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Isolation and identification of antifungal compounds from Reynoutria elliptica

호장근(Reynoutria elliptica)으로부터 항균활성 물질의 분리 및 구조결정

  • Hwang, Joo-Tae (Department of Bio Environmental Chemistry, Chungnam National University) ;
  • Park, Young-Sik (Department of Bio Environmental Chemistry, Chungnam National University) ;
  • Kim, Young-Shin (Department of Bio Environmental Chemistry, Chungnam National University) ;
  • Kim, Jin-Cheol (Chemical Biotechnology Research Center, Korea Research Institute of Chemical Technology) ;
  • Lim, Chi-Hwan (Department of Bio Environmental Chemistry, Chungnam National University)
  • 황주태 (충남대학교 생물환경화학과) ;
  • 박영식 (충남대학교 생물환경화학과) ;
  • 김영신 (충남대학교 생물환경화학과) ;
  • 김진철 (한국화학연구원 바이오 정밀화학연구센터) ;
  • 임치환 (충남대학교 생물환경화학과)
  • Received : 2012.11.12
  • Accepted : 2012.12.12
  • Published : 2012.12.31

Abstract

In the continued research on natural fungicides for the control of plant diseases by using plant-derived products, we found that Reynoutria elliptica. had a strong fungicidal activity against several plant pathogens. R. elliptica (3.2 kg) were extracted with 80% aq. MeOH and the concentrated extracted was partitioned with n-hexane, EtOAc, n-BuOH and $H_2O$ successively. The four layers were tested their disease control efficacies against 4 plant disease such as rise blast (RCB), tomato grey mold (TGM), tomato late blight (TLB), and barly powdery mildew (BPM). The n-hexane fraction was highly active showing over 95% control against TLB and BPM. and the EtOAc fraction was highly active showing over 95% control against RCB, TLB, and BPM. By using silica gel chromatography, MPLC, and HPLC, three compounds that were expected to have antifungal activity were isolated. Their chemical structures were elucidated as physcion, emodin, and emodie-8-O-glucoside by EI-MS and NMR spectroscopic analyses.

