来自木本苜蓿叶片的三萜类糖苷
Triterpenoid glycosides from leaves of Medicago arborea L.
作者信息
Tava Aldo, Mella Mariella, Avato Pinarosa, Argentieri Maria Pia, Bialy Zbigniew, Jurzysta Marian
机构信息
C.R.A. Istituto Sperimentale per le Colture Foraggere, Viale Piacenza 29, 26900 Lodi, Italy.
出版信息
J Agric Food Chem. 2005 Dec 28;53(26):9954-65. doi: 10.1021/jf052468x.
Eighteen triterpene saponins (1-18) from Medicago arborea leaves have been isolated and their structures elucidated by spectroscopic, spectrometric (1D and 2D NMR, FAB-MS, ESI-MS/MS), and chemical methods. They have been identified as glycosides of medicagenic, zanhic, and 2beta-hydroxyoleanolic acids, soyasapogenol B, bayogenin, and 2beta,3beta-dihydroxyolean-12-en-23-al-28-oic acid. Twelve of them, identified as 3-O-beta-D-glucopyranosyl-28-O-[alpha-L-arabinopyranosyl(1-->3)-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside] zanhic acid (3), 3-O-beta-D-glucopyranosyl-28-O-[beta-D-xylopyranosyl(1-->4)-[alpha-L-arabinopyranosyl-(1-->3)]-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside] zanhic acid (4), 3-O-[alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl(1-->2)-beta-D-glucopyranosyl]-2beta-hydroxyoleanolic acid (5), 3-O-beta-D-glucuronopyranosyl-28-O-[alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside]medicagenic acid (6), 3-O-beta-D-glucuronopyranosyl-28-O-[beta-D-xylopyranosyl(1-->4)-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside]bayogenin (9), 3-O-beta-D-glucuronopyranosyl-28-O-[beta-D-xylopyranosyl(1-->4)-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside]-2beta,3beta-dihydroxyolean-12-en-23-al-28-oic acid (10), 3-O-beta-D-glucuronopyranosyl-28-O-[beta-D-xylopyranosyl(1-->4)-[beta-D-apiofuranosyl(1-->3)]-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside]zanhic acid (12), 3-O-beta-D-glucuronopyranosyl-28-O-[beta-D-xylopyranosyl(1-->4)-[alpha-L-arabinopyranoside(1-->3)]-alpha-L-rhamnopyrano-syl(1-->2)-alpha-L-arabinopyranoside]zanhic acid (13), 3-O-beta-D-glucuronopyranosyl-28-O-[beta-D-xylopyrano-syl(1-->4)-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside]zanhic acid (14), 3-O-[alpha-L-arabinopyranosyl-(1-->2)-beta-D-glucopyranosyl(1-->2)-beta-D-glucopyranosyl]-28-O-[beta-D-xylopyranosyl(1-->4)-[beta-D-apiofurano-syl(1-->3)]-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside]zanhic acid (16), 3-O-[beta-D-glucopyrano-syl(1-->2)-beta-D-glucopyranosyl]-28-O-[beta-D-xylopyranosyl(1-->4)-[alpha-L-arabinopyranosyl(1-->3)]-alpha-L-rhamno-pyranosyl (1-->2)-alpha-L-arabinopyranoside]zanhic acid (17), and 3-O-beta-D-glucuronopyranosyl-28-O-[beta-D-xylopyranosyl(1-->4)-[beta-D-apiofuranosyl(1-->3)]-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyrano-side]medicagenic acid (18), are reported as new natural compounds. The presence of the aldehydic group on the sapogenin moiety of saponin 10 is discussed in the framework of a possible elucidation of the biosynthesis of these metabolites.
