scholarly journals An Unusual Benzoisoquinoline-9-one Derivative and Other Related Compounds with Antiproliferative Activity from Hawaiian Endophytic Fungus Peyronellaea sp. FT431

Molecules ◽  
2019 ◽  
Vol 24 (1) ◽  
pp. 196 ◽  
Author(s):  
Chunshun Li ◽  
Ariel M. Sarotti ◽  
Xiaohua Wu ◽  
Baojun Yang ◽  
James Turkson ◽  
...  
Keyword(s):  
Endophytic Fungus ◽  
Human Kidney ◽  
Carcinoma Cells ◽  
Cytotoxic Activities ◽  
Adenocarcinoma Cells ◽  
Indigenous Plant ◽  
Ic50 Values ◽  
Human Ovarian Carcinoma ◽  
New Compounds ◽  
Related Compounds

A new polyketide containing the benzoisoquinoline-9-one moiety, peyronetide A (1), and three other new derivatives peyronetides B–D (2–4), as well as one known compound (5) were purified from the cultured broth of the endophytic fungus Peyronellaea sp. FT431, which was isolated from the Hawaiian indigenous plant, Verbena sp. The structures of the new compounds were determined through the analysis of HRMS and NMR spectroscopic data. Compounds 1, 2, and 5 showed cytotoxic activities against TK-10 (human kidney adenocarcinoma cells), cisplatin sensitive A2780S (human ovarian carcinoma cells), and cisplatin resistant A2780CisR cell lines, with IC50 values between 6.7 to 29.2 μM.

scholarly journals Cryptic Secondary Metabolites from the Sponge-Associated Fungus Aspergillus ochraceus

Marine Drugs ◽  
2019 ◽  
Vol 17 (2) ◽  
pp. 99 ◽  
Author(s):  
Marian Frank ◽  
Ferhat Özkaya ◽  
Werner Müller ◽  
Alexandra Hamacher ◽  
Matthias Kassack ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Carcinoma Cells ◽  
Aspergillus Ochraceus ◽  
Nitrobenzoic Acid ◽  
Ovarian Carcinoma Cells ◽  
White Bean ◽  
Ic50 Values ◽  
Rice Medium ◽  
Human Ovarian Carcinoma ◽  
New Compounds

The fungus Aspergillus ochraceus was isolated from the Mediterranean sponge Agelas oroides. The initial fermentation of the fungus on solid rice medium yielded 16 known compounds (4–19). The addition of several inorganic salts to the rice medium mainly influenced the accumulation of these secondary metabolites. Fermentation of the fungus on white bean medium yielded the new waspergillamide B (1) featuring an unusual p-nitrobenzoic acid as partial structure. Moreover, two new compounds, ochraspergillic acids A and B (2 and 3), which are both adducts of dihydropenicillic acid and o- or p-aminobenzoic acid, were isolated from the co-culture of the fungus with Bacillus subtilis. Compound 2 was also detected in axenic fungal cultures following the addition of either anthranilic acid or tryptophan to the rice medium. The structures of the new compounds were established by 1D and 2DNMR experiments as well as from the HRMS data. The absolute configuration of 1 was elucidated following hydrolysis and derivatization of the amino acids using Marfey’s reagent. Viomellein (9) and ochratoxin B (18) exhibited strong cytotoxicity against the A2780 human ovarian carcinoma cells with IC50 values of 5.0 and 3.0 µM, respectively.

scholarly journals Perylenequione Derivatives with Anticancer Activities Isolated from the Marine Sponge-Derived Fungus, Alternaria sp. SCSIO41014

Marine Drugs ◽  
2018 ◽  
Vol 16 (8) ◽  
pp. 280 ◽  
Author(s):  
Xiaoyan Pang ◽  
Xiuping Lin ◽  
Pei Wang ◽  
Xuefeng Zhou ◽  
Bin Yang ◽  
...  
Keyword(s):  
Carcinoma Cells ◽  
Cytotoxic Activities ◽  
Anticancer Activities ◽  
Chiral Phase ◽  
Phenol Derivatives ◽  
Ic50 Value ◽  
Ic50 Values ◽  
Alternaria Sp ◽  
New Compounds ◽  
Hydroxy Groups

Seven new secondary metabolites classified as two perylenequinone derivatives (1 and 2), an altenusin derivative (3), two phthalide racemates (4 and 5), and two phenol derivatives (6 and 7), along with twenty-one known compounds (8–28) were isolated from cultures of the sponge-derived fungus, Alternaria sp. SCSIO41014. The structures and absolute configurations of these new compounds (1–7) were determined by spectroscopic analysis, X-ray single crystal diffraction, chiral-phase HPLC separation, and comparison of ECD spectra to calculations. Altertoxin VII (1) is the first example possessing a novel 4,8-dihydroxy-substituted perylenequinone derivative, while the phenolic hydroxy groups have commonly always substituted at C-4 and C-9. Compound 1 exhibited cytotoxic activities against human erythroleukemia (K562), human gastric carcinoma cells (SGC-7901), and hepatocellular carcinoma cells (BEL-7402) with IC50 values of 26.58 ± 0.80, 8.75 ± 0.13, and 13.11 ± 0.95 μg/mL, respectively. Compound 11 showed selectively cytotoxic activity against K562, with an IC50 value of 19.67 ± 0.19 μg/mL. Compound 25 displayed moderate inhibitory activity against Staphylococcus aureus with an MIC value of 31.25 μg/mL.

