Triterpenoid saponins from Sesbania vesicaria

doi:10.1016/j.phytol.2012.11.003

Phytochemistry Letters

Volume 6, Issue 1, February 2013, Pages 106-109

https://doi.org/10.1016/j.phytol.2012.11.003 Get rights and content

Abstract

Nine oleanane saponins including three new and six known were isolated from the seeds of Sesbania vesicaria. The new saponins were established as 3-O-[α-l-rhamnopyranosyl-(1 → 3)]-β-d-glucuronopyranosyl-3β,29-dihydroxy-olean-12-en-28-oic acid, 3-O-α-l-rhamnopyranosyl-28-O-β-d-glucopyransoyl-3β-hydroxy-olean-12-en-23-al-28-oate, and 3-O-α-l-rhamnopyranosyl-28-O-β-d-glucopyransoyl-3β,23-dihydroxy-olean-12-en-28-oate. All isolated saponins were assayed for their DNA topoisomerase I inhibition ability and cytotoxicity against A549 human lung adenocarcinoma epithelial cells with no positive activity detected (IC₅₀ > 312 μM and GI₅₀ > 25 μM, respectively).

Graphical abstract

Highlights

► Nine oleanane saponins were isolated from the seeds of Sesbania vesicaria. ► Three of the nine saponins are new compounds. ► The saponins were negative in DNA topoisomerase I inhibition and cytotoxicity assays.

Introduction

The genus Sesbania Scop. of the family Fabaceae consists of about 60 species widely distributed in tropical and subtropical regions of the world (Joshi-Saha and Gopalakrishna, 2007, Williams, 1983). In Asia and Africa, several Sesbania species are extensively utilized as forage and manure in their agroforestry systems (Gutteridge, 1998, Onim and Dzowela, 1988, Rinaudo et al., 1983). Some folk medicinal uses such as astringent, antihelminthic, contraceptive and arborifacient, have also been reported in the area (Onim and Dzowela, 1988). In the United States, Sesbania vesicaria (Jacq.) Elliott, Sesbania punicea (Cav.) Benth., Sesbania drummondii (Rydb.) Cory, and Sesbania herbacea (Mill.) McVaugh are widely distributed in the Southern Atlantic and Gulf Coastal plains as weeds and have long been known to be toxic to livestock and birds. Sesbanimides were identified as the cytotoxic compounds in S. vesicaria, S. punicea, and S. drummondii (Powell, 2009, Powell et al., 1990). In addition, triterpenoid saponins (Dorsaz et al., 1988, Haraguchi et al., 2000), flavonoids (Messens et al., 1989, Saxena and Mishra, 1999), fatty acids, sterols (Kohli, 1988, Miralles et al., 1992), and inositol (Misra and Siddiqi, 2005) have been isolated from various Sesbania species. In the course of discovering triterpenoid saponins from plants as DNA topoisomerase I (Topo I) inhibitors (Wang et al., 2010, Yuan et al., 2012, Zhang and Li, 2007), we conducted phytochemical investigations on saponins of S. vesicaria. Herein we report the isolation procedure and structural elucidation of these saponins.

Section snippets

Results and discussion

Three new oleanane saponins (1–3) together with six known saponins (4–9) were isolated from the n-BuOH soluble fraction of S. vesicaria (Fig. 1). The known saponins were identified as: 3-O-β-d-glucuronopyranosyl-28-O-β-d-glucopyransoyl-3β-hydroxy-olean-12-en-23-oic acid-28-oate (4) (Borel et al., 1987), 3-O-β-d-glucuronopyranosyl-28-O-β-d-glucopyransoyl-3β-hydroxy-olean-12-en-28-oate (5) (Borel et al., 1987, Dawidar et al., 1980), 3-O-[α-l-rhamnopyranosyl-(1 → 3)]-β-d-glucuronopyranosyl-28-O-β-d

General experimental procedures

NMR experiments were performed using a JEOL ECS 400 spectrometer, with spectroscopic data referenced to the solvent used. HR-mass spectra were acquired using a MDS Sciex API QStar Pulsar mass spectrometer. Optical rotation values were measured on a JASCO P-1010 polarimeter. Octadecyl-functionalized silica gel and Diaion^® HP-20 (ODS, Aldrich) was used for open column chromatography. HPLC analysis was performed on an Agilent 1260 HPLC system using Agilent ODS columns (Column A: Zorbax SB-C18, 4.6 ×

Acknowledgments

This study was funded by USDA Grants (2008-38928-19308 and 2009-38928-19744). The NMR spectral analysis was conducted using a JEOL ECS-400 NMR spectrometer purchased through the Research Development Program at Stephen F. Austin State University. The authors would like to thank Vanessa Santiago of Texas A&M University for HRESIMS analysis.

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Triterpenoid saponins from Sesbania vesicaria

Abstract

Graphical abstract

Highlights

Introduction

Section snippets

Results and discussion

General experimental procedures

Acknowledgments

Phytochemistry

Carbohydr. Res.

Phytochemistry

Soil Biol. Biochem.

Bioorg. Med. Chem. Lett.

Phytochemistry

Phytochemistry

The triterpenoid and sterol constituents of Opilia celtidifolia

Egypt. J. Chem.

Molluscicidal saponins from Sesbania sesban

Planta Med.

The perennial Sesbania species

Triterpene saponins from the leaves of Sesbania sesban

Nat. Med. (Tokyo)

The triterpenes from Stauntonia hexaphylla callus tissues and their biosynthetic significance

J. Nat. Prod.