Literature DB >> 17190469

Bionectins A-C, epidithiodioxopiperazines with anti-MRSA activity, from Bionectra byssicola F120.

Chang-Ji Zheng1, Chang-Jin Kim, Kyung Sook Bae, Young-Ho Kim, Won-Gon Kim.   

Abstract

Three new epidithiodioxopiperazine compounds, bionectins A (1), B (2), and C (3), along with a known compound, verticillin D (4), have been isolated from the mycelium of liquid fermentation cultures of the fungus Bionectra byssicola F120. The structures of compounds 1-3 were assigned on the basis of MS and NMR data. Compounds 1 and 2 incorporate a dioxopiperazine moiety with a disulfide bridge in their molecules, while 3 contains a dioxopiperazine ring with two methylsulfanyl groups. Compounds 1 and 2 exhibited antibacterial activity against S. aureus including methicillin-resistant S. aureus (MRSA) and quinolone-resistant S. aureus (QRSA), with MIC values of 10-30 microg/mL, while 3 showed no antibacterial activity even at 100 microg/mL.

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Year:  2006        PMID: 17190469     DOI: 10.1021/np060348t

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


  24 in total

1.  Total synthesis of (+)-gliocladin C enabled by visible-light photoredox catalysis.

Authors:  Laura Furst; Jagan M R Narayanam; Corey R J Stephenson
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-12       Impact factor: 15.336

2.  Cytotoxic epipolythiodioxopiperazine alkaloids from filamentous fungi of the Bionectriaceae.

Authors:  Mario Figueroa; Tyler N Graf; Sloan Ayers; Audrey F Adcock; David J Kroll; Jilai Yang; Steven M Swanson; Ulyana Munoz-Acuna; Esperanza J Carcache de Blanco; Rajesh Agrawal; Mansukh C Wani; Blaise A Darveaux; Cedric J Pearce; Nicholas H Oberlies
Journal:  J Antibiot (Tokyo)       Date:  2012-09-12       Impact factor: 2.649

3.  n→π* Interactions Modulate the Disulfide Reduction Potential of Epidithiodiketopiperazines.

Authors:  Henry R Kilgore; Chase R Olsson; Kyan A D'Angelo; Mohammad Movassaghi; Ronald T Raines
Journal:  J Am Chem Soc       Date:  2020-08-21       Impact factor: 15.419

Review 4.  Epidithiodioxopiperazines. occurrence, synthesis and biogenesis.

Authors:  Timothy R Welch; Robert M Williams
Journal:  Nat Prod Rep       Date:  2014-10       Impact factor: 13.423

5.  Enantioselective total synthesis of plectosphaeroic acid B.

Authors:  Salman Y Jabri; Larry E Overman
Journal:  J Am Chem Soc       Date:  2013-03-06       Impact factor: 15.419

6.  General approach for preparing epidithiodioxopiperazines from trioxopiperazine precursors: enantioselective total syntheses of (+)- and (-)-gliocladine C, (+)-leptosin D, (+)-T988C, (+)-bionectin A, and (+)-gliocladin A.

Authors:  John E DeLorbe; David Horne; Richard Jove; Steven M Mennen; Sangkil Nam; Fang-Li Zhang; Larry E Overman
Journal:  J Am Chem Soc       Date:  2013-03-01       Impact factor: 15.419

7.  Concise Total Synthesis of (+)-Gliocladins B and C.

Authors:  Nicolas Boyer; Mohammad Movassaghi
Journal:  Chem Sci       Date:  2012-03-30       Impact factor: 9.825

8.  Recent developments in the catalytic, asymmetric construction of pyrroloindolines bearing all-carbon quaternary stereocenters.

Authors:  Lindsay M Repka; Sarah E Reisman
Journal:  J Org Chem       Date:  2013-12-02       Impact factor: 4.354

9.  Concise Total Synthesis of (+)-Luteoalbusins A and B.

Authors:  Timothy C Adams; Joshua N Payette; Jaime H Cheah; Mohammad Movassaghi
Journal:  Org Lett       Date:  2015-08-25       Impact factor: 6.005

10.  Concise Total Synthesis of (+)-Bionectins A and C.

Authors:  Alexis Coste; Justin Kim; Timothy C Adams; Mohammad Movassaghi
Journal:  Chem Sci       Date:  2013-08       Impact factor: 9.825

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