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Brocaeloids A-C, 4-Oxoquinoline and Indole Alkaloids with C-2 Reversed Prenylation from the Mangrove-Derived Endophytic Fungus Penicillium brocae
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; Kurtan, T (reprint author), Debrecen Univ Med, Dept Organ Chem, POB 20, H-4010 Debrecen, Hungary.
2014-07-01
Source PublicationEUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Issue19Pages:4029-4036
SubtypeArticle
AbstractThree 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.
KeywordNatural Products Alkaloids Circular Dichroism Density Functional Calculations
Subject AreaChemistry
DOI10.1002/ejoc.201400067
Indexed BySCI ; IC
Language英语
WOS IDWOS:000338018400010
Citation statistics
Cited Times:25[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.qdio.ac.cn/handle/337002/24079
Collection实验海洋生物学重点实验室
Corresponding AuthorKurtan, T (reprint author), Debrecen Univ Med, Dept Organ Chem, POB 20, H-4010 Debrecen, Hungary.
Affiliation1.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
First Author AffilicationKey Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences
Recommended Citation
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.,...&Kurtan, T .(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.
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