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

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]

Glycosides

  • Diptoindonesin A

References

  1. ^ 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.
  2. ^ a b c d e 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.
  3. ^ a b c d 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.
  4. ^ a b c 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.
  5. ^ 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

  • Media related to Oligostilbenoids at Wikimedia Commons
  • v
  • t
  • e
Hydroxystilbenes and their glycosides (monomeric forms)
Dihydroxylated
  • Pinosylvin
  • 3,4′-Dihydroxystilbene
TrihydroxylatedTetrahydroxylatedO-methylated
Combretastatins
carboxylatedother acylationsGlycosides
of resveratrol
of rhapontigenin
  • Rhapontigenin 3-O-rutinoside
    • 4'-Methoxy-(E)-resveratrol 3-O-rutinoside
  • Rhaponticin (Rhapontigenin glucoside)
Oligomeric forms
oligostilbenoids
  • v
  • t
  • e
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
Trimers
Tetramers
Pentamers
Hexamers
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)