3β,23,28-trihydroxy-olean-12-ene | 35043-82-4

• 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: 3β,23,28-trihydroxy-olean-12-ene
• 英文别名: 18beta-Olean-12-ene-3beta-23,28-triol；(3S,4R,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-ol
• CAS: 35043-82-4
• 化学式: C₃₀H₅₀O₃
• 分子量: 458.725
• InChiKey: GGJRJQAJVMFZIP-ODAROHGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β,23,28-trihydroxy-olean-12-ene 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 3β,23,28-trihydroxyolean-11,13(18)-diene
  参考文献：
  名称：

  The Chemical Studies on Oriental Plant Drugs. XV. On the Constituents of Bupleurum Spp. (2). The Structure of Saikogenin A, a Sapogenin of Bupleurum falcatum L.

  摘要：

  一种被提议命名为赛可根素A的皂苷元，已从柴胡（Bupleurum falcatum L，业名：Mishimasaiko）的皂苷中获得。本研究为赛可根素A提供了结构式（I）。

  DOI：

  10.1248/cpb.14.1023
• 作为产物：
  描述：

  常春藤皂苷元 生成 3β,23,28-trihydroxy-olean-12-ene
  参考文献：
  名称：

  The Chemical Studies on Oriental Plant Drugs. XV. On the Constituents of Bupleurum Spp. (2). The Structure of Saikogenin A, a Sapogenin of Bupleurum falcatum L.

  摘要：

  一种被提议命名为赛可根素A的皂苷元，已从柴胡（Bupleurum falcatum L，业名：Mishimasaiko）的皂苷中获得。本研究为赛可根素A提供了结构式（I）。

  DOI：

  10.1248/cpb.14.1023

文献信息

• Semi-synthesis and Structure-Activity Relationship of Neuritogenic Oleanene Derivatives
  作者：Linglin Bian、Shining Cao、Lihong Cheng、Atsuo Nakazaki、Toshio Nishikawa、Jianhua Qi

  DOI：10.1002/cmdc.201800352

  日期：2018.9.19

  the structure and to assess biological activity, we semi‐synthesized 1 a from commercially available oleanolic acid. A series of novel 1 a derivatives was then designed and synthesized for a structure–activity relationship (SAR) study. All synthetic derivatives were characterized by analysis of spectral data, and their neuritogenic activities were evaluated in assays with PC12 cells. The SAR results

  从（3 S，4 R）-23,28-Dihydroxyolean-12-en-3-yl（2 E）-3-（3,4-dihydroxyphenyl）丙烯酸酯（1 a）中分离出具有显着神经形成活性的传统中草药（Desmodium sambuense）植物。为了确定结构并评估生物活性，我们从市售齐墩果酸中半合成了1 a。小说系列1a然后设计并合成衍生物，以进行结构-活性关系（SAR）研究。所有合成衍生物均通过光谱数据分析进行表征，并在PC12细胞测定中评估了它们的神经生成活性。SAR结果表明，苯环和三萜烯部分上羟基的数量和位置，以及将苯环与三萜烯连接的（饱和或不饱和）烷基链的长度严重影响了神经形成活性。在所有测试的化合物中，发现了1 e [（3 S，4 R）-23,28-dihydroxyolean-12-en-3-yl（2 E）-3-（3,4,5-三羟基苯基）丙烯酸酯]最有效，可在1μm处引起明显的神经突生长。
• Tritepenoid chemistry. VII. Classification of triterpenoid 1,3-glycol acetonides by NMR spectra.
  作者：YOSHISUKE TSUDA、TAKEHIRO SANO、KIMIAKI ISOBE、MUNEYO MIYAUCHI

  DOI：10.1248/cpb.22.2396

  日期：——

  Triterpenoid glycols carrying hydroxy-groups at C3 and at one of 4, 4-dimethyl groups were converted to the corresponding acetonides (A-D), whose characterization by nuclear magnetic resonance spectroscopy were discussed in connection with their stereochemical properties, and a reliable method to determine their stereochemistry was presented. The stabilities of these acetonides to hydrolytic cleavage were also discussed. The conformation of the monoacetonide (16) derived from platicodigenin was suggested to be as 16b.

