Fungal Strain Penicillium Sp Research Articles

Terpenes and polyketides from the marine‐derived fungus Penicillium sp. OPR23‐FS02 with cytotoxic and antimicrobial effects

AbstractChemical study of the fermentation culture of the marine‐derived fungal strain Penicillium sp. OPR23‐FS02 led to isolation of ten secondary metabolites, including two terpenes, purpuride (1) and penioxalicin (2) and eight polyketides, trans‐3,4‐dihydro‐3,4,8‐trihydroxynaphthalen‐1(2H)‐one (3), chloromonilinic acid B (4), chrysophanol (5), emodin (6), ω‐hydroxyemodin (7), questin (8), endocrocin (9), and ergochrome F (10). Their structures were elucidated by analyzing their NMR and HRESI mass spectra and comparing with the literature data. Compound 9 was weakly cytotoxic against HepG2 cell line, with an IC50 value of 89.86 ± 2.63 µm. Compounds 4 and 10 showed antimicrobial effect against Enterococcus faecalis whereas 6 inhibited Bacillus cereus growth, with the same MIC values of 64 µm.

HPPO-Derived Meroterpenoids from the Marine-Derived Fungus Penicillium sp. SCSIO 41691.

Seven new 4-hydroxy-6-phenyl-2H-pyran-2-one (HPPO) derived meroterpenoids, 1-methyl-12a,12b-epoxyarisugacin M (1), 1-methyl-4a,12b-epoxyarisugacin M (2), 2,3-dihydroxy-3,4a-epoxy-12a-dehydroxyisoterreulactone A (3), 2-hydroxy-12a-dehydroxyisoterreulactone A (4), 3'-demethoxyterritrems B' (5), 4a-hydroxyarisugacin P (6), and 1-epi-arisugacin H (7), together with two known analogues (8 and 9), were isolated from the marine-derived fungal strain Penicillium sp. SCSIO 41691. Their structures were elucidated by spectroscopic methods, and the absolute configurations of compounds 1 and 3 were determined by single-crystal X-ray diffraction. Among them, 1 and 2 had a unique methyl migration in the basic meroterpenoid skeleton with a 12a,12b-epoxy or 4a,12b-epoxy group, and 3 was a highly oxygenated HPPO-derived meroterpenoid featuring a rare 6/5/6/6/6/6 hexacyclic system with a 3,4a-epoxy group. Biologically, 5 exhibited inhibitory activity against lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells with an IC50 value of 21 μM, more potent than the positive control indomethacin.

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The fungal strain Penicillium sp. HLLG‐122 was isolated from the root of mangrove Lumnitzera littorea (Jack) Voigt collected from Sanya, Hainan Island, China, which mainly produced meroterpenoid derivatives. Fifteen new meroterpenoids were isolated and characterized. The structures and absolute configurations of new compounds were elucidated by HRESIMS, NMR spectroscopy, single crystal X‐ray diffraction analysis, and electronic circular dichroism calculations. Among them, littoreanoid K (11) could suppress the levels of TNF‐α and IL‐6, and down‐regulate the protein expression of iNOS and COX‐2 in RAW 264.7 cells. More details are discussed in the article by Chen et al. on page 2507—2517.image

Pyrrospirones K-Q, Decahydrofluorene-Class Alkaloids from the Marine-Derived Fungus Penicillium sp. SCSIO 41512.

Seven new decahydrofluorene-class alkaloids, pyrrospirones K-Q (1-7), together with six known analogues (8-13) were isolated from the marine-derived fungal strain Penicillium sp. SCSIO 41512. Their structures were determined by extensive spectroscopic analysis, and their absolute configurations were established by single-crystal X-ray diffraction analysis and quantum chemical calculations of electronic circular dichroism spectra. Compounds 1 and 3 possess a novel decahydrofluorene-class alkaloid skeleton with a 6/5/6/8/5/6/13 and a 6/5/6/5/6/13 polycyclic system, respectively. Biologically, 13 displayed significant inhibitory activity against protein tyrosine phosphatases CD45, TCPTP, SHP1, and PTP1B with IC50 values of 8.1-17.8 μM, and 1, 2, 5, 8-10, 12, and 13 showed antibacterial activity against six pathogens. Their structure-activity relationship is also discussed.

