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Antifungal Activities of Dimeric Sesquiterpenes, Shizukaols C and F, Isolated from Chloranthus japonicus Sieb.

  • Kang, Tae Hoon (Industrial Bio-materials Research Center, KRIBB) ;
  • Lee, Yun Me (Industrial Bio-materials Research Center, KRIBB) ;
  • Lee, Won Jung (Industrial Bio-materials Research Center, KRIBB) ;
  • Hwang, Eui Il (Technical Research Center, KT&G R&D Headquaters) ;
  • Park, Ki Duk (Convergence Research Center for Diagnosis, Treatment and Care System of Dementia, KIST) ;
  • Choi, Gyung Ja (Center for Eco-friendly New Materials, KRICT) ;
  • Moon, Jae Sun (Industrial Bio-materials Research Center, KRIBB) ;
  • Park, Ho-Yong (Industrial Bio-materials Research Center, KRIBB) ;
  • Kim, Sung Uk (Industrial Bio-materials Research Center, KRIBB)
  • Received : 2017.01.10
  • Accepted : 2017.05.21
  • Published : 2017.07.28

Abstract

Two dimeric sesquiterpenes were separated from Chloranthus japonicus Sieb. and identified as shizukaols C and F. They exhibited potent antifungal activities ($MICs=4-16{\mu}g/ml$) in vitro against various plant pathogenic fungi (Pythium ultimum, Phytophthora infestans, Botrytis cinerea, Colletotrichum lagenarium, Alternaria kikuchiana, and Magnaporthe grisea). Shizukaol C showed 88% and 91% protective activities in the greenhouse against Puccinia recondita (wheat leaf rust) and Phytophthora infestans (tomato late blight), respectively, at $100{\mu}g/ml$; shizukaol F exhibited 93% antifungal activity against Puccinia recondita at the same concentration. Therefore, these compounds might serve as interesting candidates for effective antifungal agents.

