scholarly journals New Insights into cytotoxic metabolites produced by Streptomyces griseus isolate KJ623766: Large scale production, structure elucidation and biological activities

2019 ◽  
Author(s):  
Ahmed S. Abu Zaid ◽  
Ahmed E. Aleissawy ◽  
Khaled Aboshanab ◽  
Mahmoud A. Yassien ◽  
Nadia A. Hassouna
Keyword(s):  
Ethyl Acetate ◽  
Large Scale ◽  
Ethyl Acetate Extract ◽  
Biological Activities ◽  
Streptomyces Griseus ◽  
2D Nmr ◽  
Cytotoxic Activities ◽  
Scale Production ◽  
Bioassay Guided Fractionation ◽  
Diphenyl Tetrazolium Bromide

Abstract Natural products particularly microbial metabolites have been the mainstay of cancer chemotherapy and are likely to provide many of the lead structures and derivatives with new biological activities. In this research, the production of some potential cytotoxic metabolites from Streptomyces (S.) griseus isolate KJ623766 was carried out in 14 L laboratory fermenter under specified optimum conditions (28°C temperature, 200 RPM rotation speed, uncontrolled PH, 3 vvm aeration and 2 bar airflow pressure). After 72 hrs of incubation, the cell free culture supernatant (CFCS) was collected and extracted using ethyl acetate (1:1, v/v) at pH 7.0. Using 3-(4,5-dimethylthazol-2-yl)-2,5-diphenyl tetrazolium-bromide (MTT) assay, the cytotoxic activity of the ethyl acetate extract against Caco2 and Hela cancer cell lines was determined with CD50 of 14 µg/ml and 20 µg/ml, respectively. Bioassay guided fractionation of the ethyl acetate extract using different chromatographic techniques had led to the purification of the cytotoxic metabolites coded W1, R1 and R2 with reproducible amounts of 20, 5, and 1.5 mg/l, respectively. The structures of respective metabolites were determined based on the mass, 1D and 2D NMR spectroscopic analysis and were identified as genistein, β-rhodomycinone and γ- rhodomycinone, respectively. Accordingly, S. griseus isolate KJ623766 can be used as a potential industrial strain for the commercial production of the isoflavonoid genistein, as well as for the production of β-and γ- rhodomycinone to be used for the construction of new derivatives with more potent cytotoxic activities of the anthracycline family. To the best of our knowledge, this is the first report about the production of the isoflavonoid genistein by S. griseus KJ623766.

scholarly journals New Insights into cytotoxic metabolites produced by Streptomyces griseus isolate KJ623766: Large scale production, structure elucidation and biological activities

2019 ◽  
Author(s):  
Ahmed S. Abu Zaid ◽  
Ahmed E. Aleissawy ◽  
Khaled Aboshanab ◽  
Mahmoud A. Yassien ◽  
Nadia A. Hassouna
Keyword(s):  
Ethyl Acetate ◽  
Large Scale ◽  
Biological Activities ◽  
Streptomyces Griseus ◽  
Cytotoxic Activities ◽  
Scale Production ◽  
Large Scale Production ◽  
Bioassay Guided Fractionation ◽  
Diphenyl Tetrazolium Bromide ◽  
Cell Free Culture Supernatant

Abstract Natural products particularly microbial metabolites have been the mainstay of cancer chemotherapy and are likely to provide many of the lead structures and derivatives with new biological activities. In this research, the production of some potential cytotoxic metabolites from Streptomyces (S.) griseus isolate KJ623766 was carried out in 1 4 L laboratory fermenter under specified optimum conditions (28°C temperature, 200 RPM rotation speed, uncontrolled PH, 3 vvm aeration and 2 bar airflow pressure). Using 3-(4,5-dimethylthazol-2-yl)-2,5-diphenyl tetrazolium-bromide (MTT) assay, the cytotoxic activity of the ethyl acetate (1:1, v/v) extract of cell free culture supernatant (CFCS) against Caco2 and Hela cancer cell lines was determined with CD 50 of 14 µg/ml and 20 µg/ml, respectively. Bioassay guided fractionation of the ethyl acetate extract using different chromatographic techniques had led to the purification of the cytotoxic metabolites coded W1, R1 and R2 with reproducible amounts of 20, 5, and 1.5 mg/l, respectively. The structures of respective metabolites were determined using various spectroscopic analysis and identified as genistein, β-rhodomycinone and γ- rhodomycinone, respectively. Accordingly, S. griseus isolate KJ623766 can be used as a potential industrial strain for the large scale production of the isoflavonoid genistein, as well as for the production of β-and γ- rhodomycinone to be used for the construction of new derivatives with more potent cytotoxic activities of the anthracycline family. This is the first report about the production of the isoflavonoid genistein by S. griseus KJ623766.

