scholarly journals Rhinoclactones A-E, Resorcylic Acid Analogs from Desert Plant Endophytic Fungus Rhinocladiella similis

Molecules ◽  
2019 ◽  
Vol 24 (7) ◽  
pp. 1405 ◽  
Author(s):  
Luying Li ◽  
Xiaoyan Zhang ◽  
Xiangmei Tan ◽  
Bingda Sun ◽  
Bin Wu ◽  
...  
Keyword(s):  
Endophytic Fungus ◽  
Cytotoxic Activities ◽  
Desert Plant ◽  
Ionization Mass ◽  
X Ray Diffraction ◽  
Nmr Data ◽  
The Common ◽  
Resorcylic Acid Lactones ◽  
New Compounds ◽  
Modified Mosher’S Method

Seven resorcylic acid lactones (RALs) including five new analog rhinoclactones, A–E (1, 2, 4–6), were isolated from an endophytic fungus Rhinocladiella similis in the plant Agriophyllum squarrosum collected from the Tengger Desert of the Ningxia Province, China. The structures of these new compounds were determined by HR-ESI-MS (High Resolution Electrospray Ionization Mass Spectrometry), NMR data, modified Mosher’s method, and X-ray diffraction experiments. All compounds isolated from this fungus possessed the 16-OMe/14-OH, not the common 16-OH/14-OH or 16-OH/14-OMe groups on the aromatic ring, which are rarely found in nature. Compound 7 displayed cytotoxic activities against HCT116 and HeLa cancer cell lines. The possible biosynthesis of 1–7 is suggested, and the potential ecological roles of these fungal secondary metabolites is discussed.

scholarly journals Polyketide Derivatives from Mangrove Derived Endophytic Fungus Pseudopestalotiopsis theae

Marine Drugs ◽  
2020 ◽  
Vol 18 (2) ◽  
pp. 129 ◽  
Author(s):  
Xiaoqin Yu ◽  
Werner E. G. Müller ◽  
Dieter Meier ◽  
Rainer Kalscheuer ◽  
Zhiyong Guo ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Endophytic Fungus ◽  
2D Nmr ◽  
Drug Resistant ◽  
Lymphoma Cell Line ◽  
Nmr Data ◽  
Ic50 Value ◽  
New Compounds ◽  
Modified Mosher’S Method ◽  
Mouse Lymphoma

Chemical investigation of secondary metabolites from the endophytic fungus Pseudopestalotiopsis theae led to the isolation of eighteen new polyketide derivatives, pestalotheols I–Q (1–9) and cytosporins O–W (15–23), together with eight known analogs (10–14 and 24–26). The structures of the new compounds were elucidated by HRMS and 1D and 2D NMR data, as well as by comparison with literature data. Modified Mosher’s method was applied to determine the absolute configuration of some compounds. Compound 23 showed significant cytotoxicity against the mouse lymphoma cell line L5178Y with an IC50 value of 3.0 μM. Furthermore, compounds 22 and 23 showed moderate antibacterial activity against drug-resistant Acinetobacter baumannii (ATCC BAA-1605) in combination with sublethal colistin concentrations.

scholarly journals Two New Cytotoxic Compounds from a Deep-Sea Penicillum citreonigrum XT20-134

Marine Drugs ◽  
2019 ◽  
Vol 17 (9) ◽  
pp. 509 ◽  
Author(s):  
Xi-Xiang Tang ◽  
Shun-Zhi Liu ◽  
Xia Yan ◽  
Bo-Wen Tang ◽  
Mei-Juan Fang ◽  
...  
Keyword(s):  
Tumor Cell ◽  
Deep Sea ◽  
Cytotoxic Activities ◽  
Ionization Mass ◽  
Human Hepatoma ◽  
Etoac Extract ◽  
Deep Sea Sediment ◽  
Cytotoxic Compounds ◽  
Ic50 Values ◽  
New Compounds

