proteins and for chromatographically identifying the intermediates and products of cellular metab olism has revolutionised our knowledge of the biochemical processes of life While there are many books and series of books on biochemical methods, volumes specifically catering for the plant biochemist have been few and far between This is particularly unfortunate in that the isolation of D N A , enzymes o r metabolites from plant tissues can often pose special problems not encountered by the animal biochemist For a long time, the Springer series Modern Methods in Plant Analysis, which first appeared in the 1950s, provided the only comprehensive guide to experimental tech niques for the investigation of plant metabolism and plant enzymology This series, however, has never been completely updated; a second series has recently appeared but this is organised on a techniques basis and thus does not provide the comprehensive coverage of the first series One of us (JBH) wrote a short guide to modern techniques of plant analysis Phytochemical Methods in 1976 (second edition, 1984) which showed the need for an expanded comprehensive treatment, but which by its very nature could only provide an outline of available methodology The time therefore seemed ripe to us to produce an entirely new multi-volume series on methods of plant biochemical analysis, which would be both thoroughly up-to-date and comprehensive The success of The Biochemistry of Plants, edited by P K Stumpf and Ε E Conn and published by Academic Press, was an added stimulus to produce a complementary series on the methodology of the subject With these thoughts in mind, we planned individual volumes covering: phenolics, carbohydrates, amino acids, pro teins and nucleic acids, terpenoids, nitrogen and sulphur compounds, lipids, membranes and light receptors, enzymes of primary and secondary metabolism, plant molecular biology and biological techniques in plant biochemistry Thus we have tried to cover all the major areas of current endeavour in phytochemistry and plant biochemistry The main aim of the series is t o introduce to the scientist current knowledge of techniques in various fields of biochemically-related topics in plant research It is also intended to present the historical background to each topic, to give experimental details of methods and analyses and appraisal of them, pointing out those methods that are most suitable for immediate application Wherever possible illustrations and structures have been used and one or more case treatments presented The compilation of known χ SERIES PREFACE data and properties, where appropriate, is included in many chapters In addition, the reader is directed to relevant references for further details However, for the sake of clarity and completeness of individual reviews, some overlap between chapters or volumes has been allowed Finally, we extend our warmest thanks to our volume editors for undertaking the important task of organising each volume and cooperating in preparing the contents lists Our special thanks go to the staff of Academic Press and to the many colleagues who have made this project a success P M D E Y J B H A R B O R N E Preface to Volume In spite of the considerable body of current research on the biochemistry of plant polyphenols and of their importance in the agricultural and food industries, no comprehensive treatment of their methodology has yet appeared The need to character ise phenolics on a microscale has been highlighted recently by the discoveries of the roles of particular phenols as signal molecules in crown gall infection, in rhizobial nitrogen fixation, in slime mould differentiation and in pollination mechanisms of Arums Much has been written elsewhere on the chemistry and biochemistry of these substances, and particularly of the flavonoids, but the references to methods of isolation and identification are scattered throughout the literature and the available reviews are limited in their coverage of the many different classes of polyphenol that are now distinguished In the present volume, therefore, an opening chapter is devoted to the detection of phenolic substances in crude plant extracts, the methods required to determine which classes they belong to and the methods available for the quantitative estimation of total phenol The remaining fourteen chapters then outline in turn the procedures available for the extraction, isolation, separation and characterisation of each major class, from simple phenols and phenolic acids through the many flavonoids to xanthones and lichen constituents There are necessary introductions to the chemistry, structural variation, function and distribution of each class and, in a few cases where this is practicable, detailed listings are given of known derivatives Emphasis is given in most chapters to chromatographic separations, and high performance liquid chromatography, because of its increasing importance in phenolic research, receives particular attention However, thin layer and paper Rf values are also included with H P L C retention times, since T L C and PC continue to provide very flexible systems for phenolic identification Ultraviolet spectral techniques for phenolic identification and quantification, which were pioneered during the 1950s, are still widely used and are applicable to all classes of polyphenol However, N M R spectral techniques of ever increasing sophistication are now available for the structural elucidation of novel molecules and the use of N M R spectroscopy is highlighted in almost every chapter In spite of all the advances in spectroscopy, chemical rearrangements, degradations and syntheses still have a part to play in the comprehensive and thorough identification of these plant molecules Biochemical techniques, notably enzymic hydrolyses, also contribute to the characteri sation of those polyphenols which occur naturally in conjugated form In preparing this book for publication, I have been greatly assisted by the enthusiasm XI xii PREFACE TO VOLUME of the contributors and their willingness to keep to a tight time schedule I am grateful to my secretary, Miss Valerie Norris, for her dedicated preparation of my own chapters Finally I owe a debt to the series co-editor, D r Prakash Dey and to D r Andrew Richford of Academic Press for their constant encouragement and wise advice J E F F R E Y B H A R B O R N E General Procedures and Measurement of Total Phenolics J B HARBORNE Plant Science RG6 2AS, I II III IV V VI VII VIII Laboratories, University of Reading, Whiteknights, Reading, UK Historical development T h e range a n d occurrence o f p l a n t phenolics M e t h o d s o f recognising p h e n o l i c s i n p l a n t extracts a n d d e t e r m i n i n g class A C o l o u r tests B C h r o m a t o g r a p h i c procedures C Spectral measurements M e t h o d s o f separation and purification A General B Paper c h r o m a t o g r a p h y C T h i n layer c h r o m a t o g r a p h y D Paper electrophoresis E H i g h p e r f o r m a n c e l i q u i d c h r o m a t o g r a p h y F Large-scale separation Methods o f identification A Spectral procedures B B i o c h e m i c a l procedures C C h e m i c a l procedures Sources o f m a r k e r c o m p o u n d s M e a s u r e m e n t o f t o t a l phenolics Conclusion References 9 10 13 14 14 15 15 16 18 19 20 20 22 23 24 25 26 27 Copyright © 1989 Academic Press Limited All rights of reproduction in any form reserved M E T H O D S IN P L A N T B I O C H E M I S T R Y Vol ISBN 0-12-461011-0 ι I J HISTORICAL Β H A R B O R N E DEVELOPMENT Although many individual phenolic compounds were characterised as natural products during