RESUMO
To identify antibacterial components in traditional Mongolian medicinal plant Caryopteris mongolica, an ortho-quinone abietane caryopteron A (1) and three its derivatives caryopteron B-D (2-4) were isolated from the roots of the plant together with three known abietanes demethylcryptojaponol (5), 6α-hydroxydemethyl cryptojaponol (6), and 14-deoxycoleon U (7). The chemical structures of these abietane derivatives were elucidated on the basis of spectroscopic data. Compounds 1-4 had C-13 methylcyclopropane substructures, and 2-4 had a hexanedioic anhydride ring C instead of ortho-quinone in 1. The stereochemistry of these compound was assumed from NOE spectra and ECD Cotton effects. Compounds 1 and 5-7 showed antibacterial activities against the Gram-positive bacteria Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, and Micrococcus luteus, being 1 the more potent.
Assuntos
Antibacterianos/química , Diterpenos/química , Lamiaceae/química , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Bactérias Gram-Positivas/efeitos dos fármacos , Lamiaceae/metabolismo , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Conformação Molecular , Raízes de Plantas/química , Raízes de Plantas/metabolismo , Plantas Medicinais/química , Plantas Medicinais/metabolismo , Quinonas/químicaRESUMO
A diterpenoid diglucoside (12,19-di-O-ß-D-glucopyranosyl-11-hydroxyabieta-8,11,13-triene-19-one), isoscutellarein 7-O-[ß-D-xylopyranosyl-(1â2)]-ß-D-glucopyranoside, isoscutellarein 7-O-[α-L-rhamnopyranosyl-(1â2)]-ß-D-glucopyranoside, hypolaetin 7-O-[6â³-O-(p-E-coumaroyl)]-ß-D-glucopyranoside, hypolaetin 7-O-[6â³-O-(E-caffeoyl)]-ß-D-glucopyranoside, and 15 known compounds were isolated from aerial parts of the Mongolian medicinal plant Caryopteris mongolica. The cholinesterase-inhibitory activities of the constituents were estimated. The abietane diterpenoids (12-O-demethylcryptojaponol and 6α-hydroxydemethylcryptojaponol) showed potent inhibitory activity against acetylcholinesterase from human erythrocytes and electric eel, and against butyrylcholinesterase from horse serum.
Assuntos
Diterpenos/metabolismo , Lamiaceae/química , Componentes Aéreos da Planta/metabolismo , Plantas Medicinais/química , Lamiaceae/metabolismoRESUMO
Chemical investigation of the acetone extract from the aerial parts of the Mongolian medicinal plant Dracocephalum foetidum resulted in the isolation of three limonene glycosides, a caffeic acid trimer, four rosmarinic acid glucosides, and five acacetin acyl glycosides, together with 13 known natural products. The chemical structures of all of the compounds were determined by spectroscopic analyses. Among these compounds three showed hyaluronidase inhibitory activity. In addition, one other compound showed stronger 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity than the positive control Trolox, whereas three other compounds demonstrated a similar activity to that of Trolox.
Assuntos
Antioxidantes/isolamento & purificação , Flavonas/isolamento & purificação , Glicosídeos/isolamento & purificação , Lamiaceae/química , Monoterpenos/isolamento & purificação , Propanóis/isolamento & purificação , Compostos de Bifenilo/química , Hialuronoglucosaminidase/antagonistas & inibidores , Medicina Tradicional da Mongólia , Mongólia , Picratos/química , Componentes Aéreos da Planta/química , Extratos Vegetais/isolamento & purificação , Plantas MedicinaisRESUMO
Activity-guided isolation of the n-butanol fraction of Chamaerhodos erecta and water soluble fraction of C. altaica resulted in the isolation of 39 compounds, including new compounds identified as 4,5-dihydroxybenzaldehyde-3-O-ß-D-glucopyranoside (1) from C. erecta and quercetin-3-O-ß-D-glucuronopyranosyl-4'-O-ß-D-glucopyranoside (2) from C. altaica. A total of 37 other compounds were identified based on physico-chemical properties and spectroscopic data. Antioxidative activity was evaluated using a DPPH radical-scavenging method, hyaluronidase inhibitory activity, and advanced glycation end products production inhibitory activity of isolated compounds. Some flavonols (4, 6, 9-11, 14, 15), catechins (18, 19), an amino acid (20), a lignan glucoside (23), and tannins (29-39) exhibited potential a free radical scavenging activity while the new compound (1) showed weak activity. A catechin (18) and some of the tannins (32, 33, 35, 36, 38) had moderate hyaluronidase inhibitory activity. Some of flavonoids and tannins prevented advanced glycation end products production, and the IC50 of compounds 3, 9, 14-16, 33, 34, 36, 38, and 39 were determined.
Assuntos
Rosaceae/química , Antioxidantes/química , Antioxidantes/farmacologia , Matriz Extracelular/metabolismo , Flavonoides/química , Flavonoides/farmacologia , Flavonóis/química , Flavonóis/farmacologia , Glucosídeos/química , Glucosídeos/farmacologia , Produtos Finais de Glicação Avançada/metabolismo , Hialuronoglucosaminidase/antagonistas & inibidores , Medicina Tradicional da Mongólia , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Plantas Medicinais/química , Quercetina/química , Quercetina/farmacologiaRESUMO
From an extract of the aerial parts of Dracocephalum ruyschiana, five new flavone tetraglycosides, five new benzyl alcohol glycosides, and 19 known compounds were isolated. The tetraglycosides contain a 7-O-ß-d-glucopyranosyl-(1â2)-ß-d-glucopyranosyl-(1â2)-[α-l-rhamnopyranosyl-(1â6)]-ß-d-glucopyranosyl moiety. The benzyl alcohol glycosides had acyl groups on their glycosyl or aglycone moieties. The compounds were tested for antioxidant activity using DPPH. Although the new compounds were not active, phenylpropanoylquinic acid derivatives were revealed as radical scavengers in D. ruyschiana.
Assuntos
Antioxidantes/isolamento & purificação , Flavonas/isolamento & purificação , Sequestradores de Radicais Livres/isolamento & purificação , Glicosídeos/isolamento & purificação , Lamiaceae/química , Plantas Medicinais/química , Antioxidantes/química , Antioxidantes/farmacologia , Álcool Benzílico , Compostos de Bifenilo/farmacologia , Flavonas/química , Flavonas/farmacologia , Sequestradores de Radicais Livres/química , Sequestradores de Radicais Livres/farmacologia , Glicosídeos/química , Glicosídeos/farmacologia , Estrutura Molecular , Mongólia , Picratos/farmacologiaRESUMO
A methanol extract of Abies sibirica Ladeb, a Mongolian medicinal plant, had an inhibitory effect on both lipase activity in mouse plasma and LDL anti-oxidative activity, which are preventative factors for arteriosclerosis. The extract was fractionated by silica gel column chromatography and its active constituents were sought. From lipid soluble fractions, 20 terpenoids including seven hitherto unknown triterpenes were isolated. The latter triterpenes had either a γ-lactone ring with a lactol or a derivative thereof. Their chemical structures were determined by spectroscopic methods. The lipase inhibitory activity and LDL anti-oxidative activity of these compounds were evaluated. Some constituents (either lipase inhibitory or LDL anti-oxidative activities) had moderate inhibitory activities.