Ginkgolic acid | CAS#22910-60-7

MedKoo Cat#: 540159 | Name: Ginkgolic acid

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ginkgolic acid is an HIV protease and fatty acid synthase inhibitor found in Ginkgo. It suppresses HIV infection, inhibits growth of Staphyloccus, Escherichia, and Bacillus, increases activity of PP2C in neurons, and induces apoptosis in cancer cells.

Chemical Structure

Ginkgolic acid

CAS#22910-60-7

Theoretical Analysis

MedKoo Cat#: 540159

Name: Ginkgolic acid

CAS#: 22910-60-7

Chemical Formula: C22H34O3

Exact Mass: 346.2508

Molecular Weight: 346.51

Elemental Analysis: C, 76.26; H, 9.89; O, 13.85

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 450.00	2 Weeks
10mg	USD 850.00	2 Weeks

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Related CAS #

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Synonym

Ginkgoic acid monoene; Anacardic Acid 15:1; Ginkgolic Acid I; Ginkogolic Acid C15:1

IUPAC/Chemical Name

(Z)-2-hydroxy-6-(pentadec-8-en-1-yl)benzoic acid

InChi Key

YXHVCZZLWZYHSA-FPLPWBNLSA-N

InChi Code

InChI=1S/C22H34O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(23)21(19)22(24)25/h7-8,15,17-18,23H,2-6,9-14,16H2,1H3,(H,24,25)/b8-7-

SMILES Code

O=C(O)C1=C(CCCCCCC/C=C\CCCCCC)C=CC=C1O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ginkgolic Acid is a natural compound that inhibits SUMOylation with an IC50 of 3.0 μM in in vitro assay.

In vitro activity:

The proliferation inhibition rate of OCa (ovarian cancer) cells in each treatment concentration of GA (ginkgolic acid) treatment group was higher than that of the control group (P < 0.05), and the inhibitory effect was enhanced as the concentration of GA increases (Figure 1(a)). Meanwhile, Figure 1(b) shows that the OD value of OCa cells treated with GA observed in CCK-8 test decreased in comparison to the DMSO (0.1%) control group, suggesting an attenuated proliferative ability induced by GA (Figure 1(b)). Consistent to the changes in cell proliferation, the migration capacity of OCa cells was also attenuated by treatment of GA (Figure 1(c)). Reference: Evid Based Complement Alternat Med. 2021 Dec 26;2021:5481271. https://pubmed.ncbi.nlm.nih.gov/34987594/

In vivo activity:

HE (hematoxylin and eosin) results showed that compared with the BLM (bleomycin) model group, the GA (ginkgolic acid) administration group had significantly reduced structural lung damage and inflammation, which was inhibited in SENP1-KO animals. Similarly, Masson staining results showed that overall levels of fibrosis and structural lung injury were significantly improved following GA administration, but this effect was lost in SENP1-KO mice. These results indicated that GA prevented PF through SENP1. Reference: Oxid Med Cell Longev. 2022 Jun 6;2022:8002566. https://pubmed.ncbi.nlm.nih.gov/35707278/

	Solvent	mg/mL	mM
Solubility
	DMSO	67.3	194.29
	Ethanol	34.7	100.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 346.51 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Fei Z, Yu Y, Xiang M, Luo F. Ginkgolic Acid (GA) Inhibits the Growth of OCa by Inhibiting lncRNA MALAT1/JAK2 Axis. Evid Based Complement Alternat Med. 2021 Dec 26;2021:5481271. doi: 10.1155/2021/5481271. PMID: 34987594; PMCID: PMC8720594. 2. Zhu C, Na N, Sheng H, Feng B, Wang H, Zhu P, Zhang W, Zhang M, Deng Z. Ginkgolic acid inhibits the growth of renal cell carcinoma cells via inactivation of the EGFR signaling pathway. Exp Ther Med. 2020 Apr;19(4):2949-2956. doi: 10.3892/etm.2020.8570. Epub 2020 Feb 27. PMID: 32256780; PMCID: PMC7086188. 3. Yu L, Bian X, Zhang C, Wu Z, Huang N, Yang J, Jin W, Feng Z, Li D, Huo X, Wu T, Jiang Z, Liu X, Sun D. Ginkgolic acid improves bleomycin-induced pulmonary fibrosis by inhibiting SMAD4 SUMOylation. Oxid Med Cell Longev. 2022 Jun 6;2022:8002566. doi: 10.1155/2022/8002566. PMID: 35707278; PMCID: PMC9192210. 4. Bhutta MS, Shechter O, Gallo ES, Martin SD, Jones E, Doncel GF, Borenstein R. Ginkgolic Acid Inhibits Herpes Simplex Virus Type 1 Skin Infection and Prevents Zosteriform Spread in Mice. Viruses. 2021 Jan 9;13(1):86. doi: 10.3390/v13010086. PMID: 33435520; PMCID: PMC7826900.