the classical period of organic chemistry, the recognition of phenolics as a discrete group of biogenetically related plant metabolites came in 1957 with the founding in England of the Plant Phenolics G r o u p This was due to the initiative of E C BateSmith, T Swain and their coworkers, following their discovery that such c o m p o u n d s as chlorogenic acid, quercetin, kaempferol and procyanidin were extremely widely distri buted, if not universal, in the vascular plant kingdom While the Plant Phenolics G r o u p expanded during the 1960s into the Phytochemical Society of Europe, French scientists set up a similar organisation "Le Groupe Polyphenols' in 1970 which still operates under this name today The first modern monograph on phenolic compounds (Harborne, 1964) included the following classes of plant phenol: simple phenols, phenolic acids, phenylacetic acids; cinnamic acids, coumarins, isocoumarins and chromones; lignans; 10 groups of flavonoids; lignins; tannins; benzophenones, xanthones and stilbenes; quinones; and betacyanins Although some new classes of phenolic have been discovered since then and other classes have become more numerous and prominent, e.g the lignans, this classification of phenolics based on biosynthetic origin and molecular size will be followed here However, nitrogen-containing phenolics (e.g catecholamines, betalains, etc.) will not be included, but will be covered in this series in the alkaloids volume Many of the basic techniques of phenolic analysis were developed during the first half of the present century- and there- was already, considerable, interest IIL s o m e classes, of natural phenol because of their biological and medicinal properties A series of distribution tests, for example, were developed for the anthocyanin pigments (Robinson and Robinson, 1931), largely because of the genetical interest in these substances The metabolic fate of phenolics in animals was also under active investigation and Bray and Thorpe (1954), in a chapter in Volume of Methods of Biochemical Analysis, reviewed the techniques then available for their detection and identification It was, however, Seikel (1964) who provided the first comprehensive treatment of phenolic analysis, with special emphasis on the roles of paper chromatography and absorption spectro photometry in the characterisation of these natural substances The first book devoted to methods of phenolic analysis was the proceedings of a Plant Phenolics Symposium (Pridham, 1964a) and this included discussion of thin layer chromatography (TLC), polyamide chromatography and paper electrophoresis A n important chapter in that book on quantitative analysis by Swain and Goldstein is still quoted widely today A more recent proceedings of the Phytochemical Society of Europe edited by van Sumere and Lea (1985) also deals in part with methodology The textbook of Ribereau-Gayon (1972) on plant polyphenols also deserves mention for its extensive coverage of phenolic analysis Since those earlier publications, much else has been written on methodology, following the successive introductions of more sophisticated chromatographic (e.g H P L C ) and spectral (e.g carbon-13 N M R ) techniques The writer has provided an introduction to modern methods of phenolic analysis (Harborne, 1984) and also has contributed a regular series of reviews on the chromatography of plant phenols (see e.g in Heftmann, 1983) Books on plant flavonoids have included several valuable contri bution's o n reretti iraifowfofogy {{ferborae attd Msfe-ry, 1982; HarbGrae, 1988) Much 538 INDEX A u r o n e s , 263 c o l o u r tests, 263 c o l o u r s i n U V l i g h t , 263 mass spectroscopy, 266 m e l t i n g p o i n t s , 281 p r o t o n N M R spectroscopy, 265 synthesis, 268 U V spectroscopy, , 281 B i s ( B i b e n z y l s ) , 160 B o e s e n b e r g i n - B , 254 Borntrager reaction o f hydroxyanthraq u i n o n e s , 477 B o r o h y d r i d e / D D Q test f o r d i h y d r o c h a l c o n e s , 292 B o u r g e a n i c a c i d , 512 B r a c t e a t i n , , 266 B u t e i n , 239 B u t i n , , 285, , 305 Β B a k u c h a l c o n e , 250 B a p t i g e n i n , 441 Batatasin I , , 167, 183, 185 Batatasin I I I , , 162, 183, 185 B e l l i d i f o l i n , , , 503 B e n z o q u i n o n e s , , 458 B e r g a p t e n , 78, 88, , 95 B e r g a p t o l , 78, 98 B i b e n z y l - - c a r b o x y l i c acids i n p l a n t s , 177 Bibenzyls, 159, 160 i n higher p l a n t s , 162 B i f l a v o n o i d s , 358 a n a l y t i c a l T L C , 369 c a r b o n - N M R substituent shifts, 383 cellular l o c a l i s a t i o n , 385 concentrations i n Ginkgo biloba leaves, 385 H P L C , 375 i n a n g i o s p e r m s , 363 i n b r y o p h y t e s a n d p t e r i d o p h y t e s , 361 i n g y m n o s p e r m s , 362 i s o l a t i o n , 372 p r o t o n N M R spectroscopy, 380 q u a n t i f i c a t i o n , 385 / ^ - v a l u e s , 377, 378 solvent systems f o r T L C , 367 structures, 358, 359 U V colours o f permethylated biflavones, 371 U V m a x i m a , 380 B i f l o r i d i n , 241 Bi-isoflavans, 425 B i l o b e t i n , 358, 377, 378, , 385 B i o c h a n i n A , 2 , 441 Biogenetic r e l a t i o n s h i p s between g a l l o a n d e l l a g i t a n n i n s , 391 Biosynthesis o f l i g n i n , techniques f o r s t u d y i n g , 139 p h e n o l s , , , 37 p r o a n t h o c y a n i d i n s , 392 q u i n o n e s , 466 xanthones, 494 Biosynthetic pathways to l i c h e n substances, 511 s t i l b e n o i d s , 179 C Caffeic a c i d , , 76, 89, 92 3-glucoside, 24 C a j a g o l , 423 C a p a c i t y factors (kf) o f c i n n a m o y l c o n j u gates, 91 C a p e n s i n i d i n , 328 C a p i l l a r y c o l u m n s u p e r c r i t i c a l fluid c h r o m a t o g r a p h y ( S F C ) o f q u i n o n e s , 482 C a p i l l a r y G L C o f p h e n o l s , 52, 53 C a r p u s i n , , 270 C a s t a l a g i n , , 409 C a s u a r i c t i n , , 409 C a s u a r i i n , , 394 ( # ) - C a t a l p o n o n e , 472 C a t e c h i n , , 398, , 409 ^ / - C a t e c h i n , 399 C a t e c h o l , 3, 30, 32, 38, , 64 C C , see C o l u m n c h r o m a t o g r a p h y C D , see C i r c u l a r d i c h r o i s m C e d e o d a r i n , 306 C e l l cultures a c c u m u l a t i n g q u i n o n e s , 456 C e l l u l a r l o c a l i s a t i o n o f b i f l a v o n o i d s , 385 Centrifugal partition chromatography o f t a n n i n s , 411 C e r u l e n i n , 469 C h a l c o n e s , 237 b r i d g e - o x y g e n a t e d , 259 c a r b o n - N M R spectroscopy, 253 c o l o u r s i n U V l i g h t , 239 c o l o u r tests, 238 d e g r a d a t i o n , 239 mass spectroscopy, 254 m e l t i n g p o i n t s , 275 p r o t o n N M R spectroscopy, 244 synthesis, 257 U V spectroscopy, , 275 Chemical modifications o f plant polyphenols, 23 C h e m o t a x o n o m y o f x a n t h o n e s , 499 Chiroptical properties o f tannins, 412 Chlorflavonin, C h l o r o g e n i c a c i d , 105 539 INDEX C h o r i s m i c a c i d , 472 C h r o m a t o g r a p h i c spray reagents, see reagents Spray C h r o m a t o g r a p h y (see also C C , H P L C , P C and T L C ) o f p o l y p h e n o l i c s , 10 C h r o m a t o t r o n , 299 C h r o m e n o x a n t h o n e , 494 C h r o m o n e s , 78 U V spectra of, 97 C h r y s i n , 199 C h r y s o e r i o l , 199 Chryso-obtusin-2-0-p-D-glucopyranoside, C h r y s o p h a n o l , 454, 468, 480, 482 C i c h o r i i n , 8, 78, 93 C i n c h o n a i n , 401 C i n n a m o y l conjugates c a p a c i t y f a c t o r s , 91 F A B - M S , 106 H P L C , 91 mass s p e c t r o m e t r y of, 105 N M R spectroscopy of, 102 U V spectra, 97 C i n n a m o y l p h e n y l e t h y l glycosides, 