Electronic Supplementary Material (ESI) for Natural Product Reports This journal is © The Royal Society of Chemistry 2012 Electronic supplementary information (ESI) for Natural Product Reports SUPPORTING INFORMATION Natural Stilbenoids: distribution in the plant kingdom and chemotaxonomic interest in Vitaceae Céline Rivière,*ab Alison D. Pawlusa and Jean-Michel Mérillona aUniversité de Bordeaux, Groupe d’Etude des Substances Végétales à Activité Biologique (GESVAB), EA 3675, Institut des Sciences de la Vigne et du Vin, 210 Chemin de Leysotte, CS 50008, F-33882 Villenave d’Ornon Cedex, France. bLaboratoire de Pharmacognosie, EA4481 (GRIIOT), Faculté des Sciences Pharmaceutiques et Biologiques, Université Lille Nord de France (Lille 2), F-59006 Lille Cedex, France E-mail: [email protected] Tel/Fax: +33 (0)3-20964041 The ‘Supporting Information’ is a supplementary data for section 2 to illustrate the distribution of all stilbenes, stilbene hydrids and 2-arlybenzofurans in the plant kingdom up to March 2012 and for section 3 to illustrate the distribution and the chemical structures of all stilbenoids in Vitaceae. The ‘Supporting Information’ was composed of twelve parts: Table S1 Distribution of stilbenes, stilbene hybrids and 2-arylbenzofuran derivatives in Embryophyta division References Table S2 Monomers isolated from Vitaceae genera Table S3 Benzofuran-type stilbenes isolated from Vitaceae genera Table S4 Monomers O-glycosides isolated from Vitaceae Table S5 Phenanthrene derivative O-glycoside isolated from Vitaeae genera Table S6 Monomers C-glycosides isolated from Vitaceae genera Table S7 Dimers isolated from Vitaceae genera Table S8 Trimers isolated from Vitaceae genera Table S9 Tetramers isolated from Vitaceae genera Table S10 Breakdown product from tetramer isolated from Vitaceae genera Table S11 Pentamers isolated from Vitaceae genera Table S12 Hexamer isolated from Vitaceae genera References Electronic Supplementary Material (ESI) for Natural Product Reports This journal is © The Royal Society of Chemistry 2012 Electronic supplementary information (ESI) for Natural Product Reports Table S1 Distribution of stilbenes, stilbene hybrids and 2-arylbenzofuran derivatives from the Embryophyta division Order Family Genus Species Type of compound1 Ref Bryophytes - Marchantiophyta (Liverworts) Marchantiales Corsiniaceae Corsinia C. coriandrina Whole plant: (E)-3,4'-dimethoxystilbene 1, 2 (Spreng.) Lindb. (M), (Z)-3,4'-dimethoxystilbene (M), corsifuran C (MB) Lejeuneaceae Marchesinia M. bongardiana Gametophytes: 3,4-dihydroxy-3'- 1, 3 Trevis. methoxystilbene (M) Euphyllophytes - Monilophytes - Psilotopsida Ophioglossales Ophioglossaceae Helminthostachys H. zeylanica (L.) Rhizomes: ugonstilbenes A-C (McG) 1, 4 Hook. Euphyllophytes- Monilophytes – Polypodopsidia Polypodiales Dryopteridaceae Dryopteris D. sublaeta Ching Fresh plant: 3,5-dihydroxy-stilbene-3-O- 5 & Y.P. Hsu neohesperidoside (MOG), 3,5-dihydroxy- stilbene-3-O-β-D-glucoside (MOG) Spermatophytes – Gymnosperms - Gnetophytes Gnetales Welwitschiaceae Welwitschia W. mirabilis Hook. Wood: gnetins F-G (DR), gnetins H-I 6 f. (TrR) Stems and roots: gnetin C (DR), gnetin F 1, 7-8 (DR), mirabilosides