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Investigation of Biological Activity of Squamarina cartilaginea (With.) P. James Species Distributed in Türkiye

Year 2024, Volume: 45 Issue: 3, 478 - 485, 30.09.2024

Banu Ceren Değirmenci , Mustafa Kocakaya , Selen İlgün , Gökçe Şeker Karatoprak , Zekiye Kocakaya , Ahmet Ceylan

https://doi.org/10.17776/csj.1424202

Abstract

In this study, the methanol extract of Squamarina cartilaginea, a species distributed in Türkiye, was investigated for its antimicrobial, antioxidant, cytotoxic, and DNA protective effects. The chemical composition of the extract was elucidated through spectroscopic determination of total phenols, total flavonoids, and chromatographic quantification of usnic acid. Antimicrobial activity was assessed using the disk diffusion method, revealing a significant zone of inhibition with a diameter of 17.5 mm against M. luteus and S. aureus. The antioxidant activity was evaluated through scavenging activities against DPPH and ABTS radicals, demonstrating a concentration-dependent potent scavenging activity against ABTS radicals. Cytotoxic activity was determined using the MTT method on DU-145 (Human Prostate Cancer Cell Line) and Colo 205 (Human Colon Cancer Cell Line) cell lines. The extract exhibited strong cytotoxic activity against the Colo 205 cell line, with a viability percentage of 33.16±2.01 at a concentration of 3.906 µg/mL. Furthermore, the S. cartilaginea extract demonstrated DNA protective activity on pBR322 plasmid DNA against UV and H2O2 exposure.

Keywords

Cytotoxicity Lichen pBR322 Squamarina Usni acid

Supporting Institution

Yozgat Bozok Üniveristesi

Project Number

number 6601a-FBE/20-433

Thanks

This study was financially supported by the Yozgat Bozok University project with project number 6601a-FBE/20-433.

