ABSTRACT
The present study is to investigate the chemical constituents and anti-inflammation of agarwood produced via whole-tree agarwood-inducing technique( Agar-Wit) from Aquilaria sinensis by column chromatographic technique and semi-preparation HPLC.Eleven sesquiterpenes were isolated from the agarwood produced by Agar-Wit,and their structures were identified on the basis of physiochemical characteristics and spectroscopic data analysis as baimuxinol( 1),5α,7α( H)-eudesm-11( 13)-en-4α-ol( 2),( 7 S,9 S,10 S)-( +)-9-hydroxy-selina-4,11-dien-14-al( 3),petafolia A( 4),7( 11)-eremophilen-8-one( 5),neopetasane( 6),petafolia B( 7),11-hydroxy-valenc-1( 10)-en-2-one( 8),( 4αβ,7β,8αβ)-3,4,4α,5,6,7,8,8α-octahydro-7-[1-( hydroxymethyl) ethenyl]-4α-methylnaphthalene-1-carboxaldehyde( 9),12-hydroxy-4( 5),11( 13)-eudesmadien-15-al( 10),and( 4 R,5 R,7 S,9 S,10 S)-(-)-eudesma-11( 13)-en-4,9-diol( 11). Among them,compound 1 was a new natural product,and this is the first time to report its13 CNMR spectroscopic data. Compounds 4,9 and 10 were reported from Aquilaria for the first time,and all the compounds are firstly isolated by Agar-Wit from A. sinensis. The anti-inflammatory activity of RAW264. 7 cells with lipopolysaccharide-induced was evaluated.As a result,1,4 and 9 showed potential anti-inflammatory activities with IC50 values( 2. 5±0. 35),( 3. 2±0. 2),( 4. 3±0. 56) μmol·L-1,respectively. This work provided scientific foundation for quality evaluation of the agarwood produced by Agar-Wit.
Subject(s)
Anti-Inflammatory Agents , Lipopolysaccharides , Sesquiterpenes , Thymelaeaceae , TreesABSTRACT
OBJECTIVE: To investigate the chromones and anti-inflammation effect of agarwood produced via whole-tree agarwood-inducing technique (Agar-Wit) from A. sinensis. METHODS: The constituents were isolated and purified by chromatographic technique and semi-preparation HPLC. RAW264.7 cell model induced by lipopolysaccharide was used to evaluate the anti-inflammatory activity of some compounds, and the secretion level of TNF-α was detected by ELISA. RESULTS: A new 2-(2-phenylethyl) chromone, (7'R)-2-[2-(7'-hydroxyphenyl)ethyl] chromone (1), along with nine analogues (2-10) were isolated from the agarwood produced by Agar-Wit, their structures were identified on the basis of physicochemical characteristics and spectroscopic data analysis as 6,7-dimethoxy-2-[2-(7'-hydroxyphenyl)ethyl] chromone (2), 6-hydroxy-2-[2-(7'-hydroxyphenyl)ethyl] chromone (3), 8-chloro-6-hydroxy-2-(2-phenylethyl)chromen-4-one (4), 8-chloro-6-hydroxy-2-[2-(4'-methoxyphenyl)ethyl] chromone (5), 8-chloro-6-hydroxy-2-[2-(3'-hydroxy-4'-methoxyphenyl)ethyl] chromone (6), 7-hydroxy-6-methoxy-2-(2-phenylethyl) chromone (7), 6-hydroxy-7-dimethoxy-2-[2-(4'-hydroxyethyl)] chromone (8), 6-hydroxy-2-[2-(3'-methoxy-4'-hydroxy)ethyl] chromone (9), 6-hydroxy-2-[2-(3'-hydroxy-4'-methoxyphenyl)ethyl] chromone (10). The results showed that compounds 1, 4, 6, 9 significantly inhibited the release of TNF-α inflammatory factors in RAW264.7 cells induced by LPS, with IC50 values of 13.30, 8.53, 7.72, and 10.87 μg•mL-1, respectively. CONCLUSION: Compound 1 is a new compound. The crystal structure of compound 4 is reported for the first time. Compounds 1, 4, 6, 9 show significant anti-inflammation activities.