Antibacterial compounds against fish pathogenic bacteria from a combined extract of Angelica gigas and Artemisia iwayomogi and their quantitative analyses
0
조회
0
다운로드
0
인용
0
참고문헌
키워드
초록
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 μg/mL. Compounds 3, 4, and 5 were also found to be active, with MICs of 31.25–1,000 μg/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.
Abstract
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 μg/mL. Compounds 3, 4, and 5 were also found to be active, with MICs of 31.25–1,000 μg/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.
참고문헌 (46)
- Ahn MJ, "The simultaneous determination of coumarins in Angelica gigas root by high performance liquid chromatography–diode array detector coupled with electrospray ionization", mass spectrometry, 2008, pp.46, 258~266
- Bae EA, "Anti-Helicobacter pylori activity of herbal medicines", Biol Pharm Bull, 21, pp.990~992 (1998)
- Brown GD, "Two new compounds from Artemisia annua", J Nat Prod, 55, pp.1756~1760 (1992)
- Jeong-Dan Cha, "Chemical Composition and Antibacterial Activity Against Oral Bacteria by the Essential Oil of Artemisia iwayomogi", Journal of Bacteriology and Virology, 37(3), pp.129~136 (2007), 대한미생물학회
- 최재수, "더위지기 정유로부터 아세틸콜린에스테라제 억제활성 성분의 동정", 한국자원식물학회지, 30(1), pp.17~21 (2017), 한국자원식물학회[DOI]
- de Souza SM, "Antibacterial activity of coumarins", Z Naturforsch C, 60, pp.693~700 (2005)
- Durling NE, "Extraction of phenolics and essential oil from dried sage(Salvia officinalis)using ethanol–water mixtures", Food Chem, 101, pp.1417~1424 (2007)
- Heng MY, "Emerging green technologies for the chemical standardization of botanicals and herbal preparations", Trends Anal Chem, 50, pp.1~10 (2013)
- Hsieh PC, "Antimicrobial effect of various combinations of plant extracts", Food Microbiol, 18, pp.35~43 (2001)
- Ivarsen E, "Bioassay-guided chromatographic isolation and identification of antibacterial compounds from Artemisia annua L. that inhibit Clostridium perfringens growth", J AOAC Int, 97, pp.1282~1290 (2014)
- 전은지, "수산양식에서 친환경성 약제개발을 위한 항병성 생약소재의 검토", 수산해양교육연구, 32(4), pp.980~987 (2020), 한국수산해양교육학회
- Joo SS, "Anti-allergic effects and mechanisms of action of the ethanolic extract of Angelica gigas in dinitrofluorobenzene-induced inflammation models", Environ Toxicol Pharmacol, 30, pp.127~133 (2010)
- 소재성, "쑥 추출물의 포도상구균과 질 유산균에 대한 선택적 저해효과", KSBB Journal, 20(3), pp.228~232 (2005), 한국생물공학회
- 강소영, "알킬갈레이트 유도체의 어병세균 Edwardsiella tarda와 Vibrio anguilarum에 대한 항균활성 및 항생제와의 병용효과", 한국수산과학회지, 41(3), pp.188~192 (2008), 한국수산과학회
- Kang SY, "Four new neuroprotective dihydropyranocoumarins from Angelica gigas", J Nat Prod, 68, pp.56~59 (2005)
- Kemper N, "Veterinary antibiotics in the aquatic and terrestrial environment", Ecol Indic, 8, pp.1~13 (2008)
- 김강민, "참당귀(Angelica gigas Nakai) 중 Decursin 및 Decursinol Angelate의 분리 및 정제", 한국식품영양과학회지, 38(5), pp.653~656 (2009), 한국식품영양과학회
- Kim SH, "Anti-allergic effects of Artemisia iwayomogi on mast cell-mediated allergy model", Exp Biol Med, 230, pp.82~88 (2005)
- Kim SJ, "Simultaneous determination of decursin, decursinol angelate, nodakenin, and decursinol of Angelica gigas Nakai in human plasma by UHPLC-MS", MS : application to pharmacokinetic study, 2018, pp.23, 1019~
- Koch N, "Environmental antibiotics and resistance genes as emerging contaminants : methods of detection and bioremediation", Curr Res Microb Sci, 2, pp.100027~ (2021)
