A Flavanone and Two Phenolic Acids from Chrysanthemum morifolium with Phytotoxic and Insect Growth Regulating Activity (original) (raw)
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Advancement in Medicinal Plant Research, 2017
Plutella xylostella (Lepidoptera: Plutellidae) popularly known as the moth-of-crucifers is a major pest of brassica worldwide which can cause damage to brassica crops up to 100% loss of total production. The use of synthetic pesticides for its control has harmful effects on public health and the environment, besides the development of resistance to these synthetic insecticides. One of the alternative control methods developed in recent years has been the use of plant extracts. In the present study, was evaluated the insecticidal potential of the leaves, root bark and stem bark extracts of three Mozambican medicinal plants: Trichilia emetica, Anacardium occidentale and Cymbopogon citratus to control the development of diamondback moth (L.) on cabbage. The plant extracts were obtained by maceration in organic solvents (n-hexane, ethyl acetate and methanol). The preliminary phytochemical tests were conducted to identify classes of chemical constituents present in the extracts. To assess insecticidal activity, the extracts were tested on the second instar larvae of diamondback moth using the leaf disc immersion methodology, where the larvae were fed with cabbage leaves dipped in each extract, being observed larval mortality in function of extract concentration. The evaluation of the insecticidal activity showed that the methanol crude extract from the root bark of Trichilia emetica caused the highest larval mortality (LC 50 = 0.94 mg.ml-1). The LC 50 values obtained for all the extracts tested indicate that the crude methanol extracts have a higher larvicidal potential than those obtained in the sequential extraction. The results suggest that the larvicidal activity of the extracts under study can be related to the presence of the identified metabolites that act synergistically or individually in producing larval mortality.
Insect growth regulatory effects of some extracts and sterols from (Cactaceae) against and
Phytochemistry, 2005
A methanol extract from the roots and aerial parts of Myrtillocactus geometrizans (Cactaceae) yielded peniocerol 1, macdougallin 2, and chichipegenin 3. The natural products 1, 2 their mixtures, MeOH and CH 2 Cl 2 extracts showed insecticidal and insect growth regulatory activity against fall armyworm [Spodoptera frugiperda J. E. Smith (Lepidoptera: Noctuidae)], an important insect pest of corn, and [Tenebrio molitor (Coleoptera)], a pest of stored grains in Mexico. The most active compounds were 1, 2, and a mixture (M 2 ) of 1 and 2 (6:4). All these extracts, compounds and the mixture had insect growth regulating (IGR) activity between 5.0 and 50.0 ppm and insecticidal effects between 50 and 300 ppm in diets. The extracts were insecticidal to larvae, with lethal doses between 100 and 200 ppm. These compounds appear to have selective effects on the pre-emergence metabolism of Coleoptera, because in all treatments of the larvae of T. molitor, pupation were shortened and this process show precociousness in relation to controls. In contrast to S. frugiperda larvae, onset of pupation was noticeably delayed. Emergence in both cases was drastically diminished. In both pupae and in the few adults that were able to emerge, many deformations were observed. The results of these assays indicated that the compounds were more active than other known natural insect growth inhibitors such as gedunin and methanol extracts of Cedrela salvadorensis and Yucca periculosa. Peniocerol, macdougallin and chichipegenin, as well as mixtures of these substances, may be useful as natural insecticidal agents.
The potential of secondary metabolites in plant material as deterents against insect pests: A review
African Journal of Pure and Applied …, 2010
The potential of using plant material as deterrent against pest in crops, on the field and during postharvest period, is a study that is presently gaining acceptance as a result of the indiscriminate use of chemical pesticides which has given rise to many well-known problems, including genetic resistance of pest species, toxic residues in stored products, increasing costs of application, hazards from handling and environmental pollution. This paper explores the anti-feedant properties of some of these plants and also discusses the advantages and disadvantages of using anti-feedant compounds isolated from plant material.
Acta Horticulturae, 2019
Many insect pests including the diamondback moth (Plutella xylostella L.) which has a known history of developing resistance to many pesticides, are believed to be able to develop that resistance as a result of a continuous and repeated use of pesticides with similar modes of action and or active ingredients. In nature however, plants would have been extinct; but plants produce compounds with toxicity to a wide variety of potential herbivores (Bush et al., 1997). Plants under attack release a cocktail of volatile compounds that act as cues for these allies, which then attack, consume and reduce the populations of herbivores (De Moraes et al., 1998). The aim of this study was to evaluate and compare the feeding and anti-feeding effects of Azadirachta indica, Chrysanthemum cinerariifolium and Quassia amara extracts (Azadirachtin, Pyrethrin and Quassin, respectively) and their mixtures on diamondback moth larvae. Larvae were fed with cabbage leaf disks treated with the various extracts. Mortality and leaf area consumed by larvae were recorded after 24 h of larval exposure to the treated leaves. Results revealed varying level of feeding and anti-feedant effects among all the formulations. Formulations with the highest concentration resulted in an increased feeding and anti-feedant effect in terms of larval mortality and feeding area. The most effective anti-feedant effect was recorded by the Pyrethrin, and Azadirachtin + Pyrethrin mixture (with a 1.0% feeding area each), followed by Azadirachtin + Pyrethrin + Quassin mixture and Pyrethrin + Quassin mixture with 2 and 3% feeding area, respectively. Pyrethrin, Azadirachtin + Pyrethrin and Azadirachtin + Pyrethrin + Quassin extracts combinations on the other hand recorded 50, 40 and 50% total larval mortality, respectively.
