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http://dx.doi.org/10.5656/KSAE.2011.04.0.15

Structure-activity Analysis of Benzylideneacetone for Effective Control of Plant Pests  

Seo, Sam-Yeol (Department of Bioresource Sciences, Andong National University)
Jun, Mi-Hyun (Department of Bioresource Sciences, Andong National University)
Chun, Won-Su (Department of Bioresource Sciences, Andong National University)
Lee, Sung-Hong (Department of Applied Chemistry, Andong National University)
Seo, Ji-Ae (B&L agro)
Yi, Young-Keun (Department of Bioresource Sciences, Andong National University)
Hong, Yong-Pyo (Department of Applied Chemistry, Andong National University)
Kim, Yong-Gyun (Department of Bioresource Sciences, Andong National University)
Publication Information
Korean journal of applied entomology / v.50, no.2, 2011 , pp. 107-113 More about this Journal
Abstract
Benzylideneacetone (BZA) is a compound derived from culture broth of an entomopathogenic bacterium, Xenorhabdus nematophila (Xn). Its immunosuppressive activity is caused by its inhibitory activity against eicosanoid biosynthesis. This BZA is being developed as an additive to enhance control efficacy of other commercial microbial insecticides. This study was focused on the enhancement of the immunosuppressive activity of BZA by generating its chemical derivatives toward decrease of its hydrophobicity. Two hydroxylated BZA and one sugar-conjugated BZA were chemically synthesized. All derivatives had the inhibitory activities of BZA against phospholipase $A_2$ ($PLA_2$) and phenoloxidase (PO) of the diamondback moth, Plutella xylostella, but BZA was the most potent. Mixtures of any BZA derivative with Bacillus thuringiensis (Bt) significantly increased pathogenicity of Bt. BZA also inhibited colony growth of four plant pathogenic fungi. However, BZA derivatives (especially the sugar-conjugated BZA) lost the antifungal activity. These results indicated that BZA and its derivatives inhibited catalytic activities of two immune-associated enzymes ($PLA_2$ and PO) of P. xylostella and enhanced Bt pathogenicity. We suggest its use to control plant pathogenic fungi.
Keywords
Benzylideneacetone; Plutella xylostella; Plant pathogen; Phospholipase $A_2$; Phenoloxidase;
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1 Broderick, N.A., K.F. Raffa and J. Handelsman. 2006. Midgut bacteria required for Bacillus thuringiensis insecticidal activity. Proc. Natl. Acad. Sci. USA 103: 15196-15199.   DOI
2 Chung, B.G., S.W. Kang and H.Y. Choo. 1997. Joint toxic action of bifenthrin and prothiofos mixture for the control of insecticideresistant diamondback moth, Plutella xylostella L. Kor. J. Appl. Entomol. 36: 105-110.
3 Dennis, E.A. 1997. The growing phospholipase $A_2$ superfamily of signal transduction enzymes. Trends Biochem. Sci. 22: 1-2.   DOI
4 Gill, S.S., E.A. Cowles and P.V. Pietrantonio. 1992. The mode of action of Bacillus thuringiensis endotoxins. Annu. Rev. Entomol. 37: 615-636.   DOI
5 Shrestha, S. and Y. Kim. 2008. Eicosanoids mediate prophenoloxidase release from oenocytoids in the beet armyworm Spodoptera exigua. Insect Biochem. Mol. Biol. 38: 99-112.   DOI
6 Shrestha, S. and Y. Kim. 2009. Biochemical characteristics of immune-associated phospholipase $A_2$ and its inhibition by an entomopathogenic bacterium, Xenorhabdus nematophila. J. Microbiol. 47: 774-782.   DOI
7 Stanley, D.W. 2000. Eicosanoids in Invertebrate Signal Transduction Systems. Princeton University Press, New Jersey, USA.
8 Stanley, D.W. 2006. Prostaglandins and other eicosanoids in insects: biological significance. Annu. Rev. Entomol. 51: 25-44.   DOI
9 Stanley, D.W. and J.S. Miller. 2006. Eicosanoid actions in insect cellular immune functions. Entomol. Exp. Appl. 119:1-13.   DOI
10 Tabashnik, B.E. 1994. Evolution of resistance to Bacillus thuringiensis. Annu. Rev. Entomol. 39: 47-79.   DOI
11 Zhang, X., N.B. Griko, S.K. Corona and L.A. Bulla, Jr. 2008. Enhanced exocytosis of the receptor BT-R(1) induced by the Cry1Ab toxin of Bacillus thuringiensis directly correlates to the execution of cell death. Comp. Biochem. Physiol. B 149: 581-588.   DOI
12 Kim, M.H. and S.C. Kim. 1991. Bionomics of diamondback moth, Plutella xylostella (Lepidoptera: Plutellidae) in southern region of Korea. Kor. J. Appl. Entomol. 30: 169-173.
