Three new andrastin derivatives from the endophytic fungus <i>Penicillium vulpinum</i>

Qin, Yu-Yue; Huang, Xishan; Liu, Xiaobo; Mo, Tu-Xiang; Xu, Zhao-Long; Li, Ben-Chao; Qin, Xiaoya; Li, Jun; Schäberle, Till F.; Yang, Ronghua

doi:10.1080/14786419.2020.1853725

Cited by 11 publications

(9 citation statements)

References 43 publications

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“…Compounds 224 and 227 displayed good activity against Bacillus megaterium (MIC value of 6.25 µg/mL), and compounds 225, 226, 228 showed average activity against Bacillus megaterium (MIC of 25, 12.5 and 25 µg/mL). Compound 226 showed potent antibacterial activity against B. paratyphosus B at 6.25 µg/mL, while the other compounds showed average activities against B. paratyphosus B at 12.5 or 25 µg/mL and compound 226 also exhibited moderate activities against E. coli and S. aureus with MIC values of 25 µg/mL [111]. A novel N-methoxy-1-pyridone alkaloid, chromenopyridin A (229), and the already reported compound viridicatol (230, Figure 13) were purified from Penicillium nothofagi P-6, residing inside the bark of Abies beshanzuensis.…”

Section: Penicilliummentioning

confidence: 99%

Fungal Endophytes: A Potential Source of Antibacterial Compounds

Deshmukh

Dufossé²,

Chhipa

et al. 2022

JoF

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Antibiotic resistance is becoming a burning issue due to the frequent use of antibiotics for curing common bacterial infections, indicating that we are running out of effective antibiotics. This has been more obvious during recent corona pandemics. Similarly, enhancement of antimicrobial resistance (AMR) is strengthening the pathogenicity and virulence of infectious microbes. Endophytes have shown expression of various new many bioactive compounds with significant biological activities. Specifically, in endophytic fungi, bioactive metabolites with unique skeletons have been identified which could be helpful in the prevention of increasing antimicrobial resistance. The major classes of metabolites reported include anthraquinone, sesquiterpenoid, chromone, xanthone, phenols, quinones, quinolone, piperazine, coumarins and cyclic peptides. In the present review, we reported 451 bioactive metabolites isolated from various groups of endophytic fungi from January 2015 to April 2021 along with their antibacterial profiling, chemical structures and mode of action. In addition, we also discussed various methods including epigenetic modifications, co-culture, and OSMAC to induce silent gene clusters for the production of noble bioactive compounds in endophytic fungi.

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Section: Penicilliummentioning

confidence: 99%

Fungal Endophytes: A Potential Source of Antibacterial Compounds

Deshmukh

Dufossé²,

Chhipa

et al. 2022

JoF

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“…Especially, hemiacetalmeroterpenoid A ( 1 ) was a new andrastin-type meroterpenoid containing a unique 6,6,6,6,5,5-hexa-cyclic skeleton. Meanwhile, eleven known compounds, including 3-deacetyl-citreohybridonol ( 4 ) [ 23 ] citreohybridone A ( 5 ) [ 24 ], 3,5-dimethylorsellinic acid-based meroterpenoid 2 ( 6 ) [ 5 ], andrastins A–C ( 7 , 10 , 13 ) [ 25 ], andrastone C ( 8 ) [ 26 ], penimeroterpenoid A ( 9 ) [ 4 ], 23-deoxocitreohybridonol ( 11 ) [ 1 ], 6α-hydroxyandrastin B ( 12 ) [ 1 ], and compound V ( 14 ) [ 27 ] were also obtained from the fungus N-5 ( Figure 1 ). All the isolated compounds were investigated for their antimicrobial activity against two phytopathogenic fungi and four bacterial strains.…”

Section: Introductionmentioning

confidence: 99%

“…Andrastins are meroterpenoids characterized by a 6,6,6,5-tetra-carbocyclic skeleton. They are biogenetically derived from 3,5-dimethylorsellinic acid (DMOA) and farnesyl diphosphate (FPP), synthesized via a mixed polyketide-terpenoid pathway, and usually possess a keto-enol tautomerism at the cyclopentane ring [ 1 , 2 , 3 , 4 ]. To date, over 40 andrastins have been reported with multiple potential biological activities, including cytotoxic [ 5 ], anti-inflammatory [ 6 ], antiproliferative [ 7 ] and antimicrobial activity [ 4 ].…”

