The use of the lactone motif in chemical communication

Abstract

A wide variety of organisms communicate via the chemical channel using small molecules. A structural feature quite often found is the lactone motif. In the present paper, the current knowledge on such lactones will be described, concentrating on the structure, chemistry, function, biosynthesis and synthesis of these compounds. Lactone semiochemicals from insects, vertebrates and bacteria, which this article will focus on, are particularly well investigated. In addition, some ideas on the advantageous use of lactones as volatile signals, which promoted their evolutionary development, will be discussed.

Biotransformation of Lactones with Methylcyclohexane Ring and Their Biological Activity

“…They are found in every ecosystem because they are the products of the secondary metabolism of microorganisms [1], insects [2], plants [3] and even marine organisms [4]. Lactones have a wide spectrum of biological activity and are quite a large group of compounds with bactericidal [5,6], fungicidal [7,8] or cytotoxic activities [9,10].…”

(1 R ,6 R )-2,2,6-Trimethyl-3-oxabicyclo[4.2.0]octan-4-one, a new monoterpene lactone produced by males of the cocoa borer Conotrachelus humeropictus (Col.: Curculionidae)

“…There are, however, only a few terpene lactones known as semiochemicals. 28 To the best of our knowledge, grandisolide is (apart from iridoid lactones, found in leaf beetles) the first monoterpene lactone identified in beetles. Bioassays to reveal the biological significance of the Conotrachelus compounds are under way.…”

Selected Compounds Modulate Various Inflammatory Biomarkers in Lipopolysaccharide-Induced Macrophages of PPAR-α Knockout Mice

“…Lactacystin is a potent proteasome inhibitor and played important role in ubiquitin-proteasome pathway in various cellular inflammatory processes, such as cell cycle, apoptosis, and the degradation of regulatory or membrane proteins [17]. (-) Corey lactone is a hydroxyl-lactone intermediate for the synthesis of prostaglandins and prostaglandin analogs, and ouabain plays an active role in the transport of Na + -K + -ATPase in the brain, and also involved in the regulation of several inflammatory cell functions (proliferation, hypertrophy, apoptosis, mobility, and metabolism) [18,19]. Ouabain is endogenously produced in mammals and circulates in plasma as a hormone in normal condition and disease.…”