sphaeropsidin B | 39022-38-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: sphaeropsidin B
• 英文别名: spaeropsidin B；(1R,2R,5R,8R,9S,10S)-5-ethenyl-2,8,9-trihydroxy-5,11,11-trimethyl-16-oxatetracyclo[7.5.2.01,10.02,7]hexadec-6-en-15-one
• CAS: 39022-38-3
• 化学式: C₂₀H₂₈O₅
• 分子量: 348.439
• InChiKey: XJXDJAQAAAVDCT-RHOFUAETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  sphaeropsidin B 在 sodium periodate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (1R,4R,3'aS,7'aR)-2-Formyl-4,4',4'-trimethyl-3'-oxo-4-vinyl-hexahydro-spiro[cyclohex-2-ene-1,1'-isobenzofuran]-7'a-carboxylic acid
  参考文献：
  名称：

  In Vitro Antibacterial Activity of Sphaeropsidins and Chemical Derivatives toward Xanthomonas oryzae pv. oryzae, the Causal Agent of Rice Bacterial Blight

  摘要：

  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.

  DOI：

  10.1021/np200625m
• 作为产物：
  描述：

  sphaeropsidin A 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以10.3 mg的产率得到sphaeropsidin B
  参考文献：
  名称：

  环戊二酸，seiridin和sphaeropsidin A作为真菌性植物毒素，以及对埃及伊蚊（Diptera：Culicidae）的杀幼虫和叮咬威慑作用：结构与活性的关系。

  摘要：

  埃及伊蚊是导致登革热（人类最具破坏力的疾病之一）的虫媒病毒的主要载体。通过对真菌植物毒素的初步筛选，评估了环paldic acid（1），seiridin（2），sphaeropsidin A（4）和papyillillic acid（5）的抗Ae杀虫力和杀幼虫活性。由于化合物1、2、4和5表现出蚊咬性的威慑活性，而化合物1和4表现出杀幼虫活性，因此对这些毒素进行了进一步的结构活性关系研究。在耐咬性生物测定中，环戊酸1F的1、2、4和5、3,8-二丹酰hydr，环己酸A的5-叠氮戊酸1G，环戊酸的还原衍生物1 H，异丝氨酸（3） ，2'-O-乙酰丝氨酸（2A），2'-氧丝氨酸（2C），6-O-乙酰球菌素A（4A），8 14-甲基香豆素A甲酯（4B）和香豆素B（4C）的活性高于溶剂对照。鞘菌素B（4C）是活性最高的化合物，其次是2A，而其他化合物的活性较低。化合物4C的防咬活性在统计学上与D

  DOI：

  10.1002/cbdv.201200358

文献信息

• Smardaesidins A–G, Isopimarane and 20-<i>nor</i>-Isopimarane Diterpenoids from Smardaea sp., a Fungal Endophyte of the Moss Ceratodon purpureus
  作者：Xiao-Ning Wang、Bharat P. Bashyal、E. M. Kithsiri Wijeratne、Jana M. U’Ren、Manping X. Liu、Malkanthi K. Gunatilaka、A. Elizabeth Arnold、A. A. Leslie Gunatilaka

  DOI：10.1021/np2000864

  日期：2011.10.28

  methyl ester (17), respectively. Methylation of 10 yielded sphaeropsidin C methyl ester (18). The planar structures and relative configurations of the new compounds 1–7 and 15 were elucidated using MS and 1D and 2D NMR experiments, while the absolute configurations of the stereocenters of 4 and 6–8 were assigned using a modified Mosher’s ester method, CD spectra, and comparison of specific rotation data

  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
• Structures of fungal diterpene antibiotics LL-S491.beta. and -.gamma.
  作者：G. A. Ellestad、M. P. Kunstmann、P. Mirando、G. O. Morton

  DOI：10.1021/ja00772a054

  日期：1972.8
• 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.
• Cyclopaldic Acid, Seiridin, and Sphaeropsidin A as Fungal Phytotoxins, and Larvicidal and Biting Deterrents against<i>Aedes aegypti</i>(Diptera: Culicidae): StructureActivity Relationships
  作者：Alessio Cimmino、Anna Andolfi、Fabiana Avolio、Abbas Ali、Nurhayat Tabanca、Ikhlas A. Khan、Antonio Evidente

  DOI：10.1002/cbdv.201200358

  日期：2013.7

  mosquito biting deterrent activities and 1 and 4 demonstrated larvicidal activities, further structureactivity relationship studies were initiated on these toxins. In biting-deterrence bioassays, 1, 2, 4, and 5, 3,8-didansylhydrazone of cyclopaldic acid, 1F, 5-azidopentanoate of cyclopaldic acid A, 1G, the reduced derivative of cyclopaldic acid, 1 H, isoseiridin (3), 2'-O-acetylseiridin (2A), 2'-oxoseiridin

  埃及伊蚊是导致登革热（人类最具破坏力的疾病之一）的虫媒病毒的主要载体。通过对真菌植物毒素的初步筛选，评估了环paldic acid（1），seiridin（2），sphaeropsidin A（4）和papyillillic acid（5）的抗Ae杀虫力和杀幼虫活性。由于化合物1、2、4和5表现出蚊咬性的威慑活性，而化合物1和4表现出杀幼虫活性，因此对这些毒素进行了进一步的结构活性关系研究。在耐咬性生物测定中，环戊酸1F的1、2、4和5、3,8-二丹酰hydr，环己酸A的5-叠氮戊酸1G，环戊酸的还原衍生物1 H，异丝氨酸（3） ，2'-O-乙酰丝氨酸（2A），2'-氧丝氨酸（2C），6-O-乙酰球菌素A（4A），8 14-甲基香豆素A甲酯（4B）和香豆素B（4C）的活性高于溶剂对照。鞘菌素B（4C）是活性最高的化合物，其次是2A，而其他化合物的活性较低。化合物4C的防咬活性在统计学上与D
• <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.