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Peniciadametizine A, a Dithiodiketopiperazine with a Unique Spiro[furan-2,7 '-pyrazino[1,2-b][1,2]oxazine] Skeleton, and a Related Analogue, Peniciadametizine B, from the Marine Sponge-Derived Fungus Penicillium adametzioides
Liu, Yang1,2; Mandi, Attila3; Li, Xiao-Ming1; Meng, Ling-Hong1,2; Kurtan, Tibor3; Wang, Bin-Gui1
2015-06-01
Source PublicationMARINE DRUGS
Volume13Issue:6Pages:3640-3652
SubtypeArticle
AbstractPeniciadametizine A (1); a new dithiodiketopiperazine derivative possessing a unique spiro[furan-2,7'-pyrazino[1,2-b][1,2]oxazine] skeleton, together with a highly oxygenated new analogue, peniciadametizine B (2); as well as two known compounds, brasiliamide A (3); and viridicatumtoxin (4), were isolated and identified from Penicillium adametzioides AS-53, a fungus obtained from an unidentified marine sponge. The unambiguous assignment of the relative and absolute configuration for the spiro center C-2 of compound 1 was solved by the combination of NMR and ECD measurements with Density-Functional Theory (DFT) conformational analysis and Time-Dependent Density-Functional Theory-Electronic Circular Dichroism (TDDFT-ECD) calculations. The spiro[furan-2,7'-pyrazino[1,2-b][1,2]oxazine] skeleton of 1 has not been reported yet among natural products and the biosynthetic pathway for 1 and 2 was discussed. Compounds 1 and 2 showed inhibitory activity against the pathogenic fungus Alternaria brassicae.
KeywordMarine Sponge Endophytic Fungus Penicillium Adametzioides Secondary Metabolites Antifungal Activity
DOI10.3390/md13063640
Indexed BySCI
Language英语
WOS IDWOS:000357279900023
Citation statistics
Cited Times:15[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.qdio.ac.cn/handle/337002/49045
Collection实验海洋生物学重点实验室
海洋生态与环境科学重点实验室
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.Univ Debrecen, 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
Liu, Yang,Mandi, Attila,Li, Xiao-Ming,et al. Peniciadametizine A, a Dithiodiketopiperazine with a Unique Spiro[furan-2,7 '-pyrazino[1,2-b][1,2]oxazine] Skeleton, and a Related Analogue, Peniciadametizine B, from the Marine Sponge-Derived Fungus Penicillium adametzioides[J]. MARINE DRUGS,2015,13(6):3640-3652.
APA Liu, Yang,Mandi, Attila,Li, Xiao-Ming,Meng, Ling-Hong,Kurtan, Tibor,&Wang, Bin-Gui.(2015).Peniciadametizine A, a Dithiodiketopiperazine with a Unique Spiro[furan-2,7 '-pyrazino[1,2-b][1,2]oxazine] Skeleton, and a Related Analogue, Peniciadametizine B, from the Marine Sponge-Derived Fungus Penicillium adametzioides.MARINE DRUGS,13(6),3640-3652.
MLA Liu, Yang,et al."Peniciadametizine A, a Dithiodiketopiperazine with a Unique Spiro[furan-2,7 '-pyrazino[1,2-b][1,2]oxazine] Skeleton, and a Related Analogue, Peniciadametizine B, from the Marine Sponge-Derived Fungus Penicillium adametzioides".MARINE DRUGS 13.6(2015):3640-3652.
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