Larvicidal activity of isobutylamides identified in Piper nigrum fruits against three mosquito species
26 Feb 2002-Journal of Agricultural and Food Chemistry (American Chemical Society)-Vol. 50, Iss: 7, pp 1866-1870
TL;DR: Structural-activity relationships indicate that the N-isobutylamine moiety might play a crucial role in the larvicidal activity, but the methylenedioxyphenyl moiety does not appear essential for toxicity.
Abstract: The insecticidal activity of materials derived from the fruits of Piper nigrum against third instar larvae of Culex pipiens pallens, Aedes aegypti, and A. togoi was examined and compared with that of commercially available piperine, a known insecticidal compound from Piper species. The biologically active constituents of P. nigrum fruits were characterized as the isobutylamide alkaloids pellitorine, guineensine, pipercide, and retrofractamide A by spectroscopic analysis. Retrofractamide A was isolated from P. nigrum fruits as a new insecticidal principle. On the basis of 48-h LC(50) values, the compound most toxic to C. pipiens pallens larvae was pipercide (0.004 ppm) followed by retrofractamide A (0.028 ppm), guineensine (0.17 ppm), and pellitorine (0.86 ppm). Piperine (3.21 ppm) was least toxic. Against A. aegypti larvae, larvicidal activity was more pronounced in retrofractamide A (0.039 ppm) than in pipercide (0.1 ppm), guineensine (0.89 ppm), and pellitorine (0.92 ppm). Piperine (5.1 ppm) was relatively ineffective. Against A. togoi larvae, retrofractamide A (0.01 ppm) was much more effective, compared with pipercide (0.26 ppm), pellitorine (0.71 ppm), and guineensine (0.75 ppm). Again, very low activity was observed with piperine (4.6 ppm). Structure-activity relationships indicate that the N-isobutylamine moiety might play a crucial role in the larvicidal activity, but the methylenedioxyphenyl moiety does not appear essential for toxicity. Naturally occurring Piper fruit-derived compounds merit further study as potential mosquito larval control agents or as lead compounds.
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TL;DR: The current state of knowledge on larvicidal plant species, extraction processes, growth and reproduction inhibiting phytochemicals, botanical ovicides, synergistic, additive and antagonistic joint action effects of mixtures, residual capacity, effects on non-target organisms, resistance, screening methodologies, and discuss promising advances made in phytochemical research are reviewed.
579 citations
Cites background from "Larvicidal activity of isobutylamid..."
...(48 h exposure) Fruit Methanol extract containing: Park et al. (2002)...
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...pipiens pallens larvae by Park et al. (2002). These low doses are comparable to many synthetic insecticides....
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Journal Article•
TL;DR: The study reveals that the consumption of these spices would exert several beneficial effects by virtue of their antioxidant activity, followed in descending order by green tea, black tea, and Elettaria cardamomum.
Abstract: The methanolic crude extracts of some commonly used medicinal plants were screened for their free radical scavenging properties using ascorbic acid as standard antioxidant. Free radical scavenging activity was evaluated using 1,1-diphenyl-2-picryl-hydrazyl (DPPH) free radical. The overall antioxidant activity of green tea (Camellia sinensis Linn.) was the strongest, followed in descending order by black tea (Camellia sinensis Linn.), Eugenia caryophyllus (Spreng.) Bullock and Harrison, Piper cubeba Linn., Zingiber officinale Roscoe and Piper nigrum Linn. Trigonella foenum graecum Linn. and Elettaria cardamomum (Linn.) Maton showed weak free radical scavenging activity with the DPPH method. All the methanolic extracts exhibited antioxidant activity significantly. The IC50 of the methanolic extracts ranged between 6.7 ± 0.1 and 681.5 ± 8.4 µg/ml and that of ascorbic acid was 8.9 ± 0.1 µg/ml. The study reveals that the consumption of these spices would exert several beneficial effects by virtue of their antioxidant activity.
353 citations
Cites background from "Larvicidal activity of isobutylamid..."
...Antimicrobial (6), larvicidal (7) and anti-cancer (8) activities of Piper nigrum Linn....
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03 May 2007-Journal of Environmental Science and Health Part B-pesticides Food Contaminants and Agricultural Wastes
TL;DR: A multi-dimensional approach that exerts control on all the life stages of house fly, but simultaneously preserves the fly's natural enemies could be an ecologically sustainable way of maintaining the fly populations below maximally acceptable limits.
