Fungus Penicillium Sp Research Articles

Citrinin and α-pyrone derivatives with pancreatic lipase inhibitory activities from Penicillium sp. SCSIO 41302

One new citrinin monomer derivative (1), and two new natural products α-pyrone analogues (2a and 2b), were isolated from the sponge derived fungus Penicillium sp. SCSIO 41302. Their structures were determined by extensive spectroscopic analysis, chiral-phase HPLC analysis, modified Mosher’s method, ECD calculations, and X-ray single-crystal diffraction. Bioactivity screening showed that compounds 2b and 8 exhibited obvious inhibitory activities against pancreatic lipase and acetyl cholinesterase with IC50 values of 48.5 and 4.8 μM, respectively, which indicated that different chiral center between enantiomers (2a and 2b) might result in different biological activities (IC50 value against PL for 2a >100 μg/ml).

Pests and Diseases in Foxtail Millet (Setaria italica L. Beauv.) Cultivated in The Greenhouse

Greenhouse ecosystem with more stable abiotic factors could affect the population and diversity of pests and diseases found on foxtail millet (Setaria italica L. Beauv.) compared to their natural ecosystems. We observed and identified pests and diseases in seven genotypes of foxtail millet namely “Toraja”, “ICERI 5”, “ICERI 6”, “Botok 4”, “Botok 10”, “Mauliru”, and “Hambapraing”; these activities are important for the formulation of appropriate integrated pest management techniques. Using plant samples that were at the end of their vegetative phase, we found white mycelia of Fusarium incarnatum (yellowish-white colonies) and F. verticilloides (violetish-pink colonies) covering the ear-tip of the seeds and developed rapidly leading to seed rotten symptoms in “Toraja”, “ICERI 5”, and “ICERI 6”. The disease severity remained constant after these integrated management techniques were put in place. However, abnormalities in leaves leading to failure of panicle emergence occurred in “Botok 4”, “Botok 10”, “Mauliru”, and “Hambapraing”. These were caused by the fungi Penicillium sp. Identical controlling techniques were applied to this incidence and the disease incidence was reduced. Corn leaf aphids (Rhophalosiphum maidis) and rice mealybugs (Brevenia rehi) were recorded as main insect pests with severe attack. The aphid, R. maidis, colonized the stems and were associated with the sooty mold (Capnodium sp.), resulting in wilting. The mealybugs, B. rehi, colonized the flag leaves resulting in leaf rotting. Insecticide and isolating the attacked plants were used as the controlling techniques. Red-mites (Tetranychus urticae) were also detected as indicated by chlorotic spots on the upper part of the leaves. Acaricide was used to reduce its population. The pests and diseases found in the seven genotypes of foxtail millet are commonly known to occur in Poaceae. In general, greenhouse ecosystem for foxtail millet facilitated planting with high population with lower diversity of pests and diseases compared to the open field planting.

New Tetramic Acid Derivatives From the Deep-Sea-Derived Fungus Penicillium sp. SCSIO06868 With SARS-CoV-2 Mpro Inhibitory Activity Evaluation.

Three new tetramic acid derivatives (1–3) and a new polyketide (4) along with eight known compounds (5–12) were isolated from cultures of the deep-sea-derived fungus Penicillium sp. SCSIO06868. Four new structures were elucidated by analysis of one-dimensional/two-dimensional nuclear magnetic resonance (NMR) data and high-resolution electrospray ionization mass spectrometry. Their absolute configurations were established by X-ray crystallography analysis and comparison of the experimental and reported electronic circular dichroism (ECD) values or specific optical rotation. Compound 3 exhibited potent, selective inhibitory activities against Staphylococcus aureus and methicillin-resistant S. aureus with minimum inhibitory concentration values of both 2.5 μg/ml. Also, compound 3 showed weak antiviral activity against severe acute respiratory syndrome coronavirus 2 main protease, which was responsible for the coronavirus disease 2019 pandemic.

