地肤子皂苷 Ic | 96990-18-0

• 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
• 中文名称: 地肤子皂苷 Ic
• 中文别名: 地肤子皂苷；地肤子皂苷Ic；地肤子皂苷ⅠC
• 英文名称: (3β)-17-carboxy-28-norolean-12-en-3-yl 3'-O-(β-D-xylopyranosyl)-β-D-glucuronide
• 英文别名: oleanolic acid 3-O-monodesmoside；momordin Ic；momordin lc；momordinic；oleanolic acid-3-O-β-D-xylopyranose(1–3)-β-D-pyranoid glucose；(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid
• CAS: 96990-18-0
• 化学式: C₄₁H₆₄O₁₃
• 分子量: 764.951
• InChiKey: HWYBGIDROCYPOE-WEAQAMGWSA-N

物化性质

• 熔点：
  238-240 °C
• 沸点：
  886.2±65.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)
• 溶解度：
  加热、超声处理轻微溶于甲醇、微溶于吡啶

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  54
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  213
• 氢给体数：
  7
• 氢受体数：
  13

安全信息

• WGK Germany：
  3

制备方法与用途

生物活性

Momordin Ic 是山茱萸的主要皂苷成分，具有抗癌活性。它通过调节氧化应激和线粒体功能障碍来诱导细胞凋亡。

化学性质

Momordin Ic 为浅黄色结晶粉末，溶于甲醇，来源于地肤子。

用途

地肤子皂苷Ic（Momordin Ic）具有清热利湿、祛风止痒等功效，并且具备抗瘙痒、抗炎和抗过敏的作用。此外，它还用于含量测定、鉴定以及药理实验等。

药理药效

地肤子皂苷Ic (Momordin Ic) 是其主要有效成分之一，具有清热利湿、祛风止痒等功效，并且发挥着显著的抗瘙痒、抗炎和抗过敏作用。

反应信息

• 作为反应物：
  描述：

  地肤子皂苷 Ic 在 盐酸 作用下， 以32 mg的产率得到金盏花苷E
  参考文献：
  名称：

  Talinum tenuissimum DINTER的杀菌杀虫皂苷† ‡

  摘要：

  两个新的皂甙，β-d-D-吡喃葡萄糖基的3- ö [ ö -βD-xylopyranosyl-（13）-O-（β-d吡喃葡萄糖醛酸）] oleanolate（1）和3- ö - [ ö -β-D-从塔利木的块茎中分离出木吡喃糖基-（13）-O-（β-D-吡喃葡糖基糖醛酸）]油酸（2）。主要通过13 C-NMR和FAB-MS建立了结构。单糖苷皂苷2对血吸虫病传播的蜗牛Biomphalaria glabrata表现出非常强的杀软体动物活性。

  DOI：

  10.1002/hlca.19850680303
• 作为产物：
  描述：

  (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid 、 sodium hydroxide 、 水 生成 地肤子皂苷 Ic
  参考文献：
  名称：

  MA, W. -W.;HEINSTEIN, P. F.;MCLAUGHLIN, J. L., J. NATUR. PROD., 52,(1989) N, C. 1132-1135

  摘要：

  DOI：

文献信息

• Triterpenoid Glycosides from the Fruits of<i>Kochia scoparia</i>
  作者：Ye Wen、Yingjie Chen、Zhiping Cui、Jiahe Li、Zhixue Wang

  DOI：10.1055/s-2006-958134

  日期：1995.10

  From the fruits of Kochia scoparia (L.) Schrad, five triterpenoid glycosides were isolated for the first time from this plant. They were elucidated as momordin Ic, the 6′-methyl ester of momordin IIc, momordin He, 2′-O-β-D-glucopyranosylmomordin Ic, and 2′-O-β-D-glucopyranosylmomordin IIc on the basis of spectral and chemical methods. The last two saponins are new natural products.

  首次从 Kochia scoparia (L.) Schrad 的果实中分离出五种三萜类苷。根据光谱和化学方法，它们被确定为莫莫丁 Ic、莫莫丁 IIc 的 6′-甲基酯、莫莫丁 He、2′-O-δ²-D-吡喃葡萄糖基莫莫丁 Ic 和 2′-O-δ²-D-吡喃葡萄糖基莫莫丁 IIc。后两种皂甙是新的天然产物。
• Antidiabetic Principles of Natural Medicines. III. Structure-Related Inhibitory Activity and Action Mode of Oleanolic Acid Glycosides on Hypoglycemic Activity.
  作者：Hisashi MATSUDA、Yuhao LI、Toshiyuki MURAKAMI、Narumi MATSUMURA、Johji YAMAHARA、Masayuki YOSHIKAWA

