New amides and gastroprotective constituents from the fruit of Piper chaba.
The 80 % aqueous acetone extract from the fruit of Piper chaba was found to show protective effects on ethanol- and indomethacin-induced gastric lesions in rats. From the aqueous acetone extract, four new amides named piperchabamides A ( 1), B ( 2), C ( 3), and D ( 4) were isolated, and their structures were determined on the basis of chemical and physicochemical evidence. In addition, the gastroprotective effects of the principal constituents, piperine ( 5), piperanine ( 6), pipernonaline ( 7), dehydropipernonaline ( 8), piperlonguminine ( 9), retrofractamide B ( 10), guineensine ( 11), N-isobutyl-(2 E,4 E)-octadecadienamide ( 12), N-isobutyl-(2 E,4 E,14 Z)-eicosatrienamide ( 13), and methyl piperate ( 14), were examined. As a result, compounds 5 - 10 and 12 - 14 significantly inhibited ethanol-induced gastric lesions at a dose of 25 mg/kg, p. o., while 5, 7, 8, 10, 12, and 13 also significantly inhibited indomethacin-induced gastric lesions at the same dose.
Morikawa
Toshio
T
Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto, Japan. shoyaku@mb.kyoto-phu.ac.jp
Matsuda
Hisashi
H
Yamaguchi
Itadaki
I
Pongpiriyadacha
Yutana
Y
Yoshikawa
Masayuki
M
D000577:Amides / Q000008:administration & dosage / Q000627:therapeutic use; D000818:Animals; D000897:Anti-Ulcer Agents / Q000008:administration & dosage / Q000627:therapeutic use*; D000431:Ethanol; D005638:Fruit; D007213:Indomethacin; D008517:Phytotherapy; D026321:Piperaceae; D010936:Plant Extracts / Q000008:administration & dosage / Q000627:therapeutic use*; D051381:Rats; D013276:Stomach Ulcer / Q000139:chemically induced / Q000517:prevention & control*
D000577:Amides; D000897:Anti-Ulcer Agents; D010936:Plant Extracts; D000431:Ethanol; D007213:Indomethacin