neomacrophorin III | 1558036-26-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: neomacrophorin III
• 英文别名: Neomacrophorin III；[(1S,2R,6S)-6-[[(1S,4aR,6R,8aR)-6-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methyl (3S)-3-hydroxybutanoate
• CAS: 1558036-26-2
• 化学式: C₂₆H₃₈O₇
• 分子量: 462.584
• InChiKey: NGHPKQFMKLMMHD-IBVHSBIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲醇 、 neomacrophorin III 、 sodium methylate 生成 (S)-3-羟基丁酸甲酯
  参考文献：
  名称：

  Neomacrophorin I, II, and III, novel drimenyl cyclohexanes with hydroxylated butanoates from Trichoderma sp. 1212-03

  摘要：

  Neomacrophorins I(1), II(2), and III (3) were isolated from the culture broth of Trichoderma sp. 1212-03, which was collected at Shirakami Mountainous area in Japan. Structural analyses disclosed that these resemble known macrophorins but possess axial-hydroxy group at C3 as well as different side chains at C7'. These are diastereomeric forms of macrophorins for 5',6'-epoxide functionality. The NMR analyses suggested their relative configurational relationship between the C1-C15 drimene and C1'-C7' epoxyquinone moieties. ECD spectral discussions verified them particularly for C5',C6'-epoxyquinone (1), C5',C6'-epoxysemiquinone (2 and 3), and 2",3"-dihydroxybutanoate moiety in 1 and 2. The configuration of C3"-stereocenter of 3 was determined by chiral GC MS after converting into methyl (S)-3"-hydroxybutanoate by basic of 3 methanolysis. Biological assays disclosed that 1 induces hyphal branching of Cochliobolus miyabeanus as well as cytotoxicity against human colorectal cancer COLO 201. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.087

文献信息

• Neomacrophorin I, II, and III, novel drimenyl cyclohexanes with hydroxylated butanoates from Trichoderma sp. 1212-03
  作者：Akane Hirose、Hayato Maeda、Akio Tonouchi、Tatsuo Nehira、Masaru Hashimoto

  DOI：10.1016/j.tet.2013.12.087

  日期：2014.2

  Neomacrophorins I(1), II(2), and III (3) were isolated from the culture broth of Trichoderma sp. 1212-03, which was collected at Shirakami Mountainous area in Japan. Structural analyses disclosed that these resemble known macrophorins but possess axial-hydroxy group at C3 as well as different side chains at C7'. These are diastereomeric forms of macrophorins for 5',6'-epoxide functionality. The NMR analyses suggested their relative configurational relationship between the C1-C15 drimene and C1'-C7' epoxyquinone moieties. ECD spectral discussions verified them particularly for C5',C6'-epoxyquinone (1), C5',C6'-epoxysemiquinone (2 and 3), and 2",3"-dihydroxybutanoate moiety in 1 and 2. The configuration of C3"-stereocenter of 3 was determined by chiral GC MS after converting into methyl (S)-3"-hydroxybutanoate by basic of 3 methanolysis. Biological assays disclosed that 1 induces hyphal branching of Cochliobolus miyabeanus as well as cytotoxicity against human colorectal cancer COLO 201. (C) 2014 Elsevier Ltd. All rights reserved.