scholarly journals Antimicrobial Meroterpenoids and Erythritol Derivatives Isolated from the Marine-Algal-Derived Endophytic Fungus Penicillium chrysogenum XNM-12

Marine Drugs ◽  
2020 ◽  
Vol 18 (11) ◽  
pp. 578
Author(s):  
Kuo Xu ◽  
Xu-Lun Wei ◽  
Lin Xue ◽  
Zhong-Feng Zhang ◽  
Peng Zhang
Keyword(s):  
Plant Pathogen ◽  
Endophytic Fungus ◽  
Penicillium Chrysogenum ◽  
2D Nmr ◽  
Antimicrobial Activities ◽  
Penicillium Species ◽  
Pyrone Ring ◽  
Planar Structures ◽  
Marine Algal ◽  
Optical Rotations

One new meroterpenoid-type alkaloid, oxalicine C (1), and two new erythritol derivatives, penicierythritols A (6) and B (7), together with four known meroterpenoids (2–5), were isolated from the marine algal-derived endophytic fungus Penicillium chrysogenum XNM-12. Their planar structures were determined by means of spectroscopic analyses, including UV, 1D and 2D NMR, and HRESIMS spectra. Their stereochemical configurations were established by comparing the experimental and calculated electronic circular dichroism (ECD) spectra for compound 1, as well as by comparison of the optical rotations with literature data for compounds 6 and 7. Notably, oxalicine C (1) represents the first example of an oxalicine alkaloid with a cleaved α-pyrone ring, whereas penicierythritols A (6) and B (7) are the first reported from the Penicillium species. The antimicrobial activities of compounds 1–7 were evaluated. Compounds 1 and 6 exhibited moderate antibacterial effects against the plant pathogen Ralstonia solanacearum with minimum inhibitory concentration (MIC) values of 8 and 4 μg/mL, respectively. Compound 6 also possesses moderate antifungal properties against the plant pathogen Alternaria alternata with a MIC value of 8 μg/mL.

scholarly journals Polyketides from the Mangrove-Derived Endophytic Fungus Cladosporium cladosporioides

Marine Drugs ◽  
2019 ◽  
Vol 17 (5) ◽  
pp. 296 ◽  
Author(s):  
Fan-Zhong Zhang ◽  
Xiao-Ming Li ◽  
Xin Li ◽  
Sui-Qun Yang ◽  
Ling-Hong Meng ◽  
...  
Keyword(s):  
Pathogenic Fungi ◽  
2D Nmr ◽  
Antimicrobial Activities ◽  
Cladosporium Cladosporioides ◽  
X Ray Diffraction ◽  
Bruguiera Gymnorrhiza ◽  
Mangrove Plant ◽  
Spectrometric Data ◽  
Ic50 Value ◽  
Optical Rotations

Five new polyketides, namely, 5R-hydroxyrecifeiolide (1), 5S-hydroxyrecifeiolide (2), ent-cladospolide F (3), cladospolide G (4), and cladospolide H (5), along with two known compounds (6 and 7), were isolated from the endophytic fungal strain Cladosporium cladosporioides MA-299 that was obtained from the leaves of the mangrove plant Bruguiera gymnorrhiza. The structures of these compounds were established by extensive analysis of 1D/2D NMR data, mass spectrometric data, ECDs and optical rotations, and modified Mosher’s method. The structures of 3 and 6 were confirmed by single-crystal X-ray diffraction analysis and this is the first time for reporting the crystal structures of these two compounds. All of the isolated compounds were examined for antimicrobial activities against human and aquatic bacteria and plant pathogenic fungi as well as enzymatic inhibitory activities against acetylcholinesterase. Compounds 1–4, 6, and 7 exhibited antimicrobial activity against some of the tested strains with MIC values ranging from 1.0 to 64 μg/mL, while 3 exhibited enzymatic inhibitory activity against acetylcholinesterase with the IC50 value of 40.26 μM.

scholarly journals Simplicilones A and B Isolated from the Endophytic Fungus Simplicillium subtropicum SPC3

Antibiotics ◽  
2020 ◽  
Vol 9 (11) ◽  
pp. 753
Author(s):  
Elodie Gisèle M. Anoumedem ◽  
Bel Youssouf G. Mountessou ◽  
Simeon F. Kouam ◽  
Abolfazl Narmani ◽  
Frank Surup
Keyword(s):  
Endophytic Fungus ◽  
2D Nmr ◽  
In Vitro Cytotoxicity ◽  
Coupling Constants ◽  
Broth Culture ◽  
Spectroscopic Techniques ◽  
Cytotoxic Effects ◽  
Relative Configuration ◽  
Planar Structures

