Ginkgolide B

Names

[ Name ]:
Ginkgolide B

[Synonym ]:
(1R,3R,6R,7S,8S,10R,11R,12R,13S,16S,17R)-6,12,17-Trihydroxy-16-methyl-8-(2-methyl-2-propanyl)-2,4,14,19-tetraoxahexacyclo[8.7.2.0.0.0.0]nonadecane-5,15,18-trione
ginkgolide b from ginkgo biloba leaves
6H-9,4a-(Epoxymethano)-3aH,9H-cyclopenta[c]furo[2,3-b]furo[3',2':3,4]cyclopenta[1,2-d]furan-2,6,13(1H)-trione, 11-(1,1-dimethylethyl)hexahydro-1,4b,8-trihydroxy-5-methyl-, (1R,3aR,4aR,4bR,5S,8R,8aS,9R,11S,11aS)-
7-DEOXYGINKGOLIDE C
6H-9,4a-(Epoxymethano)-3aH,9H-cyclopenta[c]furo[2,3-b]furo[3',2':3,4]cyclopenta[1,2-d]furan-2,6,13(1H)-trione, 11-(1,1-dimethylethyl)hexahydro-1,4b,8-trihydroxy-5-methyl-, (1R,3aR,4aR,4bR,5S,7aS,8R,8aR,9R,11S,11aS)-
6H-9,4a-(epoxymethano)-3aH,9H-cyclopenta[c]furo[2,3-b]furo[3',2':3,4]cyclopenta[1,2-d]furan-2,6,13(1H)-trione, 11-(1,1-dimethylethyl)hexahydro-1,4b,8-trihydroxy-5-methyl-, (1R,3aR,4aR,4bR,5S,7aS,8aR,9R,11aS)-
(1R,3R,6R,7S,8S,10R,11R,12R,13S,16S,17R)-8-tert-Butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0.0.0.0]nonadecane-5,15,18-trione
3-tert-butyl hexahydro-4,-7b-11 hydroxy-8-methyl
MFCD05662347
(1R,3R,7S,8S,10R,11R,12R,13S,16S,17R)-8-tert-Butyl-6,12,17-trihydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0.0.0.0]nonadecane-5,15,18-trione
(1R,3R,6R,7S,8S,10R,11S,12R,16S,17R)-6,12,17-Trihydroxy-16-methyl-8-(2-methyl-2-propanyl)-2,4,14,19-tetraoxahexacyclo[8.7.2.0.0.0.0]nonadecane-5,15,18-trione
ginkgolide B from ginkgo leaves
GinkgolideB

Biological Activity

[Description]:

Ginkgolide B, an important active terpenoid from Ginkgo biloba leaves, is reported to increase cell viability and decrease cell apoptosis.IC50 value:Target:In vitro: Ginkgolide B (0.2 or 0.4 μg/ml) was added to the culture medium in vitro led to increases in cell viability and decreases in the number of hippocampal cells undergoing AAPH-induced apoptosis [1]. Ginkgolide B caused a dose-related protection against dysrhythmias; the antiarrhythmic effect of ginkgolide B was comparable to that of diltiazem and superior to the activity of metoprolol. Ginkgolide B can presumably prevent the re-entry mechanism involved in the development of ischemia-induced rhythm disturbances [2].In vivo: Oral administration of ginkgolide B (2 mg/kg/day, p.o.) caused a significant increase in cell viability and a highly significant decrease in the numbers of both spontaneously occurring and AAPH-induced apoptoses.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Others

Natural Products >> Terpenoids and Glycosides

[References]

[1]. Jean R. Rapin, et al. In vitro and in vivo effects of an extract of Ginkgo biloba (EGb 761), ginkgolide B, and bilobalide on apoptosis in primary cultures of rat hippocampal neurons. Drug Development Research, 1998, 45 (1):1-43

[2]. Matyas Koltai, et al. Ginkgolide B protects isolated hearts against arrhythmias induced by ischemia but not reperfusion. European Journal of Pharmacology, 1989, 164 (2): 293-302

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
762.4±60.0 °C at 760 mmHg

[ Melting Point ]:
280°C (dec.)

[ Molecular Formula ]:
C₂₀H₂₄O₁₀

[ Molecular Weight ]:
424.399

[ Flash Point ]:
274.3±26.4 °C

[ Exact Mass ]:
424.136932

[ PSA ]:
148.82000

[ LogP ]:
0.52

[ Vapour Pressure ]:
0.0±5.8 mmHg at 25°C

[ Index of Refraction ]:
1.651

[ Storage condition ]:
2-8°C

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Complete 1H NMR spectral analysis of ten chemical markers of Ginkgo biloba.

Magn. Reson. Chem. 50(8) , 569-75, (2012)

The complete and unambiguous (1)H NMR assignments of ten marker constituents of Ginkgo biloba are described. The comprehensive (1)H NMR profiles (fingerprints) of ginkgolide A, ginkgolide B, ginkgolid...

Mechanistic evaluation of Ginkgo biloba leaf extract-induced genotoxicity in L5178Y cells.

Toxicol. Sci. 139(2) , 338-49, (2014)

Ginkgo biloba has been used for many thousand years as a traditional herbal remedy and its extract has been consumed for many decades as a dietary supplement. Ginkgo biloba leaf extract is a complex m...

Effects of Ginkgo biloba constituents on fruit-infesting behavior of codling moth (Cydia pomonella) in apples.

J. Agric. Food Chem. 59(20) , 10879-86, (2011)

Codling moth, Cydia pomonella (L.), is a cosmopolitan pest of apple, potentially causing severe damage to the fruit. Currently used methods of combating this insect do not warrant full success or are ...