Chemical Structural Requirement in Gingerol Derivatives for Potentiation of Prostaglandin F_<2α>-Induced Contraction in Isolated Mesenteric Veins of Mice

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We have previously reported that (±)-[6]-and (±)-[8]-gingerols potentiate prostaglandin (PG) F_<2α>-induced muscle contraction, and that other gingerol-related derivatives do not necessarily produce the same effect. The moiety necessary for potentiation was therefore investigated. 1) (±)-[8]-Gingerol potentiated PGF_<2α>-induced contraction to a greater extent than (±)-[6]-gingerol and (±)-hexahydrocurcumine (HHC), but [6]-shogaol produced inhibition ; 2) Noradrenaline (NA)-induced contraction was inhibited in the following order : [6]-shogaol>(±)-[8]-gingerol>[6]-gingerdione>(±)-[6]-gingerol>S-(+)-[6]-gingerdiacetate (GDA) >[6]-dehydrogingerdione (DHG), whereas (±)-HHC had no significant inhibitory action ; 3) [6]-gingerdione had different effects on PGF_<2α>-induced contraction, indicating inhibition just after preparation of the solution, no effect apparent after 2 h, and potentiation after 5 h ; 4) [6]-gingerdione showed a change in its chemical structure after 5 h as measured by the FeCl_3 reaction, and ultraviolet and ^1H nuclear magnetic resonance spectra. It was concluded that the aliphatic hydroxyl group present in gingerol derivatives is necessary for potentiation of PGF_<2α>-and the keto group for inhibition of NA-induced contraction.
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