Silvestrol

Silvestrol is a natural product from the flavagline family, with a cyclopenta[b] benzofuran core structure and an unusual dioxane ether side chain, which is found in the bark of trees from the genus Aglaia, especially Aglaia silvestris and Aglaia foveolata.^[1]

Silvestrol

Identifiers
IUPAC name Methyl (1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1R)-1,2-dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b] [1]benzofuran-2-carboxylate
CAS Number	697235-38-4 Y
PubChem CID	11787114
ChemSpider	9961792
UNII	KK3Y3KN5BV
ChEBI	CHEBI:66484
ChEMBL	ChEMBL555196
Chemical and physical data
Formula	C34H38O13
Molar mass	654.665 g·mol−1
3D model (JSmol)	Interactive image
SMILES CO[C@H]1[C@@H](O[C@H](CO1)[C@@H](CO)O)OC2=CC3=C(C(=C2)OC)[C@@]4([C@@H]([C@@H]([C@H]([C@@]4(O3)C5=CC=C(C=C5)OC)C6=CC=CC=C6)C(=O)OC)O)O
InChI InChI=1S/C34H38O13/c1-40-20-12-10-19(11-13-20)34-27(18-8-6-5-7-9-18)26(30(38)42-3)29(37)33(34,39)28-23(41-2)14-21(15-24(28)47-34)45-32-31(43-4)44-17-25(46-32)22(36)16-35/h5-15,22,25-27,29,31-32,35-37,39H,16-17H2,1-4H3/t22-,25-,26-,27-,29-,31-,32-,33+,34+/m1/s1 Key:GVKXFVCXBFGBCD-QKDMMWSPSA-N

Bioactivity

It acts as a potent and selective inhibitor of the RNA helicase enzyme eIF4A, and has both broad-spectrum antiviral activity against diseases such as Ebola and coronaviruses, ^{[2][3][4][5][6]} and anti-cancer properties,^[7][8] which makes it of considerable interest in medical research. However, as it cannot be extracted from tree bark in commercial amounts and is prohibitively complex to produce synthetically,^[9] practical applications have focused more on structurally simplified analogues such as CR-31-B.^[10]

See also

• Rocaglamide