  DOI：10.1248/cpb.46.1399

  日期：——

  We examined the structure-related activity of oleanolic acid glycosides with respect to their inhibitory effect on the increase in serum glucose in oral glucose-loaded rats and their mechanism of action using oleanolic acid 3-O-glucuronide and momordin Ic. Both the 3-O-monodesmoside structure and 28-carboxyl group were confirmed to be essential for such activity, and the 3-O-glucuronide was more potent than 3-O-glucoside. On the other hand, the 28-ester glucoside moiety and 6'-methyl ester of the glucuronide moiety reduced such activity. Oleanolic acid 3-O-glucuronide and momordin Ic, both of which inhibited the increase in serum glucose in oral glucose-loaded rats, did not lower serum glucose in normal or intraperitoneal glucose-loaded rats, or alloxan-in-duced diabetic mice. These glycosides were found to suppress gastric emptying in rats, and also inhibit glucose uptake in the rat small intestine in vitro. These results indicate that oleanolic acid 3-O-glucuronide and momordin Ic, given orally, have neither insulin-like activity nor insulin releasing-activity. They exhibit their hydpoglycemic activity by suppressing the transfer of glucose from the stomach to the small intestine and by inhibiting glucose transport at the brush border of the small intestine.

  我们利用齐墩果酸 3-O-葡萄糖醛酸苷和 Momordin Ic，研究了齐墩果酸苷在抑制口服葡萄糖负荷大鼠血清葡萄糖升高方面的结构相关活性及其作用机制。经证实，3-O-单去甲糖苷结构和 28-羧基都是这种活性的必要条件，而且 3-O-葡萄糖醛酸苷比 3-O-葡萄糖苷更有效。另一方面，28-酯葡萄糖苷分子和葡萄糖醛酸分子的 6'- 甲基酯会降低这种活性。齐墩果酸 3-O-葡萄糖醛酸和 Momordin Ic 都能抑制口服葡萄糖负荷大鼠血清葡萄糖的升高，但不能降低正常或腹腔葡萄糖负荷大鼠或阿脲诱导的糖尿病小鼠的血清葡萄糖。研究发现，这些苷可抑制大鼠的胃排空，还可抑制大鼠小肠在体外摄取葡萄糖。这些结果表明，口服齐墩果酸 3-O-葡萄糖醛酸苷和 Momordin Ic 既没有胰岛素样活性，也没有胰岛素释放活性。它们通过抑制葡萄糖从胃向小肠的转移和抑制葡萄糖在小肠刷状缘的转运来显示其降血糖活性。
• [EN] MEDICAL USE OF PENTACYCLIC TRITERPENOID SAPONIN COMPOUND AND PHARMACEUTICAL COMPOSITION THEREOF<br/>[FR] UTILISATION MÉDICALE D'UN COMPOSÉ DE SAPONINE TRITERPÉNOÏDE PENTACYCLIQUE ET COMPOSITION PHARMACEUTIQUE ASSOCIÉE<br/>[ZH] 五环三萜皂苷化合物的医药用途及其药物组合物
  申请人：UNIV CHINA PHARMA

  公开号：WO2020244454A1

  公开（公告）日：2020-12-10

  五环三萜皂苷化合物的医药用途及其药物组合物，具体如式(I)～(XVI)所示的五环三萜皂苷在制备预防或治疗由AMPK和/或ERRα介导的疾病的药物中的用途，包括制备预防或治疗如肝脏疾病、呼吸系统疾病、代谢性疾病、自身免疫性疾病、心脑血管疾病、肾病、中枢神经系统疾病或肌营养不良症等疾病的药物。本发明预防和治疗AMPK和/或ERRα介导的疾病的药物组合物含有式(I)～(XVI)化合物或其药学上可接受的盐或溶剂化物作为活性成份和药学上可接受的辅料。
• SAPONIN COMPOUND TARGETING PD-1 AND APPLICATION THEREOF
  申请人：EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY

  公开号：US20200163983A1

  公开（公告）日：2020-05-28

  Provided are use of a saponin compound of formula (I) or (II), or a pharmaceutically acceptable salt, prodrug or solvate thereof, in the manufacture of a medicament targeting PD-1. The medicament targeting PD-1 is one which treats a disease by inhibiting PD-1 from binding to a ligand thereof. The disease may be a tumor, an infection caused by a bacterium, a virus or a fungus, or an inflammatory disease.
• [EN] ANTI-FUNGAL COMPOSITIONS<br/>[FR] COMPOSITIONS ANTIFONGIQUES
  申请人：VIB VZW

  公开号：WO2015032964A1

  公开（公告）日：2015-03-12

  The present invention relates to anti-fungal uses of plant-derived saponins. In particular, the invention deals with the anti-fungal uses of momordin Icand its glucopyranosyl derivatives for the treatment of fungal infections such as for example caused by the genus Candida, more particularly the species Candida albicans and Candida glabrata.