scholarly journals Streptomyces griseus KJ623766: A Natural Producer of Two Anthracycline Cytotoxic Metabolites β- and γ-Rhodomycinone

Molecules ◽  
2021 ◽  
Vol 26 (13) ◽  
pp. 4009
Author(s):  
Ahmed S. Abu Zaid ◽  
Ahmed E. Aleissawy ◽  
Ibrahim S. Yahia ◽  
Mahmoud A. Yassien ◽  
Nadia A. Hassouna ◽  
...  
Keyword(s):  
Ethyl Acetate ◽  
Cell Lines ◽  
Cancer Cell ◽  
Ethyl Acetate Extract ◽  
Biological Activities ◽  
Streptomyces Griseus ◽  
Cancer Cell Lines ◽  
Cytotoxic Activities ◽  
Chemical Structures ◽  
Bioassay Guided Fractionation

Background: This study aimed to produce, purify, structurally elucidate, and explore the biological activities of metabolites produced by Streptomyces (S.) griseus isolate KJ623766, a recovered soil bacterium previously screened in our lab that showed promising cytotoxic activities against various cancer cell lines. Methods: Production of cytotoxic metabolites from S. griseus isolate KJ623766 was carried out in a 14L laboratory fermenter under specified optimum conditions. Using a 3-(4,5-dimethylthazol-2-yl)-2,5-diphenyl tetrazolium-bromide assay, the cytotoxic activity of the ethyl acetate extract against Caco2 and Hela cancer cell lines was determined. Bioassay-guided fractionation of the ethyl acetate extract using different chromatographic techniques was used for cytotoxic metabolite purification. Chemical structures of the purified metabolites were identified using mass, 1D, and 2D NMR spectroscopic analysis. Results: Bioassay-guided fractionation of the ethyl acetate extract led to the purification of two cytotoxic metabolites, R1 and R2, of reproducible amounts of 5 and 1.5 mg/L, respectively. The structures of R1 and R2 metabolites were identified as β- and γ-rhodomycinone with CD50 of 6.3, 9.45, 64.8 and 9.11, 9.35, 67.3 µg/mL against Caco2, Hela and Vero cell lines, respectively. Values were comparable to those of the positive control doxorubicin. Conclusions: This is the first report about the production of β- and γ-rhodomycinone, two important scaffolds for synthesis of anticancer drugs, from S. griseus.

In Vitro Screening for Cytotoxic, Anti-bacterial, Anti-HIV1-RT Activities and Chemical Constituents of Croton fluviatilis, Croton acutifolius, and Croton thorelii

2021 ◽  
Vol 11 ◽  
Author(s):  
Charina Worarat ◽  
Wilart Pompimon ◽  
Phansuang Udomputtimekakul ◽  
Sukee Sukdee ◽  
Punchavee Sombutsiri ◽  
...  
Keyword(s):  
Ethyl Acetate ◽  
Ethyl Acetate Extract ◽  
Biological Activities ◽  
Chemical Constituents ◽  
Bacterial Activity ◽  
Cytotoxic Activities ◽  
Separation And Purification ◽  
Crude Extracts ◽  
Cytotoxicity Activities

Background: Although the chemical constituents and biological activities of a large number of plants in the Croton genus have been studied, there are still recently discovered plants to be investigated. Objective: 1. To investigate the anti-bacterial, anti-HIV1-RT, and cytotoxicity activities of crude extracts from these plants. 2. To investigate the chemical constituents of Croton fluviatilis, Croton acutifolius, and Croton thorelii. Method: The anti-bacterial, anti-HIV1-RT, and cytotoxicity of the three plants were evaluated by standard techniques. Extraction, separation, and purification of extracts from the three plants were undertaken. Results: The ethyl acetate extract of C. fluviatilis showed low anti-bacterial activity against E. aerogenes, E. coli 0157: H7, and P. mirabilis, together with the ethyl acetate extract of C. acutifolius displayed low anti-bacterial activity against E. aerogenes, while all the crude extracts of C. thorelii were inactive. The ethyl acetate extracts of C. thorelii, and C. fluviatilis showed strong inhibited HIV1-RT, whereas the ethyl acetate extract of C. acutifolius, and the hexane extract of C. fluviatilis displayed moderate inhibited HIV1-RT. Cytotoxic properties of three Croton plants were specific to KKU-M213, MDA-MB-231, A-549, and MMNK-1. Especially, the ethyl acetate extract of C. acutifolius exhibited strong cytotoxic activities against MDA-MB-231, A-549, and MMNK-1. Furthermore, the ethyl acetate extract of C. thorelii showed high cytotoxic activities against KKU-M213, and MDA-MB-231. Compounds 1, and 4 were found in C. fluviatilis. Compounds 2 and 4 were also found in C. acutifolius. Moreover, compound 3 was only found in C. thorelii. Conclusion: The present study revealed that the three Croton species are good sources of flavonoid compounds and further investigation of the chemical constituents from these plants may prove to be fruitful to discover more active compounds to be tested as potential medicines.

