[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (1S,2R,4aS,6aR,6aR,6bR,8R,8aR,9R,10R,11R,12aR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate | 34540-22-2

• 物质功能分类: 生物化工 - 提取物
• 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: [(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (1S,2R,4aS,6aR,6aR,6bR,8R,8aR,9R,10R,11R,12aR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate
• CAS: 34540-22-2
• 化学式: C₄₈H₇₈O₂₀
• mdl: MFCD00017380
• 分子量: 975.1
• InChiKey: BNMGUJRJUUDLHW-CIZDPPTDSA-N

物化性质

• 熔点：
  220-223 °C
• 沸点：
  1043.6±65.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)
• 溶解度：
  水中的溶解度为1mg/mL，透明，无色
• LogP：
  -1.338 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  68
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.937
• 拓扑面积：
  335
• 氢给体数：
  13
• 氢受体数：
  20

安全信息

• WGK Germany：
  3
• RTECS号：
  YU9625000
• 海关编码：
  29389090

制备方法与用途

生物活性

Madecassoside (Asiaticoside A) 是积雪草草药的主要活性三萜烯成分。积雪草是一种传统中药，用于治疗创伤修复和疤痕管理。

靶点

• 人类内源性代谢物

化学性质：白色结晶粉末，溶于甲醇，来源于积雪草。

用途

羟基积雪草苷具有多种功效，包括抗抑郁症、防治烧伤性瘢痕、抗癌、预防冠心病和心肌梗死、脑血栓及脑梗塞、增强记忆、皮肤美白等。

此外，它还可用于含量测定、鉴定以及药理实验等。药理作用适用于治疗抑郁症、烧伤性瘢痕、癌症预防、冠心病和心肌梗死的防治、脑血栓与脑梗塞的处理、提高记忆力及皮肤美白等方面。

反应信息

• 作为反应物：
  描述：

  、 [(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (1S,2R,4aS,6aR,6aR,6bR,8R,8aR,9R,10R,11R,12aR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate 在 乙醇 作用下， 以 [(2S,4S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8R,8aR,9R,10R,11R,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-carboxylate 为溶剂， 生成 Asiaticoside
  参考文献：
  名称：

  Method for preparing a Centella asiatica extract rich in madecassoside and in terminoloside

  摘要：

  该发明涉及一种包含超过75重量％的积雪草提取物，相对于提取物总重量，该提取物包含madecassoside，terminoloside和asiaticoside的混合物，以及一种包含超过95重量％的积雪草提取物，相对于提取物总重量，该提取物包含madecassoside和terminoloside的混合物，以及它们用于调节炎症机制。

  公开号：

  US08486900B2

文献信息

• Method for preparing a centella asiatica extract rich in madecassoside and in terminoloside
  申请人：Loiseau Alain

  公开号：US20060106206A1

  公开（公告）日：2006-05-18

  The invention concerns a method for preparing an extract comprising a mixture of madecassoside, terminoloside and optionally asiaticoside, an extract of Centella asiatica comprising more than 75 wt % of a mixture of madecassoside, terminoloside and asiaticoside, relative to the extract total weight, an extract of Centella asiatica comprising more than 95 wt. % of a mixture of madecassoside and terminoloside relative to the extract total weight and their use for regulating inflammatory mechanisms.

  该发明涉及一种制备提取物的方法，包括一个混合物，其中包括积雪草苷、终端苷和可选的积雪草苷，一种积雪草提取物，其中包括相对于提取物的总重量超过75重量％的积雪草苷、终端苷和积雪草苷的混合物，一种积雪草提取物，其中包括相对于提取物的总重量超过95重量％的积雪草苷和终端苷的混合物，并且它们用于调节炎症机制。
• Water-soluble extract of asiaticoside and madecassoside from Centella asiatica and isolating method thereof
  申请人：——

  公开号：US06417349B1

  公开（公告）日：2002-07-09

  A water-soluble extract of asiaticoside and madecassoside from Centella asiatica and an isolating method thereof. In the isolating method an aqueous alcohol containing Centella asiatica is subjected to cold-precipitation to obtain an extract. The extract in the aqueous alcohol is treated with a halogenide solvent for layer separation, and then the aqueous layer is extracted with a higher alcohol. The extract in the alcohol layer is washed first with sodium hydroxide and then with water. After being concentrated, the extract is crystallized with ethyl acetate to obtain crystals and the crystals are washed. A method for treating liver cells in a mammal includes administering to a mammal an effective amount of the extract from Centella asiatica containing asiaticoside and madecassoside.

  一种从积雪草提取的具有水溶性的asiaticoside和madecassoside的提取物以及其分离方法。在分离方法中，将含有积雪草的水醇溶液进行冷沉淀以获得提取物。将水醇中的提取物用卤化物溶剂进行层分离，然后用高级醇提取水层。醇层中的提取物首先用氢氧化钠洗涤，然后用水洗涤。浓缩后，用乙酸乙酯结晶提取物以获得晶体并对晶体进行洗涤。一种用于治疗哺乳动物肝细胞的方法包括向哺乳动物投与含有asiaticoside和madecassoside的积雪草提取物的有效量。
• METHOD FOR PREPARING A CENTELLA ASIATICA EXTRACT RICH IN MADECASSOSIDE AND IN TERMINOLOSIDE
  申请人：Loiseau Alain

  公开号：US20120178706A1

  公开（公告）日：2012-07-12

  The invention concerns an extract of Centella asiatica comprising more than 75 wt. % of a mixture of madecassoside, terminoloside and asiaticoside, relative to the extract total weight, an extract of Centella asiatica comprising more than 95 wt. % of a mixture of madecassoside and terminoloside relative to the extract total weight and their use for regulating inflammatory mechanisms.

  本发明涉及一种以积雪草提取物为基础的混合物，其包含相对于提取物总重量超过75重量％的积雪草苷、终端苷和穿心莲苷的混合物，以及相对于提取物总重量超过95重量％的积雪草苷和终端苷的混合物，并且它们用于调节炎症机制。
• Method for preparing a Centella asiatica extract rich in madecassoside and in terminoloside
  申请人：Bayer Consumer Care AG

  公开号：US07402669B2

  公开（公告）日：2008-07-22

  The invention concerns a method for preparing an extract comprising a mixture of madecassoside, terminoloside and optionally asiaticoside, an extract of Centella asiatica comprising more than 75 wt % of a mixture of madecassoside, terminoloside and asiaticoside, relative to the extract total weight, an extract of Centella asiatica comprising more than 95 wt. % of a mixture of madecassoside and terminoloside relative to the extract total weight and their use for regulating inflammatory mechanisms.

  该发明涉及一种制备提取物的方法，该提取物包括一种混合物，其中包括madecassoside、terminoloside和可选的asiaticoside。一种Centella asiatica提取物，相对于提取物总重量，包括超过75重量％的madecassoside、terminoloside和asiaticoside混合物。一种Centella asiatica提取物，相对于提取物总重量，包括超过95重量％的madecassoside和terminoloside混合物。它们用于调节炎症机制。