Lyngbyacyclamides A and B, novel cytotoxic peptides from marine cyanobacteria Lyngbya sp.

Maru, Norihito; Ohno, Osamu; Uemura, Daisuke

doi:10.1016/j.tetlet.2010.06.105

Cited by 41 publications

(44 citation statements)

References 6 publications

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“…In contrast, lobocyclamides were isolated from a marine Lyngbya confervoides , 13 and lyngbyacyclamides were isolated from a marine Lyngbya sp. 21 These strains as well as UIC 10045 belong to the order of Oscillatoriales . The presence of these structurally related secondary metabolites in both orders Notocales and Oscillatoriales , as well as their broad distributions among marine, terrestrial and freshwater environments, hints a possible important ecological function of this class of compounds.…”

Section: Resultsmentioning

confidence: 99%

Trichormamides C and D, antiproliferative cyclic lipopeptides from the cultured freshwater cyanobacterium cf. Oscillatoria sp. UIC 10045

Luo

Kang

Krunić

et al. 2015

Bioorganic & Medicinal Chemistry

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Extract from the cultured freshwater cf. Oscillatoria sp. UIC 10045 showed antiproliferative activity against HT-29 cell line. Bioassay-guided fractionation led to the isolation of two new cyclic lipopeptides, named trichormamides C (1) and D (2). The planar structures were determined by combined analyses of HRESIMS, Q-TOF ESIMS/MS, and 1D and 2D NMR spectra. The absolute configurations of the amino acid residues were assigned by the advanced Marfey’s analysis after partial and complete acid hydrolysis. Trichormamides C (1) is a cyclic undecapeptide and D (2) is a cyclic dodecapeptide, both containing a lipophilic β-aminodecanoic acid residue. Trichormamide C (1) displayed antiproliferative activities against HT-29 and MDA-MB-435 cancer cell lines with IC50 values of 1.7 and 1.0 µM, respectively, as well as anti-Mycobacterium tuberculosis activity with MIC value of 23.8 µg/mL (17.3 µM). Trichormamide D (2) was found to be less potent against both HT-29 and MDA-MB-435 cancer cell lines with IC50 values of 11.5 and 11.7 µM, respectively.

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Section: Resultsmentioning

confidence: 99%

Trichormamides C and D, antiproliferative cyclic lipopeptides from the cultured freshwater cyanobacterium cf. Oscillatoria sp. UIC 10045

Luo

Kang

Krunić

et al. 2015

Bioorganic & Medicinal Chemistry

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“…Cyclic lipopeptides are common among the cyanobacterial natural products and typically contain a single fatty acid as in laxaphycins (Galica et al, 2017) that confers membrane-disruptive properties (Humisto et al, 2019). Laxaphycin family peptides have been shown to be toxic to or inhibit the growth of multiple organisms and cell lines (Gerwick et al, 1989; Frankmölle et al, 1992b; Bonnard et al, 1997; MacMillan et al, 2002; Bonnard et al, 2007; Maru et al, 2010; Luo et al, 2014; Luo et al, 2015; Dussault et al, 2016; Cai et al, 2018; Bornancin et al, 2019). We observed antifungal activity of scytocyclamides towards A. flavus (Figure3, Table S3).…”

Section: Discussionmentioning

confidence: 99%

Shared PKS modules in biosynthesis of synergistic laxaphycins

Heinilä

Fewer

Jokela

et al. 2020

Preprint

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Cyanobacteria produce a wide range of lipopeptides that exhibit potent membrane-disrupting 1 5activities. Laxaphycins consist of two families of structurally distinct macrocyclic lipopeptides that 1 6act in a synergistic manner to produce antifungal and antiproliferative activities. Laxaphycins are 1 7 produced by range of cyanobacteria but their biosynthetic origins remain unclear. Here, we 1 8identified the biosynthetic pathways responsible for the biosynthesis of the laxaphycins produced 1 9

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“…The last exemplars are the lyngbyacyclamides A and B, isolated from Lynbya sp. collected at Ishigaki Island in Japan (Maru, Ohno, and Uemura, 2010), and the scytocyclamides A, B and C, extracted from the cultivated fresh water Scytonema hofmanni PCC7110. Lyngbyacyclamide A contains a Pro 10 replaced in the B form by (2 S,4R)-Hyp 10 and are [(2S-Hse 4 ), (3R-Phe)] laxaphycin B 3 analog, but contrary to the previous studies the stereochemistry of nonproteinogenic amino acids was not determined.…”

Section: Laxaphycins and Their Derivatives: Peptides Not So Easy To Smentioning

confidence: 99%

“…The ecological role of laxaphycins remains especially unclear, with conflicting results having been reported. For example, when lyngyacyclamides or hormothamnin A were tested on the brine shrimp Artemia, they failed to show any activity at doses of 70 mM, whereas scytocyclamides A and B were lethal in less than 2 h for the freshwater crustacean Thamnocephalus platyrus, with LD 50 -values of 18 mM and 3.7 mM, respectively (Maru, Ohno, and Uemura, 2010;Grewe, 2005). Therefore, the commonly proposed use of these peptides as chemical defenses could not be confirmed.…”

Section: Laxaphycins and Their Derivatives: Peptides Not So Easy To Smentioning

confidence: 99%

Marine Peptide Secondary Metabolites

Banaigs

Bonnard

Witczak

et al. 2014

Outstanding Marine Molecules

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A large pro port ion of the marine natural produc ts actu ally u n der clinical inve stigat ion are pept ide sec ondary metabolites with unusual amino acids re sidues. This growing f amily of compounds can be produced via tw o major p athw ays, r ibosomal and nonribosomal. In this c hapt er a re p re sent ed a nd illu strated, with a fe w f amou s examples, ribosomal-and n onribosomal-d erived pe ptides. Atte ntion is focused on fi ve families of biological ly a ctive marine p eptides of d iverse origin, ranging from the old est living ce ll of the world, the cyanobact eria, to more sophisticat ed organisms s uch a s tu nicates or mol lusk s. T he discu ssed pe ptides illu strate d iff erently th e s tructural fe atu re s and diversity f ound in mari ne-derived peptid es; laxaphycins as an example o f true pept ide s; dolast atins, didemnins and kahalalides are discuss ed in connectio n wit h their cl inical trials; a nd azole/azoli ne-c ontaining cyanobactins to exe m plif y the extra ord ina ry c hemi cal dive rs it y wit hin a single organism. Information abou t their biol ogical properties and mec hanisms of a ctio n is disc uss ed when available .

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Lyngbyacyclamides A and B, novel cytotoxic peptides from marine cyanobacteria Lyngbya sp.

Cited by 41 publications

References 6 publications

Trichormamides C and D, antiproliferative cyclic lipopeptides from the cultured freshwater cyanobacterium cf. Oscillatoria sp. UIC 10045

Trichormamides C and D, antiproliferative cyclic lipopeptides from the cultured freshwater cyanobacterium cf. Oscillatoria sp. UIC 10045

Shared PKS modules in biosynthesis of synergistic laxaphycins

Marine Peptide Secondary Metabolites

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