scholarly journals STUDY ON CHEMICAL CONSTITUENT AND BIOACTIVITIES OF THE FRUITS OF DIPTEROCARPUS RETUSUS BLUME. DIPTEROCARPACEAE OF VIETNAM

2019 ◽  
Vol 57 (3) ◽  
pp. 294
Author(s):  
Ho Dac Hung ◽  
Doan Huy Tien ◽  
Nguyen Thi Ngoan ◽  
Ba Thi Duong ◽  
Do Quoc Viet ◽  
...  
Keyword(s):  
Ethyl Acetate ◽  
Column Chromatography ◽  
Ethyl Acetate Extract ◽  
Biological Activities ◽  
Chemical Constituents ◽  
Chemical Constituent ◽  
Cytotoxic Activities ◽  
Spectroscopic Methods ◽  
Trans Stilbene

The first study on chemical constituents and biological activities of fruits of Dipterocarpus retusus Blume (Dipterocarpaceae.) growing in Vietnam was reported. Column chromatography of the ethyl acetate extract led to the isolation of five compounds: eleutherol (1), 3, 5, 4' - trihydroxy - trans - stilbene (2), polydatin (3) and β-sitosterol (4), β-sitosterol-3-O-β-D-glucopyranoside (5). Their structures were elucidated based on the NMR spectroscopic methods and comparison with literature date. The extracts from fruits of D. retusus Blume by n-hexane, ethyl acetate and butanol, consecutively, were evaluated for antioxidative and cytotoxic activities.

scholarly journals Cyanobacteria—From the Oceans to the Potential Biotechnological and Biomedical Applications

Marine Drugs ◽  
2021 ◽  
Vol 19 (5) ◽  
pp. 241
Author(s):  
Shaden A. M. Khalifa ◽  
Eslam S. Shedid ◽  
Essa M. Saied ◽  
Amir Reza Jassbi ◽  
Fatemeh H. Jamebozorgi ◽  
...  
Keyword(s):  
Bioactive Compounds ◽  
Biomedical Applications ◽  
Large Scale ◽  
Biological Activities ◽  
Scale Production ◽  
Pharmacological Activities ◽  
Large Scale Production ◽  
Marine Products ◽  
Hiv 1 ◽  
Successful Phase

Cyanobacteria are photosynthetic prokaryotic organisms which represent a significant source of novel, bioactive, secondary metabolites, and they are also considered an abundant source of bioactive compounds/drugs, such as dolastatin, cryptophycin 1, curacin toyocamycin, phytoalexin, cyanovirin-N and phycocyanin. Some of these compounds have displayed promising results in successful Phase I, II, III and IV clinical trials. Additionally, the cyanobacterial compounds applied to medical research have demonstrated an exciting future with great potential to be developed into new medicines. Most of these compounds have exhibited strong pharmacological activities, including neurotoxicity, cytotoxicity and antiviral activity against HCMV, HSV-1, HHV-6 and HIV-1, so these metabolites could be promising candidates for COVID-19 treatment. Therefore, the effective large-scale production of natural marine products through synthesis is important for resolving the existing issues associated with chemical isolation, including small yields, and may be necessary to better investigate their biological activities. Herein, we highlight the total synthesized and stereochemical determinations of the cyanobacterial bioactive compounds. Furthermore, this review primarily focuses on the biotechnological applications of cyanobacteria, including applications as cosmetics, food supplements, and the nanobiotechnological applications of cyanobacterial bioactive compounds in potential medicinal applications for various human diseases are discussed.

