Bergamottin

Article number:

7500944

CAS No.:

7380-40-7

Formula:

C21H22O4

Chemical description:

7H-Fro(3,2-g)(1)benzopyran-7-one,4-((3,7-dimethyl-2,6-octadienyl)oxy)-,(E)-

Synonyms:

5-Geranoxypsoralen; 5-Geranyloxypsoralen; Bergaptin

Molecular weight:

338,40 g/mol

Bergamottin, a natural furanocoumarin obtained from grapefruit juice induces chemosensitization and apoptosis through the inhibition of STAT3 signaling pathway in tumor cells. Kim SM, Lee JH, Sethi G, Kim C, Baek SH, Nam D, Chung WS, Kim SH, Shim BS, Ahn KS. Cancer Lett. 2014 Nov 1;354(1):153-63. doi: 10.1016/j.canlet.2014.08.002. Epub 2014 Aug 14. *** Bergamottin is a competitive inhibitor of CYP1A1 and is antimutagenic in the Ames test. Olguín-Reyes S, Camacho-Carranza R, Hernández-Ojeda S, Elinos-Baez M, Espinosa-Aguirre JJ. Food Chem Toxicol. 2012 Sep;50(9):3094-9. doi: 10.1016/j.fct.2012.05.058. Epub 2012 Jun 13. *** Identification of the residue in human CYP3A4 that is covalently modified by bergamottin and the reactive intermediate that contributes to the grapefruit juice effect. Lin HL, Kenaan C, Hollenberg PF.Drug Metab Dispos. 2012 May;40(5):998-1006. doi: 10.1124/dmd.112.044560. Epub 2012 Feb 16. *** Suppression of phorbol-12-myristate-13-acetate-induced tumor cell invasion by bergamottin via the inhibition of protein kinase Cdelta/p38 mitogen-activated protein kinase and JNK/nuclear factor-kappaB-dependent matrix metalloproteinase-9 expression. Hwang YP, Yun HJ, Choi JH, Kang KW, Jeong HG.Mol Nutr Food Res. 2010 Jul;54(7):977-90. doi: 10.1002/mnfr.200900283.

Plant: occurs naturally in bergamot (Citrus bergamia) and grapefruit (Citrus ×paradisi), also in other citrus fruits, but in small amounts.

  • Is a chemical compound from the group of furanocoumarins with geraniol side chain
  • Bergamottin is an inhibitor of CYP3A4 and is partly responsible for the slowed degradation of some drugs after consumption of grapefruit –> patient is often warned against grapefruit juice when taking drugs
  • Bergamottin increases oral bioavailability and plasma concentrations of these drugs
  • Can be isolated from grapefruit juice by extraction with ethyl acetate followed by silica gel chromatography and HPLC.
  • Example of use of this effect in topical drugs, is the concomitant use of ritonavir, a potent inhibitor of CYP3A4 and CYP2D6 isoforms of cytochrome P450, with other antiretroviral drugs

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Bergamottin

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