• Title, Summary, Keyword: 벤질리덴아세톤

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Structure-activity Analysis of Benzylideneacetone for Effective Control of Plant Pests (벤질리덴아세톤 화학구조 변이에 따른 생리활성 변화 분석 및 식물 병해충 방제 효과)

  • Seo, Sam-Yeol;Jun, Mi-Hyun;Chun, Won-Su;Lee, Sung-Hong;Seo, Ji-Ae;Yi, Young-Keun;Hong, Yong-Pyo;Kim, Yong-Gyun
    • Korean journal of applied entomology
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    • v.50 no.2
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    • pp.107-113
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    • 2011
  • 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.

Control Effects of Benzylideneacetone Isolated from Xenorabdus nematophilla K1 on the Diseases of Redpepper Plants (Xenorhabdus nematophilla 유래물질 벤질리덴아세톤의 고추 병해 방제 효과)

  • Park, Su-Jin;Jun, Mi-Hyun;Chun, Won-Su;Seo, Ji-Ae;Yi, Young-Keun;Kim, Yong-Gyun
    • Research in Plant Disease
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    • v.16 no.2
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    • pp.170-175
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    • 2010
  • A monoterpenoid benzylideneacetone (BZA) is a bacterial metabolite isolated from culture broth of an entomopathogenic bacterium, Xenorhabdus nematophila K1. It was tested in this study the control efficacy of the metabolite against two major fungal diseases occurring in red-pepper plants. BZA exhibited significant antifungal activities against Phytophthora capsici and Colletotrichum acutatum. Under natural light conditions, the antifungal activity of BZA was maintained for more than sixty days. The antifungal activity of BZA was not lost even in soil because the incidence of Phytophthora blight against red-pepper plants was significantly reduced when the suspensions of P. capsici were poured to the rhizosphere soils mixed with BZA. Application of the BZA suspension spray to the fruit surface infected with C. acutatum significantly suppressed the disease occurrence of anthracnose on the red-pepper plants. These results suggest that BZA can be used to develop a promising agrochemical to control phytophthora blight and anthracnose of redpepper plants.

Inhibitory Effects of an Eicosanoid Biosynthesis Inhibitor, Benzylideneacetone, Against Two Spotted Spider Mite, Tetranychus urticae, and a Bacterial Wilt-causing Pathogen, Ralstonia solanacearum (아이코사노이드 생합성 저해제인 벤질리덴아세톤의 점박이응애(Tetranychus urticae)와 세균성풋마름병 세균(Ralstonia solanacearum)에 대한 억제효과)

  • Park, Ye-Sol;Kim, Min-Je;Lee, Geon-Hyung;Chun, Won-Soo;Yi, Young-Keun;Kim, Yong-Gyun
    • The Korean Journal of Pesticide Science
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    • v.13 no.3
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    • pp.185-189
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    • 2009
  • A monoterpenoid compound, benzylideneacetone (BZA), is a metabolite of an entomopathogenic bacterium, Xenorhabdus nematophila. Its primary biological activity is an inhibitor of phospholipase $A_2$, which catalyzes the committed step of biosynthesis of various eicosanoids that are critically important to mediate insect immune responses. When BZA was applied to two-spotted spider mite, Tetranychus urticae, it exhibited a dose-dependent mortality in leaf-disc assay. Subsequently BZA was tested against T. urticae infesting apples in a field orchard, in which it showed a significant control efficacy, which was not statistically different with that of a commercial acaricide. BZA also had significant antibacterial activities against three species of plant pathogenic bacteria when it was added to the bacterial cultures, in which it showed the highest inhibitory activity against a bacterial wilt-causing pathogen, Ralstonia solanacearum. The bacterial pathogen caused significant disease symptom to young potato plants. However, BZA significantly suppressed the disease occurrence. This study suggests that BZA can be used to develop a novel crop protectant to control mite and bacterial pathogen.

Comparative Analysis of Benzylideneacetone-derived Compounds on Insect Immunosuppressive and Antimicrobial Activities (벤질리덴아세톤 유도 화합물들의 곤충면역반응 억제와 살균력 비교 분석)

  • Seo, Sam-Yeol;Chun, Won-Su;Hong, Yong-Pyo;Yi, Young-Keun;Kim, Yong-Gyun
    • Korean journal of applied entomology
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    • v.51 no.3
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    • pp.245-253
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    • 2012
  • Benzylinedeneacetone (BZA) is a bacterial metabolite which is synthesized by at least two entomopathogenic bacteria, namely Xenorhabdus nematophila and Photorhabdus temperata subsp. temperata. It has been shown to possess inhibitory effects on insect cellular and humoral immune responses as well as antimicrobial activities against various species of bacteria and fungi. However, its relatively high phytotoxicity, and nonsystematic effect have thus far prevented its development into an optimal pesticide. This study screened five different BZA derivatives in order to select an optimal compound, which would have relatively high solubility and low phytotoxicity while retaining sufficient degrees of the immunosuppressive and antimicrobial activities associated with BZA. Hydroxylation of the benzene ring of BZA was found to significantly suppress its immunosuppressive and antimicrobial activities. Transformation of the ketone of BZA by carboxylation also suppressed the inhibitory activities. However, a shortening of the aliphatic chain of BZA into acetate form (4-hydroxyphenylacetic acid: HPA) did not decrease the inhibitory activity. HPA also showed much less phytotoxicity against the hot pepper plant Capsicum annuum, when compared to BZA. This study identified an optimal BZA derivative, which exhibited relatively little phytotoxicity, but retained a high degree of inhibitory activity to suppress insect immune responses and antimicrobial activities against plant pathogens.

