Lactones 43. New biologically active lactones: β-cyclocitral derivatives

Pest Management Science

Volumn 70, Issue 2, 2014, Pages 286-294

  Mazur, Marcelina ^a   Gładkowski, Witold ^a   Podkowik, Magdalena ^a   Bania, Jacek ^a   Nawrot, Jan ^b   Białońska, Agata ^c   Wawrzeńczyk, Czesław ^a  

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

^b INSTITUTE OF PLANT PROTECTION NATIONAL RESEARCH INSTITUTE   (Poland)

^c UNIVERSITY OF WROC AW   (Poland)

Author keywords

Antibacterial compound; Antifeedant activity; Feeding deterents; Lactones; Synthesis

Indexed keywords

ADULT; ANTIFEEDANT; BACTERIUM; BEETLE; BIOACTIVITY; ESTER; FOOD STORAGE; HALOGEN; LARVA;

BACTERIA (MICROORGANISMS); COLEOPTERA; HEXAPODA; LISTERIA MONOCYTOGENES; SITOPHILUS GRANARIUS; STAPHYLOCOCCUS AUREUS; TRIBOLIUM CONFUSUM; TROGODERMA GRANARIUM;

ALDEHYDE; ANTIINFECTIVE AGENT; BETA CYCLOCITRAL; BETA-CYCLOCITRAL; DITERPENE; LACTONE;

ANIMAL; ANTIBACTERIAL COMPOUND; ANTIFEEDANT ACTIVITY; ARTICLE; BACTERIUM; BEETLE; CHEMISTRY; DRUG EFFECT; FEEDING BEHAVIOR; FEEDING DETERENTS; INSECT CONTROL; ODOR; SYNTHESIS; WEEVIL;

ANTIBACTERIAL COMPOUND; ANTIFEEDANT ACTIVITY; FEEDING DETERENTS; LACTONES; SYNTHESIS;

ALDEHYDES; ANIMALS; ANTI-BACTERIAL AGENTS; BACTERIA; BEETLES; DITERPENES; FEEDING BEHAVIOR; INSECT CONTROL; LACTONES; ODORS; WEEVILS;

EID: 84892486640     PISSN: 1526498X     EISSN: 15264998     Source Type: Journal    
DOI: 10.1002/ps.3557     Document Type: Article

References (33)

