methyl 3β-hydroxyoleana-9(11),12-dien-28-oate | 220618-73-5

• 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 3β-hydroxyoleana-9(11),12-dien-28-oate
• 英文别名: methyl-3β-hydroxyolean-9(11),12-dien-28-oate；sabialimon N；3β-hydroxy-oleanadien-(9(11).12)-oic acid-(28)-methyl ester；3β-Hydroxy-oleanadien-(9(11).12)-saeure-(28)-methylester；methyl (4aS,6aR,6bS,8aR,10S,12aS,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,14b-dodecahydropicene-4a-carboxylate
• CAS: 220618-73-5
• 化学式: C₃₁H₄₈O₃
• 分子量: 468.72
• InChiKey: ROWAKJPQESBVOT-BTIXHMCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3β-hydroxyoleana-9(11),12-dien-28-oate 以 乙醇 为溶剂， 反应 0.33h， 以95%的产率得到(4aS,8aS)-8-[(Z)-2-((4aR,6S,8aS)-6-Hydroxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-vinyl]-2,2,7-trimethyl-1,3,4,5,6,8a-hexahydro-2H-naphthalene-4a-carboxylic acid methyl ester
  参考文献：
  名称：

  由齐墩果酸和山梨酸部分合成C环衍生物。通过化学和光化学异构化过程形成数个三烯系统

  摘要：

  从橄榄油压榨固体废物中所含的齐墩果酸半合成了一些在C环上改性的三萜类化合物。齐墩果酸和山lin酸的相应酯使产物具有二烯体系，其通过电环反应产生类似于维生素原D 2的油烯酮。这些化合物的化学和光化学异构化反应产生了两种不同的三烯，其结构与速甾醇和维生素D 2相似。

  DOI：

  10.1016/j.tet.2003.12.023
• 作为产物：
  描述：

  齐墩果酸 在 N-溴代丁二酰亚胺(NBS) 、 calcium carbonate 作用下， 以 1,4-二氧六环 、 乙醚 、 水 为溶剂， 反应 30.0h， 生成 methyl 3β-hydroxyoleana-9(11),12-dien-28-oate
  参考文献：
  名称：

  C环修饰的齐墩果酸衍生物的合成及其细胞毒性评价。

  摘要：

  通过在各种实验条件下用NBS处理对齐墩果酸的C环进行化学修饰。通过光谱分析（（1）H和（13）C NMR和质量）建立合成的化合物的结构。通过使用MTT测定法针对一组五种人类癌细胞系评估了所有化合物。在测试的化合物中，2和7对乳腺癌细胞系MCF-7表现出显着的活性。最显着的是，化合物7对MCF-7癌细胞系的活性（IC50：2.96μM）比亲本（1）和中间体化合物（6）高出几倍。流式细胞仪分析表明，这些化合物使细胞周期停滞在G0 / G1期，并诱导线粒体介导的细胞凋亡。

  DOI：

  10.1016/j.bioorg.2016.08.001

文献信息

• Biotransformation of oleanolic and maslinic methyl esters by Rhizomucor miehei CECT 2749
  作者：Antonio Martinez、Alberto Perojil、Francisco Rivas、Andres Parra、Andres Garcia-Granados、Antonia Fernandez-Vivas

  DOI：10.1016/j.phytochem.2015.07.020

  日期：2015.9

  The pentacyclic triterpenoids methyl oleanolate, methyl maslinate, methyl 3 beta-hydroxyolean-9(11),12-dien-28-oate, and methyl 2 alpha,3 beta-dihydroxy-12 beta,13 beta-epoxyolean-28-oate were biotransformed by Rhizomucor miehei CECT 2749. Microbial transformation of methyl oleanolate produced only a 7 beta,30-di-hydroxylated metabolite with a conjugated 9(11),12-diene system in the C ring. Biotransformation of the substrate with this 9(11),12-diene system gave the same 7 beta,30-dihydroxylated compound together with a 7 beta,15 alpha,30-trihydroxyl derivative. The action of this fungus (R. miehei) on methyl maslinate was more varied, isolating metabolites with a 30-hydroxyl group, a 9(11),12-diene system, an 11-oxo group, or an 12-oxo group. Microbial transformation of the substrate with a 12 beta,13 beta-epoxy function resulted in the isolation of two metabolites with 12-oxo and 28,13 beta-olide groups, hydroxylated or not at C-7 beta, together with a 30-hydroxy-12-oxo derivative. The structures of these derivatives were deduced by extensive and rigorous spectroscopic studies. (C) 2015 Elsevier Ltd. All rights reserved.
• Midazolam attenuates ketamine-induced abnormal perception and thought process but not mood changes
  作者：Manzo Suzuki、Kentaro Tsueda、Peter S. Lansing、Merritt M. Tolan、Thomas M Fuhrman、Rachel A. Sheppard、Harrell E. Hurst、Steven B. Lippmann