Indole diketopiperazine alkaloids and aromatic polyketides from the Antarctic fungus Penicillium sp. SCSIO 05705

A new indole diketopiperazine alkaloid, named penilline D (1), together with five known indole alkaloid analogues (2–5, 11), two meroterpenoids (6 and 12), and four butenolide derivatives (7–10), were isolated from the Antarctic fungus Penicillium sp. SCSIO 05705. Extensive spectroscopic analysis and electronic circular dichroism (ECD) calculation were used to elucidate the structure of penilline D (1), including its absolute configuration. All isolated compounds (1–12) were evaluated for their cytotoxic, antibacterial and enzyme inhibitory activities against acetylcholinesterase (AChE) and pancreatic lipase (PL). Among them, compound 5 exhibited moderate in vitro cytotoxic activity against the 143B cell line with IC50 value of 12.64 ± 0.78 μM. Compound 6 showed strong inhibitory activity against AChE with IC50 value of 0.36 nM (IC50 18.7 nM for Tacrine), while compounds 6 and 11 showed weak PL enzyme inhibitory activity. Furthermore, an in silico molecular docking study was also performed between 6 and AChE.

New Antiproliferative Compounds against Glioma Cells from the Marine-Sourced Fungus Penicillium sp. ZZ1750

Seven novel compounds, namely peniresorcinosides A–E (1–5), penidifarnesylin A (6), and penipyridinone A (7), together with the 11 known ones 8–17, were isolated from a culture of the marine-associated fungus Penicillium sp. ZZ1750 in rice medium. The structures of the new compounds were established based on their high-resolution electrospray ionization mass spectroscopy (HRESIMS) data, extensive nuclear magnetic resonance (NMR) spectroscopic analyses, chemical degradation, Mosher’s method, 13C-NMR calculations, electronic circular dichroism (ECD) calculations, and single crystal X-ray diffraction. Peniresorcinosides A (1) and B (2) are rare glycosylated alkylresorcinols and exhibited potent antiglioma activity, with IC50 values of 4.0 and 5.6 µM for U87MG cells and 14.1 and 9.8 µM for U251 cells, respectively.

Biochemical synthesis of the medicinal sugar l-gulose using fungal alditol oxidase

Some rare sugars can be potently medicinal, such as l-gulose. In this study, we present a novel alditol oxidase (fAldOx) from the soil fungus Penicillium sp. KU–1, and its application for the effective production of l-gulose. To the best of our knowledge, this is the first report of a successful direct conversion of d-sorbitol to l-gulose. We further purified it to homogeneity with a ∼108-fold purification and an overall yield of 3.26%, and also determined the effectors of fAldOx. The enzyme possessed broad substrate specificity for alditols such as erythritol (kcat/KM, 355 m−1 s−1), thus implying that the effective production of multiple rare sugars for medicinal applications may be possible.

New polyhydroxanthones from the marine-associated fungus Penicillium sp. ZZ1750

Five polyhydroxanthones, including new natural product ergochrome C (1) and new compounds ergochromes D–G (2–5), together with 11 known compounds (6–16), were isolated from the marine-associated fungus Penicillium sp. ZZ1750. Structures of the polyhydroxanthones were determined based on their HRESIMS data, extensive NMR spectroscopic analyses, the results from single crystal X-ray diffraction, 13C NMR and ECD calculations. All isolated compounds were assayed for their antiproliferative activity against human glioma U87MG and U251 cells and antimicrobial activities in inhibiting the growth of methicillin-resistant Staphylococcus aureus (MRSA), Escherichia coli, and Candida albicans. The five polyhydroxanthones of ergochromes C–G (1–5) had moderate antimicrobial activities against MRSA and C. albicans with MIC values of 16–36 μg/mL. Only known compound calyxanthone (9) showed weak antiproliferative activity (IC50: 46.6 μM) against glioma U87MG cells.

Two new benzophenones isolated from a mangrove-derived fungus Penicillium sp.

