AUTHOR INDEX

Albrecht, Anne-Marie, 545 Amaral, Luciene Ferreira G.,

883 Arakaki, Rieko, 597 Arcioni, Sergio, 343 Auser, Patricia, 315

Bacher, Adelbert, 43 Bavage, Adrian D., 301 Bekker, Riaan, 163,245 Berke, Benedicte, 779 Bezuidenhoudt, Barend B. C.

B., 147 Bowley, Steve, 315 Brandt, E. Vincent, 163, 245 Burlat, Vincent, 393

Cai, Ya, 697 Capucci, Raffaella, 343 Carando,Stephane,725 Cheynier, Veronique, 223 Cheze, Catherine, 779 Chiba, Tsuyoshi, 471 Clifford, Mike N., 697 Couhnan,Bruce,315

Damiani, Francesco, 343 Davin, Laurence B., 393,

675 Davies, Alan P., 697 Davis, Adrienne L., 697 Day, Andrea J., 415 De Bruyne, Tess, 193 De Cooman, Luc, 739 Deffieux,Gerard,779 De Keukeleire, Denis, 739 Deprez, Stephanie, 357 de Sousa Menezes, Fabio, 883 Doco, Thierry, 223 Dommisse, Roger, 193 Drilleau, Jean-Fran~ois, 211

Eisenreich, Wolfgang, 43 Elder, Thomas, 83 Erlandson, Martin, 867 Expert, Dominique, 545

Falk, Jon, 315 Feldman, Ken S., 101 Ferreira, Daneel, 147, 163,

245 Floriano, Nubia, 883 Ford, Joshua D., 675 Forster, Hartmut, 371 Fukai, Toshio, 259 Fulcrand, Helene, 223

Garcia-Conesa, Maria T., 483 Garcia Limeira, Vania L., 883 Gonzalez-Hernandez, Maria

P.,897 Goodsall, Chris, 697 Grace, Stephen C., 435 Gross, Georg G., 63, 911 Gruber, Margaret Y., 315,

867 Guimariies Leitiio, Gilda, 883 Guimariies Leitiio, Suzana,

883 Guyot, Sylvain, 211, 223

Hagerman, Ann E., 495 Hano, Yoshio, 279 Happe, Patricia J., 897 Hara, Yukihiko, 629 Haslam, Edwin, 15 Hatano, Tsutomu, 127,507,

597,615,643 Hedges, John I., 853 Hehn, Richard F., 83 Hemingway, Richard W., 507,.

527,911 Hergert, Herbert L., 3

Herlihy, Thomas E., 791 Hernes, Peter J., 853 Heyerick,Arne,739 Hinks, Christopher F., 867 Honma, Takeshi, 629 Hurrell, Richard, 545 Huneau, Jean-Fran~ois, 545 Hunter, Kendra L., 101

Ida, Y oshiteru, 597 Ikeda, Masahiko, 471 Ito, Hideyuki, 127

Jervis, Judith, 83 Jiang, Zhi-Hong, 761

Kalita, Jogen, 739 Karchesy, Joseph J., 897 Kawai, Eiji, 471 Kayser, Oliver, 575 Kiderlen, Albrecht F., 575 Koizumi, Haruko, 471 Kolodziej, Herbert, 193, 575 Kouno, Isao, 761 Koyama, Noriko, 597 Kwon, Mi, 393

Lange, Karen M., 897 Latte, Klaus Peter, 575 Lawlor, Michael D., 101 Lees, Garry L., 315, 867 Le Guerneve, Christine, 211 Le Roux, Erwan, 223 Lewis, John R., 697 Lewis, Norman G., 393, 675 Lopes Mensor, Luciana, 883

Marmolle, Frank, 545 Marnet, Nathalie, 211 Matsuda, Michiaki, 629 McIntosh, Thomas J., 451

915

916

McKersie, Bryan, 315 Mila, Isabelle, 545 Milligan, Stuart R., 739 Mitsunaga, Tohru, 555 Miura, Shinji, 471 Miura, Yukiko, 471 Miyamoto, Ken-ichi, 643 Morris, Phillip, 301 Muir, Alister D., 315, 867 Murayama,Tsugiya,643

Nakamura, Yoshiyuki, 629, 665

Nakashima, Hideki, 597 Nel, Reinier J. J., 147, 163 Niehaus, Joerg U., 63 Niemetz, Ruth, 63 Noda, Yuko, 665 Nomura, Taro, 259, 279 NQnaka, Gen-ichiro, 761 Noro, Kazuko, 665 Noro, Tadataka, 629, 665 Nursten, Harry E., 697

Ohki, Takeshi, 665 Okuda, Takuo,127, 597, 615,

643 Onyilagha, Joseph, 867

Paolocci, Francesco, 343 Parry, Andrew, 697 Pieters, Luc, 193 Pizzi, Antonio, 805 Plumb, GeoffW., 483 Pollastri, Michael P., 451

Pommer,Ulrich,371 Porter, Ned A., 451 Powell, Chris, 697 Premanathan, Mariappan,

597 Preston, Caroline M., 825 Pryor, William A, 435

Quideau, Stephane, 101

Ranatunga, Thilini, 83 Ray, Heather, 315 Remy, Sophie, 223 Rice, Robyn E., 495 Riedl, Ken M., 495 Robbins, Mark P., 301 Rong, Haojing, 739

