Endophytic Penicillium Sp Research Articles

Multioxidized polyketides from an endophytic Penicillium sp. YUD17006 associated with Gastrodia elata

Three novel, highly oxygenated polyketides, multioketides A−C (1−3), and three previously described multioxidized aromatic polyketides (4−6), were isolated from an endophytic Penicillium sp. YUD17006 associated with Gastrodia elata. Their chemical structures were elucidated using extensive spectroscopic data, electronic circular dichroism calculations, and single X-ray diffraction analysis. All metabolites were characterized by a typical α,β-unsaturated ketone fragment and exhibited a high degree of oxidation. Multioketides A and B were identified as a pair of epimers featuring a rare dihydroisobenzofuranone core. Multioketide C possessed a novel 5/6/6/6 heterotetracyclic chemical architecture with unusual 1,4-dioxin functionalities. Plausible biosynthetic pathways for 1−6 were proposed. Additionally, compound 3 demonstrated weak inhibitory activities against both acetylcholinesterase and protein tyrosine phosphatase 1B.

A New Quinazolinone Alkaloid along with Known Compounds with Seed-Germination-Promoting Activity from Rhodiola tibetica Endophytic Fungus Penicillium sp. HJT-A-6.

A new quinazolinone alkaloid named peniquinazolinone A (1), as well as eleven known compounds, 2-(2-hydroxy-3-phenylpropionamido)-N-methylbenzamide (2), viridicatin (3), viridicatol (4), (±)-cyclopeptin (5a/5b), dehydrocyclopeptin (6), cyclopenin (7), cyclopenol (8), methyl-indole-3-carboxylate (9), 2,5-dihydroxyphenyl acetate (10), methyl m-hydroxyphenylacetate (11), and conidiogenone B (12), were isolated from the endophytic Penicillium sp. HJT-A-6. The chemical structures of all the compounds were elucidated by comprehensive spectroscopic analysis, including 1D and 2D NMR and HRESIMS. The absolute configuration at C-13 of peniquinazolinone A (1) was established by applying the modified Mosher's method. Compounds 2, 3, and 7 exhibited an optimal promoting effect on the seed germination of Rhodiola tibetica at a concentration of 0.01 mg/mL, while the optimal concentration for compounds 4 and 9 to promote Rhodiola tibetica seed germination was 0.001 mg/mL. Compound 12 showed optimal seed-germination-promoting activity at a concentration of 0.1 mg/mL. Compared with the positive drug 6-benzyladenine (6-BA), compounds 2, 3, 4, 7, 9, and 12 could extend the seed germination period of Rhodiola tibetica up to the 11th day.

Unveiling the Structural Characteristics and Bioactivities of the Polysaccharides Extracted from Endophytic Penicillium sp.

Polysaccharides are abundantly present in fungi and are gaining recognition for their exceptional bioactivities. Hence, the present study aimed to extract intracellular polysaccharides (IPS-1 and IPS-2) from the endophytic Penicillium radiatolobatum and compare their physicochemical and bioactive attributes. The monosaccharide composition analysis revealed the existence of galactose, glucose, and mannose in both the IPS, while a trace amount of xylose was found in IPS-1. Further, FT-IR, 1H NMR, and 13C NMR analysis suggested that the IPS-2 was mainly composed of the β-(1→4)-D-Galactose and β-(1→4)-D-Glucose as the main chain, with the β-(1→6)-D-mannose as branched chains. Compared to IPS-1, the IPS-2 showed higher antioxidant activities with an IC50 value of 108 ± 2.5 μg/mL, 272 ± 4.0 μg/mL, and 760 ± 5.0 μg/mL for ABTS+ scavenging, DPPH radical scavenging, and ferric reducing power, respectively. In addition, the IPS-2 inhibited the viability of prostate cancer (PC-3) cells (IC50; 435 ± 3.0 μg/mL) via apoptosis associated with mitochondrial membrane potential collapse and altered morphological features, which was revealed by cellular staining and flow cytometric analysis. Moreover, no apparent cytotoxic effects were seen in IPS-2-treated (1000 μg/mL) non-cancerous cells (HEK-293 and NIH3T3). Overall, the findings of this study suggest that P. radiatolobatum could be a potent source of polysaccharides with promising antioxidant and anticancer activity.

Root-priming with the extract of endophytic Penicillium sp. PM031 at a non-toxic concentration evokes resistance in its wilt-susceptible host tomato against Ralstonia solanacearum

Root-priming with the extract of endophytic Penicillium sp. PM031 at a non-toxic concentration evokes resistance in its wilt-susceptible host tomato against Ralstonia solanacearum

Ultraperformance liquid chromatography-based metabolite profiling and cytotoxic activity of the ethyl acetate extract of two endophytic Penicillium sp.

