Fungus Penicillium Sp Research Articles

(±) Benzomalvins E isolated from Penicillium sp. SYPF 8411 in the rhizosphere soil of Codonopsis clematidea

(+) Benzomalvins E (1) and (-) Benzomalvins E (2), a pair of epimeric derivatives, together with three known benzomalvins (3–5), were isolated from solid cultures of a interrhizospheric fungus Penicillium sp. SYPF 8411. The planar structure of (+) Benzomalvins E (1) has been previously reported. While, the absolute configuration of compound 1 was established by X-ray crystallographic analysis for the first time. The planar structure of the new compound 2 were elucidated by detailed interpretation of their HR ESI-TOF MS and NMR spectroscopic data. The absolute configuration of compound 2 was established by Rh2(OCOCF3)4-induced CD spectral data and the electronic circular dichroic (ECD) method. Furthermore, the epimerization induced by pH, temperature and H2O was revealed. Benzomalvins (1–3, 5), a type of indoximod, enhanced the cytotoxic capability of 5-fluorouracil against A549.

GKK1032C, a new alkaloid compound from the endophytic fungus Penicillium sp. CPCC 400817 with activity against methicillin-resistant S. aureus.

Five alkaloid compounds (1-5), including one new compound, GKK1032C (1), and four known compounds, pyrrospirones E (2) and F (3), and GKK1032B (4) and A2 (5) were isolated from the culture of endophytic fungus Penicillium sp. CPCC 400817. The planar structures of all compounds were elucidated by NMR and MS spectra. The relative configuration of new compound GKK1032C (1) was deduced from the vicinal J-values and ROESY spectral data. Compound 1 exhibited potent antibacterial activity against methicillin-resistant Staphylococcus aureus with an MIC value of 1.6 μg ml-1.

Bioprospecting potential and secondary metabolite profile of a novel sediment-derived fungus Penicillium sp. ArCSPf from continental slope of Eastern Arabian Sea

ABSTRACTMarine fungi, one of the major decomposers of marine environment, is found to produce potential enzymes and novel biomolecules. The present study explored bioprospecting potentials such as antimicrobial, anticancer and enzymatic activities of marine sediment-derived fungi isolated from continental slope of Eastern Arabian Sea. Morphology and ITS sequencing identified the fungus as Penicillium sp. ArCSPf. The fungal strain exhibited amylase, gelatinase, phytase, lipase and pectinase activity. The active fraction obtained from the ethyl acetate extract column fractionation (F2) of fungus showed antibacterial activity against both methicillin-resistant Staphylococcus aureus (MRSA) and Bacillus cereus. Minimum inhibitory concentrations of F2 were 125 μg/mL for MRSA and 62.5 μg/mL for B. cereus. The active fraction showed a significant anticancer activity (IC50 = 22.79 µg/mL) against MCF-7 breast cancer cells. The secondary metabolite (Z)-Octadec-9-enamide (oleamide, m/z 282.27 (M + H+)] was identified in the LC-MS/MS analysis of active fraction F2 in positive ionisation mode. To the best of our knowledge, this is the first report on exploring the bioprospecting potential of a sediment-derived fungus from continental slope of eastern Arabian Sea for the production of therapeutically active compounds.

Citriperazines A-D produced by a marine algae-derived fungus Penicillium sp. KMM 4672

Four new diketopiperazine alkaloids, citriperazines A-D were isolated from algae-derived Penicillium sp. KMM 4672. The structures of compounds 1–4 were determined using spectroscopic methods. The absolute configurations of compounds 1 and 4 were established by comparison of calculated and experimental ECD spectra. The cytotoxicity of compounds 1–4 against several human prostate cell lines was evaluated.