Antibiotic and Insecticidal Activities of Metabolites Derived From an Entomopathogenic Bacterium, Xenorhabdus nematophila, Against The Bean Bug, Riptortus clavatus (곤충병원세균(Xenorhabdus nematophila) 유래물질의 톱다리개미허리노린재(Riptortus clavatus) 장내세균 증식억제 및 살충효과)

  • Seo, Sam-Yeol;Kim, Yong-Gyun
    • Korean journal of applied entomology
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    • v.49 no.3
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    • pp.251-259
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    • 2010
  • A bacterial colony was isolated from the gut of the bean bug, Riptortus clavatus. From morphological and biochemical tests, the bacterial isolate showed the highest similarity to Staphylococcus succinus. DNA sequence of 16S rRNA gene of the bacterium supported the identification. Oral administration of penicillin G to adults of R. clavatus gave a dose-dependent mortality of adults of R. clavatus to adults along with significant decrease of the bacterial population in the gut. Similarly, three metabolites (benzylideneacetone, proline-tyrosine, and acetylated phenylalanine-glycine-valine) derived from an entomopathogenic bacterium, Xenorhabdus nematophila, also inhibited growth of the gut bacterial population and gave significant mortalities to R. clavatus. These results suggest that a gut bacterial population classified as Staphylococcus sp. is required for survival of R. clavatus and that the three bacterial metabolites had toxic effects on the bugs due to their antibacterial properties.

Enhancement of Bt-Plus Toxicity by Unidentified Biological Response Modifiers Derived from the Bacterial Culture Broth of Xenornabdus nematiphila (Xenorhabuds nematophila 세균 배양액 유래 미확인 생리활성 물질의 비티플러스 살충력 상승효과)

  • Park, Youngjin;Kim, Minwoo;Kim, Kunwoo;Kim, Yonggyun
    • Korean journal of applied entomology
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    • v.54 no.2
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    • pp.55-62
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    • 2015
  • 'Bt-Plus' has been developed by mixing spores of Bacillus thuringiensis (Bt) and culture broth of Xenorhabdus nematophila (Xn). Despite its high toxicity, it has some imitation to broaden its efficacy against diverse insect pest spectrum. This study focuses on enhancement of Bt-Plus toxicity against semi-susceptible insect, Spodoptera exitgua, by addition of Xn metabolites. Two main Xn metabolites, oxindole (OI) and benzylideneacetone (BZA), are known to enhance the Bt insecticidal activities. The addition of OI or BZA significantly increased Bt-Plus pathogenicity. However, when the freeze-dried Xn culture broth was added to Bt-Plus, much less amount was enough to enhance the toxicity compared to the amount of OI or BZA. An HPLC analysis indicated that there were more than 12 unidentifed bacterial metabolites in Xn culture broth. These suggest that there are potent biological response modifiers in Xn metabolites other than OI and BZA.

Toxicity Evaluation of 'Bt-Plus' on Parasitoid and Predatory Natural Enemies (기생성 및 포식성 천적에 대한 작물보호제 '비티플러스'의 독성 평가)

  • Seo, Sam-Yeol;Srikanth, Koigoora;Kwon, Gi-Myon;Jang, Sin-Ae;Kim, Yong-Gyun
    • Korean journal of applied entomology
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    • v.51 no.1
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    • pp.47-58
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    • 2012
  • Effect of a new crop protectant 'Bt-Plus' on natural enemies was analyzed in this study. Tested natural enemies included two parasitic species of $Aphidius$ $colemani$ and $Eretmocerus$ $eremicus$, and four predatory species of $Harmonia$ $axyridis$, $Orius$ $laevigatus$, $Amblyseius$ $swirskii$, and $Phytoseiulus$ $persimilis$. 'Bt-Plus' was formulated by combination of three entomopathogenic bacteria ($Xenorhabdus$ $nematophila$ (Xn), $Photorhabdus$ $temperata$ subsp. $temperata$ (Ptt), $Bacillus$ $thuringiensis$ (Bt)) and bacterial metabolite (BM). All three types of 'Bt-Plus' showed significantly higher toxicities against fourth instar $Plutella$ $xylostella$ larvae than Bt single treatment. Two types of bacterial mixtures ('Xn+Bt' and 'Ptt+Bt') showed little toxicity to all natural enemies in both contact and oral feeding assays. However, 'BM+Bt' showed significant toxicities especially to two predatory mites of $A.$ $swirskii$ and $P.$ $persimilis$. The acaricidal effects of different bacterial metabolites were evaluated against two spotted spider mite, $Tetranychus$ $urticae$. All six BM chemicals showed significant acaricidal effects. The BM mixture used to prepare 'Bt-Plus' showed a high acaricidal activity with a median lethal concentration at 218.7 ppm (95% confidence interval: 163.2 - 262.3). These toxic effects of bacterial metabolites were also proved by cytotoxicity test against Sf9 cells. Especially, benzylideneacetone, which was used as a main ingredient of 'BM+Bt', showed high cytotoxicity at its low micromolar concentration.