Safford, Robert, 697 Sahasrabudhe, Kiran, 101 Sakagami,Hiroshi,597 Satoh, Kazue, 597 Savage, Rodney A, 371 Scalbert, Augustin, 357, 545 Shibata, Naomi, 629 Simon, Sidney A, 451 Skadhauge, Birgitte, 315 Soroka, Julie, 867 Souquet, Jean-Marc, 223 Starkey, Edward E., 897 Stougaard,Jens, 315

Tanaka, Takashi, 761 Teissedre, Pierre-Louis, 725 Thiru, Ambalavanar, 697

Author Index

Thomsen, Karl K., 315 Tobiason, Fred L., 527 Tome, Daniel, 545 Tomita,Isao,471,629,665 Tomita, Takako, 471

Umegaki, Keizo, 471

Vanden Berghe, Dirk, 193 van Heerden, Pieter S., 147 van Rensburg, Hendrik, 147,

163 Vercauteren, Joseph, 779 Vergoten, Gerard, 527 Vlietinck, Arnold, 193 von Wettstein, Diter, 315

Walkinshaw, Charles H., 843

Wan, Xiaochun, 697 Wang, Ching-Chiung, 615 Warashina, Tsutomu, 629,

665 Werner, Ingo, 43 Wilkins, John, 697 Williamson, Gary, 415, 483 Wray, Victor, 193

Yamasaki, Hideo, 435 Yang, Ling-Ling, 615 Yen, Kun-Ying, 615 Yoshida, Takashi, 127, 507,

597,615,643,911

Zhentian, Lei, 83

SUBJECT INDEX

Acacia mearnsii (black wattle), 164, 560 Acalyphidin D1: from Acalypha hispida, 129 Acer nikoense, 601 Acetaldehyde: de-astringency, 762 Adhesion, 451 Aesculus hippocastanum, 194 Agrimonia pilosa, 644, 646 AgrinlOniin

anticancer activity, 644, 649 cytotoxicity, 654-661 histamine suppression, 139

Albanin D, 272 Albanin E, 272 Alpinumisoflavone,271 Agrobacterium rhizogenes, 302 Alfalfa

antisense chalcone synthase, 335 transgenic plants, 335

Alouatta fusca (howler monkey) feeding preferences, 885, 889 nutrient intake balance, 885

Ampelopsin (dihydromyricetin), 148, 563 Anadenathera peregrina (Leguminosae)

antioxidant activity, 888 howler monkey diet, 886

Anthocyanin regulatory genes, 333 Anti-HIV activity

lignins,608 tannins, 605-608

Antiatherogenesis,471 Antioxidant

flavonoids,488-491 hydroxycinnamate dimers, 486, 489, 491 hydroxycinnamate esters, 489, 491 hydroxycinnamates,484,488,491 metmyoglobin method, 498 oxygen radical absorbance capacity assay,

499 phenylpropanoids, 435 structure-function relationships, 488, 489 tannins, 495-501 tea polyphenol, 472-477

Antioxidant activity: effect of extractants, 888

Antitumor activity ellagitannins, 615-624, 644-649 hydrolyzable tannin, 665-672 against mammary carcinoma MM2, 646,

649,654,655 against Meth-A fibrosarcoma, 649, 656 against MH134 hepatoma, 649 against sarcoma 180,644,645,649 tea aqueous non-dialysates, 629-640

Apigenin (glycosides), 422, 423 ApoE-deficient mice, 477-480 Apoptosis induction

tannins and lignins, 597-605 woodfordin C, 622

Apple, 225, 417,422 Apuleia leiocarpa (Leguminosae)

antioxidant activity, 888 howler monkey diet, 886

Arachis hypogea (peanut), 169 Arctostaphylos uva-ursi, 668 Artobilochromen, 272 Artocarpesin, 288, 289 Artocarpus communis, 272 Artocarpus nobilis, 272 Artonin E, 272 Artonin I, 288 Ascorbic acid, 472, 600 Astringency

effect on cervid diet, 901 seasonal variation, 899, 904 stimulation of ingestion, 890

Baikiaea plurijuga, 178 Barley: ant mutants, 323, 324 Beer

chill haze, 751 lightstruck flavor, 748 pe~anent (irreversible) haze, 751 polyvinyl-polypyrrolidone (PVPP) and haze

prevention, 751

917

918

Benzofuranoid-type biflavonoid from Berchemia zeyheri, 245 biosynthetic significance, 255 CD,252-255 reductive cleavage, 249, 250, 252 structural elucidation, 247-255

Berchemia zeyheri (red ivory), 175,245,247, 255,256

Bergenin, 645,649 Bertha armyworm (Mamestra configurata),

868,871 Bisulfite: decoloration by, 779 Black tea

antitumor promotion, 629-640 aqueous non-dialysate, 630, 632-640 enzymatic and chemical modification, 633-

634 flavonol content, 417 oxidative transformation, 698 pigments, 26

Bloat,343 prevention by condensed tannins, 344

Bone marrow macrophages, 588 Brackenridgea zanguebarica, 249 Bradykinin,521, 523 Brassica napus, 871 Bridelia ferruginea, 194, 199 Brosimone L, 272 Brosimopsis oblongifolia, 272 Brosimum guianense (Moraceae): howler mon-

key diet, 886 Broussoflavonol C, 261 Broussoflavonol D, 261 Broussoflavonol E, 261 Broussonetia papyrifera, 261 Bursera leptophloeos, 272 Butler, Larry G.: dedication to the late, 15

Caffeic acid, 483, 486, 491 antioxidant, 441 ferrylmyoglobin reaction, 441 tyrosinase reaction, 439