Dongtingnoids A–G: Fusicoccane Diterpenoids from a Penicillium Species

Five new diterpenoid glycosides, dongtingnoids A-E (1-5), two new diterpenoid aglycones, dongtingnoids F and G (6 and 7), and two known analogues, cotylenins E and J (8 and 9), belonging to the fusicoccane family, were isolated from the fungus Penicillium sp. DT10, which was derived from wetland soil from Dongting Lake. Their structures and absolute configurations were elucidated based on spectroscopic analyses, acid hydrolysis, ECD calculations, and X-ray crystallography. Dongtingnoid C (3) is the first 16-nor-fusicoccane diterpenoid glycoside reported and is proposed to form by oxidative demethylation. Compounds 1, 4, and 5 showed comparable seed-germination-promoting activities to that previously reported for the growth regulator cotylenin E (8).

Optimization of cellulase enzyme production from fungi Penicillium sp. SLL06 isolated from salak leaf litter (Salacca edulis)

Abstract. Utami AP, Setyaningsih R, Pangastuti A, Sari SLA. 2019. Optimization of cellulase enzyme production from fungi Penicillium sp. SLL06 isolated from salak leaf litter (Salacca edulis). Pros Sem Nas Masy Biodiv Indon 5: 145-149. Cellulose is one of the important enzymes in industry and biotechnology. The need for enzymes is increasing, so that increase in production is needed. To fulfill the need for enzyme needs to increase enzymes production. One of the effort to increase production is to optimize production conditions. Cellulolytic fungi Penicillium sp. SLL06 has been isolated from salak leaf litter (Salacca edulis). This study aims to determine the optimum of incubation time, temperature, and pH for cellulose production and find out the specific conditions of cellulose enzyme by fungi Penicillium sp. SLL06 at optimum conditions. Inoculum of Penicillium sp. SLL06 contained 1x106 spores/mL was inoculated into growth media. The optimum growth time is obtained from the growth curve by measuring the dry weight of the cell. Fungal culture from growth media was inoculated into production media with variations in temperature and pH. The crude extract was measured for enzyme production to determine the optimum conditions. The enzyme specific activity was measured after the optimum conditions of cellulase enzyme production were obtained.The results of this study indicated that Penicillium sp. SLL 06 produced cellulase enzymes optimally at 3 days incubation time, 30?C temperature and pH 5.5 with 0,4406 U/mL enzyme production value and 0.0369 gram dry cell biomass. The value of cellulase enzyme specific activity is 0.9995 U/mg.

Two new meroterpenoids and two new monoterpenoids from the deep sea-derived fungus Penicillium sp. YPGA11

Twelve terpenoids, including two new 3,5-dimethylorsellinic acid-based meroterpenoids (1 and 2) and two new monoterpenoids (11 and 12), were obtained from the deep-sea fungus Penicillium sp. YPGA11. Their structures were determined by extensive analyses of spectroscopic data, and the absolute configurations of 1 and 2 were determined by comparisons of experimental and calculated ECD spectra. Compounds 1 and 2, bearing a 23-aldehyde or 23-carboxylic acid group, were rarely found in compounds with similar carbon skeleton. All compounds but 11 were evaluated for inhibitory effects towards nitric oxide production induced by lipopolysaccharide in RAW 264.7 macrophage cells. Compound 9 exhibited significant inhibitory effects with an IC50 value of 7.58 μM, being comparable to the positive control, quercetin (10.97 μM).

Neuroprotective Activity of Some Marine Fungal Metabolites in the 6-Hydroxydopamin- and Paraquat-Induced Parkinson's Disease Models.

A new melatonin analogue 6-hydroxy-N-acetyl-β-oxotryptamine (1) was isolated from the marine-derived fungus Penicillium sp. KMM 4672. It is the second case of melatonin-related compounds isolation from microfilamentous fungi. The neuroprotective activities of this metabolite, as well as 3-methylorsellinic acid (2) and 8-methoxy-3,5-dimethylisochroman-6-ol (3) from Penicillium sp. KMM 4672, candidusin A (4) and 4″-dehydroxycandidusin A (5) from Aspergillus sp. KMM 4676, and diketopiperazine mactanamide (6) from Aspergillus flocculosus, were investigated in the 6-hydroxydopamine (6-OHDA)- and paraquat (PQ)-induced Parkinson’s disease (PD) cell models. All of them protected Neuro2a cells against the damaging influence of 6-OHDA to varying degrees. This effect may be realized via a reactive oxygen species (ROS) scavenging pathway. The new melatonin analogue more effectively protected Neuro2A cells against the 6-OHDA-induced neuronal death, in comparison with melatonin, as well as against the PQ-induced neurotoxicity. Dehydroxylation at C-3″ and C-4″ significantly increased free radical scavenging and neuroprotective activity of candidusin-related p-terphenyl polyketides in both the 6-OHDA- and PQ-induced PD models.