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 Cytotoxic Polyketides from the Marine Sponge-Derived Fungus Pestalotiopsis heterocornis XWS03F09

Molecules ◽  
2019 ◽  
Vol 24 (14) ◽  
pp. 2655 ◽  
Author(s):  
Lei ◽  
Lei ◽  
Zhou ◽  
Hu ◽  
Niu ◽  
...  
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Fermentation Broth ◽  
Human Cancer ◽  
Optical Rotation ◽  
Cytotoxic Activities ◽  
Human Cancer Cell Lines ◽  
Chemical Structures ◽  
Ic50 Values ◽  
New Compounds

Four new compounds, including two new polyketides, heterocornols M and N (1, 2), and a pair of epimers, heterocornols O and P (3, 4), were isolated from the fermentation broth of the marine sponge-derived fungus Pestalotiopsis heterocornis XWS03F09, together with three known compounds (5–7). The new chemical structures were established on the basis of a spectroscopic analysis, optical rotation, experimental and calculated electronic circular dichroism (ECD). All of the compounds (1–7) were evaluated for their cytotoxic activities, and heterocornols M-P (1–4) exhibited cytotoxicities against four human cancer cell lines with IC50 values of 20.4–94.2 μM.

scholarly journals LAMA-1: A Cerebroside Isolated from the Deep-Sea-Derived Fungus Penicillium chrysogenum

Metabolites ◽  
2020 ◽  
Vol 10 (2) ◽  
pp. 75
Author(s):  
Samah O. Alshehri ◽  
Rania T. Malatani ◽  
Hanin A. Bogari ◽  
Ahmad O. Noor ◽  
Amany K. Ibrahim ◽  
...  
Keyword(s):  
Cell Lines ◽  
Penicillium Chrysogenum ◽  
2D Nmr ◽  
Carcinoma Cells ◽  
Breast Adenocarcinoma ◽  
Cytotoxic Activities ◽  
Human Carcinoma ◽  
Sulforhodamine B ◽  
Ic50 Values ◽  
Hepg2 Cell Lines

Chemical investigation of the ethyl acetate extract of Penicillium chrysogenum strain S003, a fungus isolated from Red Sea deep sediment, led to the isolation of a cerebroside molecular species LAMA (1) along with three other known compounds, ergosterol (2), epidioxyergosterol (3), and kojic acid (4). The structures of the isolated compounds were elucidated by interpretation of spectral data, including detailed 1D and 2D NMR (One and two dimensional Nuclear Magnetic Resonance) and mass spectrometry. The cytotoxic activities of isolated compounds 1–4 against five human carcinoma cells were evaluated using sulforhodamine B (SRB) assay. Compounds 2 and 3 displayed promising cytotoxic profiles against lung cancer (A-549), prostate (DU-145), breast adenocarcinoma (MCF-7), and hepatocellular (HepG2) cell lines, with IC50 values of 21.26, 19.3; 1.50, 6.10; 16.95, 13.6; and 2.89, 3.07 µM, respectively, while they were inactive against HeLa cells. Compounds 1 and 4 showed weak cytotoxic profiles against all cell lines under investigation.

New Benzaldehyde and Benzopyran Compounds from the Endophytic Fungus Paraphaeosphaeria sp. F03 and Their Antimicrobial and Cytotoxic Activities

Planta Medica ◽  
2019 ◽  
Vol 85 (11/12) ◽  
pp. 957-964 ◽  
Author(s):  
Marcelo R. de Amorim ◽  
Felipe Hilário ◽  
Fernando M. dos Santos ◽  
João M. Batista ◽  
Tais M. Bauab ◽  
...  
Keyword(s):  
Endophytic Fungus ◽  
Inhibitory Concentration ◽  
High Resolution Mass Spectrometry ◽  
Mass Spectrometry Analysis ◽  
Racemic Mixture ◽  
Cytotoxic Activities ◽  
Spectrometry Analysis ◽  
Ic50 Values ◽  
Benzaldehyde Derivatives ◽  
Mcf 7

