Study On Chemical Constituents Of The Extract Of Chloroform From Leaves Of Cyclocarya Paliurus (Batal.) Iljinsk

Cyclocarya Paliurus (Batal.) Iljinsk (Juglandaceae) is the only one plant of Cyclocaryaceae family, which is distributed mainly in the south of China. In the south of China, its leaves are used as folk medicine for treatment of diabetes, coronary heart disease, neurasthenia and hypertension. Cyclocarya Paliurus (Batal.) Iljinsk, as a rich resource in China, has very high value to be exploited. In our previous research, the result of pharmaceutical experiment showed that the chloroform part of the 75% EtOH extracts from the plant has activity to keep low blood pressure, which led us to do further research on Cyclocarya Paliurus (Batal.) Iljinsk.In the first part of this dissertation, it is a review that describes the recent studies on chemical constituents and pharmacology activities of Cyclocarya Paliurus (Batal.) Iljinsk. The chemical constituents of the leaves from the plant's chloroform extract were studied in the following parts.The extracts of chloroform part were subjected to column chromatograph on silica gel to give five parts Fr.1, Fr.2, Fr.3, Fr.4 and Fr.5. Then they were purified mainly by column chromatograph on silica gel, preparing TLC, Sephadex LH-20 and semi-preparing HPLC, recrystallization, respectively. At last, twenty-one compounds were got, and their purity was checked by melting point, TLC and HPLC. Compound IX, XVII and XX were subjected to column chromatograph on silica gel, and preparative TLC, recrystallization from Fr.1. CompoundⅡ,Ⅶ, X, XI, XII and XVIII were separated by column chromatograph of silica gel, and recrystallization from Fr.2. The isolation of Fr.3 was to afford compoundⅠ, XIV and XVI by column chromatograph of silica gel and Sephadex LH-20, and recrystallization. Continuing studies of Fr.4 have led to the isolation of compoundⅢ,Ⅳ,Ⅴ,Ⅵ, XIII, XV, XIX and XXI by column chromatograph of silica gel, and recrystallization. CompoundⅧwas separated by column chromatograph of silica gel, and recrystallization from Fr.5.The structures of Kaempferol (V), 4′-methoxy-7-hygroxyl-isoflavnone(VI),β- Sitosterol (VII), 3β,20-dihydroxyl-5β-Pregnanes (VIII), Hentriacontane (X) and Behenic acids (XI) were identified by 1H NMR, 13C NMR data and comparison with the references. The structures of pterolactone (I) and 3,6,3′,5′-tetramethox-5,7,4′-trihy- droxy-flavonol (IV) were elucidated by 1H NMR, 13C NMR, HSQC , HMBC data and comparison with the references. Six pentacyclic triterpeniods, Olean-12-en-28-oic acid (XIV),β-boswellic (XV),α-boswellic (XVI),β-amyrin (XVII),β-amyrone (XVIII) and 3β-O-trans-caffeoyl-morolic acid (XIX), were established by MS, 1H NMR, 13C NMR, DEPT data and comparison with the references. Compound II was determined by IR, MS, 1H NMR, 13C NMR, HSQC, HMBC data and chemical methods, they are 3-methoxy-pterolactone and 3β-O-trans-caffeoyl-morolic acid (XIX). Compound II and XIX were identified as new compounds by searching of SciFinder Scholar, their pharmacology activities need further experiment to be checked. Pterolactone, 3,6,3′,5′-tetramethox-5,7,4′-trihydroxyflavonol, 4′-methoxy-7- hygroxy-l-isoflavnone, 3β,20-dihydroxyl-5β-Pregnanes, Hentriacontane,β-boswell- ic,α-boswellic,β-amyrin,β-amyrone and 4- hygroxyl-3-methoxy-benzoic acid are isolated from the plant for the first time.