Xanthones from the stem bark of Garcinia nigrolineata
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 (1–18).
Section snippets
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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Flavonoids from the stems of Millettia pachyloba Drake mediate cytotoxic activity through apoptosis and autophagy in cancer cells
2019, Journal of Advanced ResearchCitation Excerpt :Compound 7 was obtained as a yellow powder, and its molecular formula was assigned as C20H18O7 from the positive ion peak at m/z 371.1137 ([M+H]+, calcd for 371.1131) in the HRESIMS, which corresponded to twelve double bond equivalents. The 1H NMR spectrum (Table 2) showed similar signals to nigrolineaxanthone F [21]: two aromatic protons [δH 6.40 (1H, s) and 7.47 (1H, s)] and dimethylchromene protons [δH 5.60 (1H, d, J = 10.0 Hz), 6.73 (1H, d, J = 10.0 Hz) and 1.48 (6H, s)]. These protons were located at the same positions as nigrolineaxanthone F according to their HMBC correlations.
A depsidone and six triterpenoids from the bark of Garcinia celebica
2016, Tetrahedron LettersCitation Excerpt :The six triterpenoids consisted of two lanostanes, (E)-3β,9α-dihydroxylanosta-24-en-26-oic acid (2) and 3,23-dioxo-9,16-lanostadien-26-oic acid (3), and four friedolanostanes, (24E)-3-oxo-17,14-friedolanosta-8,14,24-trien-26-oic acid (4), (22Z,24E)-9α-hydroxy-3-oxo-17,13-friedolanosta-12,22,24-trien-26-oic acid (5), (22Z,24E)-3-oxo-17,14-friedolanosta-8,14,22,24-tetraen-26-oic acid (6) and (22Z,24E)-9α-hydroxy-3-oxo-13α,30-cyclo-17,13-friedolanosta-22,24-dien-26-oic acid (7) (Fig. 1). Moreover, twelve known compounds were obtained: macluraxanthone (8),5 toxyloxanthone B (9),6 nigrolineaxanthone A (10),7 nigrolineaxanthone E (11),7 6-deoxyjacareubin (12),8 6-deoxyisojacareubin (13),9 morusignin A (14),10 isocudraniaxanthone B (15),11 mangiferolic acid (16),12 (22Z,24E)-9α-hydroxy-3-oxo-17,14-friedolanosta-14,22,24-trien-26-oic acid (17),13 (24E)-3β-acetoxy-9α-hydroxy-17,14-friedolanosta-14,24-dien-26-oic acid (18),14 and (22Z,24E)-3β-acetoxy-9α-hydroxy-17,14-friedolanosta-14,22,24-trien-26-oic acid (19)13 (ESI). Compound 1 was obtained as a yellow gum, giving a positive test with ethanolic ferric chloride.
New depsidones and xanthone from the roots of Garcinia schomburgkiana
2016, FitoterapiaCitation Excerpt :The 50% inhibition concentration (IC50 value) was determined by curve fitting. Phytochemical investigation of the CH2Cl2 extract from the roots of G. schomburgkiana led to the isolation of two new depsidones, schomburgdepsidones A and B (1 and 2), and one new xanthone, schomburgxanthone A (3), along with eight known compounds; oliveridepsidone A (4) [13], oliveridepsidone D (5) [13], 1,5-dihydroxyxanthone (6) [14], nigrolineaxanthone E (7) [15], 6-desoxyjacareubin (8) [16], aucuparin (9) [17], 3-hydroxy-5-methoxybiphenyl (10) [18] and methyl-2,6-dihydroxy-4-methoxy-3(3′-methyl-2′-butenyl)-benzoate (11) [19]. The structures of the three new isolated compounds were elucidated by using 1D- and 2D-NMR spectroscopy.
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Present address: Department of Chemistry, Faculty of Science, Chiang Mai University, Chaing Mai, 50200, Thailand.