Cytotoxic activity, molecular docking, pharmacokinetic properties and quantum mechanics calculations of the brown macroalga Cystoseira trinodis compounds

References

• Abd El-Mageed, H. R., Mustafa, F. M., & Abdel-Latif, M. K. (2020). The ability of gold nanoclusters as a new nanocarrier for D-penicillamine anticancer drug: A computational chemistry study. Structural Chemistry, 31(2), 781–793. https://doi.org/10.1007/s11224-019-01462-2
   Web of Science ®Google Scholar
• Abdelgawad, M. A., Belal, A., & Ahmed, O. M. (2013). Synthesis, molecular docking studies and cytotoxic screening of certain novel thiazolidinone derivatives substituted with benzothiazole or benzoxazole. Journal of Chemical and Pharmaceutical Research, 5(2), 318–327.
   Google Scholar
• Abd-Elzaher, M. M., Labib, A. A., Mousa, H. A., Moustafa, S. A., Ali, M. M., & El-Rashedy, A. A. (2016). Synthesis, anticancer activity and molecular docking study of Schiff base complexes containing thiazole moiety. Beni-Suef University Journal of Basic and Applied Sciences, 5(1), 85–96. https://doi.org/10.1016/j.bjbas.2016.01.001
   Google Scholar
• Abe, M., Ito, Y., Suzuki, A., Onoue, S., Noguchi, H., & Yamada, S. (2009). Isolation and pharmacological characterization of fatty acids from saw palmetto extract. Analytical Sciences, 25(4), 553–557. https://doi.org/10.2116/analsci.25.553
   PubMed Web of Science ®Google Scholar
• Abourriche, A., Charrouf, M., Berrada, M., Bennamara, A., Chaib, N., & Francisco, C. (1999). Antimicrobial activities and cytotoxicity of the brown alga Cystoseira tamariscifolia. Fitoterapia, 70(6), 611–614. https://doi.org/10.1016/S0367-326X(99)00088-XGet https://doi.org/10.1016/S0367-326X(99)00088-X
   Google Scholar
• Agoramoorthy, G., Chandrasekaran, M., Venkatesalu, V., & Hsu, M. J. (2007). Antibacterial and antifungal activities of fatty acid methyl esters of the blind-your-eye mangrove from India. Brazilian Journal of Microbiology, 38(4), 739–742. https://doi.org/10.1590/S1517-83822007000400028
   Web of Science ®Google Scholar
• Alarif, W. M., Basaif, S. A., Badria, F. A., & Ayyadd, S. N. (2015). Two new cytotoxic C-29 steroids from the red sea brown alga Cystoseira trinodis. Chemistry of Natural Compounds, 51(4), 697–702. https://doi.org/10.1007/s10600-015-1387-4
   Web of Science ®Google Scholar
• Al-Mayah, G. A. J. S., & Athbi, A. (2015). Cytotoxic activity of Enteromorpha intestinalis extracts against tumor cell-line HeLa. Journal of Biology, Agriculture and Healthcare, 5(24), 17–21.
   Google Scholar
• Araujo, G. S., Matos, L. J., Fernandes, J. O., Cartaxo, S. J., Gonçalves, L. R., Fernandes, F. A., & Farias, W. R. (2013). Extraction of lipids from microalgae by ultrasound application: Prospection of the optimal extraction method. Ultrasonics Sonochemistry, 20(1), 95–98. https://doi.org/10.1016/j.ultsonch.2012.07.027
   PubMed Web of Science ®Google Scholar
• Awad, N. E., Motawe, H. M., Selim, M. A., & Matloub, A. A. (2009). Antitumourigenic polysaccharides isolated from the brown algae, Padina pavonia (L.) Gaill. and Hydroclathrus clathratus (C. Agardh) Howe. Medicinal and Aromatic Plant Science and Biotechnology, 3(1), 6–11.