Crop Protection, 2010
The effect of the whole methanol extracts of five Chrysanthemum species on feeding and performance of Spodoptera littoralis (Boisduval) larvae has been investigated in vitro. The extracts exhibited an antifeeding and phagostimulating activities against cotton leafworm larvae when applied either on leaf discs or incorporated into an artificial diet. Under chosen conditions, the antifeedant index calculated over 24 h for sixth instar larvae significantly varied from 78.55 for Chrysanthemum segetum L. to À44.18 for Chrysanthemum fuscatum Desf. at the dose of 1000 ppm. Toxicity of the extracts was manifested by a high mortality, reduced growth rates, and low weight gain by larvae fed on diets containing 1000e10,000 ppm of the extract. Anyone of the larvae treated with Chrysanthemum macrotum (D.R.) Ball. leaves crude extract survived to pupation at the two higher concentrations. The time to pupation increased for Chrysanthemum grandiflorum flowers crude extract from 11.40 AE 0.93 to 28.93 AE 10.92 days as the extract concentration in the diet increased from 0 to 10,000 ppm. The ingestion of crude extract by the third instar larvae reduced significantly the consumption, growth and utilisation of the ingested and digested food, and reduced digestibility.
Crop Protection, 2012
We investigated the feeding deterrent effects and toxicity of naturally occurring and synthetic quinones to the cabbage looper, Trichoplusia ni. Feeding deterrent effects were determined via a leaf disc choice bioassay. Based on DC 50 values, 1,4-naphthoquinone was the most active antifeedant (DC 50 ¼ 1.8 mg/cm 2) followed by juglone (DC 50 ¼ 2.1 mg/cm 2), 2-methoxy-1,4-naphthoquinone (DC 50 ¼ 2.6 mg/cm 2), plumbagin (DC 50 ¼ 3.3 mg/cm 2), and 2,3-dimethoxy-5-mehtyl-1,4-benzoquinone (DC 50 ¼ 4.2 mg/cm 2) in third instar cabbage looper larvae. 2-Bromo-1,4-naphthoquinone, 2-chloro-3-morpholino-1,4-naphthoquinone, 1,8dihydroxy-anthraquinone, 2-methyl-1,4-naphthoquinone and naphthazarin had DC 50 values ranging from 8.4 to 10.1 mg/cm 2. Juglone and plumbagin were able to provide protection to intact cabbage plants in a greenhouse experiment. Cabbage looper larvae consumed less leaf area and weighed less on cabbage plants treated with either of these naturally occurring quinones. Most of the quinones demonstrated levels of antifeedant activity greater than neem, a positive control, in laboratory bioassays. The level of activity for juglone was comparable to neem in the greenhouse experiment. There was also a reduction in the number of larvae on treated plants compared with the negative control. Structure-activity relationships suggest that the antifeedant effects of the tested quinones depend on the number and position of hydroxyl and methoxyl substituents of quinones. Most of the quinones were of medium-low toxicity to third instar cabbage looper larvae via topical administration. Some of these quinones could have potential for development as commercial insect control agents targeting the feeding behavior of insects with minimal toxicity, provided that their impacts on non-target organisms and environment are minimal.
Effect of plant secondary metabolites on legume pod borer, Helicoverpa armigera
Journal of Pest Science, 2013
The effect of various flavonoids, lectins and phenyl b-D-glucoside on larval survival, weights and the activities of digestive (total serine protease and trypsin) and detoxifying [esterase and glutathione-S-transferase] enzymes of Helicoverpa armigera larvae at 5 and 10 days after treatment (DAT) was studied through diet incorporation assay. Flavonoids (quercetin, cinnamic acid, caffeic acid, chlorogenic acid, catechin, trihydroxyflavone, gentisic acid, ferulic acid, protocatechuic acid and umbelliferone) were incorporated in artificial diet at 100, 500 and 1000 ppm, lectins: groundnut leaf lectin (GLL), concavalin (ConA) and phenyl b-D-glucoside at 2.5 and 5 lg mL-1. Flavonoids such as chlorogenic acid, caffeic acid and protocatechuic acid at 1,000 ppm were more toxic to H. armigera larvae at 10 DAT than quercetin, catechin, cinnamic acid, trihydroxyflavone, gentisic acid, ferulic acid and umbelliferone. Larval growth and development were significantly reduced in H. armigera larvae fed on a diet with GLL and ConA at 5 lg mL-1 compared to the larvae fed at 2.5 and 1.25 lg mL-1 concentrations. The enzyme activities of the larvae were significantly reduced in flavonoid-treated diets. The flavonoids such as chlorogenic acid, caffeic acid, gentisic acid, trihydroxyflavone, catechin and protocatechuic acid, and lectins, GLL and ConA can be utilized in insect control programs.