One new benzophenone derivative, named penibenzophenone C (1), and a new benzophenone natural product, neamed penibenzophenone D (2), together with two known compounds (3, 4) were isolated from the EtOAc extract of the endophytic fungus Penicillium sp. isolated from the mangrove Acanthus ilicifolius L. collected in the South China Sea. The structures of 1-4 were elucidated by extensive NMR spectral interpretation and MS data. The new compounds 1 and 2 showed moderate antibacterial activities against methicillin-resistant Staphylococcus aureus with the MIC values of 3.12 and 6.25 μg ml-1, respectively.

New Drimane Sesquiterpenes and Polyketides from Marine-Derived Fungus Penicillium sp. TW58-16 and Their Anti-Inflammatory and α-Glucosidase Inhibitory Effects.

Marine fungi-derived natural products represent an excellent reservoir for the discovery of novel lead compounds with biological activities. Here, we report the identification of two new drimane sesquiterpenes (1 and 2) and six new polyketides (3–8), together with 10 known compounds (9–18), from a marine-derived fungus Penicillium sp. TW58-16. The planar structures of these compounds were elucidated by extensive 1D and 2D NMR, which was supported by HR-ESI-MS data. The absolute configurations of these compounds were determined by experimental and calculated electronic circular dichroism (ECD), and their optical rotations compared with those reported. Evaluation of the anti-inflammatory activity of compounds 1–18 revealed that compound 5 significantly inhibited the release of nitric oxide (NO) induced by lipopolysaccharide (LPS) in RAW264.7 cells, correlating with the inhibition of expression of inducible nitric oxide synthase (iNOS). In addition, we revealed that compounds 1, 3–6, 14, 16, and 18 showed strong α-glucosidase inhibitory effects with inhibition rates of 35.4%, 73.2%, 55.6%, 74.4%, 32.0%, 36.9%, 88.0%, and 91.1%, respectively, which were comparable with or even better than that of the positive control, acarbose. Together, our results illustrate the potential of discovering new marine-based therapeutic agents against inflammation and diabetes mellitus.

Austins-Type Meroterpenoids from a Mangrove-Derived Penicillium sp.

Three unusual austins-type meroterpenoids penicianstinoids C-E (1-3) were obtained from the mangrove-derived fungus Penicillium sp. TGM112. The structures of 1-3 including absolute configurations were determined by detailed NMR, MS spectroscopic data, X-ray diffraction analysis, and calculated electronic circular dichroism data. Penicianstinoid C (1) was the first austins-type meroterpenoid with a unique 6/6/6/5 rearranged tetracyclic skeleton possessing two unusual spirocyclic moieties (2-oxaspiro[5.5]undeca-4,7-dien-3-one and 6-methylene-2-oxaspiro[4.5]decane-1,4-dione). Penicianstinoid D (2) was an unusual austins-type meroterpenoid with a 6/6/6/6 tetracyclic skeleton containing an octahydro-2H-chromen-2-one unit. Penicianstinoid E (3) possessed a 6/5/6/6/6/5 fused hexacyclic skeleton with an uncommon five-membered ether ring system. The plausible biosynthetic pathway of 1-3 is also proposed. Compounds 1 and 3 inhibited the growth of newly hatched Helicoverpa armigera Hubner larvae with IC50 values of 100 and 200 μg/mL, respectively.

Indole-Terpenoids With Anti-inflammatory Activities From Penicillium sp. HFF16 Associated With the Rhizosphere Soil of Cynanchum bungei Decne.

Four new indole-terpenoids (1–4) named encindolene A, 18-O-methyl-encindolene A, encindolene B, and encindolene C, as well as three known analogs (5–7), were isolated from the fungus Penicillium sp. HFF16 from the rhizosphere soil of Cynanchum bungei Decne. The structures of compounds including absolute configurations were elucidated by spectroscopic data and electronic circular dichroism (ECD) analysis. Anti-inflammatory activity evaluation revealed that compounds 1–7 inhibit the production of nitric oxide with IC50 values of 79.4, 49.7, 81.3, 40.2, 86.7, 90.1, and 54.4 μM, respectively, and decrease the levels of tumor necrosis factor-α, interleukin-6 contents in lipopolysaccharide-induced RAW264.7 macrophages.

