Novel South African Rare Actinomycete <i>Kribbella</i> <i>speibonae</i> Strain SK5: A Prolific Producer of Hydroxamate Siderophores Including New Dehydroxylated Congeners

Novel South African Rare Actinomycete <i>Kribbella</i> <i>speibonae</i> Strain SK5: A Prolific Producer of Hydroxamate Siderophores Including New Dehydroxylated Congeners

In this paper, we report on the chemistry of the rare South African Actinomycete <i>Kribbella speibonae</i> strain SK5, a prolific producer of hydroxamate siderophores and their congeners. Two new analogues, dehydroxylated desferrioxamines, speibonoxamine <b>1</b> and desoxy-...

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Main Authors: Kojo Sekyi Acquah, Denzil R. Beukes, Digby F. Warner, Paul R. Meyers, Suthananda N. Sunassee, Fleurdeliz Maglangit, Hai Deng, Marcel Jaspars, David W. Gammon
Format: Article
Language:English
Published: MDPI AG 2020-06-01
Series:Molecules
Subjects:
<i>Kribbella</i>
speibonoxamine
siderophore
hydroxamate
molecular networking
mass spectrometry
Online Access:https://www.mdpi.com/1420-3049/25/13/2979
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spelling doaj-bfdfa51ab65e476aaab094dbf0e9a09d2020-11-25T03:55:07ZengMDPI AGMolecules1420-30492020-06-01252979297910.3390/molecules25132979Novel South African Rare Actinomycete <i>Kribbella</i> <i>speibonae</i> Strain SK5: A Prolific Producer of Hydroxamate Siderophores Including New Dehydroxylated CongenersKojo Sekyi Acquah0Denzil R. Beukes1Digby F. Warner2Paul R. Meyers3Suthananda N. Sunassee4Fleurdeliz Maglangit5Hai Deng6Marcel Jaspars7David W. Gammon8Department of Chemistry, University of Cape Town, Rondebosch 7701, South AfricaSchool of Pharmacy, University of the Western Cape, Bellville 7535, South AfricaSAMRC/NHLS/UCT Molecular Mycobacteriology Research Unit & DST/NRF Centre of Excellence for Biomedical TB Research, Department of Pathology, Faculty of Health Sciences, University of Cape Town, Observatory 7925, South AfricaDepartment of Molecular and Cell Biology, University of Cape Town, Rondebosch 7701, South AfricaDepartment of Chemistry, University of Cape Town, Rondebosch 7701, South AfricaCollege of Science, University of the Philippines Cebu, Lahug, Cebu City 6000, PhilippinesMarine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Old Aberdeen AB24 3UE, Scotland, UKMarine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Old Aberdeen AB24 3UE, Scotland, UKDepartment of Chemistry, University of Cape Town, Rondebosch 7701, South AfricaIn this paper, we report on the chemistry of the rare South African Actinomycete <i>Kribbella speibonae</i> strain SK5, a prolific producer of hydroxamate siderophores and their congeners. Two new analogues, dehydroxylated desferrioxamines, speibonoxamine <b>1</b> and desoxy-desferrioxamine D<sub>1 </sub><b>2</b>, have been isolated, together with four known hydroxamates, desferrioxamine D<sub>1</sub> <b>3</b>, desferrioxamine B <b>4</b>, desoxy-nocardamine <b>5</b> and nocardamine <b>6</b>, and a diketopiperazine (DKP) <b>7</b>. The structures of <b>1</b>–<b>7</b> were characterized by the analysis of HRESIMS and 1D and 2D NMR data, as well as by comparison with the relevant literature. Three new dehydroxy desferrioxamine derivatives <b>8</b>–<b>10</b> were tentatively identified in the molecular network of <i>K.</i> <i>speibonae </i>strain SK5 extracts, and structures were proposed based on their MS/MS fragmentation patterns. A plausible <i>spb</i> biosynthetic pathway was proposed. To the best of our knowledge, this is the first report of the isolation of desferrioxamines from the actinobacterial genus <i>Kribbella</i>.https://www.mdpi.com/1420-3049/25/13/2979<i>Kribbella</i>speibonoxaminesiderophorehydroxamatemolecular networkingmass spectrometry
