Structure and physiological activity of phenyl propanoid glycosides of Hassaku (Citrus hassaku Hort.) and orange (Citrus sinensis Osbeck.) peelings.

Abstract
The structure and hypotensive effect of phenyl propanoid glycosides in hassaku and orange peels are described in a series of studies of physiologically active substances in citrus peels. Six phenyl propanoid glycosides were isolated, and their structures were established: conferin[1], syringin[2], dehydrodiconiferyl alcohol-4-.beta.-glucoside[3], 1-(4-glucosyl-3-methoxyphenyl)-2-{2-methoxy-4-[1-(E)-propene-3-ol]-phenoxy}-propane-1,3-diol[4], 1-(4-glucosyl-3-methoxyphenyl)-2-{2,6-dimethoxy-4-[1-(E)-propene-3-ol]-phenoxy}-propane-1,3-diol[5] and 1-(4-glucosyl-3-methoxyphenyl)-propane-2-ene[6] by MS, UV, 1H-NMR and 13C-NMR spectroscopy and chemical evidence. We propose the terms citrusin A, B and C for these new phenyl propanoid glycosides ([4], [5] and [6]). Each component was intravenously injected in SHR-SP rats (1 mg/100 g body weight), and compounds [1] and [2] were found to raise rat blood pressure, but compounds [3], [4] and [6] lower rat blood pressure.

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