Coumarins and xanthones from the seeds of Mammea siamensis

Abstract

Uma cumarina inédita, mammea E/BB ciclo D (1), juntamente com cinco compostos conhecidos, mammea E/BA ciclo D (2), suragina C (3), terapina B (4), 1,7-dihidroxixantona (5) e 1-hidróxi-5-metoxyxantona (6), foram isolados de sementes de Mammea siamensis. Suas estruturas foram caracterizadas usando dados de RMN 1D e 2D. Suragina C e terapina B mostraram atividade citotóxica contra adenocarcinoma de mama (MCF-7), câncer cervical humano (HeLa), câncer de colon (HT-29) e câncer oral humano (KB). A new coumarin, mammea E/BB cyclo D (1), together with five known compounds, mammea E/BA cyclo D (2), suragin C (3), therapin B (4), 1,7-dihydroxyxanthone (5) and 1-hydroxy-5methoxyxanthone (6), were isolated from the seeds of Mammea siamensis. Their structures were characterized using 1D and 2D NMR spectral data. Suragin C and therapin B showed cytotoxic activity against breast adenocarcinoma (MCF-7), human cervical cancer (HeLa), colon cancer (HT-29) and human oral cancer (KB).

Cytotoxic Coumarins from the Bark of Mammea siamensis

“…However, compound 2 with a geranyl group exhibited much stronger inhibitory effect compared with 3 which possessed a prenyl group. Although the latter result was consistent with previous results by Laphookhieo et al 9) in which effect of 2 and 3 against the cell number of MCF-7, HeLa, KB and HT-29 cell lines were tested. The above results therefore could not readily be explained in terms of substituted coumarin structures.…”

“…1), and four xanthones, 1,7-dihydroxyxanthone (6), 11) 7-hydroxy-1-methoxyxanthone (7), 5) 1,7-dimethoxyxanthone (8), 5) and 1,7-dimethoxy-6-hydroxyxanthone (9) 12) (Fig. 2).…”

“…Surangin D (1) C-23, C-15, C-10, C-16 9 (C, C-17, C-7, C-2, C-5, C-4, C-8a, C-14), 121.7 and 107.8 (CH, C-13, C-3), 121.0, 106.8 and 105.1 (C, C-6, C-8, C-4a), 81.9 and 47.3 (CH, C-9, C-18), 62.6 and 57.9 (CH 3 , 5-OMe, 9-OMe), 30.4 and 27.1 (CH 2 , C-10, C-19) 25.7 (CH 3 , C-16), 23.1 (CH 2 , C-12), 18.0, 16.6, 11.7 and 10.6 (CH 3 , C-15, C-21, C-20, C-11); HR-ESI-MS m/z: 417.2272 [MϩH] ϩ (Calcd for C 24 3 (C, C-17, C-7, C-2, C-5, C-4, C-8a), 132.9 (s, C-14), 121.5 and 111.2 (CH, C-13, C-…”

“…3) Earlier studies have shown that the genus is a rich source of coumarins and xanthones, some of which have potential pharmacological and therapeutic properties. [4][5][6][7][8][9] We here report the chemical constituents of the bark of Mammea siamensis collected in south Vietnam with the isolation of a new and four known coumarins as well as seven xanthones. In addition, new data on the anti-proliferative activity of the coumarins surangins C-D and theraphins B-C and their methylated derivatives were generated using sulforhodamine B (SRB) assay on four human cancer cell lines, MCF-7 (breast adenocarcinoma), HeLa, DLD-1 (colon cancer) and NCI-H460 (human lung cancer).…”

Aromatase Inhibitory Activity of Geranylated Coumarins, Mammeasins C and D, Isolated from the Flowers of <i>Mammea siamensis</i>

“…The flowers of this plant have been used for preparing a heart tonic in Thai traditional medicine ("Sarapi" in Thai). [1][2][3][4][5][6][7][8][9][10] Several coumarins, [1][2][3][4][5][6][7] xanthones, 8,9) triterpenoids, 10) and steroids 10) have been isolated from the flowers, 1,2,6,7,10) seeds, 3,9) twigs, 4,8) and bark 5) of this plant. In the course of our characterization studies on bioactive constituents in Thai natural medicine, 1,[11][12][13][14][15][16][17][18][19][20][21][22][23][24][25] we reported that the methanol extract of the flowers of M. siamensis and its coumarin constituents showed inhibitory effects on nitric oxide production in lipopolysaccharide-activated RAW264.7 cells.…”