Ngo Thi Trang, Tong Thi Ngoc Anh, Lai Ngoc Khanh, Tran Thi Hang, Nguyen Thi Bich Loan, Tran Thi Thuy Anh, Nguyen Thuy Lien, Nguyen Thi Thu Lien, Pham Thi Luong Hang

Main Article Content

Abstract

As part of the ongoing efforts to exploit the pharmaceutical potential of domestic cyanobacteria, six strains belonging to the Nostocales order have been isolated from several sampling sites in Hanoi as prerequisite material. The cytotoxic activity evaluation based on the MTT test resulted in four extracts of two strains (HK7 and NK1111) exhibiting the inhibitory activity against HeLa cells, with IC50 values ranging from 84.6 µg/mL to 257.3 µg/mL. The methanol extract of strain HK7 was further fractionated by LH-20 column chromatography to afford the K3 fraction, which inhibited 70% growth of HeLa cells at the concentration of 20.0 µg/mL. In addition, the high-resolution mass spectrometric analysis detected the presence of two natural compounds in the K3 fraction. Compound 1 showed the accurate mass of 352.2633 Da, suggesting a molecular formula of C21H36O4 similar to two cytotoxic compounds 7Z-plakortide H or 10-gingerdiol. Compound 2 had the accurate mass of 278.1545 Da, suggesting a molecular formula of C16H22O4 similar to four cytotoxic compounds pestaloficiol G, penicitrinol E-D, or isoversiol C.

Keywords: Cyanobacteria, Nostocales, cytotoxic activity.

