11,11′-O-dimethylelaiophylin | 124528-71-8

• 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: 11,11′-O-dimethylelaiophylin
• 英文别名: 11,11'-O,O-dimethylelaiophylin；11,11'-O-dimethylelaiophylin；(3E,5E,7S,8S,11E,13E,15S,16S)-8,16-bis[(2S,3R,4S)-4-[(2R,4R,5R,6R)-4-[(2R,4S,5S,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-5-ethyl-2-methoxy-6-methyloxan-2-yl]-3-hydroxypentan-2-yl]-7,15-dimethyl-1,9-dioxacyclohexadeca-3,5,11,13-tetraene-2,10-dione
• CAS: 124528-71-8
• 化学式: C₅₆H₉₂O₁₈
• 分子量: 1053.34
• InChiKey: BQBQRISTBZWETD-FLDSCQNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  74
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  248
• 氢给体数：
  6
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  甲醇 、 洋橄榄叶素 反应 480.0h， 生成 11,11′-O-dimethylelaiophylin 、 11-O-methylelaiophylin
  参考文献：
  名称：

  Identification of Elaiophylin Derivatives from the Marine-Derived Actinomycete Streptomyces sp. 7-145 Using PCR-Based Screening

  摘要：

  A PCR-based genetic screening experiment targeting the dTDP-glucose-4,6-dehydratase gene revealed that a marine sediment-derived strain, Streptomyces sp. 7-145, had the potential to produce glycosidic antibiotics. Chemical investigation of culture extracts of this strain yielded two new 6-deoxyhexose-containing antibiotics, 11',12'-dehydroelaiophylin (1) and 11,11'-O-dimethyl-14'-deethyl-14'-methylelaiophylin (2), together with four known elaiophylin analogues (3-6). Their structures were determined by extensive NMR, MS, and CD analyses. Compounds 1, 3, 4, and 6 showed good antibacterial activity against methicillin-resistant Staphylococcus aureus and vancomycin-resistant enterococci pathogens.

  DOI：

  10.1021/np4006794

文献信息

• Identification of Elaiophylin Skeletal Variants from the Indonesian <i>Streptomyces</i> sp. ICBB 9297
  作者：Yan Sheng、Phillip W. Lam、Salmah Shahab、Dwi Andreas Santosa、Philip J. Proteau、T. Mark Zabriskie、Taifo Mahmud

  DOI：10.1021/acs.jnatprod.5b00752

  日期：2015.11.25

  Four new elaiophylin macrolides (1-4), together with five known elaiophylins (5-9), have been isolated from cultures of the Indonesian soil bacterium Streptomyces sp. ICBB 9297. The new compounds have macrocyclic skeletons distinct from those of the known dimeric elaiophylins in that one or both of the polyketide chains contain(s) an additional pendant methyl group. Further investigations revealed that 1 and 2 were derived from 3 and 4, respectively, during isolation processes. Compounds 1-3 showed comparable antibacterial activity to elaiophylin against Staphylococcus aureus. However, interestingly, only compounds 1 and 3, which contain a pendant methyl group at C-2, showed activity against Mycobacterium smegmatis, whereas compound 2, which has two pendant methyl groups at C-2 and C-2', and the known elaiophylin analogues (5-7), which lack pendant methyl groups at C-2 and/or C-2', showed no activity. The production of 3 and 4 in strain ICBB 9297 indicates that one of the acyltransferase (AT) domains in the elaiophylin polyketide synthases (PKSs) can recruit both malonyl-CoA and methylmalonyl-CoA as substrates. Bioinformatic analysis of the AT domains of the elaiophylin PKSs revealed that the ela_AT7 domain contains atypical active site amino acid residues, distinct from those conserved in malonyl-CoA- or methylmalonyl-CoA-specific ATs.
• Identification of Elaiophylin Derivatives from the Marine-Derived Actinomycete <i>Streptomyces</i> sp. 7-145 Using PCR-Based Screening
  作者：Chunyan Wu、Yi Tan、Maoluo Gan、Yiguang Wang、Yan Guan、Xinxin Hu、Hongxia Zhou、Xiaoya Shang、Xuefu You、Zhaoyong Yang、Chunling Xiao

  DOI：10.1021/np4006794

  日期：2013.11.22

  A PCR-based genetic screening experiment targeting the dTDP-glucose-4,6-dehydratase gene revealed that a marine sediment-derived strain, Streptomyces sp. 7-145, had the potential to produce glycosidic antibiotics. Chemical investigation of culture extracts of this strain yielded two new 6-deoxyhexose-containing antibiotics, 11',12'-dehydroelaiophylin (1) and 11,11'-O-dimethyl-14'-deethyl-14'-methylelaiophylin (2), together with four known elaiophylin analogues (3-6). Their structures were determined by extensive NMR, MS, and CD analyses. Compounds 1, 3, 4, and 6 showed good antibacterial activity against methicillin-resistant Staphylococcus aureus and vancomycin-resistant enterococci pathogens.