从木本苜蓿叶中分离出18种三萜皂苷（1 - 18），并通过光谱、波谱法（一维和二维核磁共振、快原子轰击质谱、电喷雾串联质谱）以及化学方法阐明了它们的结构。它们被鉴定为苜蓿酸、赞尼酸、2β - 羟基齐墩果酸、大豆皂醇B、白元酸和2β,3β - 二羟基齐墩果 - 12 - 烯 - 23 - 醛 - 28 - 酸的糖苷。其中12种，分别鉴定为3 - O - β - D - 吡喃葡萄糖基 - 28 - O - [α - L - 吡喃阿拉伯糖基(1→3) - α - L - 吡喃鼠李糖基(1→2) - α - L - 吡喃阿拉伯糖苷]赞尼酸（3）、3 - O - β - D - 吡喃葡萄糖基 - 28 - O - [β - D - 吡喃木糖基(1→4) - [α - L - 吡喃阿拉伯糖基 - (1→3)] - α - L - 吡喃鼠李糖基(1→2) - α - L - 吡喃阿拉伯糖苷]赞尼酸（4）、3 - O - [α - L - 吡喃鼠李糖基(1→2) - α - L - 吡喃阿拉伯糖基(1→2) - β - D - 吡喃葡萄糖基] - 2β - 羟基齐墩果酸（5）、3 - O - β - D - 吡喃葡萄糖醛酸基 - 28 - O - [α - L - 吡喃鼠李糖基(1→2) - α - L - 吡喃阿拉伯糖苷]苜蓿酸（6）、3 - O - β - D - 吡喃葡萄糖醛酸基 - 28 - O - [β - D - 吡喃木糖基(1→4) - α - L - 吡喃鼠李糖基(1→2) - α - L - 吡喃阿拉伯糖苷]白元酸（9）、3 - O - β - D - 吡喃葡萄糖醛酸基 - 28 - O - [β - D - 吡喃木糖基(1→4) - α - L - 吡喃鼠李糖基(1→2) - α - L -吡喃阿拉伯糖苷] - 2β,3β - 二羟基齐墩果 - 12 - 烯 - 23 - 醛 - 28 - 酸（10）、3 - O - β - D - 吡喃葡萄糖醛酸基 - 28 - O - [β - D - 吡喃木糖基(1→4) - [β - D - 呋喃芹菜糖基(1→3)] - α - L - 吡喃鼠李糖基(1→2) - α-L - 吡喃阿拉伯糖苷]赞尼酸（12）、3 - O - β - D - 吡喃葡萄糖醛酸基 - 28 - O - [β - D - 吡喃木糖基(1→4) - [α - L - 吡喃阿拉伯糖苷(1→3)] - α - L - 吡喃鼠李糖基(1→2) - α - L - 吡喃阿拉伯糖苷]赞尼酸（13）、3 - O - β - D - 吡喃葡萄糖醛酸基 - 28 - O - [β - D - 吡喃木糖基(1→4) - α - L - 吡喃鼠李糖基(1→2) - α - L - 吡喃阿拉伯糖苷]赞尼酸（14）、3 - O - [α - L - 吡喃阿拉伯糖基 - (1→2) - β - D - 吡喃葡萄糖基(1→2) - β - D - 吡喃葡萄糖基] - 28 - O - [β - D - 吡喃木糖基(1→4) - [β - D - 呋喃芹菜糖基(1→3)] - α - L - 吡喃鼠李糖基(1→) - α - L - 吡喃阿拉伯糖苷]赞尼酸（16）、3 - O - [β - D - 吡喃葡萄糖基(1→2) - β - D - 吡喃葡萄糖基] - 28 - O - [β - D - 吡喃木糖基(1→4) - [α - L - 吡喃阿拉伯糖基(1→3)] - α - L - 吡喃鼠李糖基 (1→2) - α - L - 吡喃阿拉伯糖苷]赞尼酸（17）以及3 - O - β - D - 吡喃葡萄糖醛酸基 - 28 - O - [β - D - 吡喃木糖基(1→4) - [β - D - 呋喃芹菜糖基(1→3)] - α - L - 吡喃鼠李糖基(1→2) - α - L - 吡喃阿拉伯糖苷]苜蓿酸（18），被报道为新的天然化合物。在这些代谢产物生物合成的可能阐释框架内，讨论了皂苷10的皂苷元部分上醛基的存在情况。
Zotero 插件