Entadamide A

Chem Pharm Bull (Tokyo) . 1989 Jul;37(7):1932-1933.

Synthesis of entadamide A and entadamide B isolated from Entada phaseoloides and their inhibitory effects on 5-lipoxygenase[Pubmed: 2805174]

Two new sulfur-containing amides, Entadamide A (1) and entadamide B (2), isolated from the seeds of Entada phaseoloides, were synthesized by the addition reaction of methanethiol to propiolic acid (5) followed by condensation with ethanolamine by the use of dicyclohexylcarbadiimide. These compounds inhibited the 5-lipoxygenase activity of RBL-1 cells at 10(-4) g/ml. This finding suggests that entadamides A and B may be examples of a new type of antiinflammatory drug.

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]

Abstract 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.

Chem Pharm Bull (Tokyo) . 2003 Dec;51(12):1423-1425.

Sulfur-containing compounds from Clinacanthus siamensis[Pubmed: 14646322]

Two new sulfur-containing compounds, trans-3-methylsulfonyl-2-propenol (1) and trans-3-methylsulfinyl-2-propenol (2) were isolated together with trans-3-methylthioacrylamide (3), Entadamide A (4) and entadamide C (5) from the leaves of Clinacanthus siamensis. The structures were established on the basis of the spectroscopic data. The compounds were tested for antimalarial and antimycobacterial activity.

J Ayurveda Integr Med . Oct-Dec 2020;11(4):464-470.

Effect of seeds of Entada phaseoloides on chronic restrain stress in mice[Pubmed: 30635249]

Background: Entada phaseoloides is a well-known medicinal plant traditionally used in Ayurvedic medicine for centuries. Objective: To evaluate the anti-stress activity of seeds of E. phaseoloides in endoplasmic reticulum stress during chronic restrain stress in mice, based on our preliminary screening. Materials and methods: Mice (n = 6/group) were restrained daily for 6 h in 50 ml polystyrene tubes for 28 days. Methanolic extract of E. phaseoloides (MEEP) (100 and 200 mg/kg, p.o.) and standard drug, imipramine (10 mg/kg i.p.) were administered daily 45 min prior to restrain from day 22-28. Then, forced swim test (FST) was performed to assess despair behavior. Lipid peroxidation (LPO) and antioxidant enzymes Reduced glutathione (GSH), Superoxide dismutase (SOD) were measured in the hippocampus of mice. 78 kDa Glucose-regulated Protein, 94 kDa Glucose-regulated Protein, C/EBP homologous protein, Caspase-12 expression were quantified by Real Time PCR. Results: MEEP significantly reduced the immobility time in FST (P < 0.001). Significant reduction of LPO (P < 0.05) level and restored antioxidant enzymes viz. GSH (P < 0.001) and SOD towards vehicle control group were observed. Down-regulation of genes GRP 78, GRP 94 (P < 0.001), CHOP and Caspase-12 (P < 0.001) as compared to the chronic restrain stress group was evident, which were upregulated following treatment. Isolation of the active components of the seeds revealed the presence of Oleic acid (1), Entadamide A (2), Entadamide A-beta-d-glucopyranoside (3) and 1-O-protocatechuoyl-β-d-glucose. Conclusion: MEEP altered endoplasmic reticulum stress in chronic restrain stressed mice; however, as an antidepressant it showed a weaker response.

Yao Xue Xue Bao . 2010 May;45(5):624-626.

Sulfur-containing amides from Entada phaseoloides[Pubmed: 20931765]

To study the chemical constituents of the Entada phaseoloides (L.) Merr., seeds of Entada phaseoloides were extracted with 70% ethanol at room temperature. Isolation and purification were performed by silica gel, reversed-phase silica gel column chromatography and semi-preparative HPLC. Structures of the pure compounds were established on the basis of spectral analysis. Four sulfur-containing amide compounds were isolated from the n-BuOH-soluble fraction and identified as Entadamide A-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranoside (1), Entadamide A (2), Entadamide A-beta-D-glucopyranoside (3) and clinacoside C (4). Compound 1 is a new compound. Compound 4 is isolated from the genus Entada for the first time.