AbstractThree new benzaldehyde derivatives, sporulosaldeins A – C (1–3), and 3 new benzopyran derivatives, sporulosaldeins D – F (4–6), were discovered from an endophytic fungus, Paraphaeosphaeria sp. F03, which was isolated from Paepalanthus planifolius leaves. Compounds 1–6 were elucidated by 1- and 2-dimensional nuclear magnetic resonance experiments and high-resolution mass spectrometry analysis. The absolute configuration of compound 5 was determined through the comparison of experimental and calculated electronic circular dichroism data. Compounds 1–6 were found to exhibit antifungal activity with minimum inhibitory concentration (MIC) values of 7.8 – 250 µg/mL and racemic mixture of compound 6 exhibited weak cytotoxicity against MCF-7 and LM3 with IC50 values of 34.4 and 39.2 µM, respectively.

scholarly journals New Cardenolides from Biotransformation of Gitoxigenin by the Endophytic Fungus Alternaria eureka 1E1BL1: Characterization and Cytotoxic Activities

Molecules ◽  
2021 ◽  
Vol 26 (10) ◽  
pp. 3030
Author(s):  
Erdal Bedir ◽  
Çiğdem Karakoyun ◽  
Gamze Doğan ◽  
Gülten Kuru ◽  
Melis Küçüksolak ◽  
...  
Keyword(s):  
Endophytic Fungus ◽  
2D Nmr ◽  
Dimethyl Acetal ◽  
Nerium Oleander ◽  
Cytotoxic Activities ◽  
Hek 293 ◽  
Natural Product Library ◽  
Ic50 Values ◽  
Biotransformation Products ◽  
Ft Ir

Microbial biotransformation is an important tool in drug discovery and for metabolism studies. To expand our bioactive natural product library via modification and to identify possible mammalian metabolites, a cytotoxic cardenolide (gitoxigenin) was biotransformed using the endophytic fungus Alternaria eureka 1E1BL1. Initially, oleandrin was isolated from the dried leaves of Nerium oleander L. and subjected to an acid-catalysed hydrolysis to obtain the substrate gitoxigenin (yield; ~25%). After 21 days of incubation, five new cardenolides 1, 3, 4, 6, and 8 and three previously- identified compounds 2, 5 and 7 were isolated using chromatographic methods. Structural elucidations were accomplished through 1D/2D NMR, HR-ESI-MS and FT-IR analysis. A. eureka catalyzed oxygenation, oxidation, epimerization and dimethyl acetal formation reactions on the substrate. Cytotoxicity of the metabolites were evaluated using MTT cell viability method, whereas doxorubicin and oleandrin were used as positive controls. Biotransformation products displayed less cytotoxicity than the substrate. The new metabolite 8 exhibited the highest activity with IC50 values of 8.25, 1.95 and 3.4 µM against A549, PANC-1 and MIA PaCa-2 cells, respectively, without causing toxicity on healthy cell lines (MRC-5 and HEK-293) up to concentration of 10 µM. Our results suggest that A. eureka is an effective biocatalyst for modifying cardenolide-type secondary metabolites.

scholarly journals Monarubins A–C from the Marine Shellfish-Associated Fungus Monascus ruber BB5

Marine Drugs ◽  
2020 ◽  
Vol 18 (2) ◽  
pp. 100
Author(s):  
Yan-Qin Ran ◽  
Wen-Jian Lan ◽  
Yi Qiu ◽  
Qi Guo ◽  
Gong-Kan Feng ◽  
...  
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Carcinoma Cell ◽  
2D Nmr ◽  
Cancer Cell Lines ◽  
Cytotoxic Activities ◽  
Monascus Ruber ◽  
Carcinoma Cell Lines ◽  
Ic50 Values ◽  
New Compounds

Three new compounds, monarubins A–C (1, 6 and 13), together with ten known compounds, including four alkaloids (2–5), two isocoumarins (7 and 8) and four polyketides (9–12), were isolated from marine shellfish-associated fungus Monascus ruber BB5. The structures were determined on the basis of the 1D and 2D NMR, MS, UV and IR data. The absolute configurations of compounds 3, 6 and 13 were determined by ECD calculations. The NMR data of compounds deoxyhydroxyaspergillic acid (3) and 2-hydroxy-6-(1-hydroxy-1-methylpropyl)-3-sec-buthylpyrazine (4) were first reported. All of the isolated compounds were evaluated for their cytotoxic activities against human nasopharyngeal carcinoma cell lines CNE1, CNE2, SUNE1 and HONE1 and hepatocellular carcinoma cell lines QGY7701 and HepG2. Monarubin B (6) displayed potent cytotoxicities against the cancer cell lines HepG2 and QGY7701 with IC50 values of 1.72 and 0.71 μΜ, respectively; lunatinin (7) showed moderate cytotoxic activities against the cancer cell lines HepG2, QGY7701 and SUNE1 with the IC50 values of 9.60, 7.12 and 28.12 μΜ, respectively.

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.

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.

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