3-O-β-D-glucopyranosyl-3-β-hydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranoside

• 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: 3-O-β-D-glucopyranosyl-3-β-hydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranoside
• 英文别名: 3-O-β-D-glucopyranosyl-3β-hydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranoside；olean-12-en-28-oic acid 3-(β-D-glucopyranosyloxy)-β-D-glucopyranosyl ester；3-O-(β-D-glucopyranosyl)oleanolic acid 28-O-β-D-glucopyranosyl ester；3-O-β-D-glucuropyranosyl oleanolic acid 28-O-β-D-glucopyranoside；3-O-(β-D-glucopyranosyl)-oleanolic acid-28-O-β-D-glucopyranoside；3-O-β-D-glucopyranosyl-oleanolic acid-28-O-β-D-glucopyranoside；[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• 化学式: C₄₂H₆₈O₁₃
• 分子量: 780.994
• InChiKey: LKYABSOYLMWGQR-WLMDKFIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  55
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  216
• 氢给体数：
  8
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  3-O-β-D-glucopyranosyl-3-β-hydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranoside 、 sodium hydroxide 、 二甲基亚砜 、 碘甲烷 生成 [(2R,3R,4S,5R,6R)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2R,3R,4S,5R,6R)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
  参考文献：
  名称：

  SATI, O. P.;BAHUGUNA, S.;UNIYAL, S.;SAKAKIBARA, J.;KAIYA, T.;NAKAMURA, A., J. NATUR. PROD., 53,(1990) N, C. 466-469

  摘要：

  DOI：
• 作为产物：
  描述：

  olean-12-en-28-oic acid 3-[(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxy]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl ester 在 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到3-O-β-D-glucopyranosyl-3-β-hydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranoside
  参考文献：
  名称：

  在连续微流/分批条件下，通过糖基化-脱保护序列合成双糖苷齐墩果酸皂苷

  摘要：

  我们报告了通过连续流动糖基化-分批脱保护序列，使用微流反应器Comet X-01合成了一系列双去甲齐墩果油酸皂苷的首次合成。这项研究的主要结果可以概括如下：（1）以定量产率实现了齐墩果酸在C-28上的微流体糖基化，并被用于合成6种C-28-单糖苷皂苷。（2）在不产生原酸酯副产物的情况下，以良好的产率实现了齐墩果酸在C-3的微流体糖基化，并被用于合成三种双去糖苷皂苷。（3）通过涉及两个纯化的四个步骤，通过微流体糖基化-分批脱保护序列来连续合成皂苷。因此，

  DOI：

  10.1021/acs.joc.7b00841

文献信息

• USE OF URSOLIC ACID SAPONIN,OLEANOLIC ACID SAPONIN IN PREPARATION OF INCREASING LEUCOCYTES AND/OR PLATELET MEDICINE
  申请人：Guang Bing

  公开号：US20100197898A1

  公开（公告）日：2010-08-05

  The invention provides the use of ursolic acid saponin and oleanolic acid saponin of formula (I) in preparing medicaments for increasing leucocytes and/or platelets. The invention also provides a pharmaceutical composition containing the same compound. The invention utilizes the cheap and accessible ursolic acid and oleanolic acid which are widely present in natural plants as raw materials, introduces monosaccharyls or oligosaccharyls by structural modification. It is proved by pharmacological tests that the compound of formula (I) have an activity of obviously increasing leucocytes and/or platelets.

  本发明提供了使用式(I)的熊果酸皂苷和齐墩果酸皂苷制备增加白细胞和/或血小板的药物的方法。本发明还提供了含有相同化合物的制药组合物。本发明利用廉价且易得的熊果酸和齐墩果酸，它们广泛存在于天然植物中作为原料，并通过结构修饰引入单糖或寡糖。药理学试验证明，式(I)化合物具有明显增加白细胞和/或血小板的活性。
• Biotransformation of oleanolic acid by<i>Alternaria longipes</i>and<i>Penicillium adametzi</i>
  作者：Dai-Lin Liu、Ying Liu、Feng Qiu、Ying Gao、Jing-Ze Zhang

  DOI：10.1080/10286020.2010.547028

  日期：2011.2

  Microbial transformation of oleanolic acid (1) was carried out. Six transformed products (2-7) from 1 by Alternaria longipes and three transformed products (8-10) from 1 by Penicillium adametzi were isolated. Their structures were elucidated as 2,3,19-trihydroxy-ursolic acid-28-O--d-glucopyranoside (2), 2,3,19-trihydroxy-ursolic acid-28-O--d-glucopyranoside (3), oleanolic acid 28-O--d-glucopyranosyl ester (4), oleanolic acid-3-O--d-glucopyranoside (5), 3-O-(-d-glucopyranosyl)-oleanolic acid-28-O--d-glucopyranoside (6), 2,3,19a-trihydroxy-oleanolic acid-28-O--d-glucopyranoside (7), 21-hydroxyl oleanolic acid-28-O--d-glucopyranoside (8), 21-hydroxyl oleanolic acid (9), and 7,21-dihydroxyl oleanolic acid (10) based on the extensive NMR studies. Among them, 10 was a new compound and compounds 5 and 8-10 had stronger cytotoxic activities against Hela cell lines than the substrate. At the same time, it was reported for the first time in this paper that the skeletons of compounds 2 and 3 were changed from oleanane to uranane and seven glycosidation products were obtained by biotransformation.
• Jangwan; Dobhal, Maneesha; Kumar, Naveen, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 1, p. 123 - 126
  作者：Jangwan、Dobhal, Maneesha、Kumar, Naveen

  DOI：——

  日期：——
• SATI, O. P.;BAHUGUNA, S.;UNIYAL, S.;SAKAKIBARA, J.;KAIYA, T.;NAKAMURA, A., J. NATUR. PROD., 53,(1990) N, C. 466-469
  作者：SATI, O. P.、BAHUGUNA, S.、UNIYAL, S.、SAKAKIBARA, J.、KAIYA, T.、NAKAMURA, A.

  DOI：——

  日期：——
• US8394776B2
  申请人：——

  公开号：US8394776B2

  公开（公告）日：2013-03-12