Effect of plant secondary metabolites on legume pod borer
The effect of various flavonoids, lectins and phenyl b-D-glucoside on larval survival, weights and the activities of digestive (total serine protease and trypsin) and detoxifying [esterase and glutathione-S-transferase] enzymes of Helicoverpa armigera larvae at 5 and 10 days after treatment (DAT) was studied through diet incorporation assay. Flavonoids (quercetin, cinnamic acid, caffeic acid, chlorogenic acid, catechin, trihydroxyflavone, gentisic acid, ferulic acid, protocatechuic acid and umbelliferone) were incorporated in artificial diet at 100, 500 and 1000 ppm, lectins: groundnut leaf lectin (GLL), concavalin (ConA) and phenyl b-D-glucoside at 2.5 and 5 lg mL-1. Flavonoids such as chlorogenic acid, caffeic acid and protocatechuic acid at 1,000 ppm were more toxic to H. armigera larvae at 10 DAT than quercetin, catechin, cinnamic acid, trihydroxyflavone, gentisic acid, ferulic acid and umbelliferone. Larval growth and development were significantly reduced in H. armigera larvae fed on a diet with GLL and ConA at 5 lg mL-1 compared to the larvae fed at 2.5 and 1.25 lg mL-1 concentrations. The enzyme activities of the larvae were significantly reduced in flavonoid-treated diets. The flavonoids such as chlorogenic acid, caffeic acid, gentisic acid, trihydroxyflavone, catechin and protocatechuic acid, and lectins, GLL and ConA can be utilized in insect control programs.
Insecticidal properties and chemical constitution
1947
IN Part ix it was shown that the methyl ethers of some of the simpler flavones are markedly toxic to fish. They have in them the characteristic toxophorc -CO-C=C--O--also found in rotenone. Results recorded by previous I I workexs relating to the simpler coumarins baving the toxophore --C=C-CO--O-suggest that they are comparatively feeble. Spath' foutnd I~ that 175-5 mg. of 4-methyl umbelliferone and 63-7 mg. of 7-ethoxy coumarin per litre of water were necessary for causing death of fish in 8 hours. The more potent among the compounds studied by hito contain also furan rings and other complications. Later Mahal 3 noted that 4-methyl umbelliferone does not possess appreciable anthelmintic properties. Again I.~uger et al. s, though they have not presented details, have reported tbat the simpler coumarins have only weak insecticidal properti› They observed very good strength only in the case of 4-hydroxy coumarins with a carbonyl substituent in the 3-position (I):
International Journal of Tropical Insect Science, 2020
Screening the biological activities of plant secondary metabolites on economic pests can lead to discovery new ecofriendly biopesticides. The aim of this work was to evaluate the antifeedant, growth inhibitory and toxic activities of seven monoterpenes, two phenylpropenes and two sesquiterpenes on 2nd larval instar of Spodoptera littoralis. The tested compounds induced a significant antifeedant effect at various concentrations (500, 1000 and 2000 mg/kg), particularly after 6 and 9 days of exposure. Among the tested compounds, trans-cinnamaldehyde, α-terpinene, (−)-citronellal and 1,8-cineole were the most potent antifeedants after the three exposure periods. In general the tested compounds showed remarkable antifeedant activity after 9 days of exposure as their antifeedant indices ranged between 44.0 and 80.1%. On the other hand, the tested compounds drastically inhibited the growth of S. littoralis larvae at the tested concentrations. The larval growth inhibition ranged between 21.4 and 100% with cuminaldehyde, 1,8-cineole and eugenol being the most potent growth inhibitors. Some of the tested compounds caused significantly higher antifeedant and growth inhibitory effects than a reference insecticide, pyriproxifen. In general, the tested compounds showed higher growth inhibition than antifeedant effect. The tested compound also induced S. littoralis larval morality which improved with increasing exposure time and concentration. Cuminaldehyde, 1,8-cineole and (−)-carvone showed highest toxicity with 100.0, 97.0 and 77.0% mortality, respectively, at 2000 mg/kg after 9 days of exposure. Biochemical studies revealed that trans-cinnamaldehyde (IC 50 = 0.03 mM), farnesol (IC 50 = 0.04 mM) and eugenol (IC 50 = 0.06 mM) are potent α-amylase inhibitors. These three compounds also caused significant inhibition of total proteases activity. This is the first report on antifeedant, growth inhibitory and insecticidal activities of the tested compounds on S. littoralis. Moreover, the strong bioactivity reported in this study indicated that these compounds have a potential to be used as bioinsecticides.