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

被引：52

作者：

Liu, Yang ^{[1
,2
]}

Mandi, Attila ^{[3
]}

Li, Xiao-Ming ^{[1
]}

Meng, Ling-Hong ^{[1
,2
]}

Kurtan, Tibor ^{[3
]}

Wang, Bin-Gui ^{[1
]}

机构：

[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] Univ Debrecen, Dept Organ Chem, H-4010 Debrecen, Hungary

来源：

MARINE DRUGS | 2015年 / 13卷 / 06期

基金：

新加坡国家研究基金会;

关键词：

marine sponge; endophytic fungus; Penicillium adametzioides; secondary metabolites; antifungal activity; ABSOLUTE-CONFIGURATION; ASPIROCHLORINE; MACROLIDES; GLIOVIRIN;

D O I：

10.3390/md13063640

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Peniciadametizine 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.

引用

页码：3640 / 3652

页数：13