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Mar Drugs. 2015 Jun 5;13(6):3640-52. doi: 10.3390/md13063640.

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.

Author information

1
Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, China. buckuper@163.com.
2
University of Chinese Academy of Sciences, Yuquan Road 19A, Beijing 100049, China. buckuper@163.com.
3
Department of Organic Chemistry, University of Debrecen, P.O. Box 20, Debrecen 4010, Hungary. mandia@delfin.klte.hu.
4
Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, China. lixmqd@aliyun.com.
5
Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, China. m8545303@163.com.
6
University of Chinese Academy of Sciences, Yuquan Road 19A, Beijing 100049, China. m8545303@163.com.
7
Department of Organic Chemistry, University of Debrecen, P.O. Box 20, Debrecen 4010, Hungary. kurtan.tibor@science.unideb.hu.
8
Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, China. wangbg@ms.qdio.ac.cn.

Abstract

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.

KEYWORDS:

Penicillium adametzioides; antifungal activity; endophytic fungus; marine sponge; secondary metabolites

PMID:
26058014
PMCID:
PMC4483649
DOI:
10.3390/md13063640
[Indexed for MEDLINE]
Free PMC Article

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