1,4,5,10,13-pentahydroxy-Δ^2,3-protoilludene

• 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: 1,4,5,10,13-pentahydroxy-Δ^2,3-protoilludene
• 英文别名: 1,4,5,10,13-pentahydroxy-Delta2,3-protoilludene；(2R,2aS,4aR,7R,7aS,7bR)-3-(hydroxymethyl)-6,6,7b-trimethyl-2,5,7,7a-tetrahydro-1H-cyclobuta[g]indene-2,2a,4a,7-tetrol
• 化学式: C₁₅H₂₄O₅
• 分子量: 284.353
• InChiKey: LQKHQNLULMMOOE-SCHIXGKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  101
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,4,5,10,13-pentahydroxy-Δ^2,3-protoilludene 、 乙酰辅酶A 、 丙二酰辅酶A-钠盐 在 Armillaria mellea iterative type I polyketide synthase ArmB, N-terminal hexahistidine-tagged protein 作用下， 以 aq. phosphate buffer 为溶剂， 反应 20.0h， 生成 melledonol
  参考文献：
  名称：

  Assembly of Melleolide Antibiotics Involves a Polyketide Synthase with Cross-Coupling Activity

  摘要：

  Little is known about polyketide biosynthesis in mushrooms (basidiomycota). In this study, we investigated the iterative type I polyketide synthase (PKS) ArmB of the tree pathogen Armillaria mellea, a producer of cytotoxic melleolides (i.e., polyketides esterified with various sesquiterpene alcohols). Heterologously produced ArmB showed orsellinic acid (OA) synthase activity in vitro. Further, we demonstrate cross-coupling activity of Arm B, which forms OA esters with various alcohols. Using a tricyclic Armillaria sesquiterpene alcohol, we reconstituted the biosynthesis of melledonol. Intermolecular transesterification reactions may represent a general mechanism of fungal PKSs to create structural diversity of small molecules. Phylogenetic network construction of thioesterase domains of both basidiomycetes and ascomycetes suggests that the fungal nonreducing PKS family has likely evolved from an ancient OA synthase and has gained versatility by adopting Claisen-like cyclase or transferase activity.

  DOI：

  10.1016/j.chembiol.2013.07.009
• 作为产物：
  描述：

  melleolide D 在 水 、 potassium hydroxide 作用下， 反应 48.0h， 生成 1,4,5,10,13-pentahydroxy-Δ^2,3-protoilludene
  参考文献：
  名称：

  Assembly of Melleolide Antibiotics Involves a Polyketide Synthase with Cross-Coupling Activity

  摘要：

  Little is known about polyketide biosynthesis in mushrooms (basidiomycota). In this study, we investigated the iterative type I polyketide synthase (PKS) ArmB of the tree pathogen Armillaria mellea, a producer of cytotoxic melleolides (i.e., polyketides esterified with various sesquiterpene alcohols). Heterologously produced ArmB showed orsellinic acid (OA) synthase activity in vitro. Further, we demonstrate cross-coupling activity of Arm B, which forms OA esters with various alcohols. Using a tricyclic Armillaria sesquiterpene alcohol, we reconstituted the biosynthesis of melledonol. Intermolecular transesterification reactions may represent a general mechanism of fungal PKSs to create structural diversity of small molecules. Phylogenetic network construction of thioesterase domains of both basidiomycetes and ascomycetes suggests that the fungal nonreducing PKS family has likely evolved from an ancient OA synthase and has gained versatility by adopting Claisen-like cyclase or transferase activity.

  DOI：

  10.1016/j.chembiol.2013.07.009

文献信息

• Assembly of Melleolide Antibiotics Involves a Polyketide Synthase with Cross-Coupling Activity
  作者：Gerald Lackner、Markus Bohnert、Jonas Wick、Dirk Hoffmeister

  DOI：10.1016/j.chembiol.2013.07.009

  日期：2013.9

  Little is known about polyketide biosynthesis in mushrooms (basidiomycota). In this study, we investigated the iterative type I polyketide synthase (PKS) ArmB of the tree pathogen Armillaria mellea, a producer of cytotoxic melleolides (i.e., polyketides esterified with various sesquiterpene alcohols). Heterologously produced ArmB showed orsellinic acid (OA) synthase activity in vitro. Further, we demonstrate cross-coupling activity of Arm B, which forms OA esters with various alcohols. Using a tricyclic Armillaria sesquiterpene alcohol, we reconstituted the biosynthesis of melledonol. Intermolecular transesterification reactions may represent a general mechanism of fungal PKSs to create structural diversity of small molecules. Phylogenetic network construction of thioesterase domains of both basidiomycetes and ascomycetes suggests that the fungal nonreducing PKS family has likely evolved from an ancient OA synthase and has gained versatility by adopting Claisen-like cyclase or transferase activity.