Xanthine Oxidase Inhibitory Activities and Crystal Structures of Methoxyflavones from Kaempferia parviflora Rhizome

被引:33
作者
Nakao, Kikuyo [2 ]
Murata, Kazuya [1 ]
Deguchi, Takahiro [1 ]
Itoh, Kimihisa [1 ]
Fujita, Takanori [3 ]
Higashino, Masayuki [3 ]
Yoshioka, Yuri [4 ]
Matsumura, Shin-ichi [4 ]
Tanaka, Rika [5 ]
Shinada, Tetsuro [6 ]
Ohfune, Yasufumi [6 ]
Matsuda, Hideaki [1 ]
机构
[1] Kinki Univ, Fac Pharm, Osaka 5778502, Japan
[2] Kinki Univ, Res Inst Oriental Med, Osaka 5898511, Japan
[3] Japan Tablet Corp, Kyoto 6110041, Japan
[4] Inabata Koryo Co Ltd, Yodogawa Ku, Osaka 5320027, Japan
[5] Osaka City Univ, Grad Sch Engn, Osaka 5588585, Japan
[6] Osaka City Univ, Grad Sch Sci, Osaka 5588585, Japan
关键词
Zingiberaceae; Kaempferia parviflora rhizome; xanthine oxidase; methoxyflavone; crystal structure; FLAVONOIDS; REQUIREMENTS;
D O I
10.1248/bpb.34.1143
中图分类号
R9 [药学];
学科分类号
1007 ;
摘要
Kaempferia parviflora (KP), a Zingiberaceae plant, is used as a folk medicine in Thailand for the treatment of various symptoms, including general pains, colic gastrointestinal disorders, and male impotence. In this study, the inhibitory activities of KP against xanthine oxidase (XOD) were investigated. The extract of KP rhizomes showed more potent inhibitory activity (38% at 500 mu g/ml) than those of the other Zingiberaceae plants tested. Ten methoxyflavones were isolated from the KP extract as the major chemical components and their chemical structures were elucidated by X-ray crystallography. The structurally confirmed methoxyflavones were subjected to the XOD inhibitory test. Among them, 3,5,7,4',5'-pentamethoxyflavone and 3',4',5,7-tetramethoxyflavone showed inhibitory activities (IC50 of 0.9 and >4 mM, respectively) and their modes of inhibition are clarified as competitive/non-competitive mixed type. To the best of our knowledge, this is the first report to present the inhibitory activities of KP, 3,5,7,4',5'-pentamethoxyflavone and 3',4',5,7-tetramethoxyflavone against XOD.
引用
收藏
页码:1143 / 1146
页数:4
相关论文
共 29 条
  • [1] Antiobesity effects of Kaempferia parviflora in spontaneously obese type II diabetic mice
    Akase, Tomoko
    Shimada, Tsutomu
    Terabayashi, Susumu
    Ikeya, Yukinobu
    Sanada, Hiromi
    Aburada, Masaki
    [J]. JOURNAL OF NATURAL MEDICINES, 2011, 65 (01) : 73 - 80
  • [2] 3,5,7-Trimethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one
    Aree, Thammarat
    Sawasdee, Pattara
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O2706 - U382
  • [3] Phenolic glycosides from Kaempferia parviflora
    Azuma, Toshiaki
    Tanaka, Yasuo
    Kikuzaki, Hiroe
    [J]. PHYTOCHEMISTRY, 2008, 69 (15) : 2743 - 2748
  • [4] CHANG WS, 1993, ANTICANCER RES, V13, P2165
  • [5] Estrogenic activities of isoflavones and flavones and their structure-activity relationships
    Choi, Sun Young
    Ha, Tae Youl
    Ahn, Ji Yun
    Kim, Sung Ran
    Kang, Kyung Sun
    Hwang, In Kyeong
    Kim, Suna
    [J]. PLANTA MEDICA, 2008, 74 (01) : 25 - 32
  • [6] 5-hydroxy-3,7-dimethoxy-2-phenyl-4H-1-benzo-pyran-4-one
    Fun, HK
    Razak, IA
    Boonnak, N
    Laphookhieo, S
    Chantrapromma, S
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O3086 - O3088
  • [7] Mastuda H., 2002, CHEM PHARM BULL, V50, P788
  • [8] Structural requirements of flavonoids for inhibition of protein glycation and radical scavenging activities
    Matsuda, H
    Wang, T
    Managi, H
    Yoshikawa, M
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (24) : 5317 - 5323
  • [9] Structural requirements of flavonoids for nitric oxide production inhibitory activity and mechanism of action
    Matsuda, H
    Morikawa, T
    Ando, S
    Toguchida, I
    Yoshikawa, M
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (09) : 1995 - 2000
  • [10] MATSUDA H, 2002, BIOORGAN MED CHEM, V10, P3123