Lyngbyapeptin A, a modified tetrapeptide from Lyngbya bouillonii (Cyanophyceae)

Klein, D.; Braekman, Jean Claude; Daloze, Désiré; Hoffmann, Lucien; Castillo, Gabriel; Demoulin, V.

doi:10.1016/s0040-4039(98)02451-4

Cited by 42 publications

(31 citation statements)

References 4 publications

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“…The absolute configuration of 7a (and thus indirectly of 7 ) was established using enantioselective HPLC-MS analysis following ozonolysis, oxidative workup, and acid hydrolysis. Peaks corresponding to N -Me- l -Val, N -Me- l -Asp (from degradation of N,O -diMe- l -Tyr), N -Me- l -Leu, and l -Pro were detected, indicating the all- S configuration as in lyngbyapeptins A–C 6,22,24…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic Halogenated Macrolides and Modified Peptides from the Apratoxin-Producing Marine Cyanobacterium Lyngbya bouillonii from Guam

et al. 2010

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Collections of the marine cyanobacterium Lyngbya bouillonii from shallow patch reefs in Apra Harbor, Guam, afforded three hitherto undescribed analogues of the glycosidic macrolide lyngbyaloside, namely 2-epi-lyngbyaloside (1) and the regioisomeric 18E-and 18Z-lyngbyalosides C (2 and 3). Concurrently we discovered two new analogues of the cytoskeletal actin-disrupting lyngbyabellins, 27-deoxylyngbyabellin A (4) and lyngbyabellin J (5), a novel macrolide of the laingolide family, laingolide B (6), and a linear modified peptide, lyngbyapeptin D (7), along with known lyngbyabellins A and B, lyngbyapeptin A, and lyngbyaloside. The structures of 1-7 were elucidated by a combination of NMR spectroscopic and mass spectrometric analysis. Compounds 1-6 were either brominated (1-3) or chlorinated (4-6), consistent with halogenation being a hallmark of many marine natural products. All extracts derived from these L. bouillonii collections were highly cytotoxic due to the presence of apratoxin A or also apratoxin C. Compounds 1-5 showed weak to moderate cytotoxicity to HT29 colorectal adenocarcinoma and HeLa cervical carcinoma cells.Marine cyanobacteria have been attracting increasing attention for probe and drug discovery due to the high incidence of structurally novel bioactive secondary metabolites that complement those known from terrestrial sources. These natural products are predominantly modified peptides and depsipeptides, polyketides and peptide-polyketide hybrids, many of which are cyclic and oftentimes halogenated.1 One intriguing characteristic of marine cyanobacteria is that a single organism commonly produces several distinct classes of natural products so that up to 10% of the genome may be dedicated to secondary metabolism. One example of such a "superproducer" is Lyngbya bouillonii.2 , 3 Various collections carried out over the past two decades have consistently yielded apratoxin A,4 lyngbyabellin A,5 lyngbyapeptin A6 and, with variable reproducibility, also lyngbyastatin 2,7 , 8 lyngbyabellin B,6 apratoxin B9 and apramides A-G.10 Recently we found that the secondary metabolite content of L. bouillonii may be depth-dependent, because at the same site (Finger's Reef, Guam) but at greater depth (14 m instead of 2 m) apratoxin E rather than apratoxin A was the major apratoxin produced by a morphologically identical * To whom correspondence should be addressed. Tel.: (352) Fax: (352) 273-7741, luesch@cop.ufl.edu. ‡ Contributed equally.Supporting Information Available: NMR spectra for compounds 1-7. This material is available free of charge via the Internet at http://pubs.acs.org. NIH Public AccessAuthor Manuscript J Nat Prod. Author manuscript; available in PMC 2011 September 24. NIH-PA Author ManuscriptNIH-PA Author Manuscript NIH-PA Author Manuscript cyanobacterium.8 The latter, however, lacked the usually co-existing snapping shrimp Alpheus frontalis that is known to use L. bouillonii as food and tubular shelter.11 -13Previous investigations of L. bouillonii from Finger's Reef in Apra Harbor we...

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Section: Resultsmentioning

confidence: 99%

Cytotoxic Halogenated Macrolides and Modified Peptides from the Apratoxin-Producing Marine Cyanobacterium Lyngbya bouillonii from Guam

et al. 2010

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“…Since the latter has only been isolated in trace amounts and decomposed during structure elucidation it has been described without assignment of the configuration at the double bond. [18] The combination of at least four different, overlapping UV chromophores within the ajudazols prevents the use of optical methods for the direct determination of their absolute configuration. …”

Section: Resultsmentioning

confidence: 99%

The Ajudazols A and B, Novel Isochromanones fromChondromyces crocatus (Myxobacteria): Isolation and Structure Elucidation

et al. 2002

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“…Most of the organic matter produced from photosynthetic CO 2 fixation is liberated in the sediment and degraded by chemotrophic microorganisms, among which SRB are particularly prominent. Cyanobacteria contain N-methyl transferase (NMT) and ortho-methyl transferase (O-methylation) domains in their metabolism, responsible for the formation of compounds such as methylcobalanate, methylmalonate and other bi-methyl and even tri-methyl compounds (Klein et al, 1999;Luesch et al, 2000). These compounds may be available for the synthesis of MeHg from cyanobacteria cellular lysis, cellular exudates and decomposition of its mucilage sheath.…”

Section: Linear Modelsmentioning

confidence: 99%

Cyanobacteria enhance methylmercury production: A hypothesis tested in the periphyton of two lakes in the Pantanal floodplain, Brazil

Lázaro

Guimarães

Ignácio

et al. 2013

Science of The Total Environment

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Lyngbyapeptin A, a modified tetrapeptide from Lyngbya bouillonii (Cyanophyceae)

Cited by 42 publications

References 4 publications

Cytotoxic Halogenated Macrolides and Modified Peptides from the Apratoxin-Producing Marine Cyanobacterium Lyngbya bouillonii from Guam

Cytotoxic Halogenated Macrolides and Modified Peptides from the Apratoxin-Producing Marine Cyanobacterium Lyngbya bouillonii from Guam

The Ajudazols A and B, Novel Isochromanones fromChondromyces crocatus (Myxobacteria): Isolation and Structure Elucidation

Cyanobacteria enhance methylmercury production: A hypothesis tested in the periphyton of two lakes in the Pantanal floodplain, Brazil

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