홍조류 모로우붉은실(Polysiphonia morrowii)의 추출물과 이로부터 분리된 브로모페놀계 화합물의 in vitro 항균·항스쿠티카충 활성 및 구조-활성 상관성
In vitro Anti-bacterial and Anti-scuticociliate Activities of Extract and Bromophenols of the Marine Red Alga Polysiphonia morrowii with Structure-activity Relationships
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초록
Scuticociliates are regarded as serious pathogens in marine aquaculture worldwide. In Korea, they cause mass-mor- talities in fish such as the commercially important olive flounder Paralichthys olivaceus . In particular, mixed infec- tions of scuticociliates with pathogenic bacteria have been commonly reported. During efforts to identify natural marine-algae derived products that possess anti-bacterial and anti-scuticociliate properties, we found that an 80% methanolic extract of the red alga Polysiphonia morrowii Harvey exhibits both anti-scuticociliate activity against Miamiensis avidus , which is a major causative agent of scuticociliatosis, and anti-bacterial activities against fish pathogenic bacteria. Activity-guided fractionation and isolation of the 80% methanolic extract of P. morrowii yielded three bromophenols, which were identified as 3-bromo-4,5-dihydroxybenzyl methyl ether (1), 3-bromo-4,5-dihy- droxybenzaldehyde (2) and urceolatol (3) based on spectroscopic analyses. 3-bromo-4,5-dihydroxybenzyl methyl ether (1) showed the highest anti-bacterial and anti-scuticociliate activities, with a minimal inhibitory concentration (MIC) of 62.5 µg/mL (against Vibrio anguillarum ) and minimal lethal concentration (MLC) of 62.5 ppm (in seawa- ter). Investigations of the anti-bacterial and anti-scuticociliate activities of seventeen bromophenol derivatives, in- cluding the three isolated natural bromophenols, showed that the existence of an electron donating group or atom with a non-covalent electron pair at C4 of the 2-bromophenol structure may be important in anti-scuticociliate activity. These findings suggest that the extract and bromophenol derivatives of P. morrowii may provide useful alternatives in aquaculture anti-scuticociliate therapies.
Abstract
Scuticociliates are regarded as serious pathogens in marine aquaculture worldwide. In Korea, they cause mass-mor- talities in fish such as the commercially important olive flounder Paralichthys olivaceus . In particular, mixed infec- tions of scuticociliates with pathogenic bacteria have been commonly reported. During efforts to identify natural marine-algae derived products that possess anti-bacterial and anti-scuticociliate properties, we found that an 80% methanolic extract of the red alga Polysiphonia morrowii Harvey exhibits both anti-scuticociliate activity against Miamiensis avidus , which is a major causative agent of scuticociliatosis, and anti-bacterial activities against fish pathogenic bacteria. Activity-guided fractionation and isolation of the 80% methanolic extract of P. morrowii yielded three bromophenols, which were identified as 3-bromo-4,5-dihydroxybenzyl methyl ether (1), 3-bromo-4,5-dihy- droxybenzaldehyde (2) and urceolatol (3) based on spectroscopic analyses. 3-bromo-4,5-dihydroxybenzyl methyl ether (1) showed the highest anti-bacterial and anti-scuticociliate activities, with a minimal inhibitory concentration (MIC) of 62.5 µg/mL (against Vibrio anguillarum ) and minimal lethal concentration (MLC) of 62.5 ppm (in seawa- ter). Investigations of the anti-bacterial and anti-scuticociliate activities of seventeen bromophenol derivatives, in- cluding the three isolated natural bromophenols, showed that the existence of an electron donating group or atom with a non-covalent electron pair at C4 of the 2-bromophenol structure may be important in anti-scuticociliate activity. These findings suggest that the extract and bromophenol derivatives of P. morrowii may provide useful alternatives in aquaculture anti-scuticociliate therapies.
