First Total Synthesis and Structure-Activity Relationship of Iheyamide A, an Antitrypanosomal Linear Peptide Isolated from a Dapissp. Marine Cyanobacterium

Arihiro Iwasaki, Kazuya Teranuma, Naoaki Kurisawa, Yulia Rahmawati, Ghulam Jeelani, Tomoyoshi Nozaki, William H. Gerwick, Kiyotake Suenaga

研究成果: Review article査読

抄録

Iheyamide A ( 1 ) is an antitrypanosomal linear peptide isolated from aDapissp. marine cyanobacterium by our group in 2020, and based on structure-activity relationships of its natural analogues, the C-terminal pyrrolinone moiety has been identified as the phamacophore for its antiparasitic activity. Further, we isolated this pyrrolinone moiety by itself as a new natural product from the marine cyanobacterium and named it iheyanone ( 2 ). As expected, iheyanone ( 2 ) showed antitrypanosomal activity, but its potency was weaker than iheyamide A ( 1 ). To clarify more detailed structure-activity relationships, we completed a total synthesis of iheyamide A ( 1 ) along with iheyanone ( 2 ) and evaluated the antitrypanosomal activities of several synthetic intermediates. As a result, we found that the longer the peptide chain, the stronger the antitrypanosomal activity. As iheyamide A ( 1 ) showed selective toxicity againstTrypanosoma brucei rhodesiense, these findings can provide design guidelines for antitrypanosomal drugs.

本文言語English
ページ(範囲)2587-2593
ページ数7
ジャーナルJournal of Natural Products
84
9
DOI
出版ステータスPublished - 2021 9月 24

ASJC Scopus subject areas

  • 分析化学
  • 分子医療
  • 薬理学
  • 薬科学
  • 創薬
  • 補完代替医療
  • 有機化学

フィンガープリント

「First Total Synthesis and Structure-Activity Relationship of Iheyamide A, an Antitrypanosomal Linear Peptide Isolated from a Dapissp. Marine Cyanobacterium」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル