Seaweed Dermatitis: Structure of Lyngbyatoxin A

Abstract

A highly inflammatory and vesicatory substance, lyngbyatoxin A, has been isolated from the lipid extract of a Hawaiian shallow-water variety of Lyngbya majuscula Gomont; its gross structure was determined from chemical and spectral data. Lyngbyatoxin A is closely related to teleocidin B, a poisonous substance associated with several strains of Streptomyces.

Chemical Defenses: From Compounds to Communities

“…The ecological functions of the biologically active secondary metabolites produced by L. majuscula are not clearly understood, but LTA has been shown to be toxic to fish (Cardellina et al, 1979), and several Lyngbya metabolites deter grazing in potential generalist herbivores Paul, 1998, 1999;Paul et al, 2001;Cruz-Rivera and Paul, 2007). While some animals may utilize L. majuscula as a refuge from predation, most do not selectively forage on L. majuscula, and secondary metabolites apparently render this ephemeral food source unpalatable to most generalist grazers (Nagle et al, 1996Pennings et al, 1996;Capper et al, 2006a;Cruz-Rivera and Paul, 2007).…”

“…Lyngbyatoxin A is a potent tumor promoter in mice (Cardellina et al, 1979;Fujiki et al, 1983). In the presence of an initiating agent (dimethylbenzoic acid), the application of LTA resulted in a tumor incidence of 80% in treated mice 21 weeks after application (Fujiki et al, 1983).…”

“…Lyngbya majuscula produces a wide variety of secondary metabolites, and LTA production varies among collections from different locations worldwide. For example, it has been isolated from L. majuscula in Hawaii (Cardellina et al, 1979), Australia (Capper, 2004;Osborne, 2004), Guam (D. Nagle and V. Paul, unpubl. results), and Japan (Izumi and Moore, 1987), but has not yet been detected in Lyngbya collections from Florida (Paul et al, 2005).…”

“…Lyngbyatoxin A (LTA) is an indole alkaloid that was first isolated from Lyngbya majuscula collected in the Hawaiian Islands, where it caused potent skin irritation in swimmers who came into contact with it (Cardellina et al, 1979) (Fig. 2).…”

Developmental Biology of Neoplastic Growth

“…Lyngbyatoxin A was isolated from the cyanobacterium (blue-green alga) Lyngya majuscula, and is structurally identical to teleocidin A-1 (Fig. 4) (Cardellina et al 1979;Fujiki et al 1984a).…”