sec-butyl orsellinate | 849440-86-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: sec-butyl orsellinate
• 英文别名: Butan-2-yl 2,4-dihydroxy-6-methylbenzoate
• CAS: 849440-86-4
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: ZTELBEKBSVOKRO-UHFFFAOYSA-N

物化性质

• 熔点：
  87-88 °C
• 沸点：
  366.0±22.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  仲丁醇 、 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 sec-butyl orsellinate
  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

• Radical-Scavenging Activity of Orsellinates
  作者：Thiago Inácio Barros Lopes、Roberta Gomes Coelho、Nídia Cristiane Yoshida、Neli Kika Honda

  DOI：10.1248/cpb.56.1551

  日期：——

  Lichens are an important source of phenolic compounds and have been intensively investigated for their biological and pharmacological activities. Lecanoric acid (1), a lichen depside, was isolated from a Parmotrema tinctorum specimen and treated with alcohols to produce orsellinic acid (2) and orsellinates (3) to (9) (2,4-dihydroxy-6-n-methyl benzoates). Free radical scavenging activity of methyl (3), ethyl (4), n-propyl (5), n-butyl (6), iso-propyl (7), sec-butyl (8), tert-butyl (9) orsellinates was evaluated using 2,2′-diphenyl-1-picrylhydrazyl (DPPH) method. Results showed that chain elongation of methyl (3) to n-butyl (6) causes a rise in the antioxidant activity. However, iso-propyl (7) and tert-butyl (9) were more active than the correspondent linear compounds, although sec-butyl (8) was less active among the chain ramified compounds. All the orsellinates were less active than lecanoric acid (1) and orsellinic acid (2). Orcinol (10) and resorcinol (11) were also determined for comparison with activities of orsellinates. Gallic acid (12) was used as control.

  地衣是酚类化合物的重要来源，人们对其生物和药理活性进行了深入研究。从 Parmotrema tinctorum 标本中分离出地衣苷酸 Lecanoric acid (1)，并用醇处理生成 orsellinic acid (2) 和 orsellinates (3) 至 (9)（2,4-二羟基-6-正甲基苯甲酸酯）。采用 2,2′-二苯基-1-苦基肼（DPPH）法评估了橙皮苷酸甲酯（3）、乙酯（4）、正丙酯（5）、正丁酯（6）、异丙酯（7）、仲丁酯（8）和叔丁酯（9）的自由基清除活性。结果表明，甲基（3）链延长为正丁基（6）会导致抗氧化活性上升。不过，异丙基（7）和叔丁基（9）的活性高于相应的线性化合物，但仲丁基（8）的活性在链延伸化合物中较低。所有橙皮苷酸的活性都低于柠檬酸（1）和橙皮苷酸（2）。此外，还测定了 Orcinol (10) 和 resorcinol (11)，以便与 orsellinates 的活性进行比较。没食子酸（12）用作对照。
• 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.