| Agarwood has been used to setative,carminative,coughs,rheumatism and to relieve gastric problems as a triditional Chinese rare medicinal herbs.So far,domestic and foreign scholars have done a lot of studies on the agarwood originating from Aquilaria sinensis(Lour.)Gilg and Aquilaria malaccensis Lam..But there were few reports for phytochemical study on the agarwood of Aquilaria crassna Pierre ex Lecomte.In order to enrich chemical composition of this genus and to find bioactive compounds for the purpose of development of agarwood,the faty soluble components and their bioactivities were systematically investigated.Thirty-four compounds were isolated from the agarwood originating from Aquilaria crassna by column chromatography.Their structures were indentified by physical,chemical properties and spectral data(UV,IR,MS,1D and 2D-NMR)as 2-[2-hydroxy-2-phenylethyl]chromone(1),5-hydroxy-2-[2-(4-methoxyphenyl)ethenyl]-chromone(2),2-(2-phenylethyl)chromone(3),6-hydroxy-2-(2-phenylethyl)chromone(4),6-methoxy-2-(2-phenylethyl)chromone(5),2-[2-(4-methoxyphenyl)ethyl]chromone(6),6,7-dimethoxy-2-(2-phenylethyl)chromone(7),6-methoxy-2-[2-(4-methoxyphenyl)ethyl]-chromone(8),6-hydroxy-2-[2-(4-methoxyphenyl)ethyl]chromone(9),2-[2-hydroxy-2-(3-methoxy-4-hydroxyphenyl)ethyl]chromone(10),5-hydroxy-6-methoxy-2-[2-(4-methoxy-phenyl)ethyl]chromone(11),6-methoxy-2-[2-(3-methoxy-4-hydroxyphenyl)ethyl]-chrom-one(12),6-methoxy-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]chromone(13),6-hydroxy-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]chromone(14),2-[2-hydroxy-2-(4-methoxyphenyl)ethyl]chromone(15),oxidoagarochromone B(16),oxidoagarochromone C(17),rel-(1aR,2R,3R,7b5)-1a,2,3,7b-tetrahydro-2,3-dihydroxy-5-(2-phenylethyl)-7H-oxi-reno[f][1]benzopyran-7-one(18),rel-(1 aR,2R,3R,7bS)-1a,2,3,7b-tetrahydro-2,3-dihydroxy-5-[2-(4-methoxyphenyl)ethyl]-7H-oxireno[f][1]benzopyran-7-one(19),rel-(1 aR,2R,3R,7b S)-la,2,3,7b-tetrahydro-2,3-dihydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-7H-oxire-no[f][I]benzopyran-7-one(20),(5S,6R,7S,8R)-2-[2-(3’-hydroxy-4’-methoxy-phenyl)ethyl]-5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone(21),(8β,9β，10β)-8,9-epoxycalamen-10-ol(22),11,13-dihydroxy-9(10)-ene-8,12-epoxyemophilane(23),11,13-dihydroxy-eremo-phila-l(10)-ene-2-oxo-ll-methylester(24),7α-H-9(10)-ene-11,12-epoxy-8-oxoeremophi-lane(25),5-desoxylongilobol(26),vanillin(27),syringaldehyde(28),coniferaldehyde(29),mustard aldehyde(30),zingerone(31),5α,8aα-epidioxy-(20S,22E,24R)-ergosta-6,22-diene-3β-ol(32),1-hydroxy-1,5-diphenylpentan-3-one(33)and 5-hydroxy-7,4’-dimethox-yflavone(34).Among all the compounds,compounds 1-2 and compounds 22-24 were new 2-(2-phenylethyl)chromone derivatives and new sesquiterpenes,respectively.Compounds 1-21 were 2-(2-phenylethyl)chromone derivatives,compounds 22-26 were sesquiterpenes,compounds 27-34 were other type compounds.Compounds 1,2,14-15 and 18-34 were isolated from agarwood originating from A.crassna for the first time.The acetylcholinesterase(AChE)inhibitory activity of the compouds 1,3,4,8,9,11-14,16,17,19,23-25,29 and 32 were tested in vitro by Ellman’s method.The experimental results showed that compounds 1,8,12,13,14,16,24 and 29 exhibited inhibitory activity(IR 15.1±0.4%-46.1±0.8%).And the compounds were measured in vitro by MTT method.Compounds 8 and 19 showed cytotoxic activities towards chronic myelogenous leukemia(K562)with IC50 values of 15.58 and 15.52 μ g/mL,human hepatoma(BEL-7402)with IC50 values of 8.92 and 14.81 μg/mL,as well as human hepatoma human gastric(SGC-7901)with IC50 values of 20.57 and 19.64 μ g/mL,respectively.The antimicrobial activities against Ralstonia solanacearum and Staphylococcus aureus of all the compounds were evaluated by paper disco diffusion method.The results revealed that compounds 16 and 25 displayed positive activities against R.Solanacearum with diameter of inhibition of 14.95±0.10 mm and 12.09±0.12 mm,S.aureus with diameter of inhibition of 12.35±0.11 mm and 16.9±0.09 mm,respectively... |
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