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Mar. Drugs 2015, 13(6), 3640-3652; 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

1
Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, China
2
University of Chinese Academy of Sciences, Yuquan Road 19A, Beijing 100049, China
3
Department of Organic Chemistry, University of Debrecen, P.O. Box 20, Debrecen 4010, Hungary
*
Authors to whom correspondence should be addressed.
Academic Editor: Johannes F. Imhoff
Received: 28 April 2015 / Revised: 24 May 2015 / Accepted: 27 May 2015 / Published: 5 June 2015
(This article belongs to the Special Issue Bioactive Compounds from Marine Fungi)
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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. View Full-Text
Keywords: marine sponge; endophytic fungus; Penicillium adametzioides; secondary metabolites; antifungal activity marine sponge; endophytic fungus; Penicillium adametzioides; secondary metabolites; antifungal activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Liu, Y.; Mándi, A.; Li, X.-M.; Meng, L.-H.; Kurtán, T.; Wang, B.-G. 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. Mar. Drugs 2015, 13, 3640-3652.

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