학술논문
Piper tectoniifolium Kunth: A New Natural Source of the Bioactive Neolignan (−)-Grandisin
Document Type
article
Author
André M. Marques; Alexandre Siqueira da Rocha Queiroz; Elsie F. Guimarães; Ana Carolina Mafud; Paulo de Sousa Carvalho; Yvonne Primerano Mascarenhas; Thais da Silva Barenco; Pâmella Dourila N. Souza; David William Provance; José Hamilton M. do Nascimento; Cristiano G. Ponte; Maria Auxiliadora C. Kaplan; Davyson de Lima Moreira; Maria Raquel Figueiredo
Source
Molecules, Vol 27, Iss 4, p 1151 (2022)
Subject
Language
English
ISSN
1420-3049
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.