Cladodionen, a Cytotoxic Hybrid Polyketide from the Marine-Derived Cladosporium sp. OUCMDZ-1635

Zhu, Guoliang; Kong, Fan-Dong; Wang, Yi; Fu, Peng; Zhu, Weiming

doi:10.3390/md16020071

Cited by 35 publications

(52 citation statements)

References 23 publications

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“…Cladodionen was first isolated from marine fungus Cladosporium sp. OUCMDZ-1635, and had cytotoxic activities against a variety of human cancer cell lines [17]. Cladodionen belongs to cladosporiumins compounds which are composed of 2,4-pyrrolidinedione (tetramic acid) and a valine residue [17,19].…”

Section: Discussionmentioning

confidence: 99%

“…OUCMDZ-1635, and had cytotoxic activities against a variety of human cancer cell lines [17]. Cladodionen belongs to cladosporiumins compounds which are composed of 2,4-pyrrolidinedione (tetramic acid) and a valine residue [17,19]. The synthetic pathway of cladosporiumins includes polyketide synthase (PKS) and nonribosomal peptide synthase (NRPS) [19].…”

Section: Discussionmentioning

confidence: 99%

“…There was no difference in the growth dynamics of P. aeruginosa PAO1 between the control group and cladodionen-treated groups ranging from 100 µM to 400 µM. Figure S1,S2 and Table S1), the active compounds were identified as a pair of known isomers, cladodionen [17,18]. They were inseparable hybrid polyketide of two E/Z geometric isomers due to spontaneous and rapid isomerization between two forms ( Figure S3).…”

Section: Growth Curve Analysismentioning

confidence: 95%

“…The results showed that it afforded a baseline separation of two chromatographic peaks (60% MeOH/H 2 O), but HPLC techniques failed to separate these two components. Based on the electrospray ionization mass spectrometry (ESIMS m/z 234.1 [M + H] + ) and nuclear magnetic resonance (NMR) spectroscopic analyses (Figures S1, S2 and Table S1), the active compounds were identified as a pair of known isomers, cladodionen [17,18]. They were inseparable hybrid polyketide of two E/Z geometric isomers due to spontaneous and rapid isomerization between two forms ( Figure S3).…”

Section: Effects Of Cladodionen On the Production Of Virulence Factorsmentioning

confidence: 99%

“…Z148 with anti-QS activity from Jiaozhou Bay, China. The bioactive compound isolated from the secondary metabolites of this fungus was identified as cladodionen, a known natural product from Cladosporium and an inseparable hybrid polyketide of two E/Z geometric isomers [17][18][19]. The inhibitory effect of cladodionen on QS has not been reported; as such, the in vitro activity against QS systems of P. aeruginosa was evaluated in this study.…”

Section: Introductionmentioning

confidence: 99%

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Cladodionen Is a Potential Quorum Sensing Inhibitor Against Pseudomonas aeruginosa

Wang

Zhao

et al. 2020

Marine Drugs

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Pseudomonas aeruginosa is an opportunistic pathogen using virulence factors and biofilm regulated by quorum sensing (QS) systems to infect patients and protect itself from environmental stress and antibiotics. Interfering with QS systems is a novel approach to combat P. aeruginosa infections without killing the bacteria, meaning that it is much harder for bacteria to develop drug resistance. A marine fungus Cladosporium sp. Z148 with anti-QS activity was obtained from Jiaozhou Bay, China. Cladodionen, a novel QS inhibitor, was isolated from the extracts of this fungus. Cladodionen had a better inhibitory effect than pyocyanin on the production of elastase and rhamnolipid. It also inhibited biofilm formation and motilities. The mRNA expressions of QS-related genes, including receptor proteins (lasR, rhlR and pqsR), autoinducer synthases (lasI, rhlI and pqsA) and virulence factors (lasB and rhlA) were down-regulated by cladodionen. Molecular docking analysis showed that cladodionen had better binding affinity to LasR and PqsR than natural ligands. Moreover, the binding affinity of cladodionen to LasR was higher than to PqsR. Cladodionen exhibits potential as a QS inhibitor against P. aeruginosa, and its structure–activity relationships should be further studied to illustrate the mode of action, optimize its structure and improve anti-QS activity.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Growth Curve Analysismentioning

confidence: 95%

Section: Effects Of Cladodionen On the Production Of Virulence Factorsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Cladodionen Is a Potential Quorum Sensing Inhibitor Against Pseudomonas aeruginosa

Wang

Zhao

et al. 2020

Marine Drugs

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ECD exciton chirality method today: a modern tool for determining absolute configurations

Pescitelli

2021

Chirality

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The application of the exciton chirality method (ECM) to interpret electronic circular dichroism (ECD) spectra is a well-established and still popular approach to assign the absolute configuration (AC) of natural products, chiral organic compounds, and organometallic species. The method applies to compounds containing at least two chromophores with electric dipole allowed transitions (e.g., π-π* transitions). The exciton chirality rule correlates the sign of an exciton couplet (two ECD bands with opposite sign and similar intensity) with the overall molecular stereochemistry, including the AC. A correct application of the ECM requires three main prerequisites: (a) the knowledge of the molecular conformation, (b) the knowledge of the directions of the electric transition moments (TDMs), and (c) the assumption that the exciton coupling mechanism must be the major source of the observed ECD signals. All these prerequisites can be easily verified by means of quantum-mechanical (QM) calculations. In the present review, we shortly introduce the general principles that underpin the use of the ECM for configurational assignments and survey its applications, both classic ones and some reported in the recent literature. Based on these examples, we will stress the advantages of the ECM but also the key requisites for its correct application. Additionally, we will discuss the dependence of the couplet sign on geometrical parameters (angles α,β,γ between TDMs), which can be helpful for discerning the sign of exciton chirality in ambiguous situations. Finally, we will present a molecular orbital (MO) description of the exciton coupling phenomenon.

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Natural Bioactive Products from Marine Fungi Against Bacterial Infection

Minakshi,

Prakash,

Kumari

et al. 2024

Fungi Bioactive Metabolites

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Cladodionen, a Cytotoxic Hybrid Polyketide from the Marine-Derived Cladosporium sp. OUCMDZ-1635

Cited by 35 publications

References 23 publications

Cladodionen Is a Potential Quorum Sensing Inhibitor Against Pseudomonas aeruginosa

Cladodionen Is a Potential Quorum Sensing Inhibitor Against Pseudomonas aeruginosa

ECD exciton chirality method today: a modern tool for determining absolute configurations

Natural Bioactive Products from Marine Fungi Against Bacterial Infection

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