贝萼皂苷元甲酯 | 22425-81-6

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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
• 中文名称: 贝萼皂苷元甲酯
• 英文名称: bayogenin methyl ester
• 英文别名: methyl (4aS,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bS)-10,11-dihydroxy-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-carboxylate
• CAS: 22425-81-6
• 化学式: C₃₁H₅₀O₅
• 分子量: 502.735
• InChiKey: PQQIABJSQBQEFM-VITDCEDBSA-N

物化性质

• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  贝萼皂苷元甲酯 在 lithium aluminium tetrahydride 作用下， 生成 Δ¹²-Oleanen-2β,3β,23,28-tetrol
  参考文献：
  名称：

  Eade,R.A. et al., Australian Journal of Chemistry, 1963, vol. 16, p. 900 - 905

  摘要：

  DOI：
• 作为产物：
  描述：

  Methyl 2β,3β-diacetoxy-23α-acetoxymethyl-Δ¹²-oleanene-28β-carboxylate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 贝萼皂苷元甲酯
  参考文献：
  名称：

  药用酸皂苷的合成及其对植物病原体的抗真菌活性：糖部分的修饰和23α取代。

  摘要：

  药用酸皂苷的结构-抗真菌活性关系的研究范围扩大到包括甘露糖，半乳糖，纤维二糖和乳糖的合成糖苷以及药用酸的23α-羟甲基类似物，即甲基2β，3β-二羟基-23-α-羟甲基-δ（12）-亚麻烯-28β-羧酸盐，对小核盘菌，茄状枯萎病菌，里氏木霉，黑曲霉和尖孢镰刀菌具有抗性。除了含纤维二糖的衍生物和尖孢镰刀菌外，含天然葡萄糖的皂苷比上述皂苷是更有效的抗真菌剂。皂苷元的23α位上的羧基取代基比羧酸甲酯具有更高的抑菌活性，而羧酸甲酯反过来比相同位置上的羟甲基更有效。

  DOI：

  10.1016/0008-6215(93)80012-4

文献信息

• Phenolic and triterpenoid glycosides from Aster batangensis
  作者：Yu Shao、Yun Long Li、Bing Nan Zhou

  DOI：10.1016/0031-9422(95)00219-7

  日期：1996.4

  A new phenolic glycoside, asterbatanoside A [p-hydroxyacetophenone-4-O-beta-D-xylopyranosyl-(1-->6)-beta-D- glucopyranoside], and two new triterpenoid saponins, asterbatanoside B [2 alpha,3 beta,23-trihydroxyolean-12-en-28-oic acid-28-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside] and asterbatanoside C [3-O-beta-D-glucopyranosyl-2 beta,3 beta,23-trihydroxyolean- 12-en-28-oic acid-28-O-bet

  一种新的酚糖苷，asterbatanoside A [p-hydroxyacetophenone-4-O-beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside]，和两种新的三萜皂苷，asterbatanoside B [2 alpha,3 beta,23-trihydroxyolean-12-en-28-oic acid-28-O-beta-D-glupyranosyl-(1-->6)-beta-D-glucopyranoside] 和 asterbatanoside C [3-O-beta-D -glupyranosyl-2 beta,3 beta,23-trihydroxyolean-12-en-28-oic acid-28-O-beta-D-glucopyranoside] 是从 Aster batangensis 的根中分离出来的。
• Triterpenoid saponins from Aster batangensis
  作者：Yu Shao、Bing-Nan Zhou、Long-Ze Lin、Geoffrey A. Cordell

  DOI：10.1016/0031-9422(94)00744-e

  日期：1995.3

  Four novel triterpenoid saponins named asterbatanoside F, G, H and I were isolated from the roots of Aster batangensis and their structures elucidated as 3-O-beta-D-glucopyranosyl-23-O-acetyl-bayogenin-28-O-beta-D-glu cop yranosyl- (1-->6)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-glucopyranoside, 3-O-beta-D-glucopyranosyl-bayogenin-28-O-beta-D-glucopyranosyl-(1- ->6)-[alpha-f1p4amnopyranosyl-(1-->

  从八角紫菀根中分离出四种名为asterbatanoside F、G、H和I的新型三萜皂苷，其结构被阐明为3-O-β-D-吡喃葡萄糖基-23-O-乙酰基-bayogenin-28-O-β- D-glu cop yranosyl-(1-->6)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-glucopyranoside, 3-O-beta-D-glupyranosyl-bayogenin-28- O-β-D-吡喃葡萄糖基-(1-->6)-[α-f1p4amnopyranosyl-(1-->2)]-β-D-吡喃葡萄糖苷，3-O-β-D-吡喃葡萄糖基-(1-- >3)-β-D-吡喃葡萄糖基-bayogenin-28-O-β-D-吡喃葡萄糖基-(1-->6)-β-D-吡喃葡萄糖苷和3-O-β-D-吡喃葡萄糖基-(1- ->3)-β-D-吡喃葡萄糖基-23-O-乙
• New Triterpenic Saponins from the Aerial Parts of <i>Medicago arabica</i> (L.) Huds
  作者：Aldo Tava、Mariella Mella、Pinarosa Avato、Elisa Biazzi、Luciano Pecetti、Zbigniew Bialy、Marian Jurzysta

  DOI：10.1021/jf8036984

  日期：2009.4.8

  The reinvestigation of saponin composition from Medicago arabica from Italy allowed the detection of nineteen (1-19) saponins. All of them were purified by reverse-phase chromatography and their structures elucidated by spectroscopic and spectrometric (1D and 2D NMR; ESI-MS/MS) and chemical methods. Fourteen were known saponins, previously found in other plants including other Medicago, species. They have been identified as glycosides of oleanolic acid, 2 beta,3 beta-dihydroxyolean-12-en-28-oic acid, hederagenin, bayogenin and soyasapogenol B. Five saponins, identified as 3-O-[-alpha-L-arabinopyranosyl(1 -> 2)-beta-D-glucuronopyranosyl]-30-O-beta-D-glucopyranosyl 2 beta,3 beta,30-trihydroxyolean-12-en-28-oic acid (1), 3-O-[alpha-L-arabinopyranosyl(1 -> 2)-beta- -D-glucuronopyranosyl]-30-O-[beta-D-glucopyranosyl]3 beta,30-dihydroxyolean-12-en-28-oic acid (2), 3-O-[beta-D-glucuronopyranosyl]-30-O-[alpha-L-arabinopyranosyl(1 -> 2)-beta-D-glucopyranosyl]2 beta,3 beta,30-trihydroxyolean-12-en-28-oic acid (3), 3-O-[beta-D-glucuronopyranosyl]-30-O[alpha-L-arabinopyranosyl(1 -> 2)-beta-D-glucopyranosyl] 3 beta,30-dihydroxyolean-12-en-28-oic acid (4) and 3-O-[beta-D-glucuronopyranosyl]-30-O-[beta-D-glucopyranosyl] 2 beta,3 beta,30-trihydroxyolean-12-en-28-oic acid (5), are reported here as new natural compounds. These new saponins, possessing a hydroxy group at the 30-methyl position of the triterpenic skeleton, have never been previously found in the genus Medicago.
• Triterpenoid saponins from leaves of Castanospermum australe
  作者：Viqar Uddin Ahmad、Waseemuddin Ahmed、Khan Usmanghani

  DOI：10.1016/0031-9422(92)83635-c

  日期：1992.8