6 ', 7'-dihydroxybergamottine

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Structural formula
Structural formula of 6 ′, 7′-dihydroxybergamottine
Simplified structural formula without stereochemistry
General
Surname 6 ', 7'-dihydroxybergamottine
Molecular formula C 21 H 24 O 6
Brief description

white solid

External identifiers / databases
CAS number 145414-76-2
PubChem 156147
Wikidata Q3599478
properties
Molar mass 372.41 g mol −1
Physical state

firmly

Melting point

105 ° C

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

6 ', 7'-Dihydroxybergamottine is a chemical compound from the group of furocoumarins with a doubly hydroxylated geraniol side chain.

Occurrence

Bergamot fruits

6 ′, 7′-dihydroxybergamottine occurs naturally in bergamot and grapefruit , and in smaller quantities in other citrus fruits .

properties

Like bergamottine , 6 ′, 7′-dihydroxybergamottine is an inhibitor of CYP3A4 and is partly responsible for the slower breakdown of some drugs after consuming grapefruit. Ingestion of 6 ′, 7′-dihydroxybergamottine increases the oral bioavailability and plasma concentration of these drugs. The IC 50 of 6 ′, 7′-dihydroxybergamottine in CYP3A4 is less than 1.2 μM . The IC 50 for 6 ′, 7′-dihydroxybergamottine in CYP1B1 is 7.17 μM. The IC 50 for 6 ′, 7′-dihydroxybergamottine in the biosynthesis of 6 β -hydroxytestosterone is 25 μM.

Bergamottin, by extraction with ethyl acetate from the juice of grapefruit, followed by silica gel - chromatography and HPLC are isolated, or by extraction with methylene chloride followed by HPLC. Bergamottine is detected by HPLC with a UV detector or by mass spectrometry . The biosynthesis takes place from bergamot via epoxy bergamot as an intermediate stage.

Individual evidence

  1. ↑ a b c d data sheet 6 ′, 7′-dihydroxybergamottine from Sigma-Aldrich , accessed on June 13, 2018 ( PDF ).
  2. ^ DG Bailey, J. Malcolm, O. Arnold, JD Spence: Grapefruit juice-drug interactions. In: British journal of clinical pharmacology. Volume 46, Number 2, August 1998, pp. 101-110, PMID 9723817 , PMC 1873672 (free full text).
  3. ↑ MF Paine, WW Widmer, HL Hart, SN Pusek, KL Beavers, AB Criss, SS Brown, BF Thomas, PB Watkins: A furanocoumarin-free grapefruit juice establishes furanocoumarins as the mediators of the grapefruit juice-felodipine interaction. In: The American journal of clinical nutrition. Volume 83, Number 5, May 2006, pp. 1097-1105, doi : 10.1093 / ajcn / 83.5.1097 , PMID 16685052 .
  4. ↑ a b c B. Girennavar, SM Poulose, GK Jayaprakasha, NG Bhat, BS Patil: Furocoumarins from grapefruit juice and their effect on human CYP 3A4 and CYP 1B1 isoenzymes. In: Bioorganic & medicinal chemistry. Volume 14, Number 8, April 2006, pp. 2606-2612, doi : 10.1016 / j.bmc.2005.11.039 , PMID 16338240 .
  5. ↑ a b D. J. Edwards, FH Bellevue, PM Woster: Identification of 6 ′, 7′-dihydroxybergamottine, a cytochrome P450 inhibitor, in grapefruit juice. In: Drug metabolism and disposition: the biological fate of chemicals. Volume 24, Number 12, December 1996, pp. 1287-1290, PMID 8971132 .
  6. ^ A b W. L. Hung, JH Suh, Y. Wang: Chemistry and health effects of furanocoumarins in grapefruit. In: Journal of food and drug analysis. Volume 25, number 1, January 2017, pp. 71-83, doi : 10.1016 / j.jfda.2016.11.008 , PMID 28911545 .