Literature DB >> 19245260

Cottoquinazoline A and cotteslosins A and B, metabolites from an Australian marine-derived strain of Aspergillus versicolor.

Leith J Fremlin1, Andrew M Piggott, Ernest Lacey, Robert J Capon.   

Abstract

An Australian marine-derived isolate of Aspergillus versicolor (MST-MF495) yielded the known fungal metabolites sterigmatocystin, violaceol I, violaceol II, diorcinol, (-)-cyclopenol, and viridicatol, along with a new alkaloid, cottoquinazoline A (1), and two new cyclopentapeptides, cotteslosins A (2) and B (3). Structures for 1-3 and the known compounds were determined by spectroscopic analysis. The absolute configurations of 1-3 were addressed by chemical degradation and application of the C(3) Marfey's method. The use of "cellophane raft" high-nutrient media as a device for up-regulating secondary metabolite diversity in marine-derived fungi is discussed. The antibacterial properties displayed by A. versicolor (MST-MF495) were attributed to the phenols violaceol I, violaceol II, and diorcinol, while cotteslosins 2 and 3 were identified as weak cytotoxic agents.

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Year:  2009        PMID: 19245260     DOI: 10.1021/np800777f

Source DB:  PubMed          Journal:  J Nat Prod        ISSN: 0163-3864            Impact factor:   4.050


  38 in total

1.  Molecular genetic analysis of the orsellinic acid/F9775 gene cluster of Aspergillus nidulans.

Authors:  James F Sanchez; Yi-Ming Chiang; Edyta Szewczyk; Ashley D Davidson; Manmeet Ahuja; C Elizabeth Oakley; Jin Woo Bok; Nancy Keller; Berl R Oakley; Clay C C Wang
Journal:  Mol Biosyst       Date:  2009-12-16

Review 2.  Marine-derived Aspergillus species as a source of bioactive secondary metabolites.

Authors:  Yoon Mi Lee; Min Jeong Kim; Huayue Li; Ping Zhang; Baoquan Bao; Ka Jeong Lee; Jee H Jung
Journal:  Mar Biotechnol (NY)       Date:  2013-05-25       Impact factor: 3.619

Review 3.  Oxidative Cyclization in Natural Product Biosynthesis.

Authors:  Man-Cheng Tang; Yi Zou; Kenji Watanabe; Christopher T Walsh; Yi Tang
Journal:  Chem Rev       Date:  2016-12-12       Impact factor: 60.622

4.  Comparative genomics reveals high biological diversity and specific adaptations in the industrially and medically important fungal genus Aspergillus.

