The Korean Journal of Pesticide Science (농약과학회지)

The Korean Society of Pesticide Science (한국농약과학회)
권호 표지
DOI QR코드

DOI QR Code

Isolation and identification of antifungal compounds from Spatholobus suberectus Dunn

계혈등(Spatholobus suberectus Dunn)으로부터 항균활성 물질의 분리 및 구조결정

  • Hwang, Joo-Tae (Department of Bioenvironmental Chemistry, College of Agricultural and Life Science, Chungnam National University) ;
  • Park, Young-Sik (Department of Bioenvironmental Chemistry, College of Agricultural and Life Science, Chungnam National University) ;
  • Kim, Young-Shin (Department of Bioenvironmental Chemistry, College of Agricultural and Life Science, Chungnam National University) ;
  • Kim, Jin-Cheol (Green Chemistry Division, Korea Research Institute of Chemical Technology) ;
  • Lim, Chi-Hwan (Department of Bioenvironmental Chemistry, College of Agricultural and Life Science, Chungnam National University)
  • 황주태 (충남대학교 농업생명과학대학 생물환경화학과) ;
  • 박영식 (충남대학교 농업생명과학대학 생물환경화학과) ;
  • 김영신 (충남대학교 농업생명과학대학 생물환경화학과) ;
  • 김진철 (한국화학연구원 녹색화학분야) ;
  • 임치환 (충남대학교 농업생명과학대학 생물환경화학과)
  • Received : 2012.09.05
  • Accepted : 2012.09.21
  • Published : 2012.09.30
Download PDF
⟨ Previous Next ⟩

Abstract

In the continued research on natural fungicides for control of plant diseases by using plant-derived products, we found that Spatholobus suberectus Dunn had a strong fungicidal activity against several plant pathogens. S. suberectus (1 kg) was extracted with 80% aqueous MeOH and then the concentrated extract was partitioned with n-hexane, EtOAc, n-BuOH and $H_2O$ successively. The four layers were tested their disease contron efficacies against 6 plant diseases such as rice blast (RCB), rice sheath blight (RSB), tomato grey mold (TGM), tomato late blight (TLB), wheat leaf rust (WLR), and barley powdery mildew (BPM). The EtOAc fraction was highly active showing over 80% control against RCB, TGM, TLB, and BPM. By using silica gel chromatography, preparative TLC and HPLC, six compounds that were expected to have antifungal activity were separated. Their chemical structures were identified as ethanone, hydroxytyrosol, epicatechin, procyanidin B2, dimethoxy daizein and formononetin by ESI-MS, $^1H$-NMR, $^{13}C$-NMR, and 2D-NMR spectroscopic analyses. The chemicals except epicatechin were first reported in S. suberectus. Study on in vitro and in vivo antifungal activities of the isolated compounds is in progress.

계혈등으로부터 6종의 항균활성물질을 분리 정제하여 화학구조를 결정하였다. 계혈등 시료를 음건하여 80% aq. MeOH로 추출하고 감압 농축한 후 n-hexane, EtOAc, n-BuOH, 그리고 $H_2O$ 층으로 분획하였다. 각 분획을 이용하여 벼 도열별, 벼 잎집무늬마름병, 토마토 잿빛곰팡이병, 토마토 역병, 밀 붉은녹병, 보리 흰가루병 등 6가지 식물병에 대하여 식물병 방제효과를 검정한 결과, EtOAc 층이 가장 강한 활성을 보였으며, 벼 도열병, 토마토 잿빛 곰팡이병, 토마토 역병 및 보리 흰가루병에 대하여 80% 이상의 활성을 보였다. EtOAc층을 대상으로 silica gel chromatography 및 preparative TLC, HPLC 등을 이용하여 6종의 화합물을 분리, 정제하고 $^1H$-NMR, $^{13}C$-NMR, ESI-MS/MS, HMQC, $^1H-^1H$ COSY의 기기분석을 통해 ethanone, hydroxytyrosol, epicatechin, procyanidin B-2, dimethoxy daizein과 formononetin 으로 구조를 동정하였다. Epicatechin을 제외한 나머지 화합물들은 계혈등에서 처음으로 분리되었다. 분리한 물질들의 in vitro 및 in vivo 항균활성에 대한 연구를 진행하고 있다.

