Literature DB >> 35099085

Absolute configuration of cytotoxic anthraquinones from a Brazilian cave soil-derived fungus, Aspergillus sp. SDC28.

Juliana R Gubiani1, Darlon I Bernardi1, Caio C P De Paula2,3, Mirna H R Seleghim2, Antonio G Ferreira4, Andrea N L Batista5, João M Batista6, Lucianne F P Oliveira7, Simone P Lira7, Joanna E Burdette8, Roberto G S Berlinck1.   

Abstract

Microbial strains isolated from extreme and understudied environments, such as caves, are still poorly investigated for the production of bioactive secondary metabolites. Investigation of the ethyl acetate extract from the growth medium produced by the soil-derived fungus Aspergillus sp. SDC28, isolated from a Brazilian cave, yielded two anthraquinones: versicolorin C (1) and versiconol (2). The complete assignment of nuclear magnetic resonance and mass spectroscopic data of 1 and 2 was performed for the first time. Moreover, the yet unreported absolute configuration of both compounds was unambiguously established by analysis of experimental and theoretical electronic circular dichroism data. Vibrational circular dichroism was also applied to confirm the absolute stereochemistry of 2. Compounds 1 and 2 showed cytotoxic activity against human ovarian cancer cells (OVCAR3).
© 2022 Deutsche Pharmazeutische Gesellschaft.

Entities:  

Keywords:  anticancer; aromatic metabolites; extremophiles; polyketides; soil-derived fungus

Mesh:

Substances:

Year:  2022        PMID: 35099085      PMCID: PMC8983557          DOI: 10.1002/ardp.202100441

Source DB:  PubMed          Journal:  Arch Pharm (Weinheim)        ISSN: 0365-6233            Impact factor:   3.751


  12 in total

1.  Bioactive metabolites from the sponge-derived fungus Aspergillus versicolor.

Authors:  Yoon Mi Lee; Huayue Li; Jongki Hong; Hee Young Cho; Kyung Sook Bae; Mi Ae Kim; Dong-Kyoo Kim; Jee H Jung
Journal:  Arch Pharm Res       Date:  2010-02-24       Impact factor: 4.946

2.  High cellulolytic activities in filamentous fungi isolated from an extreme oligotrophic subterranean environment (Catão cave) in Brazil.

Authors:  Caio C P DE Paula; Quimi V Montoya; Lucas A Meirelles; Cristiane S Farinas; André Rodrigues; Mirna H R Seleghim
Journal:  An Acad Bras Cienc       Date:  2019-07-29       Impact factor: 1.753

3.  Effect of versicolorin C, rosenonolactone and cyclopiazonic acid on bovine pancreas deoxyibonuclease.

Authors:  J C Schabort; H A Roberts
Journal:  Biochem Pharmacol       Date:  1971-01       Impact factor: 5.858

4.  Yellow pigments used in rapid identification of aflatoxin-producing Aspergillus strains are anthraquinones associated with the aflatoxin biosynthetic pathway.

Authors:  W Thomas Shier; Yanbin Lao; Terry W J Steele; Hamed K Abbas
Journal:  Bioorg Chem       Date:  2005-11-02       Impact factor: 5.275

5.  Overexpression of an LaeA-like Methyltransferase Upregulates Secondary Metabolite Production in Aspergillus nidulans.

Authors:  Michelle F Grau; Ruth Entwistle; C Elizabeth Oakley; Clay C C Wang; Berl R Oakley
Journal:  ACS Chem Biol       Date:  2019-07-02       Impact factor: 5.100

6.  A metabolic grid among versiconal hemiacetal acetate, versiconol acetate, versiconol and versiconal during aflatoxin biosynthesis.

Authors:  K Yabe; Y Ando; T Hamasaki
Journal:  J Gen Microbiol       Date:  1991-10

7.  [Secondary Metabolites of Fungi of the Usti Section, Genus Aspergillus and Their Application in Chemosystematics].

Authors:  A G Kozlovskii; T V Antipova; V P Zhelifonova; B P Baskunov; N E Ivanushkina; G A Kochkina; S M Ozerskaya
Journal:  Mikrobiologiia       Date:  2017 Mar-Apr

8.  Isolation and Characterization of Two New Metabolites from the Sponge-Derived Fungus Aspergillus sp. LS34 by OSMAC Approach.

Authors:  Wei Li; Lijian Ding; Ning Wang; Jianzhou Xu; Weiyan Zhang; Bin Zhang; Shan He; Bin Wu; Haixiao Jin
Journal:  Mar Drugs       Date:  2019-05-11       Impact factor: 5.118

Review 9.  Exploitation of Aspergillus terreus for the Production of Natural Statins.

Authors:  Mishal Subhan; Rani Faryal; Ian Macreadie
Journal:  J Fungi (Basel)       Date:  2016-04-30

10.  Origin of Cave Fungi.

Authors:  Zhi-Feng Zhang; Peng Zhao; Lei Cai
Journal:  Front Microbiol       Date:  2018-06-28       Impact factor: 5.640

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