oleanolic acid 3-O-β-D-xylopyranoside | 28283-45-6

• 物质功能分类: 天然产物 - 萜类
• 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: oleanolic acid 3-O-β-D-xylopyranoside
• 英文别名: 3-O-β-D-xylopyranosyl oleanolic acid；3-O-β-D-xylopyranosyloleanolic acid；prosapogenin PS-A；songoroside A；3-O-(β-D-xylopyranosyl)oleanolic acid；(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 28283-45-6；28283-48-9；58163-30-7；60252-11-1；61617-29-6
• 化学式: C₃₅H₅₆O₇
• 分子量: 588.825
• InChiKey: HZLWUYJLOIAQFC-SMRQUVCNSA-N

物化性质

• 熔点：
  238-239 °C
• 沸点：
  685.4±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 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：

  oleanolic acid 3-O-β-D-xylopyranoside 生成 齐墩果酸
  参考文献：
  名称：

  AKIMALIEV, A. A.;PUTIEVA, ZH. M.;ALIMBAEVA, P. K.;ABUBAKIROV, N. K., XIMIYA PRIROD. SOED.,(1988) N, S. 885-886

  摘要：

  DOI：
• 作为产物：
  描述：

  benzyl 3-O-β-D-xylopyranosyloleanolate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以90%的产率得到oleanolic acid 3-O-β-D-xylopyranoside
  参考文献：
  名称：

  Synthesis and α-glucosidase inhibitory activity of oleanolic acid derivatives

  摘要：

  Glucosidations of oleanolic acid (1) and its dihydroxy-olide derivatives (2) were carried out to provide eight glycosides. All synthesized compounds were evaluated by in vitro -glucosidase inhibitory activity assay. 3-Acetyl dihydroxy-olide oleanolic derivative 15 showed the most potent inhibitory effect. Structure-activity relationships within these compounds are discussed.

  DOI：

  10.1080/10286020903405456

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。
• Facile Synthesis of Oleanolic Acid Monoglycosides and Diglycosides
  作者：Yu Sha、Mao-Cai Yan、Jiao Liu、Yang Liu、Mao-Sheng Cheng

  DOI：10.3390/molecules13071472

  日期：——

  condensation of the carboxylic acid with bromo-glycosides was found to be more efficient in the synthesis of 28-glycosides. Two approaches were investigated and proved practicable in the preparation of 3,28- diglycosides. This method is suitable for preparing oleanolic acid glycosides with structural diversity for extensive biological evaluation and structure-activity relationship study, and it also apply new

  齐墩果酸及其苷类是重要的天然产物，具有多种有吸引力的生物活性，如抗肿瘤、抗病毒和抗炎特性。在目前的工作中，15 种带有各种糖基的齐墩果酸皂苷，包括 3-单糖苷、28-单糖苷和 3,28-二糖苷，很容易以高产率合成。选择苄基作为 COOH(28) 基团的保护基团，而不是常用的甲基和烯丙基，以避免最终脱保护的困难。发现碱促进羧酸与溴糖苷的缩合在 28-糖苷的合成中更有效。研究了两种方法并证明在制备 3,28-二糖苷中是可行的。
• New Cytotoxic Oleanane Saponins from the Infructescences of<i>Polyscias amplifolia</i>from the Madagascar Rainforest
  作者：Chaturvedula, V. S. Prakash、Schilling, Jennifer K.、Miller, James S.、Andriantsiferana, Rabodo、Rasamison, Vincent E.、Kingston, David G. I.

  DOI：10.1055/s-2003-39711

  日期：2003.5

  infructescences of Polyscias amplifolia resulted in the isolation of two new oleanolic acid saponins, polyfoliolides A (1) and B (2), in addition to the two known saponins 3-O-beta-D-galactopyranosyloleanolic acid (3) and 3-O-beta-D-galactopyranosyl-(1-->4)-beta-D-galactopyranosyloleanolic acid (4). The structures of the two new compounds were established as 3-O-beta- D-galactopyranosyl-(1-->4)-beta

  生物测定法指导的一枝龙舌兰果实提取物乙醇提取物的分离，除了分离出两种已知的皂苷3-O-β-D外，还分离出了两种新的齐墩果酸皂苷，多叶磷脂A（1）和B（2）。 -galactopyranosyloleanolic acid（3）和3-O-β-D-galactopyranosyl-（1→4）-beta-D-galactopyranosyloleanolic acid（4）。这两个新化合物的结构被确定为3-O-β-D-吡喃并吡喃半乳糖基酸（1-> 4）-β-D-吡喃并吡喃半乳糖基酸（1）和3-O-β-D-吡喃并吡喃半乳糖基-（1 -> 4）-α-L-阿拉伯吡喃并吡喃型胡杨酸（2）基于广泛的1D和2D NMR光谱数据解释和化学转化。所有分离出的化合物均显示出对A2780人卵巢癌细胞系的弱细胞毒性，IC50值在6.7至10.8 microg / mL范围内。
• Triterpenoid saponins from Pterocephalus hookeri
  作者：Tian Jun、Wu Feng-E、Qiu Ming-Hua、Nie Rui-Lin

  DOI：10.1016/0031-9422(93)85174-p

  日期：1993.1

  Four new triterpenoid saponins, named hookerosides A-D, were isolated from Pterocephalus hookeri. Based on chemical and spectral evidence, their structures were determined as 3-O-beta-D-glucopyranosyl(1-->4)-beta-D-xylopyranosyl(1-->3)-alpha-L- Rhamnopyranosyl(1-->2)-beta-D-xylopyranosyl oleanolic acid 28-O-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranoside, 3-O-beta-D-xylopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->4)-beta-D- xylopyranosyl(1-->3)-alpha-L-rhamnopyranosyl(1-->2)-beta-D-xylopyranosyl oleanolic acid 28-O-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranoside, 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-xylopyranosyl(1-->4)-beta-D- glucopyranosyl(1-->4)-beta-D-xylopyranosyl(1-->3)-alpha-L-rhamnopyranosy l(1-->2 ) beta-D-xylopyranosyl oleanolic acid 28-O-beta-D-glucopyranosyl(1-->6)-beta-glucopyranoside and oleanolic acid 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D- xylopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->4)-beta-D-xylopyranosyl(1 -->3)- alpha-L-rhamnopyranosyl(1-->2)-beta-D-xylopyranoside, respectively.
• US8394776B2
  申请人：——

  公开号：US8394776B2

  公开（公告）日：2013-03-12