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1.
Org Biomol Chem ; 20(5): 1013-1018, 2022 02 02.
Article in English | MEDLINE | ID: mdl-35043137

ABSTRACT

A chemical reductant or a sacrificial electron donor is required in any reduction reactions, generally resulting in undesired chemical waste. Herein, we report a reductant-free reductive [3 + 2 + 1] annulation of ß-keto amides with CS2 enabled by the synergy of electro/copper/base using water as an innocuous anodic sacrifice with O2 as a sustainable by-product. This electrochemical protocol is mild and provides access to polyfunctionalized pyridin-2-ones from simple starting materials in a single step.

2.
Molecules ; 25(17)2020 Sep 02.
Article in English | MEDLINE | ID: mdl-32887336

ABSTRACT

Previously we conducted a phytochemical study on the seeds of Fraxinus excelsior and isolated nine secoiridoid compounds with adipocyte differentiation inhibitory activity and peroxisome proliferator activated receptor alpha (PPARα) activation effects. However, the bioactive constituents and functions of Fraxinus mandshurica seeds have not been studied. In the present study, we investigated the secoiridoid compounds in F. mandshurica seed extract (FM) using column chromatography, 1H-NMR, 13C-NMR and HPLC-DAD methods. The pancreatic lipase inhibitory activities of isolated compounds were evaluated in vitro. Additionally, the anti-obesity and gut microbiota modulation effect of FM on high-fat diet-induced obesity in C57BL/6 mice were also studied in vivo. The results showed that 19 secoiridoids were isolated from FM and identified. The total content of secoiridoids in FM reached 181.35 mg/g and the highest content was nuzhenide (88.21 mg/g). All these secoiridoid compounds exhibited good pancreatic lipase inhibitory activity with inhibition rate ranged from 33.77% to 70.25% at the concentration of 100 µM. After obese mice were administrated with FM at 400 mg/kg.bw for 8 weeks, body weight was decreased by 15.81%. Moreover, FM could attenuate the lipid accumulation in serum and liver, relieve the damage in liver and kidney, and extenuate oxidative stress injury and inflammation caused by obesity in mice. FM could also modulate the structural alteration of gut microbiota in obese mice, increasing the proportion of anti-obesity gut microbiota (Bacteroidetes, Bacteroidia, S24-7 and Allobaculum), and reducing the proportion of obesogenic gut microbiota (Firmicutes and Dorea). This study suggests that F. mandshurica seeds or their secoiridoids may have potential for use as a dietary supplement for obesity management.


Subject(s)
Anti-Obesity Agents/pharmacology , Diet, High-Fat , Feeding Behavior , Fraxinus/chemistry , Gastrointestinal Microbiome/drug effects , Iridoids/pharmacology , Plant Extracts/pharmacology , Seeds/chemistry , Alanine Transaminase/blood , Albuminuria/blood , Animals , Aspartate Aminotransferases/blood , Blood Urea Nitrogen , Body Weight/drug effects , Dinoprostone/blood , Enzyme Inhibitors/pharmacology , Inflammation Mediators/metabolism , Interleukin-6/blood , Lipase/antagonists & inhibitors , Lipase/metabolism , Lipids/blood , Liver/drug effects , Liver/injuries , Liver/metabolism , Male , Malondialdehyde/metabolism , Mice, Inbred C57BL , Mice, Obese , Oxidative Stress/drug effects , Phylogeny , Swine , Tumor Necrosis Factor-alpha/blood
3.
J Food Drug Anal ; 25(4): 992-999, 2017 Oct.
Article in English | MEDLINE | ID: mdl-28987377

ABSTRACT

Amorpha fruticosa L. is a Chinese folk medicine and rich in polyphenols. Fifteen known compounds were isolated and identified from the leaves of A. fruticosa L. They are tephrosin (1), 6a,12a-dehydrodeguelin (2), vitexin (3), afrormosin-7-O-ß-d-glucopyranoside (4), 2″-O-α-l-rhamnopyranosyl isovitexin (5), rutin (6), chrysoeriol (7), 7-O-methylluteolin (8), trans-p-coumaric acid (9), 2-benzyl-4,6-dihydroxybenzoic acid-4-O-ß-d-glucopyranoside (10), formononetin (11), quercetin (12), apigenin (13), ß-sitosterol (14), and ß-daucosterol (15). Compounds 3, 4, 5, and 7-9 were isolated from A. fruticosa L. for the first time. Cytotoxicity of individual compounds 3-10 and 90% ethanol extract against human cancer cell lines HCT116 and HepG2 were reported. The results suggested that compounds 7 and 8, and the crude extract exhibited inhibitory effects on human cancer cell line HCT116, at concentrations of 100 µg/mL, 5 µg/mL, and 25 µg/mL at <60% of cell viability rate, respectively. In addition, a valid high-performance liquid chromatography diode array detector method was established to quantitatively analyze compounds 1-12 in the leaves of A. fruticosa L., which was harvested at three different stages of maturity from May 20 to August 10, 2014. The results demonstrated that contents were greatly influenced by the maturity. Total amounts of the analytical constituents gradually increased from May 20 to August 10, with the values ranging from 10.86 mg/g to 18.84 mg/g, whereas bioactive compounds 7 and 8 presented the opposite variation trend. The results of this study may provide data for further study and comprehensive utilization of A. fruticosa L.


Subject(s)
Fabaceae/chemistry , Plant Extracts/chemistry , Cell Line, Tumor , Cell Survival/drug effects , Humans , Plant Extracts/isolation & purification , Plant Extracts/pharmacology , Plant Leaves/chemistry
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