Synthesis and biological activities of flavolipids

Samiul M. Ahad, Alison L. Ange, Robert B. Bates, Bonnie L. Bell, Adria A. Bodour, Bryan R. Bourne, Cristina G. Contreras, Emily L. Goldberg, A. A.Leslie Gunatilaka, Sheryl King, Albert K. Lee, Rebecca L. Low, Raina M. Maier, Kathryn M. Marlor, Marilyn T. Marron, Ryan C. Scolnik, Matthew J. Streeter, Malgorzata Strelczuk, Long N. Trinh, Vu K. TruongSage P. Vissering, Megan C. Weick, Maria T. Williams

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Syntheses of the bacterial surfactants 6S,6S-, 9S,9S-, and 9U,9U-flavolipids confirmed the structures proposed for them from spectroscopic analysis of a flavolipid mixture and made pure flavolipids available for the first time. All three synthetic flavolipids and a straight chain analogue were found to be weakly cytotoxic and to inhibit metastatic cancer cell migration, with 9U,9U-flavolipid (the most abundant natural flavolipid) having the most activity. Biosynthetic routes to the branched side-chains of the flavolipids are suggested, and it is proposed that branched chains are employed to hinder biodegradation.

Original languageEnglish (US)
Pages (from-to)9107-9112
Number of pages6
JournalTetrahedron
Volume66
Issue number47
DOIs
StatePublished - Nov 20 2010

Keywords

  • Biosurfactant
  • Flavobacterium
  • Flavolipid
  • Siderophore

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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