   Google Scholar
• Azarhazin, E., Izadyar, M., & Housaindokht, M. R. (2018). Molecular dynamic simulation and DFT study on the drug-DNA interaction; crocetin as an anti-cancer and DNA nanostructure model. Journal of Biomolecular Structure & Dynamics, 36(4), 1063–1074. https://doi.org/10.1080/07391102.2017.1310060
   PubMed Web of Science ®Google Scholar
• Bader, R. F. (1991). A quantum theory of molecular structure and its applications. Chemical Reviews, 91(5), 893–928. https://doi.org/10.1021/cr00005a013
   Web of Science ®Google Scholar
• Baidya, M., Griffin, K. A., & Yamamoto, H. (2012). Catalytic enantioselective O-nitrosocarbonyl aldol reaction of β-dicarbonyl compounds. Journal of the American Chemical Society, 134(45), 18566–18569. https://doi.org/10.1021/ja309311z
   PubMed Web of Science ®Google Scholar
• Barreto, M. D. C., Mendonça, E. A., Gouveia, V. F., Anjos, C., Medeiros, J. S., Seca, A. M., & Neto, A. I. (2012). Macroalgae from S. Miguel Island as a potential source of antiproliferative and antioxidant products. Arquipélago. Life and Marine Sciences, 29, 53–58.
   Google Scholar
• Bhati, S., Kaushik, V., & Singh, J. (2019). In silico identification of piperazine linked thiohydantoin derivatives as novel androgen antagonist in prostate cancer treatment. International Journal of Peptide Research and Therapeutics, 25(3), 845–860. https://doi.org/10.1007/s10989-018-9734-5
   Web of Science ®Google Scholar
• Bouzidi, N., Viano, Y., Ortalo-Magné, A., Seridi, H., Alliche, Z., Daghbouche, Y., Culioli, G., & El Hattab, M. (2019). Sterols from the brown alga Cystoseira foeniculacea: Degradation of fucosterol into saringosterol epimers. Arabian Journal of Chemistry, 12(7), 1474–1478. https://doi.org/10.1016/j.arabjc.2014.11.004
   Web of Science ®Google Scholar
• Boxall, A. B. (2004). The environmental side effects of medication. EMBO Reports, 5(12), 1110–1116. https://doi.org/10.1038/sj.embor.7400307
   PubMed Web of Science ®Google Scholar
• Carrillo, C., Cavia, M. D. M., & Alonso-Torre, S. R. (2012). Antitumor effect of oleic acid; mechanisms of action: A review. Nutricion Hospitalaria, 27(6), 1860–1865. https://doi.org/10.3305/nh.2012.27.6.6010
   PubMed Web of Science ®Google Scholar
• Chen, L. M., Liu, J., Chen, J. C., Tan, C. P., Shi, S., Zheng, K. C., & Ji, L. N. (2008). Synthesis, characterization, DNA-binding and spectral properties of complexes [Ru(L)4(dppz)]2+ (L = Im and MeIm). Journal of Inorganic Biochemistry, 102(2), 330–341. https://doi.org/10.1016/j.jinorgbio.2007.09.006
   PubMed Web of Science ®Google Scholar
• Chen, Z., Liu, J., Fu, Z., Ye, C., Zhang, R., Song, Y., Zhang, Y., Li, H., Ying, H., & Liu, H. (2014). 24(S)-Saringosterol from edible marine seaweed Sargassum fusiforme is a novel selective LXRβ agonist. Journal of Agricultural and Food Chemistry, 62(26), 6130–6137. https://doi.org/10.1021/jf500083r
   PubMed Web of Science ®Google Scholar
• Chingizova, E. A., Skriptsova, A. V., Anisimov, M. M., & Aminin, D. L. (2017). Antimicrobial activity of marine algal extracts. International Journal of Phytomedicine, 9(1), 113–122. https://doi.10.5138/09750185.1959
   Google Scholar
• Cho, J. Y. (2012). Glycoglycerolipids isolated from marine derived Streptomyces coelescens PK206-15. Bioscience, Biotechnology, and Biochemistry, 76(9), 1746–1751. https://doi.org/10.1271/bbb.120354
   PubMed Web of Science ®Google Scholar
• Deyab, M., El-Sayed, A., Abdel-Mogib, M., & Abu Ahmed, S. (2015). Hypoglycemic and cytotoxic effects of the brown alga Cystoseira trinodis and the blue-green alga Microcystis aeruginosa extracts. Catrina: The International Journal of Environmental Sciences, 14(1), 19–29.
