Hostname: page-component-8448b6f56d-gtxcr Total loading time: 0 Render date: 2024-04-24T03:32:07.682Z Has data issue: false hasContentIssue false

Deterrent activity of hops flavonoids and their derivatives against stored product pests

Published online by Cambridge University Press:  16 February 2017

J. Jackowski*
Affiliation:
Department of Plant Protection, Wrocław University of Environmental and Life Sciences, pl. Grunwaldzki 24a, 53-363 Wrocław, Poland
J. Popłoński
Affiliation:
Department of Chemistry, Wrocław University of Environmental and Life Sciences, ul. Norwida 25, 50-375 Wrocław, Poland
K. Twardowska
Affiliation:
Department of Plant Protection, Wrocław University of Environmental and Life Sciences, pl. Grunwaldzki 24a, 53-363 Wrocław, Poland
J. Magiera-Dulewicz
Affiliation:
Department of Plant Protection, Wrocław University of Environmental and Life Sciences, pl. Grunwaldzki 24a, 53-363 Wrocław, Poland
M. Hurej
Affiliation:
Department of Plant Protection, Wrocław University of Environmental and Life Sciences, pl. Grunwaldzki 24a, 53-363 Wrocław, Poland
E. Huszcza
Affiliation:
Department of Chemistry, Wrocław University of Environmental and Life Sciences, ul. Norwida 25, 50-375 Wrocław, Poland
*
*Author for correspondence Phone: +48713201693 E-mail: jacek.jackowski@up.wroc.pl

Abstract

Five flavonoids from hops, two of their derivatives, along with naringenin used as a model compound, were tested for their antifeedant activity against three coleopteran stored product pests: Sitophilus granarius L., Tribolium confusum Duv. and Trogoderma granarium Everts. The introduction, into the tested flavonoid molecules, of additional structural fragments such as prenyl or dimethylpyran moiety, is proposed to significantly alter the deterrent activity of the compounds. The prenyl moiety in flavonoids increased the deterrent activity of these compounds in all three of the grain feeding species used in the tests. It is also concluded that the introduction of dimethylpyran moiety to the flavonoid structure increases its deterrent activity in S. granarius and T. confusum, but in one of the test insects, T. granarium, an increased feeding was observed in response to the introduction of dimethylpyran moiety to the flavonoid structure.

