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MedKoo Cat#: 600106 | Name: Amentoflavone
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Description:

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

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

Amentoflavone
Amentoflavone
CAS#1617-53-4

Theoretical Analysis

MedKoo Cat#: 600106

Name: Amentoflavone

CAS#: 1617-53-4

Chemical Formula: C30H18O10

Exact Mass: 538.0900

Molecular Weight: 538.46

Elemental Analysis: C, 66.92; H, 3.37; O, 29.71

Price and Availability

Size Price Availability Quantity
10mg USD 250.00 2 Weeks
25mg USD 450.00 2 Weeks
50mg USD 750.00 2 Weeks
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Related CAS #
No Data
Synonym
Amentoflavone; Amenthoflavone; Tridemethylsciadopitysin; Didemethylginkgetin; 38Biapigenin; Didemethyl Ginkgetin; NSC 295677; NSC295677; NSC-295677;
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
More Info

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
1: Xiong X, Tang N, Lai X, Zhang J, Wen W, Li X, Li A, Wu Y, Liu Z. Insights Into Amentoflavone: A Natural Multifunctional Biflavonoid. Front Pharmacol. 2021 Dec 22;12:768708. doi: 10.3389/fphar.2021.768708. PMID: 35002708; PMCID: PMC8727548. 2: Zhuang JL, Liu YY, Li ZZ, Zhuang QZ, Tang WZ, Xiong Y, Huang XZ. Amentoflavone prevents ox-LDL-induced lipid accumulation by suppressing the PPARγ/CD36 signal pathway. Toxicol Appl Pharmacol. 2021 Nov 15;431:115733. doi: 10.1016/j.taap.2021.115733. Epub 2021 Sep 29. PMID: 34599948. 3: Chen Y, Li N, Wang H, Wang N, Peng H, Wang J, Li Y, Liu M, Li H, Zhang Y, Wang Z. Amentoflavone suppresses cell proliferation and induces cell death through triggering autophagy-dependent ferroptosis in human glioma. Life Sci. 2020 Apr 15;247:117425. doi: 10.1016/j.lfs.2020.117425. Epub 2020 Feb 11. PMID: 32057904. 4: Tingting W, Tianqi F, Xinyu W, Can Z, Xue S, Xuming D, Jianfeng W. Amentoflavone attenuates Listeria monocytogenes pathogenicity through an LLO- dependent mechanism. Br J Pharmacol. 2022 Jul;179(14):3839-3858. doi: 10.1111/bph.15827. Epub 2022 Mar 28. PMID: 35229287. 5: Tuli HS, Joshi H, Vashishth K, Ramniwas S, Varol M, Kumar M, Rani I, Rani V, Sak K. Chemopreventive mechanisms of amentoflavone: recent trends and advancements. Naunyn Schmiedebergs Arch Pharmacol. 2023 May;396(5):865-876. doi: 10.1007/s00210-023-02416-6. Epub 2023 Feb 11. PMID: 36773053. 6: Cai K, Yang Y, Guo ZJ, Cai RL, Hashida H, Li HX. Amentoflavone inhibits colorectal cancer epithelial-mesenchymal transition via the miR-16-5p/HMGA2/β-catenin pathway. Ann Transl Med. 2022 Sep;10(18):1009. doi: 10.21037/atm-22-3035. PMID: 36267717; PMCID: PMC9577732. 7: Zhao F, Qian Y, Li H, Yang Y, Wang J, Yu W, Li M, Cheng W, Shan L. Amentoflavone-loaded nanoparticles enhanced chemotherapy efficacy by inhibition of AKR1B10. Nanotechnology. 2022 Jun 28;33(38). doi: 10.1088/1361-6528/ac7810. PMID: 35697009. 8: Rong S, Yang C, Wang F, Wu Y, Sun K, Sun T, Wu Z. Amentoflavone Exerts Anti- Neuroinflammatory Effects by Inhibiting TLR4/MyD88/NF-κB and Activating Nrf2/HO-1 Pathway in Lipopolysaccharide-Induced BV2 Microglia. Mediators Inflamm. 2022 Dec 6;2022:5184721. doi: 10.1155/2022/5184721. PMID: 36523959; PMCID: PMC9747320. 