Search for anti-dengue secondary metabolites from two Diospyros endophytes, Aspergillus sp. and Phomopsis sp

Objective: Aspergillus fungus is a rich source of natural products with broad biological activities. This study was conducted to identify secondary metabolites from the rice culture of Aspergillus species isolated from Melaleuca subulata leaves and evaluated their anticancer activity. Methods: Ethyl acetate extract was fractionated on silica gel and Sephadex columns. Structures of the compounds were established using physical and chemical methods. Cytotoxic activities of the extract and pure compounds against two human cancer cell lines (Mcf-7and Hep G2) were evaluated using microculture tetrazolium assay as well as the mode of the cytotoxicity was evaluated. Molecular docking studies have been performed using the Hsp 90 enzyme as an anticancer target. Results: Methyl linoleate (1), arugosin C (2), ergosterol (3), sterigmatocystin (4), diorcinol (5), alternariol-5-O-methyl ether (6), averufin (7), averufanin (8), and alternariol (9) were identified from ethyl acetate extract. All tested compounds exhibit week activity against MCF-7 and Hep G2 cell lines but a mixture of compounds 7 and 8 is considered to be more active towards both MCF-7 and Hep G 2 in comparison to other compounds. Compound 4 exhibits moderate activity against Hep G2 only as well as the ethyl acetate extract exerts moderate activity against MCF-7 cell line Moreover, compound 4 and a mixture of 7 and 8 caused a decrease in the number of Hep G2 cancer cells due to apoptotic and necrotic processes. Most active anticancer candidates 7 and 8 showed binding to the active site similar to geldanamycin reference ligand. Conclusion: Secondary metabolites identified from Aspergillus sp. and their anticancer activity were evaluated. Molecular docking suggested active candidates as Hsp 90 inhibitors.

Download Full-text

Cytotoxicity, Antimicrobial, and In Silico Studies of Secondary Metabolites From Aspergillus sp. Isolated From Tecoma stans (L.) Juss. Ex Kunth Leaves

Frontiers in Chemistry ◽

10.3389/fchem.2021.760083 ◽

2021 ◽

Vol 9 ◽

Author(s):

Heba E. Elsayed ◽

Reem A. Kamel ◽

Reham R. Ibrahim ◽

Ahmed S. Abdel-Razek ◽

Mohamed A. Shaaban ◽

...

Keyword(s):

Secondary Metabolites ◽

In Silico ◽

Therapeutic Potential ◽

Antibacterial Activities ◽

Antimicrobial Activities ◽

Kinase Domain ◽

Binding Score ◽

In Silico Studies ◽

Binding Cleft ◽

Aspergillus Sp

Endophytes are prolific producers of privileged secondary metabolites with diverse therapeutic potential, although their anticancer and antimicrobial potential still have a room for further investigation. Herein, seven known secondary metabolites namely, arugosin C (1), ergosterol (2), iso-emericellin (3), sterigmatocystin (4), dihydrosterigmatocystin (5), versicolorin B (6), and diorcinol (7) were isolated from the rice culture of Aspergillus sp. retrieved from Tecoma stans (L.) Juss. ex Kunth leaves. Their anticancer and antimicrobial activities were evaluated in MTT and agar well diffusion assays, respectively. The cytotoxicity results showed that metabolite 3 displayed the best viability inhibition on the MCF-7 breast cancer cells with IC50 = 225.21 µM, while 5 on the HepG2 hepatocellular carcinoma cells with IC50 = 161.81 µM. 5 demonstrated a 60% apoptotic mode of cell death which is virtually correlated to its high docking affinity to Hsp90 ATP binding cleft (binding score −8.4 Kcal/mol). On the other side, metabolites 4 and 5 displayed promising antimicrobial activity especially on Pseudomonas aeruginosa with MIC = 125 μg/ml. The observed effect may be likely related to their excellent in silico inhibition of the bacterial DNA-gyrase kinase domain (binding score −10.28 Kcal/mol). To the best of our knowledge, this study is the first to report the promising cytotoxic and antibacterial activities of metabolites 3, 4, and 5 which needs further investigation and renovation to therapeutic leads.

Download Full-text

JBIR-137 and JBIR-138, new secondary metabolites from Aspergillus sp. fA75

The Journal of Antibiotics ◽

10.1038/ja.2012.64 ◽

2012 ◽

Vol 65 (10) ◽

pp. 535-538 ◽

Cited By ~ 9

Author(s):

Teppei Kawahara ◽

Aya Nagai ◽

Motoki Takagi ◽

Kazuo Shin-ya

Keyword(s):

Secondary Metabolites ◽

Aspergillus Sp

Download Full-text

Identification and Biological Evaluation of Secondary Metabolites from Marine Derived Fungi-Aspergillus sp. SCSIOW3, Cultivated in the Presence of Epigenetic Modifying Agents

Molecules ◽

10.3390/molecules22081302 ◽

2017 ◽

Vol 22 (8) ◽

pp. 1302 ◽

Cited By ~ 18

Author(s):

Xiaofan Li ◽

Zhenyao Xia ◽

Jianqiang Tang ◽

Jiahui Wu ◽

Jing Tong ◽

...