106 Circular dichroism ( C D ) absorption spectroscopy o f a n t h o c y a n i n s , 352 t a n n i n s , 412 C i t r o m i t i n , 285 C l a u s s e q u i n o n e , 426 C n i d i l i n , 88, 95 (16S)-Coleone E, 464 Colours in U V light o f aurones, 263 biflavones, p e r m e t h y l a t e d , 371 b i f l a v o n o i d s , 377 chalcones, 239 d i h y d r o c h a l c o n e s , 295 d i h y d r o f l a v o n o l s , 295 flavanones, 294 flavones a n d flavonols, 203 lichen substances, 516 C o l o u r tests f o r aurones, 263 f o r chalcones, 238 f o r flavanoids, 292 f o r l o c a l i s a t i o n o f l i g n i n s , 128 f o r phenolics i n p l a n t extracts, f o r p r o a n t h o c y a n i d i n s , 407 o n lichens, 513 Column chromatography (CC) of a n t h o c y a n i n s , 333 b i f l a v o n o i d s , , 372 flavanoids, 300 flavones a n d flavonols, 206 i s o f l a v a n o i d p h y t o a l e x i n s , , 438 462 Column chromatography (CC) of i s o f l a v o n o i d s , 433 (cont.) p h e n o l s , , 45 t a n n i n s , 411 x a n t h o n e s , 500 C o n d e n s e d t a n n i n s (see also P r o a n t h o c y a n i d i n s ) , 390, 398 C o n f u s o s i d e , 286, 295, 299, 302, 307 C o n i f e r y l a l c o h o l , 117, 119 C o n t o r t i n , 520 C o p p e r - n o r s t i c t i c a c i d - d m f c o m p l e x , 523 C o r a r i i n , 396 C o r n u d e n t a n o n e , 459 - C o u m a r i c a c i d , 76 / - C o u m a r i c a c i d , 76, 89, , 97 C o u m a r i n , 76, 95, 97 C o u m a r i n s , 77 G L C , 90 H P L C , 93-96 M S , 105 N M R spectroscopy, 103, 104 T L C , 85, 87 U V spectra, 97 C o u m a r o n o c h r o m o n e s , 427 C o u m e s t a n s , 424 s k e l e t o n , 426 U V spectra, , 440 C o u m e s t r o l , 424 p - C r e s o l , 30, 32, 38 C r y p t o s t r o b i n , 285 C u p r e s s u f l a v o n e , 359, 360, 377, 379, 380, 384 C y a n i d i n , 328, 332, 347 C y c l o k i e v i t o n e , 423 D D a i d z e i n , 2 , 441 , ' - d i - - g l u c o s i d e , 422 D a i d z i n , 422 D a l p a n i n , 425 D a p h n e t i n , 78, 87, 93 D a p h n i n , 78 D a v i d i g e n i n , 286, 295, 299, 302, 304, 307, 310, 319 D a v i d i o s i d e , 286, 294, 295, 299, 302, 303, 307, 320 D C C C , see D r o p l e t c o u n t e r - c u r r e n t c h r o m a tography Deacetylsessein, 465 - D e c h l o r o - - - m e t h y l t h i o m e l i n , 526 - D e c h l o r o - - - m e t h y l t h i o m e l i n , 526 D e c h l o r o p a n n a r i n , 531 - D e c h l o r o t h i o m e l i n , 526 D e g r a d a t i o n o f chalcones, 239 D e g u e l i n , 425 540 D e h y d r o d u n n i o n e , 473 D e h y d r o r o t e n o n e , 425 D e l p h i n i d i n , 328, 332, 347 D e m e t h y l a t i o n o f flavonoid 231 INDEX m e t h y l ethers, - D e o x y f u e r s t i o n e , 465 - D e o x y j a c a r e u b i n , 499 D e r i v a t i s a t i o n techniques f o r flavonoids, 231 D e r r i o b t u s o n e s A a n d B, 267 D e r r u s n i n , 426 D e s m e t h y l b e l l i d i f o l i n , 496, 503 D e s o r p t i o n chemical i o n i s a t i o n M S ( D C I - M S ) , see M a s s s p e c t r o m e t r y D H N A , see l , - D i h y d r o x y - - n a p h t h o i c acid D i a n t h r o n e s , 456 D i a z o t i s e d s u l p h a n i l i c a c i d , 296 D i c o u m a r o l , 79 D i d y m i n , 288 D i h y d r o b i o c h a n i n A , 423 D i h y d r o c h a l c o n e s , 283 b o r o h y d r i d e / D D Q test, 292 c a r b o n - N M R spectra, 319, 320 c o l o u r reagents, 292 H P L C r e t e n t i o n times, 302 mass spectra, 310 P C p r o p e r t i e s , 295 p r o t o n N M R spectra, 315, 316 structures, 286 T L C , 299 U V spectra, 303, 307 D i h y d r o d a i d z i n , 423 D i h y d r o f i s e t i n , 285, 288, 295 D i h y d r o f l a v o n o l s , 283 c a r b o n - N M R spectra, 319, 320 c o l o u r reagents, 292 mass spectra, 310 P C p r o p e r t i e s , 295 Pacheco's test, 292 Pew's test, 292 p r o t o n N M R spectra, 314 S h i n o d a ' s test, 292 spray reagents, 297 structures, 285 U V spectra, 306 D i h y d r o f o r m o n o n e t i n , 423 D i h y d r o k a e m p f e r o l , 285, 295 D i h y d r o m i l l e t e n o n e m e t h y l ether, 286, 287 D i h y d r o m o r i n , 285 D i h y d r o m y r i c e t i n , 285, 295, 298, 306 , - D i h y d r o p h e n a n t h r e n e s , 159 i n higher p l a n t s , 164 , - D i h y d r o p h e n a n t h r o p y r o n e s i n higher p l a n t s , 165 D i h y d r o q u e r c e t i n , 285, 288, 295, 298 D i h y d r o r o b i n e t i n , 285, 295, 306 D i h y d r o s h i k o n o f u r a n , 459 D i h y d r o s y r i n g e t i n , 285 ' , ' - D i h y d r o x y c h a l c o n e - ' - p r e n y l ether, 249 2',4'-Dihydroxy-3',5'-dimethyl-6'-methoxyc h a l c o n e , 248 , ' - D i h y d r o x y - - m e t h o x y a u r o n e , 238 ' , - D i h y d r o x y - ' - m e t h o x y c h a l c o n e , 238 2',4'-Dihydroxy-3,4-methylenedioxy-6'm e t h o x y c h a l c o n e , 248 ' , ' - D i h y d r o x y - ' - m e t h y l - ,- m e t h o x y c h a l cone, 248 l , - D i h y d r o x y - - n a p h t h o i c acid ( D H N A ) , 472 2,6-Dimethoxy-1,4-benzoquinone ( , - D M B Q ) , 453, 454 / ? - D i m e t h y l a m i n o c i n n a m a l d e h y d e test f o r p r o a n t h o c y a n i d i n s , 407 D i o s m e t i n , 199 D i p l a c o l , 286, 287 D i v a r i c a t i c a c i d , 523, 524 D i v a r o n i c a c i d , 530, 531 , - D M B Q , see , - D i m e t h o x y - , - b e n z o quinone Droplet counter-current chromatography (DCCC) of a n t h o c y a n i n s , 333 b i f l a v o n o i d s , 374 flavones a n d flavonols, 208 p h e n o l s , 45 x a n t h o n e O-glycosides, 501 D u n n i o n e , 473 Ε E c h i n a t i n , 261 E c h i n o f u r a n , 475 E l e c t r o n i m p a c t mass s p e c t r o m e t r y ( E I - M S ) , see M a s s s p e c t r o m e t r y E l e c t r o n p a r a m a g n e t i c spectroscopy ( E P R ) o f phenolics i n c r u d e p l a n t extracts, 14 E l e c t r o p h o r e s i s , see Paper electrophoresis Ellagic a c i d , , 33, 38 E l l a g i t a n n i n s , 391 biogenetic r e l a t i o n s h i p s w i t h g a l l o t a n n i n s , 391 C - O o x i d a t i v e c o u p l i n g i n , 396 e s t i m a t i o n of, 406 E m o d i n , , 454, , , 482 E n g e l i t i n , 285, 295 E n z y m a t i c h y d r o l y s i s o f anthracene g l y c o sides o n T L C , 478 E n z y m a t i c a l l y l i b e r a t e d l i g n i n , 130 E n z y m e s f o r s t r u c t u r a l analysis o f p h e n o l i c s , 22 E p i a f z e l e c h i n , , 398, 409 E p i c a t e c h i n , , 398, 409 INDEX ^ / - E p i c a t e c h i n , 399 E p i g a l l o c a t e c h i n , , 398, 409 E p i p h o r e l l i c acids a n d 2, 524 E P R , see E l e c t r o n p a r a m a g n e t i c spectroscopy E r i c r i s t a g a l l i n , 425 E r i o c i t r i n , 288 E r i o d e r m i n , 528 E r i o d i c t y o l , 285, 288, , 294, 299, 305, 308 E u g e n e t i n , 78 E u g e n i i n , , 397, 409 E u g e n i n , 78 E u r o p i n i d i n , 328 E x t r a c t i o n procedures f o r a n t h o c y a n i n s , 333 b i f l a v o n o i d s , 365 f l a v a n o i d s , 290 flavones a n d f l a v o n o l s , 201 i s o f l a v a n o i d p h y t o a l e x i n s , 437 i s o f l a v o n o i d s , 429 l i g n i n s , 130 phenols, 39 p h e n y l p r o p a n o i d s , 81 q u i n o n e s , 476 stilbenoids, 181 t a n n i n s , 410 x a n t h o n e s , 500 F F A B - M S , see M a s s s p e c t r o m e t r y F a r r e r o l , 285 Fast a t o m b o m b a r d m e n t mass s p e c t r o m e t r y ( F A B - M S ) , see M a s s s p e c t r o m e t r y F D - M S , see F i e l d d e s o r p t i o n mass spectro metry F e r p r e