RESUMEN
The n-butanol extract of Stachys arvensis (L.) L. aerial parts (BESA) was analysed by LC-HRMS/MS. 43 Polyphenols, including flavonoids, cinnamic acid derivatives, phenylethaoids, chromones, gallotannins, coumarins and chalcones with hyperoside (13.85%), panasenoside (10.31%), myricitrin (7.89%) and sayaendoside (7.16%), as the major compounds, were identified. High total phenolics (470.21 ± 1.22 mg GAE/g extract) and total flavonoids (189.05 ± 0.72 mg QE/g extract) contents were measured. In addition, the BESA exhibited a higher antioxidant effect in CUPRAC (A0.5:0.45 ± 0.03 µg/mL), DPPH (IC50:4.51 ± 0.16 µg/mL) and ABTS (IC50:7.10 ± 0.18 µg/mL) assays than the standards BHA and α-Tocopherol. Moreover the extract showed a good inhibitory effect against BChE (IC50: 145.02 ± 0.03 µg/mL) and α-amylase (IC50:2.66 ± 0.0024 mg/mL). The BESA exhibited an excellent anti-inflammatory activity (IC50:416 ± 0,056 µg/mL) which was close to that of acetylsalicylic acid, used as a control. The BESA was toxic towards T. molitor larvae and it possessed a good antibacterial activity against gram (+) and gram (-) tested strains.
RESUMEN
A new triterpene saponin, 2, 3, 21, 23-tetrahydroxyolean-12-en-28-oic-acid-28-O-ß-D- glucosyl-(2''â1')-ß-D-glucoside (1), was isolated from the n-butanol extract of dried aerial parts of Salvia argentea L. (Lamiaceae) in addition to two known flavonoids, apigenin 7-O-ß-D-glucoside (2), threo-guaiacylglycerol 3-O-[6-O-p-hydroxybenzoyl]-ß-D-glucoside (3), luteolin 7-O-ß-D-glucoside (4), verbascoside (5) and rosmarinic acid (6). The structure elucidation of these compounds was based on analyses of spectroscopic data including 1D-, 2D-NMR and HR-ESI-MS techniques and by comparing their NMR data with those reported in the literature. Compound 6 exhibited the highest antioxidant activity in DPPH assay (IC50<3.00 µg/mL) which was better than the standards BHA, BHT, Trolox and ascorbic acid.
RESUMEN
Five undescribed ursane-type triterpenes, identified as 1ß,3ß,15α-trihydroxy-urs-9(11)-12-diene (1), 1ß,3ß,15α,28-tetrahydroxy-urs-9(11),12-diene (2), 1ß,3ß-dihydroxy-urs-9(11),12-dien-28-al (3), 1ß,3ß,7ß,15α,28-pentahydroxy-urs-12-ene (4), and 1ß,3ß,15α-trihydroxy-urs-11-en-28-al (5), together with five known compounds (6-10), were isolated from the acetone extract of the dried aerial parts of Salvia argentea L. var. aurasiaca (Pomel) Batt. et Trab. (Lamiaceae). Structures were elucidated on the basis of extensive spectroscopic analysis including HR-ESI-MS, 1D- and 2D-NMR techniques and comparison with literature data. The antibacterial evaluation of compounds 1-10 of the acetone extract of the dried aerial parts, in addition to nine compounds (11-19) previously isolated from the extract of the fresh aerial parts, by bioautography on Staphylococcus aureus followed by the determination of MIC values of active compounds by serial dilution technique against five bacteria, revealed that two compounds have an antibacterial effect comparable to antibiotics. The cytotoxic activity evaluation of compounds 1-19 showed that Six compounds exhibited an antiproliferative activity against K562 and HT1080 cells with IC50 values ranging from 30.25 to 70.32⯵M.
Asunto(s)
Antibacterianos/farmacología , Antineoplásicos/farmacología , Salvia/química , Triterpenos/farmacología , Argelia , Antibacterianos/aislamiento & purificación , Antineoplásicos/aislamiento & purificación , Bacterias/efectos de los fármacos , Humanos , Células K562 , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Componentes Aéreos de las Plantas/química , Triterpenos/aislamiento & purificaciónRESUMEN
Ten triterpenoids were isolated from the exudate of Salvia argentea L. var. aurasiaca (Pomel) Batt. & Trab. Their structures were elucidated by 1D and 2D NMR and HRESIMS analyses as 11α-methoxyurs-12-ene-1ß,3ß,15α-triol (1), urs-12-ene-1ß,3ß,11α,15α-tetraol (2), 11α-methoxyurs-12-ene-1ß,3ß-diol (3), 1ß,3ß,15α-trihydroxy-11α-methoxyurs-12-en-28-al (4), 1ß,3ß,15α-trihydroxyurs-12-en-28-al (5), urs-12-ene-1ß,3ß,15α,28-tetraol (6), 11α-methoxyurs-12-ene-1ß,3ß,28-triol (7), 13ß,28-epoxyurs-12-ene-1ß,3ß-diol (8), urs-12-ene-3ß,7ß,15α,28-tetraol (9) and olean-12-ene-3ß,7ß,15α,28-tetraol (10). A chemotaxonomic survey of the triterpenoids of Salvia species show that triterpenoids from the exudate of S. argentea var. aurasiaca (Pomel) Batt. & Trab., provide some features, such as hydroxylation at C-15, and hydroxylation at C-7. On this basis, S. argentea L. var. aurasiaca (Pomel) Batt. & Trab., is quite different from S. argentea L.
Asunto(s)
Salvia/química , Triterpenos/aislamiento & purificación , Conformación Molecular , Estereoisomerismo , Triterpenos/químicaRESUMEN
Five known flavonoids (1-5) and three sesquiterpene lactones (6-8) are reported for the first time from the endemic species Centaurea sulphurea Willd. (Asteraceae). Compound 7 is a new heliangolide (6R, 7R, 8S, 3'R)-8alpha-(3',4'-dihydroxy-methylene-2'-butanoyloxy)-15-oxo-helianga-1 (10), 4(5), 11(13)-trien-6,12-olide, named as sulphurein.