betulin 28-O-β-D-glucopyranoside | 40653-06-3

• 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: betulin 28-O-β-D-glucopyranoside
• 英文别名: Betulin-28-yl beta-glucopyranoside；(2R,3R,4S,5S,6R)-2-[[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-3a-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 40653-06-3
• 化学式: C₃₆H₆₀O₇
• 分子量: 604.868
• InChiKey: ANRUOMRHTQVXPW-NZHUUUDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  43
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,2,3,4,6-戊-O-苯甲酰基-D-吡喃葡萄糖苷 在 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 氢溴酸 、 caesium carbonate 、 溶剂黄146 、 silver carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 9.5h， 生成 betulin 28-O-β-D-glucopyranoside
  参考文献：
  名称：

  Glycosidation of lupane-type triterpenoids as potent in vitro cytotoxic agents

  摘要：

  The weak hydrosolubility of betulinic acid (3) hampers the clinical development of this natural anticancer agent. In order to circumvent this problem and to enhance the pharmacological properties of betulinic acid (3) and the lupane-type triterpenes lupeol (1), betulin (2), and methyl betulinate (7), glycosides (beta-D-glucosides, alpha-L-rhamnosides, and alpha-D-arabinosides) were synthesized and in vitro tested for cytotoxicity against three cancerous (A-549, DLD-1, and B16-F1) and one healthy (WS1) cell lines. The addition of a sugar moiety at the C-3 or C-28 position of betulin (2) resulted in a loss of cytotoxicity. In contrast, the 3-O-beta-D-glucosidation of lupeol (1) improved the activity by 7- to 12-fold (IC50 14-15.0 mu M). Moreover, the results showed that cancer cell lines are 8- to 12-fold more sensitive to the 3-O-alpha-L-rhamnopyranoside derivative of betulinic acid (IC50 2.6-3.9 mu M, 22) than the healthy cells (IC50 31 mu M). Thus, this study indicates that 3-O-glycosides of lupane-type triterpenoids represent an interesting class of potent in vitro cytotoxic agents. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.075

文献信息

• EXTERNAL PREPARATION FOR THE SKIN AND BEAUTIFYING AGENTS
  申请人：The Nisshin OilliO, Ltd.

  公开号：EP1295587A1

  公开（公告）日：2003-03-26

  The present invention relates to an external agent for the skin comprising at least one member selected from the group consisting of maslinic acid, erythrodiol, uvaol, betulinic acid, betulin, physiologically acceptable salts thereof and derivatives thereof.

  本发明涉及一种皮肤外用制剂，它包含至少一种选自马斯林酸、红景天醇、莼菜醇、白桦脂酸、白桦脂素、它们的生理上可接受的盐及其衍生物组成的组的成员。
• ANTITUMOR AGENTS
  申请人：The Nisshin Oillio, Ltd.

  公开号：EP1321145A1

  公开（公告）日：2003-06-25

  The present invention relates to an antitumor agent, which comprises, as an effective component, a compound selected from the group consisting of maslinic acid, erythrodiol, uvaol, betulinic acid, betulin and physiologically acceptable salts thereof or derivatives thereof.

  本发明涉及一种抗肿瘤剂，其有效成分包括选自马斯林酸、红景天二醇、莼菜醇、白桦脂酸、白桦脂素及其生理上可接受的盐或其衍生物的化合物。
• BEAUTIFYING FOODS AND DRINKS AND PERORAL BEAUTIFYING PREPARATIONS
  申请人：The Nisshin Oillio, Ltd.

  公开号：EP1340501A1

  公开（公告）日：2003-09-03

  The present invention relates to a food or beverage comprising at least one member selected from the group consisting of 5-membered ring-containing triterpenes and physiologically acceptable salts or derivatives thereof. The present invention also relates to an orally administered whitening agent comprising, as an effective component, at least one member selected from the group consisting of 5-membered ring-containing triterpenes and physiologically acceptable salts or derivatives thereof.

  本发明涉及一种食品或饮料，其中含有至少一种选自含五元环的三萜类化合物及其生理上可接受的盐或衍生物组成的组的成员。本发明还涉及一种口服美白剂，其有效成分包括至少一种选自含五元环的三萜类化合物及其生理上可接受的盐或衍生物组成的组。
• FEEDS AND FERTILIZERS CONTAINING PENTACYCLIC TRITERPENES
  申请人：The Nisshin OilliO, Ltd.

  公开号：EP1430787A1

  公开（公告）日：2004-06-23

  The present invention relates to a feed, a fertilizer, a melanogenesis- inhibitory agent for animals and plants and a blackening/browning-inhibitory composition for animals and plants, each comprising, as an effective component, at least one member selected from the group consisting of pentacyclic triterpenes, physiologically acceptable salts thereof and derivatives thereof, which have an excellent melanogenesis-inhibitory effect.

  本发明涉及一种饲料、一种肥料、一种动植物黑色素生成抑制剂和一种动植物变黑/褐变抑制组合物，其中每一种都包含至少一种选自五环三萜类化合物、其生理上可接受的盐类及其衍生物组成的组的有效成分，它们具有极佳的黑色素生成抑制效果。
• Hypolipidemic properties of betulin glycosides
  作者：A. S. Ivanov、T. S. Zakharova、L. É. Odinokova、N. I. Uvarova

  DOI：10.1007/bf01145561

  日期：1987.9