(3beta)-3-羟基-齐墩果-18-烯-28-酸 | 559-68-2

• 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
• 中文名称: (3beta)-3-羟基-齐墩果-18-烯-28-酸
• 中文别名: 摩尔酸
• 英文名称: Morolic acid
• 英文别名: (3β)-3-hydroxyolean-18-en-28-oic acid；3β-hydroxyoleane-18-ene-28-oic acid；3β-hydroxyolean-18-en-28-oic acid；3β-hydroxy-olean-18-en-28-oic acid；3β-Hydroxy-olean-18-en-28-saeure；(4aS,6aR,6aR,6bR,8aR,10S,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: 559-68-2
• 化学式: C₃₀H₄₈O₃
• 分子量: 456.709
• InChiKey: RGZSSKBTFGNUCG-VNTGHVHSSA-N

物化性质

• 熔点：
  309 °C
• 沸点：
  551.8±50.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

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：

  (3beta)-3-羟基-齐墩果-18-烯-28-酸 生成 日耳曼醇
  参考文献：
  名称：

  60.三萜。第一部分：叶酸，一种新的三萜类皂苷元

  摘要：

  DOI：

  10.1039/jr9510000257
• 作为产物：
  描述：

  3β-acetoxy-19α-hydroxy-olean-12-en-28-oic acid methyl ester 生成 (3beta)-3-羟基-齐墩果-18-烯-28-酸
  参考文献：
  名称：

  Barton et al., Journal of the Chemical Society, 1951, p. 278

  摘要：

  DOI：

文献信息

• Anti-AIDS Agents 81. Design, Synthesis, and Structure−Activity Relationship Study of Betulinic Acid and Moronic Acid Derivatives as Potent HIV Maturation Inhibitors
  作者：Keduo Qian、Reen-Yun Kuo、Chin-Ho Chen、Li Huang、Susan L. Morris-Natschke、Kuo-Hsiung Lee

  DOI：10.1021/jm901782m

  日期：2010.4.22

  as potent anti-HIV agents, different C-3 conformationally restricted betulinic acid (BA, 1) derivatives were designed and synthesized in order to explore the conformational space of the C-3 pharmacophore. 3-O-Monomethylsuccinyl-betulinic acid (MSB) analogues were also designed to better understand the contribution of the C-3′ dimethyl group of bevirimat (2), the first-in-class HIV maturation inhibitor

  在我们将三萜衍生物作为有效抗 HIV 药物的持续研究中，设计并合成了不同的 C-3 构象限制桦木酸 (BA, 1 ) 衍生物，以探索 C-3 药效团的构象空间。还设计了3 - O-单甲基琥珀酰-桦木酸 (MSB) 类似物以更好地了解 bevirimat ( 2 )的 C-3' 二甲基基团的贡献，bevirimat ( 2 ) 是一流的 HIV 成熟抑制剂，目前处于 IIb 期临床试验。此外，另一种三萜骨架，吗啉酸（MA，3)，还用于研究骨架和 C-3 修饰对此类化合物的抗 HIV 活性的影响。这项研究使我们能够更好地了解三萜衍生的抗 HIV 药物的构效关系 (SAR)，并导致化合物12 (EC 50 : 0.0006 μM)的设计和合成，其活性略好于2作为HIV-1 成熟抑制剂。
• 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。
• Glochodpurnoid B from Glochidion puberum Induces Endoplasmic Reticulum Stress-Mediated Apoptosis in Colorectal Cancer Cells
  作者：Yang Tian、Runzhu Fan、Zhao Yin、Yongping Huang、Dong Huang、Fangyu Yuan、Aiping Yin、Guihua Tang、Rong Pu、Sheng Yin

  DOI：10.3390/molecules28020511

  日期：——

  Glochidpurnoids A and B (1 and 2), two new coumaroyl or feruloyl oleananes, along with 17 known triterpenoids (3-19) were obtained from the stems and twigs of Glochidion puberum. Their structures were elucidated by extensive spectroscopic data analyses, chemical methods, and single crystal X-ray diffraction. All compounds were screened for cytotoxicity against the colorectal cancer cell line HCT-116

  Glochidpurnoids A 和 B（1 和 2），两种新的香豆酰或阿魏酰齐墩果烷，以及 17 种已知的三萜类化合物 (3-19) 是从 Glochidion puberum 的茎和枝条中获得的。通过广泛的光谱数据分析、化学方法和单晶 X 射线衍射阐明了它们的结构。筛选所有化合物对结直肠癌细胞系 HCT-116 的细胞毒性，2、3、5、6、11 和 17 显示出显着的抑制活性（IC50：0.80-2.99 μM），活性高于阳性对照 5 -氟尿嘧啶 (5-FU)。作用最强的化合物 2 的机理研究表明，它可以诱导内质网 (ER) 应激介导的细胞凋亡，并提高 HCT-116 细胞对 5-FU 的敏感性。
• 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.
• Triterpene derivatives that inhibit human immunodeficiency virus type 1 replication
  作者：Casey R. Dorr、Sergiy Yemets、Oksana Kolomitsyna、Pavel Krasutsky、Louis M. Mansky

  DOI：10.1016/j.bmcl.2010.10.078

  日期：2011.1

  Triterpene derivatives were analyzed for anti-HIV-1 activity and for cellular toxicity. Betulinic aldehyde, betulinic nitrile, and morolic acid derivatives were identified to have anti-HIV-1 activity. These derivatives inhibit a late step in virus replication, likely virus maturation. (C) 2010 Elsevier Ltd. All rights reserved.