Caffeic acid derivative, 645, 649 Camellia sinensis (tea plant), 37,472,556,

629,697 free radical scavengers, 884

Camellia sinensis var. assamica: black tea, 698 Camellia sinensis var. sinensis: green tea, 698 Camelliin B, 607, 648 Cancer chemoprevention

lignans,675,677,683 mammalian lignan, 675-688

Caryophyllene, 743 Castalagin

growth inhibition of Erwinia chrysanthemi, 548

iron deprivation, 547

Subject Index

Casuarictin, 496, 644 (+)-Catechin, 216, 225, 235, 485, 510, 577,

578,596 antiatherosclerosis, 480 antioxidant, 472-474, 490, 498 bio-conversion by wood-rotting fungi, 566 dimerization-rearrangment, 181 immunostimulating effect, 580 interaction with bradykinin, 521 interaction with Gly-Pro, 521 interaction with Gly-Pro-Gly-Gly, 522, 528 interaction with glycyl-L-prolyl-glycyl-

glycine, 536 interaction with proline (cis-4-

hydroxyproline), 520, 535 interaction with Pro-Gly, 521 interaction with Pro-Val, 521 interaction with L-prolyl-glycine, 535 iron deprivation, 547, 550 nuclear exchange reaction, 559 plasma concentrations in humans, 734 polyphenol oxidase oxidation, 237 reaction with amino acid and formaldehyde,

765 self association, 521, 529 TNF inducer, 588

Catechin oxidation peroxidase, 714, 716 polyphenol oxidase, 714, 717

Catechin-(4-8)-epicatechin: antioxidant, 491 Catechin-(4a, 8)-catechin, see also Procyanidin

B-3 compact conformer, 517 conformational analysis by NMR, 511-512,

515,517 extended conformer, 517 rotational isomerism, 510 solvent-dependent change ofNMR, 515 synthesis, 510

Catechin-(4a, 8)-epicatechin, see also Procyanidin B-4

antimicrobial activity, 586 compact conformer, 517 conformational analysis by NMR, 511-517 extended conformer, 517 leishmanicidal activity, 589 rotational isomerism, 510 solvent-dependent change ofNMR, 515-

517 synthesis, 510

Catechin-(4a, 8)-catechin-(4a, 8)-catechine antimicrobial activity, 582 leishmanicidal activity, 589

Catechins: dietary intake from wine, 733 Catechol-O-methyltransferase, 426, 429 Ceriops decandra, 601, 604605 Chalcomoracin, 282, 283, 285, 286, 288-293

Subject Index

Chalcone, 149 Chalcone synthase: antisense, 306 Chamaecyparis obtusa (Hinoki), 558 Chemical defense

astringency, 33 molecular recognition, 33 Oerophtera brumata, 36

Chlorogenic acid biosynthesis, 436 ESR (radical species), 439-447 ferrylmyoglobin reaction, 441 horseradish peroxidase reaction, 438 tyrosinase reaction, 439

Chrome azurol S assay, 547 Chrysobactin, 547 Cider apple polyphenols

IH-NMR,217-219 LC-ESI-MS, 231-233 polymerization degree, 211-231 thiolysis, 215-217

Cinnamyl glucosides: defense mechanisms, 384

Circular dichroism (CD) of bradykinin, 523 of cytochrome c, 523 of dihydroflavonol, 152, 153 of epoxychalcone, 149 of maesopsin analogues (biflavonoids), 252-

255 Colophospermum mopane, 178 Complex gallotannins: biosynthesis, 72 Complexation between iron and polyphenols

in human nutrition, 549 in plant defense, 546

Condensed tannins (proanthocyanidins), 597, 645,649

biosynthesis, 317, 344 cider apple procyanidins, 211-231 co-suppression in transgenic L.

corniculatus, 351 degree of polymerization, 212-219 developmentally-regulated accumulation, 322 effect on crop insect diets, 867 effect on protein nutrition, 875 endoplasmic reticulum vesicles, 321 feeding deterrence, 879 forage quality, 316 free radical scavengers, 884 gene isolation, 323 histochemistry, 321 levels in transgenic L. corniculatus, 345 negative L. corniculatus mutants, 345 IH-NMR,217-219 thiolysis, 213, 214 vacuole, 321

Conuerin,371,374 J3-g1ucosidase in xylem, 376

Coniferyl alcohol, 681, 683, 684, 687 Coriariin A, 103,644 Corilagin

antitumor-promotion, 666, 670, 672 cytoprotective effect, 590 TNF inducer, 588

Coriolus versicolor, 566 Cornusiin C, 620

919

Cosuppression: L. comiculatus mutants, 345 p-Coumaric acid, 483, 486, 491 Crataegus cuneata, 601, 604 Cryptomeria japonica (Sugi), 558 Cudraflavone E, 270 Cudraxanthones, 270 Cuphea hyssopifolia, 616 Cuphiin D1: in Lythraceae, 132 Cuphiins, 616 Cytochrome c, 523

