3-O-α-L-arabinopyranosyl ursolic acid | 126721-52-6

• 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-α-L-arabinopyranosyl ursolic acid
• 英文别名: ursolic acid 3-O-α-L-arabinopyranoside；3β-[α-(L-arabinopyranosyl)oxy]urs-12,19(20)-dien-28-oic acid；(1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-1,2,6a,6b,9,9,12a-heptamethyl-10-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
• CAS: 126721-52-6
• 化学式: C₃₅H₅₆O₇
• 分子量: 588.825
• InChiKey: GZQIINDHMUJEAM-KSYVTUHKSA-N

物化性质

• 熔点：
  245-255 °C
• 沸点：
  688.6±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  42
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-O-α-L-arabinopyranosyl ursolic acid 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 3-O-(α-L-arabinopyranosyl)ursolic acid sodium salt
  参考文献：
  名称：

  USE OF URSOLIC ACID SAPONIN,OLEANOLIC ACID SAPONIN IN PREPARATION OF INCREASING LEUCOCYTES AND/OR PLATELET MEDICINE

  摘要：

  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。

  公开号：

  US20100197898A1
• 作为产物：
  描述：

  熊果酸 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 3-O-α-L-arabinopyranosyl ursolic acid
  参考文献：
  名称：

  Synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue

  摘要：

  The focus of this work was on the synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue. Therefore, 3-O-{[beta-D-glucopyranosyl-(1-->2)]-[alpha-L-arabinopyranosyl-(1-->3)]-alpha-L-arabinopyranosyl}ursolic acid-28-O-[beta-D-glucopyranosyl] ester 1 was concisely synthesized by two strategies in 22% and 41% overall yield, respectively, and another congener 3-O-{[beta-D-xylopyranosyl-(1-->2)]-[beta-D-glucopyranosyl-(1-->3)]-alpha-L-arabinopyranosyl}ursolic acid-28-O-[beta-D-glucopyranosyl] ester 2 was also efficiently prepared in 81% overall yield. The H-1 NMR and C-13 NMR signals of saponin 2 are all consistent with those reported for the natural product. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.06.024

文献信息

• 10.1016/j.bmc.2024.117737
  作者：Sylla, Balla、Jost, Gilles、Lavoie, Serge、Legault, Jean、Gauthier, Charles、Pichette, André

  DOI：10.1016/j.bmc.2024.117737

  日期：——

  of ursane-type pentacyclic triterpenoids for pharmacological use is their poor aqueous solubility, which can impede their effectiveness as therapeutics agents. In this study, we present the facile synthesis of ursolic acid monodesmosides and uvaol bidesmosides, incorporating naturally occurring and water-soluble pentoses and deoxyhexose sugar moieties of opposite and -configurations at the C3 or C3/C28

  熊果酸和山楂醇是天然存在的三萜类化合物，具有广泛的药理活性，包括细胞毒性。然而，开发用于药理学用途的乌苏烷型五环三萜类化合物的主要挑战是它们的水溶性差，这可能妨碍它们作为治疗剂的有效性。在这项研究中，我们提出了熊果酸单链苷和乌苏醇双链苷的简便合成，在乌苏烷核心的C3或C3/C28位置掺入了天然存在的水溶性戊糖和脱氧己糖部分的相反和-构型。评估了二十种合成皂苷对肺癌（A549）和结直肠腺癌（DLD-1）细胞系的细胞毒性。值得注意的是，与它们的非细胞毒性母体三萜类化合物相比，所有双锁链乌苏醇皂苷均显示出细胞毒性。对于每个乌苏烷型皂苷系列，最活跃的化合物是 3--α 阿拉伯吡喃糖基熊果酸 () 和 3,28-二-α 吡喃鼠李糖基乌索醇 ()，显示出针对 A549 和 DLD-1 癌症的低微摩尔范围内的 IC 值线。
• Synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue
  作者：Peng Wang、Chunxia Li、Jing Zang、Ni Song、Xiuli Zhang、Yingxia Li

  DOI：10.1016/j.carres.2005.06.024

  日期：2005.9

  The focus of this work was on the synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue. Therefore, 3-O-[beta-D-glucopyranosyl-(1-->2)]-[alpha-L-arabinopyranosyl-(1-->3)]-alpha-L-arabinopyranosyl}ursolic acid-28-O-[beta-D-glucopyranosyl] ester 1 was concisely synthesized by two strategies in 22% and 41% overall yield, respectively, and another congener 3-O-[beta-D-xylopyranosyl-(1-->2)]-[beta-D-glucopyranosyl-(1-->3)]-alpha-L-arabinopyranosyl}ursolic acid-28-O-[beta-D-glucopyranosyl] ester 2 was also efficiently prepared in 81% overall yield. The H-1 NMR and C-13 NMR signals of saponin 2 are all consistent with those reported for the natural product. (C) 2005 Elsevier Ltd. All rights reserved.
• 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。