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SUPPORTING INFORMATION Natural stilbenes: an overview

Tao Shen, Xiao-Ning Wang and Hong-Xiang Lou*

Department of Natural Product Chemistry, School of Pharmaceutical Sciences, Shandong University, 44 West Wenhua Road, Jinan 250012, P. R. China. E-mail: [email protected]; Tel: +86-531-88382012; Fax: +86-531-88382019.

The ‘Supporting Information’ is a supplementary material for the section ‘4 Distribution’ to illustrate the distribution and chemical structures of 400 new stilbenes isolated during the period of 1995 to 2008.

The ‘Supporting Information’ was composed of ten parts: Table S1 Distribution of monomeric stilbenes isolated from 1995 to 2008 Table S2. Distribution of oligomeric stilbenes isolated from 1995 to 2008 Figure S1 Chemical structures of monomeric stilbenes (1-125) isolated from 1995 to 2008 Figure S2 Chemical structures of oligomers (126-303) isolated from 1995 to 2008 Figure S3 Chemical structures of oligomers (304-325) isolated from 1995 to 2008 Figure S4 Chemical structures of piceatanol oligomers (326-335) isolated from 1995 to 2008 Figure S5 Chemical structures of oligomers (335-340) isolated from 1995 to 2008 Figure S6 Chemical structures of resveratrol and oxyresveratrol oligomers (341-354) isolated from 1995 to 2008 Figure S7 Chemical structures of miscellaneous oligomers (355-400) isolated from 1995 to 2008 Reference

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Table S1. Distribution of monomeric stilbenes isolated from 1995 to 2008 Family Species Compounds Ref

Aceraceae Acer mono 5-O-methyl-(E)-resveratrol 3-O-β-D-glucopyranoside 22 14 5-O-methyl-(E)-resveratrol 3-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside 23 Anchinoidae Kirkpatrickia variolosa 3,4,5-triacetoxystilbene 19 11 Asteraceae Leuzea carthamoides (E)-3,3'-dimethoxy-4,4'-dihydroxystilbene 14 8 Bombycidae Bombyx batryticatus BB-2 93 50 Burseraceae Boswellia papyrifera trans-4',5-dihydroxy-3-methoxystilbene-5-O-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyrano 15 side 24, trans-4',5-dihydroxy-3-methoxystilbene-5-O-α-L-rhamno pyranosyl- (1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside 25 Combretaceae Combretum erythrophyllum combretastatin A-1 2'-β-D-glucoside 1 1 Cyperaceae Carex distachya carexanes A-C 109-111 57 carexanes D-G 112-115 58 Dipterocarpaceae Hopea utilis resveratrol-10-C-β-glucopyranoside 27 20 Shorea hemsleyana resveratrol-12-C-β-glucopyranoside 29 21 Upuna borneensis piceid 2'-O-p-hydroxybenzoate 38, piceid 2'-O-E-ferulate 39 28 Euphorbiaceae Macaranga mappa mappain 52 36 M. schweinfurthii schweinfurthins A-C 49-51 35 M. alnifolia schweinfurthins E-H 53-56 37 Gnetaceae Gnetum africanum gnetifolin K 26 18 G. gnemonoides gnetifolin K 26 18 G. gnemon gnetifolin K 26 19 G. klossii gnetofurans B-C 73-74 43 G. montanum stemofuran B (gnetifolin M) 78 46 gnetumelin B 75 and C 41 23 G. parvifolium gnetifolin K 26 17 Hepaticae Corsinia coriandrina corsifurans A-C 88-90 47 Iridaceae Iris halophila halophilol A 11 6 Leguminosae Cicer bijugum cicerfuran 92 49 (Fabaceae) Dalea purpurea pawhuskins A-C 61-63 40 Elephantorrhiza goetzei 5-methoxy-E-resveratrol 3-O-rutinoside 24 16 Erythrina addisoniae 2'-O-demethylbidwillol B 98, addisofurans A-B 99-100 53 Erythrina burttii burttinol D 101 54 Guibourtia tessmanii (E)-3,4'-dimethoxyl-5-rutinosyl stilbene 20 12 3,5-dimethoxy-4'-O-(β-rhamnopyranosyl-(1→6)-β-glucopyranoside)stilbene 21 13 Lespedeza uirgata lespedezavirgatol 91 48 Lonchocarpus chiricanus chiricanines A-E 64-68 41 L. utilis 4-hydroxy-5'-methoxy-6'',6''-dimethylpyran[2'',3'':3',4']stilbene 45 33 3,5'-dimethoxy-4-hydroxy-6'',6''-dimethylpyran[2'',3'':3'',4']stilbene 46 3,4,5-trimethoxy-6 '',6''-dimethylpyran[2'',3'':3',4']stilbene 47 Machaerium multiflorum machaeriols A 60 and B 104 39 Sphaerophysa salsula trans-4-[2- (3,5-dimethoxyphenyl)ethenyl]-1,2-benzenediol 2 2 Lejeuneaceae Marchesina bongardiana 3,4-dihydroxy-3'-methoxystilbene 18 10 Liliaceae Schoenocaulon officinale schoenoside 76 44