A-B (DROG), gnetins E and I (TrR), mirabilols A-B (TrR) Stems and roots: resveratrol (M), gnetin 9 G (DR), gnemonoside B (DROG), mirabilosides C-F (TrROG) Gnetaceae Gnetum G. africanum Stems: resveratrol (M), isorhapontigenin 1, 8, 10-12 Welw. (M), gnetol (M), gnetifolin K (MOG), resveratrol 3,4'-O-β-diglucopyranoside (MOG), piceatannol 4'-O-β- glucopyranoside (MOG), piceatannol 3,4'- O-β-diglucopyranoside (MOG), resveratroloside (MOG), longusol A (DRP), gnetin C (DR), gnetin D (DRO), gnetofolin E (D), gneafricanin A (DIO), gneafricanin B (DIP), gneafricanin C (DP), gneafricanin D (DR), gneafricanin E (DRO), gneafricanin F (DI), bisisorhaphontigenin B (DI), gnemonosides A-B and H (DROG) gnemonosides I-J (DROOG), gnetin E (TrR) Stems: gnetoflavanols A-D (FS) 13 G. cleistostachyum Lianas: resveratrol (M), piceatannol (M), 14-17 C.Y.Cheng rhapontigenin (M), isorhapontigenin (M), 4-methoxyresveratrol (M), pinosylvin (M) gnetucleistol B = (Z)-3,5,10,14- tetrahydroxy-4-methoxylstilbene (M), gnetupendin B (M), gnetucleistol D = 2- methoxyoxyresveratrol (M), gnetucleistol E = 3-methoxyisorhapontigenin (M), gnetol (M), gnetifolin A (MB), gnetucleistol C (MB), shegansu B (DI), bisisorhapontigenin A (DI), Z shegansu B (DI), gnetuhainin P (DI), gnetulin (DI), gnetucleistol F (SL), lehmbachol D (SL), gnetifolin F (SL), gnetofuran A (SHP), gnetumontanin C (SHL), gnetucleistol A (SHI) G. gnemon L. Roots: gnetol (M), gnetifolin K (MOG), 1, 8, 18-21 gnetin C (DR), gnetin D (DRO), gnemonol G (DR), gnemonol M (DI), gnemonosides A-B (DROG), gnemonol A (TrRO), gnemonols D-F (TrRO), gnemonols I-J (TrRO), gnemonol H (TrR), gnemonols K-L (TrR), ampelopsin- E (TrR), Z-ampelopsin-E (TrR), gnetin E (TrR), gnemonosides F and K (TrROG), gnemonol B (TeR) Roots: gnetoflavanols E-F (FS) 13 Seeds: resveratrol (M), gnetin C (DR), 22 gnetin L (DIR), gnemonosides A, C, D (DROG) Electronic Supplementary Material (ESI) for Natural Product Reports This journal is © The Royal Society of Chemistry 2012 Electronic supplementary information (ESI) for Natural Product Reports G. gnemon L. Fruits: resveratrol (M), isorhapontigenin 23 (M), gnetin C (DR), gnemonosides D and L (DROG), gnetin E (TrR), gnemonoside M (TrOG) G. gnemonoides Stems: resveratrol (M), resveratroloside 1, 8, 12, 18, Brongn. (MOG), gnetin C (DR), gnetin D (DRO), 24 2b-hydroxyampelopsin F (DRO), gnetofolin E (D), gnemonosides A-E and H (DROG), gnemonosides F-G (TrROG), gnetin E (TrR), gnemonol C (TeRO), gnetal (OgD) Barks: gneyulins A-B (TrO) 25 G. hainanense Lianas: resveratrol (M), oxyresveratrol 1, 26-32 C.Y. Cheng ex (M), rhapontigenin (M), isorhapontigenin L.K. Fu, Y. F. Yu (M), gnetol (M), gnetulin (DI), (-)-ε- & M.G. Gilbert viniferin (DR), resveratrol transdehydrodimer (DR), gnetuhainins A- E (DRO), gnetuhainins F-J and P (DI), gnetuhainin K (DIG), gnetuhainin L (DIO), gnetuhainin Q (DIR), gnetuhainin S (DR), gnetuhainin M (TrR), gnetuhainin O-P (TrI), gnetuhainin R (TeI) G. klossii Merr. ex Stems: E-resveratrol (M), 1, 33 Markgraf isorhapontigenin (M), gnetol (M), gnetofurans B-C (MB), gnetulin (DI), gnetin C (DR), (-)-ε-viniferin (DR), latifolol (TrRO), gnetin E (TrR), gnetifolin F (SL), gnetofuran