dendryphiellic acid A | 121661-45-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dendryphiellic acid A
• 英文别名: (2E,4E,6S)-6-methylocta-2,4-dienoic acid
• CAS: 121661-45-8
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: DNUJBTBPCOIYRL-QALPAXIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  dendryphiellic acid A 在 4-二甲氨基吡啶 、 2,4,6-三氯苯甲酰氯 、 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 dendryphiellin C
  参考文献：
  名称：

  Synthesis of dendryphiellin C, a trinor-sesquiterpene from a marine source

  摘要：

  Enantioselective synthesis of dendryphiellin C, isolated from cultures of Dendryphiella sarina, has been achieved in a convergent way such as coupling of a C9-branched carboxylic acid 10 with a trinor-eremophilane alcohol 11. The latter was synthesized starting from a chiral building block, (1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 16, which was originally prepared in this group using biochemical transformation as a key step. The synthesis was completed through 12 steps from 16 in overall 2.4% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00407-x
• 作为产物：
  描述：

  methyl (2E,4E,6S)-6-methyl-2,4-octadienoate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以78%的产率得到dendryphiellic acid A
  参考文献：
  名称：

  来自海洋氘化菌盐藻登德氏菌盐沼（SUTHERLAND）PUGH等的新型Trinor-ememophilanes（Dendryphiellin B，C和D），Eremophilanes（Dendryphiellin E，F和G）和支链C 9-羧酸（Dendryphiellic Acid A和B）尼科特

  摘要：

  进一步研究了来自海洋氘核菌盐藻Dendryphiella salina的培养物的全球提取物，从而分离出三种被支链C 9-羧酸酯化的新型trinor-eremophilanes ，即dendryphiellin B（=（+）-（1 R *，2 S *，7 R *，8a R *）-1,2,6,7,8,8a-六氢-7-羟基-1,8a-二甲基-6-氧杂萘-2-基（6 R *，2 E，4 E） -6-羟基-6-甲基辛基-2,4-二烯酸酯;（+）- 2），树枝菌素C（=（+）-（1 R *，2 S *，7 R *，8a R*）-1,2,6,7,8,8a-六氢-7-羟基-1,8a-二甲基-6-氧代萘-2-基（6 S，2 E，4 E）-6-甲基辛基-2，4-二羟戊酸酯；（+）- 3））和树状磷脂D（=（+）-（1 R *，2 S *，7 R *，8a R *）-1,2,6,7（8,8a-hexahydro-7

  DOI：

  10.1002/hlca.19890720304

文献信息

• Trinor- and tetranor-eremophilane sesquiterpenoids with anti-neuroinflammatory activity from cultures of the fungus Septoria rudbeckiae
  作者：Li-Bin Lin、Jian Xiao、Yu-Qi Gao、Qiang Zhang、Rui Han、Jian-Zhao Qi、Wen-Bo Han、Biao Xu、Jin-Ming Gao

  DOI：10.1016/j.phytochem.2020.112642

  日期：2021.3

  unprecedented tetranor-eremophilane sesquiterpenoid with an α,β-unsaturated δ-lactone unit bearing a hemiacetal group, while septeremophilane B-H possesses a trinor-eremophilane skeleton. Their structures and absolute configurations were established based on spectroscopic data (NMR and HRESIMS), quantum chemical calculations and electronic circular dichroism (ECD) experiments. All metabolites were tested for

  15 种 eremophilane 倍半萜类化合物，包括 9 种未描述的同源物、septeremophilane AH 和 chaetopenoid G，以及四种共轭不饱和聚酮脂肪酸，包括一种未描述的衍生物，是从金丝孢菌的培养物中分离出来的. Septeremophilane A 是一种前所未有的四去甲-eremophilane 倍半萜类化合物，其 α,β-不饱和 δ-内酯单元带有半缩醛基团，而 septeremophilane BH 具有三去甲-eremophilane 骨架。它们的结构和绝对构型是基于光谱数据（NMR 和 HRESIMS）、量子化学计算和电子圆二色性 (ECD) 实验建立的。
• Eremophilane sesquiterpenes from Hawaiian endophytic fungus Chaetoconis sp. FT087
  作者：Chun-Shun Li、Yuanqing Ding、Bao-Jun Yang、Naomi Hoffman、Hong-Quan Yin、Taifo Mahmud、James Turkson、Shugeng Cao