Keywords

References

  1. Baek, M. R., Y. H. Choi, D. S. Yoo, M. R. Kim, S. U. Choi, K. S. Hong, Y. S. Kim, Y. K. Kim, K. R. Lee and S. Y. Ryu (2009) Anti-proliferative components in the roots extract from Pueraria thunbergiana. Korean J. Pharmacogn. 40(1):46-50.
  2. Bais, H. P., R. Vepachedu, S. Gilroy, R. M. Callaway and J. M Vivanco. (2003) Allelopathy and exotic plant invasion: from molecules and genes to species interactions. Science 301:1377-1380. https://doi.org/10.1126/science.1083245
  3. Biancoa, A., M. A. Chiacchiob, G. Grassic, D. Iannazzod, A. Pipernod and R. Romeod (2006) Phenolic components of Olea europea: Isolation of new tyrosol and hydroxytyrosol derivatives. Food Chemistry 95:562-565. https://doi.org/10.1016/j.foodchem.2004.12.033
  4. Boskou, D. (2008) Olive oil minor constituents and health. CRC Press pp.28.
  5. Caligiani, A., G. Palla, A. Maietti, M. Cirlini and V. Brandolini (2010) 1H NMR fingerprinting of soybean extracts, with emphasis on identification and quantification of isoflavones. Nutrients, 2:280-289. https://doi.org/10.3390/nu2030280
  6. Cho, J. Y., G. J. Choi, S. W. Lee, H. Lim, K. S. Jang, C. H. Lim, K. Y. Cho and J. C. Kim (2006) In vivo antifungal activity against various plant pathogenic fungi of curcuminoids isolated from Curcuma longa L. rhizomes. Plant Pathology J. 22:94-96. https://doi.org/10.5423/PPJ.2006.22.1.094
  7. Cren-Olive, C., J. M,Wieruszeski, E. Maes and C. Rolando (2002) Catechin and epicatechin deprotonation followed by $^{13}C$ NMR. Tetrahedron Lett. 43:4545-4549. https://doi.org/10.1016/S0040-4039(02)00745-1
  8. Kanakubo, A., K. Koga, M. Isobe, T. Fushimi, T. Saitoh, Y. Ohshima and Y. Tsukamoto (2001) First finding of Daidzein 7-O-phosphate and Genistein 7-O-phosphate that are hydrolyzed by sulfatase. Tetrahedron 57:8801-8805. https://doi.org/10.1016/S0040-4020(01)00863-8
  9. Khan, M. R., D. S. D. Rutaihwa and G. L. Mhehe (2003) 1- (3-Hydroxy-4-methoxy-5-methylphenyl)ethanone, a new compound from the stem bark of Lamprothamnus zanguebaricus. Fitoterapia 74:741-742. https://doi.org/10.1016/S0367-326X(03)00193-X
  10. Kim, J. C., G. J. Choi, J. H. Park, H. T. Kim and K. Y Cho. (2001) Activity against plant pathogenic fungi of phomalactone isolated from Nigrospora sphaerica. Pest Manag. Sci. 57:554-559. https://doi.org/10.1002/ps.318
  11. Kim, Y. G., S. Ramachandran, D. C. Kim, Y. B. Hong, E. H. Kim, S. H. Kwon, S. J. Shin, S. D. Cha, I. S. Bae and C. H. Cho (2010) Isoliquiritigenin inhibited cell proliferation and triggered apoptosis in human endometrial cancer cell Line. J. Women's Med. 3:89-95. https://doi.org/10.5468/jwm.2010.3.3.89
  12. Kuiper, G. G., J. G. Lemmen, B. Carlsson, J. C. Corton, S. H. Safe, Saag P. van der, Burg B. van der and J. A. Gustafsson (1998) Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. Endocrinology 139:4252-63. https://doi.org/10.1210/en.139.10.4252
  13. Kumar, N. S., M. Rajapaksha (2005) Separation of catechin constituents from five tea cultivars using high-speed countercurrent chromatography. J. Chromatogr. 1083: 223-228. https://doi.org/10.1016/j.chroma.2005.06.013
