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
Dimers
- Ampelopsin A[2]
- Epsilon-viniferin
- Pallidol[3]
- Quadrangularin A[3]
Trimers
- α-Viniferin
- Ampelopsin E[2]
- trans-Diptoindonesin B
- Gnetin H[4]
Tetramers
- cajyphenol A[3]
- cajyphenol B[3]
- Flexuosol A[5]
- Hemsleyanol D[2]
- Hopeaphenol[4]
- Vaticanol B[2]
- R2-Viniferin (syn. Vitisin A)
Modified
- Diptoindonesin C can be isolated from the bark of Shorea pinanga[4]
Other
- Diptoindonesin F can be isolated from the bark of Shorea gibbosa[2]
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. (2008). "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 4 Bao, Li; Ma, Xiaofeng; Song, Xiaohong; Wang, Manyuan; Liu, Hongwei (2010). "Two New Resveratrol Tetramers Isolated from Cayratia japonica (Thunb.) Gagn. With Strong Inhibitory Activity on Fatty Acid Synthase and Antioxidant Activity". Chemistry & Biodiversity. 7 (12): 2931–2940. doi:10.1002/cbdv.200900394. PMID 21162006.
- 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. PMID 19401910.
- ↑ 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.
External links
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Dihydroxylated |
- Pinosylvin
- 3,4′-Dihydroxystilbene
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Trihydroxylated | |
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Tetrahydroxylated |
- Oxyresveratrol
- Piceatannol
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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
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carboxylated | |
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other acylations |
- 3,5-Dihydroxy-4-isopropyl-trans-stilbene
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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)
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of rhapontigenin |
- Rhapontigenin 3-O-rutinoside
- 4'-Methoxy-(E)-resveratrol 3-O-rutinoside
- Rhaponticin (Rhapontigenin glucoside)
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Oligomeric forms | |
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- 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
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Dimers |
- Diptoindonesin G
- Jezonodione
- B
- Scirpusin A
- Tibeticanol (piceatannol dimer)
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Trimers |
- Amurensin B
- Gnetin E
- Gneyulin A
- Johorenol A
- Ampelopsin E
- Vaticanol G
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Tetramers: |
- Dibalanocarpol
- Gnetin J (3"-hydroxygnetin E)
- Gnetin K (3"-methoxygnetin E)
- Gnetuhainin R (isorhapontigenin tetramer)
- Laetevirenol F and G
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Higher polymers (five units or more) | |
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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
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Trimers |
- α-viniferin
- Ampelopsin C
- Amurensin C, D and G
- Hopeanolin
- Malaysianol A
- Miyabenol C
- Resviniferin A and B
- trans-diptoindonesin B
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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)
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Pentamers | |
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Hexamers | |
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Higher polymers |
- γ-viniferin
- Valeriaphenol A
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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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