Dioncophyllidine E: The first configurationally semi-stable, 7,3′-coupled naphthyldihydroisoquinoline alkaloid, from Ancistrocladus abbreviatus, with antiausterity activity against PANC-1 human pancreatic cancer cells

Shaimaa Fayez, Alessia Cacciatore, Juthamart Maneenet, Hung Hong Nguyen, Nasir Tajuddeen, Doris Feineis, Laurent Aké Assi, Suresh Awale*, Gerhard Bringmann

*この論文の責任著者

研究成果: ジャーナルへの寄稿学術論文査読

2 被引用数 (Scopus)

抄録

The discovery of a new naphthylisoquinoline alkaloid, dioncophyllidine E (4), from the tropical liana Ancistrocladus abbreviatus (Ancistrocladaceae) is described. Due to its rare 7,3′-coupling type, combined with the lack of an oxygen function at C-6, it is configurationally semi-stable at the biaryl axis, and thus occurs as a pair of slowly interconverting atropo-diastereomers, 4a and 4b. Its constitution was assigned mainly by 1D and 2D NMR. The absolute configuration at the stereocenter, C-3, was elucidated by oxidative degradation. The absolute axial configuration of the individual atropo-diastereomers was established by their HPLC resolution, combined with online electronic circular dichroism (ECD) investigations, providing nearly mirror-imaged LC-ECD spectra. These were assigned to the respective atropisomers by ECD comparison with a related, but configurationally stable alkaloid, ancistrocladidine (5). Dioncophyllidine E (4a/4b) exhibits a strong preferential cytotoxicity against PANC-1 human pancreatic cancer cells under nutrient-deprived conditions, with a PC50 value of 7.4 µM, suggesting its potential as an agent against pancreatic cancer.

本文言語英語
論文番号129234
ジャーナルBioorganic and Medicinal Chemistry Letters
86
DOI
出版ステータス出版済み - 2023/04/15

ASJC Scopus 主題領域

  • 生化学
  • 分子医療
  • 分子生物学
  • 薬科学
  • 創薬
  • 臨床生化学
  • 有機化学

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