scholarly journals CONTRIBUTE TO STUDY ON CHEMICAL CONSTITUENTS OF URENA LOBATA (L.) OF VIETNAM

2019 ◽  
Vol 57 (2) ◽  
pp. 162
Author(s):  
Quan Minh Pham ◽  
Hoai Van Thi Tran ◽  
Lam Tien Do ◽  
Phuong Lan Doan ◽  
Inh Thi Cam ◽  
...  
Keyword(s):  
Mental Disorders ◽  
Ethyl Acetate ◽  
Ethyl Acetate Extract ◽  
Chemical Constituents ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Tree Roots ◽  
Chemical Structures ◽  
Phytochemical Investigation ◽  
First Time

Urena lobata L. is used in Vietnamese traditional medicine for the treatment of several diseases. Tree roots are used to treat rheumatism, dysentery, poor digestion, flu, tonsils, malaria, asthma, goiter. Flowers are used to treat chickenpox, fever, and mental disorders. Branches, leaves or whole trees used to treat injuries bruises, rheumatism, mastitis, bites. Phytochemical investigation of the n-hexan and ethyl acetate extract of Urena lobata L. led to the isolation of β-sitosterol (1), β-sitosterol-3-O-β-D-glucopyranoside (2), a-acetylamino-phenylpropyl a-benzoylamino-phenylpropanoate (3), quercetin (4), and trans-tiliroside (5). Their chemical structures were determined by spectroscopic methods including MS, 1D, 2D NMR and comparing with those reported in previous papers. Two compounds 3, 5 were isolated for the first time from Urena lobata plant.

scholarly journals A NEW CYTOTOXIC DOLABELLANE FROM THE INDONESIAN SOFT CORAL Anthelia sp.

2013 ◽  
Vol 13 (3) ◽  
pp. 216-220 ◽  
Author(s):  
Anggia Murni ◽  
Novriyandi Hanif ◽  
Junichi Tanaka
Keyword(s):  
Mass Spectrometry ◽  
Drug Development ◽  
Ethyl Acetate ◽  
Spectroscopic Data ◽  
Soft Coral ◽  
Ethyl Acetate Extract ◽  
2D Nmr ◽  
Cancer Drug ◽  
Nmr Data ◽  
Anti Cancer

One new dolabellane (1) and two known diterpenoids stolonidiol (2) and clavinflol B (3) have been isolated from the ethyl acetate extract of the Indonesian soft coral Anthelia sp. A new compound 1 exhibited a moderate cytotoxicity against NBT-T2 cells at 10 µg/mL, while known compounds 2 and 3 showed cytotoxicity at 1 and 0.5 µg/mL, respectively. Structure of the new compound 1 was elucidated by interpretation of NMR spectroscopic data (1D and 2D NMR data) and mass spectrometry (ESIMS data) as well as comparison with those of related ones. This finding should be useful for anti cancer drug development of the promising dolabellane-types compound.

scholarly journals Studies on Chemical Constituents and Biological Activities of an Endophytic Fungi from Magnifera indica L.

2015 ◽  
Vol 13 (1) ◽  
pp. 63-67
Author(s):  
Mozammel Haque ◽  
Mohammad Shoeb ◽  
Nilufar Nahar
Keyword(s):  
Ethyl Acetate ◽  
Ethyl Acetate Extract ◽  
Biological Activities ◽  
Chemical Constituents ◽  
Radical Scavenging ◽  
Acid Methyl Ester ◽  
Diffusion Method ◽  
Published Data ◽  
Nmr Studies ◽  
Brine Shrimp Lethality Assay

Two compounds, ergosterol (1) and 4-hydroxy-hexadec-6-enoic acid methyl ester (2) were isolated from the ethyl acetate extract of the endophytic fungal strain labeled as MI-3, isolated from the leave of Magnifera indica L. The structures of the isolated compounds were elucidated by 1H NMR studies and comparing with published data. The crude ethyl acetate extract, three column fractions and ergosterol were tested for antimicrobial activity against five Gram-positive and eight Gram-negative bacteria and three fungi by disc diffusion method. The general toxicity and antioxidant activity of the parent extract, column fractions and ergosterol were also evaluated by using brine shrimp lethality assay and free radical scavenging assay, respectively. Low activities were observed in all cases. DOI: http://dx.doi.org/10.3329/dujps.v13i1.21862 Dhaka Univ. J. Pharm. Sci. 13(1): 63-67, 2014 (June)

scholarly journals Bioactivity-guided isolation of alkamides from a cytotoxic fraction of the ethyl acetate extract of Anacyclus pyrethrum (L.) DC. roots.

