Study On Anti-diabetic Chemical Constituents Of Curcuma Wenyujin And Eupatorium Chinense

This study aim to find out the anti-diabetes chemical constituents of Curcuma wenyujin and Eupatorium chinense.Thirty four terpenoids,including two new cadinane-type sesquiterpenoids with conjugated aromatic-ketone structures,curcujinone A(1)and curcujinone B(2),and thirty two known compounds curcumol(3),curcumenol(4),7?,11?-epoxy-5?-hydroxy-9-guaiaen-8-one(5),zedoarondiol(6),1 S,4S,5S,10R-isozedoarondiol(7),procurcumadiol(8),phaeocaulisin E(9),12-hydroxycurcumenol(10),6-guaiene-4?,10?-diol(11),procurcumenol(12),4,10-epizedoarondiol(13),zedoarolide B(14),zedoalactone A(15),trans,trans-germacrone(16),curdione(17),1S,10S,4S,5S-germacrone(18),13-hydroxygermacrone(19),zederone(20),furanodienone(21),1(10)Z,4Z-furanodiene-6-one(22),curdionolide A(23),curcumalactone(24),curcumanolide A(25),curcumanolide B(26),gajutsulactone B(27),gajutsulactone A(28),curcuzedoalide(29),wenyujinin C(30),curzerenone(31),cyperusol C(32),(1R,2S,4S,5R)-angelicoidenol-2-O-?-D-glucopyranoside(33),amoxanthin A(34)were isolated from 95%ethanol extract of the root tubers of Curcuma wenyujin.Twenty benzofuran compounds,including ten new benzofuran compounds dieupachinin G(35),dieupachinin H(36),dieupachinin I(37),dieupachinin J(38),dieupachinin K(39),1-(6-hydroxy-2-(1-hydroxyethyl)benzofuran-5-yl)ethenone(40),8-acetyl-7-hydroxy-4-methyldibenzo[b,d]furan-2-carboxylic acid(41),1-(3,6-dihydroxy-3-methyl-2,3,3a,8b-tetrahydrofuro[3,2-b]benzofuran-7-yl)ethenone(42),8-acetyl-4,7-dihydroxy-1,4-dimethyl-1,2,3,4-tetrahydro-4a,9b-epoxydibenzo[b,d]furan-1-carboxylic acid(43),4-(acetoxymethyl)-8-acetyl-4,7-dihydroxy-1-methyl-1,2,3,4-tetrahydrodibenzo[b,d]furan-1-carboxylic acid(44),and ten known benzofuran compounds euparin(45),2,5-diacetyl-6-hydroxy-henzofuran(46),ruscodibenzofuran(47),(2R,3S)-3-ethoxy-2,3-dihydro-6-hydroxy-2-(1-methylethenyl)-5-benzofuranyl(48),6-hydroxy-3?-methoxytrematone(49),2',4'-dihydroxy-5'-(3-methyl-3-buten-l-yl)acetophenon(50),12,13-dihydroxyeuparin(51),3 a-tiglinoyfoxy-2,3-dihydroeupar(52),ethanone(53),gymnastone(54)were isolated from 95%ethanol extract of the Eupatorium chinense.Their structures were determined by spectroscopic methods,especially 2D NMR and HRMS techniques.The relative and absolute configurations of the new compounds were determined with the help of quantum chemical DFT and TDDFT calculations of the 13C NMR chemical shifts,ECD spectra,and specific optical rotations.All compounds were evaluated for their anti-diabetic activities with a glucose consumption model on HepG2 Cells and a glucose transportation model on C2C12 Cells.Among these compounds,curcumenol(4),7 a,11 ?-epoxy-5?-hydroxy-9-guaiaen-8-one(5),curdione(17),(1S,4S,5S,10S)-germacrone(18),zederone(20),a mixture of curcumanolide A(25)and curcumanolide B(26),gajutsulactone B(27),and wenyujinin C(30)showed promising activities with over 45%increasing of glucose consumption at 10 ?M.dieupachinin G(35),dieupachinin H(36),dieupachinin J(38),dieupachinin K(39),8-acetyl-7-hydroxy-4-methyldibenzo[b,d]furan-2-carboxylic acid(41),8-acetyl-4,7-dihydroxy-1,4-dimethyl-1,2,3,4-tetrahydro-4a,9b-epoxydibenzo[b,d]furan-1-carboxylic acid(43)showed promising activities with over 20%increasing of glucose transportation at 10 ?M.