Oligostilbenoid

Chemical structure of hopeaphenol.

Oligostilbenoids (oligo- or polystilbenes) are oligomeric forms of stilbenoids. Some molecules are large enough to be considered polyphenols and constitute a class of tannins.^[1]

Examples

α-Viniferin
Ampelopsin A^[2]
Ampelopsin E^[2]
Diptoindonesin C can be isolated from the bark of Shorea pinanga^[3]
Diptoindonesin F can be isolated from the bark of Shorea gibbosa^[2]
Epsilon-viniferin
Flexuosol A^[4]
Gnetin H^[3]
Hemsleyanol D^[2]
Hopeaphenol^[3]
trans-Diptoindonesin B
Vaticanol B^[2]

Glycosides

Diptoindonesin A

References

↑ Boralle, N; Gottlieb, H.E; Gottlieb, O.R; Kubitzki, K; Lopes, L.M.X; Yoshida, M; Young, M.C.M; Oligostilbenoids (1993). "Gnetum venosum". Phytochemistry 34 (5): 1403–1407. doi:10.1016/0031-9422(91)80038-3. INIST:4012160.
1 2 3 4 5 Saroyobudiono, Haryoto; Juliawaty, Lia D.; Syah, Yana M.; Achmad, Sjamsul A.; Hakim, Euis H.; Latip, Jalifah; Said, Ikram M. "Oligostilbenoids from Shorea gibbosa and their cytotoxic properties against P-388 cells". Journal of Natural Medicines 62 (2): 195–198. doi:10.1007/s11418-007-0205-0.
1 2 3 Yana M. Syah; Euis H. Hakim; Emilio L. Ghisalberti; Afghani Jayuska; Didin Mujahidin; Sjamsul A. Achmad (2009). "A modified oligostilbenoid, diptoindonesin C, from Shorea pinanga Scheff". Natural Product Research 23 (7): 591–594. doi:10.1080/14786410600761235.
↑ Li, Wen-wu; Li, Bo-Gang; Chen, Yao-zu (1998). "Flexuosol A, a New Tetrastilbene fromVitis flexuosa". Journal of Natural Products 61 (5): 646–7. doi:10.1021/np970457v. PMID 9599267.

Hydroxystilbenes and their glycosides (monomeric forms)

Dihydroxylated

Trihydroxylated

Resveratrol

Tetrahydroxylated

O-methylated

4-Methoxyresveratrol Gnetucleistol D (2-methoxyoxyresveratrol) Gnetucleistol E (3-methoxy-isorhapontigenin) Isorhapontigenin (3,4',5-trihydroxy-3'-methoxystilbene) Pinostilbene (3-methoxyresveratrol) Pterostilbene (3',5'-dimethoxyresveratrol) Rhapontigenin (piceatannol 4'-methyl ether)

Combretastatins	Combretastatin A-1 Combretastatin A-4

carboxylated

Hydrangeic acid

other acylations

3,5-Dihydroxy-4-isopropyl-trans-stilbene

Glycosides

Astringin (Piceatannol 3-O-glucoside)
Isorhapontin (Isorhapontigenin glucoside)
Mulberroside A (Oxyresveratrol diglucoside)

of resveratrol	Piceid (trans-Resveratrol-3-O-glucoside) trans-Resveratrol-3-O-glucuronide Resveratroloside (trans-resveratrol-4'-O-beta-D-glucopyranoside)

of rhapontigenin	Rhapontigenin 3-O-rutinoside 4'-Methoxy-(E)-resveratrol 3-O-rutinoside Rhaponticin (Rhapontigenin glucoside)

Oligomeric forms

oligostilbenoids

Oligostilbenoids and their glycosides

Diptoindonesin C
Diptoindonesin F
Gnetin H
Hemsleyanol D
Isohopeaphenol
Laetevirenol A, B, C, D and E
Suffruticosol A and B
Viniferal
E-ω-viniferin
Z-ω-viniferin

Dimers

Diptoindonesin G
Jezonodione
B
Scirpusin A
Tibeticanol (piceatannol dimer)

Trimers

Amurensin B
Gnetin E
Gneyulin A
Johorenol A
Ampelopsin E
Vaticanol G

Tetramers:

Dibalanocarpol
Gnetin J (3"-hydroxygnetin E)
Gnetin K (3"-methoxygnetin E)
Gnetuhainin R (isorhapontigenin tetramer)
Laetevirenol F and G

Higher polymers
(five units or more)

Vaticanol D, H, I and J

Oligomeric forms
of resveratrol

Dimers	Amurensin A and H Ampelopsin A B D and F Balanocarpol Cyphostemmin A and B δ-viniferin ε-viniferin Gnetin A and C Leachinol F Malibatol A Pallidol Parthenocissin A Quadrangularin A Restrytisol A, B and C Vitisinol D

Trimers	α-viniferin Ampelopsin C Amurensin C, D and G Hopeanolin Malaysianol A Miyabenol C Resviniferin A and B trans-diptoindonesin B

Tetramers	Ampelopsin H Amurensin K Caraphenol B Carasinol B Flexuosol A Hopeaphenol Kobophenol A Miyabenol A Vaticanol B and C Vaticaphenol A Vitisin A B and C β-viniferin (cyclic resveratrol tetramer)

Pentamers	Amurensin E and F

Hexamers	Chunganenol

Higher polymers	γ-viniferin Valeriaphenol A

Glycosides or conjugates

Diptoindonesin A (C-glucoside of ε-viniferin)
Foeniculoside I (glucoside of miyabenol C), II, III and IV
Laevifonol (an ε-viniferin-ascorbic acid hybrid compound)
Laevifoside (O-glucoside of ampelopsin A)

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