Bergaptol - CAS 486-60-2
Catalog number:
486-60-2
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C11H6O4
Molecular Weight:
202.16
COA:
Inquire
Targets:
Others
Description:
A natural furanocoumarin extract from lemon and bergamot acts as a potent inhibitors of debenzylation activity of CYP3A4 enzyme
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Purity:
≥95%
Appearance:
Solid powder
Synonyms:
4-hydroxyfuro[3,2-g]chromen-7-one; 4-Hydroxy-7H-furo[3,2-g][1]benzopyran-7-one; 4-Hydroxybergapten;
Solubility:
Soluble in DMSO
Storage:
Store at -20 °C
MSDS:
Inquire
Application:
Antiproliferative and anticancer
Quality Standard:
Enterprise Standard
Shelf Life:
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Quantity:
Milligrams-Grams
Melting Point:
275-278 °C
InChIKey:
GIJHDGJRTUSBJR-UHFFFAOYSA-N
InChI:
1S/C11H6O4/c12-10-2-1-6-9(15-10)5-8-7(11(6)13)3-4-14-8/h1-5,13H
Canonical SMILES:
C1=CC(=O)OC2=CC3=C(C=CO3)C(=C21)O
1.Biotransformations of 6',7'-dihydroxybergamottin and 6',7'-epoxybergamottin by the citrus-pathogenic fungi diminish cytochrome P450 3A4 inhibitory activity.
Myung K1, Manthey JA, Narciso JA. Bioorg Med Chem Lett. 2012 Mar 15;22(6):2279-82. doi: 10.1016/j.bmcl.2012.01.081. Epub 2012 Jan 30.
Penicillium digitatum, as well as five other citrus pathogenic species, (Penicillium ulaiense Link, Geotrichum citri Link, Botrytis cinerea P. Micheli ex Pers., Lasiodiplodia theobromae (Pat.) Griffon & Maubl., and Phomopsis citri (teleomorph Diaporthe citri)) were observed to convert 6',7'-epoxybergamottin (1) into 6',7'-dihydroxybergamottin (2), bergaptol (3), and an opened lactone ring metabolite 6,7-furano-5-(6',7'-dihydroxy geranyloxy)-2-hydroxy-hydrocoumaric acid (4). Metabolism of 2 by these fungi also proceeded to 4. The structure of 4 was established by high resolution mass spectrometry and (1)H and (13)C NMR techniques. The inhibitory activity of 4 towards human intestinal cytochrome P450 3A4 (CYP3A4) was greatly decreased (IC(50) >172.0 μM) compared to 2 (IC(50)=0.81 μM).
2.Coumarins from Seseli hartvigii.
Zhang L1, Tosun A, Baba M, Okada Y, Wu L, Okuyama T. Nat Prod Commun. 2010 Jul;5(7):1067-70.
Linear-type furocoumarins, 5-[(2"E,6"R)-6"-hydroxy-3",7"-dimethylocta-2",7"-dienyloxy]psoralen and 5-[(2"E,6"S)-6"-hydroxy-3",7"-dimethylocta-2",7"-dienyloxy]psoralen (1) were first isolated from whole plants of Seseli hartvigii together with one new natural product 6-(3'-methyl-2'-oxo-3'-butenyl)-7-methoxycoumarin (2), and four known compounds (tamarin, bergaptol, notoptol, and a mixture of beta-sitosterol and stigmasterol). The structure of 1 was elucidated by extensive spectroscopic analysis and chemical conversion. The modified Mosher's method and HPLC were applied to determine its stereochemistry. Both R- and S-configurations exist in 1; after modification by Mosher's reagent, they were effectively separated, and their ratio was deduced to be 59% and 41%, respectively.
3.Major furocoumarins in grapefruit juice I: levels and urinary metabolite(s).
Messer A1, Nieborowski A, Strasser C, Lohr C, Schrenk D. Food Chem Toxicol. 2011 Dec;49(12):3224-31. doi: 10.1016/j.fct.2011.09.005. Epub 2011 Sep 12.
Furocoumarins are phototoxic and photogenotoxic natural plant constituents occurring in cosmetics, food and drugs. Grapefruit juice is considered as a major dietary source of furocoumarins although few is known about the variability of furocoumarins in grapefruit juice. We analyzed the major furocoumarins in eight commercial grapefruit juices and in freshly prepared juices made from pink grapefruit obtained from German retailers. Bergaptol was the major furocoumarin in commercial juices, followed by bergamottin and 6',7'-dihydroxy-bergamottin (DHB), whereas an inverse picture (DHB>bergamottin>bergaptol) was obtained in freshly prepared juices. Results from different batches of a single brand of commercial juice, purchased over a period of 7 months, revealed a variability of about 50% for the individual furocoumarins and the sum. In a study with healthy volunteers, consumption of 900 ml commercial grapefruit juice (containing 12.5mg bergaptol, 6.
4.Characterization of coumarin-specific prenyltransferase activities in Citrus limon peel.
Munakata R1, Inoue T, Koeduka T, Sasaki K, Tsurumaru Y, Sugiyama A, Uto Y, Hori H, Azuma J, Yazaki K. Biosci Biotechnol Biochem. 2012;76(7):1389-93. Epub 2012 Jul 7.
Coumarins, a large group of polyphenols, play important roles in the defense mechanisms of plants, and they also exhibit various biological activities beneficial to human health, often enhanced by prenylation. Despite the high abundance of prenylated coumarins in citrus fruits, there has been no report on coumarin-specific prenyltransferase activity in citrus. In this study, we detected both O- and C-prenyltransferase activities of coumarin substrates in a microsome fraction prepared from lemon (Citrus limon) peel, where large amounts of prenylated coumarins accumulate. Bergaptol was the most preferred substrate out of various coumarin derivatives tested, and geranyl diphosphate (GPP) was accepted exclusively as prenyl donor substrate. Further enzymatic characterization of bergaptol 5-O-geranyltransferase activity revealed its unique properties: apparent K(m) values for GPP (9 µM) and bergaptol (140 µM) and a broad divalent cation requirement.
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CAS 486-60-2 Bergaptol

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