Antifungal activity of anthraquinone derivatives from Rheum emodi

doi:10.1016/S0378-8741(00)00195-1

Journal of Ethnopharmacology

Volume 72, Issues 1–2, 1 September 2000, Pages 43-46

https://doi.org/10.1016/S0378-8741(00)00195-1 Get rights and content

Abstract

Rhein, physcion, aloe-emodin and chrysophanol isolated from Rheum emodi rhizomes exhibited antifungal activity against Candida albicans, Cryptococcus neoformans, Trichophyton mentagrophytes and Aspergillus fumigatus (MIC 25–250 μg/ml).

Introduction

Rheum emodi (Polygonaceae), commonly known as revand-chini, is the Himalayan species of Indian rhubarb found wild at an altitude of 4000–12 000 feet in Kashmir, Nepal, Sikkim and Bhutan. Rhubarb has been successfully grown in certain parts of Assam (Nadkarni, 1954). Roots of the Indian rhubarb is darker, inferior in aroma, is a well known stomachic, bitter and cathartic, and used all over the world (Thakur et al., 1989).

There have already been many reports about antibacterial and antifungal activities of the anthraquinones, the napthoquinones isolated from natural sources (Agarwal et al., 1976, Fuzellier et al., 1982, Inamori et al., 1983, Cyong et al., 1987, Harvey and Waring, 1987). In addition several other biological activities such as laxative, diuretic, and in vivo inhibitory effect towards P388 leukemia in mice are also reported (Lu and Chen, 1989, Oshio and Kawamura, 1985, Zhou and Chen, 1988).

The present communication deals with naturally occurring antifungal principles from R. emodi rhizomes. A bioassay guided isolation, characterisation and evaluation of their methanolic extracts exhibited antifungal activities which resulted in four anthraquinone derivatives (1–4) as active components.

Section snippets

Plant material

The rhizomes of Rheum emodi were purchased from a local market and identified by Dr S.P. Jain, Botany Department of CIMAP, Lucknow, India, where a voucher specimen has been deposited.

Analytical material and methods

Column chromatography was carried out using silica gel 60–120 mesh (Ranbaxy) and TLC silica gel G (Ranbaxy). IR spectra were recorded with KBr pellets on a Perkin-Elmer 1710 FT-IR spectrophotometer. ¹H NMR spectra were obtained on a Bruker DRX (200 MHz) instrument with TMS as internal standard while EI-MS was

Results

The antifungal screening of crude MeOH extract and anthraquinone derivatives (1–4) showed the MIC to be 25–250 μg/ml. The pure compounds were more active than the crude extract (see Table 1).

Discussion

The dark brown methanolic extract of R. emodi rhizomes was subjected to column chromatography. The methanolic extract exhibited potent antifungal activities in our primary screening programme. Chromatographic purification of the methanol extract on silica gel produced rhein (1), physcion (2), aloe-emodin (3) and chrysophanol (4). Their identities were established by comparing the m.p., IR, ¹H NMR and MS data with that of the known compounds.

The antifungal screening of crude MeOH extract (MIC

Acknowledgements

The authors are grateful to the Head, RSIC, at CDRI, Lucknow, for obtaining the spectral data.

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Location of glycosylation and alkylation sites in anthraquinones by ¹H NMR
Phytochemistry
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In vitro toxicity of constituents of Rumex maritimus Linn. to ring worm fungi
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N.R. Ayyangar et al.
Anthraquinones and anthrone series: Part XXVI — a new synthesis of chrysophanol, rhein, islandicin, emodin and physcion
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Antibacteriosides Fragilus substance from rhubarb
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Antifungal activity of Cassia alata L.
Annals of Pharmacology, France
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Antifungal and other compounds isolated from the roots of New Zealand flax plants (The genus Phormium)
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Biochemical study of Chinese rhubarb. XXIX. Inhibitory effects of anthraquinone on P388 leukemia in mice
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There are more references available in the full text version of this article.

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Journal of Ethnopharmacology

Abstract

Introduction

Section snippets

Plant material

Analytical material and methods

Results

Discussion

Acknowledgements

References (16)

Location of glycosylation and alkylation sites in anthraquinones by ¹H NMR

Phytochemistry

In vitro toxicity of constituents of Rumex maritimus Linn. to ring worm fungi

Current Science

Anthraquinones and anthrone series: Part XXVI — a new synthesis of chrysophanol, rhein, islandicin, emodin and physcion

Journal of Scientific and Industrial Research

Antibacteriosides Fragilus substance from rhubarb

Journal of Ethnopharmacology

Antifungal activity of Cassia alata L.

Annals of Pharmacology, France

Antifungal and other compounds isolated from the roots of New Zealand flax plants (The genus Phormium)

Journal of Natural Products

Studies on metabolites produced by Aspergillus terreus var. aureus. I. Chemical structures and antimicrobial activities of metabolites isolated from culture broth

Chemical and Pharmaceutical Bulletin

Biochemical study of Chinese rhubarb. XXIX. Inhibitory effects of anthraquinone on P388 leukemia in mice

Journal of the China Pharmacology University

Cited by (337)

The impact of π-π stacking interactions on photo-physical properties of hydroxyanthraquinones

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Physcion prevents high-fat diet-induced endothelial dysfunction by inhibiting oxidative stress and endoplasmic reticulum stress pathways

A systematic review of pharmacological potential of phytochemicals from Rumex abyssinicus Jacq

Isolation and characterization of natural dyes and pigments

The isomers, aloe-emodin and emodin, possess differential inhibitory activities against CYP1B1 enzyme