Determination of the antioxidant activity and antibacterial effect of the α-lipoic acid-NHS molecule in fisheries products

Samet Kalkan

Araştırma Makalesi

Alfa-lipoik asit-NHS molekülünün antioksidan aktivitesinin ve su ürünlerindeki antibakteriyel etkisinin belirlenmesi

Yıl 2025, Cilt: 42 Sayı: 4, 323 - 330

Öz

Alfa-lipoik asit, metabolik yolaklarda önemli roller üstlenir ve güçlü bir antioksidan savunma sağlar. Bu çalışmada, α-lipoik asidin N-hidroksisüksinimid ester türevinin (α-lipoik asit–NHS) antioksidan etkinliği ve sucul ortamlardan izole edilen Gram-negatif ve Gram-pozitif bakteri suşlarında inhibitör aktivitesi değerlendirilmiştir. Antioksidan performans, DPPH (2,2-diphenyl-1-picrylhydrazyl) radikal süpürme ve CUPRAC (Cu2+ iyon indirgeme) testleri ile analiz edilmiştir. Ayrıca, farklı α-lipoik asit–NHS konsantrasyonlarında, 8-OHdG ELISA yöntemi ile reaktif oksijen türleri (ROS) düzeyleri ölçülerek bileşiğin oksidatif stresi baskılama potansiyeli incelenmiştir. Antibakteriyel aktivite, dört referans patojen (Staphylococcus aureus, Aeromonas hydrophila, Salmonella enterica, Escherichia coli) ve dört çevresel izolat (Bacillus cereus, B. toyonensis, Oceanisphaera sediminis, Pseudomonas putida) üzerinde mikrodilüsyon yöntemiyle test edilmiştir. Sonuçlar, α-lipoik asit–NHS’nin hem DPPH hem de CUPRAC testlerinde ihmal edilebilir düzeyde antioksidan aktivite gösterdiğini ortaya koymuştur. Buna karşılık, antibakteriyel etki açısından bakıldığında, bazı bakteri suşlarında yüksek konsantrasyonlarda (5–10 mM) tam büyüme inhibisyonu gözlenmiştir. Artan α-lipoik asit–NHS dozunda ROS düzeylerinde hafif bir azalma görülmüşsede, bu etki kimyasal antioksidan test sonuçlarıyla paralellik göstermemiştir; yani gözlenen azalmanın doğrudan antioksidan etkiden kaynaklanmadığı düşünülmektedir. Sonuç olarak, α-lipoik asit–NHS, etkili bir doğrudan serbest radikal süpürücü olarak işlev görmez; ancak dolaylı antioksidan etkiler ve orta düzeyde antibakteriyel aktivite gösterebilir. Tek başına tedavi edici bir ajan olmaktan ziyade, antioksidan sistemlerde ve antibakteriyel tedavilerde destekleyici bir bileşik olarak potansiyele sahiptir.

Anahtar Kelimeler

Antibakteriyel etki , akuakültür , balık patojeni , minimum inhibitör konsantrasyon , oksidatif stres , reaktif oksijen türleri

