moronic acid methyl ester | 55887-94-0

• 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: moronic acid methyl ester
• 英文别名: methyl moronate；3-Oxoolean-18-en-28-oic acid methyl ester；methyl (4aS,6aR,6aR,6bR,8aR,12aR,14aS)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-4,5,6,6a,7,8,8a,11,12,13,14,14a-dodecahydro-3H-picene-4a-carboxylate
• CAS: 55887-94-0
• 化学式: C₃₁H₄₈O₃
• 分子量: 468.72
• InChiKey: RGKMKULXFZOUPF-XRGYSQAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  34
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  moronic acid methyl ester 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 morolic acid methyl ester
  参考文献：
  名称：

  3-oxo-6β-hydroxyolean-18-en-28-oic acid from orthopterygium huancuy

  摘要：

  DOI：

  10.1016/s0031-9422(00)80284-8
• 作为产物：
  描述：

  morolic acid methyl ester 在 chromium(VI) oxide 作用下， 生成 moronic acid methyl ester
  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

文献信息

• In vitro and in silico PTP-1B inhibition and in vivo antidiabetic activity of semisynthetic moronic acid derivatives
  作者：Litzia Cerón-Romero、Paolo Paoli、Guido Camici、Virginia Flores-Morales、María Yolanda Rios、Juan J. Ramírez-Espinosa、Sergio Hidalgo-Figueroa、Gabriel Navarrete-Vázquez、Samuel Estrada-Soto

  DOI：10.1016/j.bmcl.2016.02.082

  日期：2016.4

  Six derivatives (1–6) of moronic acid were semi-synthesized and their in vitro protein tyrosine phosphatase 1B (PTP-1B) inhibition activity assessed. Derivatives 2 (IC50 = 10.8 ± 0.5 μM) and 6 (IC50 = 7.5 ± 0.1 μM) displayed the most potent inhibitory activity. Therefore, they (50 mg/Kg) were tested for their antidiabetic effect in vivo using a non-insulin dependent diabetes mellitus rat model. The

  半合成了六个（1 – 6）的巴豆酸衍生物，并评估了它们的体外蛋白酪氨酸磷酸酶1B（PTP-1B）抑制活性。衍生物2（IC 50  = 10.8±0.5μM）和6（IC 50  = 7.5±0.1μM）显示出最有效的抑制活性。因此，使用非胰岛素依赖性糖尿病大鼠模型测试了它们（50 mg / Kg）的体内抗糖尿病作用。结果表明，它们在所有实验过程中均降低了血浆葡萄糖水平（p <0.05）。对2和6与PTP-1B正构位点A和别构位点B的对接分析表明，2在两个位点均与Val49，Gln262，Met258，Phe182，Ala217，Ile219和Gly259发生极性和范德华相互作用，显示出与位点A的亲和力更高。化合物6与Gln262和范德华与Val49，Ile219，Gly259， Arg254，Ala27，Phe52，Met258，Asp48和Phe182，表明潜在的结合位点位于位点B，靠近催
• 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.
• 60. Triterpenoids. Part I. Morolic acid, a new triterpenoid sapogenin
  作者：D. H. R. Barton、C. J. W. Brooks

  DOI：10.1039/jr9510000257

  日期：——
• 3-oxo-6β-hydroxyolean-18-en-28-oic acid from orthopterygium huancuy
  作者：Antonio G. González、José Amaro、Braulio M. Fraga、Javier G. Luis

  DOI：10.1016/s0031-9422(00)80284-8

  日期：1983.1