Type
Research Papers
Copyright
Copyright © Cambridge University Press 2017 

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

Bartmańska, A., Huszcza, E. & Tronina, T. (2009) Transformations of isoxanthohumol by fungi. Journal of Molecular Catalysis B: Enzymatic 61, 221244.Google Scholar
Buśko, M., Góral, T., Ostrowska, A., Matysiak, A., Walentyn-Góral, D. & Perkowski, J. (2014) The effect of Fusarium inoculation and fungicide application on concentrations of flavonoids (apigenin, kaempferol, luteolin, naringenin, quercetin, rutin, vitexin) in winter wheat cultivars. American Journal of Plant Sciences 5, 37273736.CrossRefGoogle Scholar
Chadwick, L.R., Nikolic, D., Burdette, J.E., Overk, C.R., Bolton, J.L., Van Breemen, R.B., Frolich, R., Fong, H.H.S., Farnsworth, N.R. & Pauli, G.F. (2004) Estrogens and congeners from spent hops (Humulus lupulus). Journal of Natural Products 67, 20242032.Google Scholar
Chadwick, L.R., Pauli, G.F. & Farnsworth, N.R. (2006) The pharmacogonosy of Humulus lupulus L. (hops) with an emphasis on estrogenic properties. Phytomedicine 13, 119131.Google Scholar
Etteldorf, N., Etteldorf, N. & Becker, H. (1999) New chalcones from Hop, Humulus lupulus L. Z. Naturforsch. C 54, 610612.Google Scholar
Jackowski, J., Hurej, M., Rój, E., Popłoński, J., Kośny, L. & Huszcza, E. (2015) Antifeedant activity of xanthohumol and supercritical carbon dioxide extract of spent hops against stored product pests. Bulletin of Entomological Research 105, 456461. doi: 10.1017/S0007485315000255.Google Scholar
Lane, G.A., Sutherland, O.R.W. & Skipp, R.A. (1987) Isoflavonoids as insect feeding deterents and antifungal components from root of Lupinus augustifolius . Journal of Chemical Ecology 13, 771783.Google Scholar
Morimoto, M., Kumeda, S. & Komai, K. (2000) Insect antifeedant flavonoids from Gnaphalium affine D. Don. Journal of Agricultural and Food Chemistry 48, 18881891.Google Scholar
Nawrot, J. & Harmatha, J. (2002) Insect feeding deterrent activity of lignans and related phenylpropanoids with a methylenedioxyphenyl (piperonyl) structure moiety. Entomologia Experimentalis et Applicata 104, 5160.Google Scholar
Nawrot, J., Harmatha, J., Kostova, I. & Novotny, L. (1984) Insect feeding deterrent activity of bisabolangelone and of some sesquiterpenes of eremophilane type. Biochemical Systematics and Ecology 12, 99101.Google Scholar
Nawrot, J., Bloszyk, E., Harmatha, J., Novotny, L. & Drozdz, B. (1986) Action of antifeedants of plant origin on beetles infesting stored products. Acta Entomologica Bohemslovaca 83, 327335.Google Scholar
Nawrot, J., Harmatha, J., Kostova, I. & Ognyanov, I. (1989) Antifeeding activity of rotenone and some derivatives towards selected insect storage pests. Biochemical Systematics and Ecology 17, 5557.Google Scholar
Nawrot, J., Dams, I. & Wawrzeńczyk, Cz. (2009) Feeding deterrent activity of terpenoid lactones with a p-menthane system against stored-product pests. Journal of Stored Products Research 45, 221225.Google Scholar
Ndoile, M.M. & Van Heerden, F.R. (2013) Total synthesis of ochnaflavone. Beilstein Journal of Organic Chemistry 9, 13461351.Google Scholar
Ohmura, W., Doi, S., Aoyama, M. & Ohara, S. (2000) Antifeedant activity of flavonoids and related compounds against the subterranean termite Coptotermes formosanus Shiraki. Journal of Wood Science 46, 149153.Google Scholar
Popłoński, J., Sordon, S., Tronina, T. & Huszcza, E. (2014) Selective hydrogenation of xnanthohumol to α,β-dihydroxanthohumol. Przemysł Chemiczny 93, 19161918.Google Scholar
Schoonhoven, L.M., Van Loon, J.J.A. & Dicke, M. (2012) Host-plant selection: variation is the rule. pp. 217218 in Insect-Plant Biology, 2nd edn. Oxford University Press.Google Scholar
Simmonds, M.S.J. (2001) Importance of flavonoids in insect-plant interactions: feeding and oviposition. Phytochemistry 56, 245252.CrossRefGoogle ScholarPubMed
Simmonds, M.S.J., Blaney, W.M., Delle Monache, F. & Marini Bettolo, G.B. (1990) Insect antifeedant activity associated with compounds isolated from species of Lonchocarpus and Tephrosia . Journal of Chemical Ecology 16, No. 2, 365379.Google Scholar
Stevens, J.F., Ivanic, M., Hsu, V.L. & Deinzer, M.L. (1997) Prenylflavonoids from Humulus lupulus . Phytochemistry 44, 15751585.Google Scholar
Stevens, J.F., Taylor, A.W., Nickerson, G.B., Ivancic, M., Henning, J., Haunold, A. & Deinzer, M.L. (2000). Prenylflavonoid variation in Humulus lupulus: distribution and taxonomic significance of xanthogalenol and 4′-O-methylxanthohumol. Phytochemistry 53, 759775.Google Scholar
Stompor, M., Dancewicz, K., Gabryś, B. & Anioł, M. (2015) Insect antifeedant potential of xanthohumol, isoxnathohumol, and their derivatives. Journal of Agricultural and Food Chemistry 63, 67496756.Google Scholar
Verzele, M., Stockx, J., Fontijn, F. & Anteunis, M. (1957) Xanthohumol, a new natural chalcone. Bulletin des Sociétés Chimiques Belges 66, 452475.CrossRefGoogle Scholar
Vogel, S. & Heilmann, J. (2008) Synthesis, cytotoxicity and antioxidative activity of minor prenylated chalcones from Humulus lupulus . Journal of Natural Products 71, 12371241.Google Scholar
Supplementary material: File

Jackowski supplementary material

Jackowski supplementary material 1

Download Jackowski supplementary material(File)
File 3.9 MB