Proje Numarası

FHD-2024-1686

Kaynakça

Akbulut, C., Kaymak, G., Esmer, H.E., Yön, N.D., & Kayhan, F.E. (2014). Oxidative stress mechanisms induced by heavy metals and pesticides in fish. Ege Journal of Fisheries and Aquatic Sciences, 31(3), 155-160. https://doi.org/10.12714/egejfas.2014.31.3.07
Alfadda, A.A., & Sallam, R.M. (2012). Reactive oxygen species in health and disease. Biomed Research International, 2012(1), 936486. https://doi.org/10.1155/2012/936486
Apak, R., Güçlü, K., Özyürek, M., & Karademir, S.E. (2004). Novel total antioxidant capacity index for dietary polyphenols and vitamins C and E, using their cupric ion reducing capability in the presence of neocuproine: CUPRAC method. Journal of Agricultural and Food Chemistry, 52(26), 7970-7981. https://doi.org/10.1021/jf048741x
Apak, R., Güçlü, K., Özyürek, M., Bektaşoğlu, B., & Bener, M. (2008). Cupric ion reducing antioxiant capacity assay for food antioxidants: Vitamins, polyphenolics, and flavonoids in food extracts. Methods in Molecular Biology, 477, 163–193. https://doi.org/10.1007/978-1-60327-517-0_14
Atila, N., Kaya, Z., Atila, A., Halici, Z., Bayir, Y., Sirin, B., Kahramanlar, A., Cadirci, E., Ozkaraca., M., Keles, O., & Ozmen, S. (2022). Are Antibiotics Sufficient for Treating Bacterial Rhinosinusitis? The Influence of Alpha-Lipoic Acid, a Potent Antioxidant, As an Additional Treatment in Bacterial Rhinosinusitis. B-ENT, 18(4). https://doi.org/10.5152/b-ent.2022.21476
Blois, M.S. (1958). Antioxidant determinations by the use of a stable free radical. Nature, 181(4617), 1199 1200. https://doi.org/10.1038/1811199a0
Brand-Williams, W., Cuvelier, M.E., & Berset, C. (1995). Use of a free radical method to evaluate antioxidant activity. Food Science and Technology, 28(1), 25–30. https://doi.org/10.1016/S0023-6438(95)80008-5
Charlton, N.C., Mastyugin, M., Török, B., & Török, M. (2023). Structural features of small molecule antioxidants and strategic modifications to improve potential bioactivity. Molecules, 28(3), 1057. https://doi.org/ 10.3390/molecules28031057
Clinical and Laboratory Standards Institute (2024, September 25). Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically (12th ed.; CLSI standard M07). Wayne, PA: CLSI. https://clsi.org/shop/standards/m07/
Cronan, J.E. (2020). Progress in the enzymology of the mitochondrial diseases of lipoic acid requiring enzymes. Frontiers in Genetics, 11, 510. https://doi.org/10.3389/fgene.2020.00510
Dean, R.T., Fu, S., Stocker, R., & Davies, M.J. (1997). Biochemistry and pathology of radical-mediated protein oxidation. Biochemical Journal, 324(1), 1-18. https://doi.org/10.1042/bj3240001
Diment, D., Musl, O., Balakshin, M., & Rigo, D. (2024). Guidelines for evaluating the antioxidant activity of lignin via the 2, 2-diphenyl-1-picrylhydrazyl (DPPH) assay. ChemSusChem, 18(10), e202402383. https://doi.org/10.1002/cssc.202402383
Dunn, O.J., & Clark, V.A. (2009). Basic statistics: a primer for the biomedical sciences. John Wiley & Sons. 4th ed. Hoboken, NJ: Wiley.
European Committee on Antimicrobial Susceptibility Testing (EUCAST). (2024, September 25). Broth microdilution—EUCAST reading guide (Version 5.0). https://www.eucast.org/ast_of_bacteria/mic_determination?utm.
Giri, A., Aquib, M., Choudhury, A., Kannaujiya, V.K., Lim, J.L., Gu, Z., Lenardon, M., & Boyer, C. (2025). Lipoic Acid Based Redox‐Responsive Degradable Antimicrobial Polymers. Macromolecular Rapid Communications, 46(17), e00224. https://doi.org/10.1002/marc.202500224
Gorąca, A., Huk-Kolega, H., Piechota, A., Kleniewska, P., Ciejka, E., & Skibska, B. (2011). Lipoic acid–biological activity and therapeutic potential. Pharmacological Reports, 63(4), 849-858. https://doi.org/10.1016/S1734-1140(11)70600-4
