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Lyngbya majuscula

About: Lyngbya majuscula is a research topic. Over the lifetime, 333 publications have been published within this topic receiving 12835 citations.


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Journal ArticleDOI
TL;DR: A screening program for bioactive compounds from marine cyanobacteria led to the isolation of jamaicamides A-C, a novel and highly functionalized lipopeptide containing an alkynyl bromide, vinyl chloride, beta-methoxy eneone system, and pyrrolinone ring, giving insight into the mechanism by which this functional group is created.

459 citations

Journal ArticleDOI
TL;DR: Pure curacin A is an antimitotic agent that inhibits microtubule assembly and the binding of colchicine to tubulin and its unique thiazoline-containing structure has been deduced from spectroscopic information.
Abstract: Bioassay-guided fractionation of the organic extract of a Curacao collection of Lyngbya majuscula led to the isolation of a new lipid, curacin A, with exceptional brine shrimp toxic and antiproliferative activities. Its unique thiazoline-containing structure has been deduced from spectroscopic information. Pure curacin A is an antimitotic agent (IC 50 values in three cell lines ranging from 7 to 200 nM) that inhibits microtubule assembly and the binding of colchicine to tubulin

332 citations

Journal ArticleDOI
TL;DR: Apratoxin A (1), a potent cytotoxin with a novel skeleton, has been isolated from the marine cyanobacterium Lyngbya majuscula Harvey ex Gomont; however, it was only marginally active in vivo against a colon tumor and ineffective against a mammary tumor.
Abstract: Apratoxin A (1), a potent cytotoxin with a novel skeleton, has been isolated from the marine cyanobacterium Lyngbya majuscula Harvey ex Gomont. This cyclodepsipeptide of mixed peptide-polyketide biogenesis bears a thiazoline ring flanked by polyketide portions, one of which possesses an unusual methylation pattern. Its gross structure has been elucidated by spectral analysis, including various 2D NMR techniques. The absolute configurations of the amino acid-derived units were determined by chiral HPLC analysis of hydrolysis products. The relative stereochemistry of the new dihydroxylated fatty acid unit, 3,7-dihydroxy-2,5,8,8-tetramethylnonanoic acid, was elucidated by successful application of the J-based configuration analysis originally developed for acyclic organic compounds using carbon-proton spin-coupling constants ((2,3)J(C,H)) and proton-proton spin-coupling constants ((3)J(H,H)); its absolute stereochemistry was established by Mosher analysis. The conformation of 1 in solution was mimicked by molecular modeling, employing a combination of distance geometry and restrained molecular dynamics. Apratoxin A (1) possesses IC(50) values for in vitro cytotoxicity against human tumor cell lines ranging from 0.36 to 0.52 nM; however, it was only marginally active in vivo against a colon tumor and ineffective against a mammary tumor.

321 citations

Journal ArticleDOI
13 Apr 1979-Science
TL;DR: 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.
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.

294 citations

Journal ArticleDOI
TL;DR: The metabolic system is comprised of a nonribosomal peptide synthetase (NRPS) and multiple polyketide synthases (PKSs) and shows a very high level of collinearity between genes in the cluster and the predicted biochemical steps required for curacin biosynthesis.
Abstract: Curacin A (1) is a potent cancer cell toxin obtained from strains of the tropical marine cyanobacterium Lyngbya majuscula found in Curacao. Its structure is unique in that it contains the sequential positioning of a thiazoline and cyclopropyl ring, and it exerts its potent cell toxicity through interaction with the colchicine drug binding site on microtubules. A series of stable isotope-labeled precursors were fed to cultures of curacin A-producing strains and, following NMR analysis, allowed determination of the metabolic origin of all atoms in the natural product (one cysteine, 10 acetate units, two S-adenosyl methionine-derived methyl groups) as well as several unique mechanistic insights. Moreover, these incorporation experiments facilitated an effective gene cloning strategy that allowed identification and sequencing of the approximately 64 kb putative curacin A gene cluster. The metabolic system is comprised of a nonribosomal peptide synthetase (NRPS) and multiple polyketide synthases (PKSs) and shows a very high level of collinearity between genes in the cluster and the predicted biochemical steps required for curacin biosynthesis. Unique features of the cluster include (1) all but one of the PKSs are monomodular multifunctional proteins, (2) a unique gene cassette that contains an HMG-CoA synthase likely responsible for formation of the cyclopropyl ring, and (3) a terminating motif that is predicted to function in both product release and terminal dehydrative decarboxylation.

288 citations

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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
20211
20203
20195
20182
20173
20167