The present study evaluated the mycochemical abundance, and the cytotoxic and hemolytic activities of ethyl acetate extract (EAE) of endophytic Penicillium camponotum (PC) and Penicillium fuscoglaucum (PF). Higher yield was noted in EAE-PF with total phenols (26.59 ± 1.52 mg of GAE/g DW) and flavonoids (3.12 ± 1.83 mg of QE/g DW). The EAE-PF inhibited the proliferation of two breast cancer cells (BT-474 and MDA-MB-231) with the half-maximal inhibitory concentration (IC50) of 0.112 and 0.120 mg/mL, respectively, while the IC50 values against HEK-293 and NIH3T3 cells were not found up to 1 mg/mL dose of EAE-PF. Moreover, EAE-PF (1 mg/mL) demonstrated its trivial toxicity in erythrocytes with ∼4.6% of hemolysis. The metabolic profiling of EAE-PF revealed the presence of mycochemicals including penicitide B (C18H34O5), p-hydroxyphenethyl anisate (C16H16O4), and dihydroxystearic acid (C18H36O4). Furthermore, these compounds exhibited substantial interactions with human cancer-related proteins such as epidermal growth factor receptor (EGFR), N-myristoyltransferase isoform 2 (NMT-2), cyclin-dependent kinase 2 (CDK-2), and c-mesenchymal epithelial transition factor kinase (c-Met K) evidenced by in-silico molecular docking analysis. Overall, this report suggests further studies on the isolation and purification of novel anti-cancer compounds from endophytic PF.

Polyketides with anti-inflammatory activity isolated from Rhodiola tibetica endophytic fungus Penicillium sp. HJT-A-10

Seven undescribed polyketide compounds (1–4, 9–11) and six known polyketide compounds (5–8,12, 13) were isolated from Rhodiola tibetica endophytic Penicillium sp. HJT-A-10. The structural of seven undescribed polyketides metabolites were established on the basis of spectroscopic methods. The results of anti-inflammatory activity showed that compounds 1–8，10–13 had significant inhibitory effects on LPS-induced NO production in RAW 264.7 cells.

Penisarins A and B, Sesquiterpene Coumarins Isolated from an Endophytic Penicillium sp.

Penisarins A (1) and B (2), sesquiterpene coumarins with an unusual tricyclic sesquiterpene system, were isolated from endophytic Penicillium sp. KMU18029. Their structures were elucidated on the basis of spectroscopic methods, single-crystal X-ray diffraction, and electronic circular dichroism calculations. Compound 2 showed significant cytotoxicities against two human cancer cell lines, HL-60 and SMMC-7721, with IC50 values of 3.6 ± 0.2 and 3.7 ± 0.2 μM, respectively.

The interactions between endophytic Penicillium sp. Y2 and host plant Artemisia annua L.

The interactions between endophytic Penicillium sp. Y2 and host plant Artemisia annua L.

Penicisochromans from the endophytic fungus Penicillium sp. BCC18034

Eight new substances including penicisochromans F–L, and penicibenzoxepinol along with seven known substances were isolated from the endophytic Penicillium sp. BCC18034. Their chemical structures were determined based on 1D and 2D NMR spectroscopic data and HR-ESI-MS analyses. Biological activities against Plasmodium falciparum, MCF-7, NCI-H187, and Vero cells of the isolated compounds were also reported.

Penicolinates A–E from endophytic Penicillium sp. BCC16054

Five new picolinic acid derivatives, penicolinates A–E (1–5), together with four known compounds including phenopyrrozin (6), p-hydroxyphenopyrrozin (7), gliotoxin (8), and bisdethiobis(methylthio)gliotoxin (9) were isolated from endophytic Penicillium sp. BCC16054. The chemical structures were established from spectroscopic data-1D and 2D NMR experiments, IR, UV, and HRESIMS. These compounds were evaluated for antimalarial and antitubercular activities and for their activity against Bacillus cereus and Candida albicans along with cytotoxicity against both cancerous and non-cancerous cells.

Two new chroman derivations from the endophytic Penicillium sp. DCS523.

Strain DCS523 was isolated from the branch tissue of Daphniphyllum longeracemosum and determined to be a Penicillium sp. according to the ITS sequence analysis. The extracts from the PDA solid fermentation media of Penicillium sp. DCS523 were purified to give two new chroman derivatives as well as six known compounds. Based on their spectral data the new compounds were identified as (Z)-6-acetyl- 3-(1,2-dihydroxypropylidene)-5-hydroxy-8-methylchroman-2-one (1) and 6-acetyl-2α,5- dihydroxy-2-(2-hydroxypropyl)- 3α,8-dimethylchroman (2), respectively.