  14. Kung, T. H., Y. H. Jian and Y. C. Kim (2005) Isoliquiritigenin: A Competitive Tyrosinase Inhibitor from the Heartwood of Dalbergia odorifera. J. Appl. Pharm. 13:32-34.
  15. Liu, Y., Y. Y. Zhao, H. B. Chen and Q. Y. Zhang (2010) Isolation and structural elucidation of an unstable isoflavonoid glycoside malonate from Radix hedysari. J. Chinese Pharm. Sci. 19:100-103.
  16. Ma, X., Tu P., Y. Chen, T. Zhang, Y. Wei and Y. Ito (2003) Preparative isolation and purification of two isoflavones from Astragalus membranaceus Bge. var. mongholicus (Bge.) Hsiao by high-speed counter-current chromatography. J. Chromatogr. 992:193-197. https://doi.org/10.1016/S0021-9673(03)00315-7
  17. Masami, H., K. Yukiko, N. Hideo, F. Yuko, K. Norihiko, N. Masaaki, M Wataru. and K. Yoshinobu (1999) Identification of The major antioxidative metabolites in biological fluids of the rat with ingested (+)-catechin and (−)-epicatechin. Biosci. Biotechnol. Biochem. 63:973-977. https://doi.org/10.1271/bbb.63.973
  18. Mateus, N., A. M. S. Silva, C. Santos-Buelga, J. C. Rivers- Gonzalo and V. D. Freitas (2002) Identification of anthocyanin-flavanol pigments in red wines by NMR and mass spectrometry. J. Agric. Food Chem. 50:2110-2116. https://doi.org/10.1021/jf0111561
  19. Messina, M. and A. H. Wu (2009) Perspectives on the soybreast cancer relation. Am. J. Clin. Nutr. 89:1673-1679. https://doi.org/10.3945/ajcn.2009.26736V
  20. Park, I. K., S. G. Lee, J. D. Park, S. C. Shin and Y. J. Ahn (2003) Fungicidal activity of domestic plant extracts against six major phytopathogenic fungi. Korean J. Pestic. Sci. 7(2):83-91.
  21. Rohrdanz, E., S. Ohler, Q. H. Tran-Thi and R. Kahl (2002) The phytoestrogen aidzein affects the antioxidant enzyme system of rat hepatoma H4IIE cells. J. Nutr. 132:370-375. https://doi.org/10.1093/jn/132.3.370
  22. Romero, C., M. Brenes, P. Garcia and A. Garrido (2002) Hydroxytyrosol 4-${\beta}$-D-Glucoside, an important phenolic compound in olive fruits and derived products. J. Agric. Food Chem. 50:3835-3839. https://doi.org/10.1021/jf011485t
  23. Shahat, A. A. (2006) Procyanidins from Adansonia digitata. Pharm. Biol. 44:445-450. https://doi.org/10.1080/13880200600798510
  24. Si, H. and D. Liu (2007) Phytochemical genistein in the regulation of vascular function: new insights. Curr. Med. Chem. 14:2581-2589. https://doi.org/10.2174/092986707782023325
  25. Takahashi, T., T. Kamiya, A. Hasegawa and Y. Yokoo (1999) Procyanidin B-2 study. J. Invest. Dermatol. 112:310-316. https://doi.org/10.1046/j.1523-1747.1999.00532.x
  26. Tuck, K. L., P. J. Hayball and I. Stupans (2002) Structural characterization of the metabolites of hydroxytyrosol, the principal phenolic component in olive oil, in rats. J. Agric. Food Chem. 50:2404-2409. https://doi.org/10.1021/jf011264n

Cited by

  1. 연교김패전(連翹金貝煎)의 Escherichia coli에 대한시험관내 항균력 평가 vol.28, pp.1, 2012, https://doi.org/10.15204/jkobgy.2015.28.1.029