論文

査読有り 責任著者
2018年

Absolute structures of wedelolide derivatives and structure–activity relationships of protein tyrosine phosphatase 1B inhibitory ent-kaurene diterpenes from aerial parts of wedelia spp. collected in Indonesia and Japan

Chemical and Pharmaceutical Bulletin
  • Delfly Booby Abdjul
  • Hiroyuki Yamazaki
  • Syu-ichi Kanno
  • Ryota Kirikoshi
  • Ayako Tomizawa
  • Ohgi Takahashi
  • Wilmar Maarisit
  • Fitje Losung
  • Henki Rotinsulu
  • Defny Silvia Wewengkang
  • Deiske Adeliene Sumilat
  • Magie Melanie Kapojos
  • Michio Namikoshi
  • 全て表示

66
6
開始ページ
682
終了ページ
687
記述言語
英語
掲載種別
研究論文(学術雑誌)
DOI
10.1248/cpb.c18-00117
出版者・発行元
Pharmaceutical Society of Japan

Two sesquiterpene lactones with the (9R)-eudesman-9,12-olide framework, wedelolides I and J, have been isolated together with five eudesmanolide sesquiterpenes and twelve ent-kaurene diterpenes from the aerial parts of Indonesian Wedelia prostrata. The absolute configurations of wedelolides I and J, proposed in the previous communication, were proven by comparing their experimental Electronic Circular Dichroism (ECD) spectra with the calculated ECD spectrum of wedelolide I. The phytochemical study on the aerial parts of Okinawan Wedelia chinensis led to the isolation of three other eudesmanolide sesquiterpenes in addition to the three sesquiterpenes and eleven diterpenes isolated from the Indonesian W. prostrata as above. However, the wedelolide derivatives found in the Indonesian plant were not detected. Among these compounds, most of the diterpenes inhibited protein tyrosine phosphatase (PTP) 1B activity, and a structure–activity relationship study revealed that the cinnamoyl group enhanced inhibitory activity. Therefore, two ent-kaurene derivatives with and without a cinnamoyl group were examined for the ability to accumulate phosphorylated-Akt (p-Akt) because PTP1B dephosphorylates signal transduction from the insulin receptor such as phosphorylated Akt, a key downstream effector. However, neither compound enhanced insulin-stimulated p-Akt levels in two human hepatoma cell lines (Huh-7 and HepG2) at non-cytotoxic doses.

リンク情報
DOI
https://doi.org/10.1248/cpb.c18-00117
URL
http://orcid.org/0000-0002-1540-7255
ID情報
  • DOI : 10.1248/cpb.c18-00117
  • ISSN : 1347-5223
  • ISSN : 0009-2363
  • ORCIDのPut Code : 51292468
  • SCOPUS ID : 85048031369

エクスポート
BibTeX RIS