   Google Scholar
• Discovery Studio, version 2.1. Accelrys Inc., San Diego, CA.
   Google Scholar
• El-Mageed, H. A., & Taha, M. (2019). Exploring the intermolecular interaction of serine and threonine dipeptides with gold nanoclusters and nanoparticles of different shapes and sizes by quantum mechanics and molecular simulations. Journal of Molecular Liquids, 296, 111903. https://doi.org/10.1016/j.molliq.2019.111903
   Web of Science ®Google Scholar
• Etcherla, M., & Rao, G. N. (2014). In vitro study of antimicrobial activity in marine algae Caulerpa taxifolia and Caulerpa racemosa (C. Agardh). International Journal of Applied Biology and Pharmaceutical Technology, 5(2), 57–62.
   Google Scholar
• Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., … Nakatsuji, H. (2009). Gaussian 09 Revision D. 01. Gaussian Inc. http://www.gaussian.com.
   Google Scholar
• Gomha, S. M., Riyadh, S. M., Mahmmoud, E. A., & Elaasser, M. M. (2015). Synthesis and anticancer activities of thiazoles, 1, 3-thiazines, and thiazolidine using chitosan-grafted-poly (vinylpyridine) as basic catalyst. Heterocycles, 91(6), 1227–1243. 10.1007/s10593-016-1815-9
   Web of Science ®Google Scholar
• Grabarczyk, M., Wińska, K., Mączka, W., Potaniec, B., & Anioł, M. (2015). Loliolide–the most ubiquitous lactone. Folia Biologica et Oecologica, 11(1), 1–8. https://doi.org/10.1515/fobio-2015-0001
   Google Scholar
• Güner, A., Köksal, C., Erel, Ş. B., Kayalar, H., Nalbantsoy, A., Sukatar, A., & Yavaşoğlu, N. Ü. K. (2015). Antimicrobial and antioxidant activities with acute toxicity, cytotoxicity and mutagenicity of Cystoseira compressa (Esper) Gerloff & Nizamuddin from the coast of Urla (Izmir, Turkey). Cytotechnology, 67(1), 135–143. https://doi.org/10.1007/s10616-013-9668-x
   PubMed Web of Science ®Google Scholar
• Hindler, J. A., Howard, B. J., & Keiser, J. F. (1994). Antimicrobial agents and antimicrobial susceptibility testing. In B. J. Howard (Ed.), Clinical and pathogenic microbiology (2nd ed.). Mosby.
   Google Scholar
• Hughes, Z. E., & Walsh, T. R. (2016). Non-covalent adsorption of amino acid analogues on noble-metal nanoparticles: Influence of edges and vertices. Physical Chemistry Chemical Physics: PCCP, 18(26), 17525–17533. https://doi.org/10.1039/c6cp02323a
   PubMed Web of Science ®Google Scholar
• Ibraheem, I. B. M., Abdel-Raouf, N., Abdel-Hameed, M. S., & El-Yamany, K. (2012). Antimicrobial and antiviral activities against Newcastle disease virus (NDV) from marine algae isolated from Qusier and Marsa-Alam Seashore (Red Sea), Egypt. African Journal of Biotechnology, 11(33), 8332–8340. https://doi.org/10.5897/AJB11.3982
   Google Scholar
• Imbs, T. I., Ermakova, S. P., Fedoreyev, S. A., Anastyuk, S. D., & Zvyagintseva, T. N. (2013). Isolation of fucoxanthin and highly unsaturated monogalactosyldiacylglycerol from brown alga Fucus evanescens C Agardh and in vitro investigation of their antitumor activity. Marine Biotechnology, 15(5), 606–612. https://doi.org/10.1007/s10126-013-9507-2
   PubMed Web of Science ®Google Scholar
• Karabay-Yavasoglu, N. U., Sukatar, A., Ozdemir, G., & Horzum, Z. (2007). Antimicrobial activity of volatile components and various extracts of the red alga Jania rubens. Phytotherapy Research: PTR, 21(2), 153–156. https://doi.org/10.1002/ptr.2045
   PubMed Web of Science ®Google Scholar
• Khanavi, M., Nabavi, M., Sadati, N., Shams Ardekani, M., Sohrabipour, J., Nabavi, S. M. B., Ghaeli, P., & Ostad, S. N. (2010). Cytotoxic activity of some marine brown algae against cancer cell lines. Biological Research, 43(1), 31–37. https://doi.org/10.4067/S0716-97602010000100005
