RESUMO
Seven diterpenoid alkaloids : delcosine(1), delsoline(2), gigactonine(3), lycoctonine(4), takaosamine(5), atisine(6) and hetisinone(7) have been isolated from the aerial parts of Consolida regalis subsp. paniculata var. paniculata. The presence of compounds 1,2,5,6 and 7 in this plant has not been previously reported.
RESUMO
INTRODUCTION: The phytochemical and biological studies carried out on Salvia species showed that their extracts and constituents have various biological activities. OBJECTIVE: The aim of this study was the isolation of diterpenoids from the roots of Salvia barrelieri Ettling and the determination of the antioxidant activity. METHODOLOGY: Chromatographic methods were used for fractionation and isolation, respectively. Structure elucidation was established by spectroscopic methods. Five antioxidant assays were performed. RESULTS: Three new abietane diterpenoids barreliol, royleanone 12-methyl ether and 7-epi-salviviridinol, and six known diterpenoids, with a known dammarane triterpenoid, pyxinol were isolated. The absolute stereochemistry of pyxinol was confirmed by X-ray analysis. CONCLUSION: Taxodione exhibited the highest antioxidant activity among the tested compounds.
Assuntos
Antioxidantes/química , Antioxidantes/farmacologia , Diterpenos/química , Diterpenos/farmacologia , Raízes de Plantas/química , Salvia/química , Relação Dose-Resposta a Droga , Peroxidação de Lipídeos/efeitos dos fármacos , Modelos Moleculares , Estrutura Molecular , beta Caroteno/químicaRESUMO
The essential oil from the aerial parts of Stachys cretica L. subsp. smyrnaea Rech. fil. (Lamiaceae), endemic to Turkey, was investigated by using GC and GC-MS. Thirty-four of 37 components, represented 99.7% of the total oil, were identified. The major components of the essential oil were trans-beta-caryophyllene (51.0%), germacrene-D (32.8%), a-humulene (3.1%), delta-cadinene (2.1%) and delta-elemene (2.1%). The antimicrobial activity of the essential oil, trans-beta-caryophyllene and five different extracts of the aerial parts of S. cretica L. subsp. smyrnaea were investigated by the standard disc diffusion method. The essential oil and trans-beta-caryophyllene exhibited antibacterial and antifungal activities. The activity increased with increasing concentrations of the essential oil and the extracts. The essential oil showed antimicrobial activity, particularly against Pseudomonas aeruginosa and Bacillus subtilis. The extracts exhibited either moderate or no activity.
Assuntos
Antibacterianos/química , Antibacterianos/farmacologia , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Óleos de Plantas/química , Óleos de Plantas/farmacologia , Stachys/química , Bactérias/efeitos dos fármacos , Cromatografia Gasosa-Espectrometria de MassasRESUMO
From the roots of Delphinium linearilobum (Trautv.) N. Busch two new norditerpene alkaloids linearilobin and linearilin, and the known alkaloids lycoctonine, 14-acetyltalatizamine, browniine, cammaconine, talatizamine, and cochlearenine were isolated. Spectroscopic techniques were used for structure determination. Antioxidant activity was performed by DPPH and metal chelating activity assays.
Assuntos
Alcaloides/química , Delphinium/química , Diterpenos/química , Alcaloides/isolamento & purificação , Quelantes/química , Quelantes/isolamento & purificação , Diterpenos/isolamento & purificação , Sequestradores de Radicais Livres/química , Sequestradores de Radicais Livres/isolamento & purificação , Ferro/química , Espectroscopia de Ressonância Magnética/métodos , Estrutura Molecular , Raízes de Plantas/química , Plantas Medicinais/químicaRESUMO
The vascular effect of salvigenin (6-hydroxyapigenin 6,7,4' -trimethyl ether), a natural flavone, was investigated in comparison with another flavone, 6-hydroxyluteolin 6,7,3',4' -tetramethyl ether in rat aortic rings. Cumulative addition of their increasing concentrations (10(-9)-10(-4)M) produced graded relaxations on rings precontracted with noradrenaline (10(-6) M) and KCl (40 mM). The maximal relaxations induced by flavones were similar, however, based on their pEC50 values salvigenin displayed a higher potency than 6-hydroxyluteolin 6,7,3',4'-tetramethyl ether. Endothelium removal markedly reduced the relaxations to salvigenin while the responses to 6-hydroxyluteolin 6,7,3',4'-tetramethyl ether were partially affected. In addition, a significant decrease was observed in maximal responsiveness and sensitivity to flavones in the presence of L-NOARG, a NO synthase inhibitor. The cyclooxygenase inhibitor indomethacin significantly inhibited the relaxations to salvigenin, but not altered the responses to 6-hydroxyluteolin 6,7,3',4'-tetramethyl ether. Our results provide evidence that salvigenin is an effective flavone in causing vasorelaxation which appears to be mediated by endothelium derived NO and prostacyclin. Whereas, the other flavone, 6-hydroxyluteolin 6,7,3',4'-tetramethyl ether induced relaxant responses are partially endothelium, presumably NO mediated.