Daunomycin: inhibition ofpoly(ADP-ribose) glycohydrolase, 137

De-astringency, 762 Deer (Odocoileus hemionus columbianus):

diet, 897 Dehydrodicatechin A, 556 Dehydrodigalloyl ether: synthesis, 109 Dehydrodigalloyl unit: synthesis, 116 Dehydroellagitannin, 644, 648, 649 Dehydrohexahydroxydiphenoyl (DHHDP) es-

ter: synthesis, 110, 119 Dehydrokuwanon C, 279, 280 5-Deoxyproanthocyanidins,

antimicrobial activity, 585 leishmanicidal activity, 589

Derrone, 271 Desmodium, 302 Diamondback moth (Putella xylostella), 868 Diaryl ether: synthesis, 109 Diarylpropenes (l,3-diarylpropene), 155-159

asymmetric dihydroxylation, 157, 177 cyclization, 158, 159, 177

Diels-Alder reaction, 280, 281 1,6-Digalloylglucose: biosynthesis, 66 3-0-Digalloyl-1,2,4,6-tetra-O-galloyl-f3-D-glu-

cose: biosynthesis, 76 Digestible protein: quantification in plant

diet, 902 Dihydroflavanol reductase (DFR)

antisense, 307, 308 expression in transgenic L. corniculatus,

350 partial sequences in transgenic L.

corniculatus, 352 Dihydroflavonols

circular dichroism, 152, 153 enantioselective synthesis, 177 stereoselective synthesis, 147-155

920

(28, 3R)-Dihydrogenistein-(2a-7H28)-maesopsin, 245, 255, 256

Dihydrorobinetin,148 Dimeric flavanoid: conformational analysis, 509 Diosmetin (4'-methylluteolin), 428 Diospyros kaki (persimmon), 19

astringent proanthocyanidins, 761 2,2-Diphenyl-1-picryl-hydrazyl-hydrate

(DPPH): assay of plant antioxidants, 887,888,889

Dirigent protein antisense probes, 398 eDNA, 396 immunolabeling, 403, 405 localization, 403 mRNA expression, 400 stereoselective monolignol coupling, 396 tissue specificity of gene expression, 398

Dirigent protein mRNA expression in ray cells, 400 ray cells association, 400

Dry matter digestibility: quantification in plant diet, 902

Eisenia arborea, 20 Elk (Cervus elaphus roosevelti): diet, 897 Ellagic acid, 496 Ellagitannins

acyclic derivatives, 89 anticancer activity, 644-649 biogenesis, 32 biosynthesis, 84, 102 chemical synthesis, 106 chirality, 85 immunomodulatory effect, 649-661 interleukin production, 657-660 NMR bioassay, 93, 96 post coupling modifications, 88

H-Epicatechin, 173, 194, 203, 205, 215, 216, 235,485,510,581,596

antioxidant, 472-475, 490 bio-conversion by wood-rotting fungi, 566 flavonol intake, 490

Epicatechin-( 4/3, 8)-catechin antimicrobial activity, 586 leishmanicidal activity, 589

Epicatechin-(4/3, 8; 2B, 7)-epicatechin-(4, 8)­ent-epicatechin, 586, 589

Epicatechin-(4/3, 8; 2B, 7)-catechin-(4/3, 8)-epicatechin, 586, 589

Epicatechin-epicatechin-catechin, 491 Epicatechin-(epicatechin)2-catechin, 491 Epicatechin gallate: antioxidant activity, 472-

475,490 Epidemiological study

coronary heart disease, 472 flavonoid intake, 417-419

Subject Index

Epifisetinidol-(4/3, 6)-catechin, 586, 589 Epifisetinidol-(4/3, 8)-catechin, 586, 589 Epifisetinidol-(4/3, 6)-epicatechin, 586, 589 Epifisetinidol-(4/3, 8)-epicatechin, 586, 589 Epigallocatechin, 203,204, 207

anti-HIV, 205 antioxidant, 72-75

Epigallocatechin gallate anticancer properties, 629, 631, 632, 643 antioxidant activity, 490, 498 effect on platelet aggregation, 474 effect on LDL-oxidation, 473 plasma concentration, 475

Epigallocatechin 3-0-gallate antioxidant activity of derivatives, 766 dimerization with acetaldehyde, 763 radical scavenger, 766

(-)-Epigallocatechin -3-0-gallate, 27 Epitheaflagallin-3-0-gallate, 701 Epoxychalcones

absolute configuration, 149 cyclization, 151 epoxy opening, 149 stereoselective epoxidation, 149

Erwinia chrysanthemi, 547 Electron spin resonance (ESR):

phenylpropanoids, 438-447 Estradiol, 678, 680 Ethadridine: inhibition ofpoly(ADP-ribose)

glycohydrolase, 137 (NJ-EthyI-N-nitro-N-nitrosoguanidine,633 Etoposide, 681 Eucommia ulmoides, 684 Eugeniflorin D1: in Eugenia uniflora, 133 Euphorbin C: histamine suppression, 139 Euphorbin D, 620 Euphorbin E: from Euphorbia hirta, 129 Euphorbin I: from Euphorbia watanabei, 129 Eurobustin C: in Eucalyptus robusta, 135

Farnesene, 743 Fenton-type reactions, 497 Ferulic acid, 483, 486, 491 Fischer, Emil, 16 Fisetinidol-(4a, 6)-catechin, 586, 589 Fisetinidol-(4a, 8)-catechin, 586,589 Fisetinidol-(4/3, 8)-catechin, 586, 589 Flavan-3-o1s

oxidation in tea, 698 stereoselective synthesis, 155-160 synthesis, 29

Flavanol-aldehyde-anthocyanin adducts, 238 Flavanone-benzofuranoid, 245 Flavonoids

antioxidant properties, 728 antioxidant activity, 488-491 tea constituents, 698

Subject Index

Flavonol: acetaldehyde-induced polymeriza­tion, 238

Flavonol glycosides bioavailability, 419-424 metabolism, 424-428

Flavonol-rich foods, 417, 483 Flea beetles (Phyllotreta cruciferae), 868 ,870,

871 Forage legumes, 343 Forage nutritional quality: productivity con-

straints for elk and deer, 906 Forsythia intermedia, 675, 681, 683, 684, 687 Free radical, 884 Free radical scavengers, 884 French paradox, 726 Freudenberg, Karl, 16 Fucofureckol, 20 Fucus vesiculosus, 21 Fustin (dihydrofisetin), 147, 148, 563

