Isolation And Identification Of 2-(2-phenylethyl) Chromone Polymers From Agarwood Of Aquilaria Crassna As Well As Their Bioactivities

Agarwood is the resinous heartwood of the plants from Aquilaria or Gyrinops that belongs to the family of Thymelaeaceae.So far,domestic and foreign scholars have done a lot of studies on the agarwood originating from Aquilaria sinensis and Aquilaria malaccensis.But there were few reports for phytochemical study on the agarwood of Aquilaria crassna.In order to discover more 2-(2-phenylrthyl)chromone polymers with novel structure and bioactivities to provide foundation for the development of this genus,we studied on the chemical components and bioactivities of agarwood from A.crassnaTwenty-five compounds were isolated and identified from the agarwood originating from A.crassna by a variety of chromatography technology and spectrum methods(UV,IR,MS,1D and 2D-NMR).Their structures were indentified as: Crassin A(1),Crassin B(2),Crassin C(3),Crassin D(4),Aquilacrassin A(5),Aquilacrassin B(6),Aquilacrassin C(7),Aquilacrassin D(8),Aquilacrassin E(9),Aquilacrassin F(10),Ycrassin A(11),Ycrassin B(12),Ycrassin C(13),Ycrassin D(14),2-(2-phenylethyl)chromone(15),6,8-dihydroxyl-2-[2-(4-methoxyphenyl)ethyl] chromone(16),Rel-(1aR,2R,3R,7bS)-1a,2,3,7b-tetrahydro-2,3-dihydroxy-5-(2-phenylethyl)-7Hoxireno[f][1]benzopyran-7-one(17),Rel-(1aR,2R,3R,7bS)-1a,2,3,7b-tetrahydro-2,3-dihydroxy-[2-(4-methoxyphenyl)ethyl]-7H-oxireno[f][1]benzopyran-7-one(18),Rel-(1aR,2R,3R,7bS)-1a,2,3,7b-tetrahydro-2,3-dihydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-7H-oxireno[f][1]benzo p y r a n-7-o n e(1 9),O x i d o a g a r o c h r o m o n e B(2 0),O x i d o a g a r o c h r o m o n e C(2 1),(5S,6R,7S,8R)-2-[2-(3?-Hydroxy-4?-methoxyphenyl)ethyl]-5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone(22),6,7-cis-Dihydroxy-2-(2-phenylethyl)-5,6,7,8-tetrahydrochromone(23),Tetrahydrochromone E(24)and N-trans-Feruloyltyramine(25).Among all the compounds,compounds 1-4 and compounds 11-14 were new 2-(2-phenylethyl)chromone polymers,compounds 5-10 were new polymers,which were made up by 2-(2-phenylethyl)chromone derivatives and sesquiterpenes,compounds 15-24 were known 2-(2-phenylethyl)chromone derivatives and compound 25 was alkaloids derivative.The acetylcholinesterase(AChE)inhibitory activity of the compouds 1-25 were tested in vitro by Ellman's method.The experimental results showed that compounds 1-6,15,17,20,21,23 and 25 exhibited inhibitory activity(IR 11.1 ± 3.8 % ~ 47.9 ± 0.6%).The cytotoxic activities(K562,SGC-7901 and BEL-7402)of compounds 1-25 were measured in vitro by MTT method,the results showed compounds 5,6 and 9 had significant cytotoxic activities against human gastric cancer cells(SGC-7901)with IC50 values of 29.87,25.67 and 24.79 ?M,respectively.The cytotoxic activities(Hela and A549)of compounds 5-10 were also measured in vitro by MTT method,and compounds 5 and 9 showed cytotoxic activities against human cervical cancer cells(Hela)with IC50 values of 26.72 and 17.57.So far,a significant number of compounds from agarwood have been found and reported by domestic and foreign scholars,which including one hundred and ten 2-(2-phenylethyl)chromone derivatives and one hundred and thirty-six sesquiterpenoids.Only seven bi-2-(2-phenylethyl)chromone derivatives and one dimeric sesquiterpenoid-chromone have been reported until now.Eignt new bi-2-(2-phenylethyl)chromone derivatives and six new dimeric sesquiterpenoid-4H-chromone derivatives were isolated from the agarwood originating from Aquilaria crassna,and this study result has enrich the chemical constituents of agarwood.