(2Z)-4-(beta-D-吡喃葡萄糖基氧基)-2-甲基-2-丁烯腈 | 168433-86-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (2Z)-4-(beta-D-吡喃葡萄糖基氧基)-2-甲基-2-丁烯腈
• 英文名称: Rhodiocyanoside A
• 英文别名: (Z)-2-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybut-2-enenitrile
• CAS: 168433-86-1
• 化学式: C₁₁H₁₇NO₆
• 分子量: 259.259
• InChiKey: ZMELGIPFIBWPHX-GMLQCYRESA-N

物化性质

• 沸点：
  533.3±50.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2Z)-4-(beta-D-吡喃葡萄糖基氧基)-2-甲基-2-丁烯腈 在 β-glucosidase 作用下， 生成 rhodiocyanogenin
  参考文献：
  名称：

  Rhodiocyanosides A and B, new antiallergic cyanoglycosides from chinese natural medicine "Si Lie Hong Jing Tian", the underground part of Rhodiola quadrifida (Pall.) Fisch. et Mey.

  摘要：

  从中国天然药物 "四烈红景天"（日文为 Shiretsukoukeiten）（红景天的地下部分）中分离出两种新的抗过敏氰苷，分别命名为红景天氰苷 A 和 B、以及两种新苷，辛基 α-L-阿拉伯吡喃糖基（1-6）-β-D-吡喃葡萄糖苷和钩藤苷 7-O-β-D-吡喃葡萄糖基（1-3）-α-L-鼠李糖苷。根据化学和物理化学证据确定了它们的化学结构。Rhodiocyanoside A 和 B 具有抑制抗 DNP IgE 致敏的大鼠腹腔渗出细胞释放组胺的活性。此外，还发现 rhodiocyanoside A 可抑制大鼠的 PCA 反应。

  DOI：

  10.1248/cpb.43.1245
• 作为产物：
  描述：

  4-硝基苯-Β-D-吡喃葡萄糖苷 在 吡啶 、 4-二甲氨基吡啶 、 phosphate buffer 、 二甲基硫 、 sodium hydride 、 potassium carbonate 、 臭氧 、 β-glucosidase 作用下， 以 甲醇 为溶剂， 反应 28.0h， 生成 (2Z)-4-(beta-D-吡喃葡萄糖基氧基)-2-甲基-2-丁烯腈
  参考文献：
  名称：

  Chemoenzymatic syntheses of naturally occurring β-glucosides

  摘要：

  Enzymatic glycosidation of the various kinds of primary alcohols 5, 7, 9, 11, 13 and 15 and 4-nitrophenyl-beta-D-glucopyranoside 4 using beta-glucosidase from almonds gave stereoselectively beta-D-glucosides 6, 8, 10, 12, 14 and 16 including the naturally occurring beta-glucosides in moderate yield. Among them, the beta-glucosides 6, 8 and 10 were converted to the cyanoglycosides, rhodiocyanoside A 20a, osmaronin 24a and sutherlandin 29, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00228-1

文献信息

• Bioactive Constituents of Chinese Natural Medicines. II. Rhodiolae Radix. (1). Chemical Structures and Antiallergic Activity of Rhodiocyanosides A and B from the Underground Part of Rhodiola quadrifida (PALL.) FISCH. et MEY. (Crassulaceae).
  作者：Masayuki YOSHIKAWA、Hiromi SHIMADA、Hiroshi SHIMODA、Nobutoshi MURAKAMI、Johji YAMAHARA、Hisashi MATSUDA

  DOI：10.1248/cpb.44.2086

  日期：——

  Two bioactive cyanoglycosides, rhodiocyanosides A and B, and two oligoglycosides, rhodioflavonoside [gossypetin 7-O-β-D-glucopyranosyl(1→3)-α-L-rhamnopyranoside] and rhodiooctanoside [octyl α-L-arabinopyranosyl(1→6)-β-D-glucopyranoside), were isolated from the Chinese natural medicine "Si Lie Hong Jing Tian" (Shiretsukoukeiten in Japanese), the underground part of Rhodiola quadrifida (PALL.) FISCH. et MEY., together with four known compounds : rhodioloside, n-hexyl β-D-glucopyranoside, gossypetin 7-O-α-L-rhamnopyranoside, and tricetin. The chemical structures of new glycosides were determined on the basis of chemical and physicochemical evidence. Rhodiocyanosides A and B exhibited inhibitory activity on the histamine release from rat peritoneal exudate cells sensitized with anti-2, 4-dinitrophenyl IgE. Additionally, rhodiocyanoside A, the major constituent of this natural medicine, was also found to show antiallergic activity in a passive cutaneous anaphylaxis test in rat.