Assuntos
Aorta Torácica/efeitos dos fármacos , Flavonas/farmacologia , Músculo Liso Vascular/efeitos dos fármacos , Acetilcolina/farmacologia , Animais , Endotélio Vascular/fisiologia , Inibidores Enzimáticos/farmacologia , Técnicas In Vitro , Luteolina/farmacologia , Masculino , Relaxamento Muscular/efeitos dos fármacos , Óxido Nítrico Sintase Tipo III/antagonistas & inibidores , Nitroarginina/farmacologia , Nitroprussiato/farmacologia , Norepinefrina/farmacologia , Potássio/farmacologia , Ratos , Ratos Wistar , Vasodilatadores/farmacologiaRESUMO
The three new triterpenes (1-3) and five known triterpenes and a sterol were isolated from the acetone extract of a Turkish collection of Salvia kronenburgii. The structures of the new triterpenes were established as 1beta,2alpha-dihydroxy-3beta-acetoxy-11-oxours-12-ene (1), 2alpha,20beta-dihydroxy-3beta-acetoxyurs-9(11),12-diene (2), and 1beta,2alpha-dihydroxy-3beta-acetoxyurs-9(11),12-diene (3) on the basis of spectral analyses, including 1D and 2D NMR and mass spectroscopy. It is probable that compounds 2 and 3 are artifacts from dehydration of the corresponding allylic alcohols. 1beta,2alpha,3beta,11alpha-Tetrahydroxyurs-12-ene (5), the most abundant compound in the extract, was found to be highly cytotoxic to renal, non-small cell lung, and breast cancer cell lines.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Plantas Medicinais/química , Salvia/química , Triterpenos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Feminino , Humanos , Concentração Inibidora 50 , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Estereoisomerismo , Triterpenos/química , Triterpenos/farmacologia , TurquiaRESUMO
Seven Salvia species were investigated recently for their chemical and biological activities. Some terpenoidal compounds exhibited cardiovascular and antibacterial activities. A number of new diterpenoids were obtained and their structures were established through extensive spectral analysis.
Assuntos
Anti-Infecciosos/farmacologia , Fármacos Cardiovasculares/farmacologia , Salvia/química , Terpenos/farmacologia , Animais , Anti-Infecciosos/química , Pressão Sanguínea/efeitos dos fármacos , Fármacos Cardiovasculares/química , Frequência Cardíaca/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Terpenos/químicaRESUMO
Bioguided-fractionation of an acetone extract of the roots of Salvia cilicica (Lamiaceae) led to isolation of two new diterpenes, 7-hydroxy-12-methoxy-20-nor-abieta-1,5(10),7,9,12-pentaen-6,14-dione and abieta-8,12-dien-11,14-dione (12-deoxy-royleanone), together with oleanolic acid, ursolic acid, ferruginol, inuroyoleanol and cryptanol. Their structures were determined spectroscopically, which included HREIMS and 2D NMR spectroscopic analysis. The new abietane derivatives showed appreciable in vitro antileishmanial activity against intracellular amastigote forms of both Leishmania donovani (IC(50) values of 170 and 120 nM, respectively) and Leishmania major (IC(50) values of 290 and 180 nM, respectively). The triterpenoic acids were found to be potently active against amastigote (IC(50) values of 7-120 nM) and moderately active against promastigote stages (IC(50) values of 51-137 nM) of the two Leishmania species.
Assuntos
Abietanos , Antiprotozoários/farmacologia , Diterpenos/química , Diterpenos/farmacologia , Leishmania donovani/efeitos dos fármacos , Leishmania major/efeitos dos fármacos , Salvia/química , Triterpenos/química , Triterpenos/farmacologia , Animais , Concentração Inibidora 50 , Estrutura Molecular , Raízes de Plantas/químicaRESUMO
From the roots of Salvia eriophora (Lamiaceae), a new compound, 4,14-dihydroxysaprorthoquinone, was isolated in addition to ten known diterpenoids. The structure of the new compound was established by spectroscopic analysis. The crude extract of the plant and the isolated diterpenoids were tested for their cardiovascular activities using Wistar Albino rats. Activity was demonstrated in the crude extract and in 4,14-dihydroxysaprorthoquinone, aethiopinone, ferruginol, 4,12-dihydroxysapriparaquinone, and 6,7-dehydroroyleanone.
Assuntos
Abietanos , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Quinonas/isolamento & purificação , Salvia , Animais , Pressão Sanguínea/efeitos dos fármacos , Diterpenos/química , Frequência Cardíaca/efeitos dos fármacos , Espectroscopia de Ressonância Magnética , Masculino , Estrutura Molecular , Naftoquinonas/química , Naftoquinonas/isolamento & purificação , Naftoquinonas/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Raízes de Plantas/química , Quinonas/química , Ratos , Ratos WistarRESUMO
Salvia ceratophylla L. has yielded four known and two new diterpenoids together with two triterpenic acids, a steroid and a flavone. The structures of the compounds were established by spectroscopic analyses. One of the known compounds candidissiol exhibited a high antibacterial activity against Staphylococcus epidermidis and Proteus mirabilis.