Chemical Constituents Of Traditional Chinese Medicine Compound Formula SanZiYangQinTang And Its Single Medicine The Seeds Of Raphanus Sativus L.

The subject mainly studied the chemical constituents of Traditional Chinese Medicine (TCM) compound formulae SanZiYangQinTang, which has been used for expectorant, anti-cough and antiasthmatic purposes, and its single medicine, the seeds of Raphanus sativus L. This subject also reviewed the current investigative methods and developing trends of the fundamental substance of the TCM compound formulae and the advanced studies of TCM compound formulae SanZiYangQinTang and its component medicines.Taken the pharmacological study on the different solvent extracts of the SanZiYangQinTang, the animal pharmacological tests showed the anti-asthmatic and anti-tussive parts are the petroleum ether extract and ethanol extract; however, the expectorant part is the aqueous extract. The quantitative dose-effect relationship study on the anti-asthmatic action of the compound formulae showed its anti-asthmatic effect would be high as the growth of the dose of the seeds of Perilla fruteseens L. britt., which indicated that the seeds of Perilla fruteseens L. britt, is the principal medicine of SanZiYangQinTang regarding to the anti-asthmatic effect.Under the direction of pharmacodynamic results of SanZiYangQinTang, the contents of fatty acids of SanZiYangQinTang and its component medicines were analyzed by GC method. By means of many different chromatographic methods such as silica gel, preparative TLC, Sephadex LH-20, ODS reverse phase chromatographic and HPLC etc., 25 chemical compounds are isolated from its ethanol extract and 24 of them was authenticated by chemical or spectral methods, which are in order raphthioglucoside (1), sinapic acid 5-hydroxymethylfurfural ester(2), 2-(4-hydroxyphenyl) acetonitrile (3), isovanillic acid (4), p-hydroxybenzaldehyde (5), 5-acetoxymethyl furfural (6), 3,4,5-trimethoxycinnamic acid (7), daucosterol (8), rosmarinate methyl ether (9), oxindole-3-acetic acid (10), p-hydroxy beneacetic acid (11), 5-(hydroxymethyl)furano2-carbaldehyde (12), 3,4-dihydroxy benzoic acid (13), 2-hydroxybenzoic acid (14), succinic acid (15), trans-sinapic acid (16), 4-hydroxybenzonic acid (17),β-sitosterol (18), bis(5-formylfurfuryi)ether (19), 5-(butoxymethyl)furan-2-carbaldehyde (20), 2-(4-hydroxyphenyl)acetic acid (21), butyl 2-(4-hydroxyphenyl)acetate (22), (4E)-5-(methylthio)pent-4-enenitrile (23), octacosyl acid (24) respectively. They are all first isolated form SanZiYangQinTang. Among them, compound 1, 2 are determined as new compounds and isolated from the seeds of Raphanus sativus L.; Compounds 4, 6, 7, 10, 13, 14, 15, 20, 21, 22, 24 were first isolated from compound formulae SanZiYangQinTang and its component medicines; 1 and 23 sulfur-containing compounds.The seeds of Raphanus sativus L., belonging to Cruciferous family Raphanus sativus L.(Radish), is one of the component medicines of SanZiYangQinTang. Through all kinds of chromatographic methods, 19 individual compounds have been isolated fromthe EtOH extract of the seeds of Raphanus sativus L.. Among them, 16 compounds have been authenticated by chemical and spectral methods. They are raphthioglucoside (1), (4E)-5-[(6-O-sinapoly)β-D-glucopyranosylsulfanyl]pent-4-enenitrile (2), (4Z)-5-[(6-O-sinapoly)-β-D-glucopyranosylsulfanyl]pent-4-enenitrile (3), (4E)-5-[(6-O-feruloyl)-β-D-glucopyranosylsulfanyi]pent-4-enenitrile (4), (4E)-ethyl 5-(methylsulfinyl)pent-4-enoate (5), 3-(4-hydroxy-3, 5-dimcthoxyphenyl)-8-(hydroxymethyl)-2,7-dioxa-5-thiabicyclo[4,4.0]decan-9,10-diol (6), sinapic acid 5-hydroxymethylfurfural