Bioactive Penicipyrrodiether A, an Adduct of GKK1032 Analogue and Phenol A Derivative, from a Marine-Sourced Fungus Penicillium sp. ZZ380.

Penicipyrrodiether A, an adduct of GKK1032 analogue and phenol A derivative, was isolated from a culture of marine-associated fungus Penicillium sp. ZZ380 and represents the first example of this type of fungal metabolite. Its structure was elucidated by extensive spectroscopic analyses, including 1D- and 2D-NMR, HRESIMS, MS/MS, and electronic circular dichroism calculation as well as single-crystal X-ray diffraction. Penicipyrrodiether A showed antibacterial activity in inhibiting the growth of methicillin-resistant Staphylococcus aureus with a MIC value of 5.0 μg/mL. Its plausible pathway for biosynthesis has been proposed.

New Verrucosidin Derivatives from the Marine-Derived Fungus Penicillium sp. XL-01

Two new verrucosidin derivatives, named nordeoxyverrucosidin (1) and norverrucosidinol acetate (2), along with three known analogues (3–5) were isolated from the marine-derived fungus Penicillium sp. XL-01 collected from the Bohai Sea. Their structures and relative configurations were elucidated by comparing with literature data and a combination of spectroscopic techniques. The absolute configuration of 1 was assigned by quantum chemical calculation of the electronic circular dichroism (ECD) spectrum. Compounds 1 and 3 displayed promising cytotoxic activity against the MGC-803 cell line, with IC50 values of 0.96 and 1.14 μM, respectively, more effective than the positive control (cisplatin).

Peniginsengins B⁻E, New Farnesylcyclohexenones from the Deep Sea-Derived Fungus Penicillium sp. YPGA11.

Chemical examination of the EtOAc extract of the deep sea-derived fungus Penicillium sp. YPGA11 resulted in the isolation of four new farnesylcyclohexenones, peniginsengins B–E (1–4), and a known analog peniginsengin A (5). The structures of compounds 1–4 were determined on the basis of comprehensive analyses of the nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data, and the absolute configurations of 1, 2, and 4 were determined by comparisons of experimental electronic circular dichroism (ECD) with calculated ECD spectra. Compounds 1–5, characterized by a highly oxygenated 1-methylcyclohexene unit and a (4E,8E)-4,8-dimethyldeca-4,8-dienoic acid side chain, are rarely found in nature. Compounds 2–4 exhibited antibacterial activity against Staphylococcus aureus.

Penicindopene A, a new indole diterpene from the deep-sea fungus Penicillium sp. YPCMAC1

A new indole diterpene, named penicindopene A (1), together with seven known compounds (2 – 8), was isolated from the deep-sea fungus Penicillium sp. YPCMAC1. The structure of penicindopene A was elucidated by extensive spectroscopic analyses (1 D and 2 D NMR, and HRESIMS data), in addition to the ECD calculations for the assignments of its absolute configuration. Penicindopene A represented the first example of indole diterpenes possessing a 3-hydroxyl-2-indolone moiety, and it exhibited moderate cytotoxicities against A549 and HeLa cell lines with IC50 values of 15.2 and 20.5 µM, respectively.

Peniazaphilin A, a new azaphilone derivative produced by Penicillium sp. CPCC 400786.

A new azaphilone derivative, named peniazaphilin A (1) and one known isocoumarin, (R)-3-methyl-6-hydroxy-8-methoxy-3,4-dihydroisocoumarin (2) were isolated from the fungus Penicillium sp. CPCC 400786. Their structures were elucidated by means of extensive spectroscopic analysis. The absolute configuration of 2 was established by circular dichroism for the first time. Compounds 1 and 2 exhibited weak anti-HIV activities with the IC50 values of 60.4 and 69.3 μM, respectively.

