oleanene-(12)-diol-(3β.16α) | 64188-27-8

• 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: oleanene-(12)-diol-(3β.16α)
• 英文别名: (4aS)-5t.10c-Dihydroxy-2.2.4ar.6at.6bc.9.9.12ac-octamethyl-(8atH.12btH.14bcH)-Δ¹⁴-eicosahydro-picen；Oleanen-(12)-diol-(3β.16α)；16alpha-Hydroxy-beta-amyrin；(3S,4aR,6aR,6bS,8R,8aS,12aS,14aR,14bR)-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8-diol
• CAS: 64188-27-8
• 化学式: C₃₀H₅₀O₂
• 分子量: 442.726
• InChiKey: VLRYIIPJIVGFIV-PXCMFJNASA-N

物化性质

• 沸点：
  520.7±50.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  oleanene-(12)-diol-(3β.16α) 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 Manilladion
  参考文献：
  名称：

  有关三萜的知识。（第107部分）。在马尼拉二醇中第二个羟基的位置

  摘要：

  DOI：

  10.1002/hlca.19460290527
• 作为产物：
  描述：

  3β.16α-diacetoxy-oleanen-(12)-al-(28) 在 sodium ethanolate 、 一水合肼 作用下， 生成 报春花甙元 、 oleanene-(12)-diol-(3β.16α)
  参考文献：
  名称：

  Maintaining Gut Integrity During Parenteral Nutrition of Tumor-Bearing Rats: Effects of Glucagon-Like Peptide 2

  摘要：

  Maintaining tumor-bearing rats on total parenteral nutrition (TPN)for eight days significantly reduced mass, protein, and DNA in small intestine and colon. Coinfusion of glucagon-like peptide 2 (GLP-2) significantly increased each of these variables in the duodenum, jejunum, and ileum, but not in the colon. Histological analysis of tissue revealed normal mucosa thickness and villus height in the small intestine of GLP-2-treated rats, whereas nontreated rats maintained on TPN exhibited villus shortening and thinning of the mucosa. Compared with TPN alone, no significant effects of GLP-2 were noted on tumor growth, liver weight, or heart weight. Coinfusion of GLP-2 with TPN had no significant effect on TPN-associated immunosuppression, as measured by mitogen-induced proliferation of cultured splenocytes. Although translocation of bacteria to the mesenteric lymph nodes appeared to be reduced in GLP-2-treated vats, the difference between groups was not statistically significant. These results suggest that hormonal alterations may be more important than an absence of luminal nutrition in TPN-associated mucosa changes in tumor-bearing rats. Additionally, maintenance of gut integrity during TPN does not appear to be a sufficient condition for the avoidance of the negative sequelae associated with this route of supplemental nutrition.

  DOI：

  10.1207/s15327914nc372_15

文献信息

• Unraveling the Triterpenoid Saponin Biosynthesis of the African Shrub Maesa lanceolata
  作者：Tessa Moses、Jacob Pollier、Ahmad Faizal、Sandra Apers、Luc Pieters、Johan M. Thevelein、Danny Geelen、Alain Goossens

  DOI：10.1016/j.molp.2014.11.004

  日期：2015.1

  Maesasaponins produced by the African shrub Maesa lanceolata are oleanane-type saponins with diverse biological activities. Through a combination of transcript profiling of methyl jasmonate-elicited M. lanceolata shoot cultures, functional analysis in transgenic M. lanceolata plants and the heterologous hosts Medicago truncatula and Saccharomyces cerevisiae, we identified three maesaponin biosynthesis

  非洲灌木生产Maesasaponins湄沙杉木是齐墩果烷型皂甙具有多种生物学活性。通过转录谱描述茉莉酸甲酯诱发的组合M.杉木苗培养，在转基因功能分析M.杉木植物和异源宿主蒺藜苜蓿和酿酒酵母中，我们确定了三个maesaponin生物合成基因。其中包括一个β-淀粉酶合成酶和两个细胞色素P450 CYP716A75和CYP87D16，它们分别催化β-淀粉酶的C-28和C-16α氧化。
• Combinatorial biosynthesis of sapogenins and saponins in <i>Saccharomyces cerevisiae</i> using a C-16α hydroxylase from <i>Bupleurum falcatum</i>
  作者：Tessa Moses、Jacob Pollier、Lorena Almagro、Dieter Buyst、Marc Van Montagu、María A. Pedreño、José C. Martins、Johan M. Thevelein、Alain Goossens

  DOI：10.1073/pnas.1323369111

  日期：2014.1.28

  Saponins are plant molecules that are produced as a chemical defense against herbivores and eukaryotic pathogens. They constitute structurally diverse, bioactive compounds composed of a 30-carbon triterpene backbone adorned with multiple functional groups and sugars. Saikosaponins are abundant saponins accumulating in the Asian medicinal plant Bupleurum falcatum , but none of the enzymes involved in their biosynthesis had been characterized. We identified a cytochrome P450 involved in the oxidation of saikosaponins, thereby expanding the enzyme compendium that can generate plant saponins with an extra activity. Using this enzyme compendium, we established a synthetic biology program to reconstitute saponin biosynthesis in the yeast Saccharomyces cerevisiae and developed a cyclodextrin-based culturing strategy to sequester triterpenes from engineered yeast cells and enhance their productivity.

  皂苷是植物分子，作为对草食动物和真核病原体的化学防御而产生。它们由一个含有多个功能基团和糖的30碳三萜骨架构成的结构多样、生物活性化合物。赤芍皂苷是积累在亚洲药用植物斜刺蒿中的丰富皂苷，但是其生物合成过程中涉及的酶尚未被表征。我们鉴定了一种细胞色素P450参与赤芍皂苷的氧化反应，从而扩展了能够产生植物皂苷的酶的组合。利用这个酶组合，我们建立了一个合成生物学计划，在酵母菌中重构皂苷生物合成，并开发了一种基于环糊精的培养策略，从工程酵母细胞中分离三萜类化合物并增强其产量。