Discovery, Characterization, and Analogue Synthesis of Bohemamine Dimers Generated by Non-enzymatic Biosynthesis

Peng Fu, Aaron Legako, Scott La, John B. MacMillan

Research output: Contribution to journalArticle

13 Scopus citations

Abstract

Dibohemamines A-C (5-7), three new dimeric bohemamine analogues dimerized through a methylene group, were isolated from a marine-derived Streptomyces spinoverrucosus. The structures determined by spectroscopic analysis were confirmed through the semi-synthetic derivatization of monomeric bohemamines and formaldehyde. These reactions, which could occur under mild conditions, together with the detection of formaldehyde in the culture, revealed that this dimerization is a non-enzymatic process. In addition to the unique dimerization of the dibohemamines, dibohemamines B and C were found to have nm cytotoxicity against the non-small cell-lung cancer cell line A549. In view of the potent cytotoxicity of compounds 6 and 7, a small library of bohemamine analogues was generated for biological evaluation by utilizing a series of aryl and alkyl aldehydes.

Original languageEnglish (US)
Pages (from-to)3491-3495
Number of pages5
JournalChemistry - A European Journal
Volume22
Issue number10
DOIs
Publication statusPublished - Mar 1 2016

    Fingerprint

Keywords

  • bohemamine
  • cancer
  • cytotoxicity
  • marine-derived streptomyces
  • non-enzymatic biosynthesis

ASJC Scopus subject areas

  • Chemistry(all)

Cite this