  DOI：10.1016/j.phytochem.2016.03.005

  日期：2016.6

  Seven sesquiterpene derivatives, including chaetopenoids A-F and dendryphiellin A1, and 6-methyl-(2E, 4E, 6S) octadienoic acid were isolated from the culture broth of Chaetoconis sp. FT087. Their structures were determined through the analysis of HRMS and NMR spectroscopic data. The absolute configurations of chaetopenoids A-D were elucidated by comparison of their CD and optical rotation data with

  从Chaetoconis sp。的培养液中分离出7种倍半萜烯衍生物，包括类胡萝卜素AF和dendryphiellin A1，以及6-甲基-（2E，4E，6S）辛二烯酸。FT087。通过分析HRMS和NMR光谱数据确定了它们的结构。通过与文献中的CD和旋光数据比较，阐明了类脂类胡萝卜素AD的绝对构型。脂蛋白类固醇AC和E属于倍半萜类的艾美碱类型，而脂蛋白类固醇D和F以及树胶蛋白A1具有三去甲艾美洛芬骨架。测试了所有化合物的抗A2780和顺铂耐药性A2780CisR细胞系，并且树胶状蛋白A1具有中等活性，IC50值分别为6.6和9.1mug / mL。
• Novel Trinor-eremophilanes (Dendryphiellin B, C, and D), Eremophilanes (Dendryphiellin E, F, and G), and Branched C9-Carboxylic Acids (Dendryphiellic Acid A and B) from the Marine DeuteromyceteDendryphiella salina (SUTHERLAND) PUGHet NICOT
  作者：Antonio Guerriero、Michele D'Ambrosio、Vincenzo Cuomo、Fortunato Vanzanella、Francesco Pietra

  DOI：10.1002/hlca.19890720304

  日期：1989.5.3

  investigation of global extracts from cultures of the marine deuteromycete Dendryphiella salina leads to the isolation of three novel trinor-eremophilanes esterified by branched C9-carboxylic acids, dendryphiellin B(= (+)-(1R*,2S*,7R*,8aR*)-1,2,6,7,8,8a-hexahydro-7-hydroxy-1,8a-dimethyl-6-oxonaphthalen-2-yl (6R*, 2E, 4E)-6-hydroxy-6-methylocta-2,4-dienoate; (+)-2), dendryphiellin C (=(+)-(1R*, 2S*, 7R*, 8aR*)-1

  进一步研究了来自海洋氘核菌盐藻Dendryphiella salina的培养物的全球提取物，从而分离出三种被支链C 9-羧酸酯化的新型trinor-eremophilanes ，即dendryphiellin B（=（+）-（1 R *，2 S *，7 R *，8a R *）-1,2,6,7,8,8a-六氢-7-羟基-1,8a-二甲基-6-氧杂萘-2-基（6 R *，2 E，4 E） -6-羟基-6-甲基辛基-2,4-二烯酸酯;（+）- 2），树枝菌素C（=（+）-（1 R *，2 S *，7 R *，8a R*）-1,2,6,7,8,8a-六氢-7-羟基-1,8a-二甲基-6-氧代萘-2-基（6 S，2 E，4 E）-6-甲基辛基-2，4-二羟戊酸酯；（+）- 3））和树状磷脂D（=（+）-（1 R *，2 S *，7 R *，8a R *）-1,2,6,7（8,8a-hexahydro-7
• Synthesis of dendryphiellin C, a trinor-sesquiterpene from a marine source
  作者：Hiroko Akao、Hiromasa Kiyota、Takao Nakajima、Takeshi Kitahara

  DOI：10.1016/s0040-4020(99)00407-x

  日期：1999.6

  Enantioselective synthesis of dendryphiellin C, isolated from cultures of Dendryphiella sarina, has been achieved in a convergent way such as coupling of a C9-branched carboxylic acid 10 with a trinor-eremophilane alcohol 11. The latter was synthesized starting from a chiral building block, (1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 16, which was originally prepared in this group using biochemical transformation as a key step. The synthesis was completed through 12 steps from 16 in overall 2.4% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.