Galangin, 484, 490 Gallic acid (3,4,5-trihydroxybenzoic acid), 43

apoptosis induction, 597, 600 biosynthesis in plants, 43, 55 13C-glucose labeling, 47 immunostimulating effect, 580 iron absorption, 550 iron deprivation, 547 NMR,47 fromPelargonium reniforme, 577 radical-ESR,600 retrobiosynthesis, 43 TNF inducer, 588

Gallocatechin, 577, 578 Gallocatechin-( 4' -O-7)-epigallocatechin, 194 Gallotannins, 645

biogenesis, 32 biosynthesis, 63

Galloyl orthoquinones, 107 Galloyl esters

biosynthesis, 30 oxidative coupling, 103 structural characteristics, 19

Galloyl-CoA: synthesis, 65 Galloylglucoses: biodegradation, 76 Gancaonin R, 262 Gancaonin S, 262 Gaultheria shallon, 825 Geissman, T.A. (Ted), 16 Gel permeation chromatography, 214, 569 GeminA,620 GeminD,607 Genistein, 271, 427, 428 Geraniin, 620

metabolic derivatives, 128 X-ray crystallography, 128

Geranium thunbergii, 128

Glepidotin A and B, 272 p-Glucogallin O-O-galloyl-p-D-glucose)

acyl donor, 66 biosynthesis, 30, 65 iron complex, 550 isolation, 30

Glucosyltransferase, 556-563 Glycyrrhiza lepidota, 272

921

Grape wine polyphenols: LC-ESI-MS, 234-237 Green tea

antitumor promotion, 629-640 aqueous non-dialysate enzymatic and chemical modification, 633-

634 Green tea polyphenols: anti-caries, 556, 558 Guibourtia coleosperma, 178

Hamamelitannin, 588 Haslam, Edwin

bibliography, 6 scientific career, 3

Hexahydroxydiphenoyl esters: structural characteristics, 19

Hexahydroxydiphenoyl (HHDP) group, 103 formation: atropisomer stereochemical con­

trol,108 synthesis, 112

Hirtellin B: antitumor activity, 127,644 Histamine release: inhibition by tannins, 139 Hop (Humulus lupulus), 739

cultivation, 739 hop acids, 742 hop oil, 743

Hops anticancer properties, 755 l3-acids transformations, 750 bitter taste, 747 estrogenic activity, 751-753, 756 foam head, 747 hop extracts, 747 hop polyphenols, 744 humulone (a-acids), 742 inhibition of gram-positive bacteria, 747 iso-a.-acids, 746, 747 iso-a.-acids: reduced, 748 lupulone (l3-acids), 742 proanthocyanidins, 744 sedative effect, 751

Howler monkey (Alouatta fusca), 883, 885 Humulene, 743 Hydrogen bonding, 521, 539, 565, 566 Hydrolyzable tannin

anti-HIV activity, 605 antimicrobial activity, 582 apoptosis, 597 cytotoxicity on tumor cell lines, 618-624 leishmanicidal activity, 588

922

Hydrophobic interaction, 521, 534, 539, 565, 566

Hydroxycinnamates, 483, 484, 486-489, 491, 577

Interaction between tannic acid and lipid vesi-cles

by absorbance measurement, 456, 461 dipole potential measurement, 457, 462, 464 electron density of egg yolks, 459, 462 electron microscopy, 456 X-ray diffraction, 457, 462, 466

Interferon, 576,590 Isobutyroyl-f3-D-glucoses: biosynthesis, 72 Isoflavanone-benzofuranoid, 247 Isotheaflavin, 700 Isotheaflavin-3'-O-gallate,701

Kaempferol (glycosides) absorption in man, 422 antioxidant activity, 488-490 content in black tea, 418 content in foods, 417

Kazinol C, 261 Kazinol E, 261 Kuwanon G, 279, 280,292, 295 Kuwanon H, 292, 295 Kuwanon I, 282 Kuwanon J, 282, 283, 285, 286, 288-290, 293 Kuwanon Q, 282, 283, 293 Kuwanon R, 282, 283, 289-293, Kuwanon V, 282, 283, 290, 291, 293

Lariciresinol, 681, 682, 684, Larix leptolepis (Karamatsu)

proanthocyanidin from, 558 taxifolin from, 563

LDL oxidation, 471-480 Leishmania donovani, 587 Leucoanthocyanidin reductases, 317 Leucocyanidin reductase, 317

in mutant L. japonicus, 327 Leucodelphinidin reductase, 317 Lignan,393

cancer chemoprevention, 675-681 metabolism by gastrointestinal flora, 677-

678 optical activity, 394 SOD activity, 604 subcellular localization, 405

Lignan biosynthesis, 681-688 dirigent protein, 396 ray cells, 407

Lignin anti-HIV activity, 608 apoptosis induction, 597 biosynthesis, 394

Subject Index

Lignin (cont.) monomeric composition, 394 radical-ESR, 602

Linalool, 743 Linum flavum, 675, 681, 686, 687 Linum usitatissimum (flax), 675, 677, 681,

