[논문]Antibacterial compounds against fish pathogenic bacteria from a combined extract of Angelica gigas and Artemisia iwayomogi and their quantitative analyses

Lim, Jae-Woong; Kim, Na Young; Seo, Jung-Soo; Jung, Sung-Hee; Kang, So Young

doi:10.47853/fas.2021.e31

Antibacterial compounds against fish pathogenic bacteria from a combined extract of Angelica gigas and Artemisia iwayomogi and their quantitative analyses 원문보기

Fisheries and aquatic sciences, v.24 no.10, 2021년, pp.319 - 329

Lim, Jae-Woong (Department of Aqualife Medicine, Chonnam National University) , Kim, Na Young (Pathology Research Division, National Institute of Fisheries Science) , Seo, Jung-Soo (Aquatic Disease Control Division, National Fishery Products Quality Management Service) , Jung, Sung-Hee (National Institute of Fisheries Science) , Kang, So Young (Department of Aqualife Medicine, Chonnam National University)

Abstract ▼ AI-Helper

In the search for antibiotic alternatives from safe and effective medicinal plants against fish pathogenic bacteria, we found that a combined extract (CE) of 1:1 (w/w) ratio of Angelica gigas Nakai roots and aerial parts of Artemisia iwayomogi Kitamura showed antibacterial activity against the fish pathogenic bacteria. By antibacterial activity-guided fractionations and isolations, five compounds were isolated and identified as decursinol angelate (1), decursin (2), xanthotoxin (3), demethylsuberosin (4), and 2,4-dihydroxy-6-methoxyacetophenone (5) through spectroscopic analyses, such as nuclear magnetic resonance (NMR) and mass spectrometry (MS). Among the compounds, 1 and 2 showed the highest antibacterial activities against Streptococcus iniae and Vibrio anguillarum, showing minimum inhibitory concentrations (MICs) of 62.5-250 ㎍/mL. Compounds 3, 4, and 5 were also found to be active, with MICs of 31.25-1,000 ㎍/mL for those strains. Furthermore, active compounds, 1 and 2 in CE were simultaneously quantified using high-performance liquid chromatography-tandem MS (HPLC-MS/MS). The average contents of 1 and 2 in CE was 3.68% and 6.14%, respectively. The established method showed reliable linearity (r2 > 0.99), good precision, accuracy, and specificity with intra- and inter-day variations of < 2 % and recoveries of 90.13%-108.57%. These results may be helpful for establishing the chemical profile of CE for its commercialization as an antibiotic alternative in aquaculture.

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표/그림 (8)

$Table 1. MICs of fractions and isolated compounds from CE against fish pathogenic bacteria$ 표 Table 1. MICs of fractions and isolated compounds from CE against fish pathogenic bacteria
그림 Fig. 1. Mass spectra and fragmentation patterns of the active compounds in CE. (A) ESI (positive) mass spectra of active compounds. (B) MS/MS fragmentation patterns of active compounds. CE, combined extract.
그림 Fig. 2. Chemical structures of the compounds isolated from Angelica gigas and Artemisia iwayomogi.
그림 Fig. 3. Representative MRM chromatograms of CE and its active compounds. (A) Chromatogram of blank solution. (B) Chromatogram of the active compounds in CE. (C) and (D) Chromatograms of standard compounds. CE, combined extract.
표 Table 2. Retention time, linear regression equation, correlation coefficient (r2), linear range, LOD, and LOQ of active compounds
표 Table 3. Intra- and inter-day precisions of active compounds
표 Table 4. Accuracy data of active compounds
표 Table 5. Contents of active compounds in CE

참고문헌 (46)

Ahn MJ, Lee MK, Kim YC, Sung SH. The simultaneous determination of coumarins in Angelica gigas root by high performance liquid chromatography-diode array detector coupled with electrospray ionization/mass spectrometry. J Pharm Biomed Anal. 2008;46:258-66.

상세보기
Bae EA, Han MJ, Kim NJ, Kim DH. Anti-Helicobacter pylori activity of herbal medicines. Biol Pharm Bull. 1998;21:990-2.

상세보기
Brown GD. Two new compounds from Artemisia annua. J Nat Prod. 1992;55:1756-60.

상세보기
Cha JD. Chemical composition and antibacterial activity against oral bacteria by the essential oil of Artemisia iwayomogi. J Bacteriol Virol. 2007;37:129-36.

원문보기 상세보기
Choi JS, Song BM, Park HJ. Identification of the component with anti-acetylcholinesterase activity from the essential oil of Artemisia iwayomogi. Korean J Plant Resour. 2017;30:17-21.
de Souza SM, Delle Monache F, Smania A Jr. Antibacterial activity of coumarins. Z Naturforsch C. 2005;60:693-700.
Durling NE, Catchpole OJ, Grey JB, Webby RF, Mitchell KA, Foo LY, et al. Extraction of phenolics and essential oil from dried sage (Salvia officinalis) using ethanol-water mixtures. Food Chem. 2007;101:1417-24.