collection DOAJ
language English
format Article
sources DOAJ
author Kojo Sekyi Acquah
Denzil R. Beukes
Digby F. Warner
Paul R. Meyers
Suthananda N. Sunassee
Fleurdeliz Maglangit
Hai Deng
Marcel Jaspars
David W. Gammon
spellingShingle Kojo Sekyi Acquah
Denzil R. Beukes
Digby F. Warner
Paul R. Meyers
Suthananda N. Sunassee
Fleurdeliz Maglangit
Hai Deng
Marcel Jaspars
David W. Gammon
Novel South African Rare Actinomycete <i>Kribbella</i> <i>speibonae</i> Strain SK5: A Prolific Producer of Hydroxamate Siderophores Including New Dehydroxylated Congeners
Molecules
<i>Kribbella</i>
speibonoxamine
siderophore
hydroxamate
molecular networking
mass spectrometry
author_facet Kojo Sekyi Acquah
Denzil R. Beukes
Digby F. Warner
Paul R. Meyers
Suthananda N. Sunassee
Fleurdeliz Maglangit
Hai Deng
Marcel Jaspars
David W. Gammon
author_sort Kojo Sekyi Acquah
title Novel South African Rare Actinomycete <i>Kribbella</i> <i>speibonae</i> Strain SK5: A Prolific Producer of Hydroxamate Siderophores Including New Dehydroxylated Congeners
title_short Novel South African Rare Actinomycete <i>Kribbella</i> <i>speibonae</i> Strain SK5: A Prolific Producer of Hydroxamate Siderophores Including New Dehydroxylated Congeners
title_full Novel South African Rare Actinomycete <i>Kribbella</i> <i>speibonae</i> Strain SK5: A Prolific Producer of Hydroxamate Siderophores Including New Dehydroxylated Congeners
title_fullStr Novel South African Rare Actinomycete <i>Kribbella</i> <i>speibonae</i> Strain SK5: A Prolific Producer of Hydroxamate Siderophores Including New Dehydroxylated Congeners
title_full_unstemmed Novel South African Rare Actinomycete <i>Kribbella</i> <i>speibonae</i> Strain SK5: A Prolific Producer of Hydroxamate Siderophores Including New Dehydroxylated Congeners
title_sort novel south african rare actinomycete <i>kribbella</i> <i>speibonae</i> strain sk5: a prolific producer of hydroxamate siderophores including new dehydroxylated congeners
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2020-06-01
description In this paper, we report on the chemistry of the rare South African Actinomycete <i>Kribbella speibonae</i> strain SK5, a prolific producer of hydroxamate siderophores and their congeners. Two new analogues, dehydroxylated desferrioxamines, speibonoxamine <b>1</b> and desoxy-desferrioxamine D<sub>1 </sub><b>2</b>, have been isolated, together with four known hydroxamates, desferrioxamine D<sub>1</sub> <b>3</b>, desferrioxamine B <b>4</b>, desoxy-nocardamine <b>5</b> and nocardamine <b>6</b>, and a diketopiperazine (DKP) <b>7</b>. The structures of <b>1</b>–<b>7</b> were characterized by the analysis of HRESIMS and 1D and 2D NMR data, as well as by comparison with the relevant literature. Three new dehydroxy desferrioxamine derivatives <b>8</b>–<b>10</b> were tentatively identified in the molecular network of <i>K.</i> <i>speibonae </i>strain SK5 extracts, and structures were proposed based on their MS/MS fragmentation patterns. A plausible <i>spb</i> biosynthetic pathway was proposed. To the best of our knowledge, this is the first report of the isolation of desferrioxamines from the actinobacterial genus <i>Kribbella</i>.
topic <i>Kribbella</i>
speibonoxamine
siderophore
hydroxamate
molecular networking
mass spectrometry
url https://www.mdpi.com/1420-3049/25/13/2979
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