Silvestrol aglycone

• CAT Number: I005693
• CAS Number: 960365-65-5
• Molecular Formula: C27H26O8
• Molecular Weight: 478.49
• Purity: ≥95%
• Solubility: 10 mM in DMSO
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: methyl (1R,2R,3S,3aR,8bS)-1,6,8b-trihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylate
• InChI: InChI=1S/C27H26O8/c1-32-18-11-9-16(10-12-18)27-22(15-7-5-4-6-8-15)21(25(30)34-3)24(29)26(27,31)23-19(33-2)13-17(28)14-20(23)35-27/h4-14,21-22,24,28-29,31H,1-3H3/t21-,22-,24-,26+,27+/m1/s1
• InChIKey: HYLOONIBWUNKDH-PXIJUOARSA-N
• SMILES: COC1=CC=C(C=C1)C23C(C(C(C2(C4=C(O3)C=C(C=C4OC)O)O)O)C(=O)OC)C5=CC=CC=C5

Silvestrol aglycone (CAT: I005693) is a derivative of rocailles, a class of compounds found in the plant Aglaia foveolate, known for their potential anticancer properties. Silvestrol aglycone has been shown to induce apoptosis (programmed cell death) in LNCaP cells, a prostate cancer cell line. It exerts its effects through the mitochondrial/apoptosome pathway, which involves the release of mitochondrial proteins and the activation of caspases. Interestingly, silvestrol aglycone induces apoptosis without activating executioner caspases-3 or -7, which are typically involved in the final steps of apoptosis. This compound also shows inhibitory activity against the 5′ untranslated region of the myc gene, which plays a role in cancer development and progression.

Reference

1. Kim S, et al. Silvestrol, a potential anticancer rocaglate derivative from Aglaia foveolata, induces apoptosis in LNCaP cells through the mitochondrial/apoptosome pathway without activation of executioner caspase-3 or -7. Anticancer Res. 2007 Jul-Aug;27(4B):2175-83. 

2. Liu T, et al. Synthetic silvestrol analogues as potent and selective protein synthesis inhibitors. J Med Chem. 2012 Oct 25;55(20):8859-78.