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Mar. Drugs 2014, 12(11), 5657-5676; doi:10.3390/md12115657

Exploring the Chemodiversity and Biological Activities of the Secondary Metabolites from the Marine Fungus Neosartorya pseudofischeri

1
School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China
2
Guangdong Technology Research Center for Advanced Chinese Medicine, Guangzhou 510006, China
3
School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, China
4
Guangdong Institute of Gastroenterology, Guangzhou 510655, China
5
Guangdong Key Laboratory of Colorectal and Pelvic Floor Diseases, Guangzhou 510655, China
6
The Sixth Affiliated Hospital, Sun Yat-sen University, Guangzhou 510655, China
7
Institute of Chinese Medical Sciences, Guangdong Pharmaceutical University, Guangzhou 510006, China
*
Author to whom correspondence should be addressed.
Received: 15 August 2014 / Revised: 12 November 2014 / Accepted: 17 November 2014 / Published: 24 November 2014
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Abstract

The production of fungal metabolites can be remarkably influenced by various cultivation parameters. To explore the biosynthetic potentials of the marine fungus, Neosartorya pseudofischeri, which was isolated from the inner tissue of starfish Acanthaster planci, glycerol-peptone-yeast extract (GlyPY) and glucose-peptone-yeast extract (GluPY) media were used to culture this fungus. When cultured in GlyPY medium, this fungus produced two novel diketopiperazines, neosartins A and B (1 and 2), together with six biogenetically-related known diketopiperazines,1,2,3,4-tetrahydro-2, 3-dimethyl-1,4-dioxopyrazino[1,2-a]indole (3), 1,2,3,4-tetrahydro-2-methyl-3-methylen e-1,4-dioxopyrazino[1,2-a]indole (4), 1,2,3,4-tetrahydro-2-methyl-1,3,4-trioxopyrazino[1,2-a] indole (5), 6-acetylbis(methylthio)gliotoxin (10), bisdethiobis(methylthio)gliotoxin (11), didehydrobisdethiobis(methylthio)gliotoxin (12) and N-methyl-1H-indole-2-carboxamide (6). However, a novel tetracyclic-fused alkaloid, neosartin C (14), a meroterpenoid, pyripyropene A (15), gliotoxin (7) and five known gliotoxin analogues, acetylgliotoxin (8), reduced gliotoxin (9), 6-acetylbis(methylthio)gliotoxin (10), bisdethiobis(methylthio) gliotoxin (11) and bis-N-norgliovictin (13), were obtained when grown in glucose-containing medium (GluPY medium). This is the first report of compounds 3, 4, 6, 9, 10 and 12 as naturally occurring. Their structures were determined mainly by MS, 1D and 2D NMR data. The possible biosynthetic pathways of gliotoxin-related analogues and neosartin C were proposed. The antibacterial activity of compounds 214 and the cytotoxic activity of compounds 4, 5 and 713 were evaluated. Their structure-activity relationships are also preliminarily discussed. View Full-Text
Keywords: marine fungus; Neosartorya pseudofischeri; neosartin; diketopiperazine; antibacterial activity; cytotoxic activity marine fungus; Neosartorya pseudofischeri; neosartin; diketopiperazine; antibacterial activity; cytotoxic 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

Liang, W.-L.; Le, X.; Li, H.-J.; Yang, X.-L.; Chen, J.-X.; Xu, J.; Liu, H.-L.; Wang, L.-Y.; Wang, K.-T.; Hu, K.-C.; Yang, D.-P.; Lan, W.-J. Exploring the Chemodiversity and Biological Activities of the Secondary Metabolites from the Marine Fungus Neosartorya pseudofischeri. Mar. Drugs 2014, 12, 5657-5676.

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