Title: Bilobalide
CAS Registry Number: 33570-04-6
CAS Name: (3a
S,5a
R,8
R,8a
S,9
R,10a
S)-9-(1,1-Dimethylethyl)-10,10a-dihydro-8,9-dihydroxy-4
H,5a
H,9
H-furo[2,3-
b]furo[3¢,2¢:2,3]cyclopenta[1,2-
c]furan-2,4,7(3
H,8
H)trione
Molecular Formula: C15H18O8
Molecular Weight: 326.30
Percent Composition: C 55.21%, H 5.56%, O 39.23%
Literature 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?hr,
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).
Properties: Colorless crystals from water, mp >300°. [a]57820 -64.3° (c = 2 in acetone).
Melting point: mp >300°
Optical Rotation: [a]57820 -64.3° (c = 2 in acetone)