Identification and bioactivity evaluation of secondary metabolites from Antarctic-derived <i>Penicillium chrysogenum</i> CCTCC M 2020019

Khan, Imran; Zhang, Hai-Bo; Liu, Wei; Zhang, Liping; Peng, Fang; Chen, Yuchan; Zhang, Qingbo; Zhang, Guangtao; Zhang, Weiyang

doi:10.1039/d0ra03529g

Cited by 16 publications

(12 citation statements)

References 44 publications

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“…6 ). Similar to [2− 13 C]- 6 that exhibits two peaks ( δ = 56.8 and 61.2 ppm) representing two tautomers in the solution state, 12 shows two peaks at 120 and 124 ppm 41 . The third peak ( δ = 119 ppm) most likely originates from the other stereoisomer with the cis -geometry of the double bond.…”

Section: Resultsmentioning

confidence: 88%

Elucidation of divergent desaturation pathways in the formation of vinyl isonitrile and isocyanoacrylate

et al. 2022

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Two different types of desaturations are employed by iron- and 2-oxoglutarate-dependent (Fe/2OG) enzymes to construct vinyl isonitrile and isocyanoacrylate moieties found in isonitrile-containing natural products. A substrate-bound protein structure reveals a plausible strategy to affect desaturation and hints at substrate promiscuity of these enzymes. Analogs are synthesized and used as mechanistic probes to validate structural observations. Instead of proceeding through hydroxylated intermediate as previously proposed, a plausible carbocation species is utilized to trigger C=C bond installation. These Fe/2OG enzymes can also accommodate analogs with opposite chirality and different functional groups including isonitrile-(D)-tyrosine, N-formyl tyrosine, and phloretic acid, while maintaining the reaction selectivity.

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Section: Resultsmentioning

confidence: 88%

Elucidation of divergent desaturation pathways in the formation of vinyl isonitrile and isocyanoacrylate

et al. 2022

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“…A series of metabolites, including xanthocillin Y1 ( 3 ), were isolated from an Antarctic derived Penicillium chrysogenum strain, with xanthocillin X ( 1 ) displaying dominant activity with a titer of 0.9 g/L (Table ). These two compounds demonstrated significant cytotoxicity on four cancer cell lines, as well as antibacterial activity against Gram-negative bacteria ( Pseudomonas aeruginosa , Acinetobacter baumannii , and Klebsiella pneumonie ) with a MIC of 0.125 μg/mL …”

Section: Isocyano Group In Natural Productsmentioning

confidence: 99%

“…These two compounds demonstrated significant cytotoxicity on four cancer cell lines, as well as antibacterial activity against Gram-negative bacteria (Pseudomonas aeruginosa, Acinetobacter baumannii, and Klebsiella pneumonie) with a MIC of 0.125 μg/mL. 96 Xanthocillin X monomethyl ether (25) was isolated from the fungus Dichotomyces albus. 97 This compound displayed wide antibacterial activity against Gram-positive and negative bacteria as well as against certain fungi.…”

Section: Isocyanides In Fungi and Their Biological Activitymentioning

confidence: 99%

Medicinal Chemistry of Isocyanides

et al. 2021

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In eons of evolution, isocyanides carved out a niche in the ecological systems probably thanks to their metal coordinating properties. In 1859 the first isocyanide was synthesized by humans and in 1950 the first natural isocyanide was discovered. Now, at the beginning of XXI century, hundreds of isocyanides have been isolated both in prokaryotes and eukaryotes and thousands have been synthesized in the laboratory. For some of them their ecological role is known, and their potent biological activity as antibacterial, antifungal, antimalarial, antifouling, and antitumoral compounds has been described. Notwithstanding, the isocyanides have not gained a good reputation among medicinal chemists who have erroneously considered them either too reactive or metabolically unstable, and this has restricted their main use to technical applications as ligands in coordination chemistry. The aim of this review is therefore to show the richness in biological activity of the isocyanidecontaining molecules, to support the idea of using the isocyanide functional group as an unconventional pharmacophore especially useful as a metal coordinating warhead. The unhidden hope is to convince the skeptical medicinal chemists of the isocyanide potential in many areas of drug discovery and considering them in the design of future drugs.

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“…The known compounds 33 ~ 34 ( Figure 4 ) possessing diisocyanobuta-1,3-diene were re-isolated by Zhang group from Antarctic-derived Penicillium chrysogenum CCTCC M 2020019, and both compounds exhibited broad anti-bacterial activities [ 47 ]. Compound 33 has a MIC value of 0.125 μg/mL against P. aeruginosa , whereas the appendence of OH group (compound 34 ) decreased the anti-microbial activity obviously (MIC value of 8 μg/mL).…”

Section: Emerging Mnps As Promising Antibiotics For Inhibiting ...mentioning

confidence: 99%

“…Compound 33 has a MIC value of 0.125 μg/mL against P. aeruginosa , whereas the appendence of OH group (compound 34 ) decreased the anti-microbial activity obviously (MIC value of 8 μg/mL). Meanwhile, both compounds were cytotoxic to cancer cell lines SF-268, MCF-7, HepG-2 and A549 with the IC 50 values ranging from 0.26 to 5.04 μM [ 47 ].…”

Section: Emerging Mnps As Promising Antibiotics For Inhibiting ...mentioning

confidence: 99%

Discovery of Marine Natural Products as Promising Antibiotics against Pseudomonas aeruginosa

Maimaitiming

Zhou

et al. 2022

Marine Drugs

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Pseudomonas aeruginosa, one of the most intractable Gram-negative bacteria, has become a public health threat due to its outer polysaccharide layer, efflux transporter system, and high level of biofilm formation, all of which contribute to multi-drug resistance. Even though it is a pathogen of the highest concern, the status of the antibiotic development pipeline is unsatisfactory. In this review, we summarize marine natural products (MNPs) isolated from marine plants, animals, and microorganisms which possess unique structures and promising antibiotic activities against P. aeruginosa. In the last decade, nearly 80 such MNPs, ranging from polyketides to alkaloids, peptides, and terpenoids, have been discovered. Representative compounds exhibited impressive in vitro anti-P. aeruginosa activities with MIC values in the single-digit nanomolar range and in vivo efficacy in infectious mouse models. For some of the compounds, the preliminary structure-activity-relationship (SAR) and anti-bacterial mechanisms of selected compounds were introduced. Compounds that can disrupt biofilm formation or membrane integrity displayed potent inhibition of multi-resistant clinical P. aeruginosa isolates and could be considered as lead compounds for future development. Challenges on how to translate hits into useful candidates for clinical development are also proposed and discussed.

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Identification and bioactivity evaluation of secondary metabolites from Antarctic-derived Penicillium chrysogenum CCTCC M 2020019

Abstract: The unprecedented eight-membered heterocyclic chrysonin (1) was isolated from an Antarctic fungus that also produced xanthocillins 4 and 5 as potent inhibitors against Gram-negative pathogens.

Cited by 16 publications

References 44 publications

Elucidation of divergent desaturation pathways in the formation of vinyl isonitrile and isocyanoacrylate

Elucidation of divergent desaturation pathways in the formation of vinyl isonitrile and isocyanoacrylate

Medicinal Chemistry of Isocyanides

Discovery of Marine Natural Products as Promising Antibiotics against Pseudomonas aeruginosa

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