Use of agroindustrial wastes for the production of cellulases by Penicillium sp. FSDE15

Cellulase refers to a group of enzymes like endoglucanases (CMCase), exoglucanases and β-glucosidase that have great industrial importance for the production of second-generation ethanol, e.g. The present study aimed to evaluate the CMCase and β-glucosidase activities of the fungal strain Penicillium sp. FSDE15 using different agroindustrial wastes (wheat bran, sugarcane bagasse and sugarcane straw) as carbon sources to the basal medium during Submerged Fermentation (SFm). When the medium presented wheat bran, highest CMCase and β-glucosidase yields were 1.03 U/mL (96 h) and 1.68 U/mL (168 h), respectively. For sugarcane bagasse medium, maximum enzymatic activity values were observed in 120 h culture (1.38 U/mL for CMCase and 0.55 U/mL for β-glucosidase). Sugarcane straw medium presented highest enzymatic yields after 120 h culture (1.02 U/mL of CMCase and 0.39 U/mL of β-glucosidase). The response surface methodology showed highest CMCase (1.3 U/mL) and β-glucosidase (6.5 U/mL) activities in the presence of lower levels of wheat bran (1%) (w/w), inoculum concentration of 105 spores/mL, temperatures of 41 °C and 33 °C, respectively. Penicillium sp. FSDE15 presented two isoforms of CMCase (150 kDa and around 30 kDa) and one isoform of β-glucosidase (70 kDa). Our study demonstrated that the production of cellulases with high activity by Penicillium sp. FSE15 in a culture medium with agroindustrial wastes, such as wheat bran, might be a promising alternative to reduce the cost of these molecules and facilitate their use in various industrial processes.

Terrein suppressed lipopolysaccharide-induced neuroinflammation through inhibition of NF-κB pathway by activating Nrf2/HO-1 signaling in BV2 and primary microglial cells

In the course of our continuous investigation on the bioactive marine-derived fungal metabolites, terrein was isolated from marine-derived fungal strain Penicillium sp. SF-7181. Terrein inhibited the overproduction of pro-inflammatory mediators, such as nitric oxide (NO) and prostaglandin E2 (PGE2), as well as inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in lipopolysaccharide (LPS)-stimulated BV2 and primary microglial cells. This compound also repressed the LPS-induced production of pro-inflammatory cytokines, interleukin (IL)-1β and IL-6. These inhibitory effects of terrein were associated with the inactivation of the nuclear factor kappa B (NF-κB) pathway through suppression of the translocation of p65/p50 heterodimer into the nucleus, the phosphorylation and degradation of inhibitor kappa B (IκB)-α and the DNA binding activity of the p65 subunit. In addition, terrein induced the protein expression of heme oxygenase (HO)-1 through the activation of nuclear transcription factor erythroid-2 related factor 2 (Nrf2) in BV2 and primary microglial cells. The anti-inflammatory effect of terrein was blocked by pre-treatment with a selective HO-1 inhibitor, suggesting that its anti-neuroinflammatory effect is mediated by HO-1 induction.

New preaustinoids from a marine-derived fungal strain Penicillium sp. SF-5497 and their inhibitory effects against PTP1B activity.

Chemical investigation of the marine-derived fungal isolate Penicillium sp. SF-5497 resulted in the isolation of two new preaustinoid-related meroterpenoids, named preaustinoid A6 (1) and preaustinoid A7 (2), along with three known metabolites (3-5). Their structures were elucidated by extensive spectroscopic analyses, such as 1D and 2D NMR and MS data. Among these, compounds 1 and 3 inhibited PTP1B activity in a dose-dependent manner, with IC50 values of 17.6 and 58.4 µM, respectively. Furthermore, kinetic analyses indicated that compound 1 inhibited PTP1B in a noncompetitive manner, with the Ki value of 17.0 µM.

Furanoaustinol and 7-acetoxydehydroaustinol: new meroterpenoids from a marine-derived fungal strain Penicillium sp. SF-5497.

Two new meroterpenoid-type fungal metabolites, furanoaustinol (1) and 7-acetoxydehydroaustinol (2), were isolated from the ethyl acetate extract of a marine-derived fungal strain Penicillium sp. SF-5497, along with eight (3-10) known meroterpenoids. Their structures were elucidated mainly based on the analysis of their NMR (1D and 2D) and MS data. Particularly, the novel meroterpenoid, furanoaustinol (1), belonging to the austin group, was identified to possess an unprecedented hexacyclic ring system. Biological evaluation of these compounds revealed that furanoaustinol (1) weakly inhibited the activity of protein tyrosine phosphatase 1B in a dose-dependent manner with an IC50 value of 77.2 μM. In addition, 7-acetoxydehydroaustinol (2) and four other known meroterpenoids (5, 7, 9, and 10) weakly suppressed the overproduction of nitric oxide in lipopolysaccharide-challenged BV2 microglial cells with IC50 values of 61.0, 30.1, 58.3, 37.6, and 40.2 μM, respectively.

Anti-Inflammatory Effects of Curvularin-Type Metabolites from a Marine-Derived Fungal Strain Penicillium sp. SF-5859 in Lipopolysaccharide-Induced RAW264.7 Macrophages.