Guimaraes, A., Abrunhosa, L., Pastrana, L.M., & Cerqueira, M.A. (2018). Edible films and coatings as carriers of living microorganisms: A new strategy towards biopreservation and healthier foods. Comprehensive Reviews in Food Science and Food Safety, 17(3), 594-614. https://doi.org/10.1111/1541-4337.12345
Gülçin, I. (2008). Measurement of antioxidant ability of melatonin and serotonin by the DMPD and CUPRAC methods as trolox equivalent. Journal of Enzyme Inhibition and Medicinal Chemistry, 23(6), 871-876. https://doi.org/10.1080/14756360701626223
Hajtuch, J., Santos-Martinez, M.J., Wojcik, M., Tomczyk, E., Jaskiewicz, M., Kamysz, W., & Inkielewicz-Stepniak, I. (2022). Lipoic acid-coated silver nanoparticles: Biosafety potential on the vascular microenvironment and antibacterial properties. Frontiers in Pharmacology, 12, 733743. https://doi.org/10.3389/fphar.2021.733743
Han, D., Handelman, G., Marcocci, L., Sen, C.K., Roy, S., Kobuchi, H., Tritschler, H., Flohé, L., & Packer, L. (1997). Lipoic acid increases de novo synthesis of cellular glutathione by improving cystine utilization. Biofactors, 6(3), 321-338. https://doi.org/10.1002/biof.5520060303
Hermanson, G.T. (2013). Bioconjugate techniques. (third ed.), Academic Press, Boston https://doi.org/10.1016/C2009-0-64240-9
Howarth, M., Liu, W., Puthenveetil, S., Zheng, Y., Marshall, L.F., Schmidt, M. M., & Ting, A. Y. (2008). Monovalent, reduced-size quantum dots for imaging receptors on living cells. Nature Methods, 5(5), 397-399. https://doi.org/10.1038/nmeth.1206
Jia, Z., Zhu, H., Vitto, M.J., Misra, B.R., Li, Y., & Misra, H.P. (2009). Alpha-lipoic acid potently inhibits peroxynitrite-mediated DNA strand breakage and hydroxyl radical formation: implications for the neuroprotective effects of alpha-lipoic acid. Molecular and Cellular Biochemistry, 323(1), 131-138. https://doi.org/10.1007/s11010-008-9971-6
Jomova, K., Raptova, R., Alomar, S.Y., Alwasel, S.H., Nepovimova, E., Kuca, K., & Valko, M. (2023). Reactive oxygen species, toxicity, oxidative stress, and antioxidants: Chronic diseases and aging. Archives of Toxicology, 97(10), 2499-2574. https://doi.org/10.1007/s00204-023-03562-9
Kalkan, S. (2022). Multimodal analysis of south-eastern Black Sea sediment bacterial population diversity. Marine Pollution Bulletin, 183, 114063. https://doi.org/10.1016/j.marpolbul.2022.114063
Kilgore, H.R., Olsson, C.R., D’Angelo, K.A., Movassaghi, M., & Raines, R.T. (2020). n→ π* Interactions modulate the disulfide reduction potential of epidithiodiketopiperazines. Journal of the American Chemical Society, 142(35), 15107-15115. https://doi.org/10.1021/jacs.0c06477
Koniev, O., & Wagner, A. (2015). Developments and recent advancements in the field of endogenous amino acid selective bond forming reactions for bioconjugation. Chemical Society Reviews, 44(15), 5495-5551. https://doi.org/ 10.1039/c5cs00048c
Kowald, A., & Kirkwood, T.B. (2018). Resolving the enigma of the clonal expansion of mtDNA deletions. Genes, 9(3), 126. https://doi.org/10.3390/genes9030126
Luo, Q., Han, Q., Chen, L., Fan, X., Wang, Y., Fei, Z., Zhang, H., Wang, Y. (2020). Redox response, antibacterial and drug package capacities of chitosan-α-lipoic acid conjugates. International Journal of Biological Macromolecules, 154, 1166 1174. https://doi.org/10.1016/j.ijbiomac.2019.10.271
Na, M.H., Seo, E.Y., & Kim, W.K. (2009). Effects of α-lipoic acid on cell proliferation and apoptosis in MDA-MB-231 human breast cells. Nutrition Research and Practice, 3(4), 265 271. https://doi.org/10.4162/nrp.2009.3.4.265
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Determination of the antioxidant activity and antibacterial effect of the α-lipoic acid-NHS molecule in fisheries products

