davidigenin and 1-1-diphenyl-2-picrylhydrazyl

Bioassay-guided fractionation of the roots of Anneslea fragrans var. lanceolata led to the isolation of four dihydrochalcone glucosides, davidigenin-2'-O-(6″-O-4″'-hydroxybenzoyl)-β-glucoside (1), davidigenin-2'-O-(2″-O-4″'-hydroxybenzoyl)-β-glucoside (2), davidigenin-2'-O-(3″-O-4″'-hydroxybenzoyl)-β-glucoside (3), and davidigenin-2'-O-(6″-O-syringoyl)-β-glucoside (4), and 13 known compounds. The structures were identified by means of spectroscopic analysis. Davidigenin-2'-O-(6″-O-syringoyl)-β-glucoside (4), 1-O-3,4-dimethoxy-5-hydroxyphenyl-6-O-(3,5-di-O-methylgalloyl)-β-glucopyranoside (5), lyoniresinol (10), and syringic acid (13) showed ABTS [2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid)] cation radical scavenging activity, with SC(50) values of 52.6 ± 5.5, 26.0 ± 0.7, 6.0 ± 0.2, and 27.5 ± 0.6 μg/mL in 20 min, respectively. Lyoniresinol (10), isofraxidin (12), and syringic acid (13) also showed DPPH [1,1-diphenyl-2-picrylhydrazyl] radical scavenging activity, with SC(50) values of 8.4 ± 1.8, 51.6 ± 2.2, and 4.3 ± 0.7 μg/mL in 30 min, respectively.

Topics: Antioxidants; Biphenyl Compounds; Chalcone; Chalcones; Free Radical Scavengers; Glucosides; Molecular Structure; Picrates; Plant Roots; Taiwan; Theaceae

Aeroto-Niu-O16, an oxygen-tolerant bovine rumen bacterium, is capable of aerobically reducing isoflavones daidzein and genistein to dihydrodaidzein and dihydrogenistein through catalytic hydrogenation. In this study, it was found that bacterium strain Aeroto-Niu-O16 was able to cleavage the C-ring of liquiritigenin (LG), which is one of the main biologically active components of licorice roots, in the presence of atmospheric oxygen. LG was prepared by acid hydrolysis of the crude extract of licorice roots. The metabolite of LG obtained in strain Aeroto-Niu-O16 was identified as davidigenin (DG) based on the data of UV, MS, 1H and 13C NMR. The maximal concentration of LG that the strain Aeroto-Niu-O16 was able to transform effectively was 0.8 mmol x L(-1) and the average productivity of the metabolite DG was 71.7%. Furthermore, when 0.1% (m/v) of L-cysteine or sodium thiosulfate was added in the cultural medium, the average bioconversion rate of LG was increased from 71.7% to 78.3% and 77.2%, respectively. The in vitro antioxidant investigation showed that 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activity of DG was significantly or extremely significantly higher than that of LG at the concentrations from 0.2 mmol x L(-1) to 1.6 mmol x L(-1). We discoverd for the first time that LG can be converted to DG, which has stronger and wider biological activities, through microbial biotransformation method.

Topics: Animals; Antioxidants; Bacteria, Anaerobic; Biotransformation; Biphenyl Compounds; Cattle; Chalcone; Cysteine; Flavanones; Glycyrrhiza; Picrates; Plant Roots; Plants, Medicinal; Rumen; Thiosulfates

Mascarenhasia arborescens A. DC. (Apocynaceae) is used in traditional medicine in the North of Madagascar to treat intestinal disorders, intestinal spasms and diarrhoea.. The main objective of this work was to evaluate the antispasmodic activity of the crude methanolic extract of Mascarenhasia arborescens and of its four partitions and to identify the effective compound responsible for this effect.. Isolation and structure elucidation techniques were performed in order to identify the bioactive constituent of Mascarenhasia arborescens and HPLC analysis was used for its quantification. Total phenolic content (TPC) of crude extracts and partitions were determined using the Folin-Ciocalteu method. Crude methanolic extract, partitions and the bioactive compound were investigated for their spasmolytic activity on several isolated organs. Their antiradical activity was also investigated by the DPPH test.. Bioassay-guided fractionation using isolated guinea pig ileum pre-contracted with histamine 3x10(-6) M led to the isolation of davidigenin (DG), a dihydrochalcone, as the main active constituent from the most promising methylene chloride partition (McP). This partition was effective on isolated guinea pig ileum pre-contracted with 3x10(-6) M histamine, with a median effective concentration (EC(50)) of 41.19+/-3.74 microg/ml. The DG content of this partition was shown to be 26.5% by HPLC. DG induced a concentration-dependent relaxation of the histamine pre-contracted guinea pig ileum with an EC(50) of 8.04+/-0.81 microg/ml and a concentration-dependent relaxation of the acetylcholine pre-contracted rat duodenum with an EC(50) of 9.35+/-0.30 microg/ml. It inhibited in a non-competitive manner histamine-induced isolated ileum contraction and the acetylcholine-induced isolated duodenum contraction. Moreover, DG does not have any antiradical activity.. We demonstrated for the first time antispasmodic and antioxidant effects of Mascarenhasia arborescens. This study supports its use in traditional medicine. Furthermore, we highlighted the crucial role of davidigenin in the antispasmodic activity of this plant.

Topics: Animals; Antioxidants; Apocynaceae; Biphenyl Compounds; Chalcone; Chalcones; Chemical Fractionation; Chromatography, High Pressure Liquid; Chromatography, Reverse-Phase; Dose-Response Relationship, Drug; Duodenum; Female; Guinea Pigs; Ileum; In Vitro Techniques; Male; Molecular Structure; Muscle Relaxation; Parasympatholytics; Phenols; Picrates; Plant Extracts; Rats; Rats, Wistar; Spectrometry, Mass, Electrospray Ionization; Spectrophotometry, Ultraviolet