Lyngbya

Synthetic study of 4-thiazoline derivative curacin A, a novel antimitotic agent isolated from cyanobacterium Lyngbya majuscula 99YGK552. 

Indium-mediated allylation of an unreactive halide with an aldehyde132 was used to synthesize an advanced intermediate in the synthesis of antillatoxin,133 a marine cyanobacteria (Lyngbya majus-cula) that is one of the most ichthyotoxic compounds isolated from a marine plant to date. In the presence of a lanthanide triflate, the indium-mediated allylation of Z-2-bromocrotyl chloride and aldehyde in saturated NH4C1 under sonication yielded the desired advanced intermediate as a 1 1 mixture of diastereomers in 70% yield. Loh et al.134 then changed the halide compound to methyl (Z)-2-(bromomethyl)-2-butenoate and coupled it with aldehyde under the same conditions to yield the desired homoallylic alcohol in 80% yield with a high 93 7 syn anti selectivity (Eq. 8.55). 

More recently [135], 72 and 73 were also found in the sea hare Stylocheilus longicauda but, surprisingly, only dehalogenated 73 was present in the algal food source, Lyngbya majuscula. This metabolic comparison suggested an uncommon in vivo bromination of 73, but further experiments need to ascertain whether L. majuscula is the unique food source of S. longicauda. 

The absolute stereochemistries for both compounds were determined by CD analysis of the p-bromobenzoate derivatives. Two other eicosanoids were also isolated from whole animals [198], The trihydroxylated oxylipin 8jR,11S,12R-trihydroxyeicosa-5Z,9 ,14Z,17Z-tetraenoic acid (trioxilin A4,150) was detected in, or isolated from, five starfish species P. miniata, Dermasterias imbricata, Pycnopodia helianthoides, Culcita novaeguinea, and Nardoa tubercolata. Its structure was determined by H and 13C NMR and FAB-MS analyses of the natural product and of an acetonide derivative. The co6 analog of this compound (151) was isolated only from P. helianthoides. The relative stereochemistry in these metabolites (150, 151) was established from a comparison of NMR shifts with malyngic acid, a trihydroxylated C18 compound isolated from Lyngbya majuscula, while the absolute stereochemistry was proposed on the basis of the earlier isolation of 8R-HETE from P. miniata. 

The compound curacin A 207 is a novel antimitotic agent isolated from the Caribbean cyanobacterium Lyngbya majuscula. The compound consists of a disubstituted thiazoline bearing a chiral cyclopropane ring and an aliphatic side chain. Scheme 5-67 depicts the construction of the cyclopropane ring using an asymmetric cyclopropanation reaction.122... 

Nagle DG, Paul VJ (1999) Production of secondary metabolites by filamentous tropical marine cyanobacteria ecological functions of the compounds. J Phycol 35 1412-1421 Nagle DG, Camacho FT, Paul VJ (1998) Dietary preferences of the opisthobranch mollusc Stylocheilus longicauda for secondary metabolites produced by the tropical cyanobacterium Lyngbya majuscula. Mar Biol 132 267-273... 

Camacho FA, Thacker RW (2006) Aniphipod herbivory on the freshwater cyanobacterium Lyngbya wollei. chemical stimulants and morphological defenses. Limnol Oceanogr 51 1870-1875 Carmichael WW (1994) The toxins of cyanobacteria. Sci Am 2780 78-86 Carmichael WW (2001) Health effects of toxin-producing cyanobacteria the cyanoHABs . Hum Ecol Risk Assess 7 1393-1407... 

Onodera H, Satake M, Oshima Y, Yasumoto T, Carmichael WW (1997) New saxitoxin analogues from the freshwater cyanobacterium Lyngbya wollei. Nat Toxins 5 146-151 Paerl HW, Fulton III RS, Moisander PH, Dyble J (2001) Harmful freshwater algal blooms, with an emphasis on cyanobacteria. Sci World 1 76-113 Pouria S, de Andrade A, Barbosa J, Cavalcanti R, Barreto V, Ward C, Preiser W, Poon G, Neild G, Codd G (1998) Fatal microcystin intoxication in haemodialysis unit in Caruaru, Brazil. Lancet 352 21-26... 

Seifert M, McGregor G, Eaglesham G, Wickramasinghe W, Shaw G (2007) First evidence for the production of cylindrospermopsin and deoxy-cylindrospermopsin by the benthic freshwater cyanobacterium Lyngbya wollei (Farlow ex Gomont) Speziale and Dyck. Harmful Algae 6 73-80... 

For cells that occur under layers or inside colonies of scytonemin-producing taxa, the attentuation of UVA may be even more effective. The umbrella -function of scytonemin produced by surface layers of Lyngbya aestuarii in microbial mats for other cyanobacteria living underneath has already been described (Sect. 13.3.1) (Karsten et al. 1998a). 

H Fungi - Amanita phalloides and Agaricus phalloides Cyanobacteria -Lyngbya majuscula Phalloidin, phallicidin, and amanitin - toxic peptides Majusculamide D - cytotoxic peptide Microcolin A - peptide with immunosuppressive, antileukemic and protein kinase C inhibitory activity 242... 

One of the most toxic genera of marine cyanobacteria is Lyngbya — filamentous cyanobacteria within tropical and subtropical waters. Lyngbya... 

Of particular interest is Lyngbya majusculata which has been the subject of extensive studies. Interest in this species was first spurred by its ability to induce a dermatitis-like condition in swimmers ( swimmers itch ) which was traced to potent inflammatory, blister-producing and tumor promoting compounds such as aplysiatoxin, debromoaplysiatoxin and lyngbiatoxin... 

Han B, McPhail KL, Gross H, Goeger D, Mooberry SL, Gerwick WH, Isolation and structure of five lyngbyabellin derivatives from a Papua New Guinea collection of the marine cyanobacterium Lyngbya majuscule, Tetrahedron 61 11723-11729, 2005. 

Marine blue-green algae belonging to the Oscilla-toriaceae are frequently toxic. Lyngbya ma.iuscula. for example, is the causative agent of a severe contact dermatitis that sometimes affects swimmers and bathers at beaches on the windward side of Oahu,... 

Recently, the total synthesis of grenadamide, a naturally occuring chiral cyclopropyl amide isolated from marine cyanobacterium Lyngbya majuscula <1998JNP681>, was published employing the aforementioned diastereoselective cyclopropanation protocol as the key step in the synthesis <20060BC323>. 

Macrolide-macrolactams madaneolide and laineolide A-like Lyngbya bouillonii Hoifinan and Demoulin, Nostocales, Cyabact. from PNG Klein 1999). 

Pept barbamide and (lipopept.l microcolins and antillatoxin (Lyngbya majvscula Oomont, Cyanobact. Yokokawa 2000) salinamides (depsipept. from Streptomyces sp. Actinom., Bact. from jellyfish Cassiopeia xamachana from Florida keys Trischman 1994A). 

Aminoacid derivs malvngamides Lyngbya majuscula Gomont, Cyanobact. from Curasao, Caribbean Wu 1997 and the C6te d Azur, Mediterr. Mesguiche 1999). 

---