Comparative Studies On The Chemical Constituents Of Sophora Tonkinensis And Sophora Flavescens

"Shandougen" and "Kushen" are the commonly used traditional Chinesemedicines derived from Sophora plants. "Shandougen" is the dried roots andrhizomes of Sophora tonkinensis Gapnep. and "Kushen" is the dried roots ofSophora flavescens Ait.. The two crude drugs are so similar in the chemicalconstituents that they were both stated to contain quinolizidine alkaloids,prenylated flavonoids and oleanene triterpenoids. But their clinical applicationsare quite different, "Shandougen" is mainly used to treat acute pharyngolaryngealinfections and sore throat, while "Kushen" is mostly used to treat the skin diseasesand the gynaecological diseases such as eczema, dermatitis and colpitis. In theChinese Pharmacopoeia (CP), the TLC tests given for the identification of"Shandougen" and "Kushen" lack specificity, in which the alkaloids matrine,oxymatrine and sophoridine are chosen as the qualitative markers. And in CP, itseems unsuitable to assess the quality of "Kushen" by determining the content ofthe minor compound matrine, the content of which is much lower than those of theother two active constituents oxymatrine and oxysophocarpine in this drug. Andthe discrepancy between the theory and the practice of traditional Chinesemedicine requires to assess the quality of the crude drugs with multiple indicators. Therefore, in order to specify "Shandougen" from "Kushen" effectively, toassess the quality of these two crude drugs comprehensively, to supply usefulinformation for the further understanding on the relationships between thechemical constituents and the unique medicinal properties claimed for"Shandougen" and "Kushen", and also to search for antiviral agents from naturalproducts as well, the chemical constituents of "Shandougen" and "Kushen" wereinvestigated systemically. Their alkaloid and flavonoid compositions werecompared comprehensively by HPLC fingerprinting, and the contents of severalactive quinolizidine alkaloids in the commercial drugs from different sources weredetermined by HPCE method. In addition, a study on the chemical referencesubstances of Sophora tonkinensis was also carried out. viiPart One: The Chemical Constituents of S. tonkinensis and S. flavescens Ten compounds were isolated from the acid water-soluble part andtwenty-two compounds were isolated from the ether-soluble fraction of the ethanolextracts of the roots and rhizomes of S. tonkinensis, respectively, by repeatedcolumn chromatography and preparative TLC method. The structures of thirtycompounds were elucidated by spectroscopic methods as follows: the alkaloids(+)-matrine (T1), (+)-oxymatrine (T2), (+)-sophoranol (T3), (-)-14β-hydroxymatr-ine (T4), (-)-14β-hydroxyoxymatrine (T5), (-)-sophocarpine (T6),(-)-5α-hydroxysophocarpine (T7), (-)-cytisine (T8), (-)-N-methylcytisine (T9); theflavonoids sophoratonkinochromane A (T10), sophoratonkinochromane B (T11),sophoratonkinochromane C (T12), sophoratonkinochromane D (T13),sophoratonkidochromane B (T14), sophoratonkidochromane A (T15),sophoratonkidochromane C (T16), formononetin (T17), 8-methylretusin (T18),(-)-trifolirhizin (T19); the triterpenoids (+)-lupeol (T20), (+)-sophoradiol (T21);the phenolic components piscidic acid monoethyl ester (T22), maltol (T23),venillic acid (T24), p-hydroxybenzoic acid (T25), docosyl caffeate (T26); the othercompounds physcion (T27), emodin (T28), flemichapparin (T29) and β-sitosterol(30). Among them, T5, T10, T11, T12, T13, T14 and T16 were new compounds,T22, T23, T27 and T28 were isolated from genus Sophora and T17, T18, T24,T25 and T29 were isolated from this species for the first time. Eleven compounds were isolated from the acid water-soluble part andtwenty-two compounds were isolated from the ether-soluble fraction of the ethanolextracts of the roots of S. flavescens, respectively, by repeated columnchromatography a...