684,686 Litchi polyphenols, 233-234 Loblolly pine (Pinus taeda), 843

constituent root tannin, 845 induced (stress) root tannin, 845, 851 root tannins, 843

Lotus corniculatus (bird's foot trefoil, sainfoin), 302

antisense chalcone synthase genes, 321 condendedtannins, 304 hairy roots, 303 hairy root transformation, 345

Lotus japonicus tannin accumulation, 328 transposon mutants, 324, 327

Lotus uliginosus, 871 Lupulin glands, 742 Luteolin, 416,

~acro~odel search, 528-539 ~aesopsin,247,255

Malus domestica, var. Kermerrien, 215 ~alvidin glucoside: S02 adduct N~R, 782 ~alvidin-3-glucoside, 238 ~ammalian lignan

cancer chemoprevention, 675-688 enterodiol,675-678 enterolactone, 675- 679, 681 secoisolariciresinol, 676--681, 688

~atairesinol, 676, 677, 679, 681--683, 686-688 ~ayer, Walter, 16 Medicago sativa (lucerne), 301 Melanoplus sanguinipes (grasshopper), 868,

869 ~ethyl gallate

antimicrobial activity, 582 antioxidant, 498 cytoprotective effect, 590 from Pelargonium reniforme, 577 TNF inducer, 588

~~2 energy calculation, 569 ~olecular modeling

complexation of catechin with L-proline­glycine oligomer, 535-538

self association of catechin, 529--535 Monotes engleri, 270 ~oraceae phenols

biosynthesis, 283-290 hypotensive action, 290--295 non-peptide bombesin receptor antagonists,

295

Subject Index

Moracin C, 282 Morus alba (mulberry tree), 272, 279

callus tissue, 282 Morusignin D, 270 Mouse epidermal JB6 cell, 631-635, 666, 669,

670-672 Mulberrofuran C, 283, 284, 285, 292, 292 Mulberrofuran E, 282, 283, 290, 291, 293 Mulberrofuran F, 292 Mulberrofuran G, 283, 284, 292, Myeloperoxidase, 608 Myrcene, 743 Myricetin, 484, 489, 490

~aringenin,426

(2R, 3S)-~aringenin-(3a-7)-(2S)-maesopsin, 245

~eotheaflavin, 700 ~eotheaflavin-3-0-gallate, 701 ~itric oxide (~O)

in apoptosis, 597 in Leishmania infection, 587

~uclear magnetic resonance (~MR) cider apple procyanidin, 217-219 intermolecular ~OE, 519-522, 531, 534,

535 oligomeric benzofuranoids, 247-249 prenylated phenols, 260-273 procyanidins, 194-198,511-523 338, 779, 788

~obotanin Band E, inhibition ofpoly(ADP­ribose) glycohydrolase, 607

~obotanin H, 644 ~obotanin K: inhibition ofpoly(ADP-ribose)

glycohydrolase, 137,607 ~ucleus exchange reaction, 559 Nuphar japonicum, 669 ~upharin C, 666, 669, 670, 672 ~utrition studies: labelled polyphenols, 358

Oenothein A, 645, 659, 660 Oenothein B, 498, 616

antitumor activity, 127,645,646,648,649, 654,656,659,660

cytotoxicity, 620, 622 dexamethasone antagonism, 137 effect on mouse mammary tumor virus

(MMTV),137 in Epilobium, 132 inhibitor ofpoly(ADP-ribose)

glycohydrolase, 138 in Oenothera, 132

Oenothera erythrosepala, 646 Onions, 416,417, 419,421,422,424,495 Oolong tea: anti-caries, 556, 558 Orthoquinones, galloyl-derived, 105 Oxidative coupling of galloyl groups, 106

923

Paeoniflorin: pentagalloylglucose solubility, 772

Particle board: formaldehyde zero emission, 805

Pasture bloat, 301 Paxanthonin,270 Pecan (Caraya illinoensis), 183 Pedunculagin: total synthesis, 112 Pelargonium sidoides (Umckaloabo), 577 Pelargonium reniforme, 577 1,2,3,4,6-Penta-O-galloyl-a-D-glucose, 452-

454,461-468 1,2,3,4,6-Penta-O-galloyl-I3-D-glucose, 666,

668,670,672 biaryl coupling, 85, 88 biosynthesis, 31, 69 conformation, 104 ellagitannin biosynthesis and

tellimagrandin II, 103 glucosyltransferase inhibition, 556 growth inhibition of Erwinia chrysanthemi,

548 iron complexation, 550 iron deprivation, 547 molecular modeling, 86

Phenoxy radical coupling in lignan biosynthesis, 681, 683, 684

Phlorotannins, 20 Phosphatidylcholine liposome: lipid

peroxidation inhibition, 768 Phycomyces blakesleeanus: gallic acid

biosynthesis, 47, 48, 53 Phyllanthusiin C

cytoprotective effect, 590 TNF inducer, 588

Pinoresinol, 682-686 Pinoresinol-Iariciresinol reductase, 684,

686 Pinus banksiana, 374 Pinus pinaster: free radical scavengers, 884 Pinus contorta, 148 Pinus parviflora, 601, 604 Pinus thunbergii (Kuromatsu), 558 Plant chemical defense

qualitative defense, 885 quantitative defense, 885

Plant 'tannase': ecological role, 79 Platelet aggregation, 474 Platypodium elegans (Leguminosae)

antioxidant activity, 888 how ler monkey diet, 886

Plicatic acid, 681, 683 Podophyllotoxin,681

5-methoxypodophyllotoxin, 684 Podophyllum hexandrum, 681 Poly(ADP-ribose) glycohydrolase: inhibition

by tannins, 137,607,608

924

Poly-L-Ieucine catalyst, 148, 149, 153 Polygalloyl glucose, 498 Polymerization degree of condensed tannins

byGPC,214 byMS,215 J3C_NMR, 214

by thioiysis, 213, 214 Polyphenol oxidase: tea-leaf, 26 Polyphenol-protein complex, 565, 567 Polyphenols

bioavailability, 357 biolabelling, 360 biosynthesis, 30 classification, 17 complexation, 18 molecular weight, 17 structural problems, 17 water solubility, 17

