Isolation, characterisation and some synthesis studies on insecticidal natural products from Sri Lankan plants (original) (raw)
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SHORT REPORT Potent Insecticidal Secondary Metabolites from the Medicinal Plant Acanthus montanus
Records of Natural Products
Acanthus montanus (Nees) T. Anders. (Family: Acanthaceae) is a small shrub with sparse branches and soft stems, widespread in Africa, the Balkans, Romania, Greece and Eastern Mediterranean. Documented evidence showed that the leaves of the plant possess spasmolytic, analgesic, anti-inflammatory and antipyretic activities. In our ongoing research project; aimed at identifying new natural compounds with insecticidal activity, the alcohol extract of the aerial parts of A. montanus exhibited a significant activity against adult Aedes aegypti. Phytochemical study of the plant has resulted in isolation of nine compounds, eight of which exhibit variable degrees of insecticidal activity. β-sitosterol-3-O-β -D-glucoside (1) exhibited potent mosquitocidal activity (100% mortality) against adult Aedes aegypti at 1.25 µg/mg concentration, followed by palmitic acid (2) (90%), linaroside (3) (80%), and acetoside (9) (70%) respectively. It is noteworthy that this is the first report of insecticidal activity of β-sitosterol-3-O-β -D-glucoside, linaroside and acetoside.
Insecticidal activity of some medicinal plants of Sri Lanka
Journal of the National Science Foundation of Sri Lanka, 2012
A wide range of solvent extracts prepared from different parts of Sri Lankan medicinal plants (101 extracts from 55 plants) were evaluated for insecticidal activity on the groundnut aphid, Aphis craccivora Koch. and the diamond back moth, Plutella xylostella (L). O f the 94 plant extracts tested for insecticidal activity againstAphis craccivora Koch., Celtiscinnamomea, Cestrum aunmticum, Costusspecious, Curcumazedoaria, Hortoniaangustifolia Ocimum gratissimum, Pleiospermium alatum and Zingiber zerumbet reported significantly high mortality (56-90%). O f the 23 extracts tested for activity against P. xylostella, only Cestrum aurantiacum, Hortonia angustifolia, Pleiospermium alatum, Curcuma zedoaria showed insecticidal activity, low pupation, adult emergence and anti-feedant activity.
Bioprospecting insecticidal compounds from plants native to Mato Grosso do Sul, Brazil
Acta Botanica Brasilica, 2008
RESUMO -(Bioprospecção de substâncias inseticidas de plantas nativas de Mato Grosso do Sul, Brasil). No presente trabalho foi avaliada a atividade inseticida de extratos de limbos foliares de Tapirira guianensis Aubl. (Anacardiaceae), Attalea phalerata (Mart. ex Spreng.) Burret (Arecaceae), Eugenia uniflora L. (Myrtaceae) e Gomphrena elegans Mart. (Amaranthaceae) e de caules de Myracrodruon urundeuva Allemão (Anacardiaceae). Foram testados quatro extratos e 18 frações, com diferentes polaridades. Dez gramas de grãos de trigo foram pulverizados com 1 mL de cada extrato a 10% (p/v). Após a evaporação do solvente a 38 ºC, os grãos foram acondicionados em recipientes juntamente com 20 indivíduos adultos de Sitophilus zeamais não sexados, com 10 a 20 dias de idade. As avaliações foram feitas no quinto e no décimo dia, contando-se o número de insetos mortos e descartando-os. Os extratos foliares de G. elegans ocasionaram mortalidade de 27% a 60% até o quinto dia, enquanto os demais extratos testados, quando ativos, não ultrapassaram a faixa de 20% de mortalidade no mesmo período. No décimo dia, os extratos mais ativos foram o proveniente de A. phalerata (hexânico, 36,5%) e todos os de G. elegans (52% a 80,5%), enquanto os demais extratos causaram até 30% de mortalidade.
Isolation and characterization of insecticidal activity of (Z)‐asarone from Acorus calamus L
Insect Science, 2008
The insecticidal activity of Acorus calamus L. rhizome‐derived material against adults of Sitophilus zeamais Motschulsky was examined by using repellency method and contact toxicity. The biologically active constituent of the A. calamus rhizome was separated and identified. The results showed that the ethanol extract of A. calamus had strong repellency and contact effect to S. zeamais and the active constituent of the A. calamus was characterized as (Z)‐asarone by spectroscopic analysis. Responses from the tests varied with exposure times and doses. In the repellency test, ethanol extract of A. calamus had 93.92% repellency at 629.08 μg/cm2 but only 71.38% at 157.27 μg/cm2 12 h after treatment. As a contrast, (Z)‐asarone showed 84.50% repellency at 314.54 μg/cm2 and 77.02% at 78.63 μg/cm2 12 h after treatment. In the filter paper diffusion test, ethanol extract of A. calamus caused 95.56% and 17.78% mortality to S. zeamais at 314.54 μg/cm2 and 78.63 μg/ cm2 4 days after treatment, w...
