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

Author:

Marques André M.ORCID,da Rocha Queiroz Alexandre Siqueira,Guimarães Elsie F.,Mafud Ana CarolinaORCID,de Sousa Carvalho Paulo,Mascarenhas Yvonne PrimeranoORCID,da Silva Barenco Thais,Souza Pâmella Dourila N.,Provance David William,do Nascimento José Hamilton M.ORCID,Ponte Cristiano G.ORCID,Kaplan Maria Auxiliadora C.,de Lima Moreira DavysonORCID,Figueiredo Maria Raquel

Abstract

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 IC50 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.

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

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