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 Comparative Study of Naphthoquinone Contents of Selected Greek Endemic Boraginaceae Plants - Antimicrobial Activities

2017 ◽  
Vol 12 (2) ◽  
pp. 1934578X1701200
Author(s):  
Teisa Tufa ◽  
Harilaos Damianakos ◽  
Konstantia Graikou ◽  
Ioanna Chinou
Keyword(s):  
Antimicrobial Activity ◽  
Nmr Spectroscopy ◽  
Comparative Study ◽  
Pathogenic Fungi ◽  
2D Nmr ◽  
Antimicrobial Activities ◽  
2D Nmr Spectroscopy ◽  
Chromatographic Separations ◽  
Esi Ms ◽  
Related Compounds

The cyclohexane (Ch) extracts of the roots of five Greek endemic Boraginaceae plants, Onosma kaheirei Teppner, O. graeca Boiss., O. erecta Sibth. & Sm., Alkanna sfikasiana Kit Tan, Vold and Strid and Cynoglossum columnae Ten, were investigated for the presence of alkannin/shikonin-related compounds. All species, s except C. columnae and O. erecta, were found to contain this type of compounds. Seven compounds were obtained after several chromatographic separations from the Ch extracts of the investigated plants: deoxyalkannin (1), 2″-( S)- α-methylbutyrylalkannin (2), isobutyrylalkannin (3), propionylalkannin (4), acetylalkannin (5), β-hydroxyisovalerylalkannin (6), and β,β-dimethylacrylalkannin (7). All structures were identified by 1D 1H-/13C- and 2D NMR spectroscopy, assisted also by ESI-MS. The extracts and the isolated compounds exhibiting an interesting antimicrobial profile when evaluated for their antimicrobial activity against six Gram-positive and -negative bacteria and three human pathogenic fungi.

scholarly journals New Alkaloids and Polyketides from the Marine Sponge-Derived Fungus Penicillium sp. SCSIO41015

Marine Drugs ◽  
2019 ◽  
Vol 17 (7) ◽  
pp. 398 ◽  
Author(s):  
Xiaoyan Pang ◽  
Guodi Cai ◽  
Xiuping Lin ◽  
Limbadri Salendra ◽  
Xuefeng Zhou ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
2D Nmr ◽  
Specific Rotation ◽  
Human Gastric Cancer ◽  
X Ray Diffraction ◽  
Gastric Cancer Cells ◽  
Penicillium Sp ◽  
Ic50 Value ◽  
Rice Medium ◽  
Weak Antibacterial Activity

The sponge-derived fungus Penicillium sp. SCSIO41015 cultured on solid rice medium yielded twenty-one compounds (1–21), including two new alkaloids (1 and 2) and one new pyrone derivative (3). Their structures were elucidated by analysis of 1D/2D NMR data and HR–ESI–MS. Their absolute configurations were established by single-crystal X-ray diffraction analysis and comparison of the experimental with reported specific rotation values. Compound 16 exhibited selective cytotoxic activity against the human gastric cancer cells MGC803, with IC50 value of 5.19 μM. Compounds 9 and 18 showed weak antibacterial activity against Staphylococcus aureus and Acinetobacter baumannii, respectively, both with MIC values of 57 μg/mL. Furthermore, compound 16 displayed potent antibacterial activity against S. aureus with an MIC value of 3.75 μg/mL.

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.

scholarly journals Shellmycin A–D, Novel Bioactive Tetrahydroanthra-γ-Pyrone Antibiotics from Marine Streptomyces sp. Shell-016

Marine Drugs ◽  
2020 ◽  
Vol 18 (1) ◽  
pp. 58 ◽  
Author(s):  
Yong Han ◽  
Yan Wang ◽  
Yuehan Yang ◽  
Haotong Chen
Keyword(s):  
Absolute Configuration ◽  
Nature Reserve ◽  
2D Nmr ◽  
Biosynthetic Pathways ◽  
X Ray Diffraction ◽  
Streptomyces Sp ◽  
X Ray ◽  
Structure Activity ◽  
Ic50 Value ◽  
Marine Streptomyces

Four novel bioactive tetrahydroanthra-γ-pyrone compounds, shellmycin A–D (1–4), were isolated from the marine Streptomyces sp. shell-016 derived from a shell sediment sample collected from Binzhou Shell Dike Island and Wetland National Nature Reserve, China. The structures of these four compounds were established by interpretation of 1D and 2D NMR and HR-MS data, in which the absolute configuration of 1 was confirmed by single crystal X-ray diffraction, and compound 3 and 4 are a pair of stereoisomers. Compound 1–4 exhibited cytotoxic activity against five cancer cell lines with the IC50 value from 0.69 μM to 26.3 μM. Based on their structure–activity relationship, the putative biosynthetic pathways of these four compounds were also discussed.

