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Piper tectoniifolium Kunth: A New Natural Source of the Bioactive Neolignan (−)-Grandisin

The Piper species are a recognized botanical source of a broad structural diversity of lignans and its derivatives. For the first time, Piper tectoniifolium Kunth is presented as a promising natural source of the bioactive (−)-grandisin. Phytochemical analyses of extracts from its leaves, branches a...

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Autores principales: Marques, André M., da Rocha Queiroz, Alexandre Siqueira, Guimarães, Elsie F., Mafud, Ana Carolina, de Sousa Carvalho, Paulo, Mascarenhas, Yvonne Primerano, da Silva Barenco, Thais, Souza, Pâmella Dourila N., Provance, David William, do Nascimento, José Hamilton M., Ponte, Cristiano G., Kaplan, Maria Auxiliadora C., de Lima Moreira, Davyson, Figueiredo, Maria Raquel
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8876808/
https://www.ncbi.nlm.nih.gov/pubmed/35208941
http://dx.doi.org/10.3390/molecules27041151
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author Marques, André M.
da Rocha Queiroz, Alexandre Siqueira
Guimarães, Elsie F.
Mafud, Ana Carolina
de Sousa Carvalho, Paulo
Mascarenhas, Yvonne Primerano
da Silva Barenco, Thais
Souza, Pâmella Dourila N.
Provance, David William
do Nascimento, José Hamilton M.
Ponte, Cristiano G.
Kaplan, Maria Auxiliadora C.
de Lima Moreira, Davyson
Figueiredo, Maria Raquel
author_facet Marques, André M.
da Rocha Queiroz, Alexandre Siqueira
Guimarães, Elsie F.
Mafud, Ana Carolina
de Sousa Carvalho, Paulo
Mascarenhas, Yvonne Primerano
da Silva Barenco, Thais
Souza, Pâmella Dourila N.
Provance, David William
do Nascimento, José Hamilton M.
Ponte, Cristiano G.
Kaplan, Maria Auxiliadora C.
de Lima Moreira, Davyson
Figueiredo, Maria Raquel
author_sort Marques, André M.
collection PubMed
description The Piper species are a recognized botanical source of a broad structural diversity of lignans and its derivatives. For the first time, Piper tectoniifolium Kunth is presented as a promising natural source of the bioactive (−)-grandisin. Phytochemical analyses of extracts from its leaves, branches and inflorescences showed the presence of the target compound in large amounts, with leaf extracts found to contain up to 52.78% in its composition. A new HPLC-DAD-UV method was developed and validated to be selective for the identification of (−)-grandisin being sensitive, linear, precise, exact, robust and with a recovery above 90%. The absolute configuration of the molecule was determined by X-ray diffraction. Despite the identification of several enantiomers in plant extracts, the major isolated substance was characterized to be the (−)-grandisin enantiomer. In vascular reactivity tests, it was shown that the grandisin purified from botanical extracts presented an endothelium-dependent vasorelaxant effect with an IC(50) of 9.8 ± 1.22 μM and around 80% relaxation at 30 μM. These results suggest that P. tectoniifolium has the potential to serve as a renewable source of grandisin on a large scale and the potential to serve as template for development of new drugs for vascular diseases with emphasis on disorders related to endothelial disfunction.
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spelling pubmed-88768082022-02-26 Piper tectoniifolium Kunth: A New Natural Source of the Bioactive Neolignan (−)-Grandisin Marques, André M. da Rocha Queiroz, Alexandre Siqueira Guimarães, Elsie F. Mafud, Ana Carolina de Sousa Carvalho, Paulo Mascarenhas, Yvonne Primerano da Silva Barenco, Thais Souza, Pâmella Dourila N. Provance, David William do Nascimento, José Hamilton M. Ponte, Cristiano G. Kaplan, Maria Auxiliadora C. de Lima Moreira, Davyson Figueiredo, Maria Raquel Molecules Article The Piper species are a recognized botanical source of a broad structural diversity of lignans and its derivatives. For the first time, Piper tectoniifolium Kunth is presented as a promising natural source of the bioactive (−)-grandisin. Phytochemical analyses of extracts from its leaves, branches and inflorescences showed the presence of the target compound in large amounts, with leaf extracts found to contain up to 52.78% in its composition. A new HPLC-DAD-UV method was developed and validated to be selective for the identification of (−)-grandisin being sensitive, linear, precise, exact, robust and with a recovery above 90%. The absolute configuration of the molecule was determined by X-ray diffraction. Despite the identification of several enantiomers in plant extracts, the major isolated substance was characterized to be the (−)-grandisin enantiomer. In vascular reactivity tests, it was shown that the grandisin purified from botanical extracts presented an endothelium-dependent vasorelaxant effect with an IC(50) of 9.8 ± 1.22 μM and around 80% relaxation at 30 μM. These results suggest that P. tectoniifolium has the potential to serve as a renewable source of grandisin on a large scale and the potential to serve as template for development of new drugs for vascular diseases with emphasis on disorders related to endothelial disfunction. MDPI 2022-02-09 /pmc/articles/PMC8876808/ /pubmed/35208941 http://dx.doi.org/10.3390/molecules27041151 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Marques, André M.
da Rocha Queiroz, Alexandre Siqueira
Guimarães, Elsie F.
Mafud, Ana Carolina
de Sousa Carvalho, Paulo
Mascarenhas, Yvonne Primerano
da Silva Barenco, Thais
Souza, Pâmella Dourila N.
Provance, David William
do Nascimento, José Hamilton M.
Ponte, Cristiano G.
Kaplan, Maria Auxiliadora C.
de Lima Moreira, Davyson
Figueiredo, Maria Raquel
Piper tectoniifolium Kunth: A New Natural Source of the Bioactive Neolignan (−)-Grandisin
title Piper tectoniifolium Kunth: A New Natural Source of the Bioactive Neolignan (−)-Grandisin
title_full Piper tectoniifolium Kunth: A New Natural Source of the Bioactive Neolignan (−)-Grandisin
title_fullStr Piper tectoniifolium Kunth: A New Natural Source of the Bioactive Neolignan (−)-Grandisin
title_full_unstemmed Piper tectoniifolium Kunth: A New Natural Source of the Bioactive Neolignan (−)-Grandisin
title_short Piper tectoniifolium Kunth: A New Natural Source of the Bioactive Neolignan (−)-Grandisin
title_sort piper tectoniifolium kunth: a new natural source of the bioactive neolignan (−)-grandisin
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8876808/
https://www.ncbi.nlm.nih.gov/pubmed/35208941
http://dx.doi.org/10.3390/molecules27041151
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