Studies On The Sesquiterpenes From Caragana Intermedia Kuang Et H.C.FU And Their Activities

Caragana intermedia Kuang et H. C. Fu is a shrub widely distributed in desert area ofnorthwest part of China. Local people used its roots, blossom and stems as agents forthe symptoms of menstrual disorder; fatigue and asthenia. Recently, our research resultsshow that the raw extract of the material possess anti-tumor activities to inhibit cervicalcancer and breast cancer in vitro. In the screen of anti-HIV, we found that chloroformand low polar fraction of ethyl acetate extract had weak anti-HIV bioactivity. In presentwork, the chemical investigation of the chloroform extract of its aerial part led to afford12 sesquiterpenes including in nine eudesmane-and three aromadendrane-type ones:Eudesma-4(15)-ene-1β,7α-diol (1), Eudesma-4(15)-ene-1β,7β-diol (2), Eudesma-4(15)-ene-1β,8α-diol (3), Trinoreudesma-4(15),8-diene-1β-ol-7-one (4), Eudesma-4(15),7-diene-1β-ol (5), 5-epi-Eudesma -4(15)-ene-1β,6β-diol (6), Eudesma-4(15)-ene-1β,6α-diol (7), Eudesma-4(15)-ene-1β,5α-diol (8), trans-Octahydroindane-2β-isopropyl-4-methylene-8β-methyl-7β-ol (9), and allo-aromadendrane-3α,9α-diol (10), (+)-3α,9β-aromadendranediol (11), (+)-Spathulenol (12) with a ligand (+)-lariciresinol (19).Meanwhile, we collected 3.2g compound 8 for further mice activity test because beforethis our group found the compound shown lowering blood glucose in extensive screen,and prepared compound 13, 14, 15, 16, 17, 18 from compound 12 and 8 for relevantactivity. Compound 1, 2, 3, 4, 5, 9 are novel chemicals, especutially a structure ofcompound 9 is a new skeleton carbon in noreudesmane-type sesquiterpene. Compound8 showed glucose consumption of C2Cl2 muscle cell with IC value of 10.7μg/ml andglucose consumption in db/db mice with IC value of 100mg/kg resulting in same effectof Metformin in vivo. Compound 6 discolsed weak anti-HIV activity with a value of10μg/ml in the MT-2 cell infected HIV-ШB virus. Compound 1, 2, 3, 8, 9, 10, 11, 12,13, showed anti-Pyricularia oryzae P-2b activity with IC value of 12μg/ml, 16μg/ml,38μg/ml, 20μg/ml, 10μg/ml, 25μg/ml, 18μg/ml, 9μg/ml, 35μg/ml respectively. Thestructures of these compounds were determined by spectral data including 1D, 2DNMR, HRMS and IR spectra. Compound 1, 6, 7, 8, 11 was confirmed by X-raycrystallographyic analysis.