Keywords

References

  1. Aktar MW, Sengupta D, Chowdhury A. 2009. Impact of pesticides use in agriculture: their benefits and hazards. Interdiscip. Toxicol. 2: 1-12. https://doi.org/10.2478/v10102-009-0001-7
  2. Soda M. 2000. Bacterial control of plant diseases. J. Biosci. Bioeng. 6: 515-521.
  3. Tanaka K, Amaki Y, Ishihara A, Nakajima H. 2015. Synergistic effect of [Ile7] surfactin homologues with bacillomycin D in suppression of gray molds disease by Bacillus amyloliquefaciens biocontrol strain SD-32. J. Agric. Food Chem. 63: 5344-5353. https://doi.org/10.1021/acs.jafc.5b01198
  4. Pimentel D, Acquay H, Biltonen M, Rice P, Silva M, Nelson J, et al. 1992. Environmental and economic costs of pesticides use. Bioscience 42: 750-760. https://doi.org/10.2307/1311994
  5. De Wager LA, van der Bij AJ, Dekkers LC, Simons M, Wijffelman CA, Lugtenberg BJJ. 1995. Colonization of the rhizosphere of crop plants by plant-beneficial pseudomonads. FEMS Microbiol. Ecol. 17: 221-228. https://doi.org/10.1111/j.1574-6976.1995.tb00205.x
  6. Arguelles-Arias A, Ongena M, Halimi B, Lara Y, Brans A, Joris B, et al. 2009. Bacillus amyloliquefaciens GA1 as a source of potent antibiotics and other secondary metabolites for biocontrol of plant pathogens. Microb. Cell Fact. 8: 63. https://doi.org/10.1186/1475-2859-8-63
  7. Jung BS, Shin MK. 1998. Encyclopedia of Illustrated Korean Natural Drugs, pp. 813-814. Young Lim Sa, Seoul, Korea.
  8. Jiangsu New Medical College. 1986. Dictionary of Chinese Traditional Medicine (Zhong Yao Da Ci Dian), Vol. 2, pp. 2169-2173. Shanghai Science and Technology Press, Shanghi, China.
  9. Kawabata J, Fukushi Y, Tahara S, Mizutani J. 1984. Structures of novel sesquiterpene alcohols from Chloranthus japonicus (Chloranthaceae). Agric. Biol. Chem. 48: 713-717.
  10. Kuang H, Xia Y, Yang B, Wang Q, Lu S. 2008. Sesquiterpene glucosides from Chloranthus japonicus Sieb. Chem. Biodivers. 5: 1736-1742. https://doi.org/10.1002/cbdv.200890162
  11. Wu B, Qu H, Cheng Y. 2008. New sesquiterpenes from Chloranthus japonicus. Helv. Chim. Acta 91: 725-733. https://doi.org/10.1002/hlca.200890073
  12. Yim NH, Hwang EI, Yun BS, Park KD, Moon JS, Lee SH, et al. 2008. Sesquiterpene furan compound CJ-01, a novel chitin synthase 2 inhibitor from Chloranthus japonicus Sieb. Biol. Pharm. Bull. 31: 1041-1044. https://doi.org/10.1248/bpb.31.1041
  13. Kawabata J, Mizutani J. 1989. Shizukanolides D, E and F, novel lindenanolides from Chloranthus spp. (Chloranthaceae). Agric. Biol. Chem. 53: 203-207.
  14. Kawabata J, Tahara S, Mizutani J. 1981. Isolation and structural elucidation of four sesquiterpenes from Chloranthus japonicus (Chloranthaceae). Agric. Biol. Chem. 45: 1447-1453.
  15. Uchida M, Koike Y, Kusano G, Kondo Y, Nozoe S, Kabuto C, et al. 1980. Studies on the constituents of Chloranthus spp. III. Six sesquiterpenes from Chloranthus japonicus. Chem. Pharm. Bull. 28: 92-102. https://doi.org/10.1248/cpb.28.92
  16. Kawabata J, Tahara S, Mizutani J, Furusaki A, Hashiba N, Matsumoto T. 1979. Shizukanolides, two sesquiterpenoids from Chloranthus japonicus (Chloranthaceae). Agric. Biol. Chem. 43: 885-887.
  17. Kawabata J, Fukushi E, Mizutani J. 1995. Sesquiterpene dimer from Chloranthus japonicus. Phytochemistry 39: 121-125. https://doi.org/10.1016/0031-9422(94)00865-Q
  18. Kawabata J, Fukushi E, Mizutani J. 1998. Sesquiterpene dimer from Chloranthus japonicus. Phytochemistry 47: 231-235. https://doi.org/10.1016/S0031-9422(97)00419-6
  19. Kawabata J, Fukushi Y, Tahara S, Mizutani J. 1990. Shizukaol A, a sesquiterpene dimer from Chloranthus japonicus. Phytochemistry 29: 2332-2334. https://doi.org/10.1016/0031-9422(90)83065-9
  20. Wang QH, Kuang HX, Yang BY, Xia YG, Wang JS, Kong LY. 2011. Sesquiterpenes from Chloranthus japonicus. J. Nat. Prod. 74: 16-20. https://doi.org/10.1021/np100504m
  21. Kim SY, Nagashima H, Tanaka N, Kashiwada Y, Kobayashi J, Kojoma M. 2016. Hitorins A and B, haxacyclic C25 terpenoids from Chloranthus japonicus. Org. Lett. 18: 5420-5423. https://doi.org/10.1021/acs.orglett.6b02842
  22. Kwon OE, Lee HS, Lee SW, Bae KH, Kim K, Hayashi M, et al. 2006. Dimeric sesquiterpenoids isolated from Chloranthus japonicus inhibited the expression of cell adhesion molecules. J. Ethnopharmacol. 104: 270-277. https://doi.org/10.1016/j.jep.2005.09.018
  23. Fang PL, Cao YL, Yan H, Pan LL, Liu SC, Gong NB, et al. 2011. Lindenane disesquiterpenoids with anti-HIV-1 activity from Chloranthus japonicus. J. Nat. Prod. 74: 1408-1413. https://doi.org/10.1021/np200087d
  24. Zhao JJ, Guo YQ, Yang DP, Xue X, Liu Q, Zhu LP, et al. 2016. Chlojaponilactone B from Chloranthus japonicus: suppression of inflammatory responses via inhibition of the NF-${\kappa}$B signaling pathway. J. Nat. Prod. 79: 2257-2263. https://doi.org/10.1021/acs.jnatprod.6b00355
  25. Kawabata J, Mizutani J. 1992. Dimeric sesquiterpenoid esters from Chloranthus serratus. Phytochemistry 31: 1293-1296. https://doi.org/10.1016/0031-9422(92)80281-I
  26. Lee YM, Moon JS, Yun BS, Park KD, Choi GJ, Kim JC, et al. 2009. Antifungal activity of CHE-23C, a dimeric sesquiterpene from Chloranthus henryi. J. Agric. Food Chem. 57: 5750-5755. https://doi.org/10.1021/jf900674y
  27. Wu B, He S, Pan Y. 2007. Sesquiterpenoid with new skeleton from Chloranthus henryi. Tetrahedron Lett. 48: 453-456. https://doi.org/10.1016/j.tetlet.2006.11.054
  28. Wu B, He S, Wu XD, Pan YJ. 2006. Bioactive terpenes from the roots of Chloranthus henryi. Planta Med. 72: 1334-1338. https://doi.org/10.1055/s-2006-947256
  29. Wu B, He S, Wu XD, Pan YJ. 2008. New tyrosinase inhibitory sesquiterpenes from Chloranthus henryi. Chem. Biodivers. 5: 1298-1303. https://doi.org/10.1002/cbdv.200890116
  30. Yang SP, Gao ZB, Wu Y, Hu GY, Yue JM. 2008. Chlorahololides C-F: a new class of potent and selective potassium channel blockers from Chloranthus holostegius. Tetrahedron 64: 2027-2034. https://doi.org/10.1016/j.tet.2007.12.057
  31. Tang L, Zhu H, Yang X, Xie F, Peng J, Jiang D, et al. 2016. Shizukaol D, a dimeric sesquiterpene isolated from Chloranthus serratus, represses the growth of human liver cancer cells by modulating Wnt signaling pathway. PLoS One 11: e0152012. https://doi.org/10.1371/journal.pone.0152012
  32. Kim JC, Choi GJ, Park JH, Kim HT, Cho KY. 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

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