Isolation of Guaian-6,12-olides from Artemisia princeps and Their Antioxidant Activity
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Background: Korean mugwort, Artemisia princeps, a plant that has been widely used in diet and traditional medicine throughout East Asia. Methods and Results: Two novel guaian-6,12-olides (1 and 2) and two known compounds (3 and 4) were isolated from Korean mugwort, their chemical structures were established by extensive spec- troscopic analysis and comparison with those of known compounds. The antioxidant capacity of the isolated compounds was evaluated by measuring intracellular reactive oxygen species (ROS) genera- tion in HT-1080 cells and the extent of oxidative damage to genomic DNA purified from HT-1080 cells. Compounds 1 and 3 exhibited outstanding intracellular ROS scavenging activity at a concentra- tion of 10 µM compared to the untreated blank. Particularly, 3 exhibited an exceptional ROS scaveng- ing activity of approximately 67% at a concentration of 1 µM after 2 h. Additionally, all compounds significantly inhibited DNA oxidation induced by hydroxyl radicals at a concentration greater than 1 µM. Among them, 4 showed the most effective protection against DNA damage. Conclusions: Further studies are expected to provide more insight on development of guaian-6,12- olides as potential antioxidants and mechanism by which these types of guaianolides act as antioxidants.
Abstract
Background: Korean mugwort, Artemisia princeps, a plant that has been widely used in diet and traditional medicine throughout East Asia. Methods and Results: Two novel guaian-6,12-olides (1 and 2) and two known compounds (3 and 4) were isolated from Korean mugwort, their chemical structures were established by extensive spec- troscopic analysis and comparison with those of known compounds. The antioxidant capacity of the isolated compounds was evaluated by measuring intracellular reactive oxygen species (ROS) genera- tion in HT-1080 cells and the extent of oxidative damage to genomic DNA purified from HT-1080 cells. Compounds 1 and 3 exhibited outstanding intracellular ROS scavenging activity at a concentra- tion of 10 µM compared to the untreated blank. Particularly, 3 exhibited an exceptional ROS scaveng- ing activity of approximately 67% at a concentration of 1 µM after 2 h. Additionally, all compounds significantly inhibited DNA oxidation induced by hydroxyl radicals at a concentration greater than 1 µM. Among them, 4 showed the most effective protection against DNA damage. Conclusions: Further studies are expected to provide more insight on development of guaian-6,12- olides as potential antioxidants and mechanism by which these types of guaianolides act as antioxidants.
참고문헌 (32)
- Asem SD, "A new guaianolidesesquiterpene lactone from Curcuma leucorrhiza Roxb", Natural Product Research, 28, pp.477~482 (2014)
- Bang MH, "Development of biologically active compounds from edible plant sources-XIX. Isolation of inhibitory compound on LDL-oxidation from the aerial parts of Sajabalssuk(Artemisia princeps Pampanini, Sajabalssuk)", Journal of the Korean Society for Applied Biological Chemistry, 50, pp.224~227 (2007)
- Chen XY, "Sesquiterpene lactones from Artemisia vulgaris L. as potential NO inhibitors in LPS-induced RAW264.7 macrophage cells", Fronters in Chemistry, 10, pp.948714~ (2022)
- Dhyani P, "Sesquiterpenoid lactones as potential anti-cancer agents : an update on molecular mechanisms and recent studies", Cancer Cell International, 22, pp.305~ (2022)
- Drew DP, "Guaianolides in Apiaceae : perspectives on pharmacology and biosynthesis", Phytochemistry Reviews, 8, pp.581~599 (2009)
- Fraga BM, "Natural sesquiterpenoids", Natural Product Reports, 24, pp.1350~1381 (2007)
