Amentoflavone
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MedKoo CAT#: 600106

CAS#: 1617-53-4

Description: Amentoflavone is a biflavonoid (bis-apigenin coupled at 8 and 3' positions) constituent of a number of plants including Ginkgo biloba, Chamaecyparis obtusa (hinoki), Hypericum perforatum (St. JohnÂ’s Wort) and Xerophyta plicata. Amentoflavone can interact with many medications by being a potent inhibitor of CYP3A4 and CYP2C9, which are enzymes responsible for the metabolism of some drugs in the body. It is also an inhibitor of human cathepsin B. Amentoflavone has a variety of in vitro activities including antimalarial activity, anticancer activity (which may, at least in part, be mediated by its inhibition of fatty acid synthase), and affinities for opioid receptors (as an antagonist) and the allosteric (benzodiazepine) site on the GABAA receptor as a negative allosteric modulator.


Chemical Structure

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Amentoflavone
CAS# 1617-53-4

Theoretical Analysis

MedKoo Cat#: 600106
Name: Amentoflavone
CAS#: 1617-53-4
Chemical Formula: C30H18O10
Exact Mass: 538.09
Molecular Weight: 538.46
Elemental Analysis: C, 66.92; H, 3.37; O, 29.71

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Synonym: Didemethylginkgetin; 38Biapigenin

IUPAC/Chemical Name: 8-[5-(5,7-Dihydroxy-4-oxo-chromen-2-yl)-2-hydroxy-phenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

InChi Key: YUSWMAULDXZHPY-UHFFFAOYSA-N

InChi Code: InChI=1S/C30H18O10/c31-15-4-1-13(2-5-15)24-12-23(38)29-21(36)10-20(35)27(30(29)40-24)17-7-14(3-6-18(17)33)25-11-22(37)28-19(34)8-16(32)9-26(28)39-25/h1-12,31-36H

SMILES Code: O=C1C=C(C2=CC=C(O)C=C2)OC3=C1C(O)=CC(O)=C3C4=CC(C5=CC(C6=C(O5)C=C(O)C=C6O)=O)=CC=C4O

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

Preparing Stock Solutions

The following data is based on the product molecular weight 538.46 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.

Recalculate based on batch purity %
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

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1: Zheng XK, Liu CX, Zhai YY, Li LL, Wang XL, Feng WS. [Protection effect of amentoflavone in Selaginella tamariscina against TNF-alpha-induced vascular injury of endothelial cells]. Yao Xue Xue Bao. 2013 Sep;48(9):1503-9. Chinese. PubMed PMID: 24358788.

2: Zhang J, Liu Z, Cao W, Chen L, Xiong X, Qin S, Zhang Z, Li X, Hu CA. Amentoflavone inhibits angiogenesis of endothelial cells and stimulates apoptosis in hypertrophic scar fibroblasts. Burns. 2014 Aug;40(5):922-9. doi: 10.1016/j.burns.2013.10.012. Epub 2013 Nov 23. PubMed PMID: 24280521.

3: Sakthivel KM, Guruvayoorappan C. Amentoflavone inhibits iNOS, COX-2 expression and modulates cytokine profile, NF-κB signal transduction pathways in rats with ulcerative colitis. Int Immunopharmacol. 2013 Nov;17(3):907-16. doi: 10.1016/j.intimp.2013.09.022. Epub 2013 Oct 12. PubMed PMID: 24126114.

4: Oh J, Rho HS, Yang Y, Yoon JY, Lee J, Hong YD, Kim HC, Choi SS, Kim TW, Shin SS, Cho JY. Extracellular signal-regulated kinase is a direct target of the anti-inflammatory compound amentoflavone derived from Torreya nucifera. Mediators Inflamm. 2013;2013:761506. doi: 10.1155/2013/761506. Epub 2013 Jul 21. PubMed PMID: 23970815; PubMed Central PMCID: PMC3736407.

5: Hwang JH, Choi H, Woo ER, Lee DG. Antibacterial effect of amentoflavone and its synergistic effect with antibiotics. J Microbiol Biotechnol. 2013;23(7):953-8. PubMed PMID: 23727809.

6: Ishola IO, Chaturvedi JP, Rai S, Rajasekar N, Adeyemi OO, Shukla R, Narender T. Evaluation of amentoflavone isolated from Cnestis ferruginea Vahl ex DC (Connaraceae) on production of inflammatory mediators in LPS stimulated rat astrocytoma cell line (C6) and THP-1 cells. J Ethnopharmacol. 2013 Mar 27;146(2):440-8. doi: 10.1016/j.jep.2012.12.015. Epub 2013 Feb 1. PubMed PMID: 23376104.

7: Pei JS, Liu CC, Hsu YN, Lin LL, Wang SC, Chung JG, Bau DT, Lin SS. Amentoflavone induces cell-cycle arrest and apoptosis in MCF-7 human breast cancer cells via mitochondria-dependent pathway. In Vivo. 2012 Nov-Dec;26(6):963-70. PubMed PMID: 23160679.

8: Ishola IO, Chatterjee M, Tota S, Tadigopulla N, Adeyemi OO, Palit G, Shukla R. Antidepressant and anxiolytic effects of amentoflavone isolated from Cnestis ferruginea in mice. Pharmacol Biochem Behav. 2012 Dec;103(2):322-31. doi: 10.1016/j.pbb.2012.08.017. Epub 2012 Aug 24. PubMed PMID: 22944105.

9: Lee JS, Sul JY, Park JB, Lee MS, Cha EY, Song IS, Kim JR, Chang ES. Fatty acid synthase inhibition by amentoflavone suppresses HER2/neu (erbB2) oncogene in SKBR3 human breast cancer cells. Phytother Res. 2013 May;27(5):713-20. doi: 10.1002/ptr.4778. Epub 2012 Jul 5. PubMed PMID: 22767439.

10: Hwang IS, Lee J, Jin HG, Woo ER, Lee DG. Amentoflavone stimulates mitochondrial dysfunction and induces apoptotic cell death in Candida albicans. Mycopathologia. 2012 Apr;173(4):207-18. doi: 10.1007/s11046-011-9503-x. Epub 2011 Dec 31. PubMed PMID: 22210020.