Chemical study on the extract of a marine-derived fungal strain Penicillium sp. SF-5859 yielded a new curvularin derivative (1), along with eight known curvularin-type polyketides (2–9). The structures of these metabolites (1–9) were established by comprehensive spectroscopic analyses, including 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry (MS). In vitro anti-inflammatory effects of these metabolites were evaluated in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. Among these metabolites, 3–9 were shown to strongly inhibit LPS-induced overproduction of nitric oxide (NO) and prostaglandin E2 (PGE2) with IC50 values ranging from 1.9 μM to 18.1 μM, and from 2.8 μM to 18.7 μM, respectively. In the further evaluation of signal pathways involved in these effects, the most active compound, (10E,15S)-10,11-dehydrocurvularin (8) attenuated the expression of inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2) in LPS-stimulated RAW264.7 macrophages. Furthermore, compound 8 was shown to suppress the upregulation of pro-inflammatory mediators and cytokines via the inhibition of the nuclear factor-κB (NF-κB) signaling pathway, but not through the mitogen-activated protein kinase (MAPK) pathway. Based on the comparisons of the different magnitude of the anti-inflammatory effects of these structurally-related metabolites, it was suggested that the opening of the 12-membered lactone ring in curvularin-type metabolites and blocking the phenol functionality led to the significant decrease in their anti-inflammatory activity.

Diphenyl ether and benzophenone derivatives from the marine mangrove-derived fungus Penicillium sp. MA-37

Further investigation of the marine mangrove-derived fungal strain Penicillium sp. MA-37 led to the isolation of one new benzophenone, iso-monodictyphenone (1), two new diphenyl ether derivatives penikellides A (2) and B (3), and two known analogs monodictyphenone (4) and 6-[2-hydroxy-6-(hydroxymethyl)-4-methylphenoxy]-2-methoxy-3-(1-methoxy-3-methylbutyl)benzoic acid (5). The structures of these compounds were elucidated by spectroscopic analyses including 1D- and 2D-NMR and mass spectrometry. The brine shrimp lethality and antibacterial activity against five aquaculture pathogens were evaluated.

Tanzawaic acids I–L: Four new polyketides from Penicillium sp. IBWF104-06

Four new polyketides have been identified in culture filtrates of the fungal strain Penicillium sp. IBWF104-06 isolated from a soil sample. They are structurally based on the same trans-decalinpentanoic acid skeleton as tanzawaic acids A–H. One of the new compounds was found to inhibit the conidial germination in the rice blast fungus Magnaporthe oryzae at concentrations of 25 μg/mL.

Four New Citrinin Derivatives from a Marine-Derived Penicillium sp. Fungal Strain

Four new citrinin derivatives, including two citrinin dimers and two citrinin monomer derivatives, were isolated and identified from a marine-derived fungal strain Penicillium sp. ML226 along with six known related compounds. Their structures were elucidated by spectroscopic and chemical methods. The new compounds showed modest cytotoxic activity against HepG-2 cell line and weak antimicrobial activity against Staphylococcus aureus.

Decolorization of Reactive Dark Blue K-R by the synergism of fungus and bacterium using response surface methodology

The objective of this study was to investigate the potential ability of decolorizing Reactive Dark Blue K-R by the synergism of fungal strain Penicillium sp. QQ and bacterial strain Exiguobacterium sp. TL. The optimal conditions for decolorization determined by response surface methodology (RSM) were as follows: 12.5% (w/v) of both strains QQ and TL, 0.19% (w/v) of glucose, 0.09% (w/v) of yeast extract, pH 7.0, 37 °C and 200 mg/L of initial dye concentration. It was shown that about 97% of 200 mg/L K-R could be decolorized within 24 h under these conditions. Besides, strains QQ and TL co-cultures could decolorize 10 kinds of azo dyes effectively and be still 60% color removal when salinity increased to 15%. And most of the tested metal ions showed little influence on the decolorization except for Ni 2+. The results demonstrated that strains QQ and TL co-cultures could be useful for the practical bioremediation.

Yaequinolones, New Insecticidal Antibiotics Produced by Penicillium sp. FKI-2140

New nine insecticidal antibiotics designated yaequinolones were isolated from the culture broth of the fungal strain Penicillium sp. FKI-2140 by solvent extraction, centrifugal partition chromatography and HPLC. Yaequinolones showed growth inhibitory activity against brine shrimp (Artemia salina). Among them, yaequinolone F has the most potent activity with MIC value of 0.19 microg/ml.

Structure—Activity Relationships of Epolactaene Derivatives: Structural Requirements for Inhibition of Hsp60 Chaperone Activity.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Structure–activity relationships of epolactaene derivatives: structural requirements for inhibition of Hsp60 chaperone activity

Epolactaene is a microbial metabolite isolated from the fungal strain Penicillium sp. It arrests the cell cycle at the G 0/G 1 phase and induces the outgrowth of neurites in human neuroblastoma SH-SY5Y cells. In this communication, we report the structure–activity relationships (SARs) of new epolactaene derivatives, including those lacking the epoxylactam moiety and having various side chains. These derivatives were evaluated for their ability to inhibit the growth of human cancer cell lines. They were also analyzed for their ability to affect human heat shock protein 60 (Hsp60), which we have already identified as a protein that binds to epolactaene. We also identified the important structural framework of epolactaene/ETB (epolactaene tertiary butyl ester) for not only binding to Hsp60 but also inhibiting Hsp60 chaperone activity.