Phenalenones from a Marine-Derived Fungus Penicillium sp.

Park, Sung Chul; Julianti, Elin; Ahn, Soon Kil; Kim, Donghwa; Lee, Sang Kook; Noh, Minsoo; Oh, Dong‐Chan; Oh, Ki‐Bong; Shin, And Jongheon

doi:10.3390/md17030176

Cited by 17 publications

(22 citation statements)

References 29 publications

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“…However, the obtained rotations were severely irregular and resulted in alternating signs, possibly due to the presence of significantly different conformers ( Supplementary Figures S40–S43 ) [ 30 , 31 ]. Notable examples of this phenomenon among marine natural products would be the sponge-derived discorhabdins, fungus-derived herqueinones, and ascidian-derived isocadiolides [ 32 , 33 , 34 , 35 , 36 ]. This problem was solved by the ECD measurements.…”

Section: Resultsmentioning

confidence: 99%

Bioactive Bis(indole) Alkaloids from a Spongosorites sp. Sponge

et al. 2020

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Six new bis(indole) alkaloids (1–6) along with eight known ones of the topsentin class were isolated from a Spongosorites sp. sponge of Korea. Based on the results of combined spectroscopic analyses, the structures of spongosoritins A–D (1–4) were determined to possess a 2-methoxy-1-imidazole-5-one core connecting the indole moieties, and these were linked by a linear urea bridge for spongocarbamides A (5) and B (6). The absolute configurations of spongosoritins were assigned by electronic circular dichroism (ECD) computation. The new compounds exhibited moderate inhibition against transpeptidase sortase A and weak inhibition against human pathogenic bacteria and A549 and K562 cancer cell lines.

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Section: Resultsmentioning

confidence: 99%

Bioactive Bis(indole) Alkaloids from a Spongosorites sp. Sponge

et al. 2020

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“…Finally, subfraction A423 (56.1 mg) was further purified by semi-preparative HPLC (75% MeOH) to furnish ent -peniciherquinone ( t R 35.5 min, 0.5 mg). The structure of ent -peniciherquinone (EPQ, Figure 1 A) was identified by comparing their physical and NMR spectroscopic data with those reported in the literature [ 28 ] and determined using LC/MS analysis.…”

Section: Methodsmentioning

confidence: 99%

“…LC/MS-guided chemical analysis of a MeOH extract of P. herquei FT729 resulted in the isolation of a phenalenone derivative through successive column chromatography with preparative and semi-preparative HPLC. The isolated compound was structurally elucidated as ent -peniciherqueinone (EPQ), based on the NMR spectroscopic data [ 28 ] and LC/MS analysis. EPQ is a bioactive compound with anti-inflammatory, anti-angiogenic, and adipogenesis-inducing properties [ 28 ].…”

Section: Introductionmentioning

confidence: 99%

“…The isolated compound was structurally elucidated as ent -peniciherqueinone (EPQ), based on the NMR spectroscopic data [ 28 ] and LC/MS analysis. EPQ is a bioactive compound with anti-inflammatory, anti-angiogenic, and adipogenesis-inducing properties [ 28 ]. In this study, we investigated whether EPQ can confer protection against acetaldehyde-induced cytotoxicity and oxidative damage in PC12 cells.…”

Section: Introductionmentioning

confidence: 99%

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Ent-Peniciherqueinone Suppresses Acetaldehyde-Induced Cytotoxicity and Oxidative Stress by Inducing ALDH and Suppressing MAPK Signaling

Kwon

et al. 2020

Pharmaceutics

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Studies on ethanol-induced stress and acetaldehyde toxicity are actively being conducted, owing to an increase in alcohol consumption in modern society. In this study, ent-peniciherqueinone (EPQ) isolated from a Hawaiian volcanic soil-associated fungus Penicillium herquei FT729 was found to reduce the acetaldehyde-induced cytotoxicity and oxidative stress in PC12 cells. EPQ increased cell viability in the presence of acetaldehyde-induced cytotoxicity in PC12 cells. In addition, EPQ reduced cellular reactive oxygen species (ROS) levels and restored acetaldehyde-mediated disruption of mitochondrial membrane potential. Western blot analyses revealed that EPQ treatment increased protein levels of ROS-scavenging heme oxygenase-1 and superoxide dismutase, as well as the levels of aldehyde dehydrogenase (ALDH) 1, ALDH2, and ALDH3, under acetaldehyde-induced cellular stress. Finally, EPQ reduced acetaldehyde-induced phosphorylation of p38 and c-Jun N-terminal kinase, which are associated with ROS-induced oxidative stress. Therefore, our results demonstrated that EPQ prevents cellular oxidative stress caused by acetaldehyde and functions as a potent agent to suppress hangover symptoms and alcohol-related stress.

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“…New phenalenone derivatives ent -peniciherqueinone ( 241 ) and 4-hydroxysclerodin ( 242 ), along with known compounds ( 243 – 244 ) of the herqueinone class, were isolated from Penicillium sp. (Gagudo, South Korea) [ 133 ]. 4-Hydroxysclerodin ( 242 ) exhibited moderate anti-angiogenetic and anti-inflammatory activities.…”

Section: Other Activitiesmentioning

confidence: 99%

Metabolites of Marine Sediment-Derived Fungi: Actual Trends of Biological Activity Studies

2021

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Marine sediments are characterized by intense degradation of sedimenting organic matter in the water column and near surface sediments, combined with characteristically low temperatures and elevated pressures. Fungi are less represented in the microbial communities of sediments than bacteria and archaea and their relationships are competitive. This results in wide variety of secondary metabolites produced by marine sediment-derived fungi both for environmental adaptation and for interspecies interactions. Earlier marine fungal metabolites were investigated mainly for their antibacterial and antifungal activities, but now also as anticancer and cytoprotective drug candidates. This review aims to describe low-molecular-weight secondary metabolites of marine sediment-derived fungi in the context of their biological activity and covers research articles published between January 2016 and November 2020.

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Phenalenones from a Marine-Derived Fungus Penicillium sp.

Cited by 17 publications

References 29 publications

Bioactive Bis(indole) Alkaloids from a Spongosorites sp. Sponge

Bioactive Bis(indole) Alkaloids from a Spongosorites sp. Sponge

Ent-Peniciherqueinone Suppresses Acetaldehyde-Induced Cytotoxicity and Oxidative Stress by Inducing ALDH and Suppressing MAPK Signaling

Metabolites of Marine Sediment-Derived Fungi: Actual Trends of Biological Activity Studies

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