Anti-complementary constituents of Myricaria wardii
Objective To study the anti-complementary constituents of Myricaria wardii. Methods The compounds were isolated and purified by silica gel column chromatography,gel chromatography,ODS column chromatography,and semi-preparative HPLC. The structures were identified by spectral data (NMR and MS) and relevant references. Besides,the anti-complementary activities of these compounds were evaluated by hemolysis method. Results A total of 41 compounds were isolated and identified from M. wardii,including (−)-3,6-bis(4-hydroxy-3-methoxyphenyl)-5-(4-hydroxyphenethyl)hexahydro-4H-furo[3,4-c]pyrrol-4-one (1),methyl 3-hydroxy-4,5-dimethoxybenzoate (2),methyl 3-hydroxy-4-methoxybenzoate (3),vanillin (4),apocynin (5),methyl syringate (6),coniferaldehyde (7),methyl 3,4-dihydroxy-5-methoxybenzoate,(8),methyl isoferulate (9),p-hydroxybenzaldehyde (10),p-hydroxyacetophenone (11),loliolide (12),(+)-dehydrovomifoliol (13),gallic acid (14),protocatechuic acid (15),3-O-methylgallic acid (16),ethyl gallate (17),vomifoliol (18),3,5,6-trihydroxy-7-megastigmen-9-one (19),caffeic acid (20),grasshopper ketone (21),taxifolin (22),3-hydroxy-4,5-dimethoxybenzoic acid (23),p-coumaric acid (24),syringic acid (25),isolariciresino (26),burselignan (27),(1',1',2',2'-tetramethylpropyl)-1,2-benzenediol (28),dihydrokaempferol (29),quercetin (30),N-trans-feruloyltyramine (31),terrestiamide (32),(R)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4hydroxyphenyl)-2-methoxyethyl]acrylamide (33),(Z)-8,11,12-trihydroxy-9-octadecanoic acid (34),9,12,13-trihydroxy-10,15-octadecadienoic acid (35),myricaria A (36),isoferulic acid (37),protocatechualdehyde (38),N-trans-feruloyl-3-methyldopamine (39),kaempferol (40),methyl vanillate (41). A total of 26 compounds,including 13 phenolic acid derivates,four flavonoids,two lignans,three phenylpropanoids,three phenolic amides and one terpenoid,showed anti-complementary activities with the half inhibit hemolysis concentration (CH50) ranging from (0.20±0.03) to (4.72±0.01) mmol/L. Conclusion Compound 1 is a new compound isolated from M. wardii named myricarian A,and sesquiterpenoids (12,13,18,19,21) are isolated from Myricaria for the first time. Phenolic derivates and flavonoids are considered as the main anti-complementary components of M. wardii.
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