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Ginkgolic acid C13:0

CAS# 20261-38-5

Ginkgolic acid C13:0

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Quality Control of Ginkgolic acid C13:0

Number of papers citing our products

Chemical structure

Ginkgolic acid C13:0

3D structure

Chemical Properties of Ginkgolic acid C13:0

Cas No. 20261-38-5 SDF Download SDF
PubChem ID 161306 Appearance White powder
Formula C20H32O3 M.Wt 320.47
Type of Compound Phenols Storage Desiccate at -20°C
Synonyms Ginkgolic acid (13:0); Ginkgoneolic Acid; 6-Tridecylsalicylic acid
Solubility Soluble in methan
Chemical Name 2-hydroxy-6-tridecylbenzoic acid
SMILES CCCCCCCCCCCCCC1=C(C(=CC=C1)O)C(=O)O
Standard InChIKey VEPUCZUJLKAVNM-UHFFFAOYSA-N
Standard InChI InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-14-17-15-13-16-18(21)19(17)20(22)23/h13,15-16,21H,2-12,14H2,1H3,(H,22,23)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Ginkgolic acid C13:0

The leaves of Ginkgo biloba L.

Biological Activity of Ginkgolic acid C13:0

DescriptionGinkgolic acid C13:0 has a wide antimicrobial spectrum against E.coli and bacillus subtilis who are bacterias, and penicillium, penicillum purpurogenum, penicillium camemberti and aspergillus niger who are fungis, and the MIC of it against E.coli, bacillus subtilis and penicillium is 7.5, 15, 25 mg/mL seperately. It is a natural anticariogenic agent in that it exhibits antimicrobial activity against S. mutans and suppresses the specific virulence factors associated with its cariogenicity. Ginkgolic acid C13:0 exhibits the high α-glucosidase inhibitory activity; Ginkgolic acid C13:0 represents a new kind of molluscicide agent , it has a pronounced effect on snail mitochondria with gross ultrastructural changes.
TargetsAntifection | α-glucosidase
In vitro

Purification, identification and the antimicrobial activity of ginkgolic acids in ginkgo seeds.[Reference: WebLink]

Journal of Chinese Institute of Food Science and Technology. 2015, 15(3):207-15.

Ginkgo seeds were used as materials in this experiment, Ginkgolic acids in ginkgo seeds were extracted by ethanol, and the ethanol extract were further extracted with petroleum ether.
METHODS AND RESULTS:
The purification process of the ginkgolic acids were studied, and the compositions and contents were analyzed and detected by the methods of combination of HPLC and LC-MS. And two bacterias and four fungis were used for tested strains, the antimicrobial activity of ginkgolic acids were tested and the minimal inhibitory concentration (MIC) were determined separately. The results show that taking 89:1:11 system of petroleum ether, ethyl ether, and methanol as eluents, at 1.2 mL/min velocity, the effect of the silica gel column chromatography purification is the better. HPLC and LC -MS analysis showed that ginkgolic acids in ginkgo seeds consists chiefly of Ginkgolic acid C13:0, C15:1, C17:2, C15:0, C17:1. The content of ginkgolic acids in skimmed ginkgo powder is 0.11 g/kg by the C13:0, C15:1, C17:1 and the content of Ginkgolic acid C13:0, C15:1, C17:1 is 0.013, 0.042, 0.055 g/kg separately.
CONCLUSIONS:
The antimicrobial tests showed that ginkgolic acids had a wide antimicrobial spectrum against E.coli and bacillus subtilis who are bacterias, and penicillium, penicillum purpurogenum, penicillium camemberti and aspergillus niger who are fungis. And the MIC of the ginkgolic acids against E.coli, bacillus subtilis and penicillium is 7.5, 15, 25 mg/mL seperately.

In vivo

In vivo assessment of anthelmintic efficacy of ginkgolic acids (C13:0, C15:1) on removal of Pseudodactylogyrus in European eel[Reference: WebLink]

Aquaculture, 2009, 297(1-4):38-43.

Pseudodactylogyrus is a significant monogenean parasite of the gills of aquacultured European eels, and can cause severe gill pathology. In this study, effects of the crude extracts, fractions and compounds of exopleura of Ginkgo biloba against Pseudodactylogyrus were investigated under in vivo conditions by bio-assay guided isolation method.
METHODS AND RESULTS:
Four solvents (petroleum ether, ethyl acetate, n-butanol and water) were applied for the extraction of exopleura of G. biloba. Among them, only the petroleum ether extract showed strong activity and therefore, subjected to further separation and purification using various chromatographic techniques. Two compounds showing potent activity were identified by comparing spectral data (IR, NMR, and EI-MS) with literature values to be Ginkgolic acid C13:0 and C15:1. They were found to be 100% effective at the concentration of 2.5 mg l- 1 and 6.0 mg l- 1, with ED50 values of 0.72 mg l- 1 and 2.88 mg l- 1, respectively. In the 5-days safety test, Ginkgolic acid C13:0 and C15:1 were shown to be safe for healthy juvenile eels when the concentration were up to 10.0 and 18.0 mg l- 1, respectively.
CONCLUSIONS:
The two compounds exhibited potential results and can be explored as plant-derived antiparasitic for the control of Pseudodactylogyrus.

Protocol of Ginkgolic acid C13:0

Kinase Assay

Potent α-glucosidase inhibitors isolated from Ginkgo biloba leaves.[Pubmed: 26027162]

Pak J Biol Sci. 2014 Nov;17(11):1170-8.

