acridocarpusic acid D | 721942-62-7

• 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: acridocarpusic acid D
• 英文别名: (4aS,6aR,6aR,6bR,8aR,10R,12aR,14aS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-3,4,5,6,6a,7,8,8a,10,11,12,13,14,14a-tetradecahydropicene-4a-carboxylic acid
• CAS: 721942-62-7
• 化学式: C₃₀H₄₈O₃
• 分子量: 456.709
• InChiKey: RGZSSKBTFGNUCG-ZGXCSZCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  acridocarpusic acid D 、 乙酸酐 在 吡啶 作用下， 反应 18.0h， 以92%的产率得到acridocarpusic acid E
  参考文献：
  名称：

  从山毛榉蛋白开始高效合成苹果酸和相关三萜

  摘要：

  Morolic acid（1）是一种天然存在的五环三萜，其衍生物具有良好的抗HIV和其他生物活性。的有效的合成1已经结合的24％桦木醇从开始的总产11层的步骤而完成的。还合成了一些相关的天然三萜，其中包括吗啡醇（4），cri果酸D（5），carp果酸E（6）和吗啉醛（7）。生物测定的结果表明，1，5，和6表现出对糖原磷酸化酶中等抑制活性。

  DOI：

  10.1016/j.tet.2009.03.100
• 作为产物：
  描述：

  黄莲木酸 在 aluminum (III) chloride 、 aluminum isopropoxide 、 异丙醇 、 盐酸 作用下， 以 水 、 异丙醇 为溶剂， 反应 4.0h， 以46%的产率得到acridocarpusic acid D
  参考文献：
  名称：

  从山毛榉蛋白开始高效合成苹果酸和相关三萜

  摘要：

  Morolic acid（1）是一种天然存在的五环三萜，其衍生物具有良好的抗HIV和其他生物活性。的有效的合成1已经结合的24％桦木醇从开始的总产11层的步骤而完成的。还合成了一些相关的天然三萜，其中包括吗啡醇（4），cri果酸D（5），carp果酸E（6）和吗啉醛（7）。生物测定的结果表明，1，5，和6表现出对糖原磷酸化酶中等抑制活性。

  DOI：

  10.1016/j.tet.2009.03.100

文献信息

• Antimicrobial activity of Schinus lentiscifolius (Anacardiaceae)
  作者：Ilaine T.S. Gehrke、Alexandre T. Neto、Marcelo Pedroso、Clarice P. Mostardeiro、Ivana B.M. Da Cruz、Ubiratan F. Silva、Vinicius Ilha、Ionara I. Dalcol、Ademir F. Morel

  DOI：10.1016/j.jep.2013.04.043

  日期：2013.7

  Ethnopharmacological relevance: Schinus lentiscifolius Marchand (syn. Schinus weinmannifolius Engl) is a plant native to Rio Grande do Sul (Southern Brazil) and has been used in Brazilian traditional medicine as antiseptic and antimicrobial for the treatment of many different health problems as well as to treat leucorrhea and to assist in ulcer and wound healing. Although it is a plant widely used by the population, there are no studies proving this popular use.Material and methods: The crude aqueous extract, the crude neutral methanol extract, fractions prepared from this extract (n-hexane, ethyl acetate, and n-butanol), pure compounds isolated from these fractions, and derivatives were investigated in vitro for antimicrobial activities against five Gram positive bacteria: Bacillus subtilis, Staphylococcus aureus, Staphylococcus epidermidis, Staphylococcus saprophyticus, Streptococcus pyogenes, three Gram negative bacteria: Escherichia coli, Pseudomonas aeruginosa, and Shigella sonnei, and four yeasts: Candida albicans, Candida tropicalis, Cryptococcus neoformans, and Saccharomyces cerevisiae. The isolated compound moronic acid, which is the most active, was tested against a range of other bacteria such as two Gram positive bacteria, namely, Bacillus cereus, Enterococcus spp, and six Gram negative bacteria, namely, Burkholderia cepacia, Providencia stuartii, Morganella morganii, Enterobacter cloacae, Enterobacter aerogenes, and Proteus mirabilis.Results: The leaf aqueous extract (decoction) of Schinus lentiscifolius showed a broad spectrum of antibacterial activity, ranging from 125 to 250 mu g/ml (MIC) against the tested bacteria and fungi. The n-hexane extract, despite being very little active against bacteria, showed an excellent antifungal activity, especially against Candida albicans (MIC=25 mu g/ml), Candida tropicalis (MIC=15.5 mu g/ml), and Cryptococcus neoformans, (MIC=15.5 mu g/ml). From the acetate fraction (the most active against bacteria), compounds 1-6 were isolated: nonadecanol (1), moronic acid (2), gallic acid methyl ester (3), gallic acid (4), quercetin (5) and quercitrin (6). The minimal inhibitory concentration (MIC) of moronic acid between 1.5 and 3 mu g/ml against most of the tested bacteria shows that it is one of the metabolites responsible for the antibacterial activity of Schinus lentiscifolius.Conclusion: The antimicrobial activity and some constituents of Schinus lentiscifolius are reported for the first time. The results of the present study provide scientific basis for the popular use of Schinus lentiscifolius for a number of different health problems. (C) 2013 Elsevier Ireland Ltd. All rights reserved.
• Efficient synthesis of morolic acid and related triterpenes starting from betulin
  作者：Pu Zhang、Jia Hao、Jun Liu、Luyong Zhang、Hongbin Sun

  DOI：10.1016/j.tet.2009.03.100

  日期：2009.5

  Morolic acid (1) is a naturally occurring pentacyclic triterpene whose derivatives exhibit promising anti-HIV and other biological activities. An efficient synthesis of 1 has been accomplished in 11 steps with a total yield of 24% starting from betulin. Some related natural triterpenes including moradiol (4), acridocarpusic acid D (5), acridocarpusic acid E (6), and moronic aldehyde (7) have also been

  Morolic acid（1）是一种天然存在的五环三萜，其衍生物具有良好的抗HIV和其他生物活性。的有效的合成1已经结合的24％桦木醇从开始的总产11层的步骤而完成的。还合成了一些相关的天然三萜，其中包括吗啡醇（4），cri果酸D（5），carp果酸E（6）和吗啉醛（7）。生物测定的结果表明，1，5，和6表现出对糖原磷酸化酶中等抑制活性。