References

  • [1] Miao V., Coëffet-LeGal M. F., Brown D., Sinnemann S., Donaldson G., Davies J., Genetic approaches to harvesting lichen products, Trends in Biotechnology, 19(9) (2001) 349-355.
  • [2] Stanojković T., Investigations of lichen secondary metabolites with potential anticancer activity. Lichen secondary metabolites: bioactive properties and pharmaceutical potential, 9 (2019) 155-174.
  • [3] Shukla V., Joshi G. P., Rawat M. S. M., Lichens as a potential natural source of bioactive compounds: a review, Phytochemistry reviews, 9 (2010) 303-314.
  • [4] Illana-Esteban C. Lichens used in traditional medicine, Boletin de La Sociedad Micologica de Madrid, 36, (2012), 163-174.
  • [5] Crawford S. D., Lichens used in traditional medicine, Lichen secondary metabolites: bioactive properties and pharmaceutical potential, 9 (2019) 31-97.
  • [6] Richardson D. H. S., Lichens and man, Frontiers in mycology, 1 (1991) 187-210.
  • [7] Çobanoğlu G. ve Yavuz M., Tıp Tarihinde Likenlerle Tedavi, Yeni Tıp Tarihi Araştırmaları, 9, (2003) 37-90.
  • [8] Oksanen I., Ecological and biotechnological aspects of lichens, Applied microbiology and biotechnology, 73 (2006) 723-734.
  • [9] Paudel B., Bhattarai H. D., Lee J. S., Hong S. G., Shin H. W., Yim J. H., Antioxidant activity of polar lichens from King George Island (Antarctica), Polar Biology, 31 (2008) 605-608.
  • [10] Behera B. C., Verma N., Sonone A., Makhija U., Antioxidant and antibacterial activities of lichen Usnea ghattensis in vitro, Biotechnology letters, 27 (2005) 991-995.
  • [11] Gyawali R., Ibrahim S. A., Natural products as antimicrobial agents, Food control, 46 (2014) 412-429.
  • [12] Sharnoff S., A field guide to California lichens, Yale University Press, (2014).
  • [13] Kirk P. M., Cannon P. F., Minter D. W., & Stalpers J. A. Dictionary of the fungi Wallingford, UK: CABI, (2008), 335.
  • [14] Himmelreich U., Huneck S., Feige G. B., Lumbsch H. T., Squamaron, ein Naphthochinon aus der Flechte Squamarina cartilaginea/Squamarone, a Naphthoquinone from the Lichen Squamarina cartilaginea, Zeitschrift für Naturforschung B, 49(9) (1994) 1289-1291.
  • [15] Cansaran Duman D., Halıcı M. G., Antimicrobial activity of usnic acid on Squamarina lentigera lichen species, Turkish Bulletin of Hygiene and Experimental Biology, 69(3) (2012) 127-134.
  • [16] Sweidan A., Chollet-Krugler M., Sauvager A., Van De Weghe P., Chokr A., Bonnaure-Mallet M., Tomasi S., Bousarghin L., Antibacterial activities of natural lichen compounds against Streptococcus gordonii and Porphyromonas gingivalis, Fitoterapia, 121 (2017) 164-169.
  • [17] Reiter R. J., Acuña‐Castrovıejo D., Tan D. X., Burkhardt S., Free radical‐mediated molecular damage: mechanisms for the protective actions of melatonin in the central nervous system, Annals of the New York Academy of Sciences, 939(1) (2001) 200-215.
  • [18] Purvis O. W., Coppins B. J., Hawksworth D.L., James P. W., and Moore D. M., The Lichen Flora of Great Britain and Ireland. London: Natural History Museum Publications in association with the British Lichen Society (1992).
  • [19] Siddiq A., Anwar F., Manzoor M., Fatima M., Antioxidant activity of different solvent extracts of Moringa oleifera leaves under accelerated storage conditions of sunflower oil, Asian J. Plant Sci., 4 (2005) 630- 635.
  • [20] Karatoprak G. Ş., Göger F., Çelik İ., Budak Ü., Akkol E. K., Aschner M., Phytochemical profile, antioxidant, antiproliferative, and enzyme inhibition-docking analyses of Salvia ekimiana Celep & Doğan, South African Journal of Botany, 146 (2022) 36-47.
  • [21] Re R., Pellegrini N., Proteggente A., Pannala A., Yang M., Rice-Evans C., Antioxidant activity applying an improved ABTS radical cation decolorization assay, Free radical biology and medicine, 26 (9-10) (1999) 1231-1237.