(2R,3S)-Pinobanksin-3-cinnamate promotes osteoblast differentiation through cAMP and cGMP pathways

Flavones have the potential of being used as a dietary supplement for bone health promotion beyond calcium and vitamin D. Recent studies have showed that flavones enhanced bone formation and inhibited bone resorption by affecting osteoblast and osteoclast differentiation through various cell signaling pathways. In this study, we investigated the effects of a new flavone (2R,3S)-pinobanksin-3-cinnamate, isolated from the metabolites of the endophytic fungus Penicillium sp. FJ-1 of Acanthus ilicifolius L., Acanthaceae, on osteoblast differentiation by using MC3T3-E1 cells. It was observed that (2R,3S)-pinobanksin-3-cinnamate promoted osteoblast differentiation, as evidenced by increased mineralization process and alkaline phosphatase activity, as well as expression of genes encoding the bone differentiation. Moreover (2R,3S)-pinobanksin-3-cinnamate treatment upregulated the gene expression of wingless-type MMTV integration site family, bone morphogenetic protein and runt-related transcription factor 2, and protein expression of phosphor-Smad1/5/8, β-catenin and runt-related transcription factor 2 in MC3T3-E1 cells. The osteoblast differentiation effects induced by (2R,3S)-pinobanksin-3-cinnamate were attenuated by the bone morphogenetic protein antagonist Noggin, and wingless-type MMTV integration site family signaling pathway inhibitors Dickkopf-1. Co-treatment with adenosine 30,50-cyclic monophosphate and guanosine 30,50-cyclic monophosphate pathway inhibitors, H89 and KT5823, respectively, reversed the (2R,3S)-pinobanksin-3-cinnamate-induced activations of p-Smad1/5/8, β-catenin, and runt-related transcription factor 2. Our data demonstrated that (2R,3S)-pinobanksin-3-cinnamate promoted the osteoblast differentiation of MC3T3-E1 cells, at least partially through the adenosine 30,50-cyclic monophosphate and guanosine 30,50-cyclic monophosphate signaling pathways, providing the scientific rational to develop (2R,3S)-pinobanksin-3-cinnamate against bone loss-associated diseases.

Tanzawaic acid derivatives from freshwater sediment-derived fungus Penicillium sp.

Chemical investigation of a freshwater sediment-derived fungus, Penicillium sp. (S1a1), led to the isolation of three new tanzawaic acid derivatives, including penitanzchroman (1), tanzawaic acids Y (2) and Z (3), along with six known tanzawaic acid analogues (4-9), three known isochromans (10-12) and two known benzoquinones (13 and 14). The structures of the new compounds were established based on high-resolution mass spectrometry, and detailed analysis of one- and two-dimensional NMR spectroscopy. The relative configuration of the new compounds was assigned on the basis of NMR spectroscopic data including ROESY spectra. The absolute configuration was determined based on the specific optical rotation, in addition to biogenetic considerations in comparison with related co-isolated known metabolites. Penitanzchroman (1) constitutes a hitherto unprecedented skeleton, formed of tanzawaic acid A (5) and (3S)-6-hydroxy-8-methoxy-3,5-dimethylisochroman (10) linked by a CC bond. Moreover, all compounds were evaluated for their antibacterial and cytotoxic activities.

Peniciphenalenins A−F from the culture of a marine-associated fungus Penicillium sp. ZZ901

Marine-derived fungi of the genus Penicillium represent a huge potential for synthesizing the secondary metabolites with structural and bioactive uniqueness and diversity. In this study, six previously undescribed compounds peniciphenalenins A−F and four known compounds (+)-sclerodin, (+)-scleroderolide, (+)-sclerodione, and physcion were isolated from the culture of a marine-derived fungus Penicillium sp. ZZ901. Structures of the isolated compounds were elucidated by a combination of extensive NMR spectroscopic analysis, HRESIMS data, optical rotation value, ECD calculation, and single crystal X-ray diffraction. Peniciphenalenins A−C are the second examples of the type of neoherqueinones. The possible biosynthetic route of nine phenalenone derivatives has been suggested. The known (+)-scleroderolide showed both antiproliferative activity against glioma cells with IC50 values of 23.24–37.26 μM and antibacterial activity in suppressing the growth of methicillin-resistant Staphylococcus aureus and Escherichia coli with MIC values of 7.0 and 9.0 μg/mL, respectively.