Potentillin, 644, 645 Prenylated eriodictyol, 267, 271, 272 Prenylated phenols

chemical shift variation of 5-0H proton, 263-272

chemical shift variation ofprenyl C-1, 260-263

Prenylxanthone, 270 Proanthocyanidin, see also Condensed tannins

(procyanidins) antimicrobial activity, 582, 586 antiviral activity, 204-206 biogenesis, 22 biosynthesis, 33 cider apple, 231-233 complement modulation, 198 electro spray ionization-MS (ESI-MS), 228-

239 extractable proanthocyanidins, 22 grape wine, 234-237 insoluble polymeric proanthocyanidins,

22 interflavanyl bond cleavage, 164-171 interflavanyl bond formation, 171-175 leishmanicidal activity, 589 litchi, 233, 234 NMR,194-198 0; scavenger, 604,605 radical, 602-603 rearrangement, 177-188 rotational isomerism, 194 structural characteristics, 18 superoxide radical scavenging activity, 202,

203 thiolysis, 181

Proanthocyanidin A-I [epicatechin-(4/3-8, 2/3-0-7)-catechin»)

biological activity, 203, 204, 207 NMR, 194, 199, 201

Subject Index

Proanthocyanidin A-2 [epicatechin-(4/3-8, 2/3-0-7)-epicatechin)

NMR, 194, 198, 199,201 biological activity, 203-204, 207

Proanthocyanidin oligomers glucosyltransferase inhibition, 564 synthesis, 563

Proapigeninidin, 564 Procyanidin, see also Condensed tannins

(proanthocyanidins) anti-HIV activity, 605 antioxidant activity, 491, 498 apoptosis induction, 597 dietary intake from wine, 733 radical-ESR, 602 SOD activity, 604 structures, 728

Procyanidin A-I: cleavage of interflavanyl bond,169

Procyanidin A-2 cleavage ofinterflavanyl bond, 169 ESI-MS, 233

Procyanidin B-1 [epicatechin-(4/3-8)­catechin)], 166, 167, 173, 174, 194, 195, 203 , 550, 601, 602-603

Procyanidin B-2 [epicatechin-(4/3-8)­epicatechin), 173, 174

biological activity, 203-207 NMR,194,199,201,202

Procyanidin B-3 [catechin-(4a-8)-catechin], 166, 167, 173

biological activity, 203-207 NMR,194,199,201,202

Procyanidin B-4 [catechin-(4a-8)-epicatechinl, 173,174

biological activity, 203-207 NMR,194,199,201,202

Procyanidin B-5 [epicatechin-(4/3-6)­epicatechinl

biological activity, 203-207 NMR,194,199,201,202

Procyanidin B-6 [catechin-(4a-6)-catechinl, 173

biological activity, 203-207 NMR,194,199,201,202

Procyanidin B-8 [catechin-(4a-6)-epicatechinl biological activity, 203-207 NMR,194,199,201,202

Procyanidin C-1 [epicatechin-(4/3-8)-epicat­echin-(4/3-8)-epicatechinl, 173, 194, 601-603

biological activity, 203-207 Procyanidin C-2, 174Prodelphinidins

formation of spirobenzofurans, 183 thiolytic cleavage, 181-187

Profisetinidin, 164, 166, 177-181,564 Prorobinetinidins, 164

Subject Index

Protein availability: seasonal availability, 904 Proteinases: hypermodulation, 875 Pseudopiptadenia contorta (Leguminosae):

howler monkey diet, 886 Pseudotsuga menziesii (douglas-fIr), 33, 148 Punicafolin, 85 Pycnoporus coccineus, 566

Quebracho (Schinopsis lorentzU), 164, 558 Quercetin (glycoside)

absorption in man, 421-424 antioxidant activity, 488-492 bioavailability, 419 content in back tea, 418 content in foods, 417 metabolism, 425-429

Quercus alba: callus tissue and ellagitannin production, 92

Ray parenchyma: heartwood constituents, 405 Red wine

absorption of flavonol glycosides, 421 polymeric pigments, 22

Revised structure albanins D and E, 272 broussoflavonols C and D, 261 isoprenoid substituted flavonoids, 272

Rhein 8-O-glucoside: proanthocyanidin solu­bility,772

Rhoipteleanin A: biogenesis, 770 Rhus typhina (sumac), 148

gallic acid biosynthesis, 53, 55 gallotannin biosynthesis, 76

Rhus succedanea, 563 Robinia pseudoacacia, 148 Rugosin A, 644, 645, Rugosin D, 103 Rutin, 419, 425, 426

Salal (Gaultheria shallon), 825, 826 condensed tannins, 839 condensed tannins, 825 ericaceous shrub, 826 proanthocyanidin assay, 827, 839 tree growth inhibition, 826 litter: tannin, 839