Authors:  Ronald P de Vries; Robert Riley; Ad Wiebenga; Guillermo Aguilar-Osorio; Sotiris Amillis; Cristiane Akemi Uchima; Gregor Anderluh; Mojtaba Asadollahi; Marion Askin; Kerrie Barry; Evy Battaglia; Özgür Bayram; Tiziano Benocci; Susanna A Braus-Stromeyer; Camila Caldana; David Cánovas; Gustavo C Cerqueira; Fusheng Chen; Wanping Chen; Cindy Choi; Alicia Clum; Renato Augusto Corrêa Dos Santos; André Ricardo de Lima Damásio; George Diallinas; Tamás Emri; Erzsébet Fekete; Michel Flipphi; Susanne Freyberg; Antonia Gallo; Christos Gournas; Rob Habgood; Matthieu Hainaut; María Laura Harispe; Bernard Henrissat; Kristiina S Hildén; Ryan Hope; Abeer Hossain; Eugenia Karabika; Levente Karaffa; Zsolt Karányi; Nada Kraševec; Alan Kuo; Harald Kusch; Kurt LaButti; Ellen L Lagendijk; Alla Lapidus; Anthony Levasseur; Erika Lindquist; Anna Lipzen; Antonio F Logrieco; Andrew MacCabe; Miia R Mäkelä; Iran Malavazi; Petter Melin; Vera Meyer; Natalia Mielnichuk; Márton Miskei; Ákos P Molnár; Giuseppina Mulé; Chew Yee Ngan; Margarita Orejas; Erzsébet Orosz; Jean Paul Ouedraogo; Karin M Overkamp; Hee-Soo Park; Giancarlo Perrone; Francois Piumi; Peter J Punt; Arthur F J Ram; Ana Ramón; Stefan Rauscher; Eric Record; Diego Mauricio Riaño-Pachón; Vincent Robert; Julian Röhrig; Roberto Ruller; Asaf Salamov; Nadhira S Salih; Rob A Samson; Erzsébet Sándor; Manuel Sanguinetti; Tabea Schütze; Kristina Sepčić; Ekaterina Shelest; Gavin Sherlock; Vicky Sophianopoulou; Fabio M Squina; Hui Sun; Antonia Susca; Richard B Todd; Adrian Tsang; Shiela E Unkles; Nathalie van de Wiele; Diana van Rossen-Uffink; Juliana Velasco de Castro Oliveira; Tammi C Vesth; Jaap Visser; Jae-Hyuk Yu; Miaomiao Zhou; Mikael R Andersen; David B Archer; Scott E Baker; Isabelle Benoit; Axel A Brakhage; Gerhard H Braus; Reinhard Fischer; Jens C Frisvad; Gustavo H Goldman; Jos Houbraken; Berl Oakley; István Pócsi; Claudio Scazzocchio; Bernhard Seiboth; Patricia A vanKuyk; Jennifer Wortman; Paul S Dyer; Igor V Grigoriev
Journal:  Genome Biol       Date:  2017-02-14       Impact factor: 13.583

Review 5.  Short pathways to complexity generation: fungal peptidyl alkaloid multicyclic scaffolds from anthranilate building blocks.

Authors:  Christopher T Walsh; Stuart W Haynes; Brian D Ames; Xue Gao; Yi Tang
Journal:  ACS Chem Biol       Date:  2013-06-04       Impact factor: 5.100

Review 6.  Biologically active quinoline and quinazoline alkaloids part II.

Authors:  Xiao-Fei Shang; Susan L Morris-Natschke; Guan-Zhou Yang; Ying-Qian Liu; Xiao Guo; Xiao-Shan Xu; Masuo Goto; Jun-Cai Li; Ji-Yu Zhang; Kuo-Hsiung Lee
Journal:  Med Res Rev       Date:  2018-02-27       Impact factor: 12.944

7.  Secoemestrin D, a cytotoxic epitetrathiodioxopiperizine, and emericellenes A-E, five sesterterpenoids from Emericella sp. AST0036, a fungal endophyte of Astragalus lentiginosus1.

Authors:  Ya-Ming Xu; Patricia Espinosa-Artiles; Mangping X Liu; A Elizabeth Arnold; A A Leslie Gunatilaka
Journal:  J Nat Prod       Date:  2013-11-19       Impact factor: 4.050

Review 8.  Development of novel drugs from marine surface associated microorganisms.

Authors:  Anahit Penesyan; Staffan Kjelleberg; Suhelen Egan
Journal:  Mar Drugs       Date:  2010-03-01       Impact factor: 5.118

9.  Five sesquiterpenoids from a marine-derived fungus Aspergillus sp. isolated from a gorgonian Dichotella gemmacea.

Authors:  Mei-Yan Wei; Chang-Yun Wang; Qing-Ai Liu; Chang-Lun Shao; Zhi-Gang She; Yong-Cheng Lin
Journal:  Mar Drugs       Date:  2010-03-29       Impact factor: 5.118

10.  Complexity generation in fungal peptidyl alkaloid biosynthesis: a two-enzyme pathway to the hexacyclic MDR export pump inhibitor ardeemin.

Authors:  Stuart W Haynes; Xue Gao; Yi Tang; Christopher T Walsh
Journal:  ACS Chem Biol       Date:  2013-02-06       Impact factor: 5.100

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