Study On The Chemical Constituents And Biological Activities Of Two Medicinal Plants From Ainsliaea Genus

The genus Ainsliaea belongs to the Compositae family.There are more than 70 species of the genus Ainsliaea distributed in the world,and 50 species in China,which mainly distributed in the Southeast of P.R.China.Many Ainsliaea species are used as traditional folk medicines for the treatment of many diseases in clinic.In order to determinate the relationship between the chemical constituents and thier bioactivities,two herbs of A.fragrans and A.heterantha were selected for phytochemical and pharmacological studies.As a result,73 compouds including 9 new ones,were isolated by various chromatographic methods and their structures were elucidated through spectroscopic methods.Some isolates exhibited cytotoxic and anti-inflammatory acivites.A series of chromatographic techniques were used to isolate 35 compounds from the whole plants of A.fragrans.Combined with spectroscopic techniques,their structures were identified,including 17 sesquiterpenes and their oligomers,10 caffeoylquinic acids,5 flavonoids and 3 other types of compounds.They are ainsfragolide(1),ainsliatrimer A(2),ainsliatrimer B(3),ainsliatriolide A(4),gochnatiolide E(5),gochnatiolide F(6),gochnatiolide G(7),gochnatiolide H(8),ainsliadimer A(9),ainsliadimer B(10),gochnatiolide A(11),gochnatiolide B(12),gochnatiolide C(13),ainsliadimer E(14),macrocliniside J(15),macrocliniside B(16),macrocliniside I(17),trans-p-hydroxycinnamic acid(18),caffeic acid(19),chlorogenic acid(20),isochlorogenic acid C(21),methyl 4,5-caffeoylquinic acid(22),isochlorogenic acid A(23),macranthoin G(24),isochlorogenic acid B(25),macranthoin F(26),cynarin(27),taxifolin(28),luteolin(29),apigenin(30),astragalin(31),cimifugin(32),p-hydroxybenzoic acid(33),piceol(34)and picein(35).Of the six new compounds reported herein,ainsfragolide(1)is a rare guaianolide trimer generated through a novel C2’-C15" linkage,and gochnatiolide E(2)represent the first reported example of an OH-13 substituted guaianolide dimer.Eleven compounds 1,5～8,15,18,22,28,32 and 33 were isolated from the genus Ainsliaea for the first time,and twenty-two compounds 1～3,5～9,13～19,22,26,28 and 32～35 were firstly reported from this plant.Compounds 1,2,3 and 11 exhibited stronger inhibitory activities against five cancer cell lines(Huhl,LM3,C6,PANC-1 and Hela).The main component in A.fragrans,isochlorogenic acid C(21)had a protective effect on DSS-induced ulcerative colitis(UC)in mice.38 compounds were isolated from the whole plants of A.heterantha by various column chromatographies,including 19 sesquiterpenes and 19 other types.They are 4β,15dihydroainsliaolide A(36),4β,15-dihydrodiaspanolide A(37),diaspanolide A(38),diaspanolide E(39),ainsliaolide A(40),diaspanolide B(41),vernoflexin(42),mokko lactone(43),11α,13dihydrodehydrocostuslactone(44),dehydrocostus lactone(45),11β,13-dihydrodesacylcynaropicrin(46),radicol(47),10β-hydroxyisodauc-6-en-14-al(48),spathulenol(49),1β,9βdihydroxy-α-cyclocostunolide(50),9β-hydroxyreynosin(51),10-hydroxyl-15-oxo-α-cadinol(52),haageanolide(53),germacra-1(10),4,11(13)-triene-12,8α-olide-15-acid(54),phytol(55),tricin(56),quercetin(57),magnolol(58),hydroquinone(59),salicylic acid(60),gallic acid(61),ethylparaben(62),ethyl caffeate(63),E-5-ethoxycarbonyl-4-pentenoic acid(64),dibutyl phthalate(65),13(S)-HOTrE(66),linoleic acid(67),methyl linoleate(68),linolenic acid(69),methyl linolenate(70),1-monolinolein(71),1-linolenoylglycerol(72)and β-stigmasterol(73).Among them,36,37 and 50 were new compounds,36、37、42、47、49～51、53、54、58～61、64～68 and 70 were isolated from the genus Ainsliaea for the first time.All isolates were firstly reported from this plant.Compounds 50 and 54 showed nitric oxide(NO)inhibitory effects in LPS-induced RAW 264.7 macrophage cells,respectively.