ester (7), (4E)-5-(methylsulfinyl)pent-4-enenitrile (8),β-D-(3,4-disinapoyl)frucofuranosyl-α-D-(6-sinapoyl)glucopyranoside (9),β-D-(3-sinapoyl) frucofuranosyl-α-D-(6-sinapoyl)glucopyranoside (10), 5-[(α-D-galactopyranosyloxy)methyl]-2-furancarboxaldehyde (11), sinapic acid (12), (2E)-methyl 3-(4-hydroxy-3, 5-dimethoxy phenyl)acrylate (13), (2E)-ethyl 3-(4-hydroxy-3,5-dimethoxyphenyl)acrylate (14), (2E)-ethyl 3-(4-hydroxy-3-methoxyphenyl)acrylate (15), 5-(hydroxymethyl)furan-2-carbaldehyde (16) respectively. Among them, compounds 1, 2, 3, 4, 5, 6, 7 were identified as new compounds; Compounds 1, 2, 3, 4, 5, 6, 8 contain sulfur atom, especially, compound 1 is the disulfide bond thioglucoside, 2, 3, 4 are the single sulfur bond thioglucoside, compound 6 is the ring thioglucoside, they are different from traditional thioglucoside; Compounds 5, 8 are the aliphatic and straight-chain sulfur-containing compounds. Compounds 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 13, 14, 15, 16 were first isolated from the seeds ofRaphanus sativus L. We first reported the NMR data of compound 8.To sum up, 35 compounds are isolated from the TCM compound formulae SanZiYangQinTang and its single medicine the seeds of Raphanus sativus L., 7 compounds in which are new compounds, there are 7 sulphur-containing compounds (6 compounds are new) in the compounds that are isolated for the seeds of Raphanus sativus L..With the study on the chemical constitutes of the seeds of Raphanus sativus L., added to the previous researches on the seeds of Perilla fruteseens L. britt and the seeds of Sinapoa alba L., which are all the single medicine of the SanZiYangQinTang, the whole fundamental substance system of this TCM compound formulae is constructed. So we can analyze the composition and origin of the compound formulae fundamental substance and study on each single medicine's contribution to the compound formulae fundamental substance. Combined with the results of the quantitative dose-effect relationship study and the anti-cough effects of individual compounds, the effective substances of SanZiYangQinTang and its single medicines become very clear.To investigate the effective chemical constitutes and their mechanism of action, we make use of the individual compounds which were isolated from SanZiYangQinTang to do the pharmacological test. The pharmacological test in vivo showed that the [2-(4-hydroxy phenyl) acetonitrile] displayed the anti-tussive effect. In the pharmacological test in vitro, the raphthioglucoside has the biological activity in inhibiting the aldose reductase (IC50=14.4μmol/L) and the 5-(butoxymethyl) furan-2-carbaldehyde displays intensive anti-tumor activity.In term of the research on sulfur-containing compounds in which SanZiYangQinTang and the seeds of Raphanus sativus L. adding to the related literatures, an overview was taken on the spectral and structural characteristics, the path of enzymatic hydrolization, the biosynthesis, spectrum characteristics and the biological activity of glucosinolates that are the second metabolites of plants of cruciferous family. What's the most interesting thing were that these natural sulfur-containing compounds that have been isolated from Raphanus sativus L., were quite different with glucosinolates in term of the molecular construction. They are three new kinds of nature thioglusides, especially the disulfide bond thioglucoside raphthioglucoside and the ring thioglucoside were rare in the nature world. It is worth while paying more attention on whether these sulfur-containing compounds occur in the nature or came from the degradation of other glucosinoltes.