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Intramolecular Modulation of Serine Protease Inhibitor Activity in a Marine Cyanobacterium with Antifeedant Properties
Department of Medicinal Chemistry, University of Florida, 1600 SW Archer Road, Gainesville, FL 32610, USA
Smithsonian Marine Station, 701 Seaway Drive, Fort Pierce, FL 34949, USA
Present address: Center for Advanced Studies of Blanes (CEAB, CSIC), Acc Cala S Francesc 14, 17300 Blanes (Girona), Spain.
* Authors to whom correspondence should be addressed.
Received: 15 April 2010; in revised form: 2 June 2010 / Accepted: 2 June 2010 / Published: 4 June 2010
Abstract: Extracts of the Floridian marine cyanobacterium Lyngbya cf. confervoides were found to deter feeding by reef fish and sea urchins (Diadema antillarum). This antifeedant activity may be a reflection of the secondary metabolite content, known to be comprised of many serine protease inhibitors. Further chemical and NMR spectroscopic investigation led us to isolate and structurally characterize a new serine protease inhibitor 1 that is formally derived from an intramolecular condensation of largamide D (2). The cyclization resulted in diminished activity, but to different extents against two serine proteases tested. This finding suggests that cyanobacteria can endogenously modulate the activity of their protease inhibitors.
Keywords: cyanobacteria;Lyngbya; antifeedant activity; serine protease inhibitors; cyclodepsipeptides
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Matthew, S.; Ratnayake, R.; Becerro, M.A.; Ritson-Williams, R.; Paul, V.J.; Luesch, H. Intramolecular Modulation of Serine Protease Inhibitor Activity in a Marine Cyanobacterium with Antifeedant Properties. Mar. Drugs 2010, 8, 1803-1816.
Matthew S, Ratnayake R, Becerro MA, Ritson-Williams R, Paul VJ, Luesch H. Intramolecular Modulation of Serine Protease Inhibitor Activity in a Marine Cyanobacterium with Antifeedant Properties. Marine Drugs. 2010; 8(6):1803-1816.
Matthew, Susan; Ratnayake, Ranjala; Becerro, Mikel A.; Ritson-Williams, Raphael; Paul, Valerie J.; Luesch, Hendrik. 2010. "Intramolecular Modulation of Serine Protease Inhibitor Activity in a Marine Cyanobacterium with Antifeedant Properties." Mar. Drugs 8, no. 6: 1803-1816.