Extracts of fruits and leaves of Connarus paniculatus afford six quinolizidine alkaloids which were identified as piptanthine, 18-epipiptanthine, ormosanine, homoormosanine, podopetaline (monohydrochloride) and homopodopetaline on the basis of high-field NMR studies. 1D and 2D NMR experiments provide complete assignments of the (1)H and (13)C spectra. In conjunction with detection of nuclear Overhauser effects (NOESY), these results allow detailed structure characterization including determination of relative configurations for the chiral sites and conformational analysis. Exchange phenomena involving nitrogen inversion were detected.
"In the family Connaraceae, only six genera (Agelaea, Byrsocarpus, Cnestis, Connarus, Rourea, and Roureopsis) have been investigated for chemical composition and the major components have been quinolizidine alkaloids (Le et al., 2005), quinones (Aiyar et al., 1965; Ramiah et al., 1976a), triterpenes, coumarins, and flavonoids. Triterpenes have been found only in the genus Rourea (Zhang et al., 2008), coumarins in Byrsocarpus (Vickery & Vickery, 1980) and flavonoids in Agelaea (Kuwabara et al., 2003), Byrsocarpus (Ahmadu et al., 2007), Cnestis (Parvez & Rahman, 1992), Connarus (Aiyar et al., 1964; 1965; Ramiah et al., 1976b; Marcano et al., 1984), and Rourea (Jiang et al., 1990; Zhang et al., 2008; Kalegari, 2009). "
[Show abstract][Hide abstract] ABSTRACT: The chromatography fractionation of the hexane, chloroform and ethyl acetate extracts from the leaves and stems of Rourea doniana Baker, Connaraceae, resulted in the isolation of five triterpenes (lupeol, lupenone, α-amyrenone, β-amyrenone, and taraxerol), a flavonol (7,4'-dimethylkaempferol), a coumarin (scopoletin) and four phytosteroids (β-sitosterol, stigmasterol, β-sitosteryl-3-O-β- D-glucopyranoside and stigmasteryl-3-O-β-D-glucopyranoside). All compounds are being for the first time in this species and all triterpenes and the flavonol are being described for the first time in the family Connaraceae. These compounds were identified on basis of their IR and NMR (1H, 13C, DEPT, HSQC, HMBC, and NOESY) spectral data and by comparison with literature data.
Revista Brasileira de Farmacognosia 04/2012; 22(2):451-454. DOI:10.1590/S0102-695X2011005000223 · 0.83 Impact Factor
[Show abstract][Hide abstract] ABSTRACT: This review covers the isolation, structure determination, synthesis, chemical transformations and biological activity of indolizidine and quinolizidine alkaloids. Included in the review are the hydroxylated indolizidines lentiginosine, swainsonine, castanospermine and their analogues; alkaloids from animal sources, including ants, amphibians and beetles; indolizidine alkaloids from the genera Polygonatum, Prosopis and Elaeocarpus; indolizidine and phenanthroindolizidine alkaloids; alkylquinolizidine alkaloids, including myrtine, epimyrtine, plumerinine and Lycopodium metabolites; Lythraceae and Nuphar alkaloids; lupine alkaloids; and alkaloids from marine sources. 150 references are cited.
[Show abstract][Hide abstract] ABSTRACT: This review covers the isolation, structure determination, synthesis, chemical transformations and biological activity of indolizidine and quinolizidine alkaloids. Included in the review are the hydroxylated indolizidines lentiginosine, swainsonine, castanospermine and their analogues; alkaloids from animal sources, including arthropods and amphibians; alkaloids from the genera Polygonatum, Prosopis and Poranthera; phenanthroindolizidine and phenanthroquinolizidine alkaloids; Nuphar alkaloids; lupine alkaloids; and alkaloids from marine sources. 130 references are cited.
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