  • [22] Zhishen J., Mengcheng T., Jianming W., The determination of flavonoid contents in mulberry and their scavenging effects on superoxide radicals, Food chemistry, 64(4) (1999) 555-559.
  • [23] Adinortey M. B., Ansah C., Weremfo A., Adinortey C. A., Adukpo G. E., Ameyaw E. O., Nyarko A. K., DNA damage protecting activity and antioxidant potential of Launaea taraxacifolia leaves extract, Journal of Natural Science, Biology, and Medicine, 9(1) (2018) 6.
  • [24] Gyamfi M. A., Yonamine M., Aniya Y., Free-radical scavenging action of medicinal herbs from Ghana: Thonningia sanguinea on experimentally-induced liver injuries, General Pharmacology: The Vascular System, 32(6) (1999) 661-667.
  • [25] Popovici V., Bucur L., Gîrd C. E., Popescu A., Matei E., Cozaru G. C., ... & Badea V. Phenolic Secondary Metabolites and Antiradical and Antibacterial Activities of Different Extracts of Usnea barbata (L.) Weber ex FH Wigg from Călimani Mountains, Romania, Pharmaceuticals, 15(7) (2022) 829.
  • [26] Kocovic A., Jeremic J., Bradic J., Sovrlic M., Tomovic J., Vasiljevic P., Manojlovic N., Phytochemical analysis, antioxidant, antimicrobial, and cytotoxic activity of different extracts of Xanthoparmelia stenophylla lichen from Stara Planina, Serbia, Plants, 11(13) (2022) 1624.
  • [27] Manojlovic N. T., Vasiljevic P. J., Maskovic P. Z., Juskovic M., Bogdanovic-Dusanovic G., Chemical composition, antioxidant, and antimicrobial activities of lichen Umbilicaria cylindrica (L.) Delise (Umbilicariaceae) Evidence-based complementary and alternative medicine, (2012).
  • [28] Campanella L., Delfini M., Ercole P., Iacoangeli A., & Risuleo G., Molecular characterization and action of usnic acid: a drug that inhibits proliferation of mouse polyomavirus in vitro and whose main target is RNA transcription, Biochimie, 84(4) (2002) 329-334.
  • [29] Fernández-Pastor I., González-Menéndez V., Martínez Andrade K., Serrano R., Mackenzie T. A., Benítez G., ... & Reyes F., Xerophytic Lichens from Gypsiferous Outcrops of Arid Areas of Andalusia as a Source of Anti-Phytopathogenic Depsides, Journal of Fungi, 9(9) (2023) 887.
  • [30] Ivanova V., Bačkor M., Dahse H. M., Graefe U., Molecular structural studies of lichen substances with antimicrobial, antiproliferative, and cytotoxic effects from Parmelia subrudecta, Preparative biochemistry biotechnology, 40(4) (2010) 377-388.
  • [31] Ingolfsdottir K., Usnic acid, Phytochemistry, 61(7) (2002) 729-736.
  • [32] Takai M., Uehara Y., Beisler J. A., Usnic acid derivatives as potential antineoplastic agents, Journal of medicinal chemistry, 22(11) (1979) 1380-1384.
  • [33] Bézivin C., Tomasi S., Rouaud I., Delcros J. G., Boustie J., Cytotoxic activity of compounds from the lichen: Cladonia convoluta, Planta medica, 70(9) (2004) 874-877.
  • [34] Morris Kupchan S., Kopperman H. L., L-Usnic acid: tumor inhibitor isolated from lichens, Experientia, 31 (1975) 625-625.
  • [35] Cardarelli M., Serino G., Campanella L., Ercole P., De Cicco Nardone F., Alesiani O., Rossiello F., Antimitotic effects of usnic acid on different biological systems, Cellular and Molecular Life Sciences CMLS, 53 (1997) 667-672.
  • [36] Kumar S. P., Müller K., Lichen metabolites. 2. Antiproliferative and cytotoxic activity of gyrophoric, usnic, and diffractaic acid on human keratinocyte growth, Journal of natural products, 62(6) (1999) 821-823.
  • [37] Kumar S. P., Kekuda T. P., Vinayaka K. S., Sudharshan S. J., Anthelmintic and antioxidant efficacy of two macrolichens of Ramalinaceae, Pharmacognosy Journal, 1(4) (2009) 238-242.
  • [38] Mendili M., Bannour M., Araújo M. E. M., Seaward M. R., Khadhri A., Lichenochemical screening and antioxidant capacity of four Tunisian lichen species, Chemistry biodiversity, 18(2) (2021) e2000735.