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Meliaceae Ekebergia benguelensis 5-[(1E)-2-(4-hydroxyphenyl)ethenyl]-4,7-dimethoxy-3-methyl-2H-1-benzopyran-2-one 69, 42 5-[(1E)-2-(4β-D-glucopyranosyloxyphenyl)ethenyl]-4,7-dimethoxy-3- methyl-2H-1-benzopyran-2-one 70, 1-{2-hydroxy-6-[(1E)-2-(4-hydroxyphenyl) ethenyl]-4-methoxyphenyl}-2-methyl-1-propanone 71, 1-{2,4-dihydroxy-6-[(1E)- 2-(4-hydroxyphenyl)ethenyl]-phenyl}-2-methyl-1-propanone 72 Moraceae Artocarpus akoocha akoochins A-B 96-97 52 A. fretessi artoindonesianins X-Y 102-103 55 A. gomezianus artoindonesianins N 42 and O 95 30 A. incisus artocarbene 48 34 A. integer trans-4-isopentenyl-3,5,2',4'-tetrahydroxystilbene 43, artocarbene 48 31 A. petelotii artopetelin D-G 105-108 56 Chlorophora excelsa 4-[(2''E)-7''-hydroxy-3'',7''-dimethyloct-2''-enyl]-2',3,4',5-tetrahydroxy-trans-stilbene 44 32 Morus cathayana sanggenofuran B 94 51 Ophioglossaceae Helminthostachys zeylanica ugonstilbenes A-C 57-59 38 Orchidaceae Pholidota yunnanensis phoyunbenes A-D 7-10 5 Phragmipedium calurum 2,3'-dihydroxy-5'-methoxystilbene 4, 2,3-dihydroxy-3',5'-dimethoxystilbene 5 4 P. hybrid 2,3'-dihydroxy-5'-methoxystilbene 4, 2,3'-dihydroxy-5,5'-dimethoxystilbene 6 4 P. longifolium 2,3'-dihydroxy-5'-methoxystilbene 4 4 Thunia alba thunalbene 3 3 Polygonaceae Calligonum leucocladum (E)-resveratrol 3-O-β-D-xylopyranoside 33 26 (E)-resveratrol 3-(6-galloyl)-O-β-D-glucopyranoside 34 (E)-resveratrol 3-(4-acetyl)-O-β-D-xylopyranoside 37 Eskemukerjea megacarpum (E)-3, 5, 3', 4'-tetrahydroxystilbene 3-O-β-D-(6-O-galloyl)glucopyranoside 30, 22 (E)-3, 5, 4'-trihydroxystilbene 3-O-β-D-(6-O-syringyl)glucopyranoside 31 Pleuropterus ciliinervis pieceid-2''-O-gallate 35, pieceid-2''-O-coumarate 36 27 Polygonum cuspidatum 1-(3',5'-dihydroxyphenyl)-2-(4''-hydroxyphenyl)-ethane-1,2-diol 40 29 116-125 59 Rumex bucephalophorus 5,4'-dihydroxy-3-methoxystilbene 12, 3,5-dihydroxy-4'-methoxystilbene 13 7 5,4'-dihydroxystilbene-3-O-α-arabinopyranoside 32 24 Rosaceae Holodiscus discolor (E)-resveratrol 3-O-β-D-xylopyranoside 33 25 Stemonaceae Stemona collinsae stemofurans A-K 77-87 45 Zingiberaceae Alpinia katsumadai (Z)-3-methoxy-5-hydroxystilbene 15, (Z)-3,5-dihydroxystilbene 16 9 (E)-1-(1-terpinen-4-olyl)-3-methoxystilbene 17

Compounds 28 and 29 were obtained from commercial Riesling wine. See Ref 162.

Table S2. Distribution of oligomeric stilbenes isolated from 1995 to 2008 Family Species Compounds Ref Agavaceae Yucca gloriosa gloriosaols A 399 and B 400 161 Y. schidigera yuccaols A-C 393-395 158 yuccaols D-E 396-397 159 yuccaone A 398 160 Apiaceae Foeniculum vulgare foeniculosides X 230 and XI 231 112 Arecaceae Aiphanes aculeate aiphanol 327 144 Syagrus romanzoffiana 13-hydroxykompasinol A 378, scirpusin C 379 157

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Celastraceae Salacia lehmbachii lehmbachols A 310, B 311, C 312 and D 309 134 Cyperaceae Carex pendula cis-miyabenol A 289 129 Cyperus longus longusone A 328, longusols A 365, B 366 and C 329 145 Kobresia nepalensis nepalensinols A 232, B 264 and C 233 113 nepalensinols D 234, E 277, F 265 and G 266 114 Dipterocarpaceae Dipterocarpus grandiflorus isoampelopsin F 155, (-)- 162, shorealactone 167, vaticanols B 245 and C 79 239, hemsleyanol D 255, grandiphenols A-B 275-276 Dryobalanops oblongifolia cis-diptoindonesin B 228, trans-diptoindonesin B 229 111 Hopea exalata hopeanol 129 63 hopeanolin 219 109 H. hainanensis hopeanol B 130, hopeahainols A 131 and B 132 64 H. malibato malibatols A 165 and B 376, dibalanocarpol 263 83 H. parviflora parviflorol 127, (-)-ampelopsin A 162 61 H. utilis hopeafuran 160, malibatol A 165, vaticanol B 245, isohopeaphenol 256 20 Neobalanocarpus heimii heimiol A 159, vaticaphenol A 244 81 Shorea hemsleyana hemsleyanols C 254, D 255 and E 128, hemsleyanosides E 205 and F 164 62 shorealactone 167 85 hemsleyanols A 163 and B 215, (+)-α-viniferin-13b-O-β-glucopyranoside 216 21 Upuna borneensis isoampelopsin F 155, vaticanols B 245 and C 239, upunaphenol A 297 78 upunosides A 296, B 204, C 158 and D 184 80 upunaphenols B 262, C 274, D 291 and E 192 98 upunaphenols G 252 and F 253 120 Vateria indica vaticanols B 245 and C 239, vaticasides B-C 250-251, isohopeaphenol 256, vateriaphenols 116 A 303 and B 259 Vatica diospyroides vatdiospyroidol 242, vaticaphenol A 244 115 V. oblongifolia vaticaphenol A 244, A 257, isohopeaphenol A 258 117 V. pauciflora isoampelopsin F 155, hemsleyanols A 163, C 254 and D 255, pauciflorosides A 183, B 77 221 and C 222, vaticanols A 195, B 245, C 239, E 196 and G 193, vaticaside D 194, pauciflorols A 197, B 198 and C 260, stenophyllol B 220, isovaticanols B 246 and C 240, vateriaphenol B 259 pauciflorols D 302 and E 161 82 V. rassk vaticanols A 195, B 245 and C 239 100 vaticanols D 298 and G 193, vaticaside D 194, vaticanols H-J 299-301 99 vaticanols E 196 and F 241, vaticasides A 203, B 250 and C 251 101