A (SHP) G. latifolium Stems: resveratrol (M), gnetin C (DR), 1, 34 Blume gnetin D (DRO), (-)-ε-viniferin (DR), gnetin E (TrR), latifolol (TrRO) G. leyboldii Tul. Wood bark: gnetin A (DR), gnetin B 35 (DR), gnetin C (DR), gnetin D (DRO), gnetin E (TrR) G. macrostachyum Roots: E-resveratrol (M), gnetol (M), 36-37 Hook. f. isorhapontigenin (M), bisisorhapontigenin B (DI), parvifolol A (DRO), macrostachyol C (DRO), macrostachyol D (DIR), latifolol (TrRO), macrostachyol B (TrR), macrostachyol A (TeRO) G. montanum Lianas: resveratrol (M), gnetol (M), 1, 38-40 Markgr. isorhapontigenin (M), gnetifolin E (MOG), isorhapontigenin 3-O-β-D- glucoside (MOG), stemofuran B = gnetifolin M = gnetifolin P (MB), gnetifolins L-O (DI), (-)-ε-viniferin (DR), gnetifolin C (D) G.montanum fo. Lianas: oxyresveratrol (M), 1, 41-42 megalocarpum rhapontigenin (M), resveratrol (M), Markgr. isorhapontigenin (M), gnetol (M), pinosylvin (M), gnetupendin B (M), gnetumelin A = 10-benzyl-3-O- demethylisorhapontigenin (M), gnetumelin C = 5-[3-(4-hydroxy-3- methoxy-phenyloxiran-2-yl]benzene- 1,2,3-triol (M), isorhapontigenin 3-O-β-D- glucoside (MOG), isorhapontigenin 12-β- D-glucoside (MOG), gnetifolin E (MOG), gnetifolin K (MOG), gnetifolin A (MB), gnetofuran B (MB), gnetifolin M = gnetifolin P (MB), gnetumelin B (MB), (-)-ε-viniferin (DR), gnetumontanin A (DO), shegansu B (DI), gnetulin (DI), gnetin D (DRO), gnetumontanin C (SHL), gnetumontanin D (SHLOG), gnetumontanin B (TrOR), gnetuhainin M (TrR) G. parvifolium Lianas: resveratrol (M), isorhapontigenin 1, 8, 43-49 (Warb.) W.C. (M), gnetol (M), pinosylvin (M), Cheng gnetifolin (MOG), gnetifolin K (MOG), isorhapontigenin 3-O-β-D- glucopyranoside (MOG), isorhapontigenin-4'-O-β-glucopyranoside (MOG), Electronic Supplementary Material (ESI) for Natural Product Reports This journal is © The Royal Society of Chemistry 2012 Electronic supplementary information (ESI) for Natural Product Reports G. parvifolium isorhapontigenin-12-O-β-D-glucoside = (Warb.) W.C. gnetifolin E (MOG), gnetifolin A (MB), Cheng gnetifolins C-D (D), (-)-ε-viniferin (DR), gnetulin (DI), parvifolols A-B (DRO), parvifolol C (DO), shegansu B = parvifolol D (DI), 2b-hydroxyampelopsin F (DRO), gnetifolin F (SL) Stems: resveratrol (M), isorhapontigenin 50 (M), gnetol (M), isorhapotigenin 3-O-β-D- glucopyranoside (MOG), gnetuhainin E (DRO), shegansu B (DI), lehmbachol D (SL) G. pendulum C.Y. Lianas: resveratrol (M), isorhapontigenin 1, 51-54 Cheng (M), gnetupendins A-B (M), isorhapontigenin-3-O-β-D-glucoside (MOG), shegansu B (DI), gnetupendin C (DRO), gnetulin (DI), gnetin D (DRO), gnetupendin D (DIOG) G. ula Brongn. Whole plant: gnetol (M), 3,4- 55-57 methylenedioxy-4′-methoxy-E-stilbene = gnetin (M), 3,4,5′-trihydroxy-3′-methoxy- E-stilbene (M), gnetulin (DI) G. venosum Seeds: resveratrol (M), isorhapontigenin 58 Spruce ex Benth. (M), gnetin C (DR), gnetin E (TrR), gnetin J (TrR*), gnetin K (TrR*) G. schwackeanum Fruits: gnetin C (DR), gnetin E (TrR) 35 Taub. ex Markgr. Spermatophytes – Gymnosperms – Pinales order – Pinaceae family Pinales Pinaceae Abies A. chensiensis Aerial Parts: resveratrol (M), Z- 59 Tiegh. resveratrol (M), piceid (MOG) Larix L. laricina