In vitro protocol:

In vivo protocol:

1. Yu L, Bian X, Zhang C, Wu Z, Huang N, Yang J, Jin W, Feng Z, Li D, Huo X, Wu T, Jiang Z, Liu X, Sun D. Ginkgolic acid improves bleomycin-induced pulmonary fibrosis by inhibiting SMAD4 SUMOylation. Oxid Med Cell Longev. 2022 Jun 6;2022:8002566. doi: 10.1155/2022/8002566. PMID: 35707278; PMCID: PMC9192210. 2. Bhutta MS, Shechter O, Gallo ES, Martin SD, Jones E, Doncel GF, Borenstein R. Ginkgolic Acid Inhibits Herpes Simplex Virus Type 1 Skin Infection and Prevents Zosteriform Spread in Mice. Viruses. 2021 Jan 9;13(1):86. doi: 10.3390/v13010086. PMID: 33435520; PMCID: PMC7826900.

1: Wang R, Kobayashi Y, Lin Y, Rauwald HW, Yao J, Fang L, Qiao H, Kuchta K. HPLC quantification of all five ginkgolic acid derivatives in Ginkgo biloba extracts using 13 : 0 ginkgolic acid as a single marker compound. Planta Med. 2015 Jan;81(1):71-8. doi: 10.1055/s-0034-1383312. Epub 2014 Dec 17. PubMed PMID: 25519835. 2: Maleeva G, Buldakova S, Bregestovski P. Selective potentiation of alpha 1 glycine receptors by ginkgolic acid. Front Mol Neurosci. 2015 Oct 29;8:64. doi: 10.3389/fnmol.2015.00064. eCollection 2015. PubMed PMID: 26578878; PubMed Central PMCID: PMC4624854. 3: Fu Y, Hong S, Li D, Liu S. Novel chemical synthesis of ginkgolic acid (13:0) and evaluation of its tyrosinase inhibitory activity. J Agric Food Chem. 2013 Jun 5;61(22):5347-52. doi: 10.1021/jf4012642. Epub 2013 May 23. PubMed PMID: 23701207. 4: Ma J, Duan W, Han S, Lei J, Xu Q, Chen X, Jiang Z, Nan L, Li J, Chen K, Han L, Wang Z, Li X, Wu E, Huo X. Ginkgolic acid suppresses the development of pancreatic cancer by inhibiting pathways driving lipogenesis. Oncotarget. 2015 Aug 28;6(25):20993-1003. PubMed PMID: 25895130; PubMed Central PMCID: PMC4673245. 5: Fukuda I, Ito A, Hirai G, Nishimura S, Kawasaki H, Saitoh H, Kimura K, Sodeoka M, Yoshida M. Ginkgolic acid inhibits protein SUMOylation by blocking formation of the E1-SUMO intermediate. Chem Biol. 2009 Feb 27;16(2):133-40. doi: 10.1016/j.chembiol.2009.01.009. PubMed PMID: 19246003. 6: Maleeva G, Buldakova S, Bregestovski P. Ginkgolic acid specifically potentiates alpha 1 glycine receptors. Springerplus. 2015 Jun 12;4(Suppl 1):L31. doi: 10.1186/2193-1801-4-S1-L31. eCollection 2015. PubMed PMID: 27057478; PubMed Central PMCID: PMC4796240. 7: Lü JM, Yan S, Jamaluddin S, Weakley SM, Liang Z, Siwak EB, Yao Q, Chen C. Ginkgolic acid inhibits HIV protease activity and HIV infection in vitro. Med Sci Monit. 2012 Aug;18(8):BR293-298. PubMed PMID: 22847190; PubMed Central PMCID: PMC3560711. 8: Jiang L, Si ZH, Li MH, Zhao H, Fu YH, Xing YX, Hong W, Ruan LY, Li PM, Wang JS. (1)H NMR-based metabolomics study of liver damage induced by ginkgolic acid (15:1) in mice. J Pharm Biomed Anal. 2017 Mar 20;136:44-54. doi: 10.1016/j.jpba.2016.12.033. Epub 2016 Dec 29. PubMed PMID: 28063335. 9: Xia H, Liu Z, Hu H, Zhou H, Zeng S. Identification of ginkgolic acid (15:1) metabolites in rats following oral administration by high-performance liquid chromatography coupled to tandem mass spectrometry. Xenobiotica. 