CorchoionosideC;(6S,9S)-长寿花糖甙 | 185414-25-9

• 物质功能分类: 天然产物 - 倍半萜
• 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: CorchoionosideC;(6S,9S)-长寿花糖甙
• 中文别名: (6S,9S)-长寿花糖甙
• 英文名称: corchoionoside C
• 英文别名: (6S,9S)-roseoside；roseoside；(6S,9S)-9-O-β-D-glucopyranosyloxy-6-hydroxy-3-oxo-α-ionol；(6S,9R)-roseoside；(4S)-4-hydroxy-3,5,5-trimethyl-4-[(E,3S)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybut-1-enyl]cyclohex-2-en-1-one
• CAS: 185414-25-9
• 化学式: C₁₉H₃₀O₈
• 分子量: 386.442
• InChiKey: SWYRVCGNMNAFEK-PUVRWCMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  CorchoionosideC;(6S,9S)-长寿花糖甙 在 acetate buffer 、 β-glucosidase 作用下， 以 水 为溶剂， 反应 48.0h， 以5 mg的产率得到(6S,9S)-vomifoliol
  参考文献：
  名称：

  (6S)-Hydroxy-3-oxo-α-ionol glucosides from Capparis spinosa fruits

  摘要：

  Two new (6S)-hydroxy-3-oxo-alpha-ionol glucosides, together with corchoionoside C ((6S,9S)-roseoside) and a prenyl glucoside, were isolated from mature fruits of Capparis spinosa. The structures were established on the basis of spectroscopic, chiroptic and chemical evidence. In addition, the C-13-resonance of C-9 was found to be of particular diagnostic value in assigning the absolute configuration at that center in ionol glycosides. The alpha-ionol derivatives are metabolites of (+)-(S)-abscisic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(01)00399-5
• 作为产物：
  描述：

  2,3,4,6-O-四特戊酰基-alpha-D-溴代吡喃葡萄糖 在 甲醇 、 lithium hydroxide 、 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 二氯甲烷 为溶剂， 反应 25.83h， 生成 CorchoionosideC;(6S,9S)-长寿花糖甙
  参考文献：
  名称：

  Synthesis of Optically Active Vomifoliol and Roseoside Stereoisomers

  摘要：

  通过α-炔醇11a或11b有效地制备的α,β-炔酮10进行不对称转移氢化反应，成功合成了光学活性的vomifoliol立体异构体1—4及其葡萄糖苷，玫瑰苷立体异构体5—8。同时，还进行了这些立体异构体的HPLC分离。

  DOI：

  10.1248/cpb.53.541

文献信息

• Reinvestigation of the Absolute Stereochemistry of Megastigmane Glucoside, Icariside B5
  作者：Katsuyoshi Matsunami、Hideaki Otsuka、Yoshio Takeda、Toshio Miyase

  DOI：10.1248/cpb.58.1399

  日期：——

  Icariside B5 is one of the widely distributed megastigmane glucosides among plant sources. The absolute structure of icariside B5 was reinvestigated by chemical conversion from the related compound and the application of the modified Mosher's method. As a result, the structure of icariside B5 was revised to be (6S,9S)-6,9-dihydroxymegastigman-4-en-3-one 9-O-β-D-glucopyranoside.

  淫羊藿苷 B5 是植物来源中广泛分布的巨黄酮苷之一。通过对相关化合物进行化学转化，并应用改进的莫舍尔法，重新研究了淫羊藿苷 B5 的绝对结构。结果，冰片苷 B5 的结构被修正为 (6S,9S)-6,9-二羟基巨天麻素-4-烯-3-酮 9-O-β-<小>D-吡喃葡萄糖苷。
• A simple synthesis of four stereoisomers of roseoside and their inhibitory activity on leukotriene release from mice bone marrow-derived cultured mast cells
  作者：Arata Yajima、Yutaka Oono、Ryusuke Nakagawa、Tomoo Nukada、Goro Yabuta

  DOI：10.1016/j.bmc.2008.11.002

  日期：2009.1

  Four stereoisomers of roseoside (vomifoliol glucosides) were synthesized using glucose as a chiral resolving reagent. The four synthetic stereoisomers exhibited inhibitory activity on leukotriene release from mouse bone marrow-derived cultured mast cells (BMCMC). The (6S)-isomers of roseoside were about twice as active as (6R)-isomers. (c) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of Optically Active Vomifoliol and Roseoside Stereoisomers
  作者：Yumiko Yamano、Masayoshi Ito

  DOI：10.1248/cpb.53.541

  日期：——

  A synthesis of optically active vomifoliol stereoisomers 1—4 and their glucosides, roseoside stereoisomers 5—8, was accomplished via α-acetylenic alcohol 11a or 11b effectively prepared by an asymmetric transfer hydrogenation of α,β-acetylenic ketone 10. Simultaneous separation of these stereoisomers by HPLC was also perfomed.

  通过α-炔醇11a或11b有效地制备的α,β-炔酮10进行不对称转移氢化反应，成功合成了光学活性的vomifoliol立体异构体1—4及其葡萄糖苷，玫瑰苷立体异构体5—8。同时，还进行了这些立体异构体的HPLC分离。
• (6S)-Hydroxy-3-oxo-α-ionol glucosides from Capparis spinosa fruits
  作者：İhsan Çalış、Ayşe Kuruüzüm-Uz、Piergiorgio A. Lorenzetto、Peter Rüedi

  DOI：10.1016/s0031-9422(01)00399-5

  日期：2002.2

  Two new (6S)-hydroxy-3-oxo-alpha-ionol glucosides, together with corchoionoside C ((6S,9S)-roseoside) and a prenyl glucoside, were isolated from mature fruits of Capparis spinosa. The structures were established on the basis of spectroscopic, chiroptic and chemical evidence. In addition, the C-13-resonance of C-9 was found to be of particular diagnostic value in assigning the absolute configuration at that center in ionol glycosides. The alpha-ionol derivatives are metabolites of (+)-(S)-abscisic acid. (C) 2002 Elsevier Science Ltd. All rights reserved.