Studies On The Chemical Constituents About Three Plants Of Compositae And One Plant Of Thymelaeaceae

Objective:The first part,Ligularia vellerea(Ligularia genus of Compositae) was used to deal with hepatitis as a folk medicine.For studying the material foundation of Ligularia vellerea,someone had isolated and identified 20 compounds from it.It was reinvestigated for more knowledge.The second part,the plant Ligularia veitchiana grows aside the rivers,hillsides,woods in the elevation.The plant was disributed in the northemwest of Yunnan,Sichun,Guizhou,the west of Hubei,the southernwest of Gansu,the south of Shanxi.It was used to deal with the diseases such as influenza,cough,ulcer and pulmonary tuberculosis as a folk medicine.Up to now,Many eremophilane-type sesquiterpenes were isolated from the plants.We reinvestigated it from Funiu Mountains of Henan Province(the plant of the Mountains was not studied),to plan to isolate different active compounds.The third part,Cacalia ambigua belongs to Cacalia genus(Compositae).The Cacalia genus was distributed in easternnorth of Asia and America.50 species of the genus were grown in China,among them,26 species were used to cure tracheitis,arthritis and cough and so on.We systematically consult the Scifinder data and find no results about the chemical research of Cacalia ambigua.The two genus of Cacalia and Ligularia have kinsfolk relationship on plant taxalogy.Many plants of Cacalia genus have a number of eremophilane-type sesquiterpenoids.To search for the material foundation of this plant and enlarge the knowledge of plant chemotaxology,we studied the chemical constituents.The fourth part,the flowers of Daphne genkwa Sieb.et Zucc. (Thymelaeaceae) were used to detoxify and to release the unneccessary water of body as the common traditional chinese medicine.The quality standard of this medicine has not been worked out.So we studied on the chemical constituents that could be part of study on medicinal quality standard of yuanhua.Methods:We used all kinds of modern chromatographic techniques including silica gel,Sephadex LH-20,MCI gel CHP-40P,Toyopearl HW-40(C) and RP-18 and so on to isolate the chemical constituents of the four plants,and then we identified the compounds and assigned the spectral data of them by modern spectroscopic techniques including ¹H NMR,¹³C NMR,2D NMR and MS.Anticancer activity of several compounds from Ligularia veitchiana were screened by MTT.Results:51 compounds were isolated from these four plants.Among them,27 compounds from Ligularia vellerea were isolated and determined:1, 5-dicaffeoylquinic acid(â… -1),3,5-dicaffeoylquinic acid(â… -2),eremophil-7(11)-en-12, 8α(14β,6α) -dioxide(â… -3),p- hydroxyacetophenone(â… -4),7-hydroxycoumarin(â… -5),3, 4- dihydroxyacetophenone(â… -6),4-methoxy-2',4',3-trihydroxy-chalone (butein-4-methyl ester)(â… -7),2',4',4-trihydroxy-chalone(â… -8),4'-methoxy-7, 3'-dihydroxyflavone(â… -9),4-[(3,4-dihydroxyl)-cinnamyl]-cinnamyl methyl ester(â… -10),p-hydroxycoumaric acid methyl ester(â… -11a),p-hydroxycoumaric acid(â… -11b),2,5-dihydroxyl-6,7-dimethyl-naphthoquinone(â… -12),4-O-caffeoylquinic acid(â… -13),3,4-dihydroxycoumaric acid(â… -14),6,7-dihydroxycoumarin(â… -15), 3-O-caffeoylquinic acid(â… -16),8β-methoxyeremophil-7(11)-en-12,8α(14β,6α) -dioxide(â… -17),furoeremophil-15β,6α-oxide(â… -18),tiglic acid(â… -19),β-sitosterol (â… -20),8β-hydroxyeremophil-7(11)-en-12,8α(14β,6α) -dioxide(â… -21),1-glycerol palmitic acid ester(â… -22),â… -23 Daucosterol(I-23),Palmitic acid(â… -24),1-25 Nonadecanoic acid methyl ester(â… -25),eremophil-7(11),8-dien-12,8α(14β,6α) -dioxide(â… -26). 10 compounds from Ligularia veitchiana were isolated and determined:1,3-dicaffeoylquinic acid(â…¡-1),1,5- dicaffeoylquinic acid(â…¡-2), eremophilan-6-en-11-ol(â…¡-3),β-sitosterol(â…¡-4),eremophil-6α-hydroxy-8α,12-olide (â…¡-5),10β-H-6β,8β-dihydroxyeremophil-8α,12 -oxide(â…¡-6),10α-H-6α, 8α-dihydroxyeremophil-8β,12 -oxide(â…¡-6a),1(10)-en-3-oxoeremophilan-11-ol(â…¡-7), (7α,9α,10α)-9,10-epoxy- eremophilan-11-ol(â…¡-8), 10α,11-endo-peroxide-1(2)-en-7α-hydroeremophilane(â…¡-9).4 compounds from Cacalia ambigua were isolated,ingcluding 2 ent-kaurane-type diterpenes(ent-kaur-16-en-19-oic acid(â…¢-2) and 13,β-kanr-16β-ol (â…¢-3)),β-sitosterol(â…¢-1) and 1 glycerol ester(1-glycerol cerotic acid ester,â…¢-4 ),10 compounds from Daphne genkawa were isolated:daphnoretin(â…£-1),5,7,3', 4'-tetrahydroxyflavonone(â…£-2),5,7,4'-trihydroxyflavonone(â…£-3),5,3', 4'-hydroxyflavonone(â…£-4),4',7-dimethoxy-5-hydroxyflavonone(â…£-5), Octacosane(â…£-6),Dotriacontane(â…£-7),4S,7S-aurantiamide acetate(â…£-8), 7-methoxy-4',5-dihydroxyflavonone(â…£-9),β-sitosterol(â…£-10).Conclusions:Among 27 compounds from Ligularia vellerea,2 of them were new(â… -10 and 12),18 of them were isolated from the plant for the first time.Among 10 compounds from Ligularia veitchiana,4 of them were new(â…¡-3,6a,8,9) and one(â…¡-7) was natural product,others except forâ…¡-4 were isolated from the plant for the first time.4 compounds from Cacalia ambigua were isolated for the first time. Among 10 compounds from Daphne genkawa,2 of them(â…£-6 and 7) were isolated from the plant for the first time.¹H NMR and ¹³C NMR data ofâ…£- 8 were assigned by 2D NMR.The results of the bioactivity test for the several compounds from Ligularia veitchiana showed thatâ…¡-3 can restrain the lung cancer cells(A849)(IC₅₀ value 1.93μg/mL).