methyl 2α,3β,19-trihydroxyurs-12-en-28-oate | 13850-15-2

• 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
• 英文名称: methyl 2α,3β,19-trihydroxyurs-12-en-28-oate
• 英文别名: 28-methoxytormentic acid；tormentic acid methyl ester；methyl (1R,2R,4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 13850-15-2
• 化学式: C₃₁H₅₀O₅
• 分子量: 502.735
• InChiKey: RQWXHGLRDYGNGZ-BPKREVGBSA-N

物化性质

• 熔点：
  156 °C
• 沸点：
  572.7±50.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2α,3β,19-trihydroxyurs-12-en-28-oate 在 溴 、 三丁基氧化锡 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 0.02h， 以62%的产率得到(2R,19R)-methyl 2,19-dihydroxy-3-oxours-12-en-28-carboxylate
  参考文献：
  名称：

  Tormentic acid derivatives: Synthesis and apoptotic activity

  摘要：

  Several derivatives of tormentic acid have been prepared and tested for their antitumor activity. The dichloroacetate 14 is an excellent antitumor active agent acting by an apoptose inducing pathway as demonstrated by OA/PI staining, DNA laddering experiments as well as by an annexin V binding assay. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.08.032
• 作为产物：
  描述：

  重氮甲烷 、 2Alpha,19Alpha-二羟基熊果酸 以 甲醇 、 乙醚 为溶剂， 反应 12.0h， 生成 methyl 2α,3β,19-trihydroxyurs-12-en-28-oate
  参考文献：
  名称：

  Triterpene Phytoalexins from Strawberry Fruit

  摘要：

  草莓品种Houkouwase对Colletotrichum fragariae的感染具有抗性。在受伤并接种了蕈蚊分生孢子的未成熟果实中观察到了抗真菌化合物的形成。分离出了三种抗真菌化合物，并确定它们分别是 euscaphic 酸、tormentic 酸和 myrianthic 酸。麝香草酸在 3 μg 的浓度下可抑制麝香草菌的生长，麝香草酸和麝香草酸在 100 μg 的浓度下具有抑制作用。对其含量的定量分析显示，三萜类化合物在受伤果实、受伤果实和接种果实中都有所增加，而在未处理的果实中却没有增加。这些结果表明，后洼地的未成熟果实会产生三萜类植物毒素。三萜类植物毒素似乎与草莓对真菌的抗性有关。

  DOI：

  10.1271/bbb.64.1707

文献信息

• Pentacylic triterpenes from <i>Lavandula coronopifolia</i>: structure related inhibitory activity on α-glucosidase
  作者：Marwa Elsbaey、Rogers Mwakalukwa、Kuniyoshi Shimizu、Tomofumi Miyamoto

  DOI：10.1080/14786419.2019.1655017

  日期：2021.5.3

  Abstract Ten pentacyclic triterpenes (1-10) were isolated from Lavandula coronopifolia. We evaluated their α-glucosidase inhibitory activity, and found that the aglycones, 1, 2, 3, 4, 7 and 10 showed superior IC50 values to the positive control. In order to explain the structural requirements for α-glucosidase inhibitory activity, eleven derivatives were prepared, including one new compound, 2-for

  摘要 十五环三萜（1 - 10）从分离薰衣草coronopifolia。我们评估了它们的α葡萄糖苷酶抑制活性，并发现该糖苷配基，1，2，3，4，图7和10显示出优异的IC 50个值以阳性对照。为了解释的结构要求α葡萄糖苷酶抑制活性，制备11组的衍生物，其中一个新的化合物，2-甲酰基- （A）1-19 α -羟基-1- norursane-2,12二烯28-油酸10c。结果表明，在A环上的游离羟基和在28位上的游离羧基是α-葡糖苷酶抑制活性的关键结构特征，并且，对于该活性，乌烷骨架是最佳的。此外，最有效的化合物pomolic acid 2的酶动力学分析表明，它以混合型方式抑制α-葡萄糖苷酶。分子对接模拟验证了这种抑制作用，并强调了C-3羟基和C-28羧基与硅酸酶相互作用中的作用。
• Triterpene Phytoalexins from Strawberry Fruit
  作者：Nobuhiro HIRAI、Megumi SUGIE、Mitsuo WADA、El Hassan LAHLOU、Tsunashi KAMO、Ryuji YOSHIDA、Mitsuya TSUDA、Hajime OHIGASHI