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 Cytotoxic Polyketide Metabolites from a Marine Mesophotic Zone Chalinidae Sponge-Associated Fungus Pleosporales sp. NBUF144

Marine Drugs ◽  
2021 ◽  
Vol 19 (4) ◽  
pp. 186
Author(s):  
Jing Zhou ◽  
Hairong Zhang ◽  
Jing Ye ◽  
Xingxin Wu ◽  
Weiyi Wang ◽  
...  
Keyword(s):  
Mass Spectra ◽  
Spectroscopic Analysis ◽  
2D Nmr ◽  
Leukemia Cells ◽  
Ionization Mass ◽  
X Ray Diffraction ◽  
X Ray ◽  
Lymphatic Leukemia ◽  
Ic50 Value ◽  
Lymphatic Leukemia Cells

Two new polyketide natural products, globosuxanthone F (1), and 2′-hydroxy bisdechlorogeodin (2), were isolated from the fungus Pleosporales sp. NBUF144, which was derived from a 62 m deep Chalinidae family sponge together with four known metabolites, 3,4-dihydroglobosuxanthone A (3), 8-hydroxy-3-methylxanthone-1-carboxylate (4), crosphaeropsone C (5), and 4-megastigmen-3,9-dione (6). The structures of these compounds were elucidated on the basis of extensive spectroscopic analysis, including 1D and 2D NMR and high-resolution electrospray ionization mass spectra (HRESIMS) data. The absolute configuration of 1 was further established by single-crystal X-ray diffraction studies. Compounds 1-5 were evaluated for cytotoxicity towards CCRF-CEM human acute lymphatic leukemia cells, and it was found that 1 had an IC50 value of 0.46 µM.

scholarly journals Cyclic Peptides from the Soft Coral-Derived Fungus Aspergillus sclerotiorum SCSIO 41031

Marine Drugs ◽  
2021 ◽  
Vol 19 (12) ◽  
pp. 701
Author(s):  
Jieyi Long ◽  
Yaqi Chen ◽  
Weihao Chen ◽  
Junfeng Wang ◽  
Xuefeng Zhou ◽  
...  
Keyword(s):  
Cyclic Peptides ◽  
Soft Coral ◽  
2D Nmr ◽  
X Ray Diffraction ◽  
X Ray ◽  
Cyclic Hexapeptide ◽  
Ic50 Value ◽  
Ic50 Values ◽  
Cyclic Hexapeptides ◽  
Aspergillus Sclerotiorum

Three novel cyclic hexapeptides, sclerotides C–E (1–3), and a new lipodepsipeptide, scopularide I (4), together with a known cyclic hexapeptide sclerotide A (5), were isolated from fermented rice cultures of a soft coral-derived fungus: Aspergillus sclerotiorum SCSIO 41031. The structures of the new peptides were determined by 1D and 2D NMR spectroscopic analysis, Marfey’s method, ESIMS/MS analysis, and single crystal X-ray diffraction analysis. Scopularide I (4) exhibited acetylcholinesterase inhibitory activity with an IC50 value of 15.6 μM, and weak cytotoxicity against the human nasopharyngeal carcinoma cell line HONE-EBV with IC50 values of 10.1 μM.

scholarly journals Laurencia Filiformis: Phytochemical Profiling by Conventional and HPLC-NMR Approaches

2009 ◽  
Vol 4 (2) ◽  
pp. 1934578X0900400 ◽  
Author(s):  
Daniel A. Dias ◽  
Jonathan M. White ◽  
Sylvia Urban
Keyword(s):  
Marine Organism ◽  
Chemical Conversion ◽  
2D Nmr ◽  
Antimicrobial Activities ◽  
X Ray Diffraction ◽  
Nmr Studies ◽  
X Ray ◽  
Chemical Profiling ◽  
New Compounds ◽  
Stop Flow

Chemical investigation of the southern Australian marine alga Laurencia filiformis forma heteroclada resulted in the isolation of two new compounds, cycloisoallolaurinterol (16) and isoallolaurinterol (23), along with the previously reported sesquiterpenes filiformin (1), filiforminol (2), allolaurinterol (3) and bromolaurenisol (10). All structures were secured by detailed spectroscopic analysis since no previous 2D NMR studies had been described for compounds 1, 2 and 10. As a result of this study, the first single X-ray diffraction study for 1 was secured. The investigation of the chemical conversion of allolaurinterol (3) to filiformin (1) was monitored by on-flow HPLC-NMR, which also resulted in the identification of 23. We propose that both compounds 16 and 23 are formed as artefacts from allolaurinterol (3). HPLC-NMR was used to profile the crude extract of a marine organism, as well as for monitoring online compound chemical conversions. Both on-flow and stop-flow HPLC-NMR were successfully applied in the chemical profiling and compound chemical conversion studies of L. filiformis forma heteroclada. Compounds 2 and 3 displayed antimicrobial activities.