Gnetaceae Gnetum africanum gnetuhainins A 345, C 330, D 176, E 342 and F 318 92 gnemonosides A 177, B 181, H 180, I 343 and J 349 18 bisisorhaphontigenin B 322, longusol A 365, gneafricanins A 370 and B 372 141 G. gnemon gnemonosides A 177, B 181 and K 225, gnemonols K 226, L 227 and M 317, latifolol 367 19 gnemonols A 355 and B 290 60 gnemonols G 344, H 358, I 356 and J 357 151 gnemonols D-F 359-361 154 G. gnemonoides gnetal 126, gnemonoside E 182, 2b-hydroxyampelopsin F 351, gnemonol C 364 60 gnemonosides A 177, B 181, C 178 and D 179 93 gnemonosides F 223, G 224 and H 180 18

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G. hainanense gnetuhainins A 345, B 346, C 350, D 347 and E 348 152 gnetuhainins F 321, G 373, H 374, I 314 and J 369 137 gnetuhainins P 313, Q 368, L 371 and K 375 136 gnetuhainins M 363, N 323 and O 324 142 gnetuhainin P 313 135 gnetuhainins R 325 and S 354 143 gnetuhainin S 354 153 G. klossii gnetofuran A 308, latifolol 367 43 G. latifolium latifolol 367 155 G. moutanum gnetumontanins A 340, B 362, C 304 and D 305, shegansu B 319 131 gnetifolins M 315 and N 316 138 gnetumelin A 326 23 G. pendulum gnetupendins A-B 306-307 132 shegansu B 319, gnetupendins C 341 and D 320 133 G. parvifolium 2b-hydroxyampelopsin F 351, parvifolols A 352, B 353, C 339 and D 319 140 Haemodoraceae Anigozanthos preissii anigopreissin A 171 88

anigopreissin A 171, anigopreissin A-4a-O-β-D-glucopyranoside 172, anigopreissin 89 A-4b-O-β-D-glucopyranoside 173, anigopreissin A-4a,4b-di-O-β-d-glucopyranoside 174

Iridaceae Belamcanda chinensis shegansu B 319 139 Iris halophila halophilol B 293 6 Leguminosae Caragana rosea cararosinol A 273 125 (Fabaceae) C. sinica (+)-isoampelopsin F 156, (-)-ampelopsin F 157, caraphenols A 217, B 147 and C 148 72 carasinols A-C 270-272 124 C. stenophylla caragaphenol A 218 108 C. tibetica tibeticanol 331 146 Maackia amurensis 7-epi, 8'-epi, 11-de-O-methyl-5'-methoxygnetifolin F 377 156 Sophora leachiana leachianols C 238, D 209, E 210, F 141 and G 142 69 S. davidii davidiols A 207, B 208 and C 243 105 S. stenophylla stenophyllol B 220 110 Moraceae Artocarpus gomezianus andalasin A 337, artogomezianol 338 150 Morus alba alboctalol 336 148 M. macroura andalasin A 337 149 Musaceae Musa cavendish anigopreissin A 171 88 Orchidaceae Phragmipedium calurum (E)-3'-hydroxy-2'-(4-hydroxybenzyl)-5'-methoxystilbene 384 4 (E)-5'-hydroxy-2'-(4-hydroxybenzyl)-3'-methoxystilbene 385 (E)-2,3'-dihydroxy-2'-(4-hydroxybenzyl)-5'-methoxystilbene 386 (E)-2,5'-dihydroxy-2'-(4-hydroxybenzyl)-3'-methoxystilbene 387 (E)-2,3'-dihydroxy-2'6'-bis(4-hydroxybenzyl)-5'-methoxystilbene 388 P. hybrid (E)-5'-hydroxy-2'-(4-hydroxybenzyl)-3'-methoxystilbene 384 4 (E)-2,5'-dihydroxy-2'-(4-hydroxybenzyl)-3'-methoxystilbene 385 (E)-2,3'-dihydroxy-2'6'-bis(4-hydroxybenzyl)-5'-methoxystilbene 388 (E)-2,3-dihydroxy-2'-(4-hydroxybenzyl)-3',5'-dimethoxystilbene 389 (E)-2-hydroxy-2'-(4-hydroxybenzyl)-5,3',5'-dimethoxystilbene 390 phragmidimers A 391 and B 392

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P. longifolium (E)-3'-hydroxy-2'-(4-hydroxybenzyl)-5'-methoxystilbene 384 4 (E)-5'-hydroxy-2'-(4-hydroxybenzyl)-3'-methoxystilbene 385 (E)-2,3'-dihydroxy-2'-(4-hydroxybenzyl)-5'-methoxystilbene 386 (E)-2,5'-dihydroxy-2'-(4-hydroxybenzyl)-3'-methoxystilbene 387 (E)-2,3'-dihydroxy-2'6'-bis(4-hydroxybenzyl)-5'-methoxystilbene 388 phragmidimer B 392 Pinaceae Picea abies piceasides A-B 332-333, piceasides G-H 334-335, piceasidesC-F 380-383 147 Polygonaceae Polygonum cuspidatum 153, 154 75 Rheum maximowiczii maximols A 188 and B 187 95 Ranunculaceae Paeonia suffruticosa suffruticosols A-C 200-202 103 Vitaceae Ampelopsis sinica sinicin A 249 119 Cyphostemma crotalarioides cyphostemmins A-B 136-137, parthenocissin A 138 66 Cissus quadrangularis 137, quadrangularins B-C 139-140 68 Parthenocissu quinquefolia parthenocissins A 138 and B 235 67 P. tricuspidata parthenostilbenins A 143 and B 144 70 isoampelopsin F 155 76 Vitis. amurensis amurensins A 149 and B 211 73 amurensins C 212, D 213, E 294 and F 295 106 amurensin G 199 102 amurensin H 175 90 amurensins I 261, J 279, K 280, L 281 and M 269 122 285 and cis-vitisin B 286 86, 128 V. betulifolia betulifols A 170 and B 169, heyneanol A 292 87 V. coignetiae ε-viniferin diol 168, vitisin B 285 and cis-vitisin B 286 86 vitisins D 267 and E 214 107 V. davidii davidol A 268 123 V. flexuosa flexuosol A 278 126 V. heyneana heyneanol A 292 130 V. thunbergii vitisinols A 134, B 166, C 133 and D 135 65 V. vinifera resveratrol (E)-dehydrodimer 11-O-β-D-glucopyranoside 189, resveratrol 96 (E)-dehydrodimer 11'-O-β-D-glucopyranoside 190 (-)- 191, vitisin C 287 97 (+)-viniferols B 247 and C 248 118 malibatol A 165, isohopeaphenol 256, (+)-viniferol A 288 84 (+)-viniferol D 206 104 (+)-vitisifuran A 283, (-)-vitisifuran B 282, viniferifuran 175 91 isohopeaphenol 256 121 (+)-viniferethers A 145 and B 146 71 V. ssp restrytisols A-C 150-152 74 r-2-viniferin 284 127 Welwitschiaceae Welwitschia mirabilis mirabilosides A-B 185-186, mirabilols A-B 236-237 94

