Research article Special Issues

Biotesting of technologically important carboxy containing acridones with solid-state fungal culture

  • Received: 06 September 2020 Accepted: 21 October 2020 Published: 26 October 2020
  • To develop environmentally adapted products, there is a necessity of getting information about the environmental impact of acridone derivatives commonly recognized to possess a variety of biological activities. Acridones are widespread in nature, but the issue related to the acridone series compounds effect on mushrooms still remains practically unstudied. Fungi are a group of living organisms very interesting in theoretical and practical respect. One of the first macrofungi to be cultivated at large scale was the basidiomycete Lentinula edodes (Berk.) Pegler, otherwise known as shiitake. Research into the character of the mode of action of acridone-based substances on various living systems is necessary to elucidate the possible unfavorable biological consequences and to improve measures on their ecological safety. This work reports on the effect of acridone, 1-carboxyacridone, and acridone-N-acetic acid on shiitake mushroom agar culture. Chromato-mass spectrometric analysis was performed in the mode of gas chromatography with mass-selective detection (GC-MS) to follow the decomposition of acridone and its carboxy derivatives by L. edodes culture in solid-state fermentation. The results obtained testify to the relative ecological safety of these substances for mushroom organism, and to the mycelial growth promoting capability of acridone-N-acetic acid at favorable concentrations under these culture conditions. The next step toward the investigation into the systems “macromycete - acridone series compound” has been made.

    Citation: Olga M. Tsivileva, Inna M. Uchaeva, Nikolay A. Yurasov. Biotesting of technologically important carboxy containing acridones with solid-state fungal culture[J]. AIMS Bioengineering, 2021, 8(1): 1-13. doi: 10.3934/bioeng.2021001

    Related Papers:

  • To develop environmentally adapted products, there is a necessity of getting information about the environmental impact of acridone derivatives commonly recognized to possess a variety of biological activities. Acridones are widespread in nature, but the issue related to the acridone series compounds effect on mushrooms still remains practically unstudied. Fungi are a group of living organisms very interesting in theoretical and practical respect. One of the first macrofungi to be cultivated at large scale was the basidiomycete Lentinula edodes (Berk.) Pegler, otherwise known as shiitake. Research into the character of the mode of action of acridone-based substances on various living systems is necessary to elucidate the possible unfavorable biological consequences and to improve measures on their ecological safety. This work reports on the effect of acridone, 1-carboxyacridone, and acridone-N-acetic acid on shiitake mushroom agar culture. Chromato-mass spectrometric analysis was performed in the mode of gas chromatography with mass-selective detection (GC-MS) to follow the decomposition of acridone and its carboxy derivatives by L. edodes culture in solid-state fermentation. The results obtained testify to the relative ecological safety of these substances for mushroom organism, and to the mycelial growth promoting capability of acridone-N-acetic acid at favorable concentrations under these culture conditions. The next step toward the investigation into the systems “macromycete - acridone series compound” has been made.


    加载中


    Author contributions



    Olga M. Tsivileva, Inna M. Uchaeva and Nikolay A. Yurasov carried out the laboratory work. Olga M. Tsivileva produced the first draft of the work and oversaw subsequent manuscript preparation. Inna M. Uchaeva was involved in the manuscript preparation and writing. Nikolay A. Yurasov designed the conceptualisation of treating the data derived from the chromatographic analysis within project. Olga M. Tsivileva oversaw the project.

    Conflict of interest



    The authors declare no conflict of interest.