   PubMed Web of Science ®Google Scholar
• Kim, J. S., Shim, S. H., Chae, S., Han, S. J., Kang, S. S., Son, K. H., Chang, H. W., Kim, H. P., & Bae, K. (2005). Saponins and other constituents from the leaves of Aralia elata. Chemical & Pharmaceutical Bulletin, 53(6), 696–700. https://doi.org/10.1248/cpb.53.696
   PubMed Web of Science ®Google Scholar
• Klingmüller, U., Schilling, M., Depner, S., & D’Alessandro, L. A. (2013). Biological foundations of signal transduction, systems biology and aberrations in disease. In Andres Kriete (Ed.), Computational systems biology: From molecular mechanisms to disease (2nd ed., pp. 45–64). Elsevier Inc. https://doi.org/10.1016/B978-0-12-405926-9.00004-6
   Google Scholar
• König, G. M., & Wright, A. D. (1997). Laurencia rigida: Chemical investigations of its antifouling dichloromethane extract. Journal of Natural Products, 60(10), 967–970. https://doi.org/10.1021/np970181r
   PubMed Web of Science ®Google Scholar
• Kosanić, M., Ranković, B., & Stanojković, T. (2015). Biological activities of two macroalgae from Adriatic coast of Montenegro. Saudi Journal of Biological Sciences, 22(4), 390–397. https://doi.org/10.1016/j.sjbs.2014.11.004
   PubMed Web of Science ®Google Scholar
• Lee, T. C., Yang, W. T., & Parr, R. G. (1988). Density-functional crystal orbital study on the structures and energetics of polyacetylene isomers. Physical Review B, 37(2), 785–789. https://doi.org/10.1103/PhysRevB.37.785
   PubMed Web of Science ®Google Scholar
• Li, J., Chen, J. C., Xu, L. C., Zheng, K. C., & Ji, L. N. (2007). A DFT/TDDFT study on the structures, trend in DNA-binding and spectral properties of molecular “light switch” complexes [Ru (phen) 2 (L)] 2+(L = dppz, taptp, phehat). Journal of Organometallic Chemistry, 692(4), 831–838. https://doi.org/10.1016/j.jorganchem.2006.10.029
   Web of Science ®Google Scholar
• Li, X., Chen, L., Cheng, F., Wu, Z., Bian, H., Xu, C., Li, W., Liu, G., Shen, X., & Tang, Y. (2014). In silico prediction of chemical acute oral toxicity using multi-classification methods. Journal of Chemical Information and Modeling, 54(4), 1061–1069. https://doi.org/10.1021/ci5000467
   PubMed Web of Science ®Google Scholar
• Lordan, S., Ross, R. P., & Stanton, C. (2011). Marine bioactives as functional food ingredients: Potential to reduce the incidence of chronic diseases. Marine Drugs, 9(6), 1056–1100. https://doi.org/10.3390/md9061056
   PubMed Web of Science ®Google Scholar
• Marenich, A. V., Cramer, C. J., & Truhlar, D. G. (2009). Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. The Journal of Physical Chemistry B, 113(18), 6378–6396. https://doi.org/10.1021/jp810292n
   PubMed Web of Science ®Google Scholar
• Mericli, F., Becer, E., Kabadayı, H., Hanoglu, A., Yigit Hanoglu, D., Ozkum Yavuz, D., Ozek, T., & Vatansever, S. (2017). Fatty acid composition and anticancer activity in colon carcinoma cell lines of Prunus dulcis seed oil. Pharmaceutical Biology, 55(1), 1239–1248. https://doi.org/10.1080/13880209.2017.1296003
   PubMedGoogle Scholar
• Miertuš, S., Scrocco, E., & Tomasi, J. (1981). Electrostatic interaction of a solute with a continuum. A direct utilizaion of AB initio molecular potentials for the prevision of solvent effects. Chemical Physics, 55(1), 117–129. https://doi.org/10.1016/0301-0104(81)85090-2
   Web of Science ®Google Scholar
• Mohamad, H., Jamil, W. A. N. W. A., Abas, F., Mohamad, K. S., & Ali, A. M. (2009). Octacosanoic acid, long chains saturated fatty acid from the marine sponges Xestospongia sp. Pertanika Journal of Tropical and Agriculture Science, 32(1), 51–55.