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Figure S1 Chemical structures of monomeric stilbenes (1-125) isolated from 1995 to 2008

OMe R3 3 R1=R2=R4=R5=H, R3=OH,R6=Me 1 2 3 5 4 6 MeO R2 R4 4 R =R =R =R =H, R =OH,R =Me 5 R1=R2=H, R3=R4=OH, R5=Me,R6=Me 1 2 3 4 5 6 OGlc OH OR6 6 R =OMe, R =R =H, R =OH, R =H,R =Me MeO R R1 7 R1=R5=H,R2=R4=OMe,R3=OH,R6=Me OMe 8 R1=R5=H,R2=OH,R3=OMe,R4=OMe,R6=Me OH OH 9 R1=R2=R5=H,R3=OH,R4=OMe,R6=Me 1 2 5 3 4 6 OMe OR5 10 R =R =R =H,R =OMe,R =OMe,R =Me 12 R1=R3=R4=H,R2=OH,R5=H,R6=Me 1 2 R=OMe 1 3 4 2 5 6 18 R=H 13 R =R =R =H,R =OMe,R =R =H

OR

OH OCH3 MeO HO HO MeO

MeO OH OH OCH3 15 R=Me 11 14 16 R=H

OR1 OR2 OMe

OR2 O 1 O R O O OH OH 3 OR OH OR3 1 2 3 19 R1=R2=R3=Ac 22 R =Me,R =R =H 17 1 2 3 20R1=rutinosyl,R2=R3=Me 23 R =Me,R =apiose,R =H 1 2 3 1 2 3 24 R =Me,R =Rha,R =H 21 R =R =Me,R =rutinosyl 1 2 3 30 R1=R3=H,R2=Ara 25 R =Me,R =R =Rha 34 R1=R3=H,R2=galloyl 33 R1=R3=H,R2=Xyl 35 R1=R2=H,R3=galloyl 36 R1=R2=H,R3=

2 OH R O OGlc HO HO 8 OH OH 7 OMe HO R1 R2 OGlc OH OR1

1 2 26 27 R =Glc,R =H,H-7/8=trans 31 R1=(6-O-galloyl)glc,R2=OH 1 2 28 R =Glc,R =H,H-7/8=cis 32 R1=(6-O-syringyl)glc,R2=H 29 R1=H,R2=Glc,H-7/8=trans

HO OH OH OH OH

HO OH O O O O O OH OH OH 40 OH OH OH O OR HO OH O 37 38 R=p-hydroxybenzoyl OH 39 R=E-feruloyl MeO

OH 41 OH

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R5

HO HO R1 R2 OH OH O

OH R3 R4 OMe OH 42 43 45 R1=R2=R4=H,R3=OH,R5=OMe 46 R1=R4=H,R2=R5=OMe,R3=OH 47 R1=R5=H,R2=R3=R4=OMe 48 R1=R3=R5=OH,R2=R4=H HO

OH OH OH OH HO

OH OH

44

OH

OR2 R R1 O

51 R=CH2CH=CHMe2 HO OH 52 R=H H

OMe OH HO O

3 R O 1 2 3 HO 49 R =OH, R =H, R =CH2CH=CHMe2 H 1 2 3 50 R =OH, R =Me R =CH2CH=CHMe2 OH 53 R1=OH, R2=Me, R3=H 54 R1=H, R2=Me,R3=H 56 OH 55 R1=R2=H,R3=H

OH OH OH H

HO O HO

OH OH OH

57 58 59

HO HO OH H OH O HO HO H O OH OH 60 61 62

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HO OH HO OH OH HO O R2

OH OR1

63 64 R1=R2=H 65 1 2 66 R =Me,R =CH2CH=CHMe2

HO OMe OR O O

O HO OH OH O OMe OR O OH

67 68 69 R=H 71 R=Me 70 R=Glc 72 R=H

OMe OH R4 R3 OH HO MeO

R2 R O HO O O OH OR1 OGlc 73 R1=Me, R2=R4=H,R3=OH 76 77 R=H 79 R=Me 74 R1=R2=R4=H,R3=OH 75 R1=R3=H, R2=R4=OMe

R1 OH R1 OH OH Me OR1 Me OR2 Me R2 Me Me O O O R3 OMe R2 OMe R3 OMe

78 R1=R2=R3=H 83 R1=R2=H 86 R1=OH,R2=Me,R3=H 1 2 3 1 2 80 R =Me,R =R =H 84 R =H,R =Me 87 R1=R2=H,R3=Me 81R1=R2=Me,R3=H 85 R1=Me,R2=H 82 R1=R2=R3=Me