n i n , 79 F e r r i c c h l o r i d e spray reagent, 296 F e r u l e n o l , 78 F e r u l i c a c i d , 8, 76, 89, 92, 97 o - F e r u l i c a c i d , 76 F i e l d d e s o r p t i o n mass s p e c t r o m e t r y ( F D M S ) , 106, 228, 312 F i s e t i n , 199 F i s e t i n i d o l , , 398 F l a v a n o i d s , 283 S h i n o d a test f o r , 292 F l a v a n o n e s , 283 c a r b o n - N M R spectra, 318, 320 c o l o u r reagents, 292 mass spectra, 309 P C p r o p e r t i e s , 294 p r o t o n N M R spectra, 313 S h i n o d a test f o r , 292 spray reagents, 297 structures, 285 U V spectra, 305 541 F l a v o n e - C - g l y c o s i d e s , 204 c a r b o n - N M R s p e c t r o s c o p y , 221 m o b i l i t y o n p a p e r , 204 F l a v o n e s a n d f l a v o n o l s ( i n c l glycosides), 197 a l d i t o l acetate p r e p a r a t i o n , 231 C C , 206 c o l o u r s o n c h r o m a t o g r a m s , 203 D C C C , 207 d e m e t h y l a t i o n , 231 d e r i v a t i s a t i o n , 231 electrophoresis o f sulphates, 209 e x t r a c t i o n , 201 H P L C , 208 m o b i l i t y o f glycosides a n d sulphates, 205 M S , 223 N M R spectroscopy, 213 P C , 201 p e r m e t h y l ether p r e p a r a t i o n , 231 spot c o l o u r i n t e r p r e t a t i o n , 203 sugar analysis, 229 T L C , 205, 206 T M S ether p r e p a r a t i o n , 231 t r i v i a l names, 199 U V spectroscopy, 209 W e s s e l y - M o s e r r e a r r a n g e m e n t , 232 F l a v o n o i d sulphates - d i m e n s i o n a l P C , 205 electrophoresis, 209 F l a v o n o i d s , 197 F l e m i c h a p p a r i n - A , 240, 249 F l e m i s t r i c t i n - B , 249 F l e m i s t r i c t i n - C , 250 F l e m i s t r i c t i n - E , 257 F l e m i s t r i c t i n - F , 250 F l e m i w a l l i c h i n - E , 251 F o l i n - C i o c a l t e u reagent, 10, 25, 26 F o r m o n o n e t i n , 2 , 427, 441 F r a x i n , 78 F r u t i c u l i n A , 464 F r u t i c u l i n B, 465 F u c o f u r o e c k e l , 390 F u m a r p r o t o c e t r a r i c a c i d , 512 F u n c t i o n a l g r o u p analysis o f l i g n i n s , 136 Furanocoumarins G L C , 90 H P L C , 93-96 T L C , 88 U V spectroscopy, 98 F u r a n o x a n t h o n e , 494 F u r f u r i c a c i d , 527 F u s t i n , 285, 305 G G a l a n g i n , 199 542 G a l l i c a c i d , , 33, 38, 56, 64, 390 d e t e r m i n a t i o n of, 406 G a l l o c a t e c h i n , , 398, 409 G a l l o t a n n i n s , , 393 biogenetic r e l a t i o n s h i p s o f w i t h ellagit a n n i n s , 391 C - O o x i d a t i v e c o u p l i n g i n , 396 G a l l o y l ester, 390 d e t e r m i n a t i o n of, 406 G a r b a n z o l , 285, 295, 304, 306 G a r t a n i n , 499 Gas chromatography ( G C ) o f lichen substances, 516 q u i n o n e s , 481 Gas-liquid chromatography ( G L C ) c a p i l l a r y , o f p h e n o l s , 52, 53 o f c o u m a r i n s , 90 o f f u r a n o c o u m a r i n s , 90 o f m a l i c a c i d esters o f p h e n o l i c acids, 89 o f p h e n o l s , 50 o f s t i l b e n o i d s , 183 q u a n t i t a t i v e , o f p h e n o l s , 54 r e t e n t i o n times, o f p h e n o l s , 51 G C , see G a s c h r o m a t o g r a p h y G e n i s t e i n , 2 , 427, 441 , ' - d i - - g l u c o s i d e , 422 G e n i s t i n , 422 G e n t i s i c a c i d , , 33, 59, 64 G e r a n i i n , 397, 409 t a u t o m e r i c f o r m s of, 394 - O - G e r a n y l e m o d i n , 460 G i b b s reagent, 10 G i b b s test f o r chalcones, 239 G i n k g e t i n , 358, 377, 378, 380, 385 G l a b r a c h a l c o n e , 258 G l a b r a n i n , 285 G l a u c o p h a e i c a c i d , 523, 524 G L C , see G a s - l i q u i d c h r o m a t o g r a p h y G l o m e l l i f e r o n i c a c i d , 528 G l o m e l l o n i c a c i d , 528 G l y c e o l l i n I , 446 G l y c o s y l a t i o n , l o c a t i o n o f sites, 242 G l y c y p h y l l i n , 288 G n a p h a l i n , 258 G o s s y p e t i n , 199 G r a y a n i c a c i d , 512 G u a i a c o l , 30, 32, 38 G u a i a c y l l i g n i n , 118 G y r o p h o r i c a c i d , 512 Η H e a v e n l y blue a n t h o c y a n i n , 329 H e r b a c e t i n , 199 INDEX H e r n i a r i n , 87, 93 H e s p e r e t i n , 285, 288, , 299, 305 H e s p e r i d i n , 285, 288, 290, 294 H e x a h y d r o x y d i p h e n i c a c i d , 390 H e x a h y d r o x y d i p h e n o y l ester, 390, 393 H e x a h y d r o x y d i p h e n o y l esters o f D - g l u c o s e , 395 H i g h performance liquid chromatography (HPLC) a p p l i c a t i o n s of, t o h y d r o x y c i n n a m o y l conjugates, 93 c a p a c i t y f a c t o r s (k') o f c i n n a m o y l conjugates, 91 c o l u m n s f o r s e p a r a t i n g a n t h o c y a n i n s , 335 H P L C - U V spectroscopy o f x a n t h o n e s , 502 q u a n t i t a t i v e analysis o f l i c h e n substances, 519-521 r e t e n t i o n times o f b i f l a v o n o i d s , 377 c i n n a m o y l q u i n i c acids, 92 d i h y d r o c h a l c o n e s , 302 h y d r o x y c i n n a m o y l amides, 92 p h e n o l s , 61 separation o f phenols, , 55-59 s e p a r a t i o n o f p i n o s y l v i n a n d its m e t h y l ethers, 184 solvents f o r s e p a r a t i n g a n t h o c y a n i n s , 335 H i g h performance liquid chromatography o f a n t h o c y a n i n s , 333 b i f l a v o n o i d s , 375, 376 c i n n a m o y l conjugates, 91 c i n n a m o y l q u i n i c acids, 92 coumarins, 93-96 f l a v a n o i d s , 301 flavones a n d f l a v o n o l s , 208 furanocoumarins, 93-96 h y d r o x y c i n n a m o y l amides, 92 i s o f l a v a n o i d p h y t o a l e x i n s , 437 i s o f l a v o n o i d s , 436 l i c h e n substances, 517 p h e n o l i c l i c h e n p r o d u c t s , 518 p h e n o l i c s , 18 p y r a n o c o u m a r i n s , 95, 96 q u i n o n e s , 479 s t i l b e n o i d s , 182 t a n n i n s , 411 x a n t h o n e s , 501 H i g h performance T L C ( H P T L C ) for quantitative determination o f quinones, 479 H i n o k i f l a v o n e , 359, 360, 7 - , 383 H i p p u r i c a c i d , 56 H i r s u t i d i n , 328 H i s p i d o l , 268 INDEX 543 H o m o e r i o d i c t y o l , 285, 294 H o m o g e n t i s i c a c i d , 33 I H P L C , see H i g h p e r f o r m a n c e l i q u i d c h r o m a tography H y d r a n g e n o l , 160, , 185 H y d r o l y s a b l e t a n n i n s , 390, 393 h e x a h y d r o x y d i p h e n o y l esters o f D-glucose, 395 N M R spectra, 413 p h e n o l i c h y d r o l y s i s p r o d u c t s f r o m , 403 reactions, 402 relative / ^ - v a l u e s o n - d i m e n s i o n a l P C , 409 structures, 393 tests specific f o r , 406 Hydrolysis o f anthocyanins a c i d , 337 a l k a l i n e , 338 p e r o x i d e , 339 o f flavonoid glycosides, 229 o f q u i n o n e s , e n z y m a t i c o n T L C , 478 H y d r o q u i n o n e , 3, 30, 32, 38, 55, 59, , 64 / ? - H y d r o q u i n o n e , 454 / - H y d r o x y a c e t o p h e n o n e , , 33, 64 - H y d r o x y - a - a c e t o x y r o y l e a n o n e , 465 γ - H y d r o x y a n t h r o n e B, 460 / - H y d r o x y b e n z a l d e h y d e , 31 / ? - H y d r o x y b e n z o i c a c i d , , , 64 - H y d r o x y - - b e n z y l c o u m a r a n - - o n e s , 269 I m p e r a t o r i n , 88, 93, 95, 98 I n f r a r e d ( I R ) spectroscopy o f l i g n i n s , 140 q u i n o n e s , 483 t a n n i n s , 411 I n t e r f e r e n c e m i c r o s c o p y o f l i g n i n s , 129 I n t e r m o n o m e r i c linkages, relative f r e q u e n c y o f mass spectroscopy of, 270 H y d r o x y c i n n a m i c a c i d , 76 H y d r o x y c i n n a m o y l amides c h r o m a t o g r a p h y , 87 H P L C , 92 H y d r o x y c i n n a m o y l c o n j u g a t e s , H P L C o f , 93 H y d r o x y c i n n a m o y l esters c h r o m