ABSTRACT
Five alkaloids were isolated from a decoction of Uncaria rhynchophylla by a combination of various chromatographic techniques, including macroporous adsorbent resin, MCI resin, silica gel, Sephadex LH-20, and reversed phase HPLC. Their structures were characterized by comprehensive analyses of spectroscopic data as monoterpene indole alkaloids (+)-(7R)-3-oxo-7-hydroxy-3,7-seco-dihydrorhynchohylline (1), (+)-(7S)-3-oxo-7-hydroxy-3,7-seco-dihydrorhyncho-hylline (2), (+)-(7R)-3-oxo-7-hydroxy-3,7-seco-rhynchohylline (3) and (+)-(7S)-3-oxo-7-hydroxy-3,7-seco-rhynchohylline (4), and a β-carboline alkaloid 1,2,3,4-tetrahydro-1-oxo-β-carboline (5). Among them, 1 and 2 are new compounds, 3 and 4 are new natural products that were semi-synthesized from isorhynchohylline with incorrect specific rotations, and 5 is isolated for the first time from the genus Uncaria.
ABSTRACT
Objective To study the alkaloids from the stems of Picrasma quassioidies. Methods The isolation and purification were carried out by column chromatography on CG161M, silica gel, ODS, and Sephadex LH-20. The structures were elucidated on the basis of physicochemical properties and spectroscopic analysis. Results A total of 16 alkaloids were isolated and identified from 85% ethanol aqueous extract of the stems of P. quassioidies. It included 12 β-carboline alkaloids including 1-(1-hydroxy)-ethyl-6-hydroxy-β-carboline (1), 6-hydroxy-β-carboline-1-carboxylic acid (2), β-carboline-1-carboxylic acid (3), β-carboline-1-propanoic acid (4), 3-hydroxy-β-carboline (5), 1-acetyl-β-carboline (6), 1-ethoxycarbonyl-β-carboline (7), 1-(9H-β-carbolin-1-yl)-ethanol (8), picrasidine X (9), 1-hydroxymethyl-β-carboline (10), 9H-pyrido [3,4-b] indole (11), 6-hydroxy-2-methyl-9H-β-carbolin-2-ium (12); and four cantin-6-one alkaloids, including 4,5-dimethoxycanthin-6-one (13), 3-methylcanthin-5,6-dione (14), 5-hydroxy-4-methoxylcanthin-6-one (15), and picrasidine O (16). Conclusion Compound 1 is a new β-carboline alkaloid named picrasidine Z, and compound 12 is a new natural product.
ABSTRACT
AIM@#To study the chemical constituents from the seeds of Griffonia simplicifolia Baill.@*METHODS@#The chemical constituents were isolated and purified by a combination of chromatographic materials including silica gel, Sephadex LH-20, and preparative TLC. Their structures were elucidated on the basis of MS and NMR data analysis. The cytotoxic activities were evaluated against HepG2 cancer cell line using the MTT colorimetric method.@*RESULTS@#A new β-carboline alkaloid, griffonine (1), together with seven known alkaloids, hyrtioerectine B (2), 3-carboxy-6-hydroxy-β-carboline (3), hyrtiosulawesine (4), 5-hydroxyindole-3-carbaldehyde (5), 5-hydroxy-3-(2-hydroxyethyl) indole (6), trigonelline (7), and 5-hydroxytryptamine (8) were isolated and identified. Alkaloids 1, 2 and 4 showed growth inhibitory effects on the HepG2 cell line with IC50 values of 23.5, 9.6 and 19.3 μmol·L(-1), respectively.@*CONCLUSION@#Alkaloid 1 is new and was named griffonine. Alkaloids 2-7 were isolated from this plant for the first time. Alkaloids 1, 2 and 4 were potentially cytotoxic.
Subject(s)
Humans , Alkaloids , Chemistry , Pharmacology , Carbolines , Chemistry , Pharmacology , Cell Proliferation , Griffonia , Chemistry , Hep G2 Cells , Plant Extracts , Chemistry , Pharmacology , Seeds , ChemistryABSTRACT
Objective: Isolation and identification of chemical components from the root bark of Ailanthus altissima by HPLC method. Methods: Crude products which were extracted with ethanol were separated and purified by preparative HPLC, and the structures of the compounds were identified by mass spectrometry (MS), 1H-NMR, and 13C-NMR. Results: Under the above conditions, ailanfhone (1), shinjulactone A (2), and a new β-carboline alkaloid (3) were successfully obtained, and the purities of the compounds are all above 95%. Conclusion: A rapid and simple method is set up to isolate and identify lower content components from A. altissima.