Yıl 2025, Cilt: 42 Sayı: 4, 323 - 330

Samet Kalkan

Öz

Alpha-lipoic acid plays significant roles in metabolic pathways and provides substantial antioxidant defense. In this study, the N-hydroxysuccinimide ester derivative (α-lipoic acid–NHS) was examined for antioxidant performance and inhibitory effects on Gram-negative and Gram-positive bacterial strains isolated from aquatic environments. Antioxidant performance was evaluated using DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging and CUPRAC (cupric ion reducing) assays. Additionally, The compound’s ability to mitigate oxidative stress was evaluated by quantifying reactive oxygen species (ROS) levels with the 8-OHdG ELISA method at different α-lipoic acid–NHS concentrations. Antibacterial activity was tested against four reference pathogens (Staphylococcus aureus, Aeromonas hydrophila, Salmonella enterica, Escherichia coli) and four environmental isolates (Bacillus cereus, B. toyonensis, Oceanisphaera sediminis, Pseudomonas putida) using the microdilution method. The results showed that α-lipoic acid–NHS exhibited negligible antioxidant activity in both DPPH and CUPRAC assays. In terms of antibacterial effects, however, complete inhibition of growth was observed in some bacterial strains at higher concentrations (5–10 mM). While ROS levels decreased modestly with increasing α-lipoic acid–NHS, this effect did not correlate with chemical antioxidant test results, suggesting the reduction was not due to direct antioxidant action. In conclusion, α-lipoic acid–NHS does not function as an effective direct radical scavenger but may exert indirect antioxidant effects and moderate antibacterial activity. It may have potential as a supportive compound in antioxidant systems and antibacterial therapies rather than as a standalone therapeutic agent.

Anahtar Kelimeler

Antibacterial effect , aquaculture , fish pathogen , minimum inhibitory concentration , oxidative stress , reactive oxygen species

Etik Beyan

This research did not involve any studies with human participants or animals performed by the author. Therefore, no ethical approval was required.

Destekleyen Kurum

Recep Tayyip Erdoğan University Scientific Research Projects Coordination Unit (BAP), Project No: FHD-2024-1686