A new bioactive isocoumarin from the mangrove-derived fungus Penicillium sp. TGM112

A new isocoumarin, penicimarin N (1), along with five known compounds (2-6), were isolated from the mangrove-derived fungus Penicillium sp. TGM112. The structure of 1 was elucidated on the basis of extensive spectroscopic data analysis, and the absolute configuration of 1 was determined by comparison of their circular dichroism (CD) spectra with the literature. The structures of known compounds were determined by comparison with the literature data. All the isolated compounds were examined for their antioxidant and α-glucosidase activities. Compound 1 showed strong antioxidant activity with the IC50 value of 1.0 mM, and 1 also exhibited moderate inhibitory activity against α-glucosidase with the IC50 value of 620 μM.

Endophytes and Rhizosphere Fungi from Galam (<i>Melaleuca cajuputi</i> Powell.) which has the Potential to Produce Indole Acetic Acid (IAA)

Some types of fungi are known to have the ability to produce Indole Acetic Acid (IAA). Fungi can be isolated from the rhizosphere and tissues of various plants, including from the rhizosphere and the root "Galam" (Melaleuca cajuputi Powell.), which grow predominantly in peatlands. Therefore, the purposes of this study were: (a) to isolate and measure the potential of fungi from endophytic and rhizospheric of “Galam”(M. cajuputi) as a producer of IAA hormone, (b) determine the types of fungal interaction that occur and their potential to increase the total IAA hormone produced. This research begins with isolation, purification, isolate screening, analysis of IAA hormone production, data analysis, seed germination test and isolates identification. The result showed that the concentration of IAA produced by Penicillium sp. IRZ15 was 5.86 ± 0.47 μg.mL-1 to 8.46 ± 0.26 μg.mL-1 and Syncephalastrum sp. AG15 is 4.77 ± 0.44 μg.mL-1 to 8.77 ± 0.25 μg.mL-1. Meanwhile, the combination of rhizospheric fungi Penicillium sp. IRZ15 and endophytic fungi Syncephalastrum sp. AG15 does not produce significantly different IAA concentrations (6.42 ± 0.34 μg.mL-1 to 9.19 ± 0.50 μg.mL-1 ) compared to fungi used alone without combinations.

Efficient production of the rare sugar l-gulose using a wheat-bran culture extract of Penicillium sp. KU-1.

We found that l-gulose, a rare sugar, was produced from d-sorbitol efficiently, using a wheat-bran culture extract of the fungus Penicillium sp. KU-1 isolated from soil. The culture extract showed enzyme activity for the oxidation of d-sorbitol to produce l-gulose; a high production yield of approximately 94% was achieved.

Isolation and Characterization of Anti-Inflammatory Sorbicillinoids from the Mangrove-Derived Fungus Penicillium sp. DM815.

Marine derived fungus has gained increasing ground in the discovery of novel lead compounds with potent biological activities including anti-inflammation. Here, we first report the characterization of one new sorbicillinoid (1) and fourteen known compounds (2-15) from the ethyl acetate (AcOEt) extract of a cultured mangrove derived fungus Penicillium sp. DM815 by UV, IR, HR ESI-Q-TOF MS, and NMR spectra. We then evaluated the anti-inflammatory effects of eleven sorbicillinoids (1-11) using cultured macrophage RAW264.7 cells. The results show that compound 9, and to a lesser degree compound 5, significantly inhibited the Gram-negative bacteria lipopolysaccharide (LPS)-induced upregulation of the inducible nitric oxide synthase (iNOS). Consistently, compounds 5 and 9 significantly reduced the level of nitric oxide (NO), the product of iNOS, induced by LPS. We further show that these two compounds dose-dependently inhibited LPS-triggered iNOS expression and NO production, but had no effect on proliferation of RAW264.7 cells in the presence of LPS. In conclusion, our study identifies novel and known sorbicillinoids as potent anti-inflammatory agents, holding the promise of developing novel anti-inflammation treatment in the future.

