1220. Bilobalide

Nomenclature

CAS number: 33570-04-6
(3aS,5aR,8R,8aS,9R,10aS)-9-(1,1-Dimethylethyl)-10,10a-dihydro-8,9-dihydroxy-4H,5aH,9H-furo[2,3-b]furo[3′,2′:2,3]cyclopenta[1,2-c]furan-2,4,7(3H,8H)trione.
C15H18O8; mol wt 326.30.
C 55.21%, H 5.56%, O 39.23%.

Description and references

Sesquiterpene isolated from the leaves of Ginko biloba L., Ginkgoaceae; closely related to the ginkgolides, q.v. Component of the Ginkgo biloba extract, EGb 761, q.v. Isoln: K. Weinges, W. B"ahr, Ann. 724, 214 (1969). NMR and MS analysis: eidem, ibid. 759, 158 (1972). Structure determn: K. Nakanishi et al., J. Am. Chem. Soc. 93, 3544 (1971). Total synthesis of (±)-form: E. J. Corey, W. Su, ibid. 109, 7534 (1987). Enantioselective synthesis of (-)-form: eidem, Tetrahedron Lett. 29, 3423 (1988). Separation from Ginkgo biloba extracts: S. Jaracz et al., Phytochemistry 65, 2897 (2004). Neuroprotective effects in animal models of brain ischemia: K. Chandrasekaran et al., Brain Res. 922, 282 (2001). GABAA antagonist activity: S. H. Huang et al., Eur. J. Pharmacol. 464, 1 (2003). Review of neuroprotective properties: F. V. Defeudis, Pharmacol. Res. 46, 565-568 (2002); of physical properties: T. A. van Beek, Bioorg. Med. Chem. 13, 5001-5012 (2005).

Chemical structure

Properties

Colorless crystals from water, mp >300°. [α]57820 -64.3° (c = 2 in acetone).