Isolation and Bioactivities of the Flavonoids Morin and Morin-3-O-β-D-glucopyranoside from Acridocarpus orientalis—A Wild Arabian Medicinal Plant

Abstract

Abstract:Acridocarpus orientalis is an important medicinal plant for some of the locals of Arabian region. Very little is known about its phytochemical constituents. In the present study, we aimed to isolate bioactive chemicals from the crude methanolic extract of the aerial parts of A. orientalis. The extraction and isolation resulted in the purification of two flavonoids: morin (1) and morin-3-O-β-D-glucopyranoside (2). The structure elucidation was carried out by extensive analysis of spectroscopic data and comparison with the reported data for the known constituents. The pure isolates were subjected to various biological assays for their bioactivities. The compounds 1 and 2 were significantly active against the growth of various pathogenic fungi and phytotoxic against lettuce seed at higher concentrations. Furthermore, the free radical scavenging activities, anti-lipid peroxidation, OPEN ACCESSMolecules 2014, 19 17764 and cytotoxic effects against HepG2, HT29, and HCT116 cancer cell lines were also assayed and the results are presented in this paper.

Benzylated and prenylated flavonoids from the root barks of Cudrania tricuspidata with pancreatic lipase inhibitory activity

“…Compounds isolated from C. tricuspidata roots can be divided into chromones (1-2), isoflavonoids (3)(4)(5)(6), flavonols (7)(8), flavanonols (9-10) and flavanones (11)(12)(13)(14)(15)(16)(17). Overall, flavanones showed stronger pancreatic lipase inhibition than other groups in our assay system (Table 1).…”

“…Overall, flavanones showed stronger pancreatic lipase inhibition than other groups in our assay system (Table 1). Related to structure activity relationship, addition of prenyl groups to flavanones (13)(14)(15)(16)(17) increased the inhibitory activity, which is also observed in isoflavonoid (6). Addition of p-hydroxylbenzyl moiety (17) also increased inhibitory activity, as compared to compound 11.…”

“…1) by the analysis of their spectroscopic data and comparison with literature values. [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26] Compound 17 was obtained as light brown syrup and gave HREIMS at 445.1666 (calcd 445.1651), consistent with a molecular formula of C 27 H 25 O 6 . 27 The IR spectrum showed the presence of hydroxyl (3289 cm À1 ) and carbonyl (1647 cm À1 ) groups.…”

“…As a result, the CH 2 Cl 2 and EtOAc-soluble fraction of C. tricuspidata significantly inhibited pancreatic lipase activity in our assay system. Further chromatographic separation of these fractions afforded seventeen compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17). 10 Compounds 1-16 were identified as 5,7-dihydroxychromone (1), 5-hydroxy-2,2-dimethyl-2H,6H-benzodipyran-6-one (2), genistein (3), biochanin A (4), 3 0 -O-methylorobol (5), wighteone (6), kaempferol (7), morin (8), aromadendrine (9), (2R,3R)-2,3-dihydro-3,5,6,7-tetrahydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (10), naringenin (11), 5,7,3 0 ,5 0 -tetrahydroxyflavanone (12), 8-prenylnaringenin (13), cudraflavanone D (14), cudraflavanone A (15), and 2 0 ,5,7-trihydroxy-4,5 0 -(2,2-dimethylchromeno)-8-(3-hydroxy-3-methylbuthyl)flavanone (16), (Fig.…”

Microbial Glycosylation of Flavonoids

“…6). It was proved that kaempferol 3-O-β-D-glucopyranoside has antibacterial properties (Mary and Merina, 2014), whereas morin 3-O-β-D-gluco pyranoside has antifungal and anticancer activity (Hussain et al, 2014). Strain C. echinulata AS 3.3400 is also capable to perform glucosylation of kurarinone to kurarinone 7-O-β-D-glucopyranoside (Fig.…”