Ginkgolides

Title: Ginkgolides
Literature References: Family of bioactive terpenes isolated from the root bark and leaves of Ginkgo biloba L., Ginkgoaceae. Specific platelet activating factor (PAF) antagonists. Isoln from leaves: S. Furukawa, Sci. Papers Inst. Phys. Chem. Res. Jpn. 19, 27 (1932), C.A. 27, 303 (1933). Isoln from root bark and characterization: M. Maruyama et al., Tetrahedron Lett. 1967, 299; K. Nakanishi, Pure Appl. Chem. 14, 89 (1967); from leaves: N. Sakabe et al., Chem. Commun. 1967, 259; K. Okabe et al., J. Chem. Soc. C 1967, 2201. Crystal structure of B: L. Dupont et al., Acta Crystallogr. C42, 1759 (1986); of A and C: M. Sbit et al., ibid. C43, 2377 (1987). Total synthesis of (±)-B: E. J. Corey et al., J. Am. Chem. Soc. 110, 649 (1988); of (±)-A: E. J. Corey, A. K. Ghosh, Tetrahedron Lett. 29, 3205 (1988). Enantioselective route to B: E. J. Corey, A. V. Gavai, ibid., 3201. Review of syntheses: E. J. Corey, Chem. Soc. Rev. 17, 111-133 (1988). 1H- and 13C-NMR: C. Roumestand et al., Tetrahedron 45, 1975 (1989). Effect on PAF receptor binding: R. Korth et al., Eur. J. Pharmacol. 152, 101 (1988). Review: P. Braquet et al., Med. Res. Rev. 11, 295-355 (1991). Review of physical properties: T. A. van Beek, Bioorg. Med. Chem. 13, 5001-5012 (2005).
Properties: Ginkgolides are sol in acetone, ethanol, methanol, ethyl acetate, THF, dioxane, acetic acid, trifluoroacetic acid, acetonitrile, pyridine, DMSO; sparingly sol in ether, water. Insol in hexane, benzene, chloroform, carbon tetrachloride.
Derivative Type: Ginkgolide A
CAS Registry Number: 15291-75-5
Manufacturers' Codes: BN-52020
Molecular Formula: C20H24O9
Molecular Weight: 408.40
Percent Composition: C 58.82%, H 5.92%, O 35.26%
Properties: Bitter crystals from ethanol, mp ~300° (dec). [a]D24 -53.4° (c = 1 in ethanol). uv max (ethanol): 219 nm (log e 2.72).
Melting point: mp ~300° (dec)
Optical Rotation: [a]D24 -53.4° (c = 1 in ethanol)
Absorption maximum: uv max (ethanol): 219 nm (log e 2.72)
Derivative Type: Ginkgolide B
CAS Registry Number: 15291-77-7
CAS Name: (1b)-1-Hydroxyginkgolide A
Manufacturers' Codes: BN-52021
Molecular Formula: C20H24O10
Molecular Weight: 424.40
Percent Composition: C 56.60%, H 5.70%, O 37.70%
Literature References: Review of pharmacology and PAF-antagonism: P. Braquet, R. H. Bourgain, Adv. Exp. Med. Biol. 215, 215-235 (1987). Clinical trial in asthma: K.-H. Hsieh, Chest 99, 877 (1991); in severe sepsis: J. F. Dhainaut et al., Crit. Care Med. 22, 1720 (1994).
Properties: Bitter crystals from ethanol, mp ~300° (dec). [a]D24 -52.6° (c = 1 in ethanol). uv max (ethanol): 219 nm (log e 2.37). Log P (water/n-octanol): 1.72. pKa1 7.14; pKa2 8.60; pKa3 11.89.
Melting point: mp ~300° (dec)
pKa: pKa1 7.14; pKa2 8.60; pKa3 11.89
Optical Rotation: [a]D24 -52.6° (c = 1 in ethanol)
Log P: Log P (water/n-octanol): 1.72
Absorption maximum: uv max (ethanol): 219 nm (log e 2.37)
Derivative Type: Ginkgolide C
CAS Registry Number: 15291-76-6
CAS Name: (1a,7b)-1,7-Dihydroxyginkgolide A
Manufacturers' Codes: BN-52022
Molecular Formula: C20H24O11
Molecular Weight: 440.40
Percent Composition: C 54.54%, H 5.49%, O 39.96%
Properties: Bitter crystals from ethanol, mp ~300° (dec). [a]D24 -14.7° (c = 1 in ethanol). uv max (ethanol): 220 nm (log e 2.30).
Melting point: mp ~300° (dec)
Optical Rotation: [a]D24 -14.7° (c = 1 in ethanol)
Absorption maximum: uv max (ethanol): 220 nm (log e 2.30)
Use: Reference compd for PAF receptors in biological systems.
Giractide Girard Reagents Gitalin Gitogenin Gitoxigenin

Chemical structure of ginkgolides

Ginkgolides are biologically active terpenic lactones present in Ginkgo biloba. They are diterpenoids with 20-carbon skeletons, which are biosynthesized from geranylgeranyl pyrophosphate.[1]

Miraculous Ginkgolide B
ginkgolid
R1 R2 R3
A OH H H
B OH OH H
C OH OH OH
J OH H OH
M H OH OH

Gingkolide B may be effective as preventive treatment in reducing migraine attack frequency.[2]