title: 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.
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.
authors.affiliation: Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, China. buckuper@163.com.|University of Chinese Academy of Sciences, Yuquan Road 19A, Beijing 100049, China. buckuper@163.com.
authors.forename: Yang
authors.initials: Y
authors.lastname: Liu
authors.affiliation: Department of Organic Chemistry, University of Debrecen, P.O. Box 20, Debrecen 4010, Hungary. mandia@delfin.klte.hu.
authors.forename: Attila
authors.initials: A
authors.lastname: Mándi
authors.affiliation: Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, China. lixmqd@aliyun.com.
authors.forename: Xiao-Ming
authors.initials: XM
authors.lastname: Li
authors.affiliation: Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, China. m8545303@163.com.|University of Chinese Academy of Sciences, Yuquan Road 19A, Beijing 100049, China. m8545303@163.com.
authors.forename: Ling-Hong
authors.initials: LH
authors.lastname: Meng
authors.affiliation: Department of Organic Chemistry, University of Debrecen, P.O. Box 20, Debrecen 4010, Hungary. kurtan.tibor@science.unideb.hu.
authors.forename: Tibor
authors.initials: T
authors.lastname: Kurtán
authors.affiliation: Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, China. wangbg@ms.qdio.ac.cn.
authors.forename: Bin-Gui
authors.initials: BG
authors.lastname: Wang
mesh_terms: D000528:Alternaria / Q000187:drug effects; D000818:Animals; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D048588:Benzoxazines / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002942:Circular Dichroism; D054659:Diketopiperazines / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D010407:Penicillium / Q000737:chemistry* / Q000302:isolation & purification; D011161:Porifera / Q000382:microbiology*; D013141:Spiro Compounds / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: D000935:Antifungal Agents; D048588:Benzoxazines; D054659:Diketopiperazines; D013141:Spiro Compounds; C000605317:peniciadametizine A; C000605318:peniciadametizine B
keywords: Penicillium adametzioides; antifungal activity; endophytic fungus; marine sponge; secondary metabolites