kingisidic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: kingisidic acid
• 英文别名: (1S,4aS,8S,8aS)-1-methyl-3-oxo-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,8,8a-tetrahydro-1H-pyrano[3,4-c]pyran-5-carboxylic acid
• 化学式: C₁₆H₂₂O₁₁
• 分子量: 390.344
• InChiKey: HQEBQNGGKFIFBW-TURDRQEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  172
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-[(2S,3S,4S)-5-methoxycarbonyl-3-[(1S)-1-[(E)-2-methylbut-2-enoyl]oxyethyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]acetic acid 在 六甲基磷酰三胺 、 氢氧化钾 作用下， 以 水 为溶剂， 以92 mg的产率得到kingisidic acid
  参考文献：
  名称：

  A secoiridoid and other constituents of Gonocaryum calleryanum

  摘要：

  Investigation of the leaves, branch, stem and root bark of Gonocaryum calleryanum resulted in the isolation of a new secoiridoid glycoside, gonocaryoside E, together with 14 known compounds. Their structures were elucidated by spectral analysis and chemical transformation. Gonocaryoside E was shown to be a derivative of kingiside in which the lactone ring was open, and with the 8-hydroxy group esterified with tiglic acid. Alkaline hydrolysis of these secoiridoids is discussed. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)80075-7

文献信息

• Secoiridoid and flavonoid glycosides from Gonocaryum calleryanum
  作者：Tetsuo Kaneko、Mayumi Sakamoto、Kazuhiro Ohtani、Aiko Ito、Ryoji Kasai、Kazuo Yamasaki、William G. Padorina

  DOI：10.1016/0031-9422(94)00884-v

  日期：1995.5

  leaves of Gonocaryum calleryanum afforded four new secoiridoid glycosides acylated with 2,3-dihydroxy-2-methylbutanoic acid, three of which have a novel 10-membered dilactone-ring. From this plant, we also isolated a new flavonoid glycoside, apigenin 7-O-β-apiofuranosyl (1 → 6)-β- d -glucopyranoside, along with six known flavonoids and flavonoid glycosides, apigenin, apigenin-5,7-dimethyl ether, apigenin

  摘要 Gonocaryum calleryanum 的叶子提供了 4 种新的 2,3-二羟基-2-甲基丁酸酰化的二环环烯醚苷，其中 3 种具有新的 10 元双内酯环。从这种植物中，我们还分离出了一种新的黄酮苷，芹菜素 7-O-β-apiofuranosyl (1 → 6)-β-d-吡喃葡萄糖苷，以及六种已知的黄酮和黄酮苷，芹菜素，芹菜素-5,7-二甲基醚、芹菜素三甲醚、芹菜素 7-O-葡萄糖苷、芹菜素 7-O-新橙皮苷和牡荆素。通过化学和光谱手段阐明了新糖苷的结构。