Penicillum citreonigrum XT20-134 (MCCC 3A00956) is a fungus with cytotoxic activity, derived from deep-sea sediment. Five new compounds, adeninylpyrenocine (1), 2-hydroxyl-3-pyrenocine-thio propanoic acid (2), ozazino-cyclo-(2,3-dihydroxyl-trp-tyr) (3), 5,5-dichloro-1-(3,5-dimethoxyphenyl)-1,4-dihydroxypentan-2-one (4), and 2,3,4-trihydroxybutyl cinnamate (5), together with 19 known compounds (6–24), were isolated from an ethyl acetate (EtOAc) extract of its fermentation. The structures of the new compounds were comprehensively characterized by high-resolution electrospray ionization-mass spectrometry (HR-ESI-MS), 1D and 2D nuclear magnetic resonance (NMR). All isolates were evaluated for their cytotoxic activities. The heteroatom-containing new compounds 2 and 4 showed potent cytotoxicity to the human hepatoma tumor cell Bel7402 with IC50 values of 7.63 ± 1.46, 13.14 ± 1.41 μM and the human fibrosarcoma tumor cell HT1080 with IC50 values of 10.22 ± 1.32, 16.53 ± 1.67 μM, respectively.

scholarly journals Microbial Transformation of neo-Clerodane Diterpenoid, Scutebarbatine F, by Streptomyces sp. CPCC 205437

2021 ◽  
Vol 12 ◽  
Author(s):  
Dewu Zhang ◽  
Xiaoyu Tao ◽  
Guowei Gu ◽  
Yujia Wang ◽  
Wenxia Zhao ◽  
...  
Keyword(s):  
Influenza A ◽  
Microbial Transformation ◽  
Cancer Cell Line ◽  
Antibacterial Activities ◽  
Positive Control ◽  
Cytotoxic Activities ◽  
Ionization Mass ◽  
Nmr Data ◽  
First Time ◽  
New Metabolites

Biotransformation of the neo-clerodane diterpene, scutebarbatine F (1), by Streptomyces sp. CPCC 205437 was investigated for the first time, which led to the isolation of nine new metabolites, scutebarbatine F1–F9 (2–10). Their structures were determined by extensive high-resolution electrospray ionization mass spectrometry (HRESIMS) and NMR data analyses. The reactions that occurred included hydroxylation, acetylation, and deacetylation. Compounds 2–4 and 8–10 possess 18-OAc fragment, which were the first examples of 13-spiro neo-clerodanes with 18-OAc group. Compounds 7–10 were the first report of 13-spiro neo-clerodanes with 2-OH. Compounds 1–10 were biologically evaluated for the cytotoxic, antiviral, and antibacterial activities. Compounds 5, 7, and 9 exhibited cytotoxic activities against H460 cancer cell line with inhibitory ratios of 46.0, 42.2, and 51.1%, respectively, at 0.3 μM. Compound 5 displayed a significant anti-influenza A virus activity with inhibitory ratio of 54.8% at 20 μM, close to the positive control, ribavirin.

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

Marine Drugs ◽  
2021 ◽  
Vol 19 (9) ◽  
pp. 483
Author(s):  
Kuo Yong ◽  
Sidra Kaleem ◽  
Bin Wu ◽  
Zhizhen Zhang
Keyword(s):  
Chemical Degradation ◽  
Ionization Mass ◽  
X Ray Diffraction ◽  
Penicillium Sp ◽  
Electrospray Ionization Mass Spectroscopy ◽  
Ionization Mass Spectroscopy ◽  
Ic50 Values ◽  
Rice Medium ◽  
Antiglioma Activity ◽  
New Compounds

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.

