Elsevier

Phytochemistry

Volume 64, Issue 6, November 2003, Pages 1149-1156
Phytochemistry

Xanthones from the stem bark of Garcinia nigrolineata

https://doi.org/10.1016/S0031-9422(03)00502-8Get rights and content

Abstract

Nine xanthones, nigrolineaxanthones A–I, together with nine known xanthones, were isolated from the crude methanol extract of the stem bark of Garcinia nigrolineata; two of which have previously been reported as synthetic xanthones. The structures were elucidated by analysis of spectroscopic data, especially using 1D and 2D NMR spectroscopic data.

Nine xanthones, nigrolineaxanthones A-1, together with nine known xanthones, were isoloated from the crude methanol extract of the stem bark of Garcinia nigrolineata. The structures were elucidated by analysis of the spectroscopic data, especially using 1D and 2D NMR data.

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Introduction

In our continuing phytochemical investigation of Garcinia plants (Guttiferae family) found in Southern Thailand, we have examined the stem bark of Garcinia nigrolineata. This investigation has led to the isolation and structural determination of nine new and nine known xanthones (118).

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Results and discussion

The MeOH extract of the stem bark of G. nigrolineata was subjected to chromatographic purification to afford nine new xanthones: five trioxygenated (1, 3, 4, 6 and 8) and four tetraoxygenated (2, 5, 7 and 9) xanthones, along with nine known xanthones: six trioxygenated ones: 1,3,5-trihydroxy-4-(3-hydroxy-3-methylbutyl)xanthone (10) (Gonda et al., 2000), 1,3,7-trihydroxy-2-(3-hydroxy-3-methylbutyl)xanthone (12) (Garcia Cortez et al., 1998), 6-deoxyjacreubin (13) (Owen and Scheinmann, 1974),

General

Melting points were determined on an Electrothermal 9100 melting point apparatus and are uncorrected. IR spectra were obtained either on a FTS 165 FT-IR spectometer or a Perkin-Elmer Spectrum GX FT-IR system. 1H and 13C NMR spectra were recorded on a Varian UNITY INOVA 500 MHz or a Brüker AMX 400 MHz spectrometer using deuterochloroform solutions unless otherwise stated with TMS as internal standard. UV spectra were measured with a Specord S100 spectrophotometer (Analytik Jena Ag). Optical

Acknowledgements

T.R. thanks Higher Education Development Project: Postgraduate Education and Research Program in Chemistry, funded by the Royal Thai Government (PERCH) for a scholarship and the Graduate School, Prince of Songkla University for material support.

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Present address: Department of Chemistry, Faculty of Science, Chiang Mai University, Chaing Mai, 50200, Thailand.

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