(2beta,3beta,5Xi,6beta,18alpha)-2,3,6,23-四羟基齐墩果-12-烯-28-酸 | 37905-13-8

• 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
• 中文名称: (2beta,3beta,5Xi,6beta,18alpha)-2,3,6,23-四羟基齐墩果-12-烯-28-酸
• 英文名称: protobassic acid
• 英文别名: (4aS,6aR,6aS,6bR,8R,8aR,9R,10R,11S,12aR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 37905-13-8
• 化学式: C₃₀H₄₈O₆
• 分子量: 504.708
• InChiKey: IDQVFXZQPGAVAM-YPRSBIJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  118
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  12α-bromo-3-oxoolean-28β→13β olide 在 甲醇 、 sodium periodate 、 lithium aluminium tetrahydride 、 锂硼氢 、 四丙基高钌酸铵 、 ruthenium(III) chloride trihydrate 、 盐酸羟胺 、 碘 、 lead(IV) tetraacetate 、 4-甲基苯磺酸吡啶 、 乙酸酐 、 potassium carbonate 、 对甲苯磺酸 、 溶剂黄146 、 N-甲基吗啉氧化物 、 calcium carbonate 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 aq. phosphate buffer 、 水 、 丙酮 、 乙腈 、 苯 为溶剂， 反应 252.91h， 生成 (2beta,3beta,5Xi,6beta,18alpha)-2,3,6,23-四羟基齐墩果-12-烯-28-酸
  参考文献：
  名称：

  中继CH氧化逻辑在多羟基化的齐墩果三萜类化合物中的应用

  摘要：

  尽管由于不良的溶解度和生物利用度，丰富的原料三萜类化合物如齐墩果酸的临床应用受到限制，但合成获得更高羟基化的齐墩果萜烯类化合物仍然具有挑战性。我们现在报告使用中继CH氧化逻辑来模仿P450单加氧酶在自然界中进行的过程。为此，我们使用C-23-OH作为氢原子转移至C-6的天然手柄，从而实现了高度氧化的天然产物uncargenin C和原碱酸的首次合成，并揭示了其抗白血病活性合成中间体。

  DOI：

  10.1016/j.chempr.2020.04.007

文献信息

• ACCELERATOR FOR INITIAL INSULIN SECRETION
  申请人：Use-Techno Corporation

  公开号：EP1674089A1

  公开（公告）日：2006-06-28

  The present invention provides an early insulin secretion stimulator consisting of a triterpene represented by the following general formula (1) and/or a triterpene represented by the following general formula (2). [where R1 represents COOH, etc., R11 and R12 represent CH2OH, etc., X1 represents hydrogen or OH and X11, X12, X21 and X22 represent OH, etc.]

  本发明提供了一种早期胰岛素分泌刺激剂，由以下通式（1）代表的三萜和/或以下通式（2）代表的三萜组成。 [其中 R1 代表 COOH 等，R11 和 R12 代表 CH2OH 等，X1 代表氢或 OH，X11、X12、X21 和 X22 代表 OH 等。］
• Polynucleotide binding complexes comprising sterols and saponin
  申请人：Nordic Vaccine Technology A/S

  公开号：EP2011517A1

  公开（公告）日：2009-01-07

  The present invention pertains to complexes comprising sterols and saponins. The complexes are capable of binding a genetic determinant including a polynucleotide. The complexes may further comprise a lipophilic moiety, optionally a lipophilic moiety comprising a contacting group and/or a targeting ligand, and/or a saccharide moiety. The complexes may further comprise an immunogenic determinant and/or an antigenic determinant and/or a medicament and/or a diagnostic compound. The complexes may in even further embodiments be encapsulated by an encapsulation agent including a biodegradable microsphere. The present invention also pertains to pharmaceutical compositions and methods of treatment of an individual by therapy and/or surgery, methods of cosmetic treatment, and diagnostic methods practised on the human or animal body.

  本发明涉及由甾醇和皂甙组成的复合物。这些复合物能够结合包括多核苷酸在内的遗传决定因子。复合物可进一步包含亲脂分子，可选择包含接触基团和/或靶向配体的亲脂分子和/或糖分子。复合物可进一步包括免疫原决定簇和/或抗原决定簇和/或药物和/或诊断化合物。在更进一步的实施方案中，复合物可被包括生物可降解微球在内的封装剂封装。本发明还涉及通过治疗和/或手术对个体进行治疗的药物组合物和方法、美容治疗方法以及对人体或动物体进行诊断的方法。
• Triterpene glycosides and other polar constituents of shea (Vitellaria paradoxa) kernels and their bioactivities
  作者：Jie Zhang、Masahiro Kurita、Takuro Shinozaki、Motohiko Ukiya、Ken Yasukawa、Naoto Shimizu、Harukuni Tokuda、Eliot T. Masters、Momoko Akihisa、Toshihiro Akihisa

  DOI：10.1016/j.phytochem.2014.09.017

  日期：2014.12

  The MeOH extract of defatted shea (Vitellaria paradoxa; Sapotaceae) kernels was investigated for its constituents, and fifteen oleanane-type triterpene acids and glycosides, two steroid glucosides, two pentane-2,4-diol glucosides, seven phenolic compounds, and three sugars, were isolated. The structures of five triterpene glycosides were elucidated on the basis of spectroscopic and chemical methods. Upon evaluation of the bioactivity of the isolated compounds, it was found that some or most of the compounds have potent or moderate inhibitory activities against the following: melanogenesis in B16 melanoma cells induced by alpha-melanocyte-stimulating hormone (alpha-MSH); generation of 1,1-dipheny1-2-picrylhydrazyl (DPPH) radicals, against Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-teradecanoylphorbol 13-acetate (TPA) in Rail cells; t TPA-induced inflammation in mice, and proliferation of one or more of HL-60, A549, AZ521, and SK-BR-3 human cancer cell lines, respectively. Western blot analysis established that paradoxoside E inhibits melanogenesis by regulation of expression of microphthalmia-associated transcription factor (MITF), tyrosinase, and tyrosinase-related protein-1 (TRP-1) and TRP-2. In addition, tieghemelin A was demonstrated to exhibit cytotoxic activity against A549 cells (IC50 13.5 mu M) mainly due to induction of apoptosis by flow cytometry. The extract of defatted shea kernels and its constituents may be, therefore, valuable as potential antioxidant, anti-inflammatory, skin-whitening, chemopreventive, and anticancer agents. (c) 2014 Elsevier Ltd. All rights reserved.
• POLYNUCLEOTIDE BINDING COMPLEXES COMPRISING STEROLS AND SAPONINS
  申请人：Nordic Vaccine Technology A/S

  公开号：EP1377320B1

  公开（公告）日：2008-10-01
• THERAPEUTICAL VACCINATION
  申请人：Nordic Vaccine Technology A/S

  公开号：EP1409009A1

  公开（公告）日：2004-04-21