2020
DOI: 10.1021/acs.jnatprod.9b01181
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Chrysosporazines F–M: P-Glycoprotein Inhibitory Phenylpropanoid Piperazines from an Australian Marine Fish Derived Fungus, Chrysosporium sp. CMB-F294

Abstract: Chemical analysis of the fungus Chrysosporium sp. CMB-F294 isolated from the gastrointestinal tract of a market-purchased specimen of Mugil mullet yielded eight new alkaloids, belonging to a rare class of phenylpropanoid piperazines. Chrysosporazines F−M (1− 8) occur as an equilibrium mixture of acetamide rotamers and feature unprecedented carbocyclic and heterocyclic scaffolds. Structures inclusive of absolute configuration were assigned by detailed spectroscopic analysis, supported by biosynthetic considerat… Show more

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Cited by 21 publications
(26 citation statements)
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“…E. Fish: Chrysosporium sp. CMB-F294 isolated from the gastrointestinal tract of a Brisbane, Queensland, market-purchased fish, returned an new class of phenyl propanoid piperazine, including chrysosporazine F ( 11 ), exhibiting inhibitory activity against the multidrug efflux pump P-Glycoprotein with a potency > 2-fold that of the positive control verapamil ( Figure 2 ) [ 12 , 13 ].…”
Section: Microbial Diversitymentioning
confidence: 99%
“…E. Fish: Chrysosporium sp. CMB-F294 isolated from the gastrointestinal tract of a Brisbane, Queensland, market-purchased fish, returned an new class of phenyl propanoid piperazine, including chrysosporazine F ( 11 ), exhibiting inhibitory activity against the multidrug efflux pump P-Glycoprotein with a potency > 2-fold that of the positive control verapamil ( Figure 2 ) [ 12 , 13 ].…”
Section: Microbial Diversitymentioning
confidence: 99%
“…Antibacterial and antifungal assays were performed using prior published methods [ 24 , 25 , 26 ] as documented in the Supporting Information (Figure S37) .…”
Section: Methodsmentioning
confidence: 99%
“…The chrysosporazines were particular noteworthy, being non-cytotoxic to human carcinoma cells but exhibiting promising inhibitory activity against the multidrug resistance efflux pump P-glycoprotein (P-gp). For example, P-gp-overexpressing human colon carcinoma (SW620 Ad300) cells pre-treated with chrysosporazine F (2.5 µM) acquired a gain in sensitivity (GS 14) against the anticancer agent doxorubicin, >2-fold that of the positive control verapamil (GS 6.1), making chrysosporazine F one of the more potent P-gp inhibitors reported to date [5]. We now report a precursor-directed biosynthesis strategy where supplementation of a CMB-F214 M1 solid agar culture with sodium nicotinate enhanced production of otherwise inaccessible new natural products-namely azachrysposorazines A1 (1), A2 (2), B1 (3), C1 (4), C2 (5) and D1 (6), chrysosporazines N-P (7-9) and spirochrysosporazine A (10)-along with the known chrysosporazines A-D (11-14).…”
Section: Introductionmentioning
confidence: 99%
“…. Drugs 2021, 19, x FOR PEER REVIEW 2 o to date [5]. We now report a precursor-directed biosynthesis strategy where suppleme tation of a CMB-F214 M1 solid agar culture with sodium nicotinate enhanced producti of otherwise inaccessible new natural products-namely azachrysposorazines A1 (1), (2), B1 (3), C1 (4), C2 ( 5) and D1 (6), chrysosporazines N-P (7-9) and spirochrysosporaz A (10)-along with the known chrysosporazines A-D (11-14).…”
Section: Introductionmentioning
confidence: 99%
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