Chalepin and Chalepensin: Occurrence, Biosynthesis and Therapeutic Potential.

Shaymaa Al-Majmaie,Azhar Rasul,Satyajit D. Sarker,Afaf Al-Groshi,Lutfun Nahar

doi:10.3390/molecules26061609

Abstract

Dihydrofuranocoumarin, chalepin (1) and furanocoumarin, chalepensin (2) are 3-prenylated bioactive coumarins, first isolated from the well-known medicinal plant Ruta chalepensis L. (Fam: Rutaceae) but also distributed in various species of the genera Boenminghausenia, Clausena and Ruta. The distribution of these compounds appears to be restricted to the plants of the family Rutaceae. To date, there have been a considerable number of bioactivity studies performed on coumarins 1 and 2, which include their anticancer, antidiabetic, antifertility, antimicrobial, antiplatelet aggregation, antiprotozoal, antiviral and calcium antagonistic properties. This review article presents a critical appraisal of publications on bioactivity of these 3-prenylated coumarins in the light of their feasibility as novel therapeutic agents and investigate their natural distribution in the plant kingdom, as well as a plausible biosynthetic route.

Highlights

The distribution of these compounds appears to be restricted to the plants of the family Rutaceae
(1), known as heliettin, is optically active, chalepensin (2), known as xylotenin, does not possess any optical activity. These coumarins are rather rare in the sense that there are not many 3-prenylated naturally occurring furanocoumarins reported to date, there are quite a good number of bioactivity studies carried out on these compounds
The biosynthesis of chalepin (1) and chalepensin (2) begins from the simple coumarin umbelliferone, which is formed from the amino acid

Summary

Introduction

Chalepin (1; mol formula: C19 H22 O4 ; mol weight 314) and chalepensin (2; mol formula: C16 H14 O3 ; mol weight 254) (Figure 1) are, respectively, a dihydrofuranocoumarin and a furanocoumarin, with a prenylation at C-3 of the coumarin core structure. These coumarins, as the names imply, were first isolated from Ruta chalepensis L. While chalepin (1), known as heliettin, is optically active, chalepensin (2), known as xylotenin, does not possess any optical activity These coumarins are rather rare in the sense that there are not many 3-prenylated naturally occurring furanocoumarins reported to date, there are quite a good number of bioactivity studies carried out on these compounds.

Distribution

Biosynthesis

Antidiabetic Activity

Antifertility Activity

Antimicrobial Property

Antiprotozoal Activity

Antiviral Activity

Miscellaneous Activities

Mutagenicity and Other Toxicities

Findings

Conclusions