6',7'-DIHYDROXYBERGAMOTTIN Chemical Properties

Melting point:

112-113 °C

Boiling point:

578.2±50.0 °C(Predicted)

Density 

1.260

storage temp. 

2-8°C

solubility 

ethanol: soluble

pka

14.65±0.29(Predicted)

form 

Solid

color 

white to off-white

Safety Information

WGK Germany 

3

6',7'-DIHYDROXYBERGAMOTTIN Usage And Synthesis

Description

6,7-dihydroxy Bergamottin (6,7-DHB) is a potent inhibitor of CYP3A4 (IC₅₀ = 25 μM). It appears to be the primary compound in grapefruit juice that is responsible for inhibition of testosterone 6β-hydrolase activity. Ingestion of grapefruit juice during treatment regimes with drugs normally metabolized by cytochrome P450 enzymes of the CYP3A subfamily results in a substantial increase in plasma concentration of these agents. However, giving a patient grapefruit juice or just 6,7-DHB could be advantageous in cases where a drug is metabolized too quickly by CYP3A4.

Uses

6′,7′-dihydroxybergamottin has been used to study its effect on the inhibition of cytochrome P450 (CYP)-mediated triazolam hydroxylation in dog liver microsomes.

Uses

A minor metabolite of Bergamottin. Metabolization of Bergamottin by cytochromes P 450 2B6 and 3A5.

Uses

A minor metabolite of Bergamottin (B318400). Metabolization of Bergamottin by cytochromes P 450 2B6 and 3A5.

Definition

ChEBI: 6',7'-Dihydroxybergamottin is a member of psoralens.

Biochem/physiol Actions

CYP3A4 inhibitor.

in vitro

6,7-dhb significantly blocked the testosterone 6β-hydrolase in human liver microsomes and human cyp3a4 expressed in escherichia coli membrane in a time- and concentration-dependent manner. furthermore, 6,7-dhb proved to be a potent nadph- and time-dependent inhibitor of cyp3a4 [1]. 6,7-dhb concentration-dependently inhibited nifedipine (nfp) oxidation in hepg2-gs-3a4 cell, a cell line from hepatoblastoma with overexpression of human cyp3a4 [2].

in vivo

male wistar-st rats were intraduodenally administered with 6,7-dhb at a dose of 3.4 mg/ml. after 4 hours, 6,7-dhb had no significant effects on the nfp plasma concentrations, suggesting that 6,7-dhb had no pharmacokinetic effect on the rats [3].

IC 50

25 μm

References

[1]. bellevue, f., woster, p., edwards, d., he, k., & hollenberg, p. synthesis and biological evaluation of 6′,7′-dihydroxybergamottin (6,7-dhb), a naturally occurring inhibitor of cytochrome p450 3a4. bioorganic & medicinal chemistry letters. 1997; 7(20): 2593-2598.
[2]. araki, n., tsuruoka, s., hasegawa, g., yanagihara, h., omasa, t., & enosawa, s. et al. inhibition of cyp3a4 by 6′,7′-dihydroxybergamottin in human cyp3a4 over-expressed hepg2 cells. journal of pharmacy and pharmacology. 2012; 64(12): 1715-1721.
[3]. mohri, k., & uesawa, y. effects of furanocoumarin derivatives in grapefruit juice on nifedipine pharmacokinetics in rats. pharmaceutical research, 2001;18(2):177-182.

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