Amurensin K

Amurensin K
Names

Preferred IUPAC name (1S,6R,7S,11bS)-6-{5-[(7S,8S)-8-(3,5-Dihydroxyphenyl)-4-hydroxy-7-(4-hydroxyphenyl)-7,8-dihydrobenzo[1,2-b:4,3-b′]difuran-2-yl]-2-hydroxyphenyl}-1,7-bis(4-hydroxyphenyl)-1,6,7,11b-tetrahydrobenzo[6,7]cyclohepta[1,2,3-cd][1]benzofuran-4,8,10-triol
Identifiers
CAS Number	388121-56-0
3D model (JSmol)	Interactive image
ChemSpider	17288573
PubChem CID	16131909
UNII	37E366SR4Q^Y
CompTox Dashboard (EPA)	DTXSID801045300
InChI InChI=1S/C56H40O13/c57-30-8-1-25(2-9-30)47-49(38-20-36(63)22-45-51(38)53(39-19-35(62)21-42(65)50(39)47)55(68-45)27-5-12-32(59)13-6-27)37-17-28(7-14-41(37)64)44-23-40-52-46(24-43(66)56(40)67-44)69-54(26-3-10-31(58)11-4-26)48(52)29-15-33(60)18-34(61)16-29/h1-24,47-49,53-55,57-66H/t47-,48+,49+,53+,54-,55-/m1/s1 Key: KYCWATKXJOSHQR-KPXHRNBCSA-N
SMILES C1=CC(=CC=C1[C@@H]2[C@H](C3=CC(=CC4=C3[C@@H]([C@H](O4)C5=CC=C(C=C5)O)C6=CC(=CC(=C26)O)O)O)C7=C(C=CC(=C7)C8=CC9=C1[C@@H]([C@H](OC1=CC(=C9O8)O)C1=CC=C(C=C1)O)C1=CC(=CC(=C1)O)O)O)O
Properties
Chemical formula	C₅₆H₄₀O₁₃
Molar mass	920.91 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Amurensin K is an oligostilbene. It is a resveratrol tetramer found in Vitis amurensis.^[1] Preliminary tests have shown it to be an effective neuraminidase inhibitor against the influenza A virus subtype H1N1.^[2]

References

^ Huang, Kai-Sheng; Lin, Mao; Cheng, Gui-Fang (September 2001). "Anti-inflammatory tetramers of resveratrol from the roots of Vitis amurensis and the conformations of the seven-membered ring in some oligostilbenes". Phytochemistry. 58 (2): 357–362. Bibcode:2001PChem..58..357H. doi:10.1016/S0031-9422(01)00224-2. PMID 11551564.
^ Nguyen, Thi Ngoc Anh; Dao, Trong Tuan; Tung, Bui Thanh; Choi, Hwanwon; Kim, Eunhee; Park, Junsoo; Lim, Seong-IL; Oh, Won Keun (2011). "Influenza A (H1N1) neuraminidase inhibitors from Vitis amurensis". Food Chemistry. 124 (2): 437–443. doi:10.1016/j.foodchem.2010.06.049. ISSN 0308-8146.

Oligostilbenoids and their glycosides

Dimers

Trimers

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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