Abstract
The present study describes the bioactive secondary metabolites of Artemisia iwayomogy and Chrysanthemum morifolium, a traditional medicinal plant widely distributed in Korea, through activity-monitored fractionation and isolation method. The aerial parts of plants were extracted with 80% ethyl alcohol, and an aqueous suspension of the extracts was partitioned successively with n-hexane, chloroform, ethylacetate, and n-butanol, leaving a residual water-soluble fraction. Secondary metabolites, compounds 1–12 were isolated from biologically active solvent-soluble fractions, and chemical structures were identified by high resolution mass spectroscopy and nuclear magnetic resonance spectroscopic analyses. All compounds were subjected to bioassay to evaluate their antioxidant and antimicrobial activities, as judged by scavenging stable 1,1-diphenyl-2-picrylhydrazyl free radicals and disk diffusion test with a minor modification of Institute of Clinical Laboratory Standards, respectively. Kaempferol (4), quercimeritrin (8), luteolin (10), and chlorogenic acid (12) were found to be antioxidants, and the concentrations at which resulted in 50% inhibition (IC50) were 105.16±0.09, 101.72±0.76, 91.96±0.06, and 85.31±0.14 μM, respectively, and their activities compared favorably with those observed with the standards, ascorbic acid and BHA, which had IC50 values of 125.48±0.02 and 115.40±0.01 μM, respectively. Leucodin (5) was isolated from A. Iwayomogi for the first time as moderate antioxidant and antimicrobial naturals.
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References
Almeida AA, Farah A, Silva DA, Nunan EA, and Glória MB (2006). Antibacterial activity of coffee extracts and selected coffee chemical compounds against enterobacteria. J Agric Food Chem 54, 8738–8743.
Byun Y-H, Shim Y, Lim S, Choi S-H, Park N-H, Moon S-R, Koo In-H, Lee K-U, Lee M-Y, Hong H-J, Chung H-S, Lee Y-H, and Shin S-W (2006) Development of natural drugs against antibiotics-resistant bacteria from Artemisia and Chrysanthemum species in Korea and study on its active mechanism (1). Duksung Bull Pharm Sci 17, 13–21.
Cheng N, Abraham L, Masakuni T, Isao H, and Hajime T (2008) Antioxidant flavonoid glycosides from the leaves of Ficus pumila L. Food Chem 109, 415–420.
Cho EJ, Yokozawa T, Rhyu DY, Kim SC, Shibahara N, and Park JC (2003). Study on the inhibitory effects of Korean medicinal plants and their main compounds on the 1,1-diphenyl-2-picrylhydrazyl radical. Phytomedicine 10, 544–551.
Chung EY, Byun YH, Shin EJ, Chung HS, Lee YH, and Shin S (2009). Antibacterial effects of Vulgarone B from Artemisia iwayomogi alone and in combination with Oxacillin. Arch Pharm Res 32, 1711–1719.
Chung HS, Chang LC, Lee SK, Shamon LA, van Breeman RG, Mehta RG, Farnsworth NR, Pezzuto JM, and Kinghorn AD (1999) Flavonoid constituents of Chorizanthe diffusa with potential cancer chemopreventive activity. J Agric Food Chem 47, 36–41.
Chung HS and Shin JC (2007) Characterization of antioxidant alkaloids and phenolic acids from anthocyanin-pigmented rice (Oryza sativa cv. Heugjinjubyeo). Food Chem 104, 1670–1677.
Chung HS and Woo WS (1994) Dentalactone, A sesquiterpene from Ixeris dentate. Phytochem 35, 1583–1584.
Clinical and Laboratory Standards Institute. 2006. M100-S16, Performance standards for antimicrobial susceptibility testing; 16th informational supplement. Clinical and Laboratory Standards Institute, Wayne, PA, USA.
Eggimann P, Garbino J, and Pittet D (2003) Epidemiology of Candida species infections in critically ill nonimmunosuppressed patients. The LANCET Infectious Diseases 3, 685–702.
