3β,21β-dihydroxyolean-12-en-28- oic acid-28-O-β-D-glucopyranosyl ester | 183294-29-3

• 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,21β-dihydroxyolean-12-en-28- oic acid-28-O-β-D-glucopyranosyl ester
• 英文别名: 21β-hydroxy oleanolic acid-28-O-β-D-glucopyranoside；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (3S,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bS)-3,10-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 183294-29-3
• 化学式: C₃₆H₅₈O₉
• 分子量: 634.851
• InChiKey: CEMJRABGGWOEJQ-USLJWFFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  45
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  齐墩果酸 、 D-glucose 在 Penicillium adametzi AS 3.447 、 potato 作用下， 反应 96.0h， 以3.13%的产率得到machaerinic acid
  参考文献：
  名称：

  Biotransformation of oleanolic acid byAlternaria longipesandPenicillium adametzi

  摘要：

  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.

  DOI：

  10.1080/10286020.2010.547028

文献信息

• 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.