ABSTRACT
Systematic phytochemical investigation on the Mongolian medicinal herb Lomatogonium carinthiacum led to the isolation of 12 monoterpenoids including three new secoiridoids (1, 2 and 4) and one new iridoid glycoside (13), one new monoterpenoid alkaloid (3), and three new sesquiterpenoids (14-16). Comprehensive spectroscopic analysis (including 1D and 2D NMR, and HRESIMS) and quantum chemistry computations (including ECD and NMR calculations) were applied to elucidate their structures. Weak immunosuppressive activities were observed for the new isolates via inhibiting T cell proliferation and cytokine IFN-γ secretion in vitro.
Subject(s)
Gentianaceae , Plants, Medicinal , Molecular Structure , Medicine, Mongolian Traditional , Glycosides/chemistry , Plant Extracts/chemistry , Gentianaceae/chemistryABSTRACT
Objective: To study the chemical constituents from traditional Chinese (Mongolian) medicine, Lomatogonium carinthiacum and Halenia corniculate. Methods: The chemical constituents were isolated and purified by silicagel column, Sephadex LH-20, ODS and high performance liquid chromategramphy. The structures were identified by NMR and MS analysis technics. Results: Twelve compounds were isolated and identified as isovitexin (1), Luteolin-5-O-ß-D-glucoside (2), Isosaponarin (3), Luteolin-7-O-ß-D-glucoside (4,7), 1,4,8-Trimethoxy-xanthone-6-O-ß-D-glucoronyl-(1 â 6)O-ß-Dglucoside (5), friginosideD (6), 1-hydroxy-2,3,5-trimethoxyxanthone (8), 1-hydroxy-2,3,4,5-tetramethoxyxanthone (9), 1-hydroxy-2,3,4,7-tetramethoxyxanthone(10), 1-hydroxy-2,3,4,5,7-pentamethoxyxanthone (11) and usnic acid (12). Conclusion: Compounds 6 and 12 are obtained from L. carinthiacum and H. corniculate for the first time.
ABSTRACT
Objective: To study the chemical constituents from traditional Chinese (Mongolian) medicine, Lomatogonium carinthiacum and Halenia corniculate. Methods: The chemical constituents were isolated and purified by silicagel column, Sephadex LH-20, ODS and high performance liquid chromategramphy. The structures were identified by NMR and MS analysis technics. Results: Twelve compounds were isolated and identified as isovitexin (1), Luteolin-5-O-β-D-glucoside (2), Isosaponarin (3), Luteolin-7-O-β-D-glucoside (4,7), 1,4,8-Trimethoxy-xanthone-6-O-β-D-glucoronyl-(1 → 6)O-β-Dglucoside (5), friginosideD (6), 1-hydroxy-2,3,5-trimethoxyxanthone (8), 1-hydroxy-2,3,4,5-tetramethoxyxanthone (9), 1-hydroxy-2,3,4,7-tetramethoxyxanthone(10), 1-hydroxy-2,3,4,5,7-pentamethoxyxanthone (11) and usnic acid (12). Conclusion: Compounds 6 and 12 are obtained from L. carinthiacum and H. corniculate for the first time.
ABSTRACT
Three biflavonoid glycosides, named carinoside B, C and D (1, 2 and 3, respectively), were isolated from the n-BuOH crude extract of the aerial part of Lomatogonium carinthiacum (Wulfen) Rchb (L. carinthiacum). The structures of 1, 2 and 3 were elucidated by spectroscopic methods, including UV, IR, HR-ESI-MS and extensive 1D and 2D NMR techniques.
Subject(s)
Biflavonoids/chemistry , Gentianaceae/chemistry , Glycosides/chemistry , Biflavonoids/isolation & purification , Glycosides/isolation & purification , Molecular Structure , Plant Components, Aerial/chemistry , Plant Extracts/chemistryABSTRACT
A biflavonoid glycoside with a new carbon skeleton, named carinoside A, was isolated from the n-BuOH crude extract of the whole plant of Lomatogonium carinthiacum (Wulf) Reichb. The structure of the new compound was elucidated by using spectroscopic methods, including UV, IR, HR-ESI-MS and extensive 1D and 2D NMR techniques.
Subject(s)
Biflavonoids/isolation & purification , Drugs, Chinese Herbal/isolation & purification , Gentianaceae/chemistry , Glycosides/isolation & purification , Biflavonoids/chemistry , Drugs, Chinese Herbal/chemistry , Glycosides/chemistry , Molecular Structure , Nuclear Magnetic Resonance, BiomolecularABSTRACT
AIM: To study the chemical constituents of Lomatogonium carinthiacum (Wulfen) Rchb. METHOD: The CHCl3-soluble fraction was separated by chromatography and the structures of the new compounds were elucidated by spectral experiments. RESULTS: Two new xanthones, 1, 8-dihydroxy-4, 5-dimethoxy-6, 7-methylenedioxyxanthone (1), 1, 4, 8-trimethoxyxanthone-6-O-ß-D-glucoronyl-(1â6)O-ß-D-glucoside (2) were isolated from the whole plant of Lomatogonium carinthiacum. CONCLUSION: Compounds 1 and 2 are new natural products.
Subject(s)
Gentianaceae/chemistry , Glucosides/isolation & purification , Plant Extracts/chemistry , Xanthones/isolation & purification , Glucosides/chemistry , Molecular Structure , Xanthones/chemistryABSTRACT
Two new unusual xanthones, 5-O-ß-d-glucopyranosyl-1,3,8-trihydroxy-5,6,7,8-tetrahydroxanthone (1) and 1,3,5,8-tetrahydroxy-5,6,7,8-tetrahydroxanthone (2), were isolated from Lomatogonium carinthiacum (Wulf) Reichb. Their structures were elucidated on the basis of spectroscopic methods including UV, IR, ESI-MS, 1D NMR, and 2D NMR.
Subject(s)
Gentianaceae/chemistry , Magnetic Resonance Spectroscopy/methods , Models, Chemical , Models, Molecular , Plant Extracts/chemistry , Xanthones/chemistry , Molecular ConformationABSTRACT
AIM@#To study the chemical constituents of Lomatogonium carinthiacum (Wulfen) Rchb.@*METHOD@#The CHCl3-soluble fraction was separated by chromatography and the structures of the new compounds were elucidated by spectral experiments.@*RESULTS@#Two new xanthones, 1, 8-dihydroxy-4, 5-dimethoxy-6, 7-methylenedioxyxanthone (1), 1, 4, 8-trimethoxyxanthone-6-O-β-D-glucoronyl-(1→6)O-β-D-glucoside (2) were isolated from the whole plant of Lomatogonium carinthiacum.@*CONCLUSION@#Compounds 1 and 2 are new natural products.
