소목 추출물의 항균활성과 Brazilin의 구조분석
Antibacterial Activities of Caesalpinia sappan L. Extract and Structural Analysis of Its Related Brazilin.
1
조회
0
다운로드
13
인용
0
참고문헌
키워드
초록
소목은 전통적으로 타박상, 염증 등의 질병치료를 위해 민간의학에서 오래 동안 사용되어 온 한약재이다. 소목의 심재로부터 항균효과를 조사하기 위하여 MeOH 추출에 의한hexane, CHCl3, EtOAc, n-BuOH, MeOH 및 H2O 분획을얻었다. 분획 시료 중 3.94%의 가장 높은 수율의 EtOAc 분획이 조사된 인체 병원성 세균에 대해 가장 강한 항균활성을 나타냈다. 또한 EtOAc 분획의 항균활성은 Gram (-) 균주 보다 Gram (+) 균주에 더 효과적이며, Gram (-) 균주에대해서는 세균에 따른 항균활성의 차이를 보였다. EtOAc 분획은 silica gel adsorption column chromatography 및Sephadex LH-20을 이용하여 분리하였으며 수득한 주요 성분은 재결정을 통하여 얻어진 단일물질을 HPLC를 이용하여 순도를 측정하였다. 300g의 C. sappan으로부터 3.94%의EtOAc분획을 얻었으며 EtOAc분획물은 분석한 결과 10 mg 에는 1.67 mg의 brazilin을 포함하였다. 분리된 활성물질은엷은 황색 결정의 단일 화합물로 MS에 의해 분자량이 285로 나타났으며, 1H-NMR, 13C-NMR에 의한 구조분석으로brazilin(C16H14O5)을 동정하였다. 이 같은 결과는 소목의MeOH 추출에 의한 EtOAc 분획에 존재하는 brazilin이 S. aureus와 같은 인체 병원성 Gram (+) 균주에 대한 생약치료제로 활용이 가능할 것을 시사한다.
Abstract
Caesalpinia sappan L. has long been commonly used in oriental folk medicines to treat diseases. To investigate the antibacterial effects from C. sappan L. heart wood, the MeOH soluble extract was successively fractionated by using hexane, CHCl3, EtOAc, BuOH, MeOH, and H2O. Among of these extracts, the EtOAc fraction which partitioned to 3.94% of the highest yields was to be the most active against all human pathogenic bacteria in this experiment. In addition, the antibacterial activities of the EtOAc fraction were more effective against Gram (+) bacteria compared to those against Gram (-) bacteria, which showed difference of the antibacterial activities against Gram (-) bacteria. To confirm the identity of the active substances, the EtOAc fraction was further separated by silica gel adsorption column, high performance liquid chromatography,and 98.48% purity of brazilin (1.67 mg)/ EtOAc (10 mg) fraction was obtained from 300 g of C. sappan L. heart wood. The isolated active substance was a single compound of yellow crystalline, and was identified as brazilin (C16H14O5) by MS, and 1H-NMR and 13C-NMR. These results suggest that the brazilin in the EtOAc fraction from MeOH extract of C. sappan L. has a potential as a natural therapeutic agent against human pathogenic Gram (+) bacteria such as Staphylococcus aureus.
참고문헌 (43)
- Badami, S., S, "Antioxidant activity of Caesalpinia sappan heart wood", Biol. Pharm. Bull., 26, pp.1534~1537 (2003)
- Baek, N. I, "Anticonvulsant compounds from the wood of Caesalpinia sappan", L. Arch. Pharmacol. Res., 23, pp.344~348 (2000)
- Beuchat, L. R, "Antimicrobials occurring naturally in foods", Food Technol., 43, pp.134~138 (1989)
- Chiang, L. C, "In vitro antiviral activities of Caesalpinia pulcherrima and its related flavonoids", J. Antimicrob. Chemother., 52, pp.194~198 (2003)
- 황의경, "Escherichia coli에 대한 한약재추출물의 항균활성", 대한수의학회지, 43(4), pp.625~631 (2003), 대한수의학회
- Choi, S. Y, "Brazilin modulates immune function mainly by augmenting T cell activity in halothane administered mice", Planta. Med., 63, pp.405~408 (1997)
- de Oliveira, L. F. C, "Vibrational spectroscopic study of brazilin and brazilein, the main constituents of brazilwood from Brazil", Vib. Spectrosc., 28, pp.243~249 (2002)
- Hu, C. M, "Induction of vasorelaxation through activation of nitric oxide synthase in endothelial cells by brazilin", Eur. J. Pharmacol., 468, pp.37~45 (2003)
- Huang,K.C., "The pharmacology of Chinese herbs", pp.266~ (1993), America CRC Press
- Hwang, G. S, "Effects of Brazilin on the phospholipase A2 activity and changes of intracellular free calcium concentration in rat platelets", Arch. Pharm. Res., 21, pp.774~778 (1998)
- Kang, J. M, "Identification of volatile essential oil, and flavor characterization and antimicrobial effect of fractions from Houttuynia cordata thunb", J. Korean Soc. Food Sci. Nutr., 26, pp.209~213 (1997)
- Kim, D. S, "NMR assignment of brazilein", Phytochemistry, 46, pp.177~178 (1997)
- Kim, K. J, "Inhibitory effects of Caesalpinia sappan on growth and invasion of methicillin-resistant Staphylococcus aureus", J. Ethnopharmacol., 91, pp.81~87 (2004)
