来自白薯种子粗树脂糖苷部分的十一种新糖苷酸甲酯。
Eleven new glycosidic acid methyl esters from the crude resin glycoside fraction of Ipomoea alba seeds.
发表日期:2024 Aug 19
作者:
Nodoka Misuda, Hirotaka Nishikawa, Shin Yasuda, Hiroyuki Miyashita, Hitoshi Yoshimitsu, Ryota Tsuchihashi, Masafumi Okawa, Junei Kinjo, Masateru Ono
来源:
Cellular & Molecular Immunology
摘要:
树脂糖苷是旋花科植物的特征,是生药中众所周知的泻药成分,例如传统药物中使用的墨西哥胡椒、哈拉帕块茎和牵牛花子,这些药物均来自于该科植物。分离的树脂糖苷已表现出多种生物活性,包括抗菌、离子传导、抗炎、抗病毒和多药耐药性调节特性,以及针对癌细胞的细胞毒性。这些化合物由羟基脂肪酸寡糖苷(糖苷酸)组成,部分糖部分被一些有机酸酰化以形成核心结构。本研究调查了从 Ipomoea alba L. 种子(旋花科)的甲醇提取物中获得的粗树脂糖苷部分的糖苷酸成分。从用己烷中的三甲基甲硅烷基重氮甲烷处理的糖苷酸级分中分离出十一种新的糖苷酸甲酯和一种已知的甲酯。使用酸性水解、电喷雾电离时间质谱和核磁共振光谱分析确定了它们的结构。这些化合物是五糖苷、四糖苷或三糖苷,以 11S-羟基十四烷酸甲酯或 11S-羟基十六烷酸甲酯作为苷元。虽然D-奎诺糖和L-鼠李糖是常见的单糖成分,但其余的单糖是D-葡萄糖、D-木糖或D-岩藻糖。粗树脂糖苷部分对 HL-60 人类早幼粒细胞白血病细胞显示出不可忽略的细胞毒性。© 2024。作者获得日本生药学会的独家许可。
Resin glycosides are characteristic of plants of the Convolvulaceae family and are well-known purgative ingredients in crude drugs, such as Rhizoma Jalapae, Orizaba Jalapa Tuber, and Pharbitidis Semen, which are used in traditional medicine and derived from plants belonging to this family. Isolated resin glycosides have demonstrated diverse biological activities, including antibacterial, ionophoric, anti-inflammatory, antiviral, and multidrug-resistance-modulating properties, as well as cytotoxicity against cancer cells. These compounds consist of hydroxyl fatty acid oligoglycosides (glycosidic acids), with portions of the saccharide moieties acylated with some organic acids to form the core structure. This study investigated the glycosidic acid components of a crude resin glycoside fraction obtained from a methanolic extract of Ipomoea alba L. seeds (Convolvulaceae). Eleven new glycosidic acid methyl esters and one known methyl ester were isolated from a glycosidic acid fraction treated with trimethylsilyldiazomethane in hexane. Their structures were determined using acidic hydrolysis and electrospray ionization-time of fight mass spectrometry and NMR spectral analyses. These compounds are penta-, tetra-, or triglycosides, with methyl 11S-hydroxytetradecanoate or methyl 11S-hydroxyhexadecanoate as the aglycone. Although D-quinovose and L-rhamnose are common monosaccharide components, the remaining monosaccharides are D-glucose, D-xylose, or D-fucose. The crude resin glycoside fraction showed non-negligible cytotoxicity against HL-60 human promyelocytic leukemia cells.© 2024. The Author(s) under exclusive licence to The Japanese Society of Pharmacognosy.