a t o g r a p h y , 86 M S , 105 N M R spectroscopy, 100 - H y d r o x y c o u m a r i n , 76 - H y d r o x y c y a n i d i n , 328 - H y d r o x y d i h y d r o f l a v o n o l , 285 - H y d r o x y - , ' - d i m e t h o x y f l a v a n , 241 - H y d r o x y d u n n i o n e , 473 ' - H y d r o x y f o r m o n o n e t i n , 428 - - ( - H y d r o x y g e r a n y l ) e m o d i n , 460 - H y d r o x y l u t e o l i n , , ' - t r i m e t h y l ether, c a r b o n - N M R s p e c t r u m o f , 220 / - H y d r o x y p h e n y l a c e t i c a c i d , , 33, 64 - H y d r o x y p h l o r e t i n , 307 ' - H y d r o x y p s o r o s p e r m i n , 497 H y d r o x y s o p h o r a n o n e , 285, 287 2'-Hydroxy-3,4,4',6'-tetramethoxychalcone, 256 H y p o s t i c t i c a c i d , , 532 i n c o n i f e r l i g n i n s , 117, 118 i n b i r c h w o o d l i g n i n s , 118 I R spectroscopy, see I n f r a r e d spectroscopy I r i g e n i n , 2 , 441 I r i s o l i d o n e , 441 I r i s o q u i n , , 483 I r i s t e c t o r i g e n i n A , 422 I s l a n d i c i n , 526 I s o c o r d o i n , 249 I s o d e r r i c i n - B , 250 I s o e u g e n e t i n , 78 I s o f l a v a n o l , 425 I s o f l a v a n o n e s , 423 M S , 442 UV spectra, 439, 440 I s o f l a v a n s , 424 UV spectra, 440 I s o f l a v o n e s , 422 M S , 442 structures, 422 UV spectra, - 4 I s o f l a v o n o i d p h y t o a l e x i n s , 423, 437 C C , 437, 438 e x t r a c t i o n , 437 H P L C , , 438 T L C , 437 I s o f l a v o n o i d s , 421 C C , 434 e x t r a c t i o n , 430 H P L C , 4 , 436 i d e n t i f i c a t i o n , 443 M S , 442 N M R spectroscopy, 443 o l i g o m e r s , 425 p u r i f i c a t i o n , 433 q u a n t i f i c a t i o n , 445 / ^ - v a l u e s o n T L C , 444 s e p a r a t i o n o n silica gel, 434 s t r u c t u r e s , 421 T L C , 435 UV spectra o f d i f f e r e n t classes, 439, 440 I s o f r a x i d i n , 78 I s o g i n k g e t i n , 358, 377, 378, 380, 385 I s o n e o b a v a c h a l c o n e , , 246, 248 I s o - o k a n i n , 285 I s o p i m p i n e l l i n , 78, 88, 93, 95, 98 544 INDEX I s o r h a m n e t i n , 199 I s o s a k u r a n e t i n , 285, 288, 299, 305 I s o s a l i p u r p o s i d e , 240 I s o s c o p o l e t i n , 87 I s o u v a r e t i n , 288 I s o v i c a n i c i n , 531 J J a c a r e u b i n , 499 J u g l o n e , 476 Κ K a e m p f e r o l , 199 K a y a f l a v o n e , 358, 377, 378, 380 K h e l l i n , 78 K l a s o n l i g n i n , 124, 131 K l a s o n - t y p e p r o c e d u r e f o r l i g n i n s , 124 K u r a r i d i n , 251 L L a b a t test f o r chalcones, 239 Laccaic acid D methylester, 467 L a p a c h o l , 454, 480 Laser m i c r o p r o b e mass analysis ( L A M M A ) , 228 Laser m i c r o p r o b e mass s p e c t r o m e t r y (LMMS) o f s o l i d lichen substances, 514 L a t h o d o r a t i n , 78 L a w s o n e , 473 - p r e n y l ether of, 473 L e c a n o r i c a c i d , crystals o f , 510 L e p r o l o m i n , , 522 L e p t o s i d i n , 264 L e p t o s i n , 268 L e u c o t y l i n , 512 L i c h e n mass s p e c t r o m e t r y ( L M S ) , 516 L i c h e n substances, 509 G C , 516 H P L C , 517 laser p r o b e M S , 514 l o c a l i s a t i o n , 513 m a j o r classes, 511 m i c r o c h e m i c a l tests, 513 q u a n t i t a t i v e analysis, 519 reagents, 513 scanning e l e c t r o n m i c r o s c o p y , 514 structures, 512, 520 T L C , 515 v i s u a l i s a t i o n , 516 L i c h e x a n t h o n e , 512 L i g n i n , 113 biosynthesis, 139 c a r b o n - N M R spectra, 143 characterisation by chemical degradation, 132 c o l o u r reagents f o r l o c a l i s a t i o n , 128 c y t o c h e m i c a l c h a r a c t e r i s a t i o n , 127 f u n c t i o n a l g r o u p analysis, 136 i n f r a r e d spectra, 140 interference m i c r o s c o p y , 129 K l a s o n - t y p e p r o c e d u r e , 124 m a c r o m o l e c u l a r s t r u c t u r e , 123 mass s p e c t r o m e t r y , 145 M a u l e reagent, 128 m o l e c u l a r w e i g h t d e t e r m i n a t i o n s , 136 n o m e n c l a t u r e , r a d i c a l names i n , 115 o z o n o l y s i s , 135 p h e n y l p r o p a n e m o n o m e r s , 115 p r o t o n N M R spectra, 142 q u a n t i t a t i v e analysis, 126 R a m a n spectroscopy, 141 r o l e i n terrestrial p l a n t s , 122 t h i o a c e t o l y s i s , 135 t h i o g l y c o l i c acid d e t e r m i n a t i o n , 127 U V m i c r o s c o p y , 129 U V spectra, 140 L i g n i n - c a r b o h y d r a t e complexes, 131 L i g n i n - h y d r o g e n o l y s i s , 13 L i g n i n s , 113 o f a n g i o s p e r m s , 120 o f g y m n o s p e r m s , 120 s o l u b l e , 123 L i q u i r i t i g e n i n , 285, 304, 305 L i s e t i n , 426 L o c a l i s a t i o n o f l i c h e n substances, 513 L o x o d e l l o n i c a c i d , 528 L u c e n i n - , 199 L u n u l a r i c a c i d , , 177, 183, 185, 186 L u n u l a r i n , 183, 185 L u p i n i s o f l a v o n e A , 423 L u p i s o f l a v o n e , i d e n t i f i c a t i o n of, 445 L u t e o l i n , 199 8-C-glucoside, 198 Μ ( - ) - M a a c k i a i n , 428 M a e s o p s i n , 269 M a l v i d i n , 328, 332, 347 M a n g i f e r i n , , , 500 M a n g o s t i n , , 498 M a r c h a n t i n A , , 186 M a r i t i m e i n , 264 M a r s u p i n , 269, 270 INDEX Mass s p e c t r o m e t r y ( M S ) chemical i o n i s a t i o n M S ( C I - M S ) , 227 desorption chemical ionisation M S ( D C I - M S ) , 228 o f x a n t h o n e glycosides, 505 electron i m p a c t M S ( Ε Ι - M S ) o f a n t h o c y a n i d i n s , 34, 347 aurones, 266 b i f l a v o n o i d s , 382 chalcones, 254 c i n n a m o y l conjugates, 105 c o u m a r i n s , 105 d i h y d r o c h a l c o n e s , 308, 310 d i h y d r o f l a v o n o l s , 308, 310 flavanones, 308, 309 flavones a n d flavonols, 2 - 2 - h y d r o x y - - b e n z y l c o u m a r a n - - o n e s , 270 i s o f l a v o n o i d s , 442 phenols, 65, 66 p h e n y l p r o p a n o i d s , 105 q u i n o n e s , 483 stilbenoids, 188 t a n n i n s , 412 x a n t h o n e s , 505 fast a t o m b o m b a r d m e n t M S ( F A B - M S ) o f a n t h o c y a n i n s , 347 b i f l a v o n o i d s , 383 c i n n a m i c acid glycosides, 106 c i n n a m o y l i r i d o i d glucosides, 106 flavanoid glycosides, 318 flavonoid glycosides, 228 h y d r o l y s a b l e t a n n i n s , 413 hydroxycinnamoylesters o f malic acid, 105 lignins, 145 p r o a n t h o c y a n i d i n s , 413 q u i n y l m o i e t y o f c h l o r o g e n i c a c i d , 105 v i o l a n i n , 350 x a n t h o n e glycosides, 505 field d e s o r p t i o n M S ( F D - M S ) , 228, 312 o f c i n n a m o y l p h e n y l e t h y l glycosides, 106 laser d e s o r p t i o n M S ( L D - M S ) , 228 laser m i c r o p r o b e mass analysis ( L A M M A ) , 228 laser m i c r o p r o b e M S ( L M - M S ) o f lichen substances, 514 lichen mass s p e c t r o m e t r y ( L M S ) , 516 negative i o n M S , 228 pyrolysis M S ( P y - M S ) o f l i g n i n , 145 M a t t e u c i n o l , 285 M a u l e reagent f o r l i g n i n s , 128 M e d i c a r p i n , 425 M e l i l o t i c acids, 76 Melting points o f aurones, 281 o f chalcones, 275 545 M e r o c h l o r o p h a e i c a c i d , 512 M e t h o x y m i c a r e i c a c i d , 524 - M e t h y l c y a n i d i n , 328 ' - M e t h y l d a v i d i g e n i n , 286, 295, 299, 302, 307, 310 ' - M e t h y l d a v i d i o s i d e , 294, 295, 299, 302, 307 Methyleugenol - M e t h y l j u g l o n e , 477 M e t h y l o d o r a t o l , 288 M e t h y l - P - o r s e l l i n a t e , 528 ' - - M e t h y l s u p e r p h y l l i n i c a c i d , 523, 524 - O - M e t h y l t h i o m e l i n , 526 M i c a r e i c a c i d , 524 M i l l e d w o