Chemical structural requirement in gingerol derivatives for potentiation of prostaglandin F2 alpha-induced contraction in isolated mesenteric veins of mice.
We have previously reported that (+/-)-[6]- and (+/-)-[8]-gingerols potentiate prostaglandin (PG) F2 alpha-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 PGF2 alpha-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 greater than (+/-)-[8]-gingerol greater than [6]-gingerdione greater than (+/-)-[6]-gingerol greater than S-(+)-[6]-gingerdiacetate (GDA) greater than [6]-dehydrogingerdione (DHG), whereas (+/-)-HHC had no significant inhibitory action; 3) [6]-gingerdione had different effects on PGF2 alpha-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 FeCl3 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 PGF2 alpha- and the keto group for inhibition of NA-induced contraction.
Kimura
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I
Department of Chemical Pharmacology, Toyama Medical and Pharmaceutical University, Japan.
Pancho
L R
LR
Koizumi
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T
Kimura
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M
D000818:Animals; D002396:Catechols; D055598:Chemical Phenomena; D002621:Chemistry; D015237:Dinoprost / Q000502:physiology*; D004357:Drug Synergism; D005233:Fatty Alcohols / Q000494:pharmacology; D066298:In Vitro Techniques; D008297:Male; D008642:Mesenteric Veins / Q000502:physiology; D051379:Mice; D008815:Mice, Inbred Strains; D009119:Muscle Contraction / Q000187:drug effects*; D010946:Plants, Medicinal; D013329:Structure-Activity Relationship
D002396:Catechols; D005233:Fatty Alcohols; C007845:gingerol; D015237:Dinoprost