Covalent Modification of Human Serum Albumin by the Natural Sesquiterpene Lactone Parthenolide

The reactivity of parthenolide (PRT), a natural sesquiterpene lactone from Tanacetum parthenium (Asteraceae), with human serum albumin (HSA) was studied by UHPLC/+ESI-QqTOF MS analysis after tryptic digestion of albumin samples after incubation with this compound. It was found that the single free c...

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Autores principales: Plöger, Michael, Sendker, Jandirk, Langer, Klaus, Schmidt, Thomas J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272280/
https://www.ncbi.nlm.nih.gov/pubmed/25859779
http://dx.doi.org/10.3390/molecules20046211
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author Plöger, Michael
Sendker, Jandirk
Langer, Klaus
Schmidt, Thomas J.
author_facet Plöger, Michael
Sendker, Jandirk
Langer, Klaus
Schmidt, Thomas J.
author_sort Plöger, Michael
collection PubMed
description The reactivity of parthenolide (PRT), a natural sesquiterpene lactone from Tanacetum parthenium (Asteraceae), with human serum albumin (HSA) was studied by UHPLC/+ESI-QqTOF MS analysis after tryptic digestion of albumin samples after incubation with this compound. It was found that the single free cysteine residue, C34, of HSA (0.6 mM) reacted readily with PRT when incubated at approximately 13-fold excess of PRT (8 mM). Time-course studies with PRT and its 11β,13-dihydro derivative at equimolar ratios of the reactants revealed that PRT under the chosen conditions reacts preferably with C34 and does so exclusively via its α-methylene-γ-lactone moiety, while the epoxide structure is not involved in the reaction.
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spelling pubmed-62722802018-12-03 Covalent Modification of Human Serum Albumin by the Natural Sesquiterpene Lactone Parthenolide Plöger, Michael Sendker, Jandirk Langer, Klaus Schmidt, Thomas J. Molecules Article The reactivity of parthenolide (PRT), a natural sesquiterpene lactone from Tanacetum parthenium (Asteraceae), with human serum albumin (HSA) was studied by UHPLC/+ESI-QqTOF MS analysis after tryptic digestion of albumin samples after incubation with this compound. It was found that the single free cysteine residue, C34, of HSA (0.6 mM) reacted readily with PRT when incubated at approximately 13-fold excess of PRT (8 mM). Time-course studies with PRT and its 11β,13-dihydro derivative at equimolar ratios of the reactants revealed that PRT under the chosen conditions reacts preferably with C34 and does so exclusively via its α-methylene-γ-lactone moiety, while the epoxide structure is not involved in the reaction. MDPI 2015-04-09 /pmc/articles/PMC6272280/ /pubmed/25859779 http://dx.doi.org/10.3390/molecules20046211 Text en © 2015 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Plöger, Michael
Sendker, Jandirk
Langer, Klaus
Schmidt, Thomas J.
Covalent Modification of Human Serum Albumin by the Natural Sesquiterpene Lactone Parthenolide
title Covalent Modification of Human Serum Albumin by the Natural Sesquiterpene Lactone Parthenolide
title_full Covalent Modification of Human Serum Albumin by the Natural Sesquiterpene Lactone Parthenolide
title_fullStr Covalent Modification of Human Serum Albumin by the Natural Sesquiterpene Lactone Parthenolide
title_full_unstemmed Covalent Modification of Human Serum Albumin by the Natural Sesquiterpene Lactone Parthenolide
title_short Covalent Modification of Human Serum Albumin by the Natural Sesquiterpene Lactone Parthenolide
title_sort covalent modification of human serum albumin by the natural sesquiterpene lactone parthenolide
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272280/
https://www.ncbi.nlm.nih.gov/pubmed/25859779
http://dx.doi.org/10.3390/molecules20046211
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AT langerklaus covalentmodificationofhumanserumalbuminbythenaturalsesquiterpenelactoneparthenolide
AT schmidtthomasj covalentmodificationofhumanserumalbuminbythenaturalsesquiterpenelactoneparthenolide

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