Two new tetracyclic polyketides with a spirocenter, simplicilones A (1) and B (2) were isolated from the broth-culture of the endophytic fungus Simplicilliumsubtropicum (SPC3) in the course of our screening for new bioactive secondary metabolites. This endophytoic fungus is naturally harboured in the fresh bark of the Cameroonian medicinal plant Duguetia staudtii (Engl. and Diels) Chatrou. The planar structures of the simplicilones were elucidated by MS and 1D as well as 2D NMR spectroscopic techniques. The relative configuration was assigned by NOESY experiments in conjunction with coupling constants; subsequently, the absolute configurations were assigned by the modified Mosher’s method. The compounds showed weak cytotoxic effects against the cell line KB3.1 (in vitro cytotoxicity (IC50) = 25 µg/mL for 1, 29 µg/mL for 2), but were inactive against the tested Gram-positive and Gram-negative bacteria as well as fungi.

scholarly journals Chrysoxanthones A–C, Three New Xanthone–Chromanone Heterdimers from Sponge-Associated Penicillium chrysogenum HLS111 Treated with Histone Deacetylase Inhibitor

Marine Drugs ◽  
2018 ◽  
Vol 16 (10) ◽  
pp. 357 ◽  
Author(s):  
Xin Zhen ◽  
Ting Gong ◽  
Yan-Hua Wen ◽  
Dao-Jiang Yan ◽  
Jing-Jing Chen ◽  
...  
Keyword(s):  
Bacillus Subtilis ◽  
Histone Deacetylase ◽  
Histone Deacetylase Inhibitor ◽  
Penicillium Chrysogenum ◽  
Inhibitory Concentration ◽  
2D Nmr ◽  
Antibacterial Activities ◽  
Planar Structures ◽  
Spectroscopic Analyses ◽  
Deacetylase Inhibitor

By treating with histone-deacetylase inhibitor valproate sodium, three new heterdimeric tetrahydroxanthone–chromanone lactones chrysoxanthones A–C (1–3), along with 17 known compounds were isolated from a sponge-associated Penicillium chrysogenum HLS111. The planar structures of chrysoxanthones A–C were elucidated by means of spectroscopic analyses, including MS, 1D, and 2D NMR. Their absolute configurations were established by electronic circular dichroism (ECD) calculations. Chrysoxanthones A–C exhibited moderate antibacterial activities against Bacillus subtilis with minimum inhibitory concentration (MIC) values of 5–10 μg/mL.

scholarly journals Discovery of New Secondary Metabolites by Epigenetic Regulation and NMR Comparison from the Plant Endophytic Fungus Monosporascus eutypoides

Molecules ◽  
2020 ◽  
Vol 25 (18) ◽  
pp. 4192
Author(s):  
Zhe Guo ◽  
Zhong-Mei Zou
Keyword(s):  
Endophytic Fungus ◽  
2D Nmr ◽  
Chemical Diversity ◽  
Ionization Mass ◽  
Electrospray Ionization Mass Spectroscopy ◽  
Planar Structures ◽  
Ionization Mass Spectroscopy ◽  
Epigenetic Manipulation ◽  
New Compounds ◽  
Mcf 7

Overexpression of the histone acetyltransferase and the 1H NMR spectroscopic experiments of the endophytic fungus Monosporascus eutypoides resulted in the isolation of two new compounds, monosporasols A (1) and B (2), and two known compounds, pestaloficin C (3) and arthrinone (4). Their planar structures and absolute configurations were determined by spectroscopic analysis including high resolution electrospray ionization mass spectroscopy (HRESIMS), one-dimensional (1D) and two-dimensional (2D) NMR, and calculated electronic circular dichroism data. Compounds 1–2 were screened in cytotoxic bioassays against HeLa, HCT-8, A549 and MCF-7 cells. Our work highlights the enormous potential of epigenetic manipulation along with the NMR comparison as an effective strategy for unlocking the chemical diversity encoded by fungal genomes.