Anti-Rhizopus activity of tanzawaic acids produced by the hot spring-derived fungus Penicillium sp. BF-0005.

A silkworm infection assay with the pathogenic fungus Rhizopus oryzae was established. Microbial culture broths were screened for anti-Rhizopus antibiotics using this assay. A new compound, tanzawaic acid R was isolated along with known and structurally related tanzawaic acids and arohynapene A from the culture broth of the hot spring-derived fungus Penicillium sp. BF-0005. The structure of tanzawaic acid R was elucidated by various spectroscopic data including 1D and 2D nuclear magnetic resonance spectroscopy. Tanzawaic acids A, B, C, and R and arohynapene A exhibited antifungal activity against R. oryzae. Tanzawaic acids A and B dose-dependently exerted therapeutic effects in the silkworm infection assay with R. oryzae.

Antibacterial sorbicillin and diketopiperazines from the endogenous fungus Penicillium sp. GD6 associated Chinese mangrove Bruguiera gymnorrhiza

One new sorbicillin derivative, 2-deoxy-sohirnone C (1), one new diketopiperazine alkaloid, 5S-hydroxynorvaline-S-Ile (2), and two naturally occurring diketopiperazines, 3S-hydroxylcyclo(S-Pro-S-Phe) (3) and cyclo(S-Phe-S-Gln) (4), together with three known compounds were isolated from the Chinese mangrove endophytic fungus Penicillium sp. GD6. Their structures were determined on the basis of extensive spectroscopic analyses and by comparison with literature data. The absolute configuration of 3-hydroxyl moiety in 3 was determined by Mosher's method, while the absolute stereochemistry of 2 and 4 was established by comparison with the CD spectra of natural and synthesized diketopiperazines. Compound 1 showed moderate antibacterial activity against Methicillin-resistant Staphylococcus aureus with a MIC value of 80 μg·mL−1.

A New Breviane Spiroditerpenoid from the Marine-Derived Fungus Penicillium sp. TJ403-1.

Marine-derived fungi are a promising and untapped reservoir for discovering structurally interesting and pharmacologically active natural products. In our efforts to identify novel bioactive compounds from marine-derived fungi, four breviane spiroditerpenoids, including a new compound, brevione O (1), and three known compounds breviones I (2), J (3), and H (4), together with a known diketopiperazine alkaloid brevicompanine G (5), were isolated and identified from an ethyl acetate extract of the fermented rice substrate of the coral-derived fungus Penicillium sp. TJ403-1. The absolute structure of 1 was elucidated by HRESIMS, one- and two-dimensional NMR spectroscopic data, and a comparison of its electronic circular dichroism (ECD) spectrum with the literature. Moreover, we confirmed the absolute configuration of 5 by single-crystal X-ray crystallography. All the isolated compounds were evaluated for isocitrate dehydrogenase 1 (IDH1) inhibitory activity and cytotoxicity, and compound 2 showed significant inhibitory activities against HL-60, A-549, and HEP3B tumor cell lines with IC50 values of 4.92 ± 0.65, 8.60 ± 1.36, and 5.50 ± 0.67 µM, respectively.

New Eudesmane-Type Sesquiterpenoids from the Mangrove-Derived Endophytic Fungus Penicillium sp. J-54.

Four new eudesmane-type sesquiterpenoids, penicieudesmol A–D (1–4), were isolated from the fermentation broth of the mangrove-derived endophytic fungus Penicillium sp. J-54. Their structures were determined by spectroscopic methods, the in situ dimolybdenum CD method, and modified Mosher’s method. The bioassays results showed that 2 exhibited weak cytotoxicity against K-562 cells.