Résumé
Objective: To study the chemical constituents in the whole herb of Lycopodium japonicum. Methods: The constituents were isolated and purified by silica gel and semi-preparative HPLC, and their structures were elucidated by means of physicochemical properties and spectroscopic analysis. All the isolated compounds were evaluated using relevant in vitro anti-inflammatory assay against LPS-induced NO releases. Results: Nineteen compounds were isolated from the whole herb of L. japonicum, and identified as lycoposerramine-M N-oxide (1), acetyllycoposerramine-M (2), lycopodine (3), lycoposerramine-M (4), miyoshianine-C (5), 12-epilycodoline N-oxide (6), gnidioidine (7), lycoposerramine-K (8), lucidioline (9), 4α-hydroxyanhydrolycodoline (10), flabelline (11), hydroxypropyllycodine (12), lycodine (13), des-N-methyl-α-obscurine (14), α-obscurine (15), des-N-methyl-β-obscurine (16), lycoflexine (17), lycoflexine N-oxide (18), and fawcettidine (19). Compound 5 and 18 could inhibit the release of nitric oxide (NO) in the RAW264.7 cell line stimulated by lipopolysaccaride. The IC50 values of 5 and 18 are 31.82 and 40.69 μmol/L, respectively. Conclusion: Compound 1 is a new compound, named lycoposerramine-M N-oxide, compounds 2, 6, 11, 12, 16, 18, and 19 are isolated from this plant for the first time. Compounds 5 and 18 exhibit the potent inhibitory activity.
Résumé
Objective: To study the chemical constituents in the whole herb of Lycopodium japonicum. Methods: The chemical constituents were separated and purified by silica gel, Sephadex LH-20 column chromatography, and preparative HPLC. Their structures were identified by various spectroscopic analyses. Results: Thirteen compounds were obtained from the whole herb of L. japonicum by the chromatographic methods on silica gel, ODS, and Sephadex LH-20 column, and preparative HPLC. According to physicochemical properties and spectral data, these compounds were identified as betulin (1), di-(2-ethylhexyl) phthalate (2), α-onocerin (3), 16-oxo-3α-hydroxyserrat-14-en-21β-ol (4), 3-epilycoclavanol (5), (24S)-24-methyl cholesterol (6), lycopodiin A (7), tomentosanan B (8), α-obscurine (9), lycoclavanol (10), serratenediol (11), 1, 2-diarylpropane-3-ol (12), and 13, 13-ethylenedioxy-15, 16-dinwlabd-7-en-6β-ol (13). Conclusion: Compounds 1, 2, 6, 8, and 11-13 are isolated from this plant for the first time. Compounds 2, 6, 8, and 12 are isolated from the plants of this genus for the first time.
Résumé
Objective: To investigate the chemical constituents in the whole plant of Lycopodium japonicum, native to Suizhou city, Hubei province for the first time. Methods: The compounds were isolated and purified by a combination of silica gel, ODS, and Sephadex LH-20 column chromatography and prep-HPLC. Their chemical structures were established by their physicochemical properties and spectral data. Results: Eight pentacyclic triterpenoids have been isolated and characterized from the methanol extract of the whole plant, they are 21-episerratenediol (1), serratenediol (2), α-onocerin (3), serrat-14-en-3β, 21β, 24-triol (4), 3β, 21α- dihydroxyserrat-14-en-16-one (5), lycoclavanol (6), lyclaninol (7), and 3α, 21β, 24-trihydroxyserrat-14-en-16-one (8). Conclusion: Compounds 1-8 are all serretene triterpenoids, the characteristic chemical constituents in the plants of genus Lycopodium L. Compound 5 is isolated from this plant for the first time.