Chemical Constituents Of Siraitia Grosvenorii (Swingle) C. Jeffrey

Siraitia grosvenorii (Swingle) C. Jeffrey,a member of Cucurbitaceac, mainly distributing in Guangxi, Guangdong, Hunan and Jiangxi province in China, is used as Chinese folk medicine to ease pain, relieve cough, detoxifcation and so on for 200 years. It was reported that roots, leaves and fruit Siraitia grosvenorii (Swingle) C. Jeffrey can be used for treating diseases of systems of breath and digest. In order to deeply investigate the chemical constituents, the fruit of Siraitia grosvenorii (Swingle) C. Jeffrey were extracted, separated, and the structures of the chemical constituents were identified in this dissertation.The dissertation mainly composes of two parts. The first part is a review of the research of Siraitia grosvenorii(Swingle) C. Jeffrey, which mainly included its chemical constituents and pharmacology activities.The second part is about experiment on the isolation and elucidation the structures of chemical constituents of the Siraitia grosvenorii (Swingle) C. Jeffrey. Phytochemical investigation of the fruit of Siraitia grosvenorii (Swingle) C. Jeffrey has resulted in the isolation of twenty-six compounds, which structures were elucidated on the basis of spectroscopic analysis, especially NMR, and chemical reactions.The fruit of Siraitia grosvenorii (Swingle) C. Jeffrey was extracted by 75% ethanol, and then partitioned by petrol ether, chloroform, ethyl acetate and n-butanol, respectively. The petrol ether extract was isolated on column chromatograph of silica gel with petrol ether and ethyl acetate (0:100→100:0) as elution to give five parts (P-Fr.Ⅰ, P-Fr.Ⅱ, P-Fr.Ⅲ, P-Fr.Ⅳand P-Fr.Ⅴ). Compound 3, 7, 11, 12, 18, 19, 20 and 21 were got from P-Fr.Ⅰand P-Fr.Ⅱby column chromatograph of silica gel with petrol ether and ethyl acetate as elution, PTLC, recrystallization. The chloroform extract was separated by column chromatograph of silica gel with chloroform and methyl alcohol (0:100→100:0) as elution to give five parts (C-Fr.Ⅰ, C-Fr.Ⅱ, C-Fr.Ⅲ, C-Fr.Ⅳand C-Fr.Ⅴ). Continuing studies of C-Fr. C-Fr.Ⅰhave led to compound 8 and 10 by PTLC and column chromatograph of Sephadex LH-20. Compound 9 was obtained only by recrystallization from C-Fr.Ⅱ. Through silica gel column chromatograph, large amount of compound 13 was acquired from C-Fr.Ⅲ. Compound 15 was gained on the basis of column chromatograph of silica gel, recrystallization from C-Fr.Ⅳ. The ethyl acetate extract was subject to column chromatograph of silica gel with chloroform and methyl alcohol (0:100→50:50) as elution to give five parts (E-Fr.Ⅰ, E-Fr.Ⅱ, E-Fr.Ⅲ, E-Fr.Ⅳand E-Fr.Ⅴ). The isolation of E-Fr.Ⅰand E-Fr.Ⅱwas to afford compound 4, 5, 9, 10, 17 and 24 by column chromatograph of silica gel, PTLC and recrystallization. Compound 2, 6 and 17 were got from E-Fr.Ⅲand E-Fr.Ⅳby column chromatograph of silica gel and Sephadex LH-20. The separation of n-butanol extract was to afford compound 2, 16, 22, 23, 25 and 26 by column chromatography of silica gel, Sephadex LH-20, C18 and PTLC.On the basis of spectroscopic analysis and by comparison with the references, the structures of twenty compounds were identified, they are Perlolyrine (1), Flazine (2), 1-acetyl-β-Carboline (3), Cyclo-(Leu-Pro) (4), Cyclo-(Ala-Pro) (5), Cyclo-(Leu-Ile) (6), Cyclo-(Ile-Val) (7), Magnolol (8), Glycosmisic acid (9), Kaempferol-7-O-α-L-rhamnopyranoside (10), Kaempferol-3,7-O-α-L-rhamnopyranoside (11), Mogroester (12),β-sitosterol (13), Dauosterol (14), 5-oxymaltol (15), Vanillic acid (16), Bis-(5-formyl-furfuryl) ther (17), 5-hydroxymethyl furoic acid (18), Succinic acid (19), L-pyroglutamic acid (20), of which compound 1, 2, 4, 9 were mainly identified by UV, IR, 1H NMR, 13C NMR, 1H-1H COSY, HSQC and HMBC; compound 3, 15 were identified by MS, IR, 1H NMR and 13C NMR; others were mainly identified by 1H NMR and 13C NMR. There are still another six compounds need further spectroscopic data, such as MS, 1H-1H COSY, HSQC and so on, to determine their structures. All identified compounds, except compound 11, 12 and 13, were isolated from the plant for the first time.