Two new glycosidal metabolites of endophytic fungus Penicillium sp. (NO.4) from Tapiscia sinensis

2016 ◽  
Vol 71 (4) ◽  
pp. 283-286 ◽  
Author(s):  
Qiao Wan ◽  
Ziwei Feng ◽  
Xueshuang Li ◽  
Mengmeng Lv ◽  
Zhiyong Guo ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Cell Lines ◽  
Cancer Cell ◽  
Endophytic Fungus ◽  
Cancer Cell Line ◽  
2D Nmr ◽  
Cancer Cell Lines ◽  
Antimicrobial Activities ◽  
Cytotoxic Activities ◽  
A549 Cancer Cell Line

AbstractTwo new glycosides, 8-O-β-d-glucopyranosyl-6-methyl-1-carboxylate methyl ester xanthone (1) and 4′-O-β-d-galactopyranosyl djalonensone (2), together with four known compounds, 8-hydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate methyl ester (3), cassionllin (4), djalonensone (5) and alternariol (6), were isolated from the endophytic fungus Penicillium sp. (NO.4) of Tapiscia sinensis Oliv. The structures of compounds 1–6 were elucidated by the analysis of 1D and 2D NMR and HRMS. The cytotoxic activities of these compounds were evaluated against four cancer cell lines, as well as antimicrobial activities against two plant-pathogenic microbes. Compounds 1–6 showed moderate cytotoxicity against the A549 cancer cell line with IC50 values ranging from 6.8 to 35.8 μg mL−1 and were found to be inactive against three other cancer cell lines MCF-7, Caski and Hep G-2.

scholarly journals Benzophenone Derivatives from an Algal-Endophytic Isolate of Penicillium chrysogenum and Their Cytotoxicity

Molecules ◽  
2018 ◽  
Vol 23 (12) ◽  
pp. 3378 ◽  
Author(s):  
Dong-Lin Zhao ◽  
Xiao-Long Yuan ◽  
Yong-Mei Du ◽  
Zhong-Feng Zhang ◽  
Peng Zhang
Keyword(s):  
Penicillium Chrysogenum ◽  
Density Functional ◽  
2D Nmr ◽  
Coupling Constants ◽  
Grateloupia Turuturu ◽  
Functional Theory ◽  
Drug Candidates ◽  
Ic50 Values ◽  
Marine Algal ◽  
New Compounds

Chromatographic separation of a marine algal-derived endophytic fungus Penicillium chrysogenum AD-1540, which was isolated from the inner tissue of the marine red alga Grateloupia turuturu, yielded two new benzophenone derivatives, chryxanthones A and B (compounds 1 and 2, respectively). Their structures were undoubtedly determined by comprehensive analysis of spectroscopic data (1D/2D NMR and HRESIMS). The relative and absolute configurations were assigned by analysis of the coupling constants and time-dependent density functional theory (TDDFT) calculations of their electronic circular dichroism (ECD) spectra, respectively. Both compounds possessed an unusual dihydropyran ring (ring D) fused to an aromatic ring, rather than the commonly occurring prenyl moiety, and a plausible biosynthetic pathway was postulated. The cytotoxicities of compounds 1 and 2 were evaluated against six human cell lines, and both of the compounds demonstrated weak to moderate cytotoxicities with IC50 values ranging from 20.4 to 46.4 μM. These new compounds further demonstrate the potential of marine-derived fungi as an untapped source of pharmaceutical components with unique properties that could be developed as drug candidates.

scholarly journals Prenylated Diphenyl Ethers from the Marine Algal-Derived Endophytic Fungus Aspergillus tennesseensis

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2368 ◽  
Author(s):  
Zhao-Xia Li ◽  
Xiu-Fang Wang ◽  
Guang-Wei Ren ◽  
Xiao-Long Yuan ◽  
Ning Deng ◽  
...  
Keyword(s):  
Endophytic Fungus ◽  
Diphenyl Ether ◽  
Antimicrobial Activities ◽  
Cytotoxic Activities ◽  
Ic50 Value ◽  
Diphenyl Ethers ◽  
Marine Algal ◽  
Spectroscopy Studies ◽  
New Compounds

Considerable attention has been paid to marine derived endophytic fungi, owing to their capacity to produce novel secondary metabolites with potent bioactivities. In this study, two new compounds with a prenylated diphenyl ether structure—diorcinol L (1) and (R)-diorcinol B (2)—were isolated from the marine algal-derived endophytic fungus Aspergillus tennesseensis, along with seven known compounds: (S)-diorcinol B (3), 9-acetyldiorcinol B (4), diorcinol C (5), diorcinol D (6), diorcinol E (7), diorcinol J (8), and a dihydrobenzofuran derivative 9. Their structures were elucidated by extensive NMR spectroscopy studies. Compound 2 represents the first example of an R-configuration in the prenylated moiety. All these isolated compounds were examined for antimicrobial and cytotoxic activities. Compounds 1–9 exhibited antimicrobial activities against some human- and plant-pathogenic microbes with MIC values ranging from 2 to 64 μg/mL. Moreover, compound 9 displayed considerable inhibitory activity against the THP-1 cell line in vitro, with an IC50 value of 7.0 μg/mL.