Section: Introductionmentioning

confidence: 99%

“…They are biogenetically derived from 3,5-dimethylorsellinic acid (DMOA) and farnesyl diphosphate (FPP), synthesized via a mixed polyketide-terpenoid pathway, and usually possess a keto-enol tautomerism at the cyclopentane ring [ 1 , 2 , 3 , 4 ]. To date, over 40 andrastins have been reported with multiple potential biological activities, including cytotoxic [ 5 ], anti-inflammatory [ 6 ], antiproliferative [ 7 ] and antimicrobial activity [ 4 ]. The complex structures and potential biological activities of andrastins have attracted much attention in recent years [ 8 , 9 , 10 ].…”

Section: Introductionmentioning

confidence: 99%

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Hemiacetalmeroterpenoids A–C and Astellolide Q with Antimicrobial Activity from the Marine-Derived Fungus Penicillium sp. N-5

Chen

Yang

et al. 2022

Marine Drugs

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Four new compounds including three andrastin-type meroterpenoids hemiacetalmeroterpenoids A-C (1–3), and a drimane sesquiterpenoid astellolide Q (15), together with eleven known compounds (4–14) were isolated from the cultures of the marine-derived fungus Penicillium sp. N-5, while compound 14 was first isolated from a natural source. The structures of the new compounds were determined by analysis of detailed spectroscopic data, and the absolute configurations were further decided by a comparison of the experimental and calculated ECD spectra. Hemiacetalmeroterpenoid A (1) possesses a unique and highly congested 6,6,6,6,5,5-hexa-cyclic skeleton. Moreover, the absolute configuration of compound 14 was also reported for the first time. Compounds 1, 5 and 10 exhibited significant antimicrobial activities against Penicillium italicum and Colletrichum gloeosporioides with MIC values ranging from 1.56 to 6.25 μg/mL.

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“…Five recognised compounds were isolated from P. Claviforme in research, including cyclopeptin, m-hydroxybenzyl alcohol, isopatulin, 3-butyl-7-hydroxyphthalide, cyclopenine, and two new phthalides [ 20 ]. Similarly, three new andrastine derivatives from P. vulpinum have also been isolated and shown to have strong inhibitory activity [ 21 ].…”

Section: Introductionmentioning

confidence: 99%

Metabolic and pharmacological profiling of Penicillium claviforme by a combination of experimental and bioinformatic approaches

et al. 2022

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Background Penicillium produces a wide range of structurally diverse metabolites with significant pharmacological impacts in medicine and agriculture. For the first time, a complete metabolome of Penicillium claviforme ( P. claviforme ) (FBP-DNA-1205) was studied alongside pharmacological research in this study. Methods The metabolic profile of P. claviforme fermented on Potato Dextrose Broth (PDB) was investigated in this work. The complete metabolomics studies of fungus were performed using GC-MS and LC-MS-QTOF techniques. An in vitro model was utilised to study the cytotoxic and antioxidant activities, while an in vivo model was employed to investigate the antinociceptive and acute toxicity activities. Molecular Operating Environment (MOE) software was used for molecular docking analysis. Results GC-MS study showed the presence of alkanes, fatty acids, esters, azo and alcoholic compounds. Maculosin, obtain, phalluside, quinoline, 4,4’-diaminostilbene, funaltrexamine, amobarbital, and fraxetin were among the secondary metabolites identified using the LC-MS-QTOF technique. The n-hexane fraction of P. claviforme displayed significant cytotoxic activity in vitro , with an LD50 value of 92.22 µgml −1 . The antinociceptive effects in vivo were dose-dependent significantly ( p < .001). Interestingly, during the 72 h of investigation, no acute toxicity was demonstrated. In addition, a docking study of tentatively identified metabolites against the inflammatory enzyme (COX-2) supported the antinociceptive effect in an in silico model. Conclusion Metabolic profile of P. claviforme shows the presence of biologically relevant compounds in ethyl acetate extract. In addition, P. claviforme exhibits substantial antioxidant and cytotoxic activities in an in vitro model as well as antinociceptive activity in an in vivo model. The antinociceptive action is also supported by a molecular docking study. This research has opened up new possibilities in the disciplines of mycology, agriculture, and pharmaceutics. Key messages The first time explored complete metabolome through GC-MS and LC-MS-QTOF. Both in vivo & in vitro pharmacological investigation of P. claviforme . In silico molecular docking of LC-MS-QTOF metabolites.

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Three new andrastin derivatives from the endophytic fungus Penicillium vulpinum

Cited by 11 publications

References 43 publications

Fungal Endophytes: A Potential Source of Antibacterial Compounds

Fungal Endophytes: A Potential Source of Antibacterial Compounds

Hemiacetalmeroterpenoids A–C and Astellolide Q with Antimicrobial Activity from the Marine-Derived Fungus Penicillium sp. N-5

Metabolic and pharmacological profiling of Penicillium claviforme by a combination of experimental and bioinformatic approaches

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