RESUMO
Plectranthus (Lamiaceae), which-according to the latest systematic revision-includes three separate genera (Coleus, Plectranthus sensu stricto, and Equilabium), is a genus widely used in traditional medicine-mainly in the treatment of various ailments of the digestive tract, respiratory tract, and skin. Many species of Plectranthus s.l. have been shown to produce phenolic compounds and terpenes. Diterpenes, especially those of the abietane class, are the most studied group of secondary metabolites found in Plectranthus s.l., which is characterized by a significant structural diversity arising from the oxygenation and further rearrangement of the basic tricyclic abietane skeleton to a complete aromatization of the ring system. This review summarizes the known information on abietane diterpenes, showing their structures, sources, and biosynthesis. A classification of these compounds into nine groups, according to the arrangement of their ring C, is used. Royleanones, spirocoleons, and hydroquinones are the largest classes of abietane diterpenes, covering more than 70% of all the compounds reviewed.
Assuntos
Abietanos/química , Diterpenos/química , Extratos Vegetais/química , Plectranthus/química , Estrutura Molecular , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Relação Estrutura-AtividadeRESUMO
The phytochemical analysis of a methanolic extract from Helichrysum petiolare Hilliard & B. L. (Asteraceae) confirmed the content of phenylpropanoids and flavonoids. Five secondary metabolites were isolated using preparative HPLC, namely coumarin scopolin (1), 3-chlorogenic acid (2), caffeic acid-hexose derivative (3), dicaffeoylquinic acid (5), and the flavonoid isoquercitrin (4). These compounds were identified from this species for the first time. Only dicaffeoylquinic acid was able to inhibit Escherichia coli CCM 7929 at the concertation of 512 μg mL-1 in a screening of antibacterial activity.
Assuntos
Asteraceae , Helichrysum , Antioxidantes/farmacologia , Flavonoides/farmacologia , Helichrysum/química , Compostos Fitoquímicos/química , Extratos Vegetais/análiseRESUMO
Fourteen diterpenes were isolated from methanol extracts of the aerial parts ofColeus comosus,Coleus forsteri "Marginatus", and Plectranthus ciliatus. The compounds belong to the abietane (1-4, 9-11, and 13), ent-clerodane (5-8), and ent-kaurane (14, 15) classes. Three new compounds were isolated from C. comosus, including 3-O-acetylornatin G (2), 3,12-di-O-acetylornatin G (3), ornatin B methyl ester (5), and ornatin F (4), for which we proposed a revised structure. The structures of the compounds were determined by comprehensive spectroscopic data analysis. The isolated diterpenes were examined in silico for their physicochemical and early ADME properties. Their antiproliferative effects were determined in vitro using human breast (MDA-MB-231 and MCF-7), cervical (HeLa), and glioblastoma (U-87 MG) cancer cell lines. The royleanone- and hydroquinone-type abietane diterpenes (9-13)exhibited the most potent antiproliferative activity against all cancer cell lines tested, particularly against glioblastoma cells, with IC50 values ranging from 1.1 to 15.6 µM.