Literature DB >> 24116376

A new diketopiperazine alkaloid from Aspergillus oryzae.

Mohamed Shaaban1, Mohammad Magdy El-Metwally, Hamdi Nasr.   

Abstract

Investigation of bioactive secondary metabolites from terrestrial Aspergillus oryzae sp. MMAO1 using M2 medium afforded a new diketopiperazine alkaloid, 7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione (1a), containing the unusual amino acid L-6,8-dihydroxy-7-methoxyphenylalanine. This was co-isolated with ditryptophenaline (2), cyclo-(Tryp,Tyr) (4), cyclo-(Pro,Val), α-cyclopiazonic acid (3), kojic acid and uridine. Re-cultivation of the fungal strain on Dox medium led to the production of bisdethio(bismethylthio)gliotoxin (5), pseurotin A (6) along with linoleic acid, α-cyclopiazonic acid (3) and kojic acid. The chemical structure of the new diketopiperazine alkaloid including the relative configuration was determined by 1D and 2D NMR spectroscopy and HR-ESI-MS spectrometry, and by comparison with the related literature. The new alkaloid (1a) showed no antimicrobial activity or cytotoxicity against brine shrimps.

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Year:  2013        PMID： 24116376     DOI： 10.1080/14786419.2013.841687

Source DB:  PubMed          Journal:  Nat Prod Res        ISSN： 1478-6419            Impact factor:   2.861


  5 in total

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

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Journal:  Genome Biol       Date:  2017-02-14       Impact factor: 13.583

Review 2.  Safety of the fungal workhorses of industrial biotechnology: update on the mycotoxin and secondary metabolite potential of Aspergillus niger, Aspergillus oryzae, and Trichoderma reesei.

Authors:  Jens C Frisvad; Lars L H Møller; Thomas O Larsen; Ravi Kumar; José Arnau
Journal:  Appl Microbiol Biotechnol       Date:  2018-10-06       Impact factor: 4.813

Review 3.  Structural Diversity and Biological Activities of the Cyclodipeptides from Fungi.

Authors:  Xiaohan Wang; Yuying Li; Xuping Zhang; Daowan Lai; Ligang Zhou
Journal:  Molecules       Date:  2017-11-23       Impact factor: 4.411

4.  Pseurotin A Inhibits Osteoclastogenesis and Prevents Ovariectomized-Induced Bone Loss by Suppressing Reactive Oxygen Species.

Authors:  Kai Chen; Pengcheng Qiu; Yu Yuan; Lin Zheng; Jianbo He; Chao Wang; Qiang Guo; Jacob Kenny; Qian Liu; Jinmin Zhao; Junhao Chen; Jennifer Tickner; Shunwu Fan; Xianfeng Lin; Jiake Xu
Journal:  Theranostics       Date:  2019-02-28       Impact factor: 11.556

5.  Oryzines A & B, Maleidride Congeners from Aspergillus oryzae and Their Putative Biosynthesis.

Authors:  Zahida Wasil; Eric Kuhnert; Thomas J Simpson; Russell J Cox
Journal:  J Fungi (Basel)       Date:  2018-08-13
  5 in total

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