三对节萜酸 | 6488-64-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 三对节萜酸
• 英文名称: serratagenic acid
• 英文别名: (2R,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2,4a-dicarboxylic acid
• CAS: 6488-64-8
• 化学式: C₃₀H₄₆O₅
• 分子量: 486.692
• InChiKey: MCHKKYSPJGWAHQ-PGUYSIQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 三对节萜酸 以 甲醇 为溶剂， 生成 3β-olean-12-ene-28,29-dioic acid dimethyl ester
  参考文献：
  名称：

  Saponins from Chinese folk medicine, "Laing Wang Cha," leaves and stems of Nothopanax delavayi, Araliaceae.

  摘要：

  从中药“亮王茶”（五加科植物滇北五加的叶和叶柄）中分离出两种新的齐墩果烷型三萜糖苷，分别命名为亮王苷 I（1）和 II（2）。1 和 2 的结构分别为 28-β-D-吡喃葡萄糖基和 28-α-L-吡喃鼠李糖基（1→4）-β-D-吡喃葡萄糖基（1→6）-，分别是 3-O-α-L-阿拉伯吡喃糖基-3β-羟基齐墩果-12-烯-28,29-二酸的 β-D-吡喃葡萄糖基酯。

  DOI：

  10.1248/cpb.35.1486
• 作为产物：
  描述：

  liangwanoside II 在 盐酸 、 水 作用下， 以63.2 mg的产率得到三对节萜酸
  参考文献：
  名称：

  Chemical components from Metapanax delavayi leaves and their anti-BHP activities in vitro

  摘要：

  Two previously undescribed oleanane-type triterpene saponins named liangwanosides III-IV and one on described eudesmane glycoside named liangwanoside A were obtained from the leaves of Metapanax delavayi, a Chinese folk medicine especially for tea used in Yunnan, together with four known compounds. The structures of the undescribed compounds were determined by detailed spectroscopic (1D/2D NMR), HR-ESI-MS data analysis and chemical evidence. The activity against human benign prostate hyperplasia was evaluated with BPH-1 cell line. Most of the isolated compounds showed moderate inhibitory activity against BPH-1 cells at 100 and 50 mu M in vitro.

  DOI：

  10.1016/j.phytochem.2019.01.002

文献信息

• Triterpene compositions and methods for use thereof
  申请人：Research Development Foundation

  公开号：US20030039705A1

  公开（公告）日：2003-02-27

  The invention provides novel saponin mixtures and compounds which are isolated from the species Acacia victoriae and methods for their use. These compounds may contain a triterpene moiety, such as acacic or oleanolic acid, to which oligosaccharides and monoterpenoid moieties are attached. The mixtures and compounds have properties related to the regulation of apoptosis and cytotoxicity of cells and exhibit potent anti-tumor effects against a variety of tumor cells. The present application is a continuation-in-part of co-pending U.S. Patent Application Ser. No. 60/099,066, filed Sep. 3, 1998, and a continuation-in-part of U.S. patent application Ser. No. 60/085,997, filed May 19, 1998. The entire text of each of the above-referenced disclosures is specifically incorporated by reference herein without disclaimer.

  本发明提供了从维多利亚金合欢(Acacia victoriae)物种中分离出来的新型皂苷混合物和化合物，以及它们的使用方法。这些化合物可能包含三萜基团，如金合欢酸或齐墩果酸，附着有寡糖和单萜基团。这些混合物和化合物具有与细胞凋亡和细胞毒性调节相关的特性，并对多种肿瘤细胞表现出强效的抗肿瘤作用。本申请是待决美国专利申请号60/099,066的续篇，该专利申请于1998年9月3日提交，并且是待决美国专利申请号60/085,997的续篇，该专利申请于1998年5月19日提交。上述所有引用文件的全部内容都被明确地并入本文，不做免责声明。
• Sapogenins of Clerodendron serratum
  作者：S. Rangaswami、S. Sarangan

  DOI：10.1016/s0040-4020(01)82903-3

  日期：——
• New approaches to the structural modification of olean-type pentacylic triterpenes via microbial oxidation and glycosylation
  作者：Yu-Yao Zhu、Li-Wu Qian、Jian Zhang、Ji-Hua Liu、Bo-Yang Yu

  DOI：10.1016/j.tet.2011.04.055

  日期：2011.6

  Microbial transformation of 4 olean-type pentacyclic triterpenes (OPTs), 3-oxo oleanolic acid (1), 3-acetyl oleanolic acid (2), oleanolic acid (3), and esculentoside A (4) was studied. After the screening of 12 strains of microbes, preparative biotransformation by two strains of Streptomyces griseus ATCC 13273 and Aspergillus ochraceus CICC 40330 resulted in the isolation of 10 metabolites. The microbial catalyzed high efficient regio-selective methyl oxidation and glycosylation were discovered, which could be provided as an alternative method to expand the structural diversity of OPTs. All the structures of the metabolites were elucidated unambiguously by ESI-MS, H-1 NMR, C-13 NMR, and 2D-NMR spectroscopy. (C) 2011 Elsevier Ltd. All rights reserved.
• TRITERPENE COMPOSITIONS AND METHODS FOR USE THEREOF
  申请人：RESEARCH DEVELOPMENT FOUNDATION(a Nevada corporation)

  公开号：EP1079824A1

  公开（公告）日：2001-03-07
• EP1079824A4
  申请人：——

  公开号：EP1079824A4

  公开（公告）日：2008-03-12