9: Park HJ, Kim MM. Amentoflavone Induces Autophagy and Modulates p53. Cell J. 2019 Apr;21(1):27-34. doi: 10.22074/cellj.2019.5717. Epub 2018 Nov 18. PMID: 30507085; PMCID: PMC6275431. 10: Rizk YS, Hardoim DJ, Santos KBA, Zaverucha-do-Valle T, Taniwaki NN, Almeida- Souza F, Carollo CA, Vannier-Santos MA, Arruda CCP, Calabrese KDS. Amentoflavone isolated from Selaginella sellowii Hieron induces mitochondrial dysfunction in Leishmania amazonensis promastigotes. Parasitol Int. 2022 Feb;86:102458. doi: 10.1016/j.parint.2021.102458. Epub 2021 Sep 9. PMID: 34509671. 11: Sun K, Xie R, Yi Z, Yin L, Guan Y, Wang L, Wang Y, Ding X, Luan Y, Liu H, Fan Y. Amentoflavone impairs the reconsolidated fear memories through inhibition of ERK pathway. Biochem Biophys Res Commun. 2022 Sep 24;622:8-14. doi: 10.1016/j.bbrc.2022.07.024. Epub 2022 Jul 8. PMID: 35841770. 12: Yu S, Yan H, Zhang L, Shan M, Chen P, Ding A, Li SF. A Review on the Phytochemistry, Pharmacology, and Pharmacokinetics of Amentoflavone, a Naturally-Occurring Biflavonoid. Molecules. 2017 Feb 16;22(2):299. doi: 10.3390/molecules22020299. PMID: 28212342; PMCID: PMC6155574. 13: Han BH, Cofell B, Everhart E, Humpal C, Kang SS, Lee SK, Kim-Han JS. Amentoflavone Promotes Cellular Uptake and Degradation of Amyloid-Beta in Neuronal Cells. Int J Mol Sci. 2022 May 24;23(11):5885. doi: 10.3390/ijms23115885. PMID: 35682567; PMCID: PMC9180170. 14: Lee KC, Chen WT, Liu YC, Lin SS, Hsu FT. Amentoflavone Inhibits Hepatocellular Carcinoma Progression Through Blockage of ERK/NF-ĸB Activation. In Vivo. 2018 Sep-Oct;32(5):1097-1103. doi: 10.21873/invivo.11351. PMID: 30150431; PMCID: PMC6199595. 15: Lee H, Kim SY, Lee SW, Kwak S, Li H, Piao R, Park HY, Choi S, Jeong TS. Amentoflavone-Enriched Selaginella rossii Protects against Ultraviolet- and Oxidative Stress-Induced Aging in Skin Cells. Life (Basel). 2022 Dec 14;12(12):2106. doi: 10.3390/life12122106. PMID: 36556471; PMCID: PMC9787533. 16: Lee KC, Tsai JJ, Tseng CW, Kuo YC, Chuang YC, Lin SS, Hsu FT. Amentoflavone Inhibits ERK-modulated Tumor Progression in Hepatocellular Carcinoma In Vitro. In Vivo. 2018 May-Jun;32(3):549-554. doi: 10.21873/invivo.11274. PMID: 29695559; PMCID: PMC6000793. 17: Cao B, Zeng M, Zhang Q, Zhang B, Cao Y, Wu Y, Feng W, Zheng X. Amentoflavone Ameliorates Memory Deficits and Abnormal Autophagy in Aβ25-35-Induced Mice by mTOR Signaling. Neurochem Res. 2021 Apr;46(4):921-934. doi: 10.1007/s11064-020-03223-8. Epub 2021 Jan 25. PMID: 33492604. 18: Rizk YS, Santos-Pereira S, Gervazoni L, Hardoim DJ, Cardoso FO, de Souza CDSF, Pelajo-Machado M, Carollo CA, de Arruda CCP, Almeida-Amaral EE, Zaverucha- do-Valle T, Calabrese KDS. Amentoflavone as an Ally in the Treatment of Cutaneous Leishmaniasis: Analysis of Its Antioxidant/Prooxidant Mechanisms. Front Cell Infect Microbiol. 2021 Feb 25;11:615814. doi: 10.3389/fcimb.2021.615814. PMID: 33718267; PMCID: PMC7950538. 19: Chen WT, Chen CH, Su HT, Yueh PF, Hsu FT, Chiang IT. Amentoflavone Induces Cell-cycle Arrest, Apoptosis, and Invasion Inhibition in Non-small Cell Lung Cancer Cells. Anticancer Res. 2021 Mar;41(3):1357-1364. doi: 10.21873/anticanres.14893. PMID: 33788727. 20: Lee J, Kim M, Jeong SE, Park HY, Jeon CO, Park W. Amentoflavone, a novel cyanobacterial killing agent from Selaginella tamariscina. J Hazard Mater. 2020 Feb 15;384:121312. doi: 10.1016/j.jhazmat.2019.121312. Epub 2019 Oct 14. PMID: 31699478.