Cyclic heptapeptides with metal binding properties isolated from the fungus Cadophora malorum from Antarctic soil

The Antarctic fungus Cadophora malorum produces previously undescribed cyclic heptapeptides (cadophorin A and B) containing an anthranilic acid residue. The planar structure of these peptides was determined by high-resolution mass spectrometry combined with extensive 1D and 2D NMR spectroscopy. The...

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Published in:Natural Products and Bioprospecting
Main Authors: Donalle, Guidmar C., Martorell, María Martha, Siless, Gastón E., Ruberto, Lucas, Cabrera, Gabriela M.
Format: Text
Language:English
Published: Springer Nature Singapore 2022
Subjects:
Original Article
Allo
Antarctic
The Antarctic
Antarc*
Online Access:http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9279517/
http://www.ncbi.nlm.nih.gov/pubmed/35831516
https://doi.org/10.1007/s13659-022-00348-x
id ftpubmed:oai:pubmedcentral.nih.gov:9279517
record_format openpolar
spelling ftpubmed:oai:pubmedcentral.nih.gov:9279517 2023-05-15T13:50:20+02:00 Cyclic heptapeptides with metal binding properties isolated from the fungus Cadophora malorum from Antarctic soil Donalle, Guidmar C. Martorell, María Martha Siless, Gastón E. Ruberto, Lucas Cabrera, Gabriela M. 2022-07-14 http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9279517/ http://www.ncbi.nlm.nih.gov/pubmed/35831516 https://doi.org/10.1007/s13659-022-00348-x en eng Springer Nature Singapore http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9279517/ http://www.ncbi.nlm.nih.gov/pubmed/35831516 http://dx.doi.org/10.1007/s13659-022-00348-x © The Author(s) 2022 https://creativecommons.org/licenses/by/4.0/Open AccessThis article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) . CC-BY Nat Prod Bioprospect Original Article Text 2022 ftpubmed https://doi.org/10.1007/s13659-022-00348-x 2022-07-31T01:26:11Z The Antarctic fungus Cadophora malorum produces previously undescribed cyclic heptapeptides (cadophorin A and B) containing an anthranilic acid residue. The planar structure of these peptides was determined by high-resolution mass spectrometry combined with extensive 1D and 2D NMR spectroscopy. The absolute configuration of the amino acids was determined by Marfey’s method, with HPLC analysis of FDVA (Nα-(2,4-dinitro-5-fluorphenyl)-l-valinamide) derivatives making use of a PFP column. Remarkably, cadophorin 2 possesses both the uncommon d-Ile and d-allo-Ile in its structure. The peptides have metal binding properties as shown by LCMS with post column addition of metal salt solutions. These results were supported by DFT calculations. GRAPHICAL ABSTRACT: [Image: see text] SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s13659-022-00348-x. Text Antarc* Antarctic PubMed Central (PMC) Allo ENVELOPE(-61.800,-61.800,-63.967,-63.967) Antarctic The Antarctic Natural Products and Bioprospecting 12 1
institution Open Polar
collection PubMed Central (PMC)
op_collection_id ftpubmed
language English
topic Original Article
spellingShingle Original Article
Donalle, Guidmar C.
Martorell, María Martha
Siless, Gastón E.
Ruberto, Lucas
Cabrera, Gabriela M.
Cyclic heptapeptides with metal binding properties isolated from the fungus Cadophora malorum from Antarctic soil
topic_facet Original Article
description The Antarctic fungus Cadophora malorum produces previously undescribed cyclic heptapeptides (cadophorin A and B) containing an anthranilic acid residue. The planar structure of these peptides was determined by high-resolution mass spectrometry combined with extensive 1D and 2D NMR spectroscopy. The absolute configuration of the amino acids was determined by Marfey’s method, with HPLC analysis of FDVA (Nα-(2,4-dinitro-5-fluorphenyl)-l-valinamide) derivatives making use of a PFP column. Remarkably, cadophorin 2 possesses both the uncommon d-Ile and d-allo-Ile in its structure. The peptides have metal binding properties as shown by LCMS with post column addition of metal salt solutions. These results were supported by DFT calculations. GRAPHICAL ABSTRACT: [Image: see text] SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s13659-022-00348-x.
format Text
author Donalle, Guidmar C.
Martorell, María Martha
Siless, Gastón E.
Ruberto, Lucas
Cabrera, Gabriela M.
author_facet Donalle, Guidmar C.
Martorell, María Martha
Siless, Gastón E.
Ruberto, Lucas
Cabrera, Gabriela M.
author_sort Donalle, Guidmar C.
title Cyclic heptapeptides with metal binding properties isolated from the fungus Cadophora malorum from Antarctic soil
title_short Cyclic heptapeptides with metal binding properties isolated from the fungus Cadophora malorum from Antarctic soil
title_full Cyclic heptapeptides with metal binding properties isolated from the fungus Cadophora malorum from Antarctic soil
title_fullStr Cyclic heptapeptides with metal binding properties isolated from the fungus Cadophora malorum from Antarctic soil
title_full_unstemmed Cyclic heptapeptides with metal binding properties isolated from the fungus Cadophora malorum from Antarctic soil
title_sort cyclic heptapeptides with metal binding properties isolated from the fungus cadophora malorum from antarctic soil
publisher Springer Nature Singapore
publishDate 2022
url http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9279517/
http://www.ncbi.nlm.nih.gov/pubmed/35831516
https://doi.org/10.1007/s13659-022-00348-x
long_lat ENVELOPE(-61.800,-61.800,-63.967,-63.967)
geographic Allo
Antarctic
The Antarctic
geographic_facet Allo
Antarctic
The Antarctic
genre Antarc*
Antarctic
genre_facet Antarc*
Antarctic
op_source Nat Prod Bioprospect
op_relation http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9279517/
http://www.ncbi.nlm.nih.gov/pubmed/35831516
http://dx.doi.org/10.1007/s13659-022-00348-x
op_rights © The Author(s) 2022
https://creativecommons.org/licenses/by/4.0/Open AccessThis article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
op_rightsnorm CC-BY
op_doi https://doi.org/10.1007/s13659-022-00348-x
container_title Natural Products and Bioprospecting
container_volume 12
container_issue 1
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