Keywords

References

  1. Chaoyun W, Dalei Z, Hongmei M, Juntian L. 2007. Neuroprotective effects of emodin-8-O-$\beta$-d-glucoside in vivo and in vitro. European Journal of Pharmacology 577:58-63. https://doi.org/10.1016/j.ejphar.2007.08.033
  2. Chi HJ, Choi JR, Yu SC. 1982. Pharmacognostical studies on Ho-Jang. Korea Journal of Pharmacology 13(4):145-152. [in Korean]
  3. Cho JY, Choi GJ, Lee SW, Lim H, Jang KS, Lim CH, Cho KY. Kim JC. 2006. In vivo antifungal activity against various plant pathogenic fungi of curcuminoids isolated from Curcuma longa L. rhizomes. Plant Pathology Journal 22:94-96. https://doi.org/10.5423/PPJ.2006.22.1.094
  4. Chun G. 2010. Anti-tumor activity of emodin against human chronic myelocytic leukemia K562 cell lines in vitro and in vivo. European Journal of Pharmacology 627:33-40. https://doi.org/10.1016/j.ejphar.2009.10.035
  5. Cooper RM. 1996. Detection and cellular localization of elemental sulphur in disease-resistant genotypes of Theobroma cacao. Nature 379:159-162. https://doi.org/10.1038/379159a0
  6. Coskun M, Satake T, Hori K, Saiki Y, Tanker M. 1990. A new anthraquinone glycoside, physcion 8-O-$\beta$-rutinoside, was isolated from the bark of R. libanoticus together with emodin, its 6-O-$\alpha$-L-rhamnoside and 8-O-$\beta$-D-glucoside, and kaempferol. Phytochemistry 29(6):2018-2020. https://doi.org/10.1016/0031-9422(90)85060-S
  7. Feng Y, Huang SL, Dou W, Zhang S, Chen JH, Shen Y, Shen JH, Leng Y. 2010. Emodin, a natural product, selectively inhibits 11$\beta$-hydroxysteroid dehydrogenase type 1 and ameliorates metabolic disorder in diet-induced obese mice. British Journal of Pharmacology 161(1):113-126. https://doi.org/10.1111/j.1476-5381.2010.00826.x
  8. Fukui H, Egawa H, Koshimizu K, Mitsui T. 1973. New isoflavone with antifungal activity from immature fruits of Lupinus luteus. Agricultural and Biological Chemistry 37(2): 417-421. https://doi.org/10.1271/bbb1961.37.417
  9. Hector RB, Waldo L 1996. Antialgal and antifungal activity of natural hydroxamic acids and related compounds. Journal of Agricultural and Food Chemistry 44:1569-1571. https://doi.org/10.1021/jf950345e
  10. Hofman J, Hofmanova O. 1971. 1,4-Benzoxazine derivatives in plants absence of 2,4-dihydroxy-7-methoxy-2H-1,4-benxozazin- 3(4H)-one from uninjured Zea mays plants. Phytochemistry 10:1441-1444. https://doi.org/10.1016/0031-9422(71)85005-7
  11. Kato T, Morita Y. 1987. Anthraquinone components in Rumex acetosa L. Shoyakugaku Zasshi 41(1):67-74.
  12. Kim DK, Choi SU. 1998. Cytotoxic constituents of Rumex japonicus. Yakhak Hoeji 42:233-237.
  13. Kim JC, Choi G., Park JH, Kim HT, Cho KY. 2001. Activity against plant pathogenic fungi of phomalactone isolated from Nigrospora sphaerica. Pest Management Science 57:554-559. https://doi.org/10.1002/ps.318
  14. Ma X, Yang X, Zeng F, Yang L, Yu D, Ni H. 2010. Physcion, a natural anthraquinone derivative, enhances the gene expression of leaf-specific thionin of barley against Blumeria graminis. Pest Management Science 66(7):718-724. https://doi.org/10.1002/ps.1933
  15. Reyes-Chilpa R, Gomez-Garibay F, Moreno-Torres G, Jimenez- Estrada M, Quiroz-Vasquez, RI. 1998. Flavonoids and isoflavonoids with antifungal properties from Platymiscium yucatanum heartwood. Holzforschung 52(5):459-462. https://doi.org/10.1515/hfsg.1998.52.5.459
  16. Richard AD. 2001. Natural products and plant disease resistance. Nature 411:843-847. https://doi.org/10.1038/35081178
  17. Sirat HM, Russell GB. 1989. The isolation and identification of two antifungal pterocarpans from Ulex europaeus L. Pertanika 12(3):395-398.
  18. Srinivas G, Babykutty S, Sathiadevan PP, Srinivas P. 2007. Molecular mechanism of emodin action: transition from laxative ingredient to an antitumor agent. Medicinal Research Reviews 27(5):591-608. https://doi.org/10.1002/med.20095
  19. Soledade M, Pedras C, Jun L. 2004. Designer phytoalexin: probing calmalexin detoxification pathways in the phytopathogen Rhizoctonia solani. Organic Biomolecular Chemistry 2:1070-1076. https://doi.org/10.1039/b400031e
  20. Vanetten HD, Matthews DE, Matthews PS. 1989. Phytoalexin detoxification: importance for pathogenicity and practical implications. Annual Review of Phytopathology 27:143-164. https://doi.org/10.1146/annurev.py.27.090189.001043
  21. Vollekova A, Kost'alova D, Kettmann V, Toth J. 2003. Antifungal activity of Mahonia aquifolium extract and its major protoberberine alkaloids. Phytotherapy Research 17(7):834-837. https://doi.org/10.1002/ptr.1256
  22. Xiang MX , Xu , Su HW, Hu J, Yan Y. 2011. Emodin-8-O-$\beta$-D-glucoside from Polygonum Amplexicaule D. Don var. Sinense Forb. promotes proliferation and differentiation of osteoblastic MC3T3-E1 cells. Molecules 16(1):728-737. https://doi.org/10.3390/molecules16010728
  23. Ye M, Han J, Chen H, Zheng J, Guo D. 2007. Analysis of phenolic compounds in rhubarbs using liquid chromatography coupled with electrospray ionization mass spectrometry. Journal of the American Society for Mass Spectrometry 18(1):82-91. https://doi.org/10.1016/j.jasms.2006.08.009

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