Total synthesis and bioactivity of the marine alkaloid pityriacitrin and some of its derivatives

Puyong Zhang, Xiaofei Sun, Bin Xu, Krikor Bijian, Shengbiao Wan, Guigen Li, Moulay Alaoui-Jamali, Tao Jiang

Research output: Contribution to journalArticle

17 Scopus citations

Abstract

We report herein the chemical synthesis and biological evaluation of β-carboline alkaloid pityriacitrin and some of its new derivatives. Using tryptophan or 5-hydroxytryptophan and 5-substituted indole-3-glyoxals as the starting materials, pityriacitrin and some of its derivatives were synthesized via the acid-catalyzed Pictet-Spengler reaction and fully characterized by 1H and 13C NMR, mass spectroscopy and IR determinations. Biological studies revealed that pityriacitrin has a weak antiproliferative activity against a panel of breast and prostate cancer cell lines, whereas some of its derivatives exhibited stronger and potent activity, which was associated with induction of both cell apoptosis and necrosis.

Original languageEnglish
Pages (from-to)6089-6097
Number of pages9
JournalEuropean Journal of Medicinal Chemistry
Volume46
Issue number12
DOIs
StatePublished - Dec 2011

Keywords

  • Antiproliferative activity
  • Cytotoxicity
  • Indole-3-glyoxal
  • Pityriacitrin
  • Total synthesis
  • β-Carboline

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