Determination of Flavonoids in Selected Scleranthus Species and Their Anti-Collagenase and Antioxidant Potential

Abstract

A new 5,7-dihydroxy-3′-methoxy-4′-acetoxyflavone-8-C-β-D-arabinopyranoside-2″-O-(4″′-acetoxy)-glucoside (6) and three known flavone C-glycosides—5,7,3′,4′-tetrahydroxyflavone-6-C-xyloside-8-C-β-D-glucoside (lucenin-1) (7), 5,7,3′-trihydroxyflavone-6-C-glucoside-8-C-β-D-glucoside (vicenin-2) (8), and 5,7,4′-trihydroxy-3′-methoxyflavone-6-C-β-D-glucopyranoside-8-C-α-arabinopyranoside (chrysoeriol-6-C-β-D-glucopyranoside-8-C-α-arabinopyranoside) (9)—were isolated from aerial parts of Scleranthus perennis L. (Caryophyllaceae). Their structures were determined through the use of comprehensive spectroscopic and spectrometric methods, and a method for the quantification of the major constituents of S. perennis and S. annuus L. was developed. Furthermore, the anti-collagenase and antioxidant activities of all isolated compounds obtained from extracts and fractions from both Scleranthus species were evaluated. The highest percentage of collagenase inhibition (at 400 µg/mL) was distinguished for methanolic extracts (22.06%, 32.04%) and ethyl acetate fractions (16.59%, 14.40%) from S. annuus and S. perennis. Compounds 6–9 displayed moderate inhibitory activity, with IC50 values ranging from 39.59–73.86 µM.

UHPLC-MS Phytochemical Profiling and Insight into Bioactivity of Rabelera holostea (Greater Stitchwort) Extract

“…Confirmation of some compounds was approved using available standards (see the header of Table 2 ), and the other compounds were identified according to HRMS and MS n data with the consultation of previously published spectroscopic data on the analysis of secondary metabolites in Stellaria species [ 1 , 8 , 19 , 35 , 36 ] and generally in the family Caryophyllaceae [ 12 , 13 , 37 , 38 , 39 ].…”

Using Flavonoid Substitution Status to Predict Anticancer Effects in Human Melanoma Cancers: An In Vitro Study

“…Compounds 1 (CAS number: 520-36-5), 2 (CAS number: 3681-93-4), 14 (CAS number: 480-40-0), 18 (CAS number: 520-18-3), 24 (CAS number: 6151-25-3), 25 (CAS number: 90-19-7), 26 (CAS number: 480-19-3), 30 (CAS number: 529-44-2), 33 (CAS number: 69097-99-0), and 37 (CAS number: 446-72-0) were purchased from Carl Roth (Karlsruhe, Germany); 15 (CAS number: 6665-66-3) was obtained from ThermoFisher Scientific (Waltham, MA, USA); 8 (CAS number: 29741-10-4), 16 (CAS number: 38183-03-8), 23 (CAS number: 489-32-7), 35 (CAS number: 13241-33-3), and 36 (CAS number: 552-66-9) were obtained from Cayman Chemical (Ann Arbor, MI, USA); and 4 was obtained from AmBeed (Arlington, IL, USA). Flavonoids 3 [13], 6 [14], 7, 9 [15], 10-12 [16], 13 [17], 19 [18], 20, 28 [19], 22, and 29 [20] were isolated and identified in the Department of Pharmacognosy at the Medical University of Białystok (Poland). Compounds 5 (CAS number: 77298-67-0), 17 (CAS number: 14813-19-5), and 31 (CAS number: 520-32-1) were obtained from Biosynth Carbosynth (London, UK); 21 (CAS number: 22688-78-4) and 27 (CAS number: 22688-79-5) were purchased from Extrasynthese (Genay, France); and 32 (CAS number: 490-31-3) and 34 (CAS number: 520-26-3) were obtained from Fluka Analysis (St. Louis, MO, USA).…”

“…After 48 h of exposure, in both A375 and C32 cells, the IC 50 of 17 (14.7 ± 1.2 and 14.7 ± 1.1 µM, respectively) showed comparable cytotoxicity to cPt (14.4 ± 1.1 and 15.0 ± 1.2 µM). Importantly, 5,6-dihydroxyflavone (15), 7,8-dihydroxyflavone (16), and zapotin (17) were more active in cancer cells than in fibroblasts.…”

“…Extensive biological in vitro studies led to identifying which flavonoid substitution patterns play a crucial role in their anticancer activity, which allowed for the demonstration of the structureactivity relationships (SARs). Thus, in this study, we investigated the anti-cancer potential of 37 flavonoids to identify active compounds: apigenin (1), apigenin 8-C-glucoside (vitexin) (2), apigenin 7-O-glucoside (3), apigenin 7-O-glucuronide (4), apigenin 7-Orutinoside (5), luteolin (6), luteolin 7-O-glucoside (cynaroside) (7), luteolin 7-O-glucuronide (8), luteolin 7-O-sambubioside (9), 5,7,3 ′ -trihydroxy-4 ′ -acetoxy-flavone-8-C-xyloside-2 ′′ -O-glucoside (scleranthoside A) (10), 5,7,3 ′ -trihydroxy-4 ′ -methoxyflavone-8-C-xyloside-2 ′′ -O-glucoside (scleranthoside B) (11), 5,7-dihydroxy-3 ′ -methoxy-4 ′ -acetoxyflavone-8-Cxyloside-2 ′′ -O-(4 ′′′ -acetoxy)-glucoside (scleranthoside C) (12), 5,7-dihydroxy-3 ′ -methoxy-4 ′ -acetoxyflavone-8-C-arabinoside-2 ′′ -O-(4 ′′′ -acetoxy)-glucoside (scleranthoside D) (13), chrysin (14), 5,6-dihydroxyflavone (15), 7,8-dihydroxyflavone (16), zapotin (17), kaempferol (18), 8-methoxykaempferol (19), kaempferol 3-O-glucoside (astragalin) (20), kaempferol 3-Oglucuronide (21), kaempferol 3-O-galactoside (hyperoside) (22), icariin (23), quercetin (24), 7-methoxyquercetin (rhamnetin) (25), 3 ′ -methoxyquercetin (isorhamnetin) (26), quercetin 3-O-glucuronide (27), quercetin 3-O-rutinoside (rutin) (28), quercetin 3-O-rutinoside-7-O-glucoside (29), myricetin (30), tricin (31), robinetin (32), hesperetin (33), hesperetin 7-O-rutinoside (hesperidin) (34), hesperetin 7-O-neohesperidoside (neohesperidin) (35), daidzein (36), and genistein (37). The chemical and biological properties of flavonoids and their der...…”

Scleranthus perennis extracts prolonged the honeybee lifespan

“…The aerial parts of S. perennis were collected in the Białystok area of Poland. Extraction and fractionation were performed as previously described 2 . The plant material was powdered and extracted using an ultrasonication bath.…”