Bergaptol

Bergaptol
Names
Preferred IUPAC name
4-Hydroxy-7H-furo[3,2-g] [1]benzopyran-7-one
Other names
5-Hydroxypsoralen, 5-Hydroxyfuranocoumarin
Identifiers
CAS Number
  • 486-60-2 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 4444066
ECHA InfoCard 100.230.572 Edit this at Wikidata
PubChem CID
  • 5280371
UNII
  • KTC8ANI30F checkY
CompTox Dashboard (EPA)
  • DTXSID40197564 Edit this at Wikidata
InChI
  • InChI=1S/C11H6O4/c12-10-2-1-6-9(15-10)5-8-7(11(6)13)3-4-14-8/h1-5,13H
    Key: GIJHDGJRTUSBJR-UHFFFAOYSA-N
  • O=C\1Oc3c(/C=C/1)c(O)c2ccoc2c3
Properties
Chemical formula
 C11H6O4
Molar mass 202.165 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

Bergaptol is a natural furanocoumarin with the molecular formula C11H6O4. It is found in the essential oils of citrus including lemon and bergamot.[1]

Research

Bergaptol is researched for anti-inflammatory, antioxidant, anti-cancer, anti-osteoporosis, anti-microbial, and anti-lipidemic properties.[2]

Bergaptol inhibits cytochrome P450 enzymes (CYP), particularly CYP2C9 and CYP3A4. This inhibition can impact the metabolism and concentrations of various drugs and toxins within the body. When compared to other coumarins, bergaptol demonstrates the lowest potency in inhibiting CYP3A4 specifically in cancer cells. Instead, it has the ability to suppress drug efflux transporters, such as P-glycoprotein, which can help overcome chemotherapeutic drug resistance.[2]

Bergaptol exhibits strong antimicrobial effects and has a high potential for inhibiting quorum sensing, a process crucial for microbial communication and virulence.[2]

In vivo studies have shown that bergaptol has a longer retention time in plasma compared to other coumarins.[2]

Toxicity of bergaptol in humans has not been extensively studied and remains unclear.[2]

Notes

  1. ^ Stanley WL, Vannier SH (1957). "Chemical Composition of Lemon Oil. I. Isolation of a Series of Substituted Coumarins". Journal of the American Chemical Society. 79 (13): 3488–3491. doi:10.1021/ja01570a049. ISSN 0002-7863.
  2. ^ a b c d e Phucharoenrak P, Trachootham D (February 2024). "Bergaptol, a Major Furocoumarin in Citrus: Pharmacological Properties and Toxicity". Molecules. 29 (3): 713. doi:10.3390/molecules29030713. PMC 10856120. PMID 38338457.