Isolation, Characterisation and Antifungal Activity of β-Lapachone from Tecomaria capensis (Thunb.) Spach Leaves

Karthikeyan R,Sai Koushik O

doi:10.4172/2167-0412.1000239

Abstract

β-Lapachone (3, 4-dihydro-2,2-dimethyl-2H-naphthol [1,2-b] pyran-5,6-dione), was originally isolated from the lapacho tree (Tabebuia avellanedae) of South America. It is a lipophilic ortho-naphthoquinone. β-Lapachone has antimicrobial, antifungal, antiviral antitumor and anti-trypanosomal activities. In a number of tumors (e.g., breast, colon, lung, and pancreatic cancers) with high NAD (P) H expression levels of: quinone oxidoreductase (NQO1), β-lapachone activates a novel apoptotic response. β-Lapachoneis a major constituent of the species Tecomaria capensis (Thunb.) Spach. On silica gel GF254 TLC plates and the chromate plate analytical thin layer chromatography was accomplished. It was developed withToluene: Ethyl acetate (7:3 v/v) as mobile phase. In this study isolation of β-Lapachone was achieved by preparative TLC. The compound thus isolated was characterised by Mass, H1 NMR and FT-IR spectral analysis. Mass spectral data shows molecular ion peak of m/z=242. Antifungal activity was measured against Candida albicans and Aspergillus nigrus fromethyl acetate extracts of selected species.

Highlights

Naphthoquinones display very substantial pharmacological properties; like antipyretic, antibacterial, antifungal, insecticidal, antiinflammatory and antiviral properties
Beta-lapachone can be synthesized by chemical transformation of lapachol, extracted from the bark of plants of the Bignoniaceae family or from lomatiol, isolated from seeds of lomatia [6]. it is reported to present a significant anti-neoplastic activity against human cancer cell lines originating from leukemia [7], prostate [8], malignant glioma [9], hepatoma [10], colon [11,12], breast [13], ovarian [14], pancreatic [15,16] tumors, at concentrations in the range of 1-10 μM (IC50)
Complete extraction of β-Lapachone was achieved by successive solvent extraction with ethyl acetate

Summary

Introduction

Naphthoquinones display very substantial pharmacological properties; like antipyretic, antibacterial, antifungal, insecticidal, antiinflammatory and antiviral properties. Other studies have shown that in combination with taxol, beta-lapachone is an effective agent against human ovarian and prostate xenografts in mice. This naphthoquinone was reported to have, anti-Trypanosoma properties [17,18,19]. Previous studies showing antifungal activity of lapachol and beta-lapachone against C. neoformans are to some extent contradictory because of the different experimental protocols used [20]. These data indicate that new studies are necessary before proposing antifungal tests on humans. Further the study deals with characterisation of β-lapachone in the sample extract by Mass and H1 NMR and FT-IR spectral analysis for structure identification

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Conclusion