Newly synthesized oleylgingerol and oleylshogaol activate TRPV1 ion channels.
The oleyl moiety in vanilloids is important in activating vanilloid receptor 1 (TRPV1), but there was no ingredient of ginger containing the oleyl moiety in the natural form. We synthesized oleylgingerol and oleylshogaol and then evaluated their potential to activate a rat TRPV1 channel. Oleylgingerol is a stronger TRPV1 agonist than natural gingerols, but oleylshogaol is a weaker agonist than natural shogaols. The difference in structure between oleylgingerol and oleylshogaol is only the hydroxy group at carbon-5. This hydroxy group might have an important role in activating a TRPV1 channel.
Morita
Akihito
A
School of Food and Nutritional Sciences and COE Program in the 21st Century, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
Iwasaki
Yusaku
Y
Kobata
Kenji
K
Yokogoshi
Hidehiko
H
Watanabe
Tatsuo
T
D000818:Animals; D002118:Calcium / Q000378:metabolism; D002460:Cell Line; D005233:Fatty Alcohols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D007668:Kidney / Q000187:drug effects / Q000378:metabolism; D015394:Molecular Structure; D051381:Rats; D013329:Structure-Activity Relationship; D050916:TRPV Cation Channels / Q000378:metabolism*