Study On Chemical Constituents And Their Bioactivities From Chinese Agarwood Originating From Aquilaria Sinensis In Yunnan Proveince

Agarwood is fragrant resinous heartwood from wounded tree of the Aquilaria and Gyrinops species.In order to enrich chemical structures diversity,the phytochemical investigations on Chinese agarwood from Yunnan Province induced by artificial holing were carried out.Thirty compounds were isolated by various column chromatography.Their structures were indentified by physical,chemical properties and spectral data,and they are selina-3,11-dien-9,15-diol(1),(6,S,7S,8S)-6,7,8-trihydroxyl-2-(4-hydroxyl-3-methoxylphenylethyl)-5,6,7,8-tetrahydro-4H-chromen-4-one(2),(6S,7S,8S)-6,7,8-trihydroxyl-2-(3-hydroxyl-4-methoxylphenylethyl)-5,6,7,8-tetrahydro-4H-chromen-4-one(3),7-hydroxy-2-(4-hydroxy-3-methoxyphenethyl)-6-methoxy-4H-chromen-4-one(4),6-hydroxy-5-methoxy-2-(4-methoxyphenethyl)-4H-chromen-4-one(5),(5a,6?,7?,8?)-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-5,6,7-trihydroxy-5,6,7,8-tetrahydro-8-{6-methoxy-2-[2-(3-methoxy-4-hydroxyphenyl)ethyl]chromonyl-7-oxy}chromone(6),(5a,6?,7?,8?)-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-5,6,7-trihydroxy-5,6,7,8-tetrahydro-8-{6-methoxy-2-[2-(3-hydroxy-4-methoxy phenyl)ethyl]chromonyl-7-oxy}chromone(7),(5?,6?,7?,8?)-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]·5,6,7-trihydroxy-5,6,7,8-tetrahydro-8-{6-hydroxy-2-[2-(3?hydroxy-4-methoxyphenyl)ethyl]chromonyl-7-oxy}chromone(8),(5?,6?,7?,8?)-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-5,6,7-trihydroxy-5,6,7,8-tetrahydro-8-{6-methoxy-2-[2-(4-methoxyphenyl)ethyl]chromonyl-7-oxy}chromone(9),(5?,6?,7?,8?)-2-[2-(4-methoxyphenyl)ethyl]-5,6,7-trihydroxy-5,6,7,8-tetrahydro-8-{6-metho xy-2-[2-(3-methoxy-4-hydroxyphenyl)ethyl]chromonyl-7-oxy} chromone(10),(5 a,6?,7?,8?)-2-[2·(3-hydroxy-4-methoxyphenyl)ethyl]-5,6,7-trihydroxy-5,6,7,8?tetrahydro-8-{6-methoxy-2-[2-(3-methoxy-4-hydroxyphenyl)ethyl]chromonyl-7-oxy}chromone(11),(5?,6?,7?,8?)-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-5,6,7-trihydroxy-5,6,7,8-tetrahydro-8-{6-methoxy-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]chromonyl-7-oxy}chromone(12),(5?,6?,7a,8?)-2-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-5,6,7-trihydroxy-5,6,7,8-tetrahydro-8-{6-methoxy-2-[2-(4-hydroxy-3-methoxy phenyl)ethyl]chromonyl-7-oxy} chromone(13),(5?,6?,7?,8?)-2-[2-(4-methoxy phenyl)ethyl]-5,6,7-trihydroxy-5,6,7,8-tetrahydro-8-{6-methoxy-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]chromonyl-7-oxy}chromone(14),(5?,6?,7a,8?)-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-5,6,7-trihydroxy-5,6,7,8-tetrahydro-8-{6-methoxy-2-[2-phenylethyl]chromonyl-7-oxy}chromone(15),(5?,6?,7?,8?)-2-(2-phenylethyl)-5,6,7-trihydroxy-5,6,7,8-tetrahydro-8-{2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]chromonyl-6-oxy}chromone(16),(5?,6?,7?,8?)-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-5,6,7-trihydroxy-5,6,7,8-tetrahydro-5-{6-methoxy-2-[2-(3-methoxy-4-hydroxy phenyl)ethyl]chromonyl-7-oxy}chromone(17),sindichromone M(18),6,7-dimethoxy-2-(4-methoxyphenethyl)-4H-chromen-4-one(19),5?,6?,7?,8?-tetrahydroxy-2-[2-(2-hydroxyphenyl)ethyl]-5,6,7,8-tetrahydrochromone(20),aquilarone D(21),isoagarotetrol(22),6-methoxy-2-(2-phenylethyl)chromone(23),syringin(24),(?)syringaresinol(25),3-phenyl-3-hydroxy-methylpropanoate(26),3-(4-methoxyphenyl)-3-hydroxy-methylpropanoate(27),(Z)-p-coumarate(28),4'-methoxycinnamic acid(29)and isozingerone(30).Among the thirty compounds,one compound was sesquiterpenoid,nine compounds were 2-(2-phenylethyl)chromones,thirteen compounds were bi-phenyl-ethylchromones,and seven compounds were other type.Among them,there are eighteen new compounds including a new sesquiterpene(1),four compounds were new 2-(2-phenylethyl)chromone derivatives(2-5)and thirteen were new bi-phenylethylchromones(6-18).The cytotoxicities against SCG-7901,BEL-7402 and A549 were evaluated in vitro using the MTT method.The results indicated that compounds 19 and 28 showed weak cytotoxicities.The acetylcholinesterase(AChE)inhibitory activity was tested by Ellman's method.The results indicated that eight compounds including compounds 2,3,4,16,19,22,25 and 29 exhibited inhibitory activity.