New coumarins from Clausena lansium twigs

Wisanu Maneerat,Surat Laphookhieo,Nisakorn Saewan,Uma Prawat

doi:10.1590/s0103-50532010000400012

Wisanu Maneerat, Surat Laphookhieo + Show 2 more

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https://doi.org/10.1590/s0103-50532010000400012

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Abstract

Two new coumarins namely Clausenalansimin A (5) and B (9) together with seven known coumarins (1-4 and 6-8), were isolated from twigs of Clausena lansium. All compounds were determined by spectroscopic methods. Some of isolates had cytotoxicity against human cancer cell lines (KB, MCF7 and NCI-H187).

Highlights

Clausena lansium (Lour.) Skeels is a distant relative of citrus fruit belonging to the Rutaceae family
The combination of CH2Cl2 and acetone extracts of twigs of C. lansium was separated by chromatographic techniques to yield two new coumarins, clausenalansimin A [5] and B [9], together with seven known compounds [1,2,3,4, 6,7,8]
The CH2Cl2 and acetone extracts were combined (34.02 g) and subjected to Quick column chromatography (QCC) over silica gel eluted with a gradient of hexane-acetone (100% hexane to 100% acetone) to provide seventeen fractions (A-Q)

Summary

Introduction

Clausena lansium (Lour.) Skeels is a distant relative of citrus fruit belonging to the Rutaceae family. The combination of CH2Cl2 and acetone extracts of twigs of C. lansium was separated by chromatographic techniques to yield two new coumarins, clausenalansimin A [5] and B [9], together with seven known compounds [1,2,3,4, 6,7,8]. The 1H NMR spectrum showed signals of -OCH2-CH=C- unit at d 4.66 (2H, m, H-1′′) and 5.53 (1H, t, J 5.6 Hz, H-2′′) and an a,b-unsaturated g-lactone moiety at d 2.35 (1H, dd, J 17.0, 7.2 Hz, H-4a′′), 2.61 (1H, dd, J 17.0, 5.2 Hz, H-4b′′), 5.11 (1H, m, H-5′′), 7.09 (1H, br t, H-6′′), 1.92 (3H, br s, H-8′′).10 The side chain unit was supported by COSY and HMBC experiments (Figure 2) and located at C-5 due to the 2J

Results

Conclusion