2018 ◽  
Vol 31 (4) ◽  
pp. 180-185
Author(s):  
Souad Hamimed ◽  
Nadji Boulebda ◽  
Hocine Laouer ◽  
Abdelmalik Belkhiri
Keyword(s):  
Ethyl Acetate ◽  
Cytotoxic Activity ◽  
Cell Lines ◽  
Cancer Cell ◽  
Ethyl Acetate Extract ◽  
Human Cancer ◽  
Colorectal Cancer Cell Line ◽  
Cytotoxic Activities ◽  
Root Extract ◽  
Alcohol Extract

Abstract Introduction. The alcohol extract of Pellitory (Anacyclus pyrethrum) roots has been previously shown to exert anticancer activities on the Human Colorectal Cancer Cell Line (HCT) by targeting apoptosis, metastasis and cell cycle arrest. However, the nature of the cytotoxic molecules associated with this activity remains unexplored. Aims. This study aims to reinvestigate Pellitory root extract as regard to its cytotoxic activity and to proceed to a bioguided fractionation to explore its active fraction and to give new insight in their phytochemical constituents. Methods. Powdered roots were subjected to repeated extraction with Petroleum ether (Pe), Chloroform (Ch), Ethyl acetate (Ea) and Methanol (Me). Pellitory extracts were then screened for cytotoxic activity using the Brine Shrimp Lethality (BSL) bioassay. Results. Ea extract exhibited a marked cytotoxic activity, with LC50 of 249.26 μg/mL in the BSL bioassay. The remaining extracts (Pe,Ch,Me) treated groups exhibited no or low mortality in the range of tested concentrations (1-1000 µg/mL). BSL assay-guided chromatographic fractionation of Ea active Extract revealed a highly cytotoxic fraction (F11) with LC50 of 42.5 µg/mL. Multistep purifications of the active F11 fraction afforded four alkamides, namely N-isobutyldeca-2,4-dienamide or Pellitorine (I), N-propyldodeca- -2,8-dienamide (II), N-isobutyltetradeca-2,4-dienamide (III) and N-propylnona-2,5- -dienamide (IV). Conclusions. This study suggests that cytotoxic activity is localized mainly in the ethyl acetate extract (Ea) of pellitory roots. BSL assay fractionation of this active extract leads to the isolation of four alkamides, including pellitorine (I). While this isobutyl alkamide has previously shown strong cytotoxic activities against human cancer cell lines, the other compounds (II to IV) were not previously reported as cytotoxic. Subsequently, the isolated alkamides will be considered in future study as candidates for in depth in-vitro evaluation of their cytotoxicity against cancer and normal cell lines. Finally, through this study, BSL assay demonstrate again its usefulness as bench-top assay in exploring plant extracts for cytotoxic compounds.

scholarly journals Four Flavan-3-ol Compounds From The Stembark of Chisocheton balansae C.DC. (MELIACEAE)

Molekul ◽  
2021 ◽  
Vol 16 (1) ◽  
pp. 9
Author(s):  
Unang Supratman ◽  
Mohamad Fajar ◽  
Supriatno Salam ◽  
Rani Maharani ◽  
Desi Harneti ◽  
...  
Keyword(s):  
Ethyl Acetate ◽  
13C Nmr ◽  
Chemical Structure ◽  
Ethyl Acetate Extract ◽  
2D Nmr ◽  
Stem Bark ◽  
Spectroscopic Methods ◽  
Endemic Plants ◽  
North Sulawesi ◽  
First Time

Chisocheton balansae C.DC., is one of the Meliaceae family plants which is the endemic plants from Soputan Mountain, North Sulawesi, Indonesia. This study was aimed to determine the chemical structure of flavan-3-ol compounds from ethyl acetate extract of C. balansae C.DC stembark. Dried powder of C. balansae C.DC stem bark was extracted consecutively with n-hexane, ethyl acetate, and methanol solvents. Four flavan-3-ol compounds, named catechin (1), epicatechin (2), epigallocatechin-3-O-gallate (3), and epicatechin-3-O-gallate (4) were successfully isolated from ethyl acetate extract. The chemical structure of these isolates was determined by spectroscopic methods (1H-NMR, 13C-NMR, DEPT, and 2D-NMR) and comparison with previous reported spectral data. These compounds are first time reported from this plant.

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