  通过核磁共振光谱分析，讨论了三萜类乙二醇的特征及其立体化学性质，并提出了确定其立体化学性质的可靠方法。此外，还讨论了这些丙酮对水解裂解的稳定性。结果表明，由 platicodigenin 衍生的单丙酮(16)的构象为 16b。
• Triterpenoid saponins from Dianthus chinensis
  作者：Kazuo Koike、Hongyu Li、Zhonghua Jia、Hitomi Muraoka、Satoko Fukui、Masako Inoue、Taichi Ohmoto

  DOI：10.1016/s0040-4020(01)81202-3

  日期：1994.1

  Four novel triterpenoid saponins, dianchinenosides E, F, G and H have been isolated from the aerial parts of Dianthus chinensis L. Dianchinenosides E and F, G and H are diastereomers with the only difference being in the stereochemistry of the 1,2-propanediol residues esterified to the C-23 of their aglycones. Their structures including the absolute configuration of the 1,2-propanediol fragments were

  从石竹的地上部分中分离出了四个新颖的​​三萜皂苷，双酚A，E，F，G和H。双酚A，E，F，G和H是非对映异构体，唯一的区别在于1,2-丙二醇的立体化学残基被酯化为糖苷配基的C-23。通过光谱和化学证据以及手性HPLC分析确定了它们的结构，包括1,2-丙二醇片段的绝对构型。
• Triterpenoid chemistry. III. Stereospecific reactions of triterpenoid 1,3-glycol monotoslyates and ketotosylates.
  作者：YOSHISUKE TSUDA、KIMIAKI ISOBE、TAKEHIRO SANO、AKIRA MORIMOTO

  DOI：10.1248/cpb.23.98

  日期：——

  The reactions of 1, 3-glycol monotosylates of the configurations A-D with base and LAH were discussed. On reaction with t-butoxide, A and D (cis relationship between-OH and -CH2OTs) gave oxetanes E and F respectively, while B and C (trans relationship between these groups) gave the same seco-aldehyde G. On LAH reduction, in addition to the above reaction (oxetane formation from A and D, seco-alcohol formation from B and C), two further reactions took place ; a) S-O fission (formation of the glycols A-D), and b) C-O fission (formation of the deoxy-compounds H and I), for the latter reaction the cyclic intermediate (K-M) were proposed. The monotosylate of B did not give deoxy-compound. The corresponding keto-tosylate (N and O), when treated with lithium aluminum hydride firstly gave 3β-alcohols (A and C) which are further reduced as above ; the fact which therefore opened a way to yield deoxy-compound (I) from type B glycol (B→N→I).

  讨论了构型为 A-D 的 1，3-乙二醇单甲苯磺酸盐与碱和 LAH 的反应。与叔丁醇反应时，A 和 D（OH 和 -CH2OT 之间的顺式关系）分别生成氧杂环丁烷 E 和 F，而 B 和 C（这些基团之间的反式关系）生成相同的仲醛 G。在 LAH 还原过程中，除了上述反应（由 A 和 D 生成氧杂环丁烷，由 B 和 C 生成仲醇）外，还发生了两个反应：a）S-O 裂变（生成乙二醇 A-D）；b）C-O 裂变（生成脱氧化合物 H 和 I）。B 的单甲苯磺酸盐没有生成脱氧化合物。相应的酮基对甲苯磺酸盐（N 和 O）用氢化铝锂处理后，首先生成 3β 醇（A 和 C），然后再按上述方法进一步还原；因此，这为从 B 型乙二醇（B→N→I）中生成脱氧化合物（I）开辟了道路。
• Yoshikawa, Masayuki; Wang, Hui Kang; Tosirisuk, Veeraphan, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 8, p. 3057 - 3060
  作者：Yoshikawa, Masayuki、Wang, Hui Kang、Tosirisuk, Veeraphan、Kitagawa, Isao

  DOI：——

  日期：——