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New acyclic secondary metabolites from the biologically active fraction of Albizia lebbeck flowers

机译:Albizia lebbeck花的生物活性部分中新的无环次级代谢产物

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摘要

The total extract of Albizia lebbeck flowers was examined in vivo for its possible hepatoprotective activity in comparison with the standard drug silymarin at two doses. The higher dose expressed promising activity especially in reducing the levels of AST, ALT and bilirubin. Fractionation via liquid–liquid partition and reexamination of the fractions revealed that the n-butanol fraction was the best in improving liver biochemical parameters followed by the n-hexane fraction. However, serum lipid parameters were best improved with CHCl3 fraction. The promising biological activity results initiated an intensive chromatographic purification of A. lebbeck flowers fractions. Two compounds were identified from natural source for the first time, the acyclic farnesyl sesquiterpene glycoside1-O-[6-O-α-l-arabinopyranosyl-β-d-glucopyranoside]-(2E,6E-)-farnesol (>6) and the squalene derivative 2,3-dihydroxy-2,3-dihydrosqualene (>9), in addition to eight compounds reported here for the first time from the genus Albizia; two benzyl glycosides, benzyl 1-O-β-d-glucopyranoside (>1) and benzyl 6-O-α-l-arabinopyranosyl β-d-glucopyranoside (>2); three acyclic monoterpene glycosides, linalyl β-d-glucopyranoside (>3) and linalyl 6-O-α-l-arabinopyranosyl-β-d-glucopyranoside (>4); (2E)-3,7-dimethylocta-2,6-dienoate-6-O-α-l arabinopyranosyl-β-d-glucopyranoside (>5), two oligoglycosides, n-hexyl-α-l arabinopyranosyl-(1 → 6)-β-d-glucopyranoside (creoside) (>7) and n-octyl α-l-arabinopyranosyl-(1 → 6)-β-d-glucopyranoside (rhodiooctanoside) (>8); and ethyl fructofuranoside (>10). The structures of the isolated compounds were elucidated based on extensive examination of their spectroscopic 1D and 2D-NMR, MS, UV, and IR data. It is worth mentioning that, some of the isolated linalol glycoside derivatives were reported as aroma precursors.
机译:与标准剂量的水飞蓟素在两个剂量下相比,在体内检查了合欢属花的总提取物的可能的保肝活性。较高的剂量表现出有希望的活性,特别是在降低AST,ALT和胆红素水平方面。通过液-液分配进行分级分离和馏分的重新检测表明,正丁醇馏分在改善肝脏生化参数方面是最佳的,其次是正己烷馏分。但是,用CHCl3组分可以最好地改善血清脂质参数。有前途的生物活性结果启动了对Lebbeck花级分的强化色谱纯化。首次从天然来源中鉴定出两种化合物,即无环法呢基倍半萜烯糖苷1-O- [6-O-α-1-阿拉伯吡喃糖基-β-d-吡喃葡萄糖苷]-(2E,6E-)-法尼醇(> 6 )和角鲨烯衍生物2,3-二羟基-2,3-二氢角鲨烯(> 9 ),以及首次从Albizia属中报道的八种化合物;两个苄基糖苷,苄基1-O-β-d-吡喃葡萄糖苷(> 1 )和苄基6-O-α--1-阿拉伯吡喃糖基β-d-吡喃葡萄糖苷(> 2 ) ;三种无环单萜糖苷,芳基β-d-吡喃葡萄糖苷(> 3 )和芳基6-O-α-l-阿拉伯吡喃糖基-β-d-吡喃葡萄糖苷(> 4 ); (2 E )-3,7-二甲基辛基-2,6-二烯酸酯-6-O- α -l阿拉伯吡喃糖基-β -d -葡萄糖吡喃糖苷(> 5 ),两个寡糖苷, n -己基-α -l阿拉伯吡喃糖基-(1→6)-β< / em> -d-吡喃葡萄糖苷(creoside)(> 7 )和 n -辛基α -l-arabinopyranosyl-(1→6)- β -d-吡喃葡萄糖苷(rhodiooctanoside)(> 8 );和乙基果糖呋喃糖苷(> 10 )。基于对化合物1D和2D-NMR光谱,MS,UV和IR数据的广泛检查,阐明了分离出的化合物的结构。值得一提的是,据报道一些分离的芳樟醇糖苷衍生物是香气的前体。

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