Year 2024, Volume: 45 Issue: 3, 478 - 485, 30.09.2024

Banu Ceren Değirmenci , Mustafa Kocakaya , Selen İlgün , Gökçe Şeker Karatoprak , Zekiye Kocakaya , Ahmet Ceylan

https://doi.org/10.17776/csj.1424202

Abstract

Project Number

number 6601a-FBE/20-433

References

  • [1] Miao V., Coëffet-LeGal M. F., Brown D., Sinnemann S., Donaldson G., Davies J., Genetic approaches to harvesting lichen products, Trends in Biotechnology, 19(9) (2001) 349-355.
  • [2] Stanojković T., Investigations of lichen secondary metabolites with potential anticancer activity. Lichen secondary metabolites: bioactive properties and pharmaceutical potential, 9 (2019) 155-174.
  • [3] Shukla V., Joshi G. P., Rawat M. S. M., Lichens as a potential natural source of bioactive compounds: a review, Phytochemistry reviews, 9 (2010) 303-314.
  • [4] Illana-Esteban C. Lichens used in traditional medicine, Boletin de La Sociedad Micologica de Madrid, 36, (2012), 163-174.
  • [5] Crawford S. D., Lichens used in traditional medicine, Lichen secondary metabolites: bioactive properties and pharmaceutical potential, 9 (2019) 31-97.
  • [6] Richardson D. H. S., Lichens and man, Frontiers in mycology, 1 (1991) 187-210.
  • [7] Çobanoğlu G. ve Yavuz M., Tıp Tarihinde Likenlerle Tedavi, Yeni Tıp Tarihi Araştırmaları, 9, (2003) 37-90.
  • [8] Oksanen I., Ecological and biotechnological aspects of lichens, Applied microbiology and biotechnology, 73 (2006) 723-734.
  • [9] Paudel B., Bhattarai H. D., Lee J. S., Hong S. G., Shin H. W., Yim J. H., Antioxidant activity of polar lichens from King George Island (Antarctica), Polar Biology, 31 (2008) 605-608.
  • [10] Behera B. C., Verma N., Sonone A., Makhija U., Antioxidant and antibacterial activities of lichen Usnea ghattensis in vitro, Biotechnology letters, 27 (2005) 991-995.
  • [11] Gyawali R., Ibrahim S. A., Natural products as antimicrobial agents, Food control, 46 (2014) 412-429.
  • [12] Sharnoff S., A field guide to California lichens, Yale University Press, (2014).
  • [13] Kirk P. M., Cannon P. F., Minter D. W., & Stalpers J. A. Dictionary of the fungi Wallingford, UK: CABI, (2008), 335.
  • [14] Himmelreich U., Huneck S., Feige G. B., Lumbsch H. T., Squamaron, ein Naphthochinon aus der Flechte Squamarina cartilaginea/Squamarone, a Naphthoquinone from the Lichen Squamarina cartilaginea, Zeitschrift für Naturforschung B, 49(9) (1994) 1289-1291.
  • [15] Cansaran Duman D., Halıcı M. G., Antimicrobial activity of usnic acid on Squamarina lentigera lichen species, Turkish Bulletin of Hygiene and Experimental Biology, 69(3) (2012) 127-134.
  • [16] Sweidan A., Chollet-Krugler M., Sauvager A., Van De Weghe P., Chokr A., Bonnaure-Mallet M., Tomasi S., Bousarghin L., Antibacterial activities of natural lichen compounds against Streptococcus gordonii and Porphyromonas gingivalis, Fitoterapia, 121 (2017) 164-169.
  • [17] Reiter R. J., Acuña‐Castrovıejo D., Tan D. X., Burkhardt S., Free radical‐mediated molecular damage: mechanisms for the protective actions of melatonin in the central nervous system, Annals of the New York Academy of Sciences, 939(1) (2001) 200-215.
  • [18] Purvis O. W., Coppins B. J., Hawksworth D.L., James P. W., and Moore D. M., The Lichen Flora of Great Britain and Ireland. London: Natural History Museum Publications in association with the British Lichen Society (1992).
  • [19] Siddiq A., Anwar F., Manzoor M., Fatima M., Antioxidant activity of different solvent extracts of Moringa oleifera leaves under accelerated storage conditions of sunflower oil, Asian J. Plant Sci., 4 (2005) 630- 635.
  • [20] Karatoprak G. Ş., Göger F., Çelik İ., Budak Ü., Akkol E. K., Aschner M., Phytochemical profile, antioxidant, antiproliferative, and enzyme inhibition-docking analyses of Salvia ekimiana Celep & Doğan, South African Journal of Botany, 146 (2022) 36-47.
  • [21] Re R., Pellegrini N., Proteggente A., Pannala A., Yang M., Rice-Evans C., Antioxidant activity applying an improved ABTS radical cation decolorization assay, Free radical biology and medicine, 26 (9-10) (1999) 1231-1237.
  • [22] Zhishen J., Mengcheng T., Jianming W., The determination of flavonoid contents in mulberry and their scavenging effects on superoxide radicals, Food chemistry, 64(4) (1999) 555-559.
