sphaeropsidin A | 38991-80-9

• 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 A
• 英文别名: spaeropsidin A；(1R,2R,5R,9S,10S)-5-ethenyl-2,9-dihydroxy-5,11,11-trimethyl-16-oxatetracyclo[7.5.2.01,10.02,7]hexadec-6-ene-8,15-dione
• CAS: 38991-80-9
• 化学式: C₂₀H₂₆O₅
• 分子量: 346.423
• InChiKey: FEKFUWWVNCCROX-SQWSIXGCSA-N

物化性质

• 沸点：
  555.3±50.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  sphaeropsidin A 在 platinum(IV) oxide 、 氢气 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 7-O-15,16-tetrahydrosphaeropsidin A
  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

文献信息

• 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
• Crystal structure and absolute configuration of sphaeropsidin A and its 6-O-p-bromobenzoate
  作者：Marco Masi、Alessio Cimmino、Lucia Maddau、Alexander Kornienko、Angela Tuzi、Antonio Evidente

  DOI：10.1016/j.tetlet.2016.08.098

  日期：2016.10

  sphaeropsidin A was confirmed by X-ray analysis of the toxin and its 6-O-p-bromobenzoyl derivative. Sphaeropsidin A is a tetracyclic pimarane diterpene produced by different pathogens of forest plants belonging to Diplodia spp. This compound has been long known for its phytotoxic, antimicrobial, and insecticidal activities and, more recently, studied for its promising activity against drug-resistant melanoma and

  通过毒素和其6- O - p-溴苯甲酰基衍生物的X射线分析证实了鞘菌素A的绝对构型。Sphaeropsidin A是由森林植物属于不同病原体产生四环海松烷二萜二孢spp。长期以来，这种化合物因其具有植物毒性，抗微生物和杀虫活性而广为人知，最近又因其对耐药性黑色素瘤和肾癌的有效活性而受到研究。这些研究表明，sphaeropsidin A可以通过调节离子转运蛋白的活性来克服癌细胞中的凋亡和多药耐药性，这是一种新兴的癌症治疗方法。鞘脂菌素的X射线晶体结构的可用性可以促进其进一步的化学和生物学研究，以寻求其作为抗癌药的发展。
• 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
• Aspergillus candidus is a newly recognized source of sphaeropsidin A: Isolation, semi-synthetic derivatization and anticancer evaluation
  作者：Yan Li、Robert Scott、Annie R. Hooper、Geoffrey A. Bartholomeusz、Alexander Kornienko、Gerald F. Bills

  DOI：10.1016/j.bmcl.2017.11.001

  日期：2017.12

  This report details a search for alternative strains that produce the diterpenoid sphaeropsidin A (SphA) among A. candidus strains from the USDA Northern Regional Research Laboratories Culture Collection. We identified two strains that produced SphA using a limited set of test media. An initial scaled-up fermentation of NRRL 313 and isolation effort led to the procurement of sufficient quantities of SphA to prepare five semi-synthetic analogues (1-5) and evaluate their anticancer effects against glioblastoma cells D423 and Gli56 grown in 2D and 3D cultures. Although, the effectiveness of the synthetic analogues varied depending on the cell line and the type of cell culture, compound 5, bearing an aromatic ring at C16, displayed a stronger toxicity towards both D423 and Gli56 cell lines in 2D cultures and D423 spheroids in 3D culture than either SphA or compounds 1-4. (C) 2017 Published by Elsevier Ltd.
• 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