sphaeropsidin C methyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: sphaeropsidin C methyl ester
• 英文别名: methyl (4aR,4bR,7R,10aS)-7-ethenyl-4b-hydroxy-1,1,7-trimethyl-9-oxo-3,4,5,6,10,10a-hexahydro-2H-phenanthrene-4a-carboxylate
• 化学式: C₂₁H₃₀O₄
• 分子量: 346.467
• InChiKey: BYODNWRRBVBGDG-LRGNLBRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  sphaeropsidin C 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以5 mg的产率得到sphaeropsidin C methyl ester
  参考文献：
  名称：

  Smardaesidins A–G、Isopimarane 和 20-nor-Isopimarane Diterpenoids 来自 Smardaea sp.，一种苔藓 Ceratodon purpureus 的真菌内生菌 (1)

  摘要：

  五种新的异海松二萜、smardaesidins A–E ( 1 – 5 ) 和两种新的 20- nor- isopimarane 二萜、smardaesidins F ( 6 ) 和 G ( 7 )，以及sphaeropsidins A ( 8 ) 和 C–F ( 10 – 13 ) ) 是从内生真菌菌株Smardaea sp.中分离出来的。AZ0432，存在于苔藓Ceratodon purpureus 的活光合组织中。其中，作为不可分离的异构体混合物获得了smardaesidins B( 2 )和C( 3 )。sphaeropsidin A ( 8 ) 的化学还原提供了 sphaeropsidin B ( 9 ))，而8 的催化氢化产生 7 - O -15,16-四氢球藻素 A ( 14 ) 及其新衍生物 7-羟基-6-氧代异海松- 7-en-20-油酸 ( 15 )。sphaeropsidin

  DOI：

  10.1021/np2000864

文献信息

• <i>In Vitro</i> Antibacterial Activity of Sphaeropsidins and Chemical Derivatives toward <i>Xanthomonas oryzae</i> pv. <i>oryzae</i>, the Causal Agent of Rice Bacterial Blight
  作者：Antonio Evidente、Vittorio Venturi、Marco Masi、Giuliano Degrassi、Alessio Cimmino、Lucia Maddau、Anna Andolfi

  DOI：10.1021/np200625m

  日期：2011.12.27

  Sphaeropsidin A, the main phytotoxin produced by Diplodia cupressi, as well as the two natural analogues sphaeropsidins B and C and 14 derivatives obtained by chemical modifications were assayed for antibacterial activity against Xanthomonas oryzae pv. oryzae, Pseudomonas fuscovaginae, and Burkholderia glumae, the causal agents of severe bacterial rice diseases. The results showed a strong and specific activity of sphaeropsidin A against X. oryzae pv. oryzae, while no activity was observed against the other two pathogens. The results of structure-activity relationship studies showed that structural features important to impart this antibacterial activity are the presence of the C-7 carbonyl group and the hemiketalic lactone functionality. The C-13 vinyl group, the double bond of ring C, and/or the tertiary C-9 hydroxy group, as well as the pimarane arrangement of the tricylic carbon skeleton, were also important for the antibacterial activity. These findings may be useful in designing novel compounds for practical applications in agriculture.
• Studies on structure–activity relationship of sphaeropsidins A–F, phytotoxins produced by Sphaeropsis sapinea f. sp. cupressi
  作者：Lorenzo Sparapano、Giovanni Bruno、Olga Fierro、Antonio Evidente

  DOI：10.1016/j.phytochem.2003.11.006

  日期：2004.1

  Six forms of sphaeropsidins (SA-SF), three- and tetra-cyclic unrearranged pimarane diterpenes produced by Sphaeropsis sapinea f. sp. cupressi, as well as eight derivatives obtained by chemical modification of SA-SC, were assayed for their bioactivity. The effect of each compound on plants which are host or non-host of the pathogen was investigated. Activity on some plant pathogenic fungi was also tested. Some structure-activity relationships have been identified for both phytotoxic and antifungal activity. It appears that the integrity of the tricyclic pimarane system, the preservation of the double bond C(8)-C(14), the tertiary hydroxyl group at C-9, the vinyl group at C-13, and the carboxylic group at C-10 as well as the integrity of the A-ring provide these molecules with non selective phytotoxic and antimycotic activity. (C) 2003 Elsevier Ltd. All rights reserved.

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