pulchellamine A | 1007346-78-2

• 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: pulchellamine A
• 英文别名: (2S)-2-[[(3R,3aR,4S,6aR,8S,9aR,9bR)-4,8-dihydroxy-6,9-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-3-yl]methylamino]-4-amino-4-oxobutanoic acid
• CAS: 1007346-78-2
• 化学式: C₁₉H₂₆N₂O₇
• 分子量: 394.425
• InChiKey: YEGRITYHHMCDPK-DNTBNWOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  159
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  L-天冬酰胺 、 4,8-二羟基-3,6,9-三亚甲基-3a,4,5,6a,7,8,9a,9b-八氢薁并[5,4-d]呋喃-2-酮 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以13%的产率得到pulchellamine A
  参考文献：
  名称：

  Guaiane Sesquiterpene Lactones and Amino Acid-Sesquiterpene Lactone Conjugates from the Aerial Parts of Saussurea pulchella

  摘要：

  Two new guaiane sesquiterpene lactones (1 and 2) and seven new amino acid-sesquiterpene lactone conjugates (3-9), together with six known sesquiterpene lactones (10-15), were isolated from the methanol extract of the aerial parts of Saussurea pulchella. Their structures were determined on the basis of spectroscopic and chemical methods to be 8 alpha-O-(3'-hydroxy-3'-methylbutyryl)desacylcynaropicrin (1), 8 alpha-O-(2', 3'-dihydroxyisobutyryl)11 beta,13-dihydrodesacylcynaropicrin (2), and pulchellamines A, B, C, D, E, F, and G (3-9). The structures of the new amino acid-sesquiterpene lactone conjugates, pulchellamines A, B, C, D, E, F, and G (3-9), were confirmed by synthesis. The isolated compounds were evaluated for cytotoxic activity against four human tumor cell lines. Compounds 11 and 12 exhibited cytotoxicity against skin melanoma (SK-MEL-2) and ovary malignant ascites (SK-OV-3) human tumor cell lines with ED(50) values of 1.53 and 4.07 mu M, and 2.49 and 7.42 mu M, respectively.

  DOI：

  10.1021/np800005r

文献信息

• Guaiane Sesquiterpene Lactones and Amino Acid-Sesquiterpene Lactone Conjugates from the Aerial Parts of <i>Saussurea pulchella</i>
  作者：Min Cheol Yang、Sang Un Choi、Wahn Soo Choi、Sun Yeou Kim、Kang Ro Lee

  DOI：10.1021/np800005r

  日期：2008.4.1

  Two new guaiane sesquiterpene lactones (1 and 2) and seven new amino acid-sesquiterpene lactone conjugates (3-9), together with six known sesquiterpene lactones (10-15), were isolated from the methanol extract of the aerial parts of Saussurea pulchella. Their structures were determined on the basis of spectroscopic and chemical methods to be 8 alpha-O-(3'-hydroxy-3'-methylbutyryl)desacylcynaropicrin (1), 8 alpha-O-(2', 3'-dihydroxyisobutyryl)11 beta,13-dihydrodesacylcynaropicrin (2), and pulchellamines A, B, C, D, E, F, and G (3-9). The structures of the new amino acid-sesquiterpene lactone conjugates, pulchellamines A, B, C, D, E, F, and G (3-9), were confirmed by synthesis. The isolated compounds were evaluated for cytotoxic activity against four human tumor cell lines. Compounds 11 and 12 exhibited cytotoxicity against skin melanoma (SK-MEL-2) and ovary malignant ascites (SK-OV-3) human tumor cell lines with ED(50) values of 1.53 and 4.07 mu M, and 2.49 and 7.42 mu M, respectively.