- Gligorovski S, "Environmental implications of hydroxyl radicals(?OH)", Chemical Reviews, 115, pp.13051~13092 (2015)
- Juan CA, "The chemistry of reactive oxygen species(ROS)revisited : outlining their role in biological macromolecules(DNA, lipids and proteins)and induced pathologies", International Journal of Molecular Sciences, 22, pp.4642~ (2021)
- Karadeniz F, "Sesquiterpene lactones : A review of biological activities", Journal of Life Science, 31, pp.430~441 (2021)
- Klaunig JE, "Oxidative stress in carcinogenesis", Current Opinion in Toxicology, 7, pp.116~121 (2018)
- Koreeda M, "Studies on sesquiterpene lactones. XIII. : Chemical constituents of Artemisia montana(NAKAI)PAMP", Yakugaku Zasshi, 108, pp.434~436 (1988)
- Li D, "Inhibitors of nitric oxide production from Artemisia princeps", Natural Product Sciences, 16, pp.143~147 (2010)
- Ma GH, "Advance in biological activities of natural guaiane-type sesquiterpenes", Medicinal Chemistry Research, 28, pp.1339~1358 (2019)
- Mehrabani M, "Evaluation of cytotoxic and antioxidant effect of guaianolid sesquiterpenes from Ferula hindukushensis", ChemistrySelect, 8, pp.e202300895~ (2023)
- Milne L, "Effects of glutathione and chelating agents on copper-mediated DNA oxidation : pro-oxidant and antioxidant properties of glutathione", Archives of Biochemistry and Biophysics, 304, pp.102~109 (1993)
- Mosmann T, "Rapid colorimetric assay for cellular growth and survival : application to proliferation and cytotoxicity assays", Journal of Immunological Methods, 65, pp.55~63 (1983)
- Moujir L, "Applications of sesquiterpene lactones : A review of some potential success cases", Applied Sciences, 10, pp.3001~ (2020)
- Moyo P, "Bioassay-guided isolation and identification of gametocytocidal compounds from Artemisia afra(Asteraceae)", Malaria Journal, 18, pp.65~ (2019)
- Nagaki M, "Guaianolides from Artemisia montana", Phytochemistry, 28, pp.2731~2733 (1989)
- Nawrot J, "Antifungal activity of the sesquiterpene lactones from Psephellus bellus", Plants, 10, pp.1180~ (2021)
- Okimotoa Y, "A novel fluorescent probe diphenyl-1-pyrenylphosphine to follow lipid peroxidation in cell membranes", FEBS Letters, 474, pp.137~140 (2000)
- Rehman NU, "Lyciumaside and lyciumate : A new diacylglycoside and sesquiterpene lactone from Lycium shawii", Helvetica Chimica Acta, 99, pp.632~635 (2016)
- Reiniers MJ, "Preparation and practical applications of 2’, 7’-dichlorodihydrofluorescein in redox assays", Analytical Chemistry, 89, pp.3853~3857 (2017)
- Salazar-Gómez A, "The potential role of sesquiterpene lactones isolated from medicinal plants in the treatment of the metabolic syndrome — A review", South African Journal of Botany, 135, pp.240~251 (2020)
- Serafini M, "The role of antioxidants in disease prevention", Medicine, 34, pp.533~535 (2006)
- Simonsen HT, "Natural Products: Phytochemistry, botany and metabolism of alkaloids, phenolics and terpenes", pp.3069~3097 (2013), Springer Berlin Heidelberg
- Srinivas US, "ROS and the DNA damage response in cancer", Redox Biology, 25, pp.101084~ (2019)
- Suleman M, "Antioxidants, its role in preventing free radicals and infectious diseases in human body", Pure and Applied Biology, 8, pp.380~388 (2019)
- Vajs V, "Guaianolides from Centaureanicolai : Antifungal activity", Phytochemistry, 52, pp.383~386 (1999)
- Wedge DE, "Fungicidal activity of natural and synthetic sesquiterpene lactone analogs", Phytochemistry, 53, pp.747~757 (2000)
- Wiseman H, "Damage to DNA by reactive oxygen and nitrogen species : role in inflammatory disease and progression to cancer", Biochemical Journal, 313, pp.17~29 (1996)
- Yu D, "Improved detection of reactive oxygen species by DCFH-DA : New insight into self-amplification of fluorescence signal by light irradiation", Sensors and Actuators B : Chemical, 339, pp.129878~ (2021)