In vitro α-glucosidase inhibitory activity of Ginkgo biloba leaves was investigated.
METHODS AND RESULTS:
The inhibitory activity of methanol extracts from yellow and green leaves was 13.8 and 40.1 μg mL(-1), respectively. Each methanol extract was separated into its respective fraction by solvent-solvent extraction with n-hexane, chloroform, ethyl acetate and n-butanol. The n-hexane fractions (in both methanol extracts from green and yellow leaves) exhibited high α-glucosidase inhibitory activity with IC50 values of 13.6 and 13.4 μg mL(-1), respectively. Further fractionation of the n-hexane fractions by silica gel column chromatography gave the most active fraction which was identified as Ginkgolic acid C13:0 and a mixture (C13:0, C15:0, C15: 1, C17:1 and C17:2). Ginkgolic acid C13:0 exhibited the highest α-glucosidase inhibitory activity.
CONCLUSIONS:
This is the first study to successfully isolate ginkgolic acids as α-glucosidase inhibitors.

Animal Research

Effects of the molluscicidal agent GA-C13:0, a natural occurring ginkgolic acid, on snail mitochondria.[Reference: WebLink]

Pestic. Biochem. Phys., 2012, 103(2):115-20.

Ginkgolic acids (GAs) from the leaves and sarcotesta of Ginkgo biloba L. represent a new kind of molluscicide agent. To date, the mechanism(s) for the observed molluscicidal activity remains largely unknown. Since Ginkgolic acid C13:0(GA-C13:0) has effectively inhibited snail mobility, we examined the effects of the compound on mitochondrial function and gene expression as compared to niclosamide.
METHODS AND RESULTS:
Snail mitochondrial damage induced by GAs was tested using transmission electron microscopy (TEM) and gene-expression profiling of five mitochondrial enzymes using real-time PCR. GA-C13:0 was found to have a pronounced effect on snail mitochondria with gross ultrastructural changes. In addition, GA-C13:0 was also found to inhibit the gene expression of four mitochondrial enzymes including cytochrome c oxidase, adenosine triphosphate (ATP) synthase, cytochrome b and dihydronicotinamide adenine dinucleotide (NADH) dehydrogenase. In contrast, niclosamide did not show such effects on mitochondrial function and gene expression, suggesting that the molluscicidal activity of GA-C13:0 and niclosamide differed.
CONCLUSIONS:
Our results imply that snail mitochondria are a potential target for the molluscicidal activity of ginkgolic acids.

Ginkgolic acid C13:0 Dilution Calculator

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Preparing Stock Solutions of Ginkgolic acid C13:0

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.1204 mL 15.6021 mL 31.2042 mL 62.4083 mL 78.0104 mL
5 mM 0.6241 mL 3.1204 mL 6.2408 mL 12.4817 mL 15.6021 mL
10 mM 0.312 mL 1.5602 mL 3.1204 mL 6.2408 mL 7.801 mL
50 mM 0.0624 mL 0.312 mL 0.6241 mL 1.2482 mL 1.5602 mL
100 mM 0.0312 mL 0.156 mL 0.312 mL 0.6241 mL 0.7801 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Ginkgolic acid C13:0

Ginkgolic Acid (C13:0) is a natural anticariogenic agent in that it exhibits antimicrobial activity against S. mutans and suppresses the specific virulence factors associated with its cariogenicity. IC50 value: Inhibiting the biofilm formation of S. mutans (MBIC (50) = 4 μg/mL); reduced 1-day-developed biofilm of S. mutans by 50 % or more at low concentration (MBRC (50) = 32 μg/mL). Target: In vitro: Ginkgolic Acid (C13:0) inhibited not only the growth of S. mutans planktonic cells at minimum inhibitory concentration (MIC) of 4 μg/mL and minimum bactericidal concentration (MBC) of 8 μg/mL but also the acid production and adherence to saliva-coated hydroxyapatite of S. mutans at sub-MIC concentration. In addition, this agent was effective in inhibiting the biofilm formation of S. mutans (MBIC (50) = 4 μg/mL), and it reduced 1-day-developed biofilm of S. mutans by 50 % or more at low concentration (MBRC (50) = 32 μg/mL). Furthermore Ginkgolic Acid (C13:0) disrupted biofilm integrity effectively [1]. In vivo:

References:
[1]. He J, et al. Effects of ginkgoneolic acid on the growth, acidogenicity, adherence, and biofilm of Streptococcus mutans in vitro. Folia Microbiol (Praha). 2013 Mar;58(2):147-53.

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References on Ginkgolic acid C13:0

Potent alpha-glucosidase inhibitors isolated from Ginkgo biloba leaves.[Pubmed:26027162]

Pak J Biol Sci. 2014 Nov;17(11):1170-8.

In vitro alpha-glucosidase inhibitory activity of Ginkgo biloba leaves was investigated. The inhibitory activity of methanol extracts from yellow and green leaves was 13.8 and 40.1 mug mL(-1), respectively. Each methanol extract was separated into its respective fraction by solvent-solvent extraction with n-hexane, chloroform, ethyl acetate and n-butanol. The n-hexane fractions (in both methanol extracts from green and yellow leaves) exhibited high alpha-glucosidase inhibitory activity with IC50 values of 13.6 and 13.4 mug mL(-1), respectively. Further fractionation of the n-hexane fractions by silica gel column chromatography gave the most active fraction which was identified as ginkgolic acid (C13:0) and a mixture (C13:0, C15:0, C15: 1, C17:1 and C17:2). Ginkgolic acid (C13:0) exhibited the highest alpha-glucosidase inhibitory activity. This is the first study to successfully isolate ginkgolic acids as alpha-glucosidase inhibitors.

Description

Ginkgolic Acid (C13:0) is a natural anticariogenic agent in that it exhibits antimicrobial activity against S.

Keywords:

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