Punica granatum structure

The simple piperidine pelletierine from Punica granatum (pomegranate) (Punicaceae) and Duboisia myoporoides (Solanaceae) is an anthelmintic. The simple piperidine derivatives deoxy-mannojirimycin (DMJ) and deoxynojirimycin (DNJ) from Lonchocarpus species (Fabaceae) are glycosidase inhibitors because they are structurally similar to the pyranose (six-membered ring) sugar moieties of the glycosidase disaccharide substrates. 

V-(2, 5 -Dihydroxyphenyl)pyridinium chloride (116) was isolated from leaf extract of Punica granatum[333]. Its structure was established with UV, FABMS. one- and two-dimensional H and 13C NMR, formation of a precipitate with aqueous AgNQ3, and alkaline fusion to give hydroquinone [333]. 

The biosynthesis, occurrence, and biological activities of piperidine alkaloids arising from lysine have been studied Punica granatum. Piper species, and Lobelia inflata). The isolation process, chromatographic purification/analysis, and structure elucidation of the significant alkaloids are discussed. 

While for developing of simple piperidine alkaloids, e.g., pelletierine (Punica granatum), piperine (Piper nigrum et longum), and lobeline (Lobelia inflata), only one molecule of lysine is necessary, for quinolizidine alkaloids - e.g., lupinine (Lupinus luteus), sparteine of antiarrhythmic activity (Sarothamnus scoparius), and cytisine of respiratory stimulant effect (Laburnum species) - two molecules of lysines are indispensable. It was also proved that lycopodine (Lycopodium tristachyum, clubmoss) of quinolizidine structure has no polyketide origin, but it is a modified dimer of pelletierine, which, in turn, is derivable from lysine and acetate. 

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