참고문헌 (23)
- 배민지, "온도가 스쿠티카충 Miamiensis avidus의 증식과 넙치에 감염시 폐사에 미치는 영향", 한국어병학회지, 22(2), pp.97~105 (2009), 한국어병학회
- Han L, "Isolation and pharmacological activities of bromophenols from Rhodomela confervoides", Chin J Ocean Limn, 23, pp.226~229 (2005)
- Harikrishnan R, "Scuticociliatosis and its recent prophylactic measures in aquaculture with special reference to South Korea Taxonomy, diversity and diagnosis of scuticociliatosis: Part I Control strategies of scuticociliatosis: Part II", Fish Shellfish Immunol, 29, pp.15~31 (2010)
- Iglesias R, "Antiprotozoals effective in vitro against the scuticociliate fish pathogen Philasterides dicentrarchi", Dis Aqua Org, 49, pp.191~197 (2002)
- Jee BY, "Morphology and biology of parasite responsible for scuticociliatosis of cultured olive flounder Paralichthys olivaceus", Dis Aquat Org, 47, pp.49~55 (2001)
- 진창남, "제주도지역 넙치양식장의 스쿠티카증 발생동향", 한국어병학회지, 20(1), pp.93~98 (2007), 한국어병학회
- Jung SJ, "Miamiensis avidus (Ciliophora: Scuticociliatida)causes systemic infection of olive flounder Paralichthys olivaceus and is a senior synonym of Philasterides dicentrarchi", Dis Aquat Org, 73, pp.227~234 (2007)
- 강소영, "알킬갈레이트 유도체의 어병세균 Edwardsiella tarda와 Vibrio anguilarum에 대한 항균활성 및 항생제와의 병용효과", 한국수산과학회지, 41(3), pp.188~192 (2008), 한국수산과학회
- 강소영, "한국산 해조류의 어류병원성세균에 대한 항균활성", 한국어병학회지, 18(2), pp.147~156 (2005), 한국어병학회
- Kim SM, "Occurrence of Scuticociliatosis in olive flounder Paralichthys olivaceus by Philasterides dicentrarchi", Dis Aquat Org, 62, pp.233~238 (2004)
- Kim SM, "Pseudocohnilemdus persalinus (Ciliophora: Scuticociliatida) is an additional species causing Scuticociliatosis in olive flounder Paralichthys olivaceus", Dis Aquat Org, 62, pp.239~244 (2004)
- Su-Yeun Kim, "In Vitro Antiviral Activity of Red Alga, Polysiphonia morrowii Extract and Its Bromophenols Against Fish Pathogenic Infectious Hematopoietic Necrosis Virus and Infectious Pancreatic Necrosis Virus", The Journal of Microbiology, 49(1), pp.102~106 (2011), 한국미생물학회
- Kurata K, "Feeding-deterrent bromophenols from Odonthalia corymbifera", Phytochemistry, 45, pp.485~487 (1997)
- Kurihara H, "Inhibitory potencies of bromophenols from Rhodomelaceae algae against α-glucosidase activity", Fish Sci, 65, pp.300~303 (1999)
- Lamas J, "Resveratrol promotes an inhibitory effect on the turbot scuticociliate parasite Philasterides dicentrarchi by mechanisms related to cellular detoxification", Vet Parasitol, 161, pp.307~315 (2009)
- Lau SS, "Identification of 2-bromohydroquinone as a metabolite of bromobenzene and o-bromophenol: implications for bromobenzene-induced nephrotoxicity", J Pharmacol Exp Ther, 230, pp.360~366 (1984)
- Li K, "Bromophenols from the marine red alga Polysiphonia urceolata with DPPH radical scavenging activity", J Nat Prod, 71, pp.28~30 (2008)
- Liu QW, "Urceolatol, a tetracyclic bromobenzaldehyde dimer from Polysiphonia urceolata", J Asian Nat Prod Res, 8, pp.379~383 (2006)
- Report on carcinogen 12th Edition, "National Toxicology Program", 195~204 (2011)
- Shoeib, NA, "In-vitro cytotoxic activities of the major bromophenols of the red alga Polysiphonia lanosa and some novel synthetic isomers", J Nat Prod, 67, pp.1445~1449 (2004)
- Wall ME, "Plant antimutagenic agents, 7. Structure and antimutagenic properties of cymobarbatol and 4-isocymobarbatol, new cymopols from green alga(Cymopolia barbata)", J Nat Prod, 52, pp.1092~1099 (1989)
- Wiemer DF, "Vidalols A and B, new anti-inflammatory bromophenols from the Caribbean marine red alga Vidalia obtusaloba", Experientia, 47, pp.851~853 (1991)
- Xu N, "Antibacterial bromophenols from the marine red alga Rhodomela confervoides", Phytochemistry, 62, pp.1221~1224 (2003)