Literature DB >> 22050382

Jadomycins derived from the assimilation and incorporation of norvaline and norleucine.

Stephanie N Dupuis1, Thomas Veinot, Susan M A Monro, Susan E Douglas, Raymond T Syvitski, Kerry B Goralski, Sherri A McFarland, David L Jakeman.   

Abstract

Streptomyces venezuelae ISP5230 is recognized for the production of chloramphenicol and the jadomycin family of natural products. The jadomycins are angucycline natural products containing a unique oxazolone ring incorporating an amino acid present in the minimal culture media. Substitution of different amino acids results in products of varying biological activity. Analysis of cultures of S. venezuelae ISP5230 incubated with l- and d-norvaline and l- and d-norleucine indicated that only the d-configured amino acids were incorporated into the natural products. Subsequently, jadomycin DNV and jadomycin DNL were isolated and characterized (titers 4 and 9 mg L(-1), respectively). The compounds were evaluated in the National Cancer Institute cell line cancer growth inhibition and cytotoxicity screens, for antimicrobial activity against selected Gram-positive and Gram-negative bacteria, and as DNA-cleavage agents in vitro.

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Year:  2011        PMID: 22050382     DOI: 10.1021/np200689w

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


  7 in total

Review 1.  A comprehensive review of glycosylated bacterial natural products.

Authors:  Sherif I Elshahawi; Khaled A Shaaban; Madan K Kharel; Jon S Thorson
Journal:  Chem Soc Rev       Date:  2015-11-07       Impact factor: 54.564

2.  Precursor-Directed Generation of Amidine Containing Ammosamide Analogs: Ammosamides E-P.

Authors:  Ende Pan; Nathaniel W Oswald; Aaron G Legako; Janie M Life; Bruce A Posner; John B Macmillan
Journal:  Chem Sci       Date:  2013-01       Impact factor: 9.825

3.  Discovery, Characterization, and Analogue Synthesis of Bohemamine Dimers Generated by Non-enzymatic Biosynthesis.

Authors:  Peng Fu; Aaron Legako; Scott La; John B MacMillan
Journal:  Chemistry       Date:  2016-02-02       Impact factor: 5.236

4.  Biosynthesis and Total Synthesis Studies on The Jadomycin Family of Natural Products.

Authors:  Ehesan U Sharif; George A O'Doherty
Journal:  European J Org Chem       Date:  2012-04

5.  Jadomycin breast cancer cytotoxicity is mediated by a copper-dependent, reactive oxygen species-inducing mechanism.

Authors:  Steven R Hall; Heather L Blundon; Matthew A Ladda; Andrew W Robertson; Camilo F Martinez-Farina; David L Jakeman; Kerry B Goralski
Journal:  Pharmacol Res Perspect       Date:  2015-03

Review 6.  Jadomycins: A potential chemotherapy for multi-drug resistant metastatic breast cancer.

Authors:  Esther P Bonitto; Brendan T McKeown; Kerry B Goralski
Journal:  Pharmacol Res Perspect       Date:  2021-12

7.  Diels-Alder construction of regiodifferentiated meta-amino phenols and derivatives.

Authors:  Marisa G Weaver; Wen-Ju Bai; Stephen K Jackson; Thomas R R Pettus
Journal:  Org Lett       Date:  2014-02-13       Impact factor: 6.005

  7 in total

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