- Kim, S. G, "Brazilin inhibits activities of protein kinase C and insulin receptor serine kinase in rat liver", Arch. Pharm. Res., 21, pp.140~146 (1998)
- Lee, B. W, "Screening of natural antimicrobial plant extract on food spoilage microorganism", Kor. J. Food Sci. Technol., 23, pp.200~201 (1991)
- Lee, K. T, "Brazilin as a new sunless tanning agent", J. Soc. Cosmet. Sci. Korea, 23, pp.82~85 (1997)
- 이성규, "가축질병 균주에 대한 소목의 항균활성", 한국미생물·생명공학회지, 31(3), pp.242~249 (2003), 한국미생물·생명공학회
- Lee, S. H, "Antimicrobial activity of Caesalpinia sappan L. extracts and its effect on preservation of ground meats", J. Kor. Soc. Food sci. Nutr., 29, pp.888~892 (2000)
- Lim, M. Y, "Antimicrobial activity of 5-hydroxy-1,4-naphtho- quinone isolated from Caesalpinia sappan toward intestinal bacteria", Food Chem., 100, pp.1254~1258 (2007)
- Mok, M. S, "Effects of brazilin on induction of immunological tolerance by sheep red blood cells in C57BL", 6 female mice, 1998, pp.21, 769~773
- Moon, C. K, "Brazilin protects cultured rat hepatocytes from BrCCl3-induced toxicity", Drug Chem. Toxicol., 15, pp.81~91 (1992)
- Namikoshi, M, "Homoisoflavonoids and related compounds. III. Phenolic constituents of Caesalpinia japonica SIEB", Et ZUCC. Chem. Pharm. Bull., 35, pp.3568~3575 (1987)
- Nguyen, M. T, "Xanthine oxidase inhibitors from the flowers of Chrysanthemum sinense", Planta. Med., 72, pp.46~51 (2006)
- Oh, S. R, "Anticomplementary activity of constituents from the heartwood of Caesalpinia sappan", Planta. Med., 64, pp.456~458 (1998)
- Otvos, L, "Antibacterial peptides isolated from insects", J. Pept. Sci., 6, pp.497~511 (2000)
- Parameshwar, S, "Oral antidiabetic activities of different extracts of Caesalpinia bonducella seed kernels", Pharm. Biol., 40, pp.590~595 (2002)
- Park, K. J, "Cytotoxic effects of Korean medicinal herbs determined with hepatocellular carcinoma cell lines", Pharm. Biol., 40, pp.189~195 (2002)
- Park, U. Y, "Screening of antimicrobial activity for medicinal herbs extracts", J. Kor. Soc. Food Nutr., 21, pp.91~96 (1992)
- Puchtler, H, "Application of current concepts to metal-hematein and -brazilein stains", Histochemistry, 85, pp.353~364 (1986)
- Rivero-Cruz, J. F, "Antimicrobial compounds isolated from Haematoxylon brasiletto", J. Ethnopharmacol., 119, pp.99~103 (2008)
- Rodriguez-Lopez V, "Spasmolytic activity of several extracts obtained from some Mexican medicinal plants", Fitoterapia., 74, pp.725~728 (2003)
- Safitri, R, "Antioxidant activity in vitro of two aromatic compounds from Caesalpinia sappan", L. Biofactors., 19, pp.71~77 (2003)
- Saitoh, T, "3- Benzylchroman derivatives related to brazilin from Sappan lignum", Chem. Pharm. Bull., 34, pp.2506~2511 (1986)
- Shin, D. H, "Antimicrobial effect of ethanol extracts from some medicinal herbs and their fractionates against food-borne bacteria", Kor. J. Food Sci. Technol., 29, pp.808~816 (1997)
- Shin,D.W, "Screening and using of antioxidative effect and antimicrobial activity from plant", Food Science industry, 36, pp.81~89 (2003)
- Sitaram, N, "Host-defense antimicrobial peptides: Importance of structure for activity", Curr. Pharm. Des., 8, pp.727~742 (2002)
- 손은정, "소목(Caesalpinia sappan)으로부터 분리한 caspase 유도 저해 물질", 한국식품과학회지, 35(4), pp.680~683 (2003), 한국식품과학회
- Ueda, J. Y, "Antiproliferative activity of Vietnamese medicinal plants", Biol. Pharm. Bull., 25, pp.753~760 (2002)
- Woldemichael, G. M, "Constituents of antibacterial extract of Caesalpinia paraguariensis Burk", Z. Naturforsch., 58, pp.70~75 (2003)
- Wu, M, "echanism of interaction of different classes of cationic antimicrobial peptides with planar bilayers and with the cytoplasmic membrane of Escherichia coli", Biochemistry, 38, pp.7235~7242 (1999)
- Xie, Y. W, "Vasorelaxing effects of Caesalpinia sappan Involvement of endogenous nitric oxide", Life Sci., 67, pp.1913~1918 (2000)
- You, E. J, "Effects of brazilin on the production of fructose-2,6-bisphosphate in rat hepatocytes", J. Ethnopharmacol., 102, pp.53~57 (2005)
- Zhao, H, "New homoisoflavan from Caesalpinia sap", Nat. Med., 62, pp.325~327 (2008)