Proje Numarası

FHD-2024-1686

Kaynakça

Akbulut, C., Kaymak, G., Esmer, H.E., Yön, N.D., & Kayhan, F.E. (2014). Oxidative stress mechanisms induced by heavy metals and pesticides in fish. Ege Journal of Fisheries and Aquatic Sciences, 31(3), 155-160. https://doi.org/10.12714/egejfas.2014.31.3.07
Alfadda, A.A., & Sallam, R.M. (2012). Reactive oxygen species in health and disease. Biomed Research International, 2012(1), 936486. https://doi.org/10.1155/2012/936486
Apak, R., Güçlü, K., Özyürek, M., & Karademir, S.E. (2004). Novel total antioxidant capacity index for dietary polyphenols and vitamins C and E, using their cupric ion reducing capability in the presence of neocuproine: CUPRAC method. Journal of Agricultural and Food Chemistry, 52(26), 7970-7981. https://doi.org/10.1021/jf048741x
Apak, R., Güçlü, K., Özyürek, M., Bektaşoğlu, B., & Bener, M. (2008). Cupric ion reducing antioxiant capacity assay for food antioxidants: Vitamins, polyphenolics, and flavonoids in food extracts. Methods in Molecular Biology, 477, 163–193. https://doi.org/10.1007/978-1-60327-517-0_14
Atila, N., Kaya, Z., Atila, A., Halici, Z., Bayir, Y., Sirin, B., Kahramanlar, A., Cadirci, E., Ozkaraca., M., Keles, O., & Ozmen, S. (2022). Are Antibiotics Sufficient for Treating Bacterial Rhinosinusitis? The Influence of Alpha-Lipoic Acid, a Potent Antioxidant, As an Additional Treatment in Bacterial Rhinosinusitis. B-ENT, 18(4). https://doi.org/10.5152/b-ent.2022.21476
Blois, M.S. (1958). Antioxidant determinations by the use of a stable free radical. Nature, 181(4617), 1199 1200. https://doi.org/10.1038/1811199a0
Brand-Williams, W., Cuvelier, M.E., & Berset, C. (1995). Use of a free radical method to evaluate antioxidant activity. Food Science and Technology, 28(1), 25–30. https://doi.org/10.1016/S0023-6438(95)80008-5
Charlton, N.C., Mastyugin, M., Török, B., & Török, M. (2023). Structural features of small molecule antioxidants and strategic modifications to improve potential bioactivity. Molecules, 28(3), 1057. https://doi.org/ 10.3390/molecules28031057
Clinical and Laboratory Standards Institute (2024, September 25). Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically (12th ed.; CLSI standard M07). Wayne, PA: CLSI. https://clsi.org/shop/standards/m07/
Cronan, J.E. (2020). Progress in the enzymology of the mitochondrial diseases of lipoic acid requiring enzymes. Frontiers in Genetics, 11, 510. https://doi.org/10.3389/fgene.2020.00510
Dean, R.T., Fu, S., Stocker, R., & Davies, M.J. (1997). Biochemistry and pathology of radical-mediated protein oxidation. Biochemical Journal, 324(1), 1-18. https://doi.org/10.1042/bj3240001
Diment, D., Musl, O., Balakshin, M., & Rigo, D. (2024). Guidelines for evaluating the antioxidant activity of lignin via the 2, 2-diphenyl-1-picrylhydrazyl (DPPH) assay. ChemSusChem, 18(10), e202402383. https://doi.org/10.1002/cssc.202402383
Dunn, O.J., & Clark, V.A. (2009). Basic statistics: a primer for the biomedical sciences. John Wiley & Sons. 4th ed. Hoboken, NJ: Wiley.
European Committee on Antimicrobial Susceptibility Testing (EUCAST). (2024, September 25). Broth microdilution—EUCAST reading guide (Version 5.0). https://www.eucast.org/ast_of_bacteria/mic_determination?utm.
Giri, A., Aquib, M., Choudhury, A., Kannaujiya, V.K., Lim, J.L., Gu, Z., Lenardon, M., & Boyer, C. (2025). Lipoic Acid Based Redox‐Responsive Degradable Antimicrobial Polymers. Macromolecular Rapid Communications, 46(17), e00224. https://doi.org/10.1002/marc.202500224
Gorąca, A., Huk-Kolega, H., Piechota, A., Kleniewska, P., Ciejka, E., & Skibska, B. (2011). Lipoic acid–biological activity and therapeutic potential. Pharmacological Reports, 63(4), 849-858. https://doi.org/10.1016/S1734-1140(11)70600-4
Guimaraes, A., Abrunhosa, L., Pastrana, L.M., & Cerqueira, M.A. (2018). Edible films and coatings as carriers of living microorganisms: A new strategy towards biopreservation and healthier foods. Comprehensive Reviews in Food Science and Food Safety, 17(3), 594-614. https://doi.org/10.1111/1541-4337.12345
Gülçin, I. (2008). Measurement of antioxidant ability of melatonin and serotonin by the DMPD and CUPRAC methods as trolox equivalent. Journal of Enzyme Inhibition and Medicinal Chemistry, 23(6), 871-876. https://doi.org/10.1080/14756360701626223