Penipyrols C–G and methyl-penipyrol A, α-pyrone polyketides from the mangrove derived fungus Penicillium sp. HDN-11-131

Six new α-pyrone polyketides, penipyrols C–G (1–5) and methyl-penipyrol A (6), together with one biogenetically related known compound, penipyrol A (7), were isolated from the extract of fungus Penicillium sp. HDN-11-131. Their structures including the absolute configurations were established by extensive spectroscopic analysis, Mosher’s method, and ECD calculations as well as biogenic considerations. Compounds 1–4 possess a rare skeleton featuring γ-butyrolactone linked to α-pyrone ring through double bond. Compound 1 can induce pancreatic β-cell regeneration in zebrafish at 10 μM, which demonstrated promising anti-diabetes potential.

Bioactive isocoumarins isolated from a mangrove-derived fungus Penicillium sp. MGP11

Two new isocoumarins penicimarins L-M (1–2), along with seven known analogues (3–9) were isolated from the mangrove-derived fungus Penicillium sp. MGP11. Compounds 1–2 were established by spectroscopic methods and comparison of their circular dichroism (CD) spectra with the literature. All isolated compounds were evaluated for antioxidant and α-glucosidase inhibitory activities. Compound 8 had better antioxidant activity (IC50 = 4.6 μM) than positive control trolox (IC50 = 12.9 μM). Compounds 5, 8 and 9 exhibited α-glucosidase inhibitory activity with the IC50 values of 776.5, 683.7 and 868.7 μM, respectively.

Ultrasound-Assisted Synthesis of Antimicrobial Inulin and Sucrose Esters with 10-Undecylenic Acid

An environmentally friendly and sustainable ultrasound-assisted esterification of long-chained inulin and sucrose with monounsaturated 10-undecylenic acid was performed. The obtained esters were characterized by thin-layer chromatography (TLC), Fourier transforms infrared spectroscopy (FTIR), and nuclear magnetic resonance (NMR) spectroscopy. The spectral analyses demonstrated the successful incorporation of the hydrophobic 10-undecylenoyl residue in the water-soluble carbohydrate backbone. Additionally, the antimicrobial potential of 10-undecylenic esters of inulin and sucrose were tested against nine microorganisms (Gram-positive and Gram-negative bacteria, yeasts, and fungi). Both esters inulin 10-undecylenate and sucrose 10-undecylenate (1 mg/ml) inhibited Bacillus subtilis ATCC 6633, Listeria monocytogenes ATCC 8632, Staphylococus aureus 745, Escherichia coli 3398, yeast Candida albicans 8673, and fungi Penicillium sp. Only inulin 10-undecylenate demonstrated antimicrobial activity against Salmonella typhy 745. Both esters were inactive against fungi Aspergillus niger. The current research demonstrated a new antimicrobial activity of inulin esters. Moreover, the use of “eco-friendly” synthesized inulin and sucrose esters with 10-undecylenic acid as antimicrobial substances with future applications in pharmaceutical and cosmetic products were demonstrated.

Xanthones and anthraquinones from the soil fungus Penicillium sp. DWS10-P-6.

Two new xanthones, oxisterigmatocystins J and K (1–2), and two new anthraquinones, versicolorins D and E (3–4), were isolated from solid cultures of the fungus Penicillium sp. DWS10-P-6, together with twelve known compounds (5–16). Their structures, including their absolute configurations, were characterized on the basis of extensive 1D NMR, 2D NMR, MS and CD spectral data. The cytotoxic activities of compounds 1–12 against HL-60, MDA-MB-231 and PC-3 cells were also evaluated. Compounds 4 and 5 showed significant cytotoxic activity against the HL-60 cell line with IC50 values of 1.65 μM and 1.05 μM, respectively.

A series of meroterpenoids with rearranged skeletons from an endophytic fungus Penicillium sp. GDGJ-285

Five new meroterpenoids (1–5), including three novel skeleton meroterpenoids, peniclactones A–C (1–3), and two new isoaustinone analogues (4 and 5), 6-hydroxyisoaustinone (4) and 6-ketoisoaustinone (5), were isolated from the fungus Penicillium sp. GDGJ-285.