ABSTRACT
Three new thionic compounds, ()-2-(2-carboxyl-2-hydroxyethylthio)-ferulic acid (), ()-2-methoxy-4-(3-(methylsulfonyl)prop-1-en-1-yl)phenol (), and thiosenkyunolide C (), together with two new aromatic glycosides ( and ) were isolated from the rhizome of Hort. Two known compounds ( and ) were also obtained. Their structures were elucidated based on extensive spectroscopic data (UV, IR, 1D and 2D NMR, and HR-ESI-MS). Furthermore the absolute configurations were established by comparison of their calculated and experimental circular dichroism spectra and by a dimolybdenum tetraacetate [Mo(AcO)]-induced circular dichroism procedure. All compounds were evaluated against lipopolysaccharide (LPS)-induced NO production in BV2 cells, and compounds and showed strong inhibitory activities with IC values of 2.03 and 3.09 µmol/L, respectively (positive control curcumin, IC = 6.17 µmol/L). In addition, compound showed weak proteintyrosine phosphatase-1B (PTP1B) inhibitory activity.
ABSTRACT
Twenty five known aromatic glycosides (1-25) and three known sesquiterpene glycosides (26-28) have been isolated from the twigs of Litsea cubeba by using various chromatographic techniques. Their structures were identified by spectroscopic data analysis (MS, IR, 1D and 2D NMR) as (7S,8R)-dehydrodiconiferyl alcohol 4,9'-di-O-β-D-glucopyranoside(1),(7S,8R)-5-methoxydihydrodehydrodiconiferyl alcohol 4-O-β-D-glucopyranoside(2), (7S,8R)-urolignoside(3), (7R,8S)-dihydrodehydrodiconiferyl alcohol 4-O-β-D-glucopyranoside(4), saposide B(5), lanicepside A(6), matairesinol-4-O-β-D-glucopyranoside (7), tyraxjaponoside B(8), (+)-lyoniresinol-9'-O-β-D-glucopyranoside (9), alaschanisoside A (10), syringin (11), psoralenoside (12), isopsoralenoside (13), scopolin(14), 2,6-dimethoxy-4-hydroxyphenol-1-O-β-D-glucopyranoside (15), 3-hydroxy-4,5-dimethoxyphenyl-β-D-glucopyranoside (16), 2-(3,4-dihydroxyphenyl)ethyl-β-D-glucopyrnoside (17), 2-(4-dihydroxyphenyl)ethyl-β-D-glucopyranoside (18), (+)-catechin-7-O-β-D-glucopyranoside (19), 3'-O-methylepicatechin-7-O-β-D-glucopyranoside (20), kaempferitrin (21), quercetin-3-O-α-L-rhamnopyranside (22), kaempferol-3-O-β-D-glucopyranoside (23), kaempferol 3-O-β-D-glucopyranosyl(1→2)-O-β-D-galactopyr anoside-7-O-α-L-rhamnopyranoside (24), quercetin 3-O-α-L-rhamnopyranosyl(1→6)-O-β-D-glucopyranosyl(1→3)-O-α-L-rhamnopyranosyl(1→2)-O-β-D-glucopyranoside (25), staphylionoside D(26), vomifoliol 9-O-β-D-glucopyranoside (27), dihydrovomifoliol-O-β-D-glucopyranoside (28). Compounds 1-21 and 24-28 were obtained from this genus for the first time.