Discovery of Acyl-Surugamide A2 from Marine Streptomyces albidoflavus RKJM-0023—A New Cyclic Nonribosomal Peptide Containing an N-ε-acetyl-L-lysine Residue

Maw, Zacharie A.; Haltli, Bradley; Guo, Jason J.; Baldisseri, Donna M.; Cartmell, Christopher; Kerr, Russell G.

doi:10.3390/molecules29071482

Cited by 3 publications

(2 citation statements)

References 58 publications

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“…no. NZ_CP133227.1) as well as supported by the isolation of a surugamide A analogue, acyl-surugamide A2 . Exposure to Rha led to the significant upregulation of a precursor ion with m / z 655.4378 (Dunn’s test control p -value 0.011, vehicle control p -value 0.022) (Figure S1) within the unknown cluster m / z 655.439, in which m / z 655.439 and 669.463 are the most abundant precursor ions (Figure ).…”

Section: Resultsmentioning

confidence: 81%

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Discovery of the Lipopeptides Albubactins A–H from Streptomyces albidoflavus RKJM0023 via Chemical Elicitation with Rhamnolipids and Synthesis of Albubactin A

Maw,

Grunwald,

Haltli

et al. 2024

J. Nat. Prod.

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The marine tunicate-derived Streptomyces albidoflavus RKJM0023 was cultured in the presence of a rhamnolipid mixture in an effort to elicit the production of silent natural products. MS/MS-based molecular networking analysis enhanced with nonparametric statistics highlighted the upregulation of a molecular cluster (Kruskal−Wallis p = 1.6 e −6 for 1) in which no MS/MS features had library matches. Targeted isolation of these features resulted in the discovery of nine new N-acylated lipopeptides, albubactins A−H (1−8) each containing a unique glutamine tripeptide and a C-terminal ethyl ester moiety. Three related albubactin acids A−C (9−11) lacking the ethyl ester were also identified. NMR spectroscopy and UPLC-HR-ESI-MS/MS demonstrated that the albubactins were obtained as mixtures that shared a common m/z and differed only in their acylated terminal groups. Due to the complex spectroscopic elucidation with many overlapping shifts, a total synthesis of albubactin A (1) was completed and used to determine the absolute configuration of the new albubactins.

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Section: Resultsmentioning

confidence: 81%

“…no. NZ_CP133228.1; 90910 bp) . The draft genome sequence was run through the Type Strain Genome Server and found that the RKJM0023 strain belongs to the known species S.…”

Section: Methodsmentioning

confidence: 99%

Discovery of the Lipopeptides Albubactins A–H from Streptomyces albidoflavus RKJM0023 via Chemical Elicitation with Rhamnolipids and Synthesis of Albubactin A

Maw,

Grunwald,

Haltli

et al. 2024

J. Nat. Prod.

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Synthesis and Cytotoxicity of Cyclic Octapeptide Surugamides with Varied <i>N</i>-Acyl Moieties

Matsuda,

Niikura,

Ichihara

et al. 2024

Chem. Pharm. Bull.

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Australian Marine and Terrestrial Streptomyces-Derived Surugamides, and Synthetic Analogs, and Their Ability to Inhibit Dirofilaria immitis (Heartworm) Motility

Wu,

Hussein,

Samarasekera

et al. 2024

Marine Drugs

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A bioassay-guided chemical investigation of a bacterium, Streptomyces sp. CMB-MRB032, isolated from sheep feces collected near Bathurst, Victoria, Australia, yielded the known polyketide antimycins A4a (1) and A2a (2) as potent inhibitors of Dirofilaria immitis (heartworm) microfilaria (mf) motility (EC50 0.0013–0.0021 µg/mL), along with the octapeptide surugamide A (3) and the new N-methylated analog surugamide K (4). With biological data suggesting surugamides may also exhibit activity against D. immitis, a GNPS molecular network analysis of a library of microbes sourced from geographically diverse Australian ecosystems identified a further five taxonomically and chemically distinct surugamide producers. Scaled-up cultivation of one such producer, Streptomyces sp. CMB-M0112 isolated from a marine sediment collected at Shorncliff, Qld, Australia, yielded 3 along with the new acyl-surugamides A1–A4 (5–8). Solid-phase peptide synthesis provided additional synthetic analogs, surugamides S1–S3 (9–11), while derivatization of 3 returned the semi-synthetic surugamide S4 (12) and acyl-surugamides AS1–AS3 (13–15). The natural acyl-surugamide A3 (7) and semi-synthetic acyl-surugamide AS3 (15) were shown to selectively inhibit D. immitis mf motility (EC50 3.3–3.4 µg/mL), however, unlike antimycins 1 and 2, were inactive against the gastrointestinal nematode Haemonchus contortus L1–L3 larvae (EC50 > 25 µg/mL) and were not cytotoxic to mammalian cells (human colorectal carcinoma SW620, IC50 > 30 µg/mL). A structure–activity relationship (SAR) study on the surugamides 3–15 revealed that selective acylation of the Lys3-ε-NH2 correlates with anthelmintic activity.

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Discovery of Acyl-Surugamide A2 from Marine Streptomyces albidoflavus RKJM-0023—A New Cyclic Nonribosomal Peptide Containing an N-ε-acetyl-L-lysine Residue

Cited by 3 publications

References 58 publications

Discovery of the Lipopeptides Albubactins A–H from Streptomyces albidoflavus RKJM0023 via Chemical Elicitation with Rhamnolipids and Synthesis of Albubactin A

Discovery of the Lipopeptides Albubactins A–H from Streptomyces albidoflavus RKJM0023 via Chemical Elicitation with Rhamnolipids and Synthesis of Albubactin A

Synthesis and Cytotoxicity of Cyclic Octapeptide Surugamides with Varied <i>N</i>-Acyl Moieties

Australian Marine and Terrestrial Streptomyces-Derived Surugamides, and Synthetic Analogs, and Their Ability to Inhibit Dirofilaria immitis (Heartworm) Motility

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