2α,3β,19α-trihydroxy-oleanolic acid-28-O-β-D-glucopyranoside | 31297-79-7

• 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: 2α,3β,19α-trihydroxy-oleanolic acid-28-O-β-D-glucopyranoside
• 英文别名: 24-deoxy-sericoside；24-deoxysericoside；arjunetin；24-deoxy sericoside；2α,3β,19α-trihydroxy-olean-12-en-28-oic acid β-D-glucopyranosyl ester；2α,3β,19α-Trihydroxy-olean-12-en-28-saeure-β-D-glucopyranosylester；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,4aR,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-1,10,11-trihydroxy-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: 31297-79-7
• 化学式: C₃₆H₅₈O₁₀
• 分子量: 650.851
• InChiKey: CUOZRGBQTOSWAY-PWEPJYDOSA-N

物化性质

• 沸点：
  741.5±60.0 °C(Predicted)
• 密度：
  1.31

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  46
• 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：
  177
• 氢给体数：
  7
• 氢受体数：
  10

安全信息

• WGK Germany：
  3

制备方法与用途

生物活性

Arjunetin是从Terminalia arjuna中分离出的一种化合物，它具有昆虫取食抑制和生长抑制作用。

体外研究

Arjunetin显示出生长抑制和食量抑制的性质，其半数抑制浓度（GI₅₀）为188.5 μg/g 饲料，饲料抑制半数浓度（FD₅₀）为287.1 μg/g 饲料。

反应信息

• 作为反应物：
  描述：

  2α,3β,19α-trihydroxy-oleanolic acid-28-O-β-D-glucopyranoside 在 lithium aluminium tetrahydride 作用下， 生成 2α,3β,19α,28-tetrahydroxyolean-12-ene
  参考文献：
  名称：

  Row,L.R. et al., Indian Journal of Chemistry, 1970, vol. 8, p. 772 - 775

  摘要：

  DOI：
• 作为产物：
  描述：

  齐墩果酸 、 D-glucose 在 Alternaria longipes AS 3.2875 、 potato 作用下， 反应 96.0h， 以4.54%的产率得到齐墩果酸 beta-D-吡喃葡萄糖基酯
  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

• Process for the preparation of standardized composition of arjunoglucoside from the bark of Terminalia arjuna
  申请人：Majeed Muhammed

  公开号：US10479749B2

  公开（公告）日：2019-11-19

  Disclosed is a novel process for the isolation of bioactive compounds from Terminalia arjuna. More specifically, the invention discloses a process for isolation and enrichment of bioactive compounds Arjunic acid, Arjunolic acid, Arjungenin, Arjunetin, Arjunoglucoside-I, Arjunoglucoside-II, and Catechin from the bark of Terminalia arjuna. The invention also discloses a composition standardized to contain 3% arjunoglucosides isolated from the bark of Terminalia arjuna.

  本发明公开了一种从阿月浑子（Terminalia arjuna）中分离生物活性化合物的新工艺。更具体地说，本发明公开了一种工艺，该工艺可从鸟枞树皮中分离和富集生物活性化合物阿琼酸、阿琼果酸、阿琼腺苷、阿琼甜素、阿琼葡萄糖苷-I、阿琼葡萄糖苷-II 和儿茶素。本发明还公开了一种组合物，该组合物的标准含量为 3%，该组合物是从熊果枞树皮中分离出来的熊果苷。
• 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.
• Row,L.R. et al., Indian Journal of Chemistry, 1970, vol. 8, p. 772 - 775
  作者：Row,L.R. et al.

  DOI：——

  日期：——