Literature DB >> 29503481

Absolute Configurations of Griseorhodins A and C.

Humberto E Ortega1, João M Batista2, Weilan G P Melo1, Jon Clardy3, Mônica T Pupo1.   

Abstract

The known antibiotic and cytotoxic compounds griseorhodin A (1) and griseorhodin C (2) were produced in solid culture by Streptomyces puniceus AB10, which was isolated from the leaf-cutter ant Acromyrmex rugosus rugosus. Their absolute configurations were unambiguously established as 6S,6aR,7S,8S and 6R,6aR,7S,8R, respectively, using vibrational circular dichroism (VCD) and density functional theory (DFT) calculations.

Entities:  

Keywords:  Acromyrmex rugosus rugosus; Griseorhodins; Rubromycin; Streptomyces puniceus; Vibrational circular dichroism

Year:  2017        PMID： 29503481      PMCID： PMC5828249          DOI： 10.1016/j.tetlet.2017.11.008

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  8 in total

1.  Inhibition of human telomerase by rubromycins: implication of spiroketal system of the compounds as an active moiety.

Authors:  T Ueno; H Takahashi; M Oda; M Mizunuma; A Yokoyama; Y Goto; Y Mizushina; K Sakaguchi; H Hayashi
Journal:  Biochemistry       Date:  2000-05-23       Impact factor: 3.162

2.  Isolation and structure elucidation of 7,8-dideoxy-6-oxo-griseorhodin C produced by Actinoplanes ianthinogenes.

Authors:  G Panzone; A Trani; P Ferrari; L Gastaldo; L Colombo
Journal:  J Antibiot (Tokyo)       Date:  1997-08       Impact factor: 2.649

Review 3.  Recent advances in the use of vibrational chiroptical spectroscopic methods for stereochemical characterization of natural products.

Authors:  João M Batista; Ewan W Blanch; Vanderlan da Silva Bolzani
Journal:  Nat Prod Rep       Date:  2015-09       Impact factor: 13.423

4.  Purpuromycin, a new antibiotic isolated from Actinoplanes ianthinogenes N. sp.

Authors:  C Coronelli; H Pagani; M R Bardone; G C Lancini
Journal:  J Antibiot (Tokyo)       Date:  1974-03       Impact factor: 2.649

5.  The structure of the antibiotic griseorhodin C.

Authors:  K Eckardt; D Tresselt; W Ihn
Journal:  J Antibiot (Tokyo)       Date:  1978-10       Impact factor: 2.649

Review 6.  Isolation, biological activity, biosynthesis and synthetic studies towards the rubromycin family of natural products.

Authors:  Darcy J Atkinson; Margaret A Brimble
Journal:  Nat Prod Rep       Date:  2015-06       Impact factor: 13.423

7.  Isolation and structure elucidation of a novel griseorhodin.

Authors:  R M Stroshane; J A Chan; E A Rubalcaba; A L Garretson; A A Aszalos; P P Roller
Journal:  J Antibiot (Tokyo)       Date:  1979-03       Impact factor: 2.649

8.  Cleavage of four carbon-carbon bonds during biosynthesis of the griseorhodin a spiroketal pharmacophore.

Authors:  Zeynep Yunt; Kathrin Reinhardt; Aiying Li; Marianne Engeser; Hans-Martin Dahse; Michael Gütschow; Torsten Bruhn; Gerhard Bringmann; Jörn Piel
Journal:  J Am Chem Soc       Date:  2009-02-18       Impact factor: 15.419
  8 in total
  2 in total

1.  Enzymatic spiroketal formation via oxidative rearrangement of pentangular polyketides.

Authors:  Britta Frensch; Thorsten Lechtenberg; Michel Kather; Zeynep Yunt; Martin Betschart; Bernd Kammerer; Steffen Lüdeke; Michael Müller; Jörn Piel; Robin Teufel
Journal:  Nat Commun       Date:  2021-03-04       Impact factor: 14.919

2.  Antifungal compounds from Streptomyces associated with attine ants also inhibit Leishmania donovani.

Authors:  Humberto E Ortega; Leonardo L G Ferreira; Weilan G P Melo; Ana Ligia L Oliveira; René F Ramos Alvarenga; Norberto P Lopes; Tim S Bugni; Adriano D Andricopulo; Mônica T Pupo
Journal:  PLoS Negl Trop Dis       Date:  2019-08-05
  2 in total

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