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

Marine Drugs ◽  
2021 ◽  
Vol 19 (8) ◽  
pp. 416
Author(s):  
Xiaoshuang Gou ◽  
Danmei Tian ◽  
Jihua Wei ◽  
Yihan Ma ◽  
Yixue Zhang ◽  
...  
Keyword(s):  
Nitric Oxide ◽  
Biological Activities ◽  
2D Nmr ◽  
Positive Control ◽  
Inhibitory Effects ◽  
Penicillium Sp ◽  
Planar Structures ◽  
Anti Inflammatory ◽  
Optical Rotations ◽  
Oxide Synthase

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.

Rhytidhyesters A – D, 4 New Chlorinated Cyclopentene Derivatives from the Endophytic Fungus Rhytidhysteron sp. BZM-9

Planta Medica ◽  
2021 ◽  
Author(s):  
Sha Zhang ◽  
Wenxuan Wang ◽  
Jianbin Tan ◽  
Fenghua Kang ◽  
Dekun Chen ◽  
...  
Keyword(s):  
Endophytic Fungus ◽  
Human Colon ◽  
2D Nmr ◽  
Crystallographic Analysis ◽  
Cytotoxic Activities ◽  
Human Colon Cancer ◽  
X Ray ◽  
Planar Structures ◽  
Colon Cancer Cell Lines ◽  
Ic50 Values

AbstractFour new chlorinated cyclopentene derivatives, rhytidhyesters A – D (1 – 4), were isolated from Rhytidhysteron sp. BZM-9, an endophytic fungus from Leptospermum brachyandrum. The planar structures of compounds 1 – 4 were mainly elucidated by 1D, 2D NMR, and HRESIMS data. Their absolute configurations were established by X-ray crystallographic analysis, quantum chemical 13C NMR, and electronic circular dichroism calculations. Compounds 1 and 2 are a pair of epimers. Moreover, all the isolated compounds were evaluated for cytotoxic activities against 3 human colon cancer cell lines (SW620, HT29, SW480) and antimicrobial activity against Staphylococcus aureus. All compounds exhibited weak to moderate antiproliferative activities with IC50 values ranging from 15.4 to 37.7 µM but were inactive against S. aureus.

scholarly journals New Enantiomers of a Nor-Bisabolane Derivative and Two New Phthalides Produced by the Marine-Derived Fungus Penicillium chrysogenum LD-201810

2021 ◽  
Vol 12 ◽  
Author(s):  
Yan Ge ◽  
Wen-Li Tang ◽  
Qing-Rong Huang ◽  
Mao-Lian Wei ◽  
You-Zhi Li ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Penicillium Chrysogenum ◽  
Optical Resolution ◽  
Alternaria Solani ◽  
2D Nmr ◽  
Chiral Hplc ◽  
Excellent Activity ◽  
Marine Algal ◽  
Detailed Interpretation ◽  
Mcf 7

Marine-derived fungi are a treasure house for the discovery of structurally novel secondary metabolites with potential pharmaceutical value. In this study, a pair of new nor-bisabolane derivative enantiomers (±)−1 and two new phthalides (4 and 5), as well as four known metabolites, were isolated from the culture filtrate of the marine algal-derived endophytic fungus Penicillium chrysogenum LD-201810. Their structures were established by detailed interpretation of spectroscopic data (1D/2D NMR and ESI-MS). The optical resolution of compound (±)−1 by chiral HPLC successfully afforded individual enantiomers (+)−1 and (−)−1, and their absolute configurations were determined by TDDFT-ECD calculations. Compound (±)−1 represents the first example of bisabolane analogs with a methylsulfinyl substituent group, which is rare in natural products. All of the isolated compounds 1–7 were evaluated for their cytotoxic activity against A549, BT-549, HeLa, HepG2, MCF-7, and THP-1 cell lines, as well as for antifungal activity against four plant pathogenetic fungi (Alternaria solani, Botrytis cinerea, Fusarium oxysporum, and Valsa mali). Compound 2, a bisabolane-type sesquiterpenoid, was shown to possess excellent activity for control of B. cinerea with half-maximal inhibitory concentration (IC50) of 13.6 μg/mL, whereas the remaining investigated compounds showed either weak or no cytotoxic/antifungal activity in this study.

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