2013 May;43(5):454-60. doi: 10.3109/00498254.2012.725141. Epub 2012 Dec 4. PubMed PMID: 23205533. 10: Liu P, Pan S. [Advance in study of ginkgolic acid contained in Ginkgo biloba preparations]. Zhongguo Zhong Yao Za Zhi. 2012 Feb;37(3):274-7. Review. Chinese. PubMed PMID: 22568222. 11: Oh J, Hwang IH, Hong CE, Lyu SY, Na M. Inhibition of fatty acid synthase by ginkgolic acids from the leaves of Ginkgo biloba and their cytotoxic activity. J Enzyme Inhib Med Chem. 2013 Jun;28(3):565-8. doi: 10.3109/14756366.2012.658786. Epub 2012 Mar 1. PubMed PMID: 22380770. 12: Liu ZH, Zeng S. Cytotoxicity of ginkgolic acid in HepG2 cells and primary rat hepatocytes. Toxicol Lett. 2009 Jun 22;187(3):131-6. doi: 10.1016/j.toxlet.2009.02.012. Epub 2009 Feb 21. PubMed PMID: 19429255. 13: Mango D, Weisz F, Nisticò R. Ginkgolic Acid Protects against Aβ-Induced Synaptic Dysfunction in the Hippocampus. Front Pharmacol. 2016 Oct 26;7:401. eCollection 2016. PubMed PMID: 27833555; PubMed Central PMCID: PMC5080287. 14: Baek SH, Ko JH, Lee JH, Kim C, Lee H, Nam D, Lee J, Lee SG, Yang WM, Um JY, Sethi G, Ahn KS. Ginkgolic Acid Inhibits Invasion and Migration and TGF-β-Induced EMT of Lung Cancer Cells Through PI3K/Akt/mTOR Inactivation. J Cell Physiol. 2017 Feb;232(2):346-354. doi: 10.1002/jcp.25426. Epub 2016 Jun 2. PubMed PMID: 27177359. 15: Yang X, Zhu W, Chen J, Qian Z, Xie J. [Study on anti-bacterium activity of ginkgolic acids and their momomers]. Zhong Yao Cai. 2004 Sep;27(9):661-3. Chinese. PubMed PMID: 15704587. 16: Liu ZH, Chen J, Yu LS, Jiang HD, Yao TW, Zeng S. Structural elucidation of metabolites of ginkgolic acid in rat liver microsomes by ultra-performance liquid chromatography/electrospray ionization tandem mass spectrometry and hydrogen/deuterium exchange. Rapid Commun Mass Spectrom. 2009 Jul;23(13):1899-906. doi: 10.1002/rcm.4086. PubMed PMID: 19462408. 17: Lee JH, Kim YG, Ryu SY, Cho MH, Lee J. Ginkgolic acids and Ginkgo biloba extract inhibit Escherichia coli O157:H7 and Staphylococcus aureus biofilm formation. Int J Food Microbiol. 2014 Mar 17;174:47-55. doi: 10.1016/j.ijfoodmicro.2013.12.030. Epub 2014 Jan 5. PubMed PMID: 24457153. 18: Yang XM, Wang YF, Li YY, Ma HL. Thermal stability of ginkgolic acids from Ginkgo biloba and the effects of ginkgol C17:1 on the apoptosis and migration of SMMC7721 cells. Fitoterapia. 2014 Oct;98:66-76. doi: 10.1016/j.fitote.2014.07.003. Epub 2014 Jul 10. PubMed PMID: 25016955. 19: Yang LQ, Wu XY, Chen J. [Determination of ginkgolic acids by high performance liquid chromatography]. Yao Xue Xue Bao. 2002 Jul;37(7):555-8. Chinese. PubMed PMID: 12914328. 20: Xia H, Wang X, Li L, Wang S, Guo C, Liu Y, Yu L, Jiang H, Zeng S. Development of high performance liquid chromatography/electrospray ionization mass spectrometry for assay of ginkgolic acid (15:1) in rat plasma and its application to pharmacokinetics study. J Chromatogr B Analyt Technol Biomed Life Sci. 2010 Oct 15;878(28):2701-6. doi: 10.1016/j.jchromb.2010.08.009. Epub 2010 Aug 17. PubMed PMID: 20829122.