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

• Abdjul Delfly Booby

  Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University North Sulawesi Research and Development Agency Faculty of Fisheries and Marine Science, Sam Ratulangi University

• Yamazaki Hiroyuki

  Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University

• Kanno Syu-ichi

  Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University

• Kirikoshi Ryota

  Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University

• Tomizawa Ayako

  Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University

• Takahashi Ohgi

  Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University

• Maarisit Wilmar

  Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University Faculty of Fisheries and Marine Science, Sam Ratulangi University

• Losung Fitje

  Faculty of Fisheries and Marine Science, Sam Ratulangi University

• Rotinsulu Henki

  Faculty of Mathematic and Natural Sciences, Sam Ratulangi University

• Wewengkang Defny Silvia

  Faculty of Mathematic and Natural Sciences, Sam Ratulangi University

• Sumilat Deiske Adeliene

  Faculty of Fisheries and Marine Science, Sam Ratulangi University

• Kapojos Magie Melanie

  Faculty of Nursing, University of Pembangunan Indonesia

• Namikoshi Michio

  Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University

書誌事項

タイトル別名

• Absolute Structures of Wedelolide Derivatives and Structure–Activity Relationships of Protein Tyrosine Phosphatase 1B Inhibitory <i>ent</i>-Kaurene Diterpenes from Aerial Parts of <i>Wedelia</i> spp. Collected in Indonesia and Japan

抄録

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.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 66 (6), 682-687, 2018-06-01

  公益社団法人 日本薬学会

キーワード

• <i>Wedelia prostrata</i>
• <i>Wedelia chinensis</i>
• family Asteraceae
• eudesmanolide sesquiterpene
• <i>ent</i>-kaurene diterpene
• protein tyrosine phosphatase 1B

詳細情報

• CRID: 1390001288036767872
• NII論文ID: 130007382328
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.c18-00117
• ISSN: 13475223
• ISSN: 00092363
• NDL書誌ID: 029007143
• PubMed: 29863070
• Web Site: http://id.ndl.go.jp/bib/029007143
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I029007143
• Web Site: https://www.jstage.jst.go.jp/article/cpb/66/6/66_c18-00117/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/2019071605
• 本文言語コード: en
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
  • KAKEN
• 抄録ライセンスフラグ: 使用不可