Toxicity and antifeedant activity of a sesquiterpene lactone from Encelia against Spodoptera littoralis

Srivastava, R. P.; Proksch, Peter; Wray, Victor

doi:10.1016/0031-9422(90)85254-d

Cited by 35 publications

(17 citation statements)

References 8 publications

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“…F. riparia seems to be related to F. macrophylla (Bohlmann et al, 1984a,b) based on the co-occurrence of prenylated flavonoids and sesquiterpene lactones of the eudesmanolide type. Similar lactones have been isolated from several genera from the Ecliptinae (Bohlmann et al, 1984b;Ciccio and Calzada, 1981;Herz and Kumar, 1979;Srivastava et al, 1990) and these findings may support the placing of Flourensia and Encelia in this subtribe.…”

Section: Resultssupporting

confidence: 51%

Constituents of two Flourensia species

et al. 2004

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Section: Resultssupporting

confidence: 51%

Constituents of two Flourensia species

et al. 2004

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“…3,4 Natural feeding deterrents belonging to plant secondary metabolites are mainly sesquiterpene * For correspondence or diterpene lactones. [5][6][7][8][9][10][11][12] The lactone ring is also present in natural compounds possessing antifungal activity. 13,14 Three general modes of action for the antifungal agents have been described: inhibition of cell wall formation by blocking β-glucane synthesis, cell membrane disruption by binding to ergosterol or inhibition of its synthesis, and inhibition of cell division by targeting the microtubule assembly, DNA, RNA or protein synthesis.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of β-aryl-γ-lactones and relationship: Structure – antifeedant and antifungal activity

et al. 2015

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Eighteen racemic β-aryl-γ -lactones derived from simple aromatic aldehydes have been obtained in the chemical synthesis. Iodolactones (5c and 6c) were synthesized from (E)-4-(benzo [d][1 ,3 ]-dioxol-5 -yl)-but-3-en-2-one (1). Reductive dehalogenation of iodolactones 5a-c and 6a-c afforded γ -ethyl-γ -lactones (7a-c, 8a-c) whereas the unsaturated lactones (9a-c, 10a-c) were obtained by dehydrohalogenation of iodolactones. All synthesized lactones were fully characterized by spectroscopic data (NMR, IR, HRMS) and subjected to the tests on the antifeedant activity towards Tribolium confusum, Trogoderma granarium and Sitophilus granaries as well to the tests on the antifungal activity towards four Fusarium species. The biological tests allowed to find some relationships between the structure and biological activity of the compounds studied. γ -Ethyl-γ -lactones 7a-c, 8a-c and unsaturated lactones 9a-c, 10a-c were usually stronger antifeedants than their parent iodolactones 5a-c and 6a-c. trans-Iodolactones 6a-c were more active than cis isomers 5a-c both in antifeedant and antifungal assays. The structure of aromatic substituent was the key factor in antifungal activity. The lactones with benzo [d][1,3]dioxole ring (5c, 6c, 7c, 8c, 9c) were the most active whereas those with unsubstituted benzene ring exhibited almost no activity.

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“…Pharmacological studies showed that I , II and their analogues possess a wide spectrum of biological activities, such as antitumour, antifungal, insect growth inhibition, insect feeding deterrent and insect larvicides . Isoalantolactone derived from I. racemosa roots has been reported for repellency (feeding/oviposition) and insecticidal activity against rice weevil, Sitophilus oryzae (L.), and ovicidal activity against maize borer, Chilo partellus (Swinhoe) …”

Section: Introductionmentioning

confidence: 99%