Salal tannins cross-polarization magic-angle spinning

(CPMAS) NMR, 828, 829 humus, 836 properties, 829

Salix sachalinensis, 563 Sanggenon C, 294 Sanggenon D, 294 Sanguiin H-5: total synthesis, 112 Schmidt, Otto, 16 Sesamolin, 4

925

Secoisolariciresinol dehydrogenase, 686, 687 Secoisolariciresinol diglucoside, 677, 678, 680,

681, 683, 686, Secoisolariciresinol diglucosyl transferase,

688 Self association of catechin, 521, 529 Shikimic acid derivatives, 582, 588 Siderophore, 547, Sinapic acid, 483, 486, 491 1-0-Sinapoyl-p-D-glucose: group-transfer po-

tential,67 Sorghum procyanidin: antioxidant, 498, 499 Streptococcus mutans, 556 Streptococcus sobrinus, 556 Supplemented diet

ascorbic acid, 500 sorghumtannin,499 tannic acid, 499 tocopherol acetate, 500

Tamarixinin A, 644 Tannins

anoxia indicator, 856 anthocyanidin assay, 857 antioxidants, 495-501 water solubility, 770 antisense anthocyanin genes, 321 carbon cycle, 853 concentration in plants, 855 geochemistry, 853 inhibition of organic matter degradation,

856 measuring techniques, 856 nutritional constraints for elk and deer, 902 quantiflcation, 90 quantitative impact on nutrient availability

for elk and deer, 902 Tannic acid

interaction with lipid bilayer, 452 preparation, 499 synthesized analog, 453, 454

Tannin: thermomechanical analysis, 813 Tannin autocondensation, 805, 818

electron spin resonance (ESR), 807 ionic hardeners, 811 radical reaction parameters, 809

Tannin cells, 310 Tannin degradation: mangrove leaves, 859 Tannin polycondensation, 806 Taxifolin (dihydroquercetin), 148, 194, 203,

204,207,564 Tea, see also Camellia sinensis

absorption of flavonol glycoside, 424 Tea fermentation

biochemistry, 711 oxidative enzymes, 713

Tea manufacture, 698

926

Tea polyphenols antiatherogenic effect, 471, 477 antioxidative effect on LDL, 472-474 inhibitory effect on platelet aggregation, 474

Tea aqueous non-dialysates antitumor promotion, 629-640 froTIl black tea, 630 cheTIlical constituents, 635-638 from green tea, 630 from oolong tea, 630 from pu-erh tea

Teaflavate B, 707 Tellimagrandin I

antitumor activity, 644-646 total synthesis, 112

Tellimagrandin II, 85 antitumor activity, 496, 644-646, 659-661 conformation, 104 molecular modeling-based synthesis analy­

sis, 108 total synthesis, 112

Teniposide, 681, Tetradecanoylphorbol-13-acetate (TPA), 631-

633,666,670,672 1,2,3,6-Tetra-O-galloyl-13-D-glucose, 548, 666,

668,670,672 biosynthesis, 68

Theacitrin, 707 formation mechanism, 708

Theaflavate A: epicatechin-3-0-gallate oxida­tion,706

Theaflavin, 27,498, 698-700 formation mechanism, 708 oxidation mechanism, 719

Theaflavin-3-0-gallate, 700 Theaflavin-3,3' -O-digallate, 700 Theaflavin-3'-O-gallate, 700 Thearubigin, 26,27, 698, 708 Theobroma cacao, 194, 225 Thuja heterophylla (western hemlock), 675,

681,684,686 Thuja plicata (western red cedar), 675, 681,

684,686 Transactivator genes, 345 Trapanin A, 620 Trapanin B, 607 Trifolium repens (white clover), 301 1,2,6-Tri-O-galloyl-13-D-glucose

biosynthesis, 67, 69 iron complex, 550

3-0-Trigalloyl-1,2,4,6-tetra-O-galloyl-J3-D-glu­cose: biosynthesis, 76

Trolox,441,486,491,500 Tumor necrosis factor (TNF), 576, 587

Subject Index

UDP-glucose glucosyltransferase, 688 UDP-glucuronosyl transferase, 428, 429 UDPG: conneryl alcohol glucosyltransferase,

371 cambial growth, 386 cinnamyl aldehyde glucosylation, 381 isoelectric focusing, 377 N-terminal sequence, 379 seasonal activity, 374 substrate specificity, 378 xylogenesis, 374

Umckaloabo antibacterial activity, 579 flavan-3-ols, 577 immunostimulating effect, 580

Vaccinium vitis-idaea, 194 Vegetable tannery biosolids: organic fertilizer,

791 Vegetable tanning

biosolids "delisting", 792,802 biosolid waste products, 791 wastewater, 791

Vegetable tannins: deImition, 17 Vescalagin

iron deprivation, 547 growth inhibition of Erwinia chrysanthemi,

548 Vitis vinifera

anthocyanin NMR assignments, 781 free radical scavengers, 884 3-0-13-D-glucosyl malvidin, 781

Vitisin, 786

VVeinges,EJaus,16 VVestern hemlock (Tsuga heterophylla), 825 VVestern red cedar (Thuja plicata), 825 VVine

consumption and coronary disease, 725 flavonoid levels, 731 low-density lipoprotein (LDL)-oxidation pro-

tection, 728 VVood-rotting fungi, 566 Woodfordia fruticosa, 646 VVoodfordin: in Lythraceae, 132 VVoodfordin C: antitumor activity, 127,616-

624 Wyethia helenioides, 267

Xanthohumol, 754

Zeyhe~ 175,175,245,254