Brocaeloids A-C, 4-Oxoquinoline and Indole Alkaloids with C-2 Reversed Prenylation from the Mangrove-Derived Endophytic Fungus Penicillium brocae
文献类型：期刊论文
| 作者 | Zhang, Peng1,2 ; Meng, Ling-Hong1,2; Mandi, Attila3; Kurtan, Tibor3; Li, Xiao-Ming1; Liu, Yang1,2; Li, Xin1,2; Li, Chun-Shun1; Wang, Bin-Gui1
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| 刊名 | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
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| 出版日期 | 2014-07-01 |
| 期号 | 19页码:4029-4036 |
| 关键词 | Natural products Alkaloids Circular dichroism Density functional calculations |
| 通讯作者 | Kurtan, T (reprint author), Debrecen Univ Med, Dept Organ Chem, POB 20, H-4010 Debrecen, Hungary. |
| 英文摘要 | Three new alkaloids, brocaeloids A-C (1-3), containing C-2 reversed prenylation, were isolated from cultures of Penicillium brocae MA-192, an endophytic fungus obtained from the fresh leaves of the marine mangrove plant Avicennia marina. Their structures were determined on the basis of 1D and 2D NMR spectroscopy as well as by high-resolution mass spectrometry. The absolute configuration of brocaeloid A (1) was established by gas-phase and solution conformational analysis and TDDFT-ECD calculations, which revealed that the fused hetero-ring adopted M-helicity conformation with axial orientation of the C-2 and C-3 substituents. The correct assignment of the hetero-ring conformation was found to be crucial in determining the relative and absolute configuration. Based on ECD calculations, the helicity of the 2,3-dihydroquinoline-4(1H)-one chromophore was correlated with the characteristic ECD transitions, and the resultant helicity rule was found to coincide with that of the chroman-4-one chromophore. X-ray single-crystal analysis of 1 by Cu-K-alpha radiation also confirmed the result of the stereochemical analysis obtained from ECD calculations. Brocaeloid B (2) showed lethality against brine shrimp (Artemia salina) with an LD50 value of 36.7 mu M. |
| 学科主题 | Chemistry |
| 收录类别 | SCI ; IC |
| 语种 | 英语 |
| WOS记录号 | WOS:000338018400010 |
| 源URL | [http://ir.qdio.ac.cn/handle/337002/24079]  |
| 专题 | 海洋研究所_实验海洋生物学重点实验室 |
| 作者单位 | 1.Chinese Acad Sci, Inst Oceanol, Key Lab Expt Marine Biol, Qingdao 266071, Peoples R China 2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 3.Debrecen Univ Med, Dept Organ Chem, H-4010 Debrecen, Hungary |
| 推荐引用方式 GB/T 7714 | Zhang, Peng,Meng, Ling-Hong,Mandi, Attila,et al. Brocaeloids A-C, 4-Oxoquinoline and Indole Alkaloids with C-2 Reversed Prenylation from the Mangrove-Derived Endophytic Fungus Penicillium brocae[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2014(19):4029-4036. |
| APA | Zhang, Peng.,Meng, Ling-Hong.,Mandi, Attila.,Kurtan, Tibor.,Li, Xiao-Ming.,...&Wang, Bin-Gui.(2014).Brocaeloids A-C, 4-Oxoquinoline and Indole Alkaloids with C-2 Reversed Prenylation from the Mangrove-Derived Endophytic Fungus Penicillium brocae.EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(19),4029-4036. |
| MLA | Zhang, Peng,et al."Brocaeloids A-C, 4-Oxoquinoline and Indole Alkaloids with C-2 Reversed Prenylation from the Mangrove-Derived Endophytic Fungus Penicillium brocae".EUROPEAN JOURNAL OF ORGANIC CHEMISTRY .19(2014):4029-4036. |
入库方式： OAI收割
来源：海洋研究所
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