  DOI：10.1007/bf03019666

  日期：2000.9

  Purpose: To determine the effects of midazolam, 30 ng.mL(-1), on altered perception, mood, and cognition induced by ketamine.Methods: After ketamine was administered to achieve target concentrations of 50, 100, or 150 ng.mL(-1) in 11 volunteers, perception, mood, and thought process were assessed by a visual analog scale. Mini-Mental State examination (MMSE) assessed cognition. Boluses of midazolam, 30, 14.5, and 12 mu g.kg(-1), were injected every 30 min to maintain the plasma concentration at 30 ng.mL(-1), which was reached 30 min after each injection.Results: Ketamine produced changes in perception about the body (P < 0.01, 0.001, and 0.0001 at 30, 60, and 90 min), surroundings (P < 0.01 and 0.0001 at 60 and 90 min), time (P < 0.002 and 0.0001 at 60 and 90 min), reality (P < 0.001 and 0.0001 at 60 and 90 min), sounds (P < 0.002 at 90 min), and meaning(P < 0.05 at 30 min), Subjects felt less energetic and clearheaded (P < 0.02 and 0.05) during ketamine, midazolam, and their coadministration. Ketamine impaired thought process (P < 0.003 and 0.0001 at 60 and 90 min). Ketamine and midazolam decreased mean total MMSE and recall scores (P < 0.001 for both). Go-administration reduced the number of subjects with perceptual (body, P < 0.01 and 0.001 at 30 and 60 min) and thought process abnormalities. Within the range of observation, co-administration did not affect the changes in mood or recall.Conclusion: Midazolam attenuates ketamine-induced changes in perception and thought process.
• Partial synthesis of C-ring derivatives from oleanolic and maslinic acids. Formation of several triene systems by chemical and photochemical isomerization processes
  作者：Andrés Garcı́a-Granados、Pilar E López、Enrique Melguizo、Andrés Parra、Yolanda Simeó

  DOI：10.1016/j.tet.2003.12.023

  日期：2004.2

  Some triterpenic compounds modified in C-ring were semi-synthesised from oleanolic acid contained in the solid waste of olive-oil pressing. The corresponding esters of oleanolic and maslinic acids rendered products with a diene system, which led to oleantrienes resembling previtamin D2 by an electrocyclic reaction. Chemical and photochemical isomerization of these compounds yielded two different trienes

  从橄榄油压榨固体废物中所含的齐墩果酸半合成了一些在C环上改性的三萜类化合物。齐墩果酸和山lin酸的相应酯使产物具有二烯体系，其通过电环反应产生类似于维生素原D 2的油烯酮。这些化合物的化学和光化学异构化反应产生了两种不同的三烯，其结构与速甾醇和维生素D 2相似。
• Synthesis of ring-C modified oleanolic acid derivatives and their cytotoxic evaluation
  作者：Banita Pattnaik、Vadithe Lakshma Nayak、Sistla Ramakrishna、Uppuluri Venkata Mallavadhani

  DOI：10.1016/j.bioorg.2016.08.001

  日期：2016.10

  Ring-C of oleanolic acid was chemically modified by treating with NBS under a variety of experimental conditions. The structures of the synthesized compounds were established by spectral analysis ((1)H &(13)C NMR and Mass). All the compounds were evaluated against a panel of five human cancer cell lines by using MTT assay. Among the tested compounds, 2 and 7 showed significant activity against breast

  通过在各种实验条件下用NBS处理对齐墩果酸的C环进行化学修饰。通过光谱分析（（1）H和（13）C NMR和质量）建立合成的化合物的结构。通过使用MTT测定法针对一组五种人类癌细胞系评估了所有化合物。在测试的化合物中，2和7对乳腺癌细胞系MCF-7表现出显着的活性。最显着的是，化合物7对MCF-7癌细胞系的活性（IC50：2.96μM）比亲本（1）和中间体化合物（6）高出几倍。流式细胞仪分析表明，这些化合物使细胞周期停滞在G0 / G1期，并诱导线粒体介导的细胞凋亡。