RO H3CO

OCH3 OCH3 O O OH 88 R=Me 90 89 R=H

HO O MeO O HO O OH OH

O OCH3 O OH O HO HO O OMe MeO OMe 93 91 92

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OH OH OMe

HO O R1O O HO O OH OR2 OMe

94 R1=Me, R2=H 95 R1=H, R2=Me 96

97

OH OH OH HO O HO O HO O HO H3CO H3CO

98 99 100

OH OH OH HO O MeO HO O O O OH 101 OH

OH H

102 103 O O H

104

OH OH OH OH OH O

O OH O O HO O HO HO O H O O O

105 106 107 108

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R5O 8 OR6 7 R1O

O O OR3 OH H OR2 R3 OR4

1 2 3 4 5 6 116 R =SO3M,R =R =R =R =R =H,H-7/8=trans MeO 1 3 4 5 6 2 R2 117 R =R =R =R =R =H,R =SO3M,H-7/8=trans 1 1 2 3 5 6 4 R 118 R =R =R =R =R =H,R =SO3M,H-7/8=trans 1 2 3 4 6 5 1 2 3 119 R =R =R =R =R =H,R =SO3M,H-7/8=trans 109 R =β-OH,α-H,R =β-H,R =H 1 2 3 4 5 6 1 2 3 120 R =R =R =R =R =H,R =SO3M,H-7/8=trans 110 R =O,R =α-OH,R =H 1 2 3 4 5 6 1 2 3 121 R =SO3M,R =R =R =R =R =H,H-7/8=cis 111 R =O,R =β-OH,R =H 1 3 4 5 6 2 1 2 3 122 R =R =R =R =R =H,R =SO3M,H-7/8=cis 112 R =O,R =β-H,R =H 1 2 4 5 6 3 1 2 3 123 R =R =R =R =R =H,R =SO3M,H-7/8=cis 113 R =O,R =β-H,R =OH 1 2 3 5 6 4 1 2 3 124 R =R =R =R =R =H,R =SO3M,H-7/8=cis 114 R =O,R =α-OH,R =OH 1 2 3 4 5 6 1 2 3 125 R =R =R =R =R =H,R =SO3M,H-7/8=cis 115 R =O,R =β-OH,R =OH M=Na or K

Figure S2 Chemical structures of resveratrol oligomers (126-303) isolated from 1995 to 2008

RO HO HO

HO HO OH O H OH H OH O CHO HO O O 8a HO OH HO H HO OH HO O O OR O O HO OH O OH OH

126 127 H-8a=β 129 R=CH3 131 R=H 128 H-8a=α 130 R=H 132 R=CH3

HO HO HO OH H O H O H H O O HO H H HO H H HO OH

OH O OH OH OH 133 134 135

HO RO OH H 8a HO OH H OH OH OH HO HO H HO H H OH OH H OH H OH OH OH OH OH OH OH

HO OH 139 R=CH2Me, 8aS OH OH 140 R=CH2Me, 8aR 141 R=H, 8aS 136 137 138 142 R=H, 8aR 143 R=Me, 8aS 144 R=Me, 8aR

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OH OH OH R2 1 O R O HO HO OH H H H OH HO HO HO H H OH OH H H H H H HO OH OH OH OH HO

HO OH HO OH OH OH OH 1 2 145 R =OMe,R =H 147 148 149 146 R1=H,R2=OMe

OH GlcO OH GlcO OH HO OH HO OH HO H H H H O 7a H HO HO 8a OH H HO OH H H OH OH H H

HO OH OH OH OGlc OH OGlc OH 150 H-7a=β,H-8a=α 152 153 154 151 H-7a=α,H-8a=β

OH HO HO OH R HO OH H O OH HO O OH 7a 7a H 8a HO H 8a HO 7a H HO H 8b H H H H 8b H 8a HO O 7b O OH H H OH H OH OH HO OH HO OR OH 155 R=H,H-7a=H-7b=β,H-8a=H-8b=α 159 OH 156 R=H,H-7a=H-8a=H-7b=β,H-8b=α 160 161 H-7a(β) and H-8a(α)=dihydro 162 R=H,H-7a=α,H-8a=H-8b=β 157 R=H,H-7a=H-7b=α,H-8a=H-8b=β 163 R=H,H-7a=H-8b=β,H-8a=α 158 R=Glc,H-7a=H-8a=H-8b=α,H-7b=β 164 R=Glc,H-7a=α,H-8a=H-8b=β 165 R=H,H-8b=β, 7a,8a-didehydro

HO HO HO H O OH H H O OH O OH 7a OH O HO 8a H OH HO HO H H HO H H OH O H H OH H O HO H H H OH O OH O OH H H O O HO CHO HO OH H 170 OH 167 OH 166 168 H-7a=β,H-8a=α 169 H-7a=α,H-8a=β

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HO R1O OR2 O OH HO OH O H HO O HO HO OH H OH OH OH 171 R1=R2=H OH 172 R1=Glc,R2=H 176 173 R1=H,R2=Glc OH 174 R1=R2=Glc 175

R1O OR1 RO H O OR2 H OH O OGlc H HO HO HO 7b H 8b H O 7b H 8b OH R3O OR2 OH

177 R1=H,R2=R3=Glc,H-7b/8b=trans 1 2 3 178 R =R =H,R =Glc,H-7b/8b=trans OR3 179 R1=R3=H,R2=Glc,H-7b/8b=trans OR 1 3 2 180 R1=R2=R3=Glc,H-7b/8b=trans 182 R =R =Glc,R =H,H-7b/8b=trans 1 3 2 185 R=Glc 181 R1=H,R2=R3=Glc,H-7b/8b=cis 183 R =R =H,R =Glc,H-7b/8b=trans 186 R=H 184 R1=R3=H,R2=Glc,H-7b/8b=cis

HO HO HO H H H O OH O O 7a 8a HO 8b HO 8a OH HO OH H H CHO H 7b H

OH O OH OH OR1 OR2 H HO 187 H-8a=β,H-7b/8b=cis 189 R1=Glc,R2=H 188 H-8a=α,H-7b/8b=trans 190 R1=H,R2=Glc 191 H-7a=α,H-8a=β 192 H-7a=β,H-8a=α