References

[1] K. V. Bajpai, S. Shukla, S. M. Kang, S. K. Hwang, X. Song, Y.S. Huh, Y.K. Han, Developments of Cyanobacteria for Nano-Marine Drugs: Relevance of Nanoformulations in Cancer Therapies, Mar, Drugs, Vol.16, 2018, pp. 179-201.
[2] G. E. Chlipala, S. Mo, J. Orjala, Chemodiversity in Freshwater and Terrestrial Cyanobacteria - a Source for Drug Discovery, Curr, Drug Targets, Vol.12, 2011, pp. 1654-73.
[3] J. Demay, C. Bernard, A. Reinhardt, B. Marie, Natural Products from Cyanobacteria: Focus on Beneficial Activities, Mar. Drugs, Vol. 17, 2019, pp. 320-69.
[4] R. B. Dixit, M. R. Suseela, Cyanobacteria: Potential Candidates for Drug Discovery, Antonie Van Leeuwenhoek, Vol. 103, 2013, pp. 947-61.
[5] R. K. Singh, S. P. Tiwari, A. K. Rai, T. M. Mohapatra, Cyanobacteria: an Emerging Source for Drug Discovery, J. Antibiot (Tokyo), Vol. 64, 2011, pp. 401-12.
[6] B. E. de Goeij, J. M. Lambert, New Developments for Antibody-Drug Conjugate-based Therapeutic Approaches, Curr, Opin, Immunol, Vol. 40, 2016, pp. 14-23.
[7] V. A. Verma, T. H. Pillow, L. DePalatis, G. Li, G. L. Phillips, A. G. Polson, H. E. Raab, S. Spencer, B. Zheng, The Cryptophycins as Potent Payloads for Antibody Drug Conjugate, Bioorg, Med, Chem, Lett, Vol. 25, 2015, pp. 864-68.
[8] A. Younes, N. L. Bartlett, J. P. Leonard, D. A. Kennedy, C. M. Lynch, E. L. Sievers, A. F. Torres, Brentuximab Vedotin (SGN-35) for relapsed CD30-positive lymphomas, The New England Journal of Medicine, Vol. 36, 2010, pp. 1812-21.
[9] D. T. Duong, Classification of Vietnamese Cyanobacteria, Agricultural Institute Public Publishing House, 1996, pp. 10 - 120 (in Vietnamese).
[10] H. T. L. Pham, L. T. T. Nguyen, A. T. Duong, D. T. T. Bui, Q. T. Doan, H. T. T. Nguyen, S. Mundt, Diversity and Bioactivities of Nostocacean Cyanobacteria Isolated from Paddy Soil in Vietnam, Syst, Appl, Microbiol, Vol. 40, 2017, pp. 470-81.
[11] R. Rippka, R. Duruelles, J. B. Waterbury, M. Herbman, R. Y. Stanier, Generic Assignments, Strain Histories and Properties of Pure Cultures of Cyanobacteria, J. Gen, Microbiol, Vol. 111, 1979, pp. 1-61.
[12] R. A. Andersen, M. Kawachi, Traditional Microalgae Isolation Techniques, in Algal Culturing Techniques, Elsevier, Amsterdam, 2005, pp. 83-100.
[13] J. Komárek, J. Kaštovský, J. Mareš, J. R. Johansen, Taxonomic Classification of Cyanoprokaryotes (Cyanobacterial Genera) 2014, Using a Polyphasic Approach, Preslia, Vol. 86, 2014, pp. 295-335.
[14] L. T. B. Nguyen, T. K. Kieu, T. L. Nguyen, T. K.T. Nguyen, H. Q. Nguyen, T. H. Pham, M. Muller, A. Nachtergael, P. Duez, T. D. Nguyen, Toxicity and Anti-Proliferative Properties of Anisomeles Indica Ethanol Extract on Cervical Cancer HeLa Cells and Zebrafish Embryos, Life, Vol. 11, 2021, pp. 257-72.
[15] T. Karan, A. Aydin, Anticancer Potential and Cytotoxic Effect of some Freshwater Cyanobacteria, Trop, J. Pharm, Res, Vol. 17, No. 11, 2018, pp. 2183-88.
[16] T. Schirmeister, S. Oli, H. Wu, G.D. Sala, V. Costantino, E. J. Seo, T. Efferth, Cytotoxicity of Endoperoxides from the Caribbean Sponge Plakortis Halichondrioides Towards Sensitive and Multidrug-Resistant Leukemia Cells: Acids vs. Esters Activity Evaluation, Mar, Drugs, Vol. 15, No. 3, 2017, pp. 63-74.
[17] A. Rasmussen, K. Murphy, D. W. Hoskin, 10-Gingerol Inhibits Ovarian Cancer Cell Growth by Inducing G2 Arrest, Adv, Pharm, Bull, Vol. 9, No. 4, 2019, pp. 685-89.
[18] Y. Nonaka, H. Ohtaki, E. Ohtsuka, T. Kocha, T. Fukuda, T. Takeuchi, T. Aoyagi, Effects of Ebelactone B, a Lipase Inhibitor, on Intestinal Fat Absorption in the Rat, J. Enzyme Inhib, Vol. 10, No. 1, 1996, pp. 57-63.
[19] L. Liu, R. Tian, S. Liu, X. Chen, L. Guo, Y. Che, Pestaloficiols A-E, Bioactive Cyclopropane Derivatives from the Plant Endophytic Fungus Pestalotiopsis Fici, Bioorg, Med, Chem, Vol. 16, No. 11, 2008, pp. 6021-26.
[20] Z. Yang, S. Longlong, L. Dong, P. Proksch, Z. Demin, L. Wenhan, A. N. Truncateols, New Isoprenylated Cyclohexanols from the Sponge-associated Fungus Truncatella Angustata with Anti-H1N1 Virus Activities, Tetrahedron, Vo. 71, No. 18, 2015, pp. 2708-18.
[21] J. Dai, K. Krohn, D. Gehle, I. Kock, U. Flörke, H. J. Aust, S. Draeger, B. Schulz, J. Rheinheimer, New Oblongolides Isolated from the Endophytic Fungus Phomopsis sp. from Melilotus Dentata from the Shores of the Baltic Sea, Eur, J. Org, Chem, Vol. 18, 2005, pp. 3351-59.
[22] W. L. Mei, B. Zheng, Y. X. Zhao, H. M. Zhong, X. L. W. Chen, Y. B. Zeng, W. H. Dong, J. L. Huang, P. Proksch, H. F. Dai, Meroterpenes from Endophytic Fungus A1 of Mangrove Plant Scyphiphora Hydrophyllacea, Mar, Drugs, Vol. 10, No. 9, 2012, pp. 1993-2001.
[23] D. T. Youssef, A. N. Singab, R. W. van Soest, N. Fusetani, Hyrtiosenolides A and B, Two New Sesquiterpene Gamma-methoxybutenolides and a New Sterol from a Red Sea Sponge Hyrtios Species, J. Nat, Prod, Vol. 67, No. 10, 2004, pp. 1736-39.
[24] L. Chen, W. Liu, X. Hu, K. Huang, J. L. Wu, Q. Q. Zhang, Citrinin Derivatives from the Marine-Derived Fungus Penicillium citrinum, Chem. Pharm. Bull, Vol. 59, No 4, 2011, pp. 515-17.
[25] N. Cho, T. T. Ransom, J. Sigmund, T. Tran, R. H. Cichewicz, M. Goetz, J. A. Beutler, Growth Inhibition of Colon Cancer and Melanoma Cells by Versiol Derivatives from a Paraconiothyrium Species, J. Nat, Prod, Vol. 80, No. 7, 2017, pp. 2037-44.
[26] L. Liu, S. Liu, S. Niu, L. Guo, X. Chen, Y. Che, Isoprenylated Chromone Derivatives from the Plant Endophytic Fungus Pestalotiopsis fici, J. Nat, Prod, Vol. 72, No. 8, 2009, pp. 1482-86.