soyasapogenol B | 595-15-3

• 物质功能分类: 天然产物 - 萜类
• 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: soyasapogenol B
• 英文别名: (3S,4S,6aR,6bS,8aR,9R,14bR)-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,9-diol
• CAS: 595-15-3；124862-79-9
• 化学式: C₃₀H₅₀O₃
• 分子量: 458.725
• InChiKey: YOQAQNKGFOLRGT-FNBSVUNXSA-N

物化性质

• 熔点：
  258～259℃
• 沸点：
  555.5±50.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  33
• 可旋转键数：
  1
• 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

安全信息

• WGK Germany：
  3

制备方法与用途

生物活性方面，大豆成分之一的Soyasapogenol B 具有抗增殖和抗转移活性。它能够触发内质网应激反应，并在结肠直肠癌中诱导细胞凋亡和自噬过程。

反应信息

• 作为反应物：
  描述：

  甲醇 、 soyasapogenol B 在 盐酸 作用下， 生成 (3S,4S,4aR,6aR,6bS,8aR,9R,14aR,14bR)-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,13,14,14a-tetradecahydropicene-3,9-diol 、 soyasapogenol D
  参考文献：
  名称：

  紫花苜蓿的三萜皂苷

  摘要：

  大豆皂苷 III 已被表征，一种新的三萜皂苷，hipidacin 的结构已被阐明为大豆皂醇 B-3-O-α-L-rhamnopyranopyranosyl(1----2)-beta-D-glupyranosyl(1-- --2)-β-D-吡喃葡萄糖苷通过快速原子轰击质谱、13C NMR 光谱和一些化学转化的组合。大豆皂醇 B 转化为大豆皂醇 D 和 F 的机制也得到了合理化。

  DOI：

  10.1016/0031-9422(91)83215-7
• 作为产物：
  描述：

  (2S,3S,4S,5R,6R)-6-[[(4S,6aR,6bS,8aR,9R,14bR)-9-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,12,14,14a-dodecahydro-1H-picen-12a-yl]oxy]-3-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxyoxane-2-carboxylic acid 生成 soyasapogenol B
  参考文献：
  名称：

  SUN, RONG-QI;CHENG, DONG-LIANG;JIA, ZHONG-JIAN;ZHU, ZI-QING(CHU TSE-TSIN), ACTA CHIM. SIN., 45,(1987) N 2, 145-149

  摘要：

  DOI：

文献信息

• Means and methods for regulating secondary metabolite production in plants
  申请人：VIB VZW

  公开号：US11208667B2

  公开（公告）日：2021-12-28

  This disclosure relates to the field of secondary metabolite production in plants. More specifically, the disclosure relates to chimeric genes encoding a bHLH protein of subfamily Iva comprising a bHLH domain and their use in the regulation of biosynthesis and/or production of secondary metabolites in plants and plant-derived cell cultures.

  本公开涉及植物次生代谢产物的生产领域。更具体地说，本公开涉及编码包含一个 bHLH 结构域的 Iva 亚族 bHLH 蛋白的嵌合基因及其在调节植物和植物衍生细胞培养物中次生代谢物的生物合成和/或生产中的用途。
• SUN, RONG-QI;CHENG, DONG-LIANG;JIA, ZHONG-JIAN;ZHU, ZI-QING(CHU TSE-TSIN), ACTA CHIM. SIN., 45,(1987) N 2, 145-149
  作者：SUN, RONG-QI、CHENG, DONG-LIANG、JIA, ZHONG-JIAN、ZHU, ZI-QING(CHU TSE-TSIN)

  DOI：——

  日期：——
• C-22 HYDROXYLASE
  申请人：Ebizuka Yutaka

  公开号：US20110171698A1

  公开（公告）日：2011-07-14

  β-Amyrin, a precursor in biosynthesis of soyasapogenol B, is biosynthesized by cyclization of 2,3-oxidosqualene which is generated by the mevalonate pathway, and soyasapogenol B is biosynthesized by two hydroxylations of β-amyrin. However, a gene of 22-hydroxylase involved in the sequence of reactions has not been identified. The present inventors identified a gene encoding the hydroxylase for oleanene triterpenes at C-22, and found that oleanene triterpenes could be hydroxylated at C-22 by co-expressing this gene together with one or more specific genes. Further, the present inventors found that soyasapogenol B could be efficiently produced in large quantities by co-expressing this gene for 22-hydroxylase with a gene for 24-hydroxylase.
• Means and Methods for Regulating Secondary Metabolite Production in Plants
  申请人：VIB VZW

  公开号：US20190071686A1

  公开（公告）日：2019-03-07

  This disclosure relates to the field of secondary metabolite production in plants. More specifically, the disclosure relates to chimeric genes and their use in the regulation of biosynthesis and/or production of secondary metabolites in plants and plant-derived cell cultures.
• CELLULOSE-SYNTHASE-LIKE ENZYMES AND USES THEREOF
  申请人：YEDA RESEARCH AND DEVELOPMENT CO. LTD.

  公开号：US20220217934A1

  公开（公告）日：2022-07-14

  Provided herein are genetically modified cells and genetically modified plants having increased or decreased expression of a cellulose synthase like G (CSLG) enzyme. These cells and plants may have an increased or decreased content a steroidal alkaloid, a steroidal saponin, or a triterpenoid saponin, compared to a corresponding unmodified cell or plant. Also provided herein are methods of producing a steroidal alkaloid, a steroidal saponin, or a triterpenoid saponin in a genetically modified cell, as well as methods of reducing the content of a steroidal alkaloid, a steroidal saponin, or a triterpenoid saponin in a cell of a plant or a plant part, and methods of increasing the content of a steroidal alkaloid, a steroidal saponin, or a triterpenoid saponin in a cell of a plant or a plant part.