Clonostachysins A and B, New Anti-dinoflagellate Cyclic Peptides from a Marine-derived Fungus

Adachi, Kyoko; Kanoh, Kaneo; Wisespongp, Puntip; Nishijima, Miyuki; Shizuri, Yoshikazu

doi:10.1038/ja.2005.17

Cited by 32 publications

(16 citation statements)

References 10 publications

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“…Both clonostachysins A ( 228 ) and B ( 229 ) were obtained from a marine sponge-derived fungus Clonostachys rogersoniana strain HJK9. They exhibited a selectively inhibitory activity on the dinoflagellate Prorocentrum micans at 30 μM [ 170 ]. Cylindrocyclin A ( 230 ) from Cylindrocarpon sp.…”

Section: Cyclic Nonapeptidesmentioning

confidence: 99%

Structural Diversity and Biological Activities of Fungal Cyclic Peptides, Excluding Cyclodipeptides

Wang

Lin

et al. 2017

Molecules

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Cyclic peptides are cyclic compounds formed mainly by the amide bonds between either proteinogenic or non-proteinogenic amino acids. This review highlights the occurrence, structures and biological activities of fungal cyclic peptides (excluding cyclodipeptides, and peptides containing ester bonds in the core ring) reported until August 2017. About 293 cyclic peptides belonging to the groups of cyclic tri-, tetra-, penta-, hexa-, hepta-, octa-, nona-, deca-, undeca-, dodeca-, tetradeca-, and octadecapeptides as well as cyclic peptides containing ether bonds in the core ring have been isolated from fungi. They were mainly isolated from the genera Aspergillus, Penicillium, Fusarium, Acremonium and Amanita. Some of them were screened to have antimicrobial, antiviral, cytotoxic, phytotoxic, insecticidal, nematicidal, immunosuppressive and enzyme-inhibitory activities to show their potential applications. Some fungal cyclic peptides such as the echinocandins, pneumocandins and cyclosporin A have been developed as pharmaceuticals.

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Section: Cyclic Nonapeptidesmentioning

confidence: 99%

Structural Diversity and Biological Activities of Fungal Cyclic Peptides, Excluding Cyclodipeptides

Wang

Lin

et al. 2017

Molecules

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“…Cyclooligopeptides, especially medium ring-sized peptides bearing aliphatic amino acid units, have been reported from diverse marine sources, including marine microorganisms [1–5]. These cyclic congeners derived from marine microorganisms exhibit a range of pharmacological activities, including antimicrobial activity [6], cytotoxicity [7,8], anti-dinoflagellate activity [9] and inhibitory activity against enzyme sortase B [10]. A natural cyclotetrapeptide cyclo -(isoleucyl-prolyl-leucyl- alanyl) has been isolated from the marine bacteria Pseudomonas sp.…”

Section: Introductionmentioning

confidence: 99%

Toward the Synthesis and Biological Screening of a Cyclotetrapeptide from Marine Bacteria

Dahiya¹,

Gautam²

2010

Marine Drugs

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The first synthesis of a naturally occurring tetrapeptide cyclo-(isoleucyl-prolyl-leucyl- alanyl) has been achieved using a solution-phase technique via coupling of dipeptide segments Boc-l-Pro-l-Leu-OH and l-Ala-l-Ile-OMe. Deprotection of the linear tetrapeptide unit and its subsequent cyclization gave a cyclopeptide, identical in all aspects to the naturally occurring compound. Bioactivity results indicated the antifungal and antihelmintic potential of the synthesized peptide against pathogenic dermatophytes and earthworms.

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“…IB-01212 was isolated from the mycelium extract of the marine fungus Clonostachys pytirodes. [24,25]…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structure–Activity Relationship of Cytotoxic Marine Cyclodepsipeptide IB‐01212 Analogues

et al. 2007

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Several recently discovered marine products have remarkable in vitro and in vivo anticancer profiles against a wide range of tumor cell lines. Some of these compounds are currently in clinical trials. These compounds show complex structures and mechanisms of action of interest. Herein, we describe the preparation of a series of totally synthetic molecules that are structurally related to the natural marine product IB‐01212 and evaluated them as antitumor agents. For this, total solid‐phase syntheses of the products were performed in parallel by two distinct routes: linear synthesis and convergent synthesis. Structural modifications were introduced in several residue positions to afford 21 IB‐01212 analogues for structure–relationship studies. An increase in the number of methyl groups in the macrocycle enhanced cytotoxic activity. Also, the replacement of an ester bond by an amide bond favored antitumor activity against several human cell lines. In addition, the L configuration analogues were more active against all the tumor cell lines than those containing the D configuration. A significant increase in the size and asymmetry of the macrocycle diminished biological activity with respect to that of IB‐01212. These results are of great value for the discovery of new and more effective anticancer agents.

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Clonostachysins A and B, New Anti-dinoflagellate Cyclic Peptides from a Marine-derived Fungus

Cited by 32 publications

References 10 publications

Structural Diversity and Biological Activities of Fungal Cyclic Peptides, Excluding Cyclodipeptides

Structural Diversity and Biological Activities of Fungal Cyclic Peptides, Excluding Cyclodipeptides

Toward the Synthesis and Biological Screening of a Cyclotetrapeptide from Marine Bacteria

Synthesis and Structure–Activity Relationship of Cytotoxic Marine Cyclodepsipeptide IB‐01212 Analogues

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