  从红景天地下部分 "四烈红景天"（PALL.SHIRITSUKOUKEITEN）中分离出两种生物活性氰苷--红景天花青苷 A 和 B，以及两种低聚糖苷--红景天黄酮苷 [格桑花素 7-O-β-D-Glucopyranosyl(1→3)-α-L-rhamnopyranoside] 和红景天辛甙 [octyl α-L-arabinopyranosyl(1→6)-β-D-glucopyranoside] 、从中国天然药物 "四烈红景天"（日文为 Shiretsukoukeiten）中分离出来，"四烈红景天 "是红景天（PALL.FISCH. et MEY、以及四种已知化合物：红景天苷、正己基 β-D 吡喃葡萄糖苷、格桑吡汀 7-O-α-L 吡喃鼠李糖苷和三色堇苷。根据化学和物理化学证据确定了新苷的化学结构。红景天花色苷 A 和 B 具有抑制抗-2，4-二硝基苯 IgE 致敏的大鼠腹腔渗出细胞释放组胺的活性。此外，在大鼠被动皮肤过敏性休克试验中，还发现这种天然药物的主要成分红景天花色苷 A 具有抗过敏活性。
• Lotus plant extract with antihistaminic activity
  申请人：ROYAL VETERINARY & AGRICULTURAL UNIVERSITY

  公开号：EP1593383A1

  公开（公告）日：2005-11-09

  An extract from a plant of the genus Lotus, in particular of Lotus japonicus, comprising rhodiocyanoside A and rhodiocyanoside D, a process for preparing it, a pharmaceutical composition comprising it and uses thereof for the manufacture of a medicament with antihistaminic activity.

  一种从莲花属植物，特别是日本莲花中提取的、包含 rhodiocyanoside A 和 rhodiocyanoside D 的提取物，一种制备该提取物的工艺，一种包含该提取物的药物组合物，以及该提取物在制造具有抗组胺活性的药物中的用途。
• Chemoenzymatic syntheses of naturally occurring β-glucosides
  作者：Hiroyuki Akita、Katsumi Kurashima、Takuya Nakamura、Keisuke Kato

  DOI：10.1016/s0957-4166(99)00228-1

  日期：1999.6

  Enzymatic glycosidation of the various kinds of primary alcohols 5, 7, 9, 11, 13 and 15 and 4-nitrophenyl-beta-D-glucopyranoside 4 using beta-glucosidase from almonds gave stereoselectively beta-D-glucosides 6, 8, 10, 12, 14 and 16 including the naturally occurring beta-glucosides in moderate yield. Among them, the beta-glucosides 6, 8 and 10 were converted to the cyanoglycosides, rhodiocyanoside A 20a, osmaronin 24a and sutherlandin 29, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Rhodiocyanosides A and B, new antiallergic cyanoglycosides from chinese natural medicine "Si Lie Hong Jing Tian", the underground part of Rhodiola quadrifida (Pall.) Fisch. et Mey.
  作者：Masayuki YOSHIKAWA、Hiromi SHIMADA、Hiroshi SHIMODA、Hisashi MATSUDA、Johji YAMAHARA、Nobutoshi MURAKAMI

  DOI：10.1248/cpb.43.1245

  日期：——

  Two new antiallergic cyanoglycosides named rhodiocyanosides A and B were isolated from the Chinese natural medicine "Si Lie Hong Jing Tian" (Shiretsukoukeiten in Japanese), the underground part of Rhodiola quadrifida (Pall.) Fisch. et Mey., together with two new glycosides, octyl α-L-arabinopyranosyl(1-6)-β-D-glucopyranoside and gossypetin 7-O-β-D-glucopyranosyl(1-3)-α-L-rhamnopyranoside. Their chemical structures were determined on the basis of chemical and physicochemical evidence. Rhodiocyanosides A and B exhibited inhibitory activity on the histamine release from rat peritoneal exudate cells sensitized with anti-DNP IgE. In addition, rhodiocyanoside A was found to inhibit the PCA reaction in rats.

  从中国天然药物 "四烈红景天"（日文为 Shiretsukoukeiten）（红景天的地下部分）中分离出两种新的抗过敏氰苷，分别命名为红景天氰苷 A 和 B、以及两种新苷，辛基 α-L-阿拉伯吡喃糖基（1-6）-β-D-吡喃葡萄糖苷和钩藤苷 7-O-β-D-吡喃葡萄糖基（1-3）-α-L-鼠李糖苷。根据化学和物理化学证据确定了它们的化学结构。Rhodiocyanoside A 和 B 具有抑制抗 DNP IgE 致敏的大鼠腹腔渗出细胞释放组胺的活性。此外，还发现 rhodiocyanoside A 可抑制大鼠的 PCA 反应。