Studies On Chemical Constituents And Biological Activities Of Dodonaea Viscosa And Three Euphorbiaceous Medicinal Plants

Dodonaea viscosa is a species of genus Dodonaea of family Sapindaceae. In mainland China, there is only one species, D. viscosa, belonging to genus Dodonaea. The leaves and roots of this plant have been used as folk medicine. The medicinal plant located in India and Mexico was investigated more, but less in China. Flavonoids and clerodane-type diterpenoids were isolated from D. viscosa previously, and some compounds had antitumor and antibacterial activities. Macaranga denticulata, Glochidion puberum, and Jatropha curcas are three species of family Euphorbiaceae. The barks and roots of M. denticulata have been used as folk medicine. Up to now, only a paper reported5compounds from this plant and their antioxidant activities. The roots, stems, leaves and fruits of G puberum have been used as folk medicine. Bisabolane-type sesquiterpenoids and triterpenoids were isolated from this medicinal plant, but their biological activities were not screened. The barks and leaves of J. curcas have been used as folk medicine. Jatrophone-type diterpenoids and cytotoxicities of J. curcas have been found, and several compounds with novel skeletons were isolated from J. curcas recently. Four medicinal plants are rich in dry and hot valley in Yunnan Province, and their chemical constituents are abundant. It is significant for the discovery of lead compounds.Adipose tissue, being composed of adipocytes that store energy in the form of triglycerides, is important for the regulation of energy balance. Adipocytes have been regarded as a potential target for obesity and type-2diabetes. Investigation of active natural products to effect on adipocyte differentiation has important significance for new generation of anti-diabetic drug. To study on the active natural products and promote development and utilization of medicinal plants located dry and hot valley of Yuan river in Yunnan Province, the chemical constituents of Dodonaea viscosa, Macaranga denticulata, Glochidion puberum, and Jatropha curcas were investigated, and some compounds were screened to effect on adipocyte differentiation.1.35compounds were isolated and identified from the aerial parts of D. viscosa, including10new isoprenylated flavonoids, named dodoviscins A-J(â… -1-â… -10), and7new diterpenoids, named viscoterpenes A-G (â… -11-â… -17). Viscoterpene A (â… -11) is a diterpenoid possessing a novel bicyclo[6,2,0]decane skeleton, which structure was confirmed by X-ray diffraction analysis. The plausible biogenetic pathway for â… -11 was proposed. Viscoterpenes B-D (I-12-I-14) are three cyclopropane clerodane-type deterpenoids possessing a tricyclo[5,4,0,01,3]undecane skeleton, which were only isolated from this plant. Viscoterpene E (â… -15) is a5,10-secoclerodane diterpenoid. Viscoterpene F (â… -16) is a5(4â†'19)-abeo-clerodane diterpenoid. Viscoterpene G (â… -17) is a clerodane diterpenoid. The plausible biogenetic relationship for five types of diterpenoids was presumed.Additionally, the known compounds â… -18,â… -23, â… -27-â… -29,â… -31,â… -33, and â… -35were isolated from this plant for the first time.Compounds â… -1,â… -2,â… -4,â… -5,â… -7-â… -9,â… -18-â… -20,â… -26, and â… -27promoted adipocyte differentiation as characterized by increased triglyceride levels in3T3L1cells. Compounds â… -1,â… -20, and â… -27also significantly enhanced the accumulation of lipid droplets and induced up-regulation of the expression of adipocyte-specific genes, aP2and GLUT4. The adipogenesis-promoting activities of the known compounds â… -18-â… -20and â… -27had not been reported previously.2.20compounds were isolated and identified from the twigs and leaves of M. denticulata, including7new isoprenylated chalcones, named denticins A-G (â…¡-1-â…¡-7). Denticin A (â…¡-1) is a novel isoprenylated chalcone dimer. Two chalcone units was connected by C-8’-C-3’"and C-4’-O-C-4’" bonds. A biogenetic pathway was proposed for Denticin A. Denticins B and C (â…¡-2and â…¡-3) are two2’-oxygated isoprenylated dihydrochalcone. The known compounds â…¡-8-â…¡-11and â…¡-13-II-20were isolated from this plant for the first time.Compounds â…¡-8,â…¡-13and â…¡-14promoted adipocyte differentiation as characterized by increased triglyceride levels and enhanced the accumulation of lipid droplets in3T3L1cells. The adipogenesis-promoting activities of three compounds had not been reported previously.3.33compounds were isolated and identified from the twigs of G puberum, including1new highly oxygenated bisabolane-type sesquiterpenoid, named glochipuberin A (â…¢-1).32known compounds belong to1bisabolane-type sesquiterpenoid (â…¢-2),6oleanane-type triterpenoids (â…¢-3-â…¢-8),5lupane-type triterpenoids (â…¢-9-â…¢-13),4steroids (â…¢-14-â…¢-17),6lignins (â…¢-18-â…¢-23),6flavonoids (â…¢-24-â…¢-29), and4phenolic acid compounds (â…¢-30-â…¢-33). The known compounds â…¢-2-â…¢-10, â…¢-14-â…¢-17, and â…¢-19-â…¢-33were isolated from this plant for the first time.4.9known compounds were isolated and identified from the twigs and leaves of J. curcas, which were identified as3β,12-dihydroxy-13-methylpodocarpane-8,10,13-triene (â…£-1), gossweilone (â…£-2),1,2-dihydroheudelotinol (â…£-3), castanopsol (â…£-4), cerevisterol (â…£-5), ergosta-6,22-dien-3p,5a,8α-triol (â…£-6), dimeric coniferyl acetate (â…£-7), fraxinol (â…£-8), and (3R,4R)-(-)-4-hydroxymellein (â…£-9). Compounds IV-3-IV-9were isolated from this plant for the first time.95compounds (including flavonoids, sesquiterpenoids, diterpenoids, triterpenoids, lignans, and so on) were isolated from four medicinal plants, including25new compounds, which belong to17isoprenylated flavonoids,7diterpenoids (including1diterpenoid with the novel skeleton), and1highly oxygenated bisabolane-type sesquiterpenoid. The biological results showed that15flavonoids promoted adipocyte differentiation as characterized by increased triglyceride levels in3T3L1cells. Among them,3compounds also induced up-regulation of the expression of adipocyte-specific genes, aP2and GLUT4. The study results are significant for the discovery of lead compounds for antidiabetic and for development and utilization of four medicinal plants.In the end, it was reviewed that new isoprenylated flavonoids from plants and their biological activities were reported in nearly5years.