halymecin F | 1592582-88-1

• 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: halymecin F
• 英文别名: Halymecin F；(3R,5R)-5-[(3R,5R)-3-acetyloxy-5-[(3R,5R)-5-[(3R,5R)-5-acetyloxy-3-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxydecanoyl]oxy-3-hydroxydecanoyl]oxydecanoyl]oxy-3-hydroxydecanoic acid
• CAS: 1592582-88-1
• 化学式: C₅₀H₈₈O₂₀
• 分子量: 1009.24
• InChiKey: FLWMIXBALDGGQL-FQHOZYHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  70
• 可旋转键数：
  45
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  309
• 氢给体数：
  7
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  halymecin F 在 盐酸 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以4.2 mg的产率得到(4R,6R)-4-hydroxy-6-pentyltetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  Antimicrobial Activities of Novel Mannosyl Lipids Isolated from the Biocontrol Fungus Simplicillium lamellicola BCP against Phytopathogenic Bacteria

  摘要：

  The antagonistic fungus Simplicillium lamellicola BCP has been developed as a microbial biopesticide that effectively controls the development of various plant diseases caused by both pathogenic bacteria and pathogenic fungi. Antibacterial bioassay-directed fractionation was used to isolate mannosyl lipids from S. lamellicola BCP, and the structures of these compounds were elucidated using spectral analysis and chemical degradation. Three novel mannosyl lipids were characterized and identified as halymecins F and G and (3R,5R)-3-O-beta-D-mannosyl-3,5-dihydrodecanoic acid. Massoia lactone and (3R, 512)-3-hydroxydecan-5-olide were also isolated from S. lamellicola BCP. The three novel compounds inhibited the growth of the majority of phytopathogenic bacteria that were tested, and halymecin F displayed the strongest antibacterial activity. Agrobacterium tumefaciens was the most sensitive to the three novel compounds, with IC50 values ranging from 1.58 to 24.8 mu g/mL. The ethyl acetate extract of the fermentation broth from the antagonistic fungus effectively reduced the bacterial wilt caused by Ralstonia solanacearum on tomato seedlings. These results indicate that S. lamellicola BCP suppresses the development of plant bacterial diseases through the production of antibacterial metabolites.

  DOI：

  10.1021/jf500361e