HO OH HO HO OH H H OH O OH R2 O OH 7a HO HO H H 1 HO H OR OH OH H 8b 8c H 8c H 7c H 7c H 7b H 7b H OH H OH H HO OH H H H OR OH OH H OH OH

195 R1=R2=H,H-7b=H-8c=α,H-7c=H-8b=β 199 H-7a=H-8c=H-7b=β,H-7c=α OH 196 R1=R2=H,H-7b=H-8b=H-8c=β,H-7c=α 200 H-7a=H-8c=α,H-7b=H-7c=β HO 201 H-7a=H-7b=H-8c=α,H-7c=β 197 R1=R2=H,H-7b=H-8b=H-7c=α,H-8c=β 198 R1=R2=H,H-7b=H-8b=H-8c=α,H-7c=β 193 R=H 1 2 194 R=Glc 203 R =Glc,R =H,H-7b=H-8c=α,H-8b=H-7c=β 204 R1=Glc,R2=H, H-7b=H-8c=β,H-8b=H-7c=α 205 R1=H,R2=Glc,H-7b=H-8b=H-7c=α,H-8c=β

13 Electronic supplementary information (ESI) for Natural Product Reports

OH HO OH H H HO O O OH OH HO O 7a H H H OH HO OH H HO H H 7b 7c H H H OH HO 8c H H OH H H OH H OH H H OH HO OH HO HO OH OH OH OH 202 206 H-7a=H-8c=β,H-7b=H-7c=α 208 207 H-7a=H-8c=α,H-7b=H-7c=β

HO OH HO OH HO HO OH 7c H OH O O HO H HO 7a H O 8c 7c HO 8a 8c O HO OH H A2 H H H H H H OH OH H H

HO HO OH OH OH OH OH

209 210 211 H-7a(α) and H-8a(β)=dihydro,H-8c=β 212 H-8c=β 213 H-8c=α OH OH HO OH H H H O O O OH OH HO OH H HO O H H R H H H O H H O OH OH H HO H HO H H 8c H 7c HO OH O OH OH HO OH OR 218 214 R=H 216 R=Glc 215 R=OH 217 R=H, 7c,8c-didehydro

H O OH HO H O OH OH OH HO HO H H H H H HO H H O H OH H H OR1 O O O R2O HO

HO 220 R1=R2=H 219 221 R1=H,R2=Glc 222 R1=Glc,R2=H

14 Electronic supplementary information (ESI) for Natural Product Reports

HO OH H HO O OH OH H H O HO OH 7a H H HO 8a 8c O 7c H A2 H 7c OH GlcO O H 8c OH RO OGlc OH

223 R=Glc,H-7c/8c=trans 226 H-7a/8a=trans,H-7c/8c=trans 224 R=H,H-7c/8c=trans 227 H-7a/8a=trans,H-7c/8c=cis 225 R=Glc,H-7c/8c=cis

HO H O OH HO OH HO H OH O OH HO H H OH O H H R1O H H OH H H OH O OH H H HO 8c HO OH H HO 7c O OR2 OH OH HO OH OH 228 H-7c/8c=cis 230 R1=Glc 1 6 Glc R2=H 229 H-7c/8c=trans 231 R1=Glc R2=Glc 232

HO HO

OH H HO OH H H H HO OH O O 7a OH HO 8b OH 8a OH H H H 8c 7c OH H H HO H OH O HO O H OH H OH OH OH H HO 233 H-7a=H-8b=H-8c=β,H-8a=H-7c=α 234 H-7a=H-7c=α,H-8a=H-8b=H-8c=β O OH 236 H-7a=H-8b=H-8c=α,H-8a=H-7c=β H 235 HO OH 237

HO HO HO O OH H O OH H H OH HO OH OH O HO 7a H HO O O H H H H H O H OH H H H H H OH H H OH H OH OH O H H HO H H OH OH O H HO HO 7c OH HO OH H O HO 238 239 H-7a=H-7c=β OH 240 H-7a=α,H-7c=β 241 H-7a=H-7c=α 242 H-7a=β,H-7c=α HO 243

15 Electronic supplementary information (ESI) for Natural Product Reports

OR1 HO OH HO H O OH H 7a O O 8a HO O 8d H H HO O H 8c 7d H H HO H H H H 8b 7c 2 H 7b H R O OH H H HO OH H OH OH OH OH

OH OH OH OH 244 R1=R2=H,H-7a=H-7b=H-8b=H-8c=H-8d=β,H-8a=H-7c=H-7d=α 245 R1=R2=H,H-7a=H-7b=H-8b=H-8c=H-7d=α,H-8a=H-7c=H-8d=β 253 246 R1=R2=H,H-7a=H-7b=H-8b=H-8c=H-7d=H-8d=α,H-8a=H-7c=β 247 R1=R2=H,H-7a=H-8b=H-7c=H-8d=H-7b=α,H-8a=H-8c=H-7d=β HO 1 2 248 R =R =H,H-7a=H-8b=H-7c=H-8d=α,H-8a=H-7b=H-8c=H-7d=β H 1 2 O OH 249 R =R =H,H-7a=H-8b=H-7c=H-8d=β,H-8a=H-7b=H-8c=H-7d=α OH 250 R1=H,R2=Glc,H-7a=H-7b=H-8b=H-8c=H-8d=α,H-8a=H-7c=H-7d=β 7a 1 2 8a C 251 R =Glc,R =H,H-7a=H-7b=H-8b=H-8c=H-8d=α,H-8a=H-7c=H-7d=β HO 1 HO 1 2 252 R =R =H,H-7a=H-7b=H-8c=H-8d=α,H-8a=H-7d=β, 8b,7c-didehydro H H H H H H OH OH HO OH

H H C2 O OH HO O O H OH 7a 7d 8a OH HO HO 8d OH H H 8b 8c 254 H-7a=β,H-8a=α 255 H-7a=α,H-8a=β 7b H H 7c HO OH OH H H OH H H O OH HO O

