Tetrahydroxanthones from Mongolian medicinal plant Gentianella amarella ssp. acuta

Abstract

Two tetrahydroxanthones, 1,3,5S,8S-tetrahydroxy-5,6,7,8-tetrahydroxanthone (1) and 1,3,5R,8S-tetrahydroxy-5,6,7,8-tetrahydroxanthone (2), and six new tetrahydroxanthone glycosides, amarellins A-F (3-8), were isolated from the aerial parts of a Mongolian medicinal plant Gentianella amarella ssp. acuta (Gentianaceae). The structures of 1-8 were elucidated on the basis of spectroscopic analysis, chemical conversion, and ECD calculation. Amarellins A-C (3-5) were assigned as 8-O-β-D-glucoside, 8-O-β-D-xyloside, and 1-O-β-D-glucoside of 1, respectively, while amarellins D-F (6-8) were elucidated to be 8-O-β-D-xyloside, 1-O-β-D-glucoside, and 3-O-β-D-glucoside of 2, respectively.

Phytochemical studies on traditional herbal medicines based on the ethnopharmacological information obtained by field studies

“…The phytochemical investigation of the aerial parts of G. amarella ssp. acuta gave two tetrahydroxanthones, 1,3,5S,8S-tetrahydroxy-5,6,7,8tetrahydroxanthone (58) and 1,3,5R,8S-tetrahydroxy-5,6,7,8tetrahydroxanthone (59), and six new tetrahydroxanthone glycosides, amarellins A-F (60-65) [61]. Yang et al also isolated 60-65 from the same plant materials, and evaluated for their inhibitory effects on the isolated intestinal smooth muscle contractions.…”

“…The phytochemical investigation of the aerial parts of G. amarella ssp . acuta gave two tetrahydroxanthones, 1,3,5 S ,8 S -tetrahydroxy-5,6,7,8-tetrahydroxanthone ( 58 ) and 1,3,5 R ,8 S -tetrahydroxy-5,6,7,8-tetrahydroxanthone ( 59 ), and six new tetrahydroxanthone glycosides, amarellins A–F ( 60 – 65 ) [ 61 ]. Yang et al .…”

Xanthones and Cancer: from Natural Sources to Mechanisms of Action

“…Whole plant no [42] 8-O-β-D-Glucopyranosyl-1-hydroxy-2,3,5-trimethoxyxanthone Swertia mussotii Whole plant no [55] Amarellin A Gentianella amarela Aerial parts no [21] Amarellin B Gentianella amarela Aerial parts no [21] Amarellin C Gentianella amarela Aerial parts no [21] Amarellin D Gentianella amarela Aerial parts no [21] Amarellin E Gentianella amarella Aerial parts no [21] Amarellin F Gentianella amarela Aerial parts no [21] Angustin A Swertia angustifolia Aerial parts no [56] Angustin B Swertia angustifolia Aerial parts no [56] Banganxanthone C Garcinia polyantha Leaves yes [57] Beccarixanthone T Mesua beccariana Stem barks yes [58] Bellidifolin Swertia punicea Whole plant no [32] Bracteaxanthone III Garcinia bracteata Stem barks yes [24] Bracteaxanthone IV Garcinia bracteata Stem barks yes [24] Bracteaxanthone V Garcinia bracteata Stem barks yes [24] Bracteaxanthone VI Garcinia bracteata Stem barks yes [24] Bracteaxanthone VII Garcinia bracteata Leaves yes [59] Bracteaxanthone VIII Garcinia bracteata Leaves yes [59] Bracteaxanthone IX Garcinia bracteata Leaves yes [59] Bracteaxanthone X Garcinia bracteata Leaves yes [59] Bracteaxanthone XI Garcinia bracteata Leaves yes [59] Bracteaxanthone XII Garcinia bracteata Leaves yes [59] Bracthone A Garcinia bracteata Stems yes [60] Bracthone B Garcinia bracteata Stems yes [60] Butyraxanthone F Pentadesma butyracea…”

Xanthones and Phenylpropanoids from the Whole Herb of Swertia pseudochinensis and Their Anti‐Inflammatory Activity

“…In comparing the 13 In addition, eleven known compounds (2 -12) were separated from the AcOEt extract of S. pseudochinensis. Chemical evidence and analysis of spectroscopic data (1D NMR) allowed the identification of these compounds as tetrahydrobellidifolin (2), [13] 1,3,5R,8S-tetrahydroxy-5,6,7,8-tetrahydroxanthone (3), [14] campestroside (4), [15] amarellin A (5), [14] 1,3,5S,8S-tetrahydroxy-5,6,7,8-tetrahydroxanthone (6), [16] 1,3,7-trihydroxy-8methoxyxanthone ( 7), [17] ficusesquilignan A (8), [18] (7R,7'R,7''R,8S,8'S,8''S)-4',4''-dihydroxy-3,3',3'',5-tetramethoxy-7,9',7',9-diepoxy-4,8''-oxy-8,8'-sesquineolignan-7'',9''-diol ( 9), [19] diospyrosin (10), [13] erythro-7E-4',9'-dihydroxy-4,5'-dimethoxy-5,8'-oxyneolignan-7-en-9-al ( 11), [20] erythro-guaiacylglycerol-β-coniferyl aldehyde ether (12). [21] Furthermore, the inhibitory effects on NO production in LPS-induced RAW 264.7 cells of all compounds have been tested.…”