상세보기
Heng MY, Tan SN, Yong JWH, Ong ES. Emerging green technologies for the chemical standardization of botanicals and herbal preparations. Trends Anal Chem. 2013;50:1-10.
Hsieh PC, Mau JL, Huang SH. Antimicrobial effect of various combinations of plant extracts. Food Microbiol. 2001;18:35-43.

상세보기
Ivarsen E, Frette XC, Christensen KB, Christensen LP, Engberg RM, Grevsen K, et al. Bioassay-guided chromatographic isolation and identification of antibacterial compounds from Artemisia annua L. that inhibit Clostridium perfringens growth. J AOAC Int. 2014;97:1282-90.

상세보기
Jeon EJ, Lee NS, Seo JS, Jung SH, Kim MS, Kang SY, et al. Study of anti-pathogenic herbal materials for the eco-friendly drugs in aquaculture. J Fish Mar Sci Edu. 2020;32:980-7.
Joo SS, Park D, Shin S, Jeon JH, Kim TK, Choi YJ, et al. Anti-allergic effects and mechanisms of action of the ethanolic extract of Angelica gigas in dinitrofluorobenzene-induced inflammation models. Environ Toxicol Pharmacol. 2010;30:127-33.
Jung HS, Cha MK, Kwon YJ, So JS. Differential inhibitory effect of Artemisia extract between Staphylococcus aureus and vaginal Lactobacillus spp. Korean Soc Biotechnol Bioeng J. 2005;20:228-32.
Kang SY, Kang JY, Kim SY, Kim DH, Oh MJ. Antimicrobial activities of alkyl gallates alone and in combination with antibiotics against the fish pathogenic bacteria Edwardsiella tarda and Vibrio anguillarum. Korean J Fish Aquat Sci. 2008;41:188-92.
Kang SY, Lee KY, Sung SH, Kim YC. Four new neuroprotective dihydropyranocoumarins from Angelica gigas. J Nat Prod. 2005;68:56-9.

상세보기
Kemper N. Veterinary antibiotics in the aquatic and terrestrial environment. Ecol Indic. 2008;8:1-13.
Kim KM, Jung JY, Hwang SW, Kim MJ, Kang JS. Isolation and purification of decursin and decursinol angelate in Angelica gigas Nakai. J Korean Soc Food Sci Nutr. 2009;38:653-6.
Kim SH, Choi CH, Kim SY, Eun JS, Shin TY. Anti-allergic effects of Artemisia iwayomogi on mast cell-mediated allergy model. Exp Biol Med. 2005;230:82-8.
Kim SJ, Ko SM, Choi EJ, Ham SH, Kwon YD, Lee YB, et al. Simultaneous determination of decursin, decursinol angelate, nodakenin, and decursinol of Angelica gigas Nakai in human plasma by UHPLC-MS/MS: application to pharmacokinetic study. Molecules. 2018;23:1019.

상세보기
Koch N, Islam NF, Sonowal S, Prasad R, Sarma H. Environmental antibiotics and resistance genes as emerging contaminants: methods of detection and bioremediation. Curr Res Microb Sci. 2021;2:100027.
Langfield RD, Scarano FJ, Heitzman ME, Kondo M, Hammond GB, Neto CC. Use of a modified microplate bioassay method to investigate antibacterial activity in the Peruvian medicinal plant Peperomia galioides. J Ethnopharmacol. 2004;94:279-81.

상세보기
Lee JH, Chae HJ, Kim DH, Lee SH, Park SY, Kang YG. HPLC analysis and extraction methods of Decursin and Decursinol angelate in Angelica gigas roots. Korean J Pharmacogn. 2003a;34:201-205.
Lee KR, Zee OP, Kwak JH, Kim YS, Park HK, Koo KA, et al. The polysaccharide fraction of Artemisia species(I). Korean J Pharmacogn. 1993;24:289-95.
Lee S, Lee YS, Jung SH, Shin KH, Kim BK, Kang SS. Anti-tumor activities of decursinol angelate and decursin from Angelica gigas. Arch Pharm Res. 2003b;26:727-30.

원문보기 상세보기
Lee S, Shin DS, Kim JS, Oh KB, Kang SS. Antibacterial coumarins from Angelica gigas roots. Arch Pharm Res. 2003c;26:449-52.

