Phytochemical Investigations On The Crude And Processed Epimedium Koreanum

This thesis is composed of four chapters.The first chapter is a review about the recent progress on the chemical constituents,pharmacological ativities and processing of the genes Epimedium.The second and the third chapters described the phytochemical investigation on n-BuOH extract of processed E.koreanum and the EtOAc extract of crude E.koreanum,respectively.The last chapter,conclusion of this dissertation was made.The genus Epimedium(Berberidaceae),is a genus of about 52 species,which mianly distributed in the temperate and subtropics of Mideast,Asia and Europe.China is the distributin center of the genus Epimedium,and it possess 43 species and 4 variety species.Extracts of the aerial parts of this genus are used in a famous botanical supplement that has been widely used as a tonic,aphrodisiac and antirheumatic in China for more than 2000 years.Researches of pharmacology activities proved that Epimedium including anti-osteoporosis,anti-inflammatory,anti-aging,anti-oxidation,anti-tumor,strengthen immunity and estrogenic/antiestrogenic activities.However,the pharmacologic activities were different between crued and processed products.The crued product is mainly used for rheumatism and strong bones,while,the processed product has nourishing kidney,enhancing yang and anti-inflammatory effect.The reason was that the chemical constituents changed during processing.In 2009,the systematical chemical investigation of Epimedium brevicornum by our group led to the discovery of a new prenylflavonol,2"-hydroxy-3"-en-anhydroicaritin,which can significantly decreased TNF-? and increased IL-10 levels.Subsequently,we obtained configuration changed prenylflavonols and their glycosides from the EtOAc extract of the processed E.koreanum.In order to further elucidate the difference of chemical consitituents between the crude and processed products of the genus Epimedium,a systematical phytochemical study on the n-BuOH extract of processed E.koreanum and the EtOAc extract of crued E.koreanum was carried out.By all kinds of chromatographic materials,twenty-four flavonoid glycosides were isolated from the n-BuOH extract of processed E.koreanum,including three new prenylflavonol glycosides,epimedkoreside A-C(1-3).The known compounds were identified as acuminatoside(4),icarisoside B(5),icariin(6),epimedin A(7),epimedin B(8),epimedin C(9),epimedoside A(10),desmethylicaritin 3-0-?-D-fucopyranosyl(1?2)-a-L-rhamnopyranoside-7-O-?-D-glucopyraoside(11),baohuoside V(12),diphylloside B(13),diphylloside A(14),epimedoside E(15),anhydroicaritin 3-O-?-D-fucopyranosyl(1?2)-?-L-rhamnopyranoside-7-O-?-D-glucopyraoside(16),Hexandraside E(17),4',5-dihydroxyl-8-(3,3-dimethylallyl)-flavonol-3-0-[-?-D-xylopyranosyl(1?3)-a-L-rhamnopyranozside]-7-O-?-D-glucopyranoside(18),diosmetin 7-O-?-D-glucuronide(19),apigenin-7-O-?-D-glucuronide(20),rutin(21),3',5,7-trihydroxy-4'-methoxyflavone-3-O-?-D rhamnopyranosyl(1?6)-?-D-glucopyranoside(22),kaempferol-3-O-?-L-rhamnopyranosyl-(1?6)-?-D-glucopyranoside(23),and quercetin-3-O-?-D-galactopyranosyl-7-O-?-D-glucopyranoside(24)?Carefully investigation on the EtOAc extract of the crude E.koreanumled to the isolation of sixteen flavonol glycosides,including a new acylated prenylflavonol glycoside,Anhydroicaritin-3-O-?-D-(2,6-0-acetyl)glucopyraosly(1?3)-?-L-(4-0-acetyl)rhamnopyranoside(1*).The known compounds were identified as,apigenin 7-O-?-D-glupyranoside(2),icariin II(3),icariin(4),sagittasine A(5),2"-O-rhamnosyl icarisoside II(6),3"'-carbonyl-2"-?-L-quinovosyl icariside II(7),epimedoside(8),icarisoside A(9),quercetin-3-O-?-D-galactopyranoside(10),epimedoside C(11),epimedin B(12),sagittatoside B(13),anhydroicaritin-3-0-?-D-fucopyranosyl(1?2)-a-L-rhamnopyranoside(14),epimedokoreanosid II(15),hexandraside E(16).The results show that there was little change of prenylflavonoids isolated from n-BuOH extract of processed E.koreanum compared with those of the crude product.Chemical compositions are significantly differenct between the crude and processed EtOAc extract of E.koreanum,and we had not found any prenylflavonoid or its glycoside with construct changed prenyl group.Changes in the material basis of the processing,pharmaceutical performance of Epimedium differences may be the reason.