Ginkgolide B

Modify Date: 2024-01-03 08:58:42

Ginkgolide B Structure
Ginkgolide B structure
 Common Name Ginkgolide B
CAS Number 15291-77-7 Molecular Weight 424.399
Density 1.6±0.1 g/cm3 Boiling Point 762.4±60.0 °C at 760 mmHg
Molecular Formula C20H24O10 Melting Point 280°C (dec.)
MSDS USA Flash Point 274.3±26.4 °C

 Use of Ginkgolide B


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.

 Names

Name Ginkgolide B
Synonym More Synonyms

 Ginkgolide B 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
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

 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

α-benzylginkgolide B structure

α-benzylginkgolide B

CAS#:170288-58-1

~95%

Ginkgolide B Structure

Ginkgolide B

CAS#:15291-77-7
Literature: Jaracz, Stanislav; Malik, Shahid; Nakanishi, Koji Phytochemistry, 2004 , vol. 65, # 21 SPEC. ISS. p. 2897 - 2902
N/A structure

N/A

CAS#:145473-36-5

~%

Ginkgolide B Structure

Ginkgolide B

CAS#:15291-77-7
Literature: Tetrahedron Letters, , vol. 33, # 46 p. 6955 - 6958
N/A structure

N/A

CAS#:130523-06-7

~73%

Ginkgolide B Structure

Ginkgolide B

CAS#:15291-77-7
Literature: Weinges, Klaus; Schick, Hartmut Liebigs Annalen der Chemie, 1991 , # 1 p. 81 - 83
Ginkgolide C structure

Ginkgolide C

CAS#:15291-76-6

~%

Ginkgolide B Structure

Ginkgolide B

CAS#:15291-77-7
Literature: Tetrahedron Letters, , vol. 33, # 46 p. 6955 - 6958
N/A structure

N/A

CAS#:145497-37-6

~%

Ginkgolide B Structure

Ginkgolide B

CAS#:15291-77-7
Literature: Tetrahedron Letters, , vol. 33, # 46 p. 6955 - 6958
N/A structure

N/A

CAS#:145497-38-7

~%

Ginkgolide B Structure

Ginkgolide B

CAS#:15291-77-7
Literature: Tetrahedron Letters, , vol. 33, # 46 p. 6955 - 6958
1-O-(tert-Butyldiphenylsilyl)ginkgolid C structure

1-O-(tert-Butyl...

CAS#:130523-04-5

~%

Ginkgolide B Structure

Ginkgolide B

CAS#:15291-77-7
Literature: Liebigs Annalen der Chemie, , # 1 p. 81 - 83
1-O-(tert-Butyldiphenylsilyl)-7-O-(phenyloxythiocarbonyl)ginkgolid C structure

1-O-(tert-Butyl...

CAS#:130523-05-6

~%

Ginkgolide B Structure

Ginkgolide B

CAS#:15291-77-7
Literature: Liebigs Annalen der Chemie, , # 1 p. 81 - 83
N/A structure

N/A

CAS#:173102-79-9

~%

Ginkgolide B Structure

Ginkgolide B

CAS#:15291-77-7
Literature: Bioorganic and Medicinal Chemistry Letters, , vol. 14, # 22 p. 5673 - 5675

 Articles31

More 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 ...

 Synonyms

(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
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