Farah D, Tran DX, Masaaki Y, and Shinkichi (2008) Chemical composition and antioxidant, antibacterial and antifungal activities of the essential oils from Bidens pilosa Linn. var. Radiata. Food Control 19, 346–352.
Glasl S, Mucaji P, Werner I, Presser A, and Jurenitsch J (2002) Sesquiterpenes and flavonoid aglycones from Hungarian taxon of the Achillea millefolium group. Z Naturforsch C 57, 976–982.
Han S, Sung KH, Yim D, Lee S, Lee CK, Ha NJ, and Kim K (2002) The effect of linarin on LPS-induced cytokine production and nitric oxide inhibition in murine macrophages cell line RAW264.7. Arch Pharm Res 25, 170–177.
Heilmann J, Merfort I, and Weiss M (1995) Radical scavenger activity of different 3′,4′-dihyroxyflavonols and 1,5-dicafeoylquinic acid studied by inhibition of chemiluminescence. Planta Med 61, 435–438.
Hwang JS, Ji HJ, Koo KA, Lee NH, Yeo HK, Cheong SW, Park JH, Oh GS, Yoon CS, and Youn HJ (2005) AIP1, a water-soluble fraction from Artemisia iwayomogi, suppresses thymocyte apoptosis in vitro and downregulates the expression of Fas gene. Biol Pharm Bull 28, 921–924.
Hyun JW and Chung HS (2006) In Globalisation of Herbal Health, Govil JN and Singh VK (eds.), Recent Progress in Medicinal Plants 12, 193–202, Studium Press, Texas, TX, USA.
Kusmenoglu S, Baser KHC, and Ozek T (1995) Constituents of the essential oils from the hulls of Pistacia vera L. J Essential Oil Res 7, 44–442.
Lee JA, Sung HN, Jeon CH, Gill BC, Oh GS, Youn HJ, and Park JH (2008) AIP1, a carbohydrate fraction from Artemisia iwayomogi, modulates the functional differentiation of bone marrow-derived dendritic cells. Int Immunopharmacol 8, 534–541.
Lopes-Lutz D, Alviano DS, Alviano CS, and Kolodzeiejczyk PP (2008) Screening of chemical composition, antimicrobial and antioxidant activities of Artemisia essential oils. Phytochem 69, 1732–1738.
Shin TY, Park JS, and Kim SH (2006) Artemisia iwayomogi inhibits immediate-type allergic reaction and inflammatory cytokine secretion. Immunopharmacol Immunotoxicol 28, 421–430.
Singh RP, Agrawal P, Yim D, Agarwal C, and Agarwal R (2005) Acacetin inhibits cell growth and cell cycle progression, and induces apoptosis in human prostate cancer cells: structure-activity relationship with linarin and linarin acetate. Carcinogenesis 26, 845–854.
Taskova R, Mitova M, Mikhova B, and Duddeck H (2003) Bioactive phenolics from Carthamus lanatus L. Z Naturforsch 58, 704–707.
Tshikalange TE, Meyer JJ, and Hussein AA (2005) Antimicrobial activity, toxicity and the isolation of a bioactive compound from plants used to treat sexually transmitted diseases. J Ethnopharmacol 96, 515–519.
Zheng ZP, Cheng KW, Chao J, Wu J, and Wang M (2008) Tyrosinase inhibitors from paper mulberry (Broussonetia papyrifera). Food Chem 106, 529–535.
Zou Y, Lu Y, and Wei D (2004) Antioxidant activity of a flavonoid rich extract of Hypericum perforatum L. in vitro. J Agric Food Chem 52, 5032–5039.
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Shin, S., Lee, Y., Moon, S.R. et al. Identification of secondary metabolites with antioxidant and antimicrobial activities from Artemisia iwayomogi and Chrysanthemum zawadskii . J. Korean Soc. Appl. Biol. Chem. 53, 716–723 (2010). https://doi.org/10.3839/jksabc.2010.108
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DOI: https://doi.org/10.3839/jksabc.2010.108