o d l i g n i n s , 130 Molecular weight determination o f lignins, 136 M o n o a m i n o oxidase i n h i b i t i o n by x a n t h o n e s , 496 M o r e l l o f l a v o n e , 377, 380 M o r i n , 199 M S , see M a s s s p e c t r o m e t r y M u r r a y a q u i n o n e D , 466, 484 M u s s a t i o s i d e s , 80 M u t a g e n i c x a n t h o n e s , 498 M y r i c e t i n , 199 - O - r h a m n o s i d e , 198 M y r i c i t r i n , 199 M y r i c o s i d e , 80 Ν N a p h t h o q u i n o n e s , 456, 459 N a r i n g e n i n , 285, 287, 288, 294, 299, 304, 305, 308, 309 5-glucoside, 240 N a r i n g i n , 285, 288, 294 d i h y d r o c h a l c o n e , 288 N a r i r u t i n , 288 N a t u r s t o f f Reagenz A , 294 N e g a t i v e i o n mass s p e c t r o m e t r y , 228 N e o b a v a c h a l c o n e , 246, 248 N e o e r i o c i t r i n , 288 N e o h e s p e r i d i n , 285, 288 d i h y d r o c h a l c o n e , 288 N i t i d u l a n , 426 N M R spectroscopy, see N u c l e a r m a g n e t i c resonance spectroscopy N o r l i c h e x a n t h o n e , 526 N o r s t i c t i c a c i d , 522, 523 N u b i g e n o l , 286 N u c l e a r m a g n e t i c resonance ( N M R ) spectroscopy c a r b o n - N M R c h e m i c a l shifts f o r / o f a c y l f u n c t i o n s , 223 b o e s e n b e r g i n - B ' , 254 546 N u c l e a r magnetic resonance ( N M R ) chalcones, 253 d i h y d r o c h a l c o n e s , 319 d i h y d r o x y f l a v o n o l s , 318 f l a v a n o i d glycosides, 320 flavanoids, 319 flavanones, 318 h y d r o l y s a b l e t a n n i n s , 414 p r o a n t h o c y a n i d i n s , 416 carbon-13 N M R INDEX (cont.) signals f o r a m e n t o f l a v o n e , 382 solvents f o r flavones a n d flavonols, 216 spectra o f a flavone, 220 a flavone C-glycoside, 221 a flavonol glycoside, 224 a procyanidin-prodelphinidin polymer, 417 c a r b o n - N M R spectroscopy o f a n t h o c y a n i n s , 342, 344 b i f l a v o n o i d s , 381 chalcones, 252 c i n n a m i c a c i d ester conjugates, 102 c o u m a r i n substituents, 104 c o u m a r i n s , 103 flavanoids, 317 flavones a n d flavonols, 218, 219 h y d r o l y s a b l e t a n n i n s , 413 i s o f l a v o n o i d s , 443 l i g n i n , 143 p h e n o l s , 65, 66 p h e n y l p r o p a n o i d s , 101 p r o a n t h o c y a n i d i n s , 415 q u i n o n e s , 482 stilbenoids, 186 x a n t h o n e s , 504 oxygen-17 N M R spectroscopy o f q u i n o n e s , 482, 484 p r o t o n N M R c h e m i c a l shifts f o r acylated a n t h o c y a n i n s , 348 a n t h o c y a n i n s , 347 aromatic protons in hydroxycinnamoyl esters, 100 a u r o n e A - a n d B - r i n g p r o t o n s , 265 d i h y d r o c h a l c o n e s , 315 d i h y d r o f l a v o n o l s , 314 flavanoid aglycones, 316 flavanone glycosides, 316 flavanones, 313 flavones a n d flavonols, 213 proton N M R p a r a m a g n e t i c shifts i n d u c e d b y a c y l a t i o n o f h y d r o x y c i n n a m i c acids b y q u i n i c a c i d , 100 resonances o f H - α a n d Η - β f o r - h y d r o x y c h a l c o n e s , 245 N u c l e a r m a g n e t i c resonance ( N M R ) signals f o r a m e n t o f l a v o n e , 382 spectra o f (cont.) a p i g e n i n 7-O-neohesperidoside, 215 r u t i n , 214 p r o t o n N M R spectroscopy o f a n t h o c y a n i n s , 342, 344 aurones, 265 b i f l a v o n o i d s , 381 chalcones, 244 flavanoids, 312 flavones a n d flavonols, 213 h y d r o l y s a b l e t a n n i n s , 413 h y d r o x y c i n n a m o y l esters, 100 i s o f l a v o n o i d s , 443 l i g n i n , 142 p h e n o l s , 65, 66 p h e n y l p r o p a n o i d s , 99 p r o a n t h o c y a n i d i n s , 415 q u i n o n e s , 483 retrochalcones, 265 s t i l b e n o i d s , 186 x a n t h o n e s , 503 Ο O d o r a t o l , 288 O l i v e t o r i c a c i d , 529, 530 O r c h i n o l , 161, 164 O r c i n o l , 30, 32, 55, 59, , 64 O r g a n o s o l v l i g n i n e x t r a c t i o n , 130 O r i e n t i n , 198, 199 O r o b a n c h o s i d e , 77, 80 O r o b o l , 441 O s a j i n , 422 O S B , see o-Succinylbenzoic a c i d O z o n o l y s i s o f l i g n i n , 135 Ρ Pacheco's test f o r d i h y d r o f l a v o n o l s , 292 P a c h y r r h i z i n , 426 P a n n a r i c a c i d , 529 Paper c h r o m a t o g r a p h y ( P C ) 2-dimensional ( - D PC) o f flavone C- a n d O-glycosides, 204 flavonoid sulphates, 205 flavonol glycosides, 205 h y d r o l y s a b l e t a n n i n s , 408, 409 p h e n o l i c s , 11 p r o a n t h o c y a n i d i n m e t a b o l i t e s , , 409 /^-values o f a n t h o c y a n i n s , 332 b i f l a v o n o i d s , 378 547 INDEX Paper c h r o m a t o g r a p h y ( P C ) (cont.) d i h y d r o c h a l c o n e s , 295 d i h y d r o f l a v o n o l s , 295 flavanones, 294 h y d r o x y c i n n a m o y l amides, 87 h y d r o x y c i n n a m o y l esters, 86 solvent systems f o r , see S o l v e n t systems f o r PC Paper c h r o m a t o g r a p h y o f a n t h o c y a n i n s , 331 b i f l a v o n o i d s , 366 flavanoids, 293 flavones a n d flavonols, i s o f l a v o n o i d s , 433 lichen substances, 514 p h e n o l i c s , 15 p h e n o l s , , 45 p h e n y l p r o p a n o i d s , 85 Paper electrophoresis o f 201 flavonoid g l u c u r o n i d e s , 209 flavonoid sulphates, 209 p h e n o l i c s , 12, 16 p h e n o l s , 46 P a r i e t i n , 512 P C , see Paper c h r o m a t o g r a p h y P e d u n c u l a g i n , , 394, 409 Peganones a n d 2, 461 P e l a r g o n i d i n , 328, 332, 347 β - , , , - P e n t a g a l l o y l - D - g l u c o s e , 393 a , ' , , , ' - P e n t a h y d r o x y c h a l c o n e , 261 P e o n i d i n , 328, 332, 347 P e r l a t o r i c a c i d , 512 P e r m e t h y l a t e d b i f l a v o n o i d s , / ^ - v a l u e s of, 379 Permethyl-ether preparation o f flavonoids, 231 P E S , see P h o t o e l e c t r o n spectroscopy P e t u n i d i n , 328, 332 P e u c e n i n , 78 Pew's test f o r d i h y d r o f l a v o n o l s , 292 P E X , see Pressure e x p a n s i o n p r o c e d u r e Phenanthrenes, 159 i n h i g h e r p l a n t s , 167, 168 P h e n a n t h r o p y r o n e s i n h i g h e r p l a n t s , 165 P h e n o l , 3, 30, 32, 38, 59, , 64 P h e n o l i c acids, see P h e n o l s a n d p h e n o l i c acids Phenolics i n p l a n t s , biosynthesis o f , 5, 34, 36, 37 c h e m i c a l m o d i f i c a t i o n , 23 c h r o m a t o g r a p h y , 10 c o l o u r tests, 10 distribution, enzymes f o r s t r u c t u r a l analysis, 22 frequency o f occurrence, m a j o r classes, m e a s u r e m e n t o f t o t a l p h e n o l i c s , 25 Phenolics i n p l a n t s (cont.) - D p a p e r c h r o m a t o g r a p h y , 11 p a p e r e l e c t r o p h o r e s i s , 12, 16 p r e p a r a t i v e s e p a r a t i o n , 19 reagents f o r d e t e c t i o n , 10 screening p l a n t s f o r , 12 solvents f o r c h r o m a t o g r a p h y , 16, 17 UV spectra, 14 Phenols a n d p h e n o l i c acids, 30 c a p i l l a r y G L C , 52, 53 c h r o m a t o g r a p h i c solvents, - 4 c o l u m n c h r o m a t o g r a p h y , , 45 D C C C , 45 e x t r a c t i o n , 39, 40 G L C , 50, , 54 H P L C , , 55, - , 61 M S , 65, 66 N M R s p e c t r o s c o p y , 65, 66 p a p e r e l e c t r o p h o r e s i s , 46 P C , , 45 q u a n t i t a t i v e d e t e r m i n a t i o n , 67 spray reagents, 48 T L C , , , , 47 UV spectroscopy, 63, 64 Phenoxyradicals, produced by peroxidative o x i d a t i o n o f c o n i f e r y l a l c o h o l , 117 P h e n y l d i h y d r o i s o c o u m a r i n s , 159 P h e n y l p r o p a n e m o n o m e r s o f l i g n i n , 115 Phenylpropanoid production in cultured tissues, 80 P h e n y l p r o p a n o i d s , 75 M S , 105 N M R spectroscopy, 0 - P C , 85 T L C , 85 