13 Kwon, S. and Y. Kim. 2008. Benzylideneacetone, an immunosuppressant, enhances virulence of Bacillus thuringiensis against beet armyworm (Lepidoptera: Noctuidae). J. Econ. Entomol. 101: 36-41.   DOI
14 Park, Y.S, M.J. Kim, G.H. Lee, W.S. Cheon, Y.G. Lee and Y. Kim. 2009. Inhibitory effects of an eicosanoid biosynthesis inhibitor, benzylideneacetone, against two spotted spider mite, Tetranychus urticae, and a bacterial wilt-causing pathogen, Ralstonia solanacearum. Kor. J. Pesti. Sci. 3: 185-189.   과학기술학회마을
15 Seo, S. and Y. Kim. 2009. Two entomopathogenic bacteria, Xenorhabdus nematophila K1 and Photorhabdus temperata subsp. temperata ANU101 secrete factors enhancing Bt pathogenicity against the diamondback moth, Plutella xylostella. Kor. J. Appl. Entomol. 38: 385-392.   과학기술학회마을   DOI
16 Park, S.J., M.H. Jun, W.S. Cheon, J.A. Seo, Y.G. Lee and Y. Kim. 2010. Control effects of benzylideneacetone isolated from Xenorhabdus nematophila K1 on the diseases of red-pepper plants. Res. Plant Dis. 16: 170-175.   DOI   ScienceOn
17 Radvanyi, F., L. Jordan, F. Russo-Marie and C. Bon. 1989. A sensitive and continuous fluorometric assay for phospholipase $A_2$ using pyrene-labeled phospholipids in the presence of serum albumin. Anal. Biochem. 177: 103-109.   DOI
18 SAS Institute, Inc. 1989. SAS/STAT user's guide, Release 6.03, Ed. Cary, N.C.
19 Seo, S. and Y. Kim. 2010. Study on development of novel biopesticides using entomopathogenic bacterial culture broth of Xenorhabdus and Photorhabdus. Kor. J. Appl. Entomol. 49: 241-249.   과학기술학회마을   DOI
20 Hoffman, C., H. Vanderbruggen, H. Hofte, J. Van Rie, S. Jansens and H. Van Mellaert. 1988. Specificity of Bacillus thuringiensis delta-endotoxins is correlated with the presence of high-affinity binding sites in the brush border membrane of target insect midguts. Proc. Natl. Acad. Sci. USA 85: 7844-7848.   DOI
21 Hwang, B.G. 2002. Studies of resistance of pepper to phytophthora blight and its control. Res. Plant Dis. 8: 131-145.   과학기술학회마을   DOI
22 Jenkins, J.I. and D.H. Dean. 2000. Exploring the mechanism of action of insecticidal proteins by genetic engineering methods. pp. 33-54. In Genetic engineering: principles and methods, vol. 22. eds. by K. Setlow. Plenum, New York.
23 Kanost, M.R. and M.J. Gorman. 2008. Phenoloxidase in insect immunity. pp. 69-96. In Insect immunity, ed. by N.E. Beckage. Academic Press, San Diego, USA.
24 Ji, D., Y. Yi, G.H. Kang, Y.H. Choi, P. Kim, N.I. Baek and Y. Kim. 2004. Identification of an antibacterial compound, benzylideneacetone, from Xenorhabdus nematophila against major plant-pathogenic bacteria. FEMS Microbiol. Lett. 239: 241-248.   DOI
25 Jung, S.C. and Y. Kim. 2006. Synergistic effect of Xenorhabdus nematophila K1 and Bacillus thuringiensis subsp. aizawai against Spodoptera exigua (Lepidoptera: Noctuidae). Biol. Control 39: 201-209.   DOI
26 Kanost, M.R., H. Jiang and X. Yu. 2004. Innate immune responses of a lepidopteran insects, Manduca sexta. Immunol. Rev. 198: 97-105.   DOI
27 Kennedy, R., and R. Collier. 2000. Pests and diseases of field vegetables. pp. 185-257. In Pest and disease management handbook, ed. by D.V. Alford. Blackwell Science, Oxford, UK.
28 Kim, G.H., Y. S. Seo, J.H. Lee and K.Y. Cho. 1990. Development of fenvalerate resistance in the diamondback moth, Plutella xylostella Linne (Lepidoptera: Yponomeutidae) and its cross resistance. Kor. J. Appl. Entomol. 29: 194-200.