Chemo-enzymatic synthesis of optically active γ- and δ-decalactones and their effect on aphid probing, feeding and settling behavior

PLoS ONE

Volumn 11, Issue 1, 2016, Pages

  Boratyński, Filip ^a   Dancewicz, Katarzyna ^b   Paprocka, Marlena ^b   Gabrys̈, Beata ^b   Wawrzeńczyk, Czesław ^a  

^a WROC AW UNIVERSITY OF ENVIRONMENTAL AND LIFE SCIENCES   (Poland)

^b UNIVERSITY OF ZIELONA GÓRA   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

DECANE; DECANE 1,4 DIOL; DECANE 1,5 DIOL; DELTA DECALACTONE; GAMMA DECALACTONE; LACTONE DERIVATIVE; UNCLASSIFIED DRUG; ALCOHOL DEHYDROGENASE; INSECT REPELLENT; LACTONE; RECOMBINANT PROTEIN;

ARTICLE; CATALYSIS; CELERY CABBAGE; CONTROLLED STUDY; ENANTIOSELECTIVITY; ENZYME SYNTHESIS; FEEDING BEHAVIOR; FEMALE; HYDRODISTILLATION; MYZUS PERSICAE; NONHUMAN; PHLOEM; PLANT INSECT INTERACTION; SALIVATION; STEREOCHEMISTRY; XYLEM SAP; ANIMAL; APHID; BIOTRANSFORMATION; BRASSICA; DRUG EFFECTS; ESCHERICHIA COLI; GENE EXPRESSION; GENETICS; HORSE; METABOLISM; OPTICAL ROTATION; PARASITOLOGY; PHYSIOLOGY; STEREOISOMERISM; SYNTHESIS;

ALCOHOL DEHYDROGENASE; ANIMALS; APHIDS; BIOTRANSFORMATION; BRASSICA; ESCHERICHIA COLI; FEEDING BEHAVIOR; GENE EXPRESSION; HORSES; INSECT REPELLENTS; LACTONES; OPTICAL ROTATION; PHLOEM; RECOMBINANT PROTEINS; STEREOISOMERISM;

EID: 84954042895     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0146160     Document Type: Article

References (35)