UV spectroscopy, 95 P h l o r e t i c acids, 76 P h l o r e t i n , 286, 288, 295, 304, 307, 319 P h l o r i d z i n , 286, 288, 295, 307 P h l o r o g l u c i n o l , 3, , 32, 34, 59, , 64 P h l o r o t a n n i n s , 390 P h o t o e l e c t r o n spectroscopy ( P E S ) o f q u i n o n e s , 485 P h y l l o d u l c i n , 160 P h y l l o q u i n o n e , , 474 P h y s c i o n , , , , 482 P h y s o d a l i c a c i d , 528 P h y s o d i c a c i d , 529, 530 Phytoalexins, anthraquinone, 474 a - h y d r o x y d i h y d r o c h a l c o n e , 288 i s o f l a v a n o i d , , 437 s t i l b e n o i d , 180 P i m p i n e l l i n , 95 P i n o b a n k s i n , 285, 298 P i n o c e m b r i n , 285, 298, 305, 308 548 INDEX Pinoresinol, P i n o s t r o b i n , 285, 298 P i n o s y l v i n , , 169, 183, 185 P i s a t i n , 425 P l a n t g r o w t h r e g u l a t o r s , s t i l b e n o i d , 181 Plectranthones E, F, G , Η , I a n d J , 463 Plectranthones Κ a n d L , 464 (16S)-Plectrinone A , 464 P o d o c a r p u s f l a v o n e A , 358 P o l y h y d r o x y f l a v a n - - o l s , 398 P o m i f e r i n , 422, 441 P o n c i r i n , 288, 294 d i h y d r o c h a l c o n e , 289 P o p u l i n , 30 P o r i o l , 298 Pratensein, 441 P r e p a r a t i v e separations o f p h e n o l i c s , c o m p a r i s o n of, 19 Pressure e x p a n s i o n ( P E X ) p r o c e d u r e f o r e x t r a c t i n g q u i n o n e s , 477 P r o a n t h o c y a n i d i n A , 401 P r o a n t h o c y a n i d i n s , 398 acid-catalysed cleavage, 404 biosynthesis, 392 e p i m e r i s a t i o n a n d a r r a n g e m e n t o f catechin i n a l k a l i n e s o l u t i o n , 405 esters, 401 F A B - M S , 413 glycosides, 401 N M R spectroscopy, 413 p o l y h y d r o x y f l a v a n - - o l s , 398 p o l y m e r s , 401 reactions, 403 relative / ^ - v a l u e s o n - D P C , 409 s t r u c t u r a l analysis, 404 tests specific f o r , 407 t r i m e r , 392 399 P r o c y a n i d i n s B{-B^ P r o t o c a t e c h u a l d e h y d e , , 32 P r o t o c a t e c h u i c a c i d , , 34, 59, , 64 ( + )-Protolichesterinic a c i d , 512 P r u n e t i n , 441 P r u n i n , 285 Prussian blue m e t h o d , f o r m e a s u r i n g t o t a l phenolics, 25, 26 P s e u d o b a p t i g e n i n , 441 Psoralen, 78, 88 P s o r o s p e r m i n , 497 P t e r o c a r p a n s , 424 M S , 442 skeleton, 425 U V spectra, 439, 440 Pterocarpenes, 424 U V spectra, 439, 440 P u l c h e l l i d i n , 328 P u l v i n i c a c i d , 512 P u r p u r i n , 480 P V P c o l u m n c h r o m a t o g r a p h y o f p h e n o l s , 45 Pyranocoumarins H P L C , 95, 96 U V spectroscopy, 98 P y r a y a q u i n o n e s A a n d B, 466 P y r o g a l l o l , 3, , 32, 64 Pyrolysis mass s p e c t r o m e t r y ( P y - M S ) o f l i g n i n s , 145 Q Quantitative determination o f a n t h o c y a n i n s , 339 b i f l a v o n o i d s , 385 flavanones, 290 i s o f l a v o n o i d s , 445 lichen substances, 519 l i g n i n , 126 phenolics, 25 p h e n o l s , 67 q u i n o n e s , 478, 479 t a n n i n s , 405 Q u e r c e t a g e t i n , 199 Q u e r c e t i n , , 199 - a - a r a b i n o p y r a n o s i d e , 21 Q u e r c i t r i n , 199 Q u i n o n e s , 451 a n t h r a - , 454, 456, 459 benzo-, 458 biosynthesis, 466 C C , 481 f u n c t i o n s , 476 G C , 481 yV-heterocyclic, 466 H P L C , 479 i s o l a t i o n , 476 n a p h t h o - , 459 new p l a n t sources, 454 p l a n t cell cultures as sources, 455, 456 s t r u c t u r e d e t e r m i n a t i o n , 481 t e r p e n o i d , 463 T L C , 478 R Radioimmunoassay ( R I A ) of h e s p e r i d i n , 290 sennoside B, 478 R a m a n spectroscopy o f a n t h o c y a n i n s , 351 l i g n i n , 141 R a v e n e l i n , 526 Reagents, see C o l o u r tests or S p r a y reagents INDEX R e s o r c i n o l , 3, 30, 32, 34, 38, 55, 59, , 64 R e s v e r a t r o l , , 169, 183, 185 R e t r o c h a l c o n e s , 261 p r o t o n N M R o f , 262 R h a m n e t i n , 199 2"-0-Rhamnosylvitexin c a r b o n - N M R s p e c t r u m of, 221 R h a p o n t i n , 160, 173 R h e i n , 454, 480 R h e i n a n t h r o n e 8-glucoside, 476 R h o d o c l a d o n i c a c i d , 512 R I A , see R a d i o i m m u n o a s s a y R o b i n e t i n i d o l , , 398 - ( a - > ) - c a t e c h i n - ( - > a ) - r o b i n e t i n i d o l , 400 R o b u s t a f l a v o n e , 359, 360, 379, 383, 384 R o s i n i d i n , 328 R o t e n o i d s , 423 skeleton, 423 U V spectra, 439, 440 R o t e n o n e , 423, 427, 446 R o x b u r g h i n o l , , 483 R u g o s i d i n D , 397 R u t i n , 199, 214 S S a k u r a n e t i n , 285, 294 S a k u r a n i n , 294 Salicin, 30, 59, 61 S a l i c y l a l c o h o l , 30, 32, 34, 38 Salicylaldehyde, , 32, 38, 64 Salicylic a c i d , , 33, 38, 64 Sanguinone A , 464, 484 S c a n n i n g electron m i c r o s c o p y o f crystals i n lichens, 514 S C E , see S u p e r c r i t i c a l e x t r a c t i o n Schaftoside, 199 Schizopeltic a c i d , 529 S c i a d o p i t y s i n , 358, 377, 378, 380, 385 S c o p a r i n , 199 Scoparone, 87 S c o p o l e t i n , 78, 87, 93 S c o p o l i n , 78 Screening p l a n t s f o r p h e n o l i c s , 12 m - S c r o b i c u l i n , 523, 524 /?-Scrobiculin, 523, 524 Scutellarein, 199 Secalonic acids A a n d C , 526 Sekikaic a c i d , 523, 524 Sennoside B, 478 Sennosides, 456, 479 Sephadex L H - C C o f anthracenes, 481 f l a v a n o i d s , , 301 549 Sephadex L H - C C o f {cont.) i s o f l a v o n o i d p h y t o a l e x i n s , 438 p r o a n t h o c y a n i d i n s , 410 x a n t h o n e s , 500 S e q u i o a f l a v o n e , 358 Sesamol, , 32, 34 S F C , see C a p i l l a r y c o l u m n s u p e r c r i t i c a l chromatography S h i k o n i n , 455, 475, 483 S h i n o d a test f o r flavanoids, 292 Sinapic a c i d , 76, 89, , 97 S k i m m i n , 78 fluid S o d i u m b o r o h y d r i d e reagents, 292, 296, 297 S o f t w o o d l i g n i n , m o l e c u l a r s t r u c t u r e of, 118 Solvent systems for PC of d i h y d r o c h a l c o n e s , 295 d i h y d r o f l a v o n o l s , 295 flavanones, 294 flavones a n d flavonols, 202 p h e n o l i c s , 16 p h e n o l s , 42 p h e n y l p r o p a n o i d s , 86, 87 stilbenes, 182 sugars, 202 for T L C of b i f l a v o n o i d s , 367, 369 d i h y d r o c h a l c o n e s , 299 flavones a n d flavonols, 205, 206 i s o f l a v o n o i d s , 435 lichen substances, 515 p h e n o l i c s , 17 phenols, 42^44 phenylpropanoids, 86-88 s t i l b e n o i d s , 183 x a n t h o n e s , 501 S o p h e r a n i n , 461 S o p h o r a d o c h r o m e n e , 247 S o r d i d o n e , 512 Sotetsuflavone, 358, 377, 380 S p h o n d i n , 93 Spot c o l o u r i n t e r p r e t a t i o n o f flavones a n d flavonols, 203 S p o t c o l o u r s i n U V l i g h t , see C o l o u r s i n U V light S p r a y reagents f o r c h r o m a t o g r a p h i c d e t e c t i o n of b i f l a v o n o i d s , 377 chalcones, 239 flavanoids, 297 flavones a n d flavonols, 203 lichen substances, 516 p h e n o l i c s , 10 p h e n o l s , 48 S t e n o s p o r o n i c a c i d , 530, 531 550 INDEX Stilbene - c a r b o x y l i c acids i n p l a n t s , 177 glycosides i n p l a n t s , 173, 174 p o l y m e r s i n p l a n t s , 175, 176 Stilbenes, 159 i n h i g h e r p l a n t s , 169-171 i n w o o d , 181 p r e n y l a t e d , 161, 172 Stilbenoid a n t i f u n g a l c o m p o u n d s , 180 p h y t o a l e x i n s , 180 p l a n t g r o w t h r e g u l a t o r s , 181 S t i l b e n o i d s , 160 biosynthesis, 179 e x t r a c t i o n , 181 G L C , 183 H P L C , 184 M S , 188 N M R spectroscopy, 186 synthesis, 188 T L C , 183 U V spectra, 185 S t r e p s i l i n , 512 S t r o b o b a n k s i n , 285 S t r o b o p i n i n , 285 Structural transformation o f anthocyanins, 330 Structures o f a n t h o c y a n i d i n s , 328 aurones, 238 b i f l a v o n o i d s , 358, 359 chalcones, 238 c h r o m o n e s , 78 c o u m a r i n s , 77 d i h y d r o c h a l c o n e s , 286 d i h y d r o f l a v o n o l s , 285 flavanones, 285 flavones a n d flavonols, 198, 199 h y d r o x y c i n n a m i c acids, 76 i s o f l a v o n o i d s , 421 l i g n i n s , 115 phenolics, p h e n y l p r o p a n o i d s , 76 retrochalcones, 261 s t i l b e n o i d s , 161 t a n n i n s , 390, 391 o-Succinylbenzoic a c i d , 472 Sugar analysis o f flavonoids, 229 S u l f u r e t i n , 266, 269 S u p e r c r i t i c a l e x t r a c t i o n ( S C E ) o f l i g n i n , 130 S u p e r l a t o l i c a c i d , 523, 524 S w e r c h i r i n , 496 Synthesis o f aurones, 268 chalcones, 257 s t i l b e n o i d s , 188 S y r i n g a l d e h y d e , , 32 S y r i n g i c a c i d , , 33, 34, 64 S y r i n g y l l i g n i n , 118 Τ T a n n a s e , 402 T a n n i c a c i d , 393 Tannins biogenetic r e l a t i o n s h i p s , 391 biosynthesis, 392 C D spectra, 412 c e n t r i f u g a l p a r t i t i o n c h r o m a t o g r a p h y , 411 c h i r o p t i c a l p r o p e r t i e s , 412 c h r o m a t o g r a p h y , 408 condensed, 390, 398 e x t r a c t i o n , 410 H P L C , 411 h y d r o l y s a b l e , 390, 393 h y d r o l y s i s w i t h tannase, 402 M S , 412 N M R spectroscopy, 413 q u a n t i t a t i v e e s t i m a t i o n , 405 reactions, 402 relative a f f i n i t y t o m e t h y l e n e b l u e , 408 relative astrigency test f o r , 408 structures, 390, 391 U V spectroscopy, 411 T a x i f o l i n , 285, 288, 306, 310 T e c t o q u i n o n e , 454 T e c t o r i g e n i n , 441 T e l l e m a g r a n d i n , , 409 T e p h r o s i n , 425 T e r g a l l a g i n , 397 T e r g a l l i n , 398 , , , - T e t r a g a l l o y l - D - g l u c o s e , 393 T e u c r i o s i d e , 106 T e x a s i n , 441 T F G , see T h e r m o f r a c t o g r a p h y T h a m n o l i c a c i d , 512 T h e r m o f r a c t o g r a p h y ( T F G ) o f q u i n o n e s , 478 T h i n layer c h r o m a t o g r a p h y ( T L C ) c e n t r i f u g a l , o f x a n t h o n e s , 500 densitometry o f q u i n o n e s , 479 x a n t h o n e s , 501 enzymatic hydrolysis, o f anthracene glycosides, 478 ^-values of a n t h o c y a n i n s , 332 b i f l a v o n o i d s , 377, 378 c o u m a r i n s , 87 d i h y d r o c h a l c o n e s , 299 f u r a n o c o u m a r i n s , 88 h y d r o x y c i n n a m o y l amides, 87 551 INDEX T h i n layer c h r o m a t o g r a p h y ( T L C ) (cont.) h y d r o x y c i n n a m o y l esters, 86 i s o f l a v o n o i d s , 444 p e r m e t h y l a t e d b i f l a v o n o i d s , 379 p h e n o l i c acids, 47 solvent systems, see Solvent systems f o r TLC spectrophotometry, for quantitative d e t e r m i n a t i o n o f q u i n o n e s , 479 T h i n layer c h r o m a t o g r a p h y o f a n t h o c y a n i n s , 333 b i f l a v o n o i d s , 366, 368 c o u m a r i n s , 85, 87 flavanoids, 298 flavones a n d flavonols, 205, 206 f u r a n o c o u m a r i n s , 88 i s o f l a v o n o i d p h y t o a l e x i n s , 437 i s o f l a v o n o i d s , 433 lichen substances, 515 phenolics, 15 phenols, , , 46, 47 p h e n y l p r o p a n o i d s , 85 q u i n o n e s , 478 s t i l b e n o i d s , 182, 183 T h i o a c e t o l y s i s o f l i g n i n , 135 T h i o g l y c o l i c acid d e t e r m i n a t i o n o f l i g n i n , 127 T h i o m e l i n , 526 diacetate, 526, 528 T h y m o l , 30, 32, 34, 38 T i l i r o s i d e , c a r b o n - N M R s p e c t r u m of, 224 T i n g e n o n e , 465 T i r u m a l i n , 306, 308, 310 Tissue cultures a c c u m u l a t i n g q u i n o n e s , 456 T i t a n i u m method for measuring total p h e n o l i c s , 25, 26 T L C , see T h i n layer c h r o m a t o g r a p h y T M S - e t h e r p r e p a r a t i o n o f flavonoids, 231 T o c o p h e r o l s , , 481 T o r o s a c h r y s o n e - p - D - g e n t i o b i o s i d e , 462 T r i c e t i n , 199 T r i c i n , 199 , , ' - T r i h y d r o x y a u r o n e , 265, 266 T r i v i a l names o f c o m m o n flavonoids, 199 U l t r a v i o l e t ( U V ) spectra o f (cont.) p i n o s y l v i n a n d its m e t h y l e t h e r s , 184 r u t i n , 210 U l t r a v i o l e t ( U V ) spectral m a x i m a o f a u r o n e s , 281 b i f l a v o n o i d s , 380 chalcones, 275 c h r o m o n e s , 97 c i n n a m o y l c o n j u g a t e s , 97 c o u m a r i n s , 97 d i h y d r o c h a l c o n e s , 307 d i h y d r o f l a v o n o l s , 306 flavanones, 305 flavones a n d flavonols, 211 f u r a n o c o u m a r i n s , 98 isoflavones, 441 i s o f l a v o n o i d classes, , 440 m a j o r p h e n o l i c classes, 14 p h e n o l s , 63, 64 s t i l b e n o i d s , 185 x a n t h o n e s , 502 U l t r a v i o l e t ( U V ) spectroscopy o f a n t h o c y a n i n s , 339 a u r o n e s , 264 b i f l a v o n o i d s , 379 chalcones, 243 c o u m a r i n s , 98 flavanoids, 302 flavones a n d flavonols, 209 i s o f l a v o n o i d s , 439 l i g n i n , 140 p h e n o l i c s , 13 p h e n o l s , 63 p h e n y l p r o p a n o i d s , 95 s t i l b e n o i d s , 185 t a n n i n s , 412 x a n t h o n e s , 502 U m b e l l i f e r o n e , 77, 87, 93 U r u s h i o l , 30, 32, 38 U s n i c a c i d , 512, , 522 U V , see U l t r a v i o l e t U v a n g o l e t i n , 286, 307 Uvaretin, 286-288 U V U b i q u i n o n e - , 457 U b i q u i n o n e s , 480 U l t r a v i o l e t ( U V ) m i c r o s c o p y o f l i g n i n s , 129 U l t r a v i o l e t ( U V ) spectra o f a m e n t o f l a v o n e , 381 b e l l i d i f o l i n , 503 d a v i d i o s i d e , 203 d e s m e t h y l b e l l i d i f o l i n , 503 d i h y d r o a m e n t o f l a v o n e , 381 V a n i l l i c a c i d , , 33, 64 V a n i l l i n , , 38, 56, 64 r e a c t i o n , 25, 26 test f o r p r o a n t h o c y a n i d i n s , 407 V e r b a s c o s i d e , 80 V e s t i t o l - ( , ' ) - v e s t i t o l , 426 V i c e n i n s 1-3, 199 ε - V i n i f e r i n , , 185 V i o l a n i n , 350 552 V i o l a n t h i n , 199 V i s m i o n e C , 459 V i s m i o n e s D a n d E, 460 V i s n a g i n , 78 V i t e x i n , 199 W Wessely-Moser rearrangement o f flavone C-glycosides, 232 W r i g h t i i n , 528 X X a n t h e l e t i n , 95 X a n t h o n e s , 493 a n t i m i c r o b i a l a c t i v i t y , 499 b i o l o g i c a l p r o p e r t i e s , 495 biosynthesis, 494 c h e m o t a x o n o m y , 499 INDEX X a n t h o n e s (cont.) c y t o t o x i c a c t i v i t y , 496 i n h i b i t i o n o f m o n o a m i n e oxidase, 496 i s o l a t i o n , 500 M S , 505 m u t a g e n i c a c t i v i t y , 498 N M R spectroscopy, 505 occurrence, 494 structures, 494 1,3,5,8-substituted, 496 T L C , 500, 501 U V spectroscopy, 502 X a n t h o t o x i n , 78, 88, 93, 95, 98 X a n t h o t o x o l , 78 X a n t h o x y l e t i n , 95 X a n t h o x y l i n , , 33 Ζ Z i n c / h y d r o c h l o r i c acid spray reagent, 297 ... Anthraquinones 26 6-2 95 23 5-3 05 22 7-2 45, 31 0-3 32 c 210, - , - 3 , - 30 0-3 10, 32 0-3 30 26 5-2 70, 27 2-2 80, 30 0-3 06, 31 0-3 15 25 5-2 65, 31 0-3 30 c 225, - , - 3 25 0-2 70, 33 0-3 50 - , c 300, - 24 0-2 60, 36 5-3 90 24 0-2 70,... 24 0-2 60, 36 5-3 90 24 0-2 70, 39 0-4 30 26 7-2 75, 47 5-5 45 23 0-2 45, 25 0-2 65, 30 5-3 30, 34 0-4 00 26 0-2 90, 37 5-4 10 22 0-2 50, 25 0-2 90, 33 0-3 40, 40 0-4 30 22 0-2 30, 25 2-2 60, 26 7-2 79, 43 0-4 50 " Usually in MeOH as... Gentisic 2,3-Dihydroxy 2-Hydroxy-4-methoxy 2-Hydroxy-5-methoxy 2-Hydroxy-6-methoxy 3,5-Dihydroxy Flavones Apigenin (Ap) Luteolin (Lu) Chrysoeriol Ap 7-methyl ether Lu 7-methyl ether Tricin Ap 5-methyl