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Mar. Drugs 2010, 8(6), 1803-1816; doi:10.3390/md8061803
Article

Intramolecular Modulation of Serine Protease Inhibitor Activity in a Marine Cyanobacterium with Antifeedant Properties

1
,
1
,
2,†
,
2
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2,*  and 1,*
1 Department of Medicinal Chemistry, University of Florida, 1600 SW Archer Road, Gainesville, FL 32610, USA 2 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 / Revised: 2 June 2010 / Accepted: 2 June 2010 / Published: 4 June 2010
(This article belongs to the Special Issue Algal Toxins)
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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 cyanobacteria; Lyngbya; antifeedant activity; serine protease inhibitors; cyclodepsipeptides
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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