Synthesis, Docking Study, Cytotoxicity, Antioxidant, and Anti-microbial Activities of Novel 2,4-Disubstituted Thiazoles Based on Phenothiazine

2020 ◽  
Vol 17 (2) ◽  
pp. 151-159
Author(s):  
Tran Nguyen Minh An ◽  
Pham Thai Phuong ◽  
Nguyen Minh Quang ◽  
Nguyen Van Son ◽  
Nguyen Van Cuong ◽  
...  
Keyword(s):  
Cell Line ◽  
Cancer Cell ◽  
Cancer Cell Line ◽  
Antimicrobial Activities ◽  
Significant Activity ◽  
Thiazole Derivatives ◽  
Ligand Interaction ◽  
Ic50 Value ◽  
Mcf 7

: A series of novel 1,3-thiazole derivatives (5a-i) with a modified phenothiazine moiety were synthesized and tested against cancer cell line MCF-7 for their cytotoxicity. Most of them (5a-i) were less cytotoxic or had no activity against MCF-7 cancer cell line. Material and Methods: The IC50 value of compound (4) was 33.84 μM. The compounds (5a-i) were also evaluated for antimicrobial activities, but no significant activity was observed. The antioxidant activity was conducted for target compounds (5a-i). The IC50 value of compound (5b) was 0.151mM. Results: The total amount of energy, ACE (atomic contact energy), energy of receptor (PDB: 5G5J), and ligand interaction of structure (4) were found to be 22.448 Kcal.mol-1 , -247.68, and -91.91 Kcal.mol-1, respectively. The structure (4) is well binded with the receptor because the values of binding energy, steric energy, and the number of hydrogen bondings are -91.91, 22.448 kcal.mol-1, and 2, respectively. It shows that structure (4) has good cytotoxicity with MCF-7 in vitro. Conclusion: The increasing of docking ability of structures (5a-i) with the receptor is presented in increasing order as (5f)>(5e)>(5g)>(5a)>(5b)>(5d)>(5c)>(5i)>(5h). The structure bearing substitution as thiosemicarbazone (4), nitrogen heterocyclic (5f), halogen (5e), and azide (5g) showed good cytotoxicity activity in vitro.

Design and synthesis of new antifungals based on N- un-substituted azoles as 14α demethylase inhibitor

2020 ◽  
Vol 16 ◽  
Author(s):  
Asghar Davood ◽  
Aneseh Rahimi ◽  
Maryam Iman ◽  
Parisa Azerang ◽  
Soroush Sardari ◽  
...  
Keyword(s):  
Antimicrobial Agents ◽  
Antifungal Agents ◽  
Molecular Design ◽  
Pathogenic Fungi ◽  
Antimicrobial Activities ◽  
Docking Studies ◽  
Receptor Interaction ◽  
Main Role ◽  
Design And Synthesis ◽  
Antifungal Antibiotics

Objective(s): Azole antifungal agents, which are widely used as antifungal antibiotics, inhibit cytochrome P450 sterol 14α-demethylase (CYP51). Nearly all azole antifungal agents are N-substituted azoles. In addition, an azolylphenalkyl pharmacophore is uniquely shared by all azole antifungals. Due to importance of nitrogen atom of azoles (N-3 of imidazole and N-4 of triazole) in coordination with heme in the binding site of the enzyme, here a group of N- un-substituted azoles in which both of nitrogen is un-substituted was reported. Materials and Methods: Designed compounds were synthesized by reaction of imidazole-4-carboxaldehyde with appropriate arylamines and subsequently reduced to desired amine derivatives. Antifungal activity against Candida albicans and Saccharomyces cervisiae were done using a broth micro-dilution assay. Docking studies were done using AutoDock. Results: Antimicrobial evaluation revealed that some of these compounds exhibited moderate antimicrobial activities against tested pathogenic fungi, wherein compound 3, 7 and 8 were potent. Docking studies propose that all of the prepared azoles interacted with 14α-DM, wherein azole-heme coordination play main role in drug-receptor interaction. Conclusion: Our results offer some useful references in order to molecular design performance or modification of this series of compounds as a lead compound to discover new and potent antimicrobial agents.

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