(3β)-oleanolic acid 3-β-D-glucopyranosiduronic acid 6-methyl ester | 51724-38-0

• 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: (3β)-oleanolic acid 3-β-D-glucopyranosiduronic acid 6-methyl ester
• 英文别名: 3-O-(β-D-glucuronopyranosyl-6-O-methyl ester)-olean-12-ene-28-olic acid；oleanolic acid 3-O-β-D-glucuronopyranoside-6'-O-methyl ester；chikusetsusaponin IVa 28-desglucosyl prosapogenin dimethyl ester；oleanolic acid 3-O-methyl-β-D-glucuronopyranosiduronoate；oleanolic acid 3-O-6'-O-methyl-β-D-glucuronopuranoside；oleanolic acid 3-O-6'-O-methyl-β-D-glucuronopyranoside；Calenduloside E, Monomethyl ester；(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-methoxycarbonyloxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 51724-38-0
• 化学式: C₃₇H₅₈O₉
• 分子量: 646.862
• InChiKey: PLFVAHQBFNVLPJ-VAYXFIKJSA-N

物化性质

• 熔点：
  222-224 °C
• 沸点：
  717.7±60.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  46
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (3β)-oleanolic acid 3-β-D-glucopyranosiduronic acid 6-methyl ester 生成 齐墩果酸
  参考文献：
  名称：

  PAPHASSARANG, S.;RAYNAUD, J.;LUSSIGNOL, M.;BECCHI, M., PHYTOCHEMISTRY, 28,(1989) N, C. 1539-1541

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl (2S,3S,4S,5R,6S)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2S,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,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylate 生成 (3β)-oleanolic acid 3-β-D-glucopyranosiduronic acid 6-methyl ester
  参考文献：
  名称：

  PAPHASSARANG, S.;RAYNAUD, J.;LUSSIGNOL, M.;BECCHI, M., PHYTOCHEMISTRY, 28,(1989) N, C. 1539-1541

  摘要：

  DOI：

文献信息

• Studies on nepalese crude drugs. III. On the saponins of Hedera nepalensis K. Koch.
  作者：HARUHISA KIZU、SHINGO KITAYAMA、FUKIO NAKATANI、TSUYOSHI TOMIMORI、TSUNEO NAMBA

  DOI：10.1248/cpb.33.3324

  日期：——

  Twelve saponins, tentatively named HN-saponins A (I), B (II), D1 (III), D2 (IV), E (V), F (VI), H (VII), I (VIII), K (X), M (XII), N (XIII) and P (XIV), were isolated from the stem and bark of Hedera nepalensis K. KOCH. (Araliaceae). Compounds II, V, XII, XIII and XIV were identified as Kizuta saponins K3, K6, K10, K11 and K12, respectively, which have been isolated from Hedera rhombea BEAN. On the basis of chemical and physicochemical evidence, other saponins were identified as follows : I, a mixture of the β-D-glucopyranosides of campesterol (trace), stigmasterol and β-sitosterol ; III, hederagenin 3-O-β-D-glucopyranoside ; IV, oleanolic acid 3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside ; VI, 3-O-α-L-arabinopyranosyl-hederagenin 28-O-β-D-glucopyranosyl ester ; VII, hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester ; VIII, oleanolic acid 3-O-β-D-glucuronopyranoside ; X, hederagenin 3-O-β-D-glucuronopyranoside. Compounds VI and VII were isolated from nature for the first time, though they had previously been derived from Akebia seed saponin D and Kizuta saponin K12, respectively, by partial hydrolysis.

  从常春藤（Hedera nepalensis K. KOCH.，五加科）的茎和树皮中分离出12种皂苷，暂时命名为HN-皂苷A（I）、B（II）、D1（III）、D2（IV）、E（V）、F（VI）、H（VII）、I（VIII）、K（X）、M（XII）、N（XIII）和P（XIV）。化合物II、V、XII、XIII和XIV分别被鉴定为木通皂苷K3、K6、K10、K11和K12，这些皂苷先前已从木通（Hedera rhombea BEAN）中分离得到。根据化学和物理化学证据，其他皂苷被鉴定如下：I，为菜油固醇（微量）、豆固醇和β-谷固醇的β-D-葡萄糖苷混合物；III，常春藤苷元3-O-β-D-葡萄糖苷；IV，齐墩果酸3-O-α-L-鼠李糖基-(1→2)-α-L-阿拉伯糖苷；VI，3-O-α-L-阿拉伯糖基-常春藤苷元28-O-β-D-葡萄糖苷酯；VII，常春藤苷元28-O-α-L-鼠李糖基-(1→4)-β-D-葡萄糖基-(1→6)-β-D-葡萄糖苷酯；VIII，齐墩果酸3-O-β-D-葡萄糖醛酸苷；X，常春藤苷元3-O-β-D-葡萄糖醛酸苷。化合物VI和VII虽曾分别通过部分水解木通籽皂苷D和木通皂苷K12获得，但这是它们首次从自然界中分离出来。
• Achyranthosides A and B, novel cytotoxic saponins from Achyranthes fauriei root
  作者：Yoshiteru Ida、Yohko Satoh、Mariko Katoh、Masumi Katsumata (nee Ohtsuka)、Miki Nagasao、Kentaro Yamaguchi、Hideo Kamei、Junzo Shoji

  DOI：10.1016/0040-4039(94)85032-1

  日期：1994.9

  Two new saponins, achyranthosides A and B, were isolated from Achyranthes fauriei root, and their structures were elucidated on the basis of chemical and physical evidences. Achyranthoside A methyl ester was found to have significant cytotoxic activity against human colon carcinoma and murine melanoma cells.

  从牛膝草的根中分离出两种新的皂苷，牛膝甙A和B，并根据化学和物理证据阐明了它们的结构。发现牛膝苦苷A甲酯对人结肠癌和鼠黑素瘤细胞具有显着的细胞毒性活性。
• 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。