hamigeromycin A | 1098072-70-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: hamigeromycin A
• 英文别名: (4S,9S,10S,12E)-9,10,18-trihydroxy-15,16-dimethoxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),12,15,17-tetraene-2,8-dione
• CAS: 1098072-70-8
• 化学式: C₂₀H₂₆O₈
• 分子量: 394.422
• InChiKey: INOAIAVUQLBIID-KGVJXOALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  hamigeromycin A 在 10% Pd/C 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (7S,12S,13S)-4,12,13-Trihydroxy-1,2-dimethoxy-7-methyl-7,8,9,10,13,14,15,16-octahydro-12H-6-oxa-benzocyclotetradecene-5,11-dione
  参考文献：
  名称：

  Novel cyclopropyl diketones and 14-membered macrolides from the soil fungus Hamigera avellanea BCC 17816

  摘要：

  Two novel cyclopropyl diketones, hamavellone A (1) and B (2), and two new 14-membered nonaketide macrolactones, hamigeromycin A (3) and B (4), together with six known compounds, 89-250904-F1 (radicicol analogue A, 5), pseurotin A (6), emodin (7), omega-hydroxyemodin (8), and emodin bianthrones (9 and 10) were isolated from the soil fungus Hamigera avellanea BCC 17816. The structures of the new compounds were defined by analysis of NMR and MS data. The absolute stereochemistry of 3 was addressed by chemical correlation to 5. Hamavellone B (2) exhibited antimalarial activity with an IC50 of 5.2 mu g/nnL, whereas it also showed comparable cytotoxicity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.09.077

文献信息

• Hamigeromycins C–G, 14-membered macrolides from the fungus Hamigera avellanea BCC 17816
  作者：Masahiko Isaka、Panida Chinthanom、Surisa Kongthong、Sumalee Supothina、Pataranun Ittiworapong

  DOI：10.1016/j.tet.2009.11.101

  日期：2010.1

  Five new 14-membered macrolides, hamigeromycins C-G, together with the previously described compounds, hamigeromycin A and 89-250904-F1 (radicicol analog A), were isolated from the fungus Hamigera avellanea BCC 17816. Hamigeromycins A, C, D, and E are stereoisomers differing from one another in the absolute configurations of the 4',5'-diol moiety. Hamigeromycins F and G are unusual 5'-keto-analogs, and they are 6'-epimers to each other. The structures and the stereochemistry of the new compounds were deduced by analyses of the NMR spectroscopic and mass spectrometry data in combination with chemical means. (C) 2009 Elsevier Ltd. All rights reserved.