Nonanolides of Natural Origin: Structure, Synthesis, and Biological Activity

P.      Sun; S.      Lu; T.      V. Ree; K.      Krohn; L.      Li; W.      Zhang

doi:10.2174/092986712801215874

Abstract

Naturally occurring nonanolides (synonym decanolides) are a large family of secondary metabolites with an interesting 10- membered macrolide subunit. Metabolites of the nonanolide family have been found to have various biological activities, including cytotoxic, phytotoxic, antimalarial, antifungal, antibacterial, and antimicrofilament activities. An early review of the chemistry and bioactivity of nonanolides was presented in 1996, covering the literature published between 1975 and 1995. During the past decades, the broad spectrum of bioactivity and the intriguing structure of the medium-sized ring in nonanolide analogues have continuously drawn the attention of biologists and natural product and synthetic chemists, resulting in a great number of publications. This review summarizes in whole the recent progress in the field of the nonanolides of natural origin, aiming to give the readers a brief view of the compounds, concerning their natural occurrence, structural elucidation, biological activities, total synthesis, and structure-activity relationships. The article covers the literature published in the period from the beginning of 1996 to July 2011.

Keywords: Nonanolide, nonenolide, decanolide, 10-membered lactone, fungal secondary metabolites, biological activity, phytotoxicity, synthesis, ring closing metathesis (RCM), Yamaguchi lactonization, structure-activity relationships (SAR)