6',7'-Dihydroxybergamottin

6',7'-Dihydroxybergamottin
Names
IUPAC name
4-[(E,6R)-6,7-dihydroxy-3,7-dimethyloct-2-enoxy]furo[3,2-g]chromen-7-one
Identifiers
3D model (JSmol)
ChemSpider
KEGG
UNII
  • InChI=1S/C21H24O6/c1-13(4-6-18(22)21(2,3)24)8-10-26-20-14-5-7-19(23)27-17(14)12-16-15(20)9-11-25-16/h5,7-9,11-12,18,22,24H,4,6,10H2,1-3H3/b13-8+
    Key: IXZUPBUEKFXTSD-MDWZMJQESA-N
  • O=C\1Oc3c(/C=C/1)c(OC\C=C(/C)CCC(O)C(O)(C)C)c2ccoc2c3
Properties
C21H24O6
Molar mass 372.417 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

6',7'-Dihydroxybergamottin is a natural furanocoumarin found in pomelos, grapefruits, and sour oranges,[1] in both the peel and the pulp. Along with the chemically related compound bergamottin, it is believed to be responsible for a number of grapefruit–drug interactions, in which the consumption of citrus containing one or both of these compounds (especially grapefruit) affects the metabolism of a variety of pharmaceutical drugs.[2][3][4]

References

  1. ^ Dugrand-Judek, Audray; Olry, Alexandre; Hehn, Alain; Costantino, Gilles; Ollitrault, Patrick; Froelicher, Yann; Bourgaud, Frédéric (November 2015). "The Distribution of Coumarins and Furanocoumarins in Citrus Species Closely Matches Citrus Phylogeny and Reflects the Organization of Biosynthetic Pathways". PLOS ONE. 10 (11): e0142757. Bibcode:2015PLoSO..1042757D. doi:10.1371/journal.pone.0142757. PMC 4641707. PMID 26558757.
  2. ^ Edwards, D. J.; Bellevue, F. H.; Woster, P. M. (December 1996). "Identification of 6',7'-dihydroxybergamottin, a cytochrome P450 inhibitor, in grapefruit juice". Drug Metabolism and Disposition. 24 (12): 1287–1290. PMID 8971132.
  3. ^ Bailey, David G.; Malcolm, J.; Arnold, O.; Spence, J. David (1998). "Grapefruit juice-drug interactions". Br J Clin Pharmacol. 46 (2): 101–110. doi:10.1046/j.1365-2125.1998.00764.x. PMC 1873672. PMID 9723817.
  4. ^ Girennavar, Basavaraj; Poulose, Shibu M.; Jayaprakasha, Guddadarangavvanahally K.; Bhat, Narayan G.; Patil, Bhimanagouda S. (2006). "Furocoumarins from grapefruit juice and their effect on human CYP 3A4 and CYP 1B1 isoenzymes". Bioorganic & Medicinal Chemistry. 14 (8): 2606–2612. doi:10.1016/j.bmc.2005.11.039. ISSN 0968-0896. PMID 16338240.