    [1] Hagiwara Y, Hasegawa T, Shoji A, et al. (2008) Acridone-tagged DNA as a new probe for DNA detection by fluorescence resonance energy transfer and for mismatch DNA recognition. Bioorgan Med Chem 16: 7013-7020.
    [2] Wang N, Zhang B, Jin F, et al. (2018) Combing metabolomics with bioanalysis methods to study the antitumor mechanism of the new acridone derivative 8q on CCRF-CEM cells: 8q induced mitochondrial-mediated apoptosis and targeted the PI3K/AKT/FOXO1 pathway. J Pharmaceut Biomed 160: 314-322.
    [3] Xia YK, He WH, Li J, et al. (2019) Acridone derivate simultaneously featuring multiple functions and its applications. Anal Chem 91: 8406-8414.
    [4] Oyedele AS, Bogan DN, Okoro CO (2020) Synthesis, biological evaluation and virtual screening of some acridone derivatives as potential anticancer agents. Bioorgan Med Chem 28: 115426.
    [5] Dos Santos DAP, Vieira PC, Da Silva MFGF, et al. (2009) Antiparasitic activities of acridone alkaloids from Swinglea glutinosa (Bl.) Merr. J Braz Chem Soc 20: 644-651.
    [6] Mohammedi H, Mecherara-Idjeri S, Hassani A (2020) Variability in essential oil composition, antioxidant and antimicrobial activities of Ruta montana L. collected from different geographical regions in Algeria. J EssentOil Res 32: 88-101.
    [7] Tsassi BV, Hussain H, Geagni A, et al. (2011) Citropremide and citropridone: a new ceramide and a new acridone alkaloid from the atem bark of Citropsis gabunensisHelv Chim Acta 94: 1035-1040.
    [8] Delektorskii VV, Malinovskaia VV, Strizhakov AN, et al. (1995) The interferon inducer neovir (kamedon) in the combined treatment of chronic inflammatory diseases of the adnexa uteri of chlamydial etiology (a clinical electron-microscopic study). Antibiot Khimioter 40: 42-47.
    [9] Zabezhinskii MA, Popovich IG, Shtylik AV, et al. (1998) The effect of cycloferon administration on the growth of transplantable tumors in rats and mice. Vopr Onkol 44: 427-431.
    [10] Khomenko RM, Kryachko OV, Lukoyanova LA (2018) The influence of the drug “Anandin” on some immunological indicators in sows during gestation and lactation. Int Bull Vet Med 3: 58-62.
    [11] Goodell JR, Madhok AA, Hiasa H, Ferguson DM (2006) Synthesis and evaluation of acridine-and acridone-based anti-herpes agents with topoisomerase activity. Bioorgan Med Chem 14: 5467-5480.
    [12] Souto AL, Tavares JF, Da Silva MS, et al. (2011) Anti-inflammatory activity of alkaloids: an update from 2000 to 2010. Molecules 16: 8515-8534.
    [13] Michael JP (2004) Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep 21: 650-668.
    [14] Itoigawa M, Ito C, Wu TS, et al. (2003) Cancer chemopreventive activity of acridone alkaloids on Epstein–Barr virus activation and two-stage mouse skin carcinogenesis. Cancer Lett 193: 133-138.
    [15] Wu TS, Shi LS, Wang JJ, et al. (2003) Cytotoxic and antiplatelet aggregation principles of Ruta graveolensJ Chin Chem Soc Taip 50: 171-178.
    [16] Rajendra Prasad VVS, Reddy GD, Kathmann I, et al. (2016) Nitric oxide releasing acridone carboxamide derivatives as reverters of doxorubicin resistance in MCF7/Dx cancer cells. Bioorg Chem 64: 51-58.
    [17] Murahari M, Prakash KV, Peters GJ, et al. (2017) Acridone-pyrimidine hybrids-design, synthesis, cytotoxicity studies in resistant and sensitive cancer cells and molecular docking studies. Eur J MedChem 139: 961-981.
    [18] Dallavalle S, Dobričić V, Lazzarato L, et al. (2020) Improvement of conventional anti-cancer drugs as new tools against multidrug resistant tumors. Drug Resist Updat 50: 100682.
    [19] Chukaew A, Ponglimanont C, Karalai C, et al. (2008) Potential anti-allergic acridone alkaloids from the roots of Atalantia monophyllaPhytochemistry 69: 2616-2620.