Keyword(s):

Secondary Metabolites ◽

Biological Evaluation ◽

Aspergillus Sp

Download Full-text

Antimicrobial Secondary Metabolites from the Marine-Derived Fungus Aspergillus sp. M28

Chemistry of Natural Compounds ◽

10.1007/s10600-020-03259-w ◽

2020 ◽

Vol 56 (6) ◽

pp. 1173-1175

Author(s):

Le Thi Hong Minh ◽

Nguyen Thi Hue ◽

Nguyen Thuy Linh ◽

Truong Bich Ngan ◽

Vu Thi Quyen ◽

...

Keyword(s):

Secondary Metabolites ◽

Aspergillus Sp

Download Full-text

Antimicrobial and Cytotoxic Activities of Secondary Metabolites from the Soft Coral Derived Fungus Aspergillus sp.

Chemistry of Natural Compounds ◽

10.1007/s10600-019-02732-5 ◽

2019 ◽

Vol 55 (3) ◽

pp. 531-533

Author(s):

Gulab Said ◽

Xue-Mei Hou ◽

Xin Liu ◽

Rong Chao ◽

Yao-Yao Jiang ◽

...

Keyword(s):

Secondary Metabolites ◽

Soft Coral ◽

Cytotoxic Activities ◽

Aspergillus Sp

Download Full-text

Antibacterial Secondary Metabolites from Marine-Derived Fungus Aspergillus sp. IMCASMF180035

Antibiotics ◽

10.3390/antibiotics10040377 ◽

2021 ◽

Vol 10 (4) ◽

pp. 377

Author(s):

Fuhang Song ◽

Rui Lin ◽

Na Yang ◽

Jia Jia ◽

Shangzhu Wei ◽

...

Keyword(s):

Secondary Metabolites ◽

Spectroscopic Data ◽

Inhibitory Concentration ◽

Antibacterial Activities ◽

Ring System ◽

Ionization Mass ◽

Inhibitory Effects ◽

Nmr Techniques ◽

Aspergillus Sp ◽

H Pylori

Four new secondary metabolites, including one spiro[anthracenone-xanthene] derivative aspergiloxathene A (1), one penicillide analogue, Δ2′-1′-dehydropenicillide (2), and two new phthalide derivatives, 5-methyl-3-methoxyepicoccone (3) and 7-carboxy-4-hydroxy-6-methoxy-5-methylphthalide (4), together with four known compounds, yicathin C (5), dehydropenicillide (6), 3-methoxyepicoccone (7), 4-hydroxy-6-methoxy-5-methylphthalide (8), were identified from the marine-derived fungus Aspergillus sp. IMCASMF180035. Their structures were determined by spectroscopic data, including high-resolution electrospray ionization mass spectrometry (HRESIMS), 1D and 2D nuclear magnetic resonance (NMR) techniques. Compound 1 was identified as the first jointed molecule by xanthene and anthracenone moieties possessing an unprecedented carbon skeleton with spiro-ring system. All compounds were evaluated activities against Staphylococcus aureus, methicillin resistant S. aureus (MRSA), Escherichia coli, Escherichia faecium, Pseudomonas aeruginosa, and Helicobacter pylori. Compound 1 showed significant inhibitory effects against S. aureus and MRSA, with minimum inhibitory concentration (MIC) values of 5.60 and 22.40 µM. Compounds 2 and 6 exhibited potent antibacterial activities against H. pylori, with MIC values of 21.73 and 21.61 µM, respectively.

Download Full-text

Effectiveness of Secondary Metabolites from Entomopathogenic Fungi for Control Nilaparvata lugens Stål. in the Laboratory Scale

Jurnal Perlindungan Tanaman Indonesia ◽

10.22146/jpti.62116 ◽

2021 ◽

Vol 25 (1) ◽

pp. 86

Author(s):

Endang Warih Minarni ◽

Loekas Soesanto ◽

Agus Suyanto ◽

Rostaman Rostaman

Keyword(s):

Secondary Metabolites ◽

Crop Yields ◽

Block Design ◽

Brown Planthopper ◽

Nilaparvata Lugens ◽

Crop Failure ◽

Randomized Block Design ◽

Fusarium Sp ◽

Aspergillus Sp ◽

Nilaparvata Lugens Stål

Nilaparvata lugens Stål. is an essential pest in rice plants. This pest attack can reduce crop yields and even crop failure. This research was conducted to obtain secondary metabolites that are effective in controlling brown planthopper (BPH). A randomized block design was used to test the effectiveness of secondary metabolites against BPH. The treatments tested were secondary metabolites produced by eight isolates of fungi consist of three concentrations: 5, 10, and 15%. Water and imidacloprid insecticide were used as control. The eight isolates were: J11 (Aspergillus sp.), J22 (Lecanicillium saksenae), J34 (Myrothecium sp.), J35 (Beauveria sp.), J41 (Fusarium sp.), J56 (Fusarium sp), J60 (Simplicillium sp.), and J65 (Curvularia sp.). Each treatment was repeated three times. The variables observed were mortality and time of death of BPH. Data were analyzed using the F test and followed by a DMRT if significant differences existed. The results showed that the secondary metabolites of the Lecanicillium saksenae, Myrothecium sp., and Simplicillium sp. fungi effectively controlled BPH pests by 80‒100% within 3.22‒5.47 days. The fungus L. saksenae, Myrothecium sp., and Simplicillium sp. contain insecticidal compounds, clogging the insect spiraculum, antifeedant, repellant, and antimicrobial.

Download Full-text