원문보기 상세보기
Lim JW, Shin SM, Jung SJ, Lee MK, Kang SY. Optimization of antibacterial extract from lacquer tree (Rhus verniciflua Stokes) using response surface methodology and its efficacy in controlling edwardsiellosis of olive flounder (Paralichthys olivaceus). Aquaculture. 2019;502:40-7.
Masuda T, Takasugi M, Anetai M. Psoralen and other linear furanocoumarins as phytoalexins in Glehnia littoralis. Phytochemistry. 1998;47:13-6.

상세보기
Mosihuzzaman M, Choudhary MI. Protocols on safety, efficacy, standardization, and documentation of herbal medicine. Pure Appl Chem. 2008;80:2195-230.
Muller M, Byres M, Jaspars M, Kumarasamy Y, Middleton M, Nahar L, et al. 2D NMR spectroscopic analyses of archangelicin from the seeds of Angelica archangelica. Acta Pharm. 2004;54:277-85.
Nikam PH, Kareparamban J, Jadhav A, Kadam V. Future trends in standardization of herbal drugs. J Appl Pharm Sci. 2012;2:38-44.
Nishiyama N, Wang YL, Saito H. Beneficial effects of S-113m, a novel herbal prescription, on learning impairment model in mice. Biol Pharm Bull. 1995;18:1498-1503.

상세보기
Ong ES. Extraction methods and chemical standardization of botanicals and herbal preparations. J Chromatogr B. 2004;812:23-33.

상세보기
Park KY, Lee AY, Ban JH, Park JK, Lee EH. Effects of herbal medicine on breastfeeding - analysis of marker substances in Saenghwa-tang by HPLC and LC/MS/MS. J Korean Obstet Gynecol. 2013;26:48-65.
Park SI, Heo SH, Lee J, Shin MS. Extraction of active compounds from Angelica gigas using supercritical carbon dioxide and its physiological activity. J Converg Inf Technol. 2021;11:206-12.
Reverter M, Tapissier-Bontemps N, Sarter S, Sasal P, Caruso D. Moving towards more sustainable aquaculture practices: a meta-analysis on the potential of plant-enriched diets to improve fish growth, immunity and disease resistance. Rev Aquac. 2021;13:537-55.

상세보기
Rhim JY, Moon YS, Jung SH, Lee KY, Lyu SY, Shim CS, et al. Antimicrobial activities of combined extract of Aloe vera with propolis against oral pathogens. J Korean Soc Food Sci Nutr. 2002;31:899-904.
Seo JS, Kim NY, Jeong SH, Kim MS, Hwang JY, Kang SY, et al. Anti-bacterial composition for comprising extract of mixed herbal medication. Korea patent 10-1709169. 2017 Feb 16.
Seo KS, Jeong HJ, Yun KW. Antimicrobial activity and chemical components of two plants, Artemisia capillaris and Artemisia iwayomogi, used as Korean herbal Injin. J Ecol Environ. 2010;33:141-7.
Shin S, Jeon JH, Park D, Jang JY, Joo SS, Hwang BY, et al. Anti-inflammatory effects of an ethanol extract of Angelica gigas in a carrageenan-air pouch inflammation model. Exp Anim. 2009;58:431-6.

상세보기
Sin SM, Jeong WM, Kil YS, Lee DY, Kim SG, Goo YM. Anti-inflammatory and anti-bacterial activities of Artemisia iwayomogi Kitamura extract fractions. J Life Sci. 2020;30:40-4.
Taechowisan T, Chanaphat S, Ruensamran W, Phutdhawong WS. Antibacterial activity of decursin from Streptomyces sp. GMT-8; an endophyte in Zingiber officinale Rosc. J Appl Pharm Sci. 2013;3:74-8.
Taleghani A, Emami SA, Tayarani-Najaran Z. Artemisia: a promising plant for the treatment of cancer. Bioorg Med Chem. 2020;28:115180.

상세보기
Yoo JS, Ahn EM, Song MC, Bang MH, Kim DH, Han MW, et al. Quantitative analysis of coumarins from Angelica gigas using 1 H-NMR. Food Sci Biotechnol. 2008;17:573-7.

원문보기 상세보기
Yoon MY, Kim YS, Ryu SY, Choi GJ, Choi YH, Jang KS, et al. In vitro and in vivo antifungal activities of decursin and decursinol angelate isolated from Angelica gigas against Magnaporthe oryzae, the causal agent of rice blast. Pestic Biochem Physiol. 2011;101:118-24.

상세보기
Yu HH, Kim YH, Kil BS, Kim KJ, Jeong SI, You YO. Chemical composition and antibacterial activity of essential oil of Artemisia iwayomogi. Planta Med. 2003;69:1159-62.

상세보기
Zhao Y, Li HX, Kim YH, Cho CW, Hwang SY, Oh HA, et al. Standardization of extract mixture of Chaenomeles sinensis and Phyllostachys bambusoides for anti-obesity by HPLC-UV. Arch Pharm Res. 2017;40:1156-65.

상세보기

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