   Google Scholar
• Mohy El-Din, S. M., & El-Ahwany, A. M. (2016). Bioactivity and phytochemical constituents of marine red seaweeds (Jania rubens, Corallina mediterranea and Pterocladia capillacea). Journal of Taibah University for Science, 10(4), 471–484. https://doi.org/10.1016/j.jtusci.2015.06.004
   Web of Science ®Google Scholar
• Morris, G. M., Goodsell, D. S., Halliday, R. S., Huey, R., Hart, W. E., Belew, R. K., & Olson, A. J. (1998). Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. Journal of Computational Chemistry, 19(14), 1639–1662. https://doi.org/10.1002/(SICI)1096-987X(19981115) https://doi.org/10.1002/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B
   Web of Science ®Google Scholar
• Mosmann, T. (1983). Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. Journal of Immunological Methods, 65(1–2), 55–63. https://doi.org/10.1016/0022-1759(83)90303-4
   PubMed Web of Science ®Google Scholar
• Murugavel, S., Sundramoorthy, S., Lakshmanan, D., Subashini, R., & Kumar, P. P. (2017). Synthesis, crystal structure analysis, spectral (NMR, FT-IR, FT-Raman and UV–Vis) investigations, molecular docking studies, antimicrobial studies and quantum chemical calculations of a novel 4-chloro-8-methoxyquinoline-2 (1H)-one: An effective antimicrobial agent and an inhibition of DNA gyrase and lanosterol-14α-demethylase enzymes. Journal of Molecular Structure, 1131, 51–72. https://doi.org/10.1016/j.molstruc.2016.11.035
   Web of Science ®Google Scholar
• Nakayama, M., Fukuoka, Y., Nozaki, H., Matsuo, A., & Hayashi, S. (1980). Structure of (+)-kjellmanianone, a highly oxygenated cyclopentenone from the marin alga, Sargassum kjellmanianum. Chemistry Letters, 9(10), 1243–1246. https://doi.org/10.1246/cl.1980.1243
   Web of Science ®Google Scholar
• Ododo, M. M., Choudhury, M. K., & Dekebo, A. H. (2016). Structure elucidation of β-sitosterol with antibacterial activity from the root bark of Malva parviflora. SpringerPlus, 5(1), 1–11. https://doi.org/10.1186/s40064-016-2894-x
   PubMedGoogle Scholar
• Percot, A., Yalçın, A., Aysel, V., Erduğan, H., Dural, B., & Güven, K. C. (2009). Loliolide in marine algae. Natural Product Research, 23(5), 460–465. https://doi.10.1080/14786410802076069 https://doi.org/10.1080/14786410802076069
   PubMed Web of Science ®Google Scholar
• Pérez, M. J., Falqué, E., & Domínguez, H. (2016). Antimicrobial action of compounds from marine seaweed. Marine Drugs, 14(3), 52. https://doi.org/10.3390/md14030052
   PubMed Web of Science ®Google Scholar
• Prabhadevi, V., Sahaya, S. S., Johnson, M., Venkatramani, B., & Janakiraman, N. (2012). Phytochemical studies on Allamanda cathartica L. using GC–MS. Asian Pacific Journal of Tropical Biomedicine, 2(2), S550–S554. https://doi.org/10.1016/S2221-1691(12)60272-X
   Google Scholar
• Ross, R. B., Powers, J. M., Atashroo, T., Ermler, W. C., LaJohn, L. A., & Christiansen, P. A. (1990). A binitio relativistic effective potentials with spin–orbit operators. IV. Cs through Rn. The Journal of Chemical Physics, 93(9), 6654–6670. https://doi.org/10.1063/1.458934
