(Z)-2-[(3E,7E)-4,8-二甲基-10-(2,6,6-三甲基-1-环己烯基)癸-3,7-二烯基]丁-2-烯二酸 | 132911-46-7

• 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
• 中文名称: (Z)-2-[(3E,7E)-4,8-二甲基-10-(2,6,6-三甲基-1-环己烯基)癸-3,7-二烯基]丁-2-烯二酸
• 英文名称: Dehydroluffariellolide diacid
• 英文别名: (Z)-2-[(3E,7E)-4,8-dimethyl-10-(2,6,6-trimethylcyclohexen-1-yl)deca-3,7-dienyl]but-2-enedioic acid
• CAS: 132911-46-7
• 化学式: C₂₅H₃₈O₄
• 分子量: 402.574
• InChiKey: UJEAOVLENYNVEU-SDMOIDSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Fascaplysin A (Fascaplysin Cation / Dehydroluffariellolide Diacid Anion) 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 以46%的产率得到(Z)-2-[(3E,7E)-4,8-二甲基-10-(2,6,6-三甲基-1-环己烯基)癸-3,7-二烯基]丁-2-烯二酸
  参考文献：
  名称：

  Novel sponge-derived amino acids. 12. Tryptophan-derived pigments and accompanying sesterterpenes from Fascaplysinopsis reticulata

  摘要：

  This paper reports the bioactive constituents of Fascaplysinopsis reticulata collected from the Benga Lagoon of the Fiji islands. The previous literature of this genus includes two aplysinopsins (monomeric tryptophans) from F. reticulata, as well as fascaplysin (5a) (an apparent tryptophan dimer) and luffariellolide (3) (a sesterterpene) from Fascaplysinopsis sp. Our investigation of F. reticulata has revealed new sesterterpenes isodehydrouffariellolide (1) and dehydroluffariellolide diacid (2); unique alkaloid-sesterterpene salts fascaplysin A (5b) [fascaplysin cation/dehydroluffariellolide diacid anion] and homofascaplysin A cation/dehydroluffariellolide diacid anion (6); and novel neutral alkaloids homofascaplysin C (7), homofascaplysin B (8), and secofascaplysin A (9). These substances were accompanied by fascaplysin (5a) and the known alkaloid (+)-octopamine 4. The most important findings in this study are (a) fascaplysin derivative 5b is the first known salt comprised of a complex alkaloid cation and a terpene carboxylate anion, and (b) secofascaplysin A (9) is the first naturally occurring beta-carbolinone. An amino acid biogenesis pathway is outlined for each of the above alkaloids. The biological activity profile against the HIV reverse transcriptase is reported for selected metabolites.

  DOI：

  10.1021/jo00010a041

文献信息

• Novel sponge-derived amino acids. 12. Tryptophan-derived pigments and accompanying sesterterpenes from Fascaplysinopsis reticulata
  作者：Carlos Jimenez、Emilio Quinoa、Madeline Adamczeski、Lisa M. Hunter、Phillip Crews

  DOI：10.1021/jo00010a041

  日期：1991.5

  This paper reports the bioactive constituents of Fascaplysinopsis reticulata collected from the Benga Lagoon of the Fiji islands. The previous literature of this genus includes two aplysinopsins (monomeric tryptophans) from F. reticulata, as well as fascaplysin (5a) (an apparent tryptophan dimer) and luffariellolide (3) (a sesterterpene) from Fascaplysinopsis sp. Our investigation of F. reticulata has revealed new sesterterpenes isodehydrouffariellolide (1) and dehydroluffariellolide diacid (2); unique alkaloid-sesterterpene salts fascaplysin A (5b) [fascaplysin cation/dehydroluffariellolide diacid anion] and homofascaplysin A cation/dehydroluffariellolide diacid anion (6); and novel neutral alkaloids homofascaplysin C (7), homofascaplysin B (8), and secofascaplysin A (9). These substances were accompanied by fascaplysin (5a) and the known alkaloid (+)-octopamine 4. The most important findings in this study are (a) fascaplysin derivative 5b is the first known salt comprised of a complex alkaloid cation and a terpene carboxylate anion, and (b) secofascaplysin A (9) is the first naturally occurring beta-carbolinone. An amino acid biogenesis pathway is outlined for each of the above alkaloids. The biological activity profile against the HIV reverse transcriptase is reported for selected metabolites.