P-23 南米産薬用植物Pau ferro由来のフラボノイド類 : その構造と多様な生理活性(ポスター発表の部)

• 城戸 雅裕

  愛媛大総合科学研究支援セ:愛媛大院理工

• 谷 弘幸

  愛媛大総合科学研究支援セ:愛媛大院理工

• 高岡 大輔

  愛媛大教育

• 小野 昇

  愛媛大院理工

• 林 謙一郎

  岡理大理

• 松浦 信康

  岡理大理

• 野崎 浩

  岡理大理

• 赤尾 幸博

  岐阜県国際バイオ研

• 飯沼 宗和

  岐阜薬大

• 原口 博行

  福山大生命

書誌事項

タイトル別名

• P-23 Flavonoids from South American Medicinal Plant, Pau Ferro : Their Structures and Interesting Bioactivities

抄録

The South American medicinal plant called Pau ferro is a tall tree belonging to the leguminous genus Caesalpinia. Little chemical constituents other than gallic acid and ellagic acid in this plant have been reported so far. The acetone extracts of this bark exhibited the remarkable inhibitory activity on DNA topoisomerase II, and induced potent apoptosis in human leukemia cell line HL-60. In search of the bioactive substances, a variety of flavonoids including novel chalcone oligomers (1-5), prenyl flavone (7) and known compounds (amentoflavone (6), karanjachromene (8), 3',5'-dimethoxy-[2",3": 7,8]-furano flavone (9), desmethoxy kanugin (10)) were found from the bark extracts. In this paper, we report their compounds concerning the chemical structures and the biological activities. The molecular formulas of 1-5 and 7 were determined by HR-FABMS and HR-EIMS. Their planar structures were elucidated by the MS fragmentations and by using various NMR techniques (^1H, ^<13>C,^1H^1H-COSY, HMQC, and HMBC). The relative configurations of fran ring in 1-5 were deduced to be trans positions from NOESY. The stereochemistry around cyclobutane ring of 5 was presumed from the NOE difference spectra. Interestingly, 5 was a first example of chalcone trimer having cyclobutane structure. The chemical structures of all known compounds were identified by the comparison with published spectroscopic data. The isolated compounds were mainly evaluated for three bioactivities: inhibitory activity on DNA topoisomerase II, apoptosis induction in human leukemia cell line HL-60, and antidiabetic efficacy. 5 and 6 exhibited the inhibitory activities on topo II with IC_<50>-value of 2.1 and 8.3μM, respectively. 5 also revealed apoptosis in HL-60 with IC_<50> = 5.2μM. 8 showed cytotoxicity reaction of IC_<50> = 8.2μM. PPARα or γ activation potency as to antidiabetic efficacy was recognized on 9.

収録刊行物

• 天然有機化合物討論会講演要旨集

  天然有機化合物討論会講演要旨集 49 (0), 305-310, 2007

  天然有機化合物討論会実行委員会

詳細情報

• CRID: 1390282681054507264
• NII論文ID: 110006682782
• DOI: 10.24496/tennenyuki.49.0_305
• ISSN: 24331856
• 本文言語コード: ja
• データソース種別:
  • JaLC
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可