   Web of Science ®Google Scholar
• Salem, A. B., Di Giuseppe, G., Anesi, A., Hammami, S., Mighri, Z., & Guella, G. (2017). Natural products among brown algae: The case of Cystoseira schiffneri Hamel (Sargassaceae, Phaeophyceae). Chemistry & Biodiversity, 14(4), e1600333. https://doi.org/10.1002/cbdv.201600333
   Web of Science ®Google Scholar
• Sandsdalen, E., Haug, T., Stensvåg, K., & Styrvold, O. B. (2003). The antibacterial effect of a polyhydroxylated fucophlorethol from the marine brown alga, Fucus vesiculosus. World Journal of Microbiology and Biotechnology, 19(8), 777–782. https://doi.org/10.1023/A:1026052715260
   Web of Science ®Google Scholar
• Sathya, R., Kanaga, N., Sankar, P., & Jeeva, S. (2017). Antioxidant properties of phlorotannins from brown seaweed Cystoseira trinodis (Forsskål) C. Agardh. Arabian Journal of Chemistry, 10, S2608–S2614. https://doi.org/10.1016/j.arabjc.2013.09.039
   Web of Science ®Google Scholar
• Seenivasan, R., Rekha, M., & Indu, H. (2012). Antibacterial activity and phytochemical analysis of selected seaweeds from Mandapam Coast. India. Journal of Applied Pharmaceutical Science, 2(10), 159. 10.7324/JAPS.2012.21030
   Google Scholar
• Selim, S. A. (2012). Antimicrobial, antiplasmid and cytotoxicity potentials of marine algae Halimeda opuntia and Sarconema filiforme collected from Red Sea Coast. World Academy of Science, Engineering and Technology, 6(1), 1154–1159.
   Google Scholar
• Singh, M. J., & Raadha, C. K. (2015). Studies on the antimicrobial potency of the marine algae Gracilaria corticata var cylindrica and Hydroclathrus clathratus. Advanced Life Sciences for Health, 2, 50–55.
   Google Scholar
• Smoot, M. E., Ono, K., Ruscheinski, J., Wang, P. L., & Ideker, T. (2011). Cytoscape 2.8: New features for data integration and network visualization. Bioinformatics, 27(3), 431–432. https://doi.org/10.1093/bioinformatics/btq675
   PubMed Web of Science ®Google Scholar
• Stein, E. M., Andreguetti, D. X., Rocha, C. S., Fujii, M. T., Baptista, M. S., Colepicolo, P., & Indig, G. L. (2011). Search for cytotoxic agents in multiple Laurencia complex seaweed species (Ceramiales, Rhodophyta) harvested from the Atlantic Ocean with emphasis on the Brazilian State of Espírito Santo. Revista Brasileira de Farmacognosia, 21(2), 239–243. https://doi.org/10.1590/S0102-695X2011005000069
   Google Scholar
• Stirk, W. A., Reinecke, D. L., & van Staden, J. (2007). Seasonal variation in antifungal, antibacterial and acetylcholinesterase activity in seven South African seaweeds. Journal of Applied Phycology, 19(3), 271–276. https://doi.org/10.1007/s10811-006-9134-7
   Web of Science ®Google Scholar
• Sultana, S., Ali, M., & Jameel, M. (2018). Aliphatic constituents from the leaves of Dillenia indica L., Halothamus bottae Jaub. and Xylosma longifolium Clos. Chemistry Research Journal, 3(3), 109–117.
   Google Scholar
• Tajbakhsh, S., Ilkhani, M., Rustaiyan, A., Larijani, K., Sartavi, K., Tahmasebi, R., & Asayesh, G. (2011). Antibacterial effect of the brown alga Cystoseira trinodis. Journal of Medicinal Plants Research, 5(18), 4654–4657.