1. Neerman M. Sesquiterpene lactones: a diverse class of compounds found in essentials oils possessing antibacterial and antifungal properties. Int J Aromatherapy 2003;13:114-120.
2. Skaltsa H, Lazari D, Panagouleas C, Georgiadou E, Garcia B, Sokovic M. Sesquiterpene lactones from Centaurea thessala and Centaurea attica. Antifungal activity. Phytochemistry 2000;55:903-908. PMID: 11140522
3. Paruch E, Ciunik Z, Nawrot J, Wawrzeńczyk C. Lactones. 9. Synthesis of terpenoid lactones active insect antifeedants. J Agr Food Chem 2000;48:4973-4977.
4. Paruch E, Nawrot J, Wawrzeńczyk C. Lactones: Part 11. Feeding-deterrent activity of some bi- and tricyclic terpenoid lactones. Pest Manag Sci 2001;57:776-780. PMID: 11561401
5. Grudniewska A, Dancewicz K, Białońska A, Wawrzeńczyk C, Gabrys̈ B. Piperitone-Derived Saturated Lactones: Synthesis and Aphid Behavior-Modifying Activity. J Agric Food Chem 2013;61:3364-3372. doi: 10.1021/jf3052219 PMID: 23477664
6. Mazur M, Gładkowski W, Podkowik M, Bania J, Nawrot J, Białońska A, et al. Lactones 43. New biologically active lactones: β-cyclocitral derivatives. Pest Manag Sci 2014;70:286-294. doi: 10.1002/ps. 3557 PMID: 23703876
7. Szczepanik M, Grudniewska A, Zawitowska B, Wawrzeńczyk C. Structure-related antifeedant activity of halolactones with a p-menthane system against the lesser mealworm, Alphitobius diaperinus Panzer. Pest Manag Sci 2014;70:953-958. doi: 10.1002/ps.3634 PMID: 24009153
8. Mori K. The Synthesis of Insect Pheromones, 1979-1989. Total Synthesis of Natural Products: John Wiley & Sons, Inc.; 2007. p. 1-521.
9. Dufosse L, Latrasse A, Spinnler H-E. Importance of lactones in food flavors: Structure, distribution, sensory properties and biosynthesis. Sci Aliments 1994;14:17-50.
10. Mosandl A, Gunther C. Stereoisomeric flavor compounds. 20. Structure and properties of γ-lactone enantiomers. J Agric Food Chem 1989;37:413-418.
11. Maga JA. Lactones in foods. Critic Rev Food Sci Nutri. 1976;8:1-56.
12. Dams I, Białońska A, Ciunik Z, Wawrzeńczyk C. Lactones. 21. Synthesis and odoriferous properties of lactones with the p-menthane system. J Agric Food Chem 2004;52:1630-1634. PMID: 15030222
13. Siek TJ, Albin IA, Sather LA, Lindsay RC. Comparison of Flavor Thresholds of Aliphatic Lactones with Those of Fatty Acids, Esters, Aldehydes, Alcohols, and Ketones. J Dairy Sci 1971;54:1-4.
14. Schrader J, Etschmann MMW, Sell D, Hilmer JM, Rabenhorst J. Applied biocatalysis for the synthesis of natural flavour compounds-current industrial processes and future prospects. Biotechnol Lett 2004;26:463-472. PMID: 15127786
15. Kishimoto N, Sugihara S, Mochida KYO, Fujita T. In Vitro Antifungal and Antiviral Activities of gamma and delta-Lactone Analogs Utilized as Food Flavoring. Biocontrol Sci 2005;10:31-36.
16. Lopez L, Morgan ED. Explanation of Bitter Taste of Venom of Ponerine Ant, Pachycondyla apicalis. J Chem Ecol 1997;23:705-712.
17. Li G, Roze U, Locke D. Warning Odor of the North American Porcupine (Erethizon dorsatum). J Chem Ecol 1997;23:2737-2754.
18. Larsson MC, Hedin J, Svensson GP, Tolasch T, Francke W. Characteristic Odor of Osmoderma eremita Identified as a Male-Released Pheromone. J Chem Ecol 2003;29:575-587. PMID: 12757320
19. James D, Petroski R, Cossé A, Zilkowski B, Bartelt R. Bioactivity, Synthesis, and Chirality of the Sex Pheromone of Currant Stem Girdler, Janus integer. J Chem Ecol 2003;29:2189-2199. PMID: 14682505
20. Svensson G, Larsson M, Hedin J. Attraction of the Larval Predator Elater ferrugineus to the Sex Pheromone of Its Prey, Osmoderma eremita, and Its Implication for Conservation Biology. J Chem Ecol 2004;30:353-363. PMID: 15112729
21. Brenna E, Fuganti C, Gatti FG, Serra S. Biocatalytic methods for the synthesis of enantioenriched odor active compounds. Chem Rev 2011;111:4036-4072. doi: 10.1021/cr100289r PMID: 21598986
22. Olejniczak T, Ciunik Z. Enantioselective hydrolysis of δ-acetoxy-γ-lactones. Tetrahedron: Asymm 2004;15:3743-3749.
23. Olejniczak T, Gawroński J, Wawrzeńczyk C. Lactones. 6. Microbial lactonization of γ, δ-epoxy esters. Chirality 2001;13:302-307. PMID: 11370019
24. Ratus̈ B, Gładkowski W, Wawrzeńczyk C. Lactones 32: New aspects of the application of Fusarium strains to production of alkylsubstituted ε-lactones. Enzyme Microb Tech 2009;45:156-163.
25. Les̈niak A, Smuga M, Białońska A, Kula J, Wawrzeńczyk C. Lactones 44. Microbial lactonization of γ-ketoacids. J Mol Catal B-Enzym 2014;106:32-39.
26. Boratyński F, Kiełbowicz G, Wawrzeńczyk C. Lactones 34 Application of alcohol dehydrogenase from horse liver (HLADH) in enantioselective synthesis of δ- and ε-lactones. J Mol Catal B-Enzym 2010;65:30-36.
27. Boratyński F, Smuga M, Wawrzeńczyk C. Lactones 42. Stereoselective enzymatic/microbial synthesis of optically active isomers of whisky lactone. Food Chem 2013;141:419-427. doi: 10.1016/j. foodchem.2013.02.106 PMID: 23768375
28. Verdaguer X, Hansen MC, Berk SC, Buchwald SL. Titanocene-catalyzed reduction of lactones to lactols. J Org Chem 1997;62:8522-8528. PMID: 11671995
29. Harrewijn P. Resistance mechanisms of plant genotypes to various aphid species. Campbell R. K. ERDe, editor. Amsterdam: Elsevier; 1990.
30. Hardie J, Holyoak M, Taylor NJ, Griffiths DC. The combination of electronic monitoring and video-assisted observations of plant penetration by aphids and behavioural effects of polygodial. Entomol Exp Appl 1992;62:233-239.
31. Pettersson J, Tjallingii WF, Hardie J. Aphids as crop pests. van Emden H. F. HRe, editor. CABI, Wallingford 2007.
32. Mayoral AM, Tjallingii WF, Castańera P. Probing behaviour of Diuraphis noxia on five cereal species with different hydroxamic acid levels. Entomol Exp Appl 1996;78:341-348.
33. Gabrys̈ B, Pawluk M. Acceptability of different species of Brassicaceae as hosts for the cabbage aphid. Entomol Exp Appl 1999;91:105-109.
34. Alvarez AE, Tjallingii WF, Garzo E, Vleeshouwers V, Dicke M, Vosman B. Location of resistance factors in the leaves of potato and wild tuber-bearing Solanum species to the aphid Myzus persicae. Entomol Exp Appl 2006;121:145-157.
35. Tjallingii WF. Salivary secretions by aphids interacting with proteins of phloem wound responses. J Exp Bot 2006;57:739-745. PMID: 16467410