106(P-46) 香辛料の胃粘膜保護作用成分と構造活性相関および作用機序 : マウンテンペパー,大良姜,ジャワナガコショウ,タイ人参(ポスター発表の部)

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In the course of our studies on the bioactive constituents from medicinal foods, the methanolic or 80% aqueous acetone extracts from the leaves of Tasmannia lanceolata, the rhizomes of Alpinia galanga, the fruit of Piper chuba, and the rhizomes of Boesenbergia rotunda were found to potently inhibit ethanol-induced gastric lesions in rats. Through bioassay-guided separation, we isolated various gastroprotective principles from the extracts and investigated the structural requirements for the activity and mode of action of the active compounds. 1. Tasmannia lanceolata: Polygodial (1), polygodial 12α-acetal (2), and polygodial 12β-acetal (3), and a new sesquiterpene, methyl isodrimeninol (4), were isolated as active constituents. Among them, compound 1 strongly inhibited the lesions induced by ethanol (ED_<50>=0.029 mg/kg), 0.6 M HCl (ED_<50>=0.26 mg/kg), aspirin (ED_<50>-0.38 mg/kg), and 1% ammonia (ED_<50>=0.067 mg/kg). From the gastroprotective effects of various derivatives of 1, the dialdehyde or diacetal structure was found to be essential for the strong activity. With regard to the mode of action of 1, endogenous prostaglandins, nitric oxide, and vanilloid receptors-mediated actions may be involved in the protective activity. 2. Alpinia galanga: 1'S-1'-Acetoxychavicol acetate (10S) and 1'S-1'-acetoxyeugenol acetate (11) markedly inhibited the ethanol-induced gastric mucosal lesions (ED_<50>=0.61 and 0.90 mg/kg). In addition, compound 10S inhibited the lesions induced by 0.6 M HCl (ED_<50>=0.73 mg/kg), aspirin (ED_<50>=0.69 mg/kg), and 1% ammonia (ED_<50>-0.61 mg/kg). From the gastroprotective effects of various related compounds, both the 1'- and 4-acetoxyl groups of 10S and 11 were essential for their strong activity. With regard to the mode of action of 10S, endogenous prostaglandins are involved in the protective activity. 3. Piper chaba: Amide constituents [e.g. piperine (30), piperonaline (31), retrofractamide B (32), N-isobutyl-(2E,4E)-octadecadienamide (33), etc.] significantly inhibited ethanol- and indomethacin-induced gastric lesions in rats at a dose of 25 mg/kg, p.o. and the amide structure of the active constituents was important for the activity. Compound 30 inhibited the lesions induced by aspirin (ED_<50>=39 mg/kg), 1% ammonia (ED_<50>=37 mg/kg), and water-immersion stress (ED_<50>=33 mg/kg) as well as ethanol (ED_<50>=24 mg/kg) and indomethacin (ED_<50>=13 mg/kg). 4. Boesenbergia rotunda: New Diels-Alder type conjugated prenylchalcones (35a-40b) were isolated and their structures were determined on the basis of physicochemical evidence. Among the isolated constituents, several prenylchalcones (36, 37) and a flavanone, pinocembrin (41), significantly inhibited ethanol- and/or indomethacin-induced gastric lesions by 56-69% at a dose of 10mg/kg, p.o.
天然有機化合物討論会の論文
2004-10-01

106(P-46) 香辛料の胃粘膜保護作用成分と構造活性相関および作用機序 : マウンテンペパー,大良姜,ジャワナガコショウ,タイ人参(ポスター発表の部)

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