HO OH OH OH H H 256 H-7a=H-7d=β,H-8a=H-7b=H-8b=H-7c=H-8c=H-8d=α 257 H-7a=H-7b=H-8c=H-7d=β,H-8a=H-8b=H-7c=H-8d=α OH HO 258 H-7a=H-7d=H-8c=β,H-8a=H-7b=H-8b=H-7c=H-8d=α OH H H OH 259 H-7a=H-8b=H-7c=H-8d=α,H-7b=H-8a=H-8c=H-7d=β 260 H-7a=H-8c=H-7d=α,H-8a=H-7b=H-8b=H-7c=H-8d=β 261 H-7a=H-8b=H-7c=α,H-8a=H-7b=H-8c=β, 7d,8d-didehydro 262 H-7a=H-7b=H-8c=β,H-8a=H-8b=H-7c=α, 7d,8d-didehydro 265 H-7a=H-8b=H-8c=H-7d=α,H-8a=H-7b=H-7c=H-8d=β OH OH 263

OH HO HO O OH OH H HO O H OH H H H H OH OH HO H H OH H O OH H OH OH OH H H HO 264 H OH HO OH HO

H H O OH O O HO O H HO HO OH 267 O H H

H H OH H H OH

OH OH 266

16 Electronic supplementary information (ESI) for Natural Product Reports

OH

OH

OH

HO HO O H O OH O H HO HO OH O OH OH

H H H H HO H H HO OH HO OH OH

OH OH OH 268 269

HO H O OH HO OH HO HO HO H H O H H OH O OH OH OH H H H H OH H HO H HO H H H H OH OH OH OH O OH H HO OH HO 270 271

HO OH H HO O OH H O OH OH HO HO H HO H OH H H H OH H H H H OH OH O H OH H HO H H OH OH OH OH OH HO OH 272 273 HO H O

HO H H O OH

H HO O OH H H H OH H OH OH

OH OH 274

17 Electronic supplementary information (ESI) for Natural Product Reports

HO H O OH HO OH OH H H O OH HO H HO O H H HO O OH H 7d OH H 8d H H OH 8c O OH H H H H O 7c OH OH OH OH H OH OH HO OH 275 H-7c=H-7d=α,H-8c=H-8d=β 277 276 H-7c=H-7d=β,H-8c=H-8d=α OH H HO O OH HO OH H O O OH H HO OH HO OH O H H H H H 8b 8d OH H OH H 7d OH OH O O H H HO HO OH OH HO 278 H-8b=H-8d=α,H-7d=β 280 279 H-8b=H-8d=β,H-7d=α

HO H O OH 7a 8a HO OH H

HO OH OH H 7c H O OH 7a 8a H HO OH 8d OH HO OH 7d HO O H OH OH OH H 7d 283 H-7a/8a=didehydro,H-7c=H-7d=α,H-8d=β 8d 284 H-7c=H-7d=β,H-8d=α H H O 8c O OH 7c H OH

OH H OH HO O HO H 281 H-7c=H-7d=β,H-8c=H-8d=α,H-7b/8b=trans 282 H-7c=H-8d=β,H-8c=H-7d=α,H-7b/8b=trans 285 H-7a(α) and H-8a(β)=dihydro,H-7c=H-8d=α,H-8c=H-7d=β,H-7b/8b=trans H H OH 286 H-7a(α) and H-8a(β)=dihydro,H-7c=H-8d=α,H-8c=H-7d=β,H-7b/8b=cis HO 284 H-7a(α) and H-8a(β)=dihydro,H-7c=H-8c=H-8d=β,H-7d=α,H-7b/8b=trans

H H H OH HO

O OH H HO 288

18 Electronic supplementary information (ESI) for Natural Product Reports

HO HO

OH

H H OH HO O

OH

HO OH H H H O OH O H OH HO O OH HO H H H H OH O O OH H H OH HO OH 289 290

HO H O OH HO OH HO O H H H H H OH O OH HO HO 292 OH HO H H HO HO O O H O OH HO H H H O OH HO OH H H HO OH O H H H O OH

OH H OH OH OH OH OH 291 293

HO OH HO OH H H O O O O

HO OH HO OH H H

HO OH HO OH OH

HO H H H O HO OH H OH H OH O H OH HO H O H

OH HO HO 294 295

19 Electronic supplementary information (ESI) for Natural Product Reports

HO OGlc HO HO OH OH H O OH OH OH HO H H H HO O OH H H HO H O H HO H OH H O H H H OH H H H HO H HO OH H OH OH O H OH OH HO H H OH OH O 296 297 OH

HO HO OH OH H O OH OH H H H H H H HO OH H HO H H OH H H OH OH OH

OH HO OH OH 298

OH HO HO OH OH OH

H OH H H H OH H H H H OH HO H OH H HO OH OH OH H HO OH HO 299

HO OH OH OH 300 R= H H H OH H H OH HO HO OH OH H H O OH OH OH HO HO H OH HO H H R H O H H OH H 301 R=

OH OH OH

20 Electronic supplementary information (ESI) for Natural Product Reports

OH H HO O HO H OH H OH H H OH OH O H H OH HO H OH H OH HO O OH HO H HO HO H HO HO OH H H HO H H O OH OH O OH HO O OH OH HO H HO OH H H H H H

H H H OH H OH OH H H OH O H

HO OH OH OH OH 302 303

Figure S3 Chemical structures of isorhapontigenin oligomers (304-325) isolated from 1995 to 2008.

