| In vitro: |
| J Nat Med . 2015 Apr;69(2):171-177. | | Intestinal bacterial metabolism and anti-complement activities of three major components of the seeds of Entada phaseoloides[Pubmed: 25398297] | | The present study aimed to investigate the metabolism of Entadae Semen by human fecal bacteria to clarify the relationship between its pharmacological activities and intestinal metabolism. Three major components (Phaseoloidin, entadamide A-β-D-glucopyranoside and entadamide A) were isolated and identified from Entadae Semen and then incubated with human fecal microflora in vitro to investigate the metabolic processes. The metabolites were analyzed with high-performance liquid chromatography (HPLC). The anti-complement activities of the three components and their metabolites produced by human fecal microflora were evaluated in vitro using a hemolysis assay. Phaseoloidin and entadamide A-β-D-glucopyranoside were metabolized into their respective aglycones during the incubation process, which enhanced their anti-complement effects. These results indicated that the presence of intestinal bacteria likely plays an important role and that the pharmacological effects of Entadae Semen may be dependent on intestinal bacterial metabolism. | | Biomed Chromatogr . 2021 Dec;35(12):e5232. | | Optimization, extraction, and purification of three bioactive compounds from Entada phaseoloides by high-speed countercurrent chromatography[Pubmed: 34424556] | | The objective of this paper was to develop a preparative method for the separation and purification of Phaseoloidin, entadamide A, and entadamide A-β-D-glucopyranoside from the crude extract of Entada phaseoloides by high-speed countercurrent chromatography (HSCCC) for the first time. Optimized by orthogonal experiments, the extraction conditions were extraction temperature of 65°C, solid-to-liquid ratio of 1:15 (g/mL), ethanol concentration of 40%, and extraction time of 2.5 h. Using n-butanol-acetic acid-water (4:1:5, v/v/v) as the two-phase solvent system, 38.79 mg Phaseoloidin (the purity was 99.3% with a recovery of 98.1%), 34.85 mg entadamide A (the purity was 96.4% with a recovery of 98.5%), and 33.97 mg entadamide A-β-D-glucopyranoside (the purity was 98.6% with a recovery of 97.7%) were obtained from 500 mg crude extract by HSCCC in head-to-tail elution mode. The retention ratio of stationary phase was 51.0%. According to the antioxidant activity assays, Phaseoloidin, entadamide A, and entadamide A-β-D-glucopyranoside had certain scavenging abilities on 1,1-diphenyl-2-picrylhydrazyl free radicals and hydroxyl free radicals. |
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| In vivo: |
| J Chem Ecol . 2011 Oct;37(10):1091-1098. | | Phaseoloidin, a homogentisic acid glucoside from Nicotiana attenuata trichomes, contributes to the plant's resistance against lepidopteran herbivores[Pubmed: 21904938] | | Plant trichomes are known for their capability to produce and store secondary metabolites that protect plants from biotic and abiotic stresses. (1)H NMR studies on intact individual trichomes located on the leaf surface of Nicotiana attenuata revealed the presence of two major secondary metabolites: nicotine, the signature metabolite of the genus, and Phaseoloidin, a homogentisic acid glucoside. This glucoside was reported originally from the seeds of Entada phaseoloides, and this is the first report of its occurrence in a Solanaceous plant. Artificial diet feeding bioassays with Manduca sexta and Spodoptera littoralis larvae, two important herbivores of N. attenuata, revealed that the ingestion of Phaseoloidin negatively influenced caterpillar performance. This effect was more pronounced for the generalist, S. littoralis, than for the specialists, M. sexta. |
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