1. Begum K, Reddy PV, Leelaja BC, Rajashekar Y and Rajendran S, Studies on insect infestation in chocolates. J Stored Prod Res 43:118-122 (2007).
2. Mewis II and Ulrichs C, Action of amorphous diatomaceous earth against different stages of the stored product pests Tribolium confusum, Tenebrio molitor, Sitophilus granarius and Plodia interpunctella. J Stored Prod Res 37:153-164 (2001).
3. Wakefield ME, Bryning G and Chambers PJ, Progress towards a lure to attract three stored product weevils, Sitophilus zeamais Motschulsky, S. oryzae (L.) and S. granaries (L.) (Cleoptera: Curculioniadae). J Stored Prod Res 41:145-161 (2005).
4. Ramaswamy V, Cresence VM, Rejitha JS, Lekshmi MU, Dharsana KS, Prasad SP, et al., Listeria-review of epidemiology and pathogenesis. J Microbiol Immunol Infect 40:4-13 (2007).
5. Kang CI, Song JH, Chung DR, Peck KR, Ko KS, Yeom JS, et al., Clinical impact of methicillin resistance on outcome of patients with Staphylococcus aureus infection: A stratified analysis according to underlying diseases and sites of infection in a large prospective cohort. J Infect 61:299-306 (2010).
6. Yokoe H, Yoshida M and Shishido K, Total synthesis of (-)-xanthatin. Tetrahedron Lett 49:3504-3506 (2008).
7. Antane S, Caufield CE, Hu W, Keeney D, Labthavikul P, Morris K, et al., Pulvinones as bacterial cell wall biosynthesis inhibitors. Bioorg Med Chem Lett 16:176-180 (2006).
8. Kalkhambkar RG, Kulkarni GM, Kamanavalli CM, Premkumar N, Asdaq B and Sun CM, Synthesis and biological activities of some new fluorinated coumarins and 1-aza coumarins. Eur J Med Chem 43:2178-2188 (2008).
9. Barrero AF, Oltra JE, Álvarez M, Raslan DS, Saúde DA and Akssira M, New sources and antifungal activity of sesquiterpene lactones. Fitoterapia 71:60-64 (2000).
10. Kumar R, Saha A and Saha DA, New antifungal coumarin from Clausena excavata. Fitoterapia 83:230-233(2012).
11. Pillay P, Vleggaar R, Maharaj VJ, Smith PJ and Lategan CA, Isolation and identification of antiplasmodial sesquiterpene lactones from Oncosiphon piluliferum. J Ethnopharmacol 112:71-76 (2007).
12. Graziose R, Rathinasabapathy T, Lategan C, Poulev A, Smith PJ, Grace M, et al., Antiplasmodial activity of aporphine alkaloids and sesquiterpene lactones from Liriodendron tulipifera L. J Ethnopharmacol 133:26-30 (2011).
13. León LG, Machín RP, Rodríguez CM, Ravelo JL, Martín VS and Padrón JM, γ-Lactones, α, β- and β, γ-fused to carbocycles as novel antiproliferative drugs. Bioorg Med Chem Lett 18:5171-5173 (2008).
14. Tantithanaporn S, Wattanapiromsakul C, Itharat A and Keawpradub N, Cytotoxic activity of acetogenins and styryl lactones isolated from Goniothalamus undulatus Ridl. root extracts against a lung cancer cell line (COR-L23). Phytomedicine 18:486-490 (2011).
15. Taylor PG, Dupuy Loo OA, Bonilla JA and Murillo R, Anticancer activities of two sesquiterpene lactones, millerenolide and thieleanin isolated from Viguiera sylvatica and Decachaeta thieleana. Fitoterapia 79:428-432 (2008).
16. Boratyński F, Smuga M and Wawrzeńczyk C, Lactones 42. Stereoselective enzymatic/microbialsynthesis of optically active isomers of whisky lactone. Food Chem 141:419-427 (2013).
17. Nawrot J, Dams I and Wawrzeńczyk C, Feeding deterrent activity of terpenoid lactones with a p-menthane system against stored-product pests. J Stored Prod Res 45:221-225 (2009).
18. Szczepanik M, Dams I and Wawrzeńczyk C, Feeding deterrent activity of terpenoid lactones with the p-menthane system against the Colorado potato beetle (Coleoptera: Chrysomelidae). Environ Entomol 34:1433-1440 (2005).
19. Paruch E, Nawrot J and Wawrzeńczyk C, Lactones: Part 11. Feeding-deterrent activity of some bi- and tricyclic terpenoid lactones. Pest Manag Sci 57:776-780 (2001).
20. Wawrzeńczyk C, Dams I, Szumny A, Szczepanik M, Nawrot J, Pradzyñska A, et al., Synthesis and evaluation of antifeedant, antifungal and antibacterial activity of isoprenoid lactones. J Environ Stud 14:69-84 (2005).
21. Gliszczynska A, Switalska M, Wietrzyk J and Wawrzenczyk C, Synthesis of a natural gamma-butyrolactone from nerylacetone by Acremonium roseum and Fusarium oxysporum cultures. Nat Prod Commun 6:367-370 (2011).
22. CrysAlis 'RED', O. D. L., Abingdon, UK (2009).
23. Clark RC and Reid JS, The analytical calculation of absorption in multifaceted crystals. Acta Crystallogr A 51:887-897 (1995).
24. Sheldrick GM, A short history of SHELX. Acta Crystallogr A 64:112-122 (2008).
25. Crombie BS, Smith C, Varnavas CZ and Wallace TW, A conjugate addition-radical cyclisation approach to sesquiterpene-phenol natural products. J Chem Soc Perkin Trans 1 206-215 (2001).
26. Srikrishna A and Krishnan K, Synthesis of (+/-)-thaps-7(15)-ene and (+/-)-thaps-6-enes. J Chem Soc Perkin Trans 1 667-673 (1993).
27. Jones GB, Huber RS and Chau S, The Claisen rearrangement in synthesis: acceleration of the Johnson orthoester protocol en route to bicyclic lactones. Tetrahedron 49:369-380 (1993).
28. Srikrishna A and Anebouselvy K, An enantiospecific approach to tricyclic sesquiterpenes mayurone and thujopsenes. 1. J Org Chem 66:7102-7106 (2001).
29. 13C NMR spectrometry, in Spectrometric Identification of Organic Compounds, 4th edition. John Wiley & Sons, Chichester, p. 267 (1980).
30. Rivero-Cruz JF, Antimicrobial compounds isolated from Haematoxylon brasiletto. J Ethnopharmacol 119:99-103 (2008).
31. Xia Z, Qu W, Lu H, Fu J, Ren Y and Liang J, Sesquiterpene lactones from Sonchus arvensis L. and their antibacterial activity against Streptococcus mutans ATCC 25175. Fitoterapia 81:424-428 (2010).
32. Fischer NH, Lu T, Cantrell CL, Castañeda-Acosta J, Quijano L and Franzblau SG, Antimycobacterial evaluation of germacranolides: in honour of Professor G.H. Neil Towers' 75th birthday. Phytochemistry 49:559-564 (1998).
33. Yang R, Li C, Lin Y, Peng G, She Z and Zhou S, Lactones from a brown alga endophytic fungus (No. ZZF36) from the South China Sea and their antimicrobial activities. Bioorg Med Chem Lett 16:4205-4208 (2006).