2(5H)-Furanone, 5-(acetyloxy)-4-[2-[(1R,2S,4aS,8aS)-1,2,3,4,4a,7,8,8a-octahydro-1,2,4a,5-tetramethyl-1-naphthalenyl]ethyl]-, rel- | 1677679-34-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2(5H)-Furanone, 5-(acetyloxy)-4-[2-[(1R,2S,4aS,8aS)-1,2,3,4,4a,7,8,8a-octahydro-1,2,4a,5-tetramethyl-1-naphthalenyl]ethyl]-, rel-
• 英文别名: [3-[2-[(1S,2R,4aR,8aR)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]ethyl]-5-oxo-2H-furan-2-yl] acetate
• CAS: 1677679-34-3
• 化学式: C₂₂H₃₂O₄
• 分子量: 360.494
• InChiKey: RUWAXMSQGBJERD-DNDIUFHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酸酐 、 16α-hydroxy-cleroda-3,13(14)Z-dien-15,16-olide 在 吡啶 作用下， 以84%的产率得到2(5H)-Furanone, 5-(acetyloxy)-4-[2-[(1R,2S,4aS,8aS)-1,2,3,4,4a,7,8,8a-octahydro-1,2,4a,5-tetramethyl-1-naphthalenyl]ethyl]-, rel-
  参考文献：
  名称：

  Clerodane type diterpene as a novel antifungal agent from Polyalthia longifolia var. pendula

  摘要：

  Bioactivity-guided chemical examination of methanolic extract of leaves of Polyalthia longifolia var. pendula led to the isolation of the active constituent, a diterpene 1 which was identified as 16 alpha-hydroxyderoda-3,13(14)Z-dien-15,16-olide on the basis of its spectral data. Among the tested strains, diterpene 1 was found to exhibit antifungal activities having MIC90 values of 50.3, 100.6 and 201.2 mu M against Candida albicans NCIM3557, Cryptococcus neoformans NCIM3542 (human pathogens) and Neurospora crassa NCIM870 (saprophyte), respectively. Initial, structure activity-relationship (SAR) data generated by synthesizing some derivatives revealed that the double bond between C3-C4 and the free hydroxyl group at C16 are crucial for the antifungal activity of the diterpene 1. The mode of action of 1 in C. albicans is due to compromised cell membrane permeability and also probably due to disruption of cell wall structures. The red blood cell haemolysis of all the compounds (1-4) did not show any significant haemolysis and was found to be less than 15% for all the compounds when tested at highest concentration, i.e. 1200 mu M. Interestingly, all the tested compounds inhibited Y-H transition in dimorphic C albicans NCIM3557 at much lower concentration than their MIC90 values. Determination of ROS generation by diterpene 1 using DCFH-DA and DHR123 (dihydrorhodamine) staining of C albicans NCIM3557 indicated production of intracellular ROS as a mechanism of antifungal activity. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.054

文献信息

• Clerodane type diterpene as a novel antifungal agent from Polyalthia longifolia var. pendula
  作者：Asish K. Bhattacharya、Hemender R. Chand、Jyothis John、Mukund V. Deshpande

  DOI：10.1016/j.ejmech.2015.02.054

  日期：2015.4

  Bioactivity-guided chemical examination of methanolic extract of leaves of Polyalthia longifolia var. pendula led to the isolation of the active constituent, a diterpene 1 which was identified as 16 alpha-hydroxyderoda-3,13(14)Z-dien-15,16-olide on the basis of its spectral data. Among the tested strains, diterpene 1 was found to exhibit antifungal activities having MIC90 values of 50.3, 100.6 and 201.2 mu M against Candida albicans NCIM3557, Cryptococcus neoformans NCIM3542 (human pathogens) and Neurospora crassa NCIM870 (saprophyte), respectively. Initial, structure activity-relationship (SAR) data generated by synthesizing some derivatives revealed that the double bond between C3-C4 and the free hydroxyl group at C16 are crucial for the antifungal activity of the diterpene 1. The mode of action of 1 in C. albicans is due to compromised cell membrane permeability and also probably due to disruption of cell wall structures. The red blood cell haemolysis of all the compounds (1-4) did not show any significant haemolysis and was found to be less than 15% for all the compounds when tested at highest concentration, i.e. 1200 mu M. Interestingly, all the tested compounds inhibited Y-H transition in dimorphic C albicans NCIM3557 at much lower concentration than their MIC90 values. Determination of ROS generation by diterpene 1 using DCFH-DA and DHR123 (dihydrorhodamine) staining of C albicans NCIM3557 indicated production of intracellular ROS as a mechanism of antifungal activity. (C) 2015 Elsevier Masson SAS. All rights reserved.