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.

scholarly journals Correction to Bioactive Resorcylic Acid Lactones with Different Ring Systems from Desert Plant Endophytic Fungus Chaetosphaeronema hispidulum

2019 ◽  
Vol 67 (15) ◽  
pp. 4393-4393
Author(s):  
Xiao-Yan Zhang ◽  
Zhen-Liang Liu ◽  
Bing-Da Sun ◽  
Shu-Bin Niu ◽  
Meng-Hua Wang ◽  
...  
Keyword(s):  
Endophytic Fungus ◽  
Desert Plant ◽  
Ring Systems ◽  
Resorcylic Acid Lactones

scholarly journals Azaphilones from the Red Sea Fungus Aspergillus falconensis

Marine Drugs ◽  
2020 ◽  
Vol 18 (4) ◽  
pp. 204 ◽  
Author(s):  
Dina H. El-Kashef ◽  
Fadia S. Youssef ◽  
Rudolf Hartmann ◽  
Tim-Oliver Knedel ◽  
Christoph Janiak ◽  
...  
Keyword(s):  
Red Sea ◽  
Cancer Cell Line ◽  
2D Nmr ◽  
X Ray Diffraction ◽  
2D Nmr Spectroscopy ◽  
Nmr Data ◽  
Ic50 Values ◽  
Rice Medium ◽  
Optical Rotations ◽  
New Compounds

The marine-derived fungus Aspergillus falconensis, isolated from sediment collected from the Canyon at Dahab, Red Sea, yielded two new chlorinated azaphilones, falconensins O and P (1 and 2) in addition to four known azaphilone derivatives (3−6) following fermentation of the fungus on solid rice medium containing 3.5% NaCl. Replacing NaCl with 3.5% NaBr induced accumulation of three additional new azaphilones, falconensins Q−S (7−9) including two brominated derivatives (7 and 8) together with three known analogues (10−12). The structures of the new compounds were elucidated by 1D and 2D NMR spectroscopy and HRESIMS data as well as by comparison with the literature. The absolute configuration of the azaphilone derivatives was established based on single-crystal X-ray diffraction analysis of 5, comparison of NMR data and optical rotations as well as on biogenetic considerations. Compounds 1, 3−9, and 11 showed NF-κB inhibitory activity against the triple negative breast cancer cell line MDA-MB-231 with IC50 values ranging from 11.9 to 72.0 µM.

Bioactive Resorcylic Acid Lactones with Different Ring Systems from Desert Plant Endophytic Fungus Chaetosphaeronema hispidulur

2018 ◽  
Vol 66 (34) ◽  
pp. 8976-8982 ◽  
Author(s):  
Xiao-Yan Zhang ◽  
Zhan-Liang Liu ◽  
Bing-Da Sun ◽  
Shu-Bin Niu ◽  
Meng-Hua Wang ◽  
...  
Keyword(s):  
Endophytic Fungus ◽  
Desert Plant ◽  
Ring Systems ◽  
Resorcylic Acid Lactones

scholarly journals Roussoelins A and B: two phenols with antioxidant capacity from ascidian-derived fungus Roussoella siamensis SYSU-MS4723

2020 ◽  
Author(s):  
Senhua Chen ◽  
Hongjie Shen ◽  
Yanlian Deng ◽  
Heng Guo ◽  
Minghua Jiang ◽  
...  
Keyword(s):  
Conformational Analysis ◽  
Antioxidant Capacity ◽  
Structural Properties ◽  
Coupling Constants ◽  
Bioactive Molecules ◽  
Active Metabolites ◽  
Nmr Data ◽  
Pharmacologically Active ◽  
New Compounds ◽  
Modified Mosher’S Method

Abstract Ascidian-derived microorganisms are a significant source of pharmacologically active metabolites with interesting structural properties. When discovering bioactive molecules from ascidian-derived fungi, two new phenols, roussoelins A (1) and B (2), and ten known polyketides (3–12) were isolated from the ascidian-derived fungus Roussoella siamensis SYSU-MS4723. The planar structure of compounds 1 and 2 was established by analysis of HR-ESIMS and NMR data. The conformational analysis of the new compounds was assigned according to coupling constants and selective gradient NOESY experiments, and absolute configurations were completed by the modified Mosher’s method. Among the isolated compounds, 1, 2, and 9 showed moderate antioxidant capacity. Graphical abstract

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.

Sign in / Sign up

Export Citation Format

Share Document