  • [23] Adinortey M. B., Ansah C., Weremfo A., Adinortey C. A., Adukpo G. E., Ameyaw E. O., Nyarko A. K., DNA damage protecting activity and antioxidant potential of Launaea taraxacifolia leaves extract, Journal of Natural Science, Biology, and Medicine, 9(1) (2018) 6.
  • [24] Gyamfi M. A., Yonamine M., Aniya Y., Free-radical scavenging action of medicinal herbs from Ghana: Thonningia sanguinea on experimentally-induced liver injuries, General Pharmacology: The Vascular System, 32(6) (1999) 661-667.
  • [25] Popovici V., Bucur L., Gîrd C. E., Popescu A., Matei E., Cozaru G. C., ... & Badea V. Phenolic Secondary Metabolites and Antiradical and Antibacterial Activities of Different Extracts of Usnea barbata (L.) Weber ex FH Wigg from Călimani Mountains, Romania, Pharmaceuticals, 15(7) (2022) 829.
  • [26] Kocovic A., Jeremic J., Bradic J., Sovrlic M., Tomovic J., Vasiljevic P., Manojlovic N., Phytochemical analysis, antioxidant, antimicrobial, and cytotoxic activity of different extracts of Xanthoparmelia stenophylla lichen from Stara Planina, Serbia, Plants, 11(13) (2022) 1624.
  • [27] Manojlovic N. T., Vasiljevic P. J., Maskovic P. Z., Juskovic M., Bogdanovic-Dusanovic G., Chemical composition, antioxidant, and antimicrobial activities of lichen Umbilicaria cylindrica (L.) Delise (Umbilicariaceae) Evidence-based complementary and alternative medicine, (2012).
  • [28] Campanella L., Delfini M., Ercole P., Iacoangeli A., & Risuleo G., Molecular characterization and action of usnic acid: a drug that inhibits proliferation of mouse polyomavirus in vitro and whose main target is RNA transcription, Biochimie, 84(4) (2002) 329-334.
  • [29] Fernández-Pastor I., González-Menéndez V., Martínez Andrade K., Serrano R., Mackenzie T. A., Benítez G., ... & Reyes F., Xerophytic Lichens from Gypsiferous Outcrops of Arid Areas of Andalusia as a Source of Anti-Phytopathogenic Depsides, Journal of Fungi, 9(9) (2023) 887.
  • [30] Ivanova V., Bačkor M., Dahse H. M., Graefe U., Molecular structural studies of lichen substances with antimicrobial, antiproliferative, and cytotoxic effects from Parmelia subrudecta, Preparative biochemistry biotechnology, 40(4) (2010) 377-388.
  • [31] Ingolfsdottir K., Usnic acid, Phytochemistry, 61(7) (2002) 729-736.
  • [32] Takai M., Uehara Y., Beisler J. A., Usnic acid derivatives as potential antineoplastic agents, Journal of medicinal chemistry, 22(11) (1979) 1380-1384.
  • [33] Bézivin C., Tomasi S., Rouaud I., Delcros J. G., Boustie J., Cytotoxic activity of compounds from the lichen: Cladonia convoluta, Planta medica, 70(9) (2004) 874-877.
  • [34] Morris Kupchan S., Kopperman H. L., L-Usnic acid: tumor inhibitor isolated from lichens, Experientia, 31 (1975) 625-625.
  • [35] Cardarelli M., Serino G., Campanella L., Ercole P., De Cicco Nardone F., Alesiani O., Rossiello F., Antimitotic effects of usnic acid on different biological systems, Cellular and Molecular Life Sciences CMLS, 53 (1997) 667-672.
  • [36] Kumar S. P., Müller K., Lichen metabolites. 2. Antiproliferative and cytotoxic activity of gyrophoric, usnic, and diffractaic acid on human keratinocyte growth, Journal of natural products, 62(6) (1999) 821-823.
  • [37] Kumar S. P., Kekuda T. P., Vinayaka K. S., Sudharshan S. J., Anthelmintic and antioxidant efficacy of two macrolichens of Ramalinaceae, Pharmacognosy Journal, 1(4) (2009) 238-242.
  • [38] Mendili M., Bannour M., Araújo M. E. M., Seaward M. R., Khadhri A., Lichenochemical screening and antioxidant capacity of four Tunisian lichen species, Chemistry biodiversity, 18(2) (2021) e2000735.
There are 38 citations in total.

Details

Primary Language English
Subjects Pharmacognosy
Journal Section Natural Sciences
Authors

Banu Ceren Değirmenci 0009-0000-6777-5415

Mustafa Kocakaya

Selen İlgün 0000-0002-8544-0683

Gökçe Şeker Karatoprak

Zekiye Kocakaya

Ahmet Ceylan

Project Number number 6601a-FBE/20-433
Publication Date September 30, 2024
Submission Date January 23, 2024
Acceptance Date August 19, 2024
Published in Issue Year 2024Volume: 45 Issue: 3

Cite

APA Değirmenci, B. C., Kocakaya, M., İlgün, S., Şeker Karatoprak, G., et al. (2024). Investigation of Biological Activity of Squamarina cartilaginea (With.) P. James Species Distributed in Türkiye. Cumhuriyet Science Journal, 45(3), 478-485. https://doi.org/10.17776/csj.1424202
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