Elsevier

Phytochemistry Letters

Volume 2, Issue 3, 24 August 2009, Pages 106-109
Phytochemistry Letters

Bioactive chemical constituents of Caesalpinia bonduc (Fabaceae)

https://doi.org/10.1016/j.phytol.2009.02.002Get rights and content

Abstract

Phytochemical studies on the ethanolic extracts of Caesalpinia bonduc (Fabaceae) yielded two new homoisoflavonoids, caesalpinianone, and 6-O-methylcaesalpinianone along with five known natural products, namely, hematoxylol, stereochenol A, 6′-O-acetylloganic acid, 4′-O-acetylloganic acid, and 2-O-β-d-glucosyloxy-4-methoxybenzenepropanoic acid. Structures of these compounds were elucidated with the aid of extensive NMR spectral studies. All of these compounds exhibited different levels of glutathione S-transferase (GST) inhibitory and antifungal activities.

Graphical abstract

From the bark of Caesalpinia bonduc, two new homoisoflavonoids, namely, caesalpinianone and 6-O-methylcaesalpinianone along with five known natural products, hematoxylol, stereochenol A, 6′-O-acetylloganic acid, 4′-O-acetylloganic acid, and 2-O-β-d-glucosyloxy-4-methoxybenzenepropanoic acid, were isolated. All of these new and known natural products exhibited different levels of glutathione S-transferase (GST) inhibitory and antifungal activities.

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Introduction

Caesalpinia bonduc L. (synonymous name: C. bonducella; Family: Fabaceae), a medicinally important plant, is abundant in the tropical and subtropical regions of Asia, and the Caribbean (Chakrabarti et al., 2003, Kinoshita, 2000). The crude extracts of this plant find extensive use in folk medicines. For instance, the aqueous and ethanolic extracts of its seeds have been reported to possess in vivo hyperglycemic effect in alloxan and streptozitocin-induced type 2 diabetes in a rat model at a dose of 25 mg/kg body weight (Chakrabarti et al., 2003). The methanolic, ethyl acetate and water fractions of crude extracts exhibit in vitro activity against the growth of an array of pathogenic bacteria and fungi (Simin et al., 2001). Previous chemical studies on C. bonduc have resulted in the isolation of cassane furanoditerpenes and flavonoids (Godoy et al., 1989, Pascoe et al., 1986, Peter et al., 1997, Peter et al., 1998). Our investigations on the methanolic extract of C. bonduc afforded two new homoisoflavonoids, caesalpinianone (1, Fig. 1) and 6-O-methylcaesalpinianone (2, Fig. 1) along with five known natural products, namely, hematoxylol, stereochenol A, 6′-O-acetylloganic acid, 4′-O-acetylloganic acid, and 2-O-β-d-glucosyloxy-4-methoxybenzenepropanoic acid. These compounds were identified with the aid of NMR and mass spectral studies. As part of our ongoing efforts in discovering new naturally occurring GST inhibitors (Ata and Udenigwe, 2008, Ata et al., 2007), and antifungal compounds (Ata et al., 2006), we describe the anti-GST and antifungal properties of these compounds.

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Results and discussion

Caesalpinianone (1) was isolated as a colorless amorphous solid. Its IR spectrum displayed intense absorption bands at 3394 (OH), 1641 (Cdouble bondO) and 1612 (Cdouble bondC) cm−1. The HR-EI-MS showed a molecular ion peak at m/z 302.0788, which was in agreement with the molecular formula C16H14O6 (calcd 302.0790) and suggested the presence of ten degrees of unsaturation in compound 1. Six degrees of unsaturation were accounted for the presence of a 4-chromanone moiety and the remaining four double bond equivalents

General

The 1H NMR spectra were recorded in CD3OD on a 300 JEOL NMR spectrometers at 300 MHz, while the 13C NMR spectra were recorded on same instrument at 75 MHz with TMS as an internal standard. The IR spectra were recorded on a Jasco-IRA1 IR spectrophotometer. Mass spectrometric measurements were conducted on a Bruker MicroTOF II and Hewlett-Packard 5989B MS. The UV spectral data were acquired on a Shimadzu UV 240 instrument. The optical rotations were measured on a Polatronic D polarimeter (Hitachi)

Acknowledgment

We are grateful to Natural Sciences and Engineering Research Council of Canada (NSERC) for providing funding for this research.

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