- Langfield RD, "Use of a modified microplate bioassay method to investigate antibacterial activity in the Peruvian medicinal plant Peperomia galioides", J Ethnopharmacol, 94, pp.279~281 (2004)
- YoungGooKang, "당귀(Angelica gigas) 중 Decursin 및 Decursinol Angelate 추출 방법과 HPLC 분석", 생약학회지, 34(3), pp.201~205 (2003), 한국생약학회
- Lee KR, "The polysaccharide fraction of Artemisia species(I)", Korean J Pharmacogn, 24, pp.289~295 (1993)
- Lee S, "Anti-tumor activities of decursinol angelate and decursin from Angelica gigas", Arch Pharm Res, 26, pp.727~730 (2003)
- 이상현, "Antibacterial Coumarins from Angelica gigas Roots", Archives of Pharmacal Research, 26(6), pp.449~452 (2003), 대한약학회
- Lim JW, "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, 502, pp.40~47 (2019)
- Masuda T, "Psoralen and other linear furanocoumarins as phytoalexins in Glehnia littoralis", Phytochemistry, 47, pp.13~16 (1998)
- Mosihuzzaman M, "Protocols on safety, efficacy, standardization, and documentation of herbal medicine", Pure Appl Chem, 80, pp.2195~2230 (2008)
- Muller M, "2D NMR spectroscopic analyses of archangelicin from the seeds of Angelica archangelica", Acta Pharm, 54, pp.277~285 (2004)
- Nikam PH, "Future trends in standardization of herbal drugs", J Appl Pharm Sci, 2, pp.38~44 (2012)
- Nishiyama N, "Beneficial effects of S-113m, a novel herbal prescription, on learning impairment model in mice", Biol Pharm Bull, 18, pp.1498~1503 (1995)
- Ong ES, "Extraction methods and chemical standardization of botanicals and herbal preparations", J Chromatogr B, 812, pp.23~33 (2004)
- 박가영, "산모의 한약 복용이 모유에 미치는 영향- HPLC와 LC", MS, 대한한방부인과학회지, pp.2013, 26(4)[DOI]
- 박수인, "초임계 이산화탄소를 이용한 참당귀 유효 성분의 추출 및 생리활성 효능", 융합정보논문지, 11(6), pp.206~212 (2021), 중소기업융합학회[DOI]
- Reverter M, "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, 13, pp.537~555 (2021)
- 임지영, "알로에 베라 및 프로폴리스 혼합 추출물의 구강내 병원균에 대한 항균활성", 한국식품영양과학회지, 31(5), pp.899~904 (2002), 한국식품영양과학회
- Seo JS, "Anti-bacterial composition for comprising extract of mixed herbal medication", Korea patent 10-1709169, ~ (2017)
- 서경순, "Antimicrobial activity and chemical components of two plants, Artemisia capillaris and Artemisia iwayomogi, used as Korean herbal Injin", Journal of Ecology and Environment, 33(2), pp.141~147 (2010), 한국생태학회
- Shin S, "Anti-inflammatory effects of an ethanol extract of Angelica gigas in a carrageenan-air pouch inflammation model", Exp Anim, 58, pp.431~436 (2009)
- 신승미, "한인진 분획물의 항염증, 항균 효과", 생명과학회지, 30(1), pp.40~44 (2020), 한국생명과학회[DOI]
- Taechowisan T, "Antibacterial activity of decursin from Streptomyces sp. GMT-8; an endophyte in Zingiber officinale Rosc", J Appl Pharm Sci, 3, pp.74~78 (2013)
- Taleghani A, "Artemisia : a promising plant for the treatment of cancer", Bioorg Med Chem, 28, pp.115180~ (2020)
- Jong-Su Yoo, "Quantitative Analysis of Coumarins from Angelica gigas Using 1HNMR", Food Science and Biotechnology, 17(3), pp.573~577 (2008), 한국식품과학회
- Yoon MY, "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, 101, pp.118~124 (2011)
- Yu HH, "Chemical composition and antibacterial activity of essential oil of Artemisia iwayomogi", Planta Med, 69, pp.1159~1162 (2003)
- Yan Zhao, "Standardization of extract mixture of Chaenomeles sinensis and Phyllostachys bambusoides for anti-obesity by HPLC–UV", Archives of Pharmacal Research, 40(10), pp.1156~1165 (2017), 대한약학회