O O OH HO OH OH OMe OH OMe R H O

HO MeO OH OH OMe OMe OR OH OH

304 R=H 306 R=H 308 305 R=Glc 307 R=OH

HO OH MeO O OMe HO H R HO H 10 OH OMe MeO H MeO HO HO OH OH OH 309 310 R=OMe 311 R=OMe diastereoisomer of 310 312 R=OCH2Me

21 Electronic supplementary information (ESI) for Natural Product Reports

HO OMe MeO OH OH OH HO

OH HO OH H OMe HO H OH HO HO OH H H H H HO H OH HO H 7a OH H H H HO MeO OH H HO OMe H OH OH OH HO OMe OH OH OMe OMe 313 314 315 H-7a=β OH 316 H-7a=α 317

HO OMe OH OMe OMe HO H HO OMe HO OH H O H O MeO H H 7a OMe HO 8a OH HO H H HO H OH OH OH OH OR OH 318 319 R=H 322 320 R=Glc 321 R=H, 7a,8a=didehydro OH

OH OH HO H H OMe HO OMe OH 7c H H 8c H O OH HO OMe O OMe MeO HO OH OH H HO OH H HO OH H OH OH H OMe OH OH OMe 323 H-7c=α,H-8c=β 325 324 H-7c=β,H-8c=α

Figure S4 Chemical structures of piceatanol oligomers (326-335) isolated from 1995 to 2008

OH HO OH OH OH O H

MeO OH HO O

HO H O OH OMe OH HO OH OH 327 328 326

22 Electronic supplementary information (ESI) for Natural Product Reports

OH HO OH H OH OH O OH OH HO OH H HO O H OH HO OH 8a 7a OH HO O OH H 330 OH HO OH OH OH 329 331 OH OH HO HO OH H H O O 7a 7a 8a 8a GlcO OGlc GlcO OGlc O H H

OH OH OH OH

332 7aR, 8aR 334 7aR, 8aR 333 7aS, 8aS 335 7aS, 8aS

Figure S5 Chemical structures of oxyresveratrol oligomers (336-340) isolated from 1995 to 2008

HO OH OH H OH OH OH OH OH HO HO HO OH H H OH OH OH OH OH HO OH OH OH

OH OH OH

336 337 338

HO OH H O OH HO OH OH H H H O HO HO OH H OH H OH OH

HO OH 339 340

23 Electronic supplementary information (ESI) for Natural Product Reports

Figure S6 Chemical structures of resveratrol and oxyresveratrol oligomers (341-354) isolated from 1995 to 2008

OH HO OH OH R1O OH OR2 H H OH O O 8b H 7b HO HO HO O OH H H O OH OH H HO OH OH 1 2 344 341 342 R =R =H 343 R1=R2=Glc, 7b,8b-didehydro

OH RO OH OH HO

H OH O OH HO OH HO H 7a 8a H OH O HO HO OH H 7a H H 7b 7b H H 8a H OH 8b OH 8b OH H H H H H HO OH OH HO OH OH HO OH HO

OR 345 R=H 347 H-7b=β,H-8b=α 350 H-7a=β,H-8a=β 352 H-8b=α,H-7b=β 346 R=H, 7a,8a-didehydro 348 H-7b=α,H-8b=β 351 H-7a=α,H-8a=α 353 H-8b=β,H-7b=β 349 R=Glc 354 H-8b=β,H-7b=α

Figure S7 Chemical structures of miscellaneous oligomers (355-400) isolated from 1995 to 2008

HO HO R OH H H H O OH O O 7a HO HO 8a OH H H H H H HO 7a O H 7b 8a OH OH OH OH H

OH OH OH OH 355 R=H,H-7b=α,H-7a/8a=trans 356 R=H,H-7b=β,H-7a/8a=trans 358 H-7a/8a=trans 357 R=OH,H-7b=α,H-7a/8a=trans

OH HO H OH HO O OH H H HO OH O H 7a H H HO O R2 8a H H HO O OH OH H HO R1 OH OH

359 R1=H,R2=OH 361 H-7a/8a=trans OH 360 R1=OH,R2=H

24 Electronic supplementary information (ESI) for Natural Product Reports

HO OH HO OH OH H H O HO OH HO H H HO O OH H OH H H H H OH O OH O OH HO O HO O OH HO HO H H H O H

HO HO OH H OH OH OH

OH OH 362 363 OH 364 OH

HO OH OH H OH O OH HO OH H H O HO HO OH H H HO O H H OH OH HO O H OH OH HO OH

365 366 OH 367

OMe OMe HO OH R2 OMe H O R HO R1 OH HO H OH H HO OH O H H HO OH OH OH H OH OH OH

OH OH 368 R=H 1 2 371 R=OH 369 370 R =OH,R =H 372 R1=H,R2=OH

HO OH

OMe OH H H HO HO OH OMe HO OH O O 7a OH O OH 8a H HO HO O HO OH OMe HO OH HO OH HO 373 375 376 374 H-7a(α) and H-8a(β)=dihydro

25 Electronic supplementary information (ESI) for Natural Product Reports

OH OCH OMe 3 OH HO HO OH OH H H O OCH3 HO OCH3 H OMe H H

O HO O H HO 377 OH HO OH 378 379

OCH OCH3 3 HO HO OH H H O O 7a 7a 8a 8a GlcO OGlc GlcO OGlc O H H

OH OH OH OH

380 7aR, 8aR 382 7aR, 8aR 381 7aS, 8aS 383 7aS, 8aS

OH OH OH R2 HO R1 OH H O OMe OR4 OH MeO R3

H 2 OR5 OMe R R1 384 R1=R2=R3=R4=H, R5=Me 385 R1=R2=R3=R5=H, R4=Me 1 2 3 4 5 386 R =OH, R =R =R =H, R =Me OH 387 R1=OH, R2=R3=R5=H, R4=Me 391 R1=H, R2=OH 388 389 R1=R2=OH, R3=H, R4=R5=Me 392 R1=OH, R2=H 390 R1=OH, R2=R5=H, R3=OMe, R4=Me

R2 R2 1 3 1 3 R R R R OH OH OH HO O O OH HO O HO O H H OH OH HO OH O O OH OH O O OH 4 R OH 393 R1=R3=H,R2=OH 394 R1=R3=R4=H,R2=OH 1 3 2 1 3 2 4 398 396 R =R =OH,R =OCH3 395 R =R =OH,R =OMe, R =H 397 R1=R3=OH,R2=H, R4=OMe

HO O O HO O O OH HO OH HO

HO O HO O O OH O OH

O O OH OH OH OH O OH O OH OMe OMe 399 400

26 Electronic supplementary information (ESI) for Natural Product Reports

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