Hajtuch, J., Santos-Martinez, M.J., Wojcik, M., Tomczyk, E., Jaskiewicz, M., Kamysz, W., & Inkielewicz-Stepniak, I. (2022). Lipoic acid-coated silver nanoparticles: Biosafety potential on the vascular microenvironment and antibacterial properties. Frontiers in Pharmacology, 12, 733743. https://doi.org/10.3389/fphar.2021.733743
Han, D., Handelman, G., Marcocci, L., Sen, C.K., Roy, S., Kobuchi, H., Tritschler, H., Flohé, L., & Packer, L. (1997). Lipoic acid increases de novo synthesis of cellular glutathione by improving cystine utilization. Biofactors, 6(3), 321-338. https://doi.org/10.1002/biof.5520060303
Hermanson, G.T. (2013). Bioconjugate techniques. (third ed.), Academic Press, Boston https://doi.org/10.1016/C2009-0-64240-9
Howarth, M., Liu, W., Puthenveetil, S., Zheng, Y., Marshall, L.F., Schmidt, M. M., & Ting, A. Y. (2008). Monovalent, reduced-size quantum dots for imaging receptors on living cells. Nature Methods, 5(5), 397-399. https://doi.org/10.1038/nmeth.1206
Jia, Z., Zhu, H., Vitto, M.J., Misra, B.R., Li, Y., & Misra, H.P. (2009). Alpha-lipoic acid potently inhibits peroxynitrite-mediated DNA strand breakage and hydroxyl radical formation: implications for the neuroprotective effects of alpha-lipoic acid. Molecular and Cellular Biochemistry, 323(1), 131-138. https://doi.org/10.1007/s11010-008-9971-6
Jomova, K., Raptova, R., Alomar, S.Y., Alwasel, S.H., Nepovimova, E., Kuca, K., & Valko, M. (2023). Reactive oxygen species, toxicity, oxidative stress, and antioxidants: Chronic diseases and aging. Archives of Toxicology, 97(10), 2499-2574. https://doi.org/10.1007/s00204-023-03562-9
Kalkan, S. (2022). Multimodal analysis of south-eastern Black Sea sediment bacterial population diversity. Marine Pollution Bulletin, 183, 114063. https://doi.org/10.1016/j.marpolbul.2022.114063
Kilgore, H.R., Olsson, C.R., D’Angelo, K.A., Movassaghi, M., & Raines, R.T. (2020). n→ π* Interactions modulate the disulfide reduction potential of epidithiodiketopiperazines. Journal of the American Chemical Society, 142(35), 15107-15115. https://doi.org/10.1021/jacs.0c06477
Koniev, O., & Wagner, A. (2015). Developments and recent advancements in the field of endogenous amino acid selective bond forming reactions for bioconjugation. Chemical Society Reviews, 44(15), 5495-5551. https://doi.org/ 10.1039/c5cs00048c
Kowald, A., & Kirkwood, T.B. (2018). Resolving the enigma of the clonal expansion of mtDNA deletions. Genes, 9(3), 126. https://doi.org/10.3390/genes9030126
Luo, Q., Han, Q., Chen, L., Fan, X., Wang, Y., Fei, Z., Zhang, H., Wang, Y. (2020). Redox response, antibacterial and drug package capacities of chitosan-α-lipoic acid conjugates. International Journal of Biological Macromolecules, 154, 1166 1174. https://doi.org/10.1016/j.ijbiomac.2019.10.271
Na, M.H., Seo, E.Y., & Kim, W.K. (2009). Effects of α-lipoic acid on cell proliferation and apoptosis in MDA-MB-231 human breast cells. Nutrition Research and Practice, 3(4), 265 271. https://doi.org/10.4162/nrp.2009.3.4.265
Nikaido, H. (2003). Molecular basis of bacterial outer membrane permeability revisited. Microbiology and Molecular Biology Reviews, 67(4), 593-656. https://doi.org/10.1128/mmbr.67.4.593-656.2003
Packer, L., Witt, E.H., & Tritschler, H.J. (1995). Alpha-lipoic acid as a biological antioxidant. Free Radical Biology and Medicine, 19(2), 227-250. https://doi.org/10.1016/0891-5849(95)00017-R
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Toplam 48 adet kaynakça vardır.

Ayrıntılar

Birincil Dil	İngilizce
Konular	Biyokimya ve Hücre Biyolojisi (Diğer), Gıda Mühendisliği, Balık Biyolojisi, Balık Zararlıları ve Hastalıkları
Bölüm	Araştırma Makalesi
Yazarlar	Samet Kalkan 0000-0002-5110-5609
Proje Numarası	FHD-2024-1686
Erken Görünüm Tarihi	1 Aralık 2025
Yayımlanma Tarihi	3 Aralık 2025
Gönderilme Tarihi	12 Temmuz 2025
Kabul Tarihi	25 Eylül 2025
Yayımlandığı Sayı	Yıl 2025 Cilt: 42 Sayı: 4

Kaynak Göster

APA	Kalkan, S. (2025). Determination of the antioxidant activity and antibacterial effect of the α-lipoic acid-NHS molecule in fisheries products. Ege Journal of Fisheries and Aquatic Sciences, 42(4), 323-330.

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