  DOI：10.1271/bbb.64.1707

  日期：2000.1

  Strawberry cv. Houkouwase is resistant to infection by Colletotrichum fragariae. The formation of antifungal compounds was observed in unripe fruit which had been wounded and inoculated with conidia of C. musae. Three antifungal compounds were isolated and identified as euscaphic acid, tormentic acid and myrianthic acid. Myrianthic acid inhibited the growth of C. musae at 3 μg, and euscaphic and tormentic acids showed inhibitory effects at 100 μg. A quantitative analysis of their contents showed that the triterpenes increased in wounded fruit, and in wounded and inoculated fruit, but not in non-treated fruit. These findings indicate that unripe fruit of Houkouwase produced the triterpenes as phytoalexins. The triterpene phytoalexins seem to be involved in the resistance of strawberry to the fungus.

  草莓品种Houkouwase对Colletotrichum fragariae的感染具有抗性。在受伤并接种了蕈蚊分生孢子的未成熟果实中观察到了抗真菌化合物的形成。分离出了三种抗真菌化合物，并确定它们分别是 euscaphic 酸、tormentic 酸和 myrianthic 酸。麝香草酸在 3 μg 的浓度下可抑制麝香草菌的生长，麝香草酸和麝香草酸在 100 μg 的浓度下具有抑制作用。对其含量的定量分析显示，三萜类化合物在受伤果实、受伤果实和接种果实中都有所增加，而在未处理的果实中却没有增加。这些结果表明，后洼地的未成熟果实会产生三萜类植物毒素。三萜类植物毒素似乎与草莓对真菌的抗性有关。
• Cecropioic acid, a pentacyclic triterpene from Musanga cecropioides
  作者：D. Lontsi、B.L. Sondengam、M.T. Martin、B. Bodo

  DOI：10.1016/s0031-9422(97)00789-9

  日期：1998.5

  Six pentacyclic triterpenes were isolated as their methyl ester from the methylated rootwood extracts of Musanga cecropioides and their structure elucidated by 2D-COSY spectroscopic methods. They were methyl tormentate, methyl 2-acetyltormentate, methyl 28-glucosyltormentate, methyl pomolate, methyl euscaphate and a new pentacyclic triterpene, methyl cecropioate (methyl 2α,11α-diacetoxy,3β,19α-dih

  从 Musanga cecropioides 的甲基化根材提取物中分离出六种五环三萜作为它们的甲酯，并通过 2D-COSY 光谱方法阐明了它们的结构。它们是甲基tormentate，methyl 2-acetyltormentate，methyl 28-glucosyltormentate，methyl pomolate，methyl euscaphate 和一种新的五环三萜，甲基cecropioate（甲基2α，11α-二乙酰氧基，3β，19α-dihydroxyurs-12-en-28-oate） .
• Triterpene acids from Myrianthus arboreus
  作者：Chukwunonye M. Ojinnaka、Joseph I. Okogun、Dominic A. Okorie

  DOI：10.1016/s0031-9422(00)91061-6

  日期：1980.1
• Reactions of 2,3,19-trihydroxyurs-12-triterpenoids: Pinacol rearrangement of methyl 2α,3β,19α-trihydroxyurs-12-en-28-oate
  作者：L.A Tapondjou、F.N. Ngounou、D. Lontsi、B.L. Sondengam、J.D. Connolly

  DOI：10.1016/s0040-4020(97)10418-5

  日期：1998.3

  Pinacol rearrangement of the title group of compounds has been investigated and the structures of the adducts elucidated. Three different A-ring carbonylated compounds were obtained, two of which (2 and 4) remained with a six-member ring as in the starting material 1, and the third one (3) with a cyclopentanic ring as a consequence of the A-ring contraction. In addition to normal pinacol rearrangement of ring A, the reaction led to the isomerization of Delta 12 double bond in all of the products (2-4) with compounds 2 and 3 as dienic triterpenes, and compound 4 with an E-ring gamma-lactonic system. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.