Abstract: Musca domestica L. (Diptera: Muscidae), commonly called the house fly, is a major domestic, medical and veterinary pest that causes irritation, spoils food and acts as a vector for many pathogenic organisms. In this paper, the social and health problems related to housefly are introduced with the associated need to control its population. Physical and chemical methods of house fly control are briefly discussed. The main focus of this review is on the biological control methods for house fly control, that comprise botanical, fungal, bacterial and parasitoid agents. Although several biocontrol agents are still in the nascent stage, some of them (especially fungal and parasitoid agents) have shown reliable field performance and seem to be suitable candidates for commercialization. However, the majority of these laboratory and field studies have been conducted in the temperate region. It remains to be seen whether the application of biocontrol agents would be feasible in tropical environments. The integrated pest management practices, which can provide more reliable field performance, have also been discussed. A multi-dimensional approach that exerts control on all the life stages of house fly, but simultaneously preserves the fly's natural enemies could be an ecologically sustainable way of maintaining the fly populations below maximally acceptable limits.
211 citations
TL;DR: Results of this study show that the petroleum ether extract of A. indicum may be considered as a potent source and β-sitosterol as a new natural mosquito larvicidal agent.
Abstract: Larvicidal activity of crude hexane, ethyl acetate, petroleum ether, acetone and methanol extracts of five medicinal plants, Abutilon indicum, Aegle marmelos, Euphorbia thymifolia, Jatropha gossypifolia and Solanum torvum were assayed for their toxicity against the early fourth-instar larvae of Culex quinquefasciatus. The larval mortality was observed after 24 h exposure. All extracts showed moderate larvicidal effects; however, the highest larval mortality was found in petroleum ether extract of A. indicum. In the present study, bioassay-guided fractionation of A. indicum led to the separation and identification of a β-sitosterol as a potential new mosquito larvicidal compound with LC50 value of 11.49, 3.58 and 26.67 ppm against Aedes aegypti L, Anopheles stephensi Liston and C. quinquefasciatus Say (Diptera: Culicidae), respectively. 1H NMR, 13C NMR and mass spectral data confirmed the identification of the active compound. β-sitosterol has been recognized as the active ingredient of many medicinal plant extracts. All the crude extracts when screened for their larvicidal activities indicated toxicity against the larvae of C. quinquefasciatus. This article reports the isolation and identification of the β-sitosterol as well as bioassay data for the crude extracts. There are no reports of β-sitosterol in the genus A. indicum, and their larvicidal activities are being evaluated for the first time. Results of this study show that the petroleum ether extract of A. indicum may be considered as a potent source and β-sitosterol as a new natural mosquito larvicidal agent.
204 citations
Cites background from "Larvicidal activity of isobutylamid..."
...Park et al. (2002) have also reported the compounds retrofractamide A (0.039 ppm), pipercide (0.1 ppm), guineensine (0.89 ppm), pellitorine (0.92 ppm) and Piperine (5.1 ppm) derived from the fruits of P. nigrum against A. aegypti thirdinstar larvae....
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...Park et al. (2002) have also reported the compounds retrofractamide A (0.039 ppm), pipercide (0.1 ppm), guineensine (0.89 ppm), pellitorine (0.92 ppm) and Piperine (5.1 ppm) derived from the fruits of P. nigrum against A. aegypti thirdinstar larvae....
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TL;DR: This review covers the huge amount of literature available on plant extracts tested as mosquito larvicides, particularly aqueous and alcoholic ones, due to their easy formulation in water without using surfactants, and concludes that 29 of them have outstanding larvicidal activity against major vectors belonging to the genera Anopheles, Aedes and Culex.
144 citations
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TL;DR: In this article, two unsaturated amides, retrofractamides A and C, were isolated from the total aboveground parts of Piper retroractum and were shown to be N -isobutyl-9(3′,4′-methylenedioxyphenyl)2 E,4 E,8 E -nonatrienamide from spectroscopic and chemical investigations.
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TL;DR: Extracts of ground black pepper were highly toxic to adult Anthonomus grandis Boheman when they were applied topically to the 3- to 5-day-old insects.
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