Medicinal foodstuffs.: XXXIV.: Structures of new prenylchalcones and prenylflavanones with TNF-α and aminopeptidase N inhibitory activities from Boesenbergia rotunda
Medicinal foodstuffs.: XXXIV.: Structures of new prenylchalcones and prenylflavanones with TNF-α and aminopeptidase N inhibitory activities from Boesenbergia rotunda
复制标题
DOI：
10.1248/cpb.56.956
复制
发表时间：
2008-07-01
影响因子：
1.7
通讯作者：
Yoshikawa, Masayuki
中科院分区：
文献类型：
--
作者：
Morikawa, Toshio;Funakoshi, Kanako;Yoshikawa, Masayuki
发现来自Boesenbergia rotunda（小檗科）根茎的甲醇提取物对L929细胞中肿瘤坏死因子-α（TNF-α）诱导的细胞毒性显示出抑制作用（IC 50 =6.1 μ g/ml）。通过生物活性导向分离，分离得到4个新的异戊烯基钙酮：（+）-克拉柴辛A（1a）、（-）-克拉柴辛A（1b）、（+）-克拉柴辛B（2a）和（-）-克拉柴辛B（2b），以及4个新的异戊烯基黄烷酮：圆轴黄酮Ia（3a）、Ib（3b）、IIa（4a）和IIb（4 b），以及18个已知的化合物（5a-7 b和8-19）。根据理化性质鉴定了8个新化合物的结构。其中，（+）-克拉柴素B（2a）、（-）克拉柴素B（2B）、（+）-4-羟基潘杜素A（6a）、（-）-4-羟基潘杜素A（6 B）、（+）-异潘杜素A（7a）、（-）-异潘杜素A（7 B）、山姜素（10）、小豆蔻素（14）和2，6-二羟基-4-甲氧基二氢查耳酮（15）在10 μ M时显著抑制L929细胞中TNF-α诱导的细胞毒性。此外，还发现2a，2b，（+）-panduratinA（5a），（-）-panduratinA（5 b），6a，7 b和香叶基-2，4-二羟基-6-苯基苯甲酸酯（17）对氨肽酶N活性有较强的抑制作用。
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 (IC50=6.1 mu g/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 mu M. 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.