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A new phenyl alkyl ester and a new combretin triterpene derivative from Combretum fragrans F. Hoffm (Combretaceae) and antiproliferative activity
Open Chemistry ( IF 2.3 ) Pub Date : 2020-12-31 , DOI: 10.1515/chem-2020-0167
Isaac Silvère Gade 1, 2 , Corinne Chadeneau 3 , Richard Tagne Simo 4 , Emmanuel Talla 1 , Alex De Theodore Atchade 2 , Paule Seité 3 , Brigitte Vannier 3 , Sophie Laurent 5 , Celine Henoumont 5 , Armel H. Nwabo Kamdje 4 , Jean-Marc Muller 3
Affiliation  

Abstract This work concerns the isolation and structure elucidation of compounds obtained from the extract of leaves and stem bark of Combretum fragrans F. Hoffm. Both extracts and some isolated compounds were tested for antiproliferative activity on glioblastoma (U87MG and C6 cells) and prostate (PC-3 cells) cancer cell lines using XTT (2,3-bis[2-methoxy-4-nitro-5-sulfophenyl]-2H-tetrazolium-5-carboxyanilide inner salt) assay. The dichloromethane/methanol (1:1) extract of the leaves led to the isolation of two new compounds such as fragransinate (1) and combretin C (2), alongside five known compounds such as combretin A (3), belamcanidin (4), cirsilineol (5), velutin (6), and a mixture of β-sitosterol-3-O-β-d-glucopyranoside (10a) and stigmasterol-3-O-β-d-glucopyranoside (10b), whereas the methanol extract of the stem bark led to the isolation of three known compounds betulinic acid (7), bellericagenin B (8), and a mixture of β-sitosterol (9a) and stigmasterol (9b). The structure of compounds was elucidated by nuclear magnetic resonance and mass spectrometry data. The methanol extract of the stem bark showed a powerful antiproliferative activity on all tested cells, as well as the extract of leaves which also showed important cytotoxicity effect. Compound (3) showed good antiproliferative activity particularly on U87MG and PC-3 cells, whereas compound (5) exhibits moderated activity. Compounds (2) and (8) were not active on all tested cells.

中文翻译:

来自 Combretum fragrans F. Hoffm (Combretaceae) 的一种新的苯基烷基酯和一种新的 Combretin 三萜衍生物和抗增殖活性

摘要 这项工作涉及从 Combretum fragrans F. Hoffm 的叶子和茎皮提取物中获得的化合物的分离和结构解析。使用 XTT(2,3-双[2-甲氧基-4-硝基-5-磺基苯基)检测提取物和一些分离的化合物对胶质母细胞瘤(U87MG 和 C6 细胞)和前列腺(PC-3 细胞)癌细胞系的抗增殖活性]-2H-四唑鎓-5-羧基苯胺内盐)测定。叶子的二氯甲烷/甲醇 (1:1) 提取物导致分离出两种新化合物,例如 fragransinate (1) 和 compretin C (2),以及五种已知化合物,例如 compretin A (3)、belamcanidin (4) , 西林醇 (5)、绒毛蛋白 (6) 以及 β-谷甾醇-3-O-β-d-吡喃葡萄糖苷 (10a) 和豆甾醇-3-O-β-d-吡喃葡萄糖苷 (10b) 的混合物,而茎皮的甲醇提取物导致分离出三种已知化合物桦木酸 (7)、bellericagenin B (8) 以及 β-谷甾醇 (9a) 和豆甾醇 (9b) 的混合物。通过核磁共振和质谱数据阐明了化合物的结构。茎皮甲醇提取物对所有测试细胞均显示出强大的抗增殖活性,叶子提取物也显示出重要的细胞毒性作用。化合物(3)表现出良好的抗增殖活性,特别是对U87MG和PC-3细胞,而化合物(5)表现出适度的活性。化合物(2)和(8)对所有测试细胞均无活性。通过核磁共振和质谱数据阐明了化合物的结构。茎皮甲醇提取物对所有测试细胞均显示出强大的抗增殖活性,叶子提取物也显示出重要的细胞毒性作用。化合物(3)表现出良好的抗增殖活性,特别是对U87MG和PC-3细胞,而化合物(5)表现出适度的活性。化合物(2)和(8)对所有测试细胞均无活性。通过核磁共振和质谱数据阐明了化合物的结构。茎皮甲醇提取物对所有测试细胞均显示出强大的抗增殖活性,叶子提取物也显示出重要的细胞毒性作用。化合物(3)表现出良好的抗增殖活性,特别是对U87MG和PC-3细胞,而化合物(5)表现出适度的活性。化合物(2)和(8)对所有测试细胞均无活性。
更新日期:2020-12-31
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