Lyngbya majuscula

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

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... 

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... 

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>. 

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

Koehn, F.E. Longley, R.E. Reed, J.K. (1992) Microcolins A and B, new immunosuppressive peptides from the blue-green alga Lyngbya majuscula. J. Nat. Prod., J5, 613-9. 

Moore, R.E. Entzeroth, M. (1988) Majusculamide D and deoxymajusculamide D, two cytotoxins from Lyngbya majuscula. Phj tochemistry, 27, 3101-3. 

Nagle, D.G. Paul, V.J. Roberts, M.A. (1996) Ypaoamide, a new broadly acting feeding detorent from the marine cyanobacterium Lyngbya majuscula. Tetrahedron Lett., 37, 6263-6. 

Wu, M. Milligan, K.E. Gawick, W.H. (1997) Three new malyngamides from the marine cyanobactaium Lyngbya majuscula. Tetrahedrcm, 53, 15983-90. 

Bonnard, I., Rolland, M., Francisco, C, and Banaigs, B. (1997). Total structure and biological properties of laxaphycins A and B, cyclic lipopeptides from the marine cyanobacterium Lyngbya majuscula. Lett. Pept. Sci. 4, 289-292. 

Although terrestrial cyanobacteria are well-recognized producers of a wide range of bioactive compounds, marine species have received less attention until recently [159]. One of the most abundant and studied marine cyanobacteria is the pantropic Lyngbya majuscula (Oscillatoriaceae). A prolific producer of metabolites, it has so far yielded more than 110 secondary metabolites including compounds that exhibit antiproliferative, immunosuppressants, antifeedant and molluscidal activities [159,160]. Shallow water varieties of the cyanophyte contain N-substituted amides of 75-methoxytetradec-4E-enoic acid and of 7S-methoxy-9-methylhexa-dec-4 -enoic acid called malyngamides, a sub-class of which contains the 4-methoxy-3-pyrrolin-2-one system [158]. 

The dysideathiazoles (420-424) were also reported from the same sponge and their structures were determined by spectroscopic methods and X-ray analyses [326]. More recently, new variations of this type of unique marine metabolite were obtained. Herbamide A (425) [327] was isolated from a collection of D. herbacea, presumed to be rich in cyanobacteria because of the rich presence of chrorophyll, and barbamide (426) [328] was obtained from the cyanobacterium Lyngbya majuscula. Faulkner and... 

The Hawaiian Lyngbya majuscula has afforded isomalyngamides A (785) and B (786) (857), isomeric with the known malyngamide A, and the previously unreported malyngamide B (787) (858). The novel pitiamide A (788) was isolated from... 

Cyanobacteria blooms can pose an extremely serious threat to human health (970-972), and some of the causative toxins contain halogen. The fresh water toxic cyanobacterium Oscillatoria agardhii produces oscillaginin A (916), which features the novel 3-amino-10-chloro-2-hydroxydecanoic acid, and is the source of the micro-cystins, which are heptatoxins (973). The prolific cyanobacterium Lyngbya majuscula from Curacao has furnished the novel barbamide (917) (974) and dechlorobarbamide (918) (975). Extensive biosynthetic studies show that the amino acids leucine, cysteine, and phenylalanine are involved in barbamide production (976-982). The chlorination of leucine is of great interest and may involve a radical mechanism (976, 980-983). 

This new metabolite belongs to the L-series of trichloroleucine peptides and is a rare example of a non-/V-methylated trichloroleucine amino acid (992). Another sample of this sponge from the same locale has yielded the new thiazoles 945 and 946, which are also related to dysidenin (993). The Panamanian Lyngbya majuscula has afforded the new dysidenamide (947), pseudodysidenin (948), and nordysidenin (949), which is the first report of dysidenin-like compounds from a free-living cyanobacterium (994). 

Osborne NJT, Webb PM, Shaw GR (2001) The Toxins of Lyngbya majuscula and Their Human and Ecological Health Effects. Environ Int 27 381... 

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