Abstract:Resumo: Dois novos diterpenos do tipo labdano denominados 16-hidroxilarixol (1) e 16-hidroxi-7-labden-6-ona (2) foram isolados de Conchocarpus cyrtanthus, juntamente com mais três cumarinas: seselina (3), xantoxiletina (4), luvangetina (5); o alcaloide dictamina (6); seis esteroides: -sitosterol (7), estigmasterol (8), campesterol (9), 7-hidroxi--sitosterol (10), 7-hidroxiestigmasterol (11) e 7-hidroxicampesterol (12); três diterpenos: manool (13), 16-hidroximanoiloxido (14) e 16-hidroxi-13-epi-manoiloxi… Show more
“…In contrast with the frequency and availability of β-sitosterol in different species, the other isolated steroid (9) has not yet been reported from any of the Euphorbia species. Although this oxidized sterol has been isolated from other plant species [52], not many researchers have focused on its bioactive and pharmacological effects up until now.…”
The attraction to the Euphorbia genus, with its remarkable diversity in species, is due to its variety of chemical compositions. Euphorbia turcomanica is one of the species of the spurge family growing wildly in Iran. This research aims to investigate the presence of secondary metabolites, specially terpenoid compounds, in terms of structural determination. Samples of E. tucomanica were finely powdered and macerated with acetone/dichloromethane 2:1. Repeated column chromatography using silica gel, MPLC, and HPLC methods followed by the analysis of data obtained from spectroscopic means was carried out to purify and identify the terpenoid constituents. The chemical structures of nine known terpenoids were determined for the first time from E. turcomanica during this study. Loliolide (1), a monoterpene, and eight steroids and triterpenes, including simiarenol (2), isomultiflorenol (3), cycloart-25-ene-3β,24-diol (4), β-sitosterol (5), cycloart-23-ene-3β,25-diol (6), 3α, 11α-dihydroxyurs-12-ene (7), 3β, 24β, 25-trihydroxycycloartane (8), and 7α-hydroxystigmasterol (9) were isolated and identified. E. tucomanica, with a rich terpenoid profile, can be one of the valuable and economic sources providing compounds for drug development.
“…In contrast with the frequency and availability of β-sitosterol in different species, the other isolated steroid (9) has not yet been reported from any of the Euphorbia species. Although this oxidized sterol has been isolated from other plant species [52], not many researchers have focused on its bioactive and pharmacological effects up until now.…”
The attraction to the Euphorbia genus, with its remarkable diversity in species, is due to its variety of chemical compositions. Euphorbia turcomanica is one of the species of the spurge family growing wildly in Iran. This research aims to investigate the presence of secondary metabolites, specially terpenoid compounds, in terms of structural determination. Samples of E. tucomanica were finely powdered and macerated with acetone/dichloromethane 2:1. Repeated column chromatography using silica gel, MPLC, and HPLC methods followed by the analysis of data obtained from spectroscopic means was carried out to purify and identify the terpenoid constituents. The chemical structures of nine known terpenoids were determined for the first time from E. turcomanica during this study. Loliolide (1), a monoterpene, and eight steroids and triterpenes, including simiarenol (2), isomultiflorenol (3), cycloart-25-ene-3β,24-diol (4), β-sitosterol (5), cycloart-23-ene-3β,25-diol (6), 3α, 11α-dihydroxyurs-12-ene (7), 3β, 24β, 25-trihydroxycycloartane (8), and 7α-hydroxystigmasterol (9) were isolated and identified. E. tucomanica, with a rich terpenoid profile, can be one of the valuable and economic sources providing compounds for drug development.
“…Exemplos notáveis dessa classe de produtos naturais envolvendo estudos de atividade citotóxica/antiproliferativa, ilustrados na Figura 1, incluem as coranarinas do tipo C (1) e D (2) (SURESH et al, 2010) e mais amplamente o andrografolídeo (3) e seus derivados (SHARMA et al, 2017). No contexto internacional, a flora brasileira tem sido uma fonte notável de diversos diterpenos dessa natureza como Renealmia exaltata ("pacová-catinga") (SEKIGUCHI et al, 2001), Hedychium coronarium (ENDRINGER et al, 2014), Stemodia foliosa ("meladinha") (SILVA et al, 2008), Dodonaea viscosa ("vassoura vermelha") (OLIVEIRA et al, 2012), Conchocarpus cyrtanthus ("orelha de cabra") (OLIVEIRA et al, 2016) e Leptohyptis macrostachys ("alfavaca-brava") (CAVALCANTI et al, 2021) para circunscrever apenas alguns poucos exemplos. A ampla disponibilidade biológica de espécies vegetais com registros de diterpenos labdanos aliada à grande biodiversidade ainda não explorada em diversos biomas do Brasil, pode oferecer uma oportunidade inovativa importante no desenvolvimento de agentes anticâncer usando essas substâncias como arcabouços moleculares.…”
Diterpenos labdanos são produtos naturais amplamente descritos na literatura científica com potencial farmacológico de interesse biomédico, como atividade anticâncer. Nesse sentido, este trabalho teve como objetivo examinar a atividade inovativa de diterpenos labdanos como agentes anticâncer. Para isso, realizou-se um levantamento dos pedidos de depósito de patentes nas bases de dados INPI, EPO, WIPO, Derwent Innovations Index e Lens Patents empregando as palavras-chave “labdane and cancer”. Os resultados revelaram 28 documentos considerados elegíveis, distribuídos entre distintas plataformas patentárias internacionais com os registros majoritariamente realizados pela China (36%), considerando o período de 1984 a 2021. Essas patentes, segundo a CIP, estão concentradas na categoria A61 (65,06%) e C07 (34,26%). Assim, pode-se inferir que existe pouca atividade inovativa para o uso de labdanos como agentes anticâncer globalmente, nenhuma atividade registrada no Brasil e uma classificação patentária majoritária para aplicações biológicas e químicas, o que sugere uma janela de oportunidade nesse campo de inovação.
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