Ent-homocyclopiamine B, a Prenylated Indole Alkaloid of Biogenetic Interest from the Endophytic Fungus Penicillium concentricum

Ali, Tarig; Pham, Tiffany M.; Rakotondraibe, L. Harinantenaina

doi:10.3390/molecules24020218

Cited by 9 publications

(4 citation statements)

References 6 publications

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“…Recently, there have been several research efforts aimed at isolating and identifying antimicrobial compounds derived from Penicillium species. Three are certain compounds with antagonistic activity against plant pathogen species, including citrininand emodin derived from the fermentation of P. citrinum [32], and ent-homocyclopiamine B derived from P. concentricum [34]. Our data indicated that V. pyri mycelial growth and conidium germination were significantly reduced following treatment with ZZ1 culture filtrates.…”

Section: Discussionmentioning

confidence: 74%

Biological Control of Pear Valsa Canker Caused by Valsa pyri Using Penicillium citrinum

et al. 2021

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Valsa canker caused by Valsa pyri is one of the most destructive diseases of commercial pear. For the present analysis, 29 different endophytic fungal strains were isolated from the branches of a healthy pear tree. In dual culture assays, strain ZZ1 exhibited robust antifungal activity against all tested pathogens including Valsa pyri. Microscopic analyses suggested that following co-culture with ZZ1, the hyphae of V. pyri were ragged, thin, and ruptured. ZZ1 also induced significant decreases in lesion length and disease incidence on detached pear branches inoculated with V. pyri. ZZ1 isolate-derived culture filtrates also exhibited antifungal activity against V. pyri, decreasing mycelial growth and conidium germination and inhibiting V. pyri-associated lesion development on pear branches. These results suggest that the ZZ1 isolate has the potential for use as a biological control agent against V. pyri. The strain was further identified as Penicillium citrinum based on its morphological characteristics and molecular analyses. Overall, these data highlight a potentially valuable new biocontrol resource for combating pear Valsa canker.

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Section: Discussionmentioning

confidence: 74%

Biological Control of Pear Valsa Canker Caused by Valsa pyri Using Penicillium citrinum

et al. 2021

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“…The antibacterial properties of compounds from liverwort endophytes were studied by Ali et al, [ 63 ], who isolated a new prenylated indole alkaloid, ent -homocyclopiamine B ( 1 ), bearing an alicyclic nitro group along with 2-methylbutane-1,2,4-triol from the endophytic fungus Penicillium concentricum of the liverwort Trichocolea tomentella . The antibacterial activity of ent -homocyclopiamine B ( 1 ) was tested against a panel of Gram-positive and Gram-negative strains.…”

Section: Bioactive Natural Products From Bryendophytesmentioning

confidence: 99%

“…Subsequently, the broth microdilution assay revealed that the growth of B. subtilis ATCC 6633, Rhodococcus jhostii RHA1, and Corynebacterium glutamicum NRRL B-2784 was inhibited by 30% when treated with 100 µM of ent -homocyclopiamine B ( 1 ). This new compound only exhibited slight growth inhibition against selected Gram-positive strains, while all tested Gram-negative bacteria were not susceptible [ 63 ].…”

Section: Bioactive Natural Products From Bryendophytesmentioning

confidence: 99%

Bioactive Compounds Produced by Endophytic Microorganisms Associated with Bryophytes—The “Bryendophytes”

et al. 2023

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The mutualistic coexistence between the host and endophyte is diverse and complex, including host growth regulation, the exchange of substances like nutrients or biostimulants, and protection from microbial or herbivore attack. The latter is commonly associated with the production by endophytes of bioactive natural products, which also possess multiple activities, including antibacterial, insecticidal, antioxidant, antitumor, and antidiabetic properties, making them interesting and valuable model substances for future development into drugs. The endophytes of higher plants have been extensively studied, but there is a dearth of information on the biodiversity of endophytic microorganisms associated with bryophytes and, more importantly, their bioactive metabolites. For the first time, we name bryophyte endophytes “bryendophytes” to elaborate on this important and productive source of biota. In this review, we summarize the current knowledge on the diversity of compounds produced by endophytes, emphasizing bioactive molecules from bryendophytes. Moreover, the isolation methods and biodiversity of bryendophytes from mosses, liverworts, and hornworts are described.

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“…Over the past two decades, the genus Penicillium has been extensively investigated for its biological, agronomic, biotechnological and pharmacological potential [ 4 ]. Polyketides [ 5 , 6 ], alkaloids [ 7 , 8 ], terpenoids [ 9 , 10 ] and lactones [ 11 , 12 ] are among the structurally diverse metabolites discovered in Penicillium sp. These compounds exhibited a variety of biological properties, including anti-HIV [ 5 ], cytotoxic [ 9 , 10 ], antioxidant [ 13 ] and antibacterial [ 7 , 13–15 ].…”

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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Ent-homocyclopiamine B, a Prenylated Indole Alkaloid of Biogenetic Interest from the Endophytic Fungus Penicillium concentricum

Cited by 9 publications

References 6 publications

Biological Control of Pear Valsa Canker Caused by Valsa pyri Using Penicillium citrinum

Biological Control of Pear Valsa Canker Caused by Valsa pyri Using Penicillium citrinum

Bioactive Compounds Produced by Endophytic Microorganisms Associated with Bryophytes—The “Bryendophytes”

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

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