Medicinal foodstuffs. XXXIV. Structures of new prenylchalcones and prenylflavanones with TNF-alpha and aminopeptidase N inhibitory activities from Boesenbergia rotunda.
The methanolic extract from the rhizomes of Boesenbergia rotunda (Zingiberaceae) was found to show inhibitory effect on tumor necrosis factor-alpha (TNF-alpha)-induced cytotoxicity in L929 cells (IC(50)=6.1 microg/ml). By bioassay-guided separation, four new prenylcalcones, (+)-krachaizin A (1a), (-)-krachaizin A (1b), (+)-krachaizin B (2a), and (-)-krachaizin B (2b), and four new prenylflavanones, rotundaflavones Ia (3a), Ib (3b), IIa (4a), and IIb (4b), were isolated together with 18 known constituents (5a-7b and 8-19). The structures of eight new compounds were elucidated on the basis of physicochemical evidence. Among them, (+)-krachaizin B (2a), (-)-krachaizin B (2b), (+)-4-hydroxypanduratin A (6a), (-)-4-hydroxypanduratin A (6b), (+)-isopanduratin A (7a), (-)-isopanduratin A (7b), alpinetin (10), cardamonin (14), and 2,6-dihydroxy-4-methoxydihydrochalcone (15) significantly inhibited TNF-alpha-induced cytotoxicity in L929 cells at 10 microM. In addition, 2a, 2b, (+)-panduratins A (5a), (-)-panduratin A (5b), 6a, 7b, and geranyl-2,4-dihydroxy-6-phenylbenzoate (17) were found to show strong inhibitory effects on aminopeptidase N activity.
Morikawa
Toshio
T
Pharmaceutical Research and Technology Institute, Kinki University, Osaka, Japan.
Funakoshi
Kanako
K
Ninomiya
Kiyofumi
K
Yasuda
Daisuke
D
Miyagawa
Katsutoshi
K
Matsuda
Hisashi
H
Yoshikawa
Masayuki
M
D017209:Apoptosis / Q000187:drug effects; D018826:CD13 Antigens / Q000037:antagonists & inhibitors*; D047188:Chalcones / Q000494:pharmacology*; D044950:Flavanones / Q000494:pharmacology*; D011480:Protease Inhibitors / Q000737:chemistry*; D014409:Tumor Necrosis Factor-alpha / Q000037:antagonists & inhibitors*; D030521:Zingiberaceae / Q000737:chemistry*
D047188:Chalcones; D044950:Flavanones; D011480:Protease Inhibitors; D014409:Tumor Necrosis Factor-alpha; D018826:CD13 Antigens