   Google Scholar
• Taskin, E., Caki, Z., & Ozturk, M. (2010). Assessment of in vitro antitumoral and antimicrobial activities of marine algae harvested from the eastern Mediterranean sea. African Journal of Biotechnology, 9(27), 4272–4277.
   Google Scholar
• Tüney, İ., Cadirci, B. H., Ünal, D., & Sukatar, A. (2013). Antimicrobial activities of the extracts of marine algae from the coast of Urla (Izmir, Turkey). Turkish Journal of Biology, 37(3), 171–175. https://doi.org/10.3906/biy-1205-40
   Google Scholar
• Usman, M., Arjmand, F., Ahmad, M., Khan, M. S., Ahmad, I., & Tabassum, S. (2016). A comparative analyses of bioactive Cu (II) complexes using Hirshfeld surface and density functional theory (DFT) methods: DNA binding studies, cleavage and antibiofilm activities. Inorganica Chimica Acta, 453, 193–201. https://doi.org/10.1016/j.ica.2016.08.011
   Web of Science ®Google Scholar
• van der Watt, E., & Pretorius, J. C. (2013). A triglyceride from Lupinus albus L. seed with biostimulatory properties. African Journal of Biotechnology, 12(35), 5431–5443. https://doi.org/10.5897/AJB12.2851
   Google Scholar
• Vlachos, V., Critchley, A. T., & Von Holy, A. (1997). Antimicrobial activity of extracts from selected southern African marine macroalgae. South African Journal of Science, 93(7), 328–332.
   Web of Science ®Google Scholar
• Xu, N., Fan, X., Yan, X., & Tseng, C. K. (2004). Screening marine algae from China for their antitumor activities. Journal of Applied Phycology, 16(6), 451–456. https://doi.org/10.1007/s10811-004-5508-x
   Web of Science ®Google Scholar
• Yang, X., Kang, M. C., Lee, K. W., Kang, S. M., Lee, W. W., & Jeon, Y. J. (2011). Antioxidant activity and cell protective effect of loliolide isolated from Sargassum ringgoldianum subsp. coreanum. Algae, 26(2), 201–208. https://doi.org/10.4490/algae.2011.26.2.201
   Google Scholar
• Yi, Z., Yin-Shan, C., & Hai-Sheng, L. U. (2001). Screening for antibacterial and antifungal activities in some marine algae from the Fujian coast of China with three different solvents. Chinese Journal of Oceanology and Limnology, 19(4), 327–331. https://doi.org/10.1007/BF02850736
   Google Scholar
• Yuan, Z., Zheng, X., Zhao, Y., Liu, Y., Zhou, S., Wei, C., Hu, Y., & Shao, H. (2018). Phytotoxic compounds isolated from leaves of the invasive weed Xanthium spinosum. Molecules, 23(11), 2840–2812. https://doi.org/10.3390/molecules23112840
   Web of Science ®Google Scholar
• Zhang, J., Li, C., Yu, G., & Guan, H. (2014). Total synthesis and structure-activity relationship of glycoglycerolipids from marine organisms. Marine Drugs, 12(6), 3634–3659. https://doi.org/10.3390/md12063634
   PubMed Web of Science ®Google Scholar
• Zhao, P., Xu, L. C., Huang, J. W., Liu, J., Yu, H. C., Zheng, K. C., & Ji, L. N. (2008). Experimental and DFT studies on DNA binding and photocleavage of two cationic porphyrins: Effects of the introduction of a carboxyphenyl into pyridinium porphyrin. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 71(4), 1216–1223. https://doi.org/10.1016/j.saa.2008.03.031
   PubMed Web of Science ®Google Scholar
• Zubia, M., Fabre, M. S., Kerjean, V., Le Lann, K., Stiger-Pouvreau, V., Fauchon, M., & Deslandes, E. (2009). Antioxidant and antitumoural activities of some Phaeophyta from Brittany coasts. Food Chemistry, 116(3), 693–701. https://doi.org/10.1016/j.foodchem.2009.03.025
   Web of Science ®Google Scholar