    [20] De Oliveira DBC, Silva LB, da Silva BV, et al. (2019) A new acridone with antifungal properties against Candida spp. and dermatophytes, and antibiofilm activity against C. albicansJ Appl Microbiol 127: 1362-1372.
    [21] Michael P (2008) Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep 25: 166-187.
    [22] Markovich YD, Kudryavtseva TN, Bogatyrev KV, et al. (2014) Synthesis of 2-(4-methyl-1, 3-thiazol-5-yl) ethyl esters of acridone carboxylic acids and evaluation of their antibacterial activity. Russ Chem Bull 63: 1153-1158.
    [23] Kudryavtseva TN, Lamanov AY, Klimova LG, et al. (2017) Synthesis and antimicrobial activity of acridine carboxylic acid derivatives containing a piperazine moiety. Russ Chem Bull 66: 123-128.
    [24] Kudryavtseva TN, Lamanov AY, Klimova LG, et al. (2018) Synthesis and antibacterial activity of 9-Oxo-9, 10-dihydroacridinecarboxylic acids esters bearing a triazole fragment. Russ J Gen Chem 88: 676-681.
    [25] Markovich YD, Grekhnyova EV, Efanov SA, et al. (2011) Properties of acridone derivatives encapsulated in water-soluble polymers. Proc South-West State Univ 1: 50-55.
    [26] Markovich YD, Kudryavtseva TN, Markovich VY, et al. (2013) Sulfonation of 10-carboxymethylene-9-acridanone under thermal and microwave conditions. Comparison of kinetic parameters. Russ J Gen Chem 83: 691-693.
    [27] Castañeda-Ramírez GS, Torres-Acosta JFDJ, Sánchez JE, et al. (2020) The possible biotechnological use of edible mushroom bioproducts for controlling plant and animal parasitic nematodes. BioMed Res Int 2020: 6078917.
    [28] Fukushima-Sakuno E (2020) Bioactive small secondary metabolites from the mushrooms Lentinula edodes and Flammulina velutipesJ Antibiot 73: 687-696.
    [29] Tsivileva OM, Shaternikov AN, Nikitina VE (2020) Bacteria of the Azospirillum genus for the optimization of the artificial culture of xylotrophic mushrooms. Biotekhnologiya 36: 16-25.
    [30] Park JP, Kim SW, Hwang HJ, et al. (2001) Optimization of submerged culture conditions for the mycelial growth and exo-biopolymer production by Cordyceps militarisLett Appl Microbiol 33: 76-81.
    [31] Tsivileva OM, Pankratov AN, Nikitina VE (2010) Extracellular protein production and morphogenesis of Lentinula edodes in submerged culture. Mycol Prog 9: 157-167.
    [32] Dudka IA, Vasser SP, Ellanskaya IA, et al. (1982)  Methods of experimental mycology: Handbook Kiev, Ukraine: Naukova dumka.
    [33] Bukhalo AS (1988)  Higher edible mushrooms in pure cultures Kiev, Ukraine: Naukova Dumka.
    [34] Tsivileva ОM, Uchaeva IM, Pankratov AN, et al. (2013) First estimations of plant acridone alkaloid implemented in mushroom mycelium growth. J Agr Sci Tech 3: 873-879.
    [35] Tsivileva OM, Loshchinina EA, Makarov OE, et al. (2012) Auxin synthesis by the higher fungus Lentinus edodes (Berk.) sing in the presence of low concentrations of indole compounds. Appl Biochem Microbiol 48: 280-289.
    [36] Tsivileva OM, Pankratov AN, Misin VM, et al. (2018) Antioxidant properties of the Artist's Conk medicinal mushroom, Ganoderma applanatum (Agaricomycetes), upon cultivation with para-substituted phenolic compounds and tea leaf extracts. Int J Med Mushrooms 20: 549-560.
    [37] Kim YM, Yun J, Lee CK, et al. (2002) Oxyresveratrol and hydroxystilbene compounds inhibitory effect on tyrosinase and mechanism of action. J Biol Chem 277: 16340-16344.
  • Reader Comments
  • © 2021 the Author(s), licensee AIMS Press. This is an open access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0)
通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

Metrics

Article views(2879) PDF downloads(103) Cited by(0)

Article outline

Figures and Tables

Figures(5)  /  Tables(1)

/

DownLoad:  Full-Size Img  PowerPoint
Return
Return

Catalog