Plant secondary metabolites against arthropods of medical importance
Phytochemistry Reviews, 2019
Natural compounds of botanical origin are increasingly being investigated for the development of novel biocides. Intensive use of synthetic biocides and the confined array of chemical classes in use has led to the buildup of unwanted residues and to parasites' adaptive responses and resistance. Meanwhile, the geographic and host ranges of arthropod vectors and vector-borne diseases are broadening. In an effort to develop ''friendly'' biocidal compounds for the environment and human health, plant secondary metabolites originating in a number of botanical families could be engaged. This mini-review compiles the recently available knowledge on plant secondary metabolites exhibiting biocidal properties and provides a brief overview on their activity against arthropods with a focus on toxic and repellent properties. The selected examples show that it is valuable to consider plants as a promising source for new products development to support the fight against arthropods related to human health. Finally, we outline the biocides regulatory framework in the European Union (EU) and pinpoint some issues of concern regarding the development of low risk biocides.
Insecticidal and antifungal chemicals produced by plants: a review
Environmental Chemistry Letters, 2012
Leaf-cutting ants of the Attini tribe are a major pest of agricultural and forestry productions in the New World. Economic losses caused by these ants were estimated at several million dollars per year. These ants need to live in symbiosis with a basidiomycete fungus. Due to their mutualistic interaction with the symbiotic fungus, management of Attini ants can be done with insecticides or fungicides or both. So far, synthetic pesticides were the main control means, albeit with negative effects on the environment. Very few studies describe alternative methods for the control of leaf-cutting ants such as the use of insecticidal and fungicidal plant extracts. There is therefore a need of knowledge on phytochemicals and plants that could be used as insecticides and fungicides. Here, we review chemicals of plant origin and species with insecticidal and fungicidal activities. We establish a list of plants and phytochemicals that could manage leaf-cutting ants and also other insects, notably insects that use fungusbased agriculture. An exhaustive literature search of 1965 references from 1923 to 2010 was conducted using scientific databases, chemical databases, botanical databases, and books to identify published papers related to insecticidal and fungicidal chemical compounds stemmed from plant species. The major points are the following: (1) 119 and 284 chemicals have been cited in the literature for their insecticidal and fungicidal activities, respectively; (2) 656 and 1,064 plant species have significant insecticidal and fungicidal activities, respectively; (3) 3 main chemical classes were most cited for these activities: alkaloids, phenolics, and terpenoids; (4) 20 interesting chemicals with the both insecticidal and fungicidal activities were found; and (5) 305 plant species containing these chemicals were cited. To conclude, 20 chemicals: caryophyllene oxide, cinnamaldehyde, eugenol, helenalin, linalool, menthone, myristicin, pulegone, thymol, anethole, anisaldehyde, elemicin, isopimpinellin, plumbagin, podophyllotoxin, psoralen, xanthotoxin, anonaine, solamargine, and tomatine; two main plant families, Lamiaceae and Apiaceae; and 17 species of these families were particularly interesting for the management of leaf-cutting ants.
An insecticidal rocaglamide derivatives and related compounds from Aglaia odorata (Meliaceae)
Phytochemistry, 1999
Organic extracts of the twigs and leaves of Aglaia odorata yielded eight insecticidal cyclopentatetrahydrobenzofuran rocaglamide derivatives including three congeners which proved to be new natural products. Moreover, four new cyclopentatetrahydrobenzopyran aglain derivatives, as well as the known aminopyrrolidine odorine and odorinol, syringaresinol and flavonoid derivatives were also isolated. Structure elucidation of the new compounds is described and a rationale of the biosynthesis of the rocaglamide and aglain congeners is considered. The isolated rocaglamide derivatives exhibited strong insecticidal activity towards neonate larvae of the polyphagous pest insect Spodoptera littoralis when incorporated into artificial diet with LC50 values varying from 1.0–8.0 ppm. The most active compounds showed LC50 values between 1.0 and 1.1 ppm, comparable to those of the insecticide azadirachtin, which was used as a positive control. The remaining compounds isolated from A. odorata were inactive with regard to insecticidal activity.
New insecticidal rocaglamide derivatives from flowers of Aglaia duperreana (Meliaceae)
Phytochemistry, 1999
Flowers of Aglaia duperreana collected in Vietnam yielded thirteen insecticidal cyclopentatetrahydrobenzofuran derivatives of the rocaglamide type including five compounds which proved to be new natural products. Structure elucidation of the new compounds and their insecticidal activity against larvae of the pest insect Spodoptera littoralis are described. Most of the isolated rocaglamide derivatives exhibited strong to moderate insecticidal activity. The most active compounds were similar with regard to their bioactivity to the well known natural insecticide azadirachtin. However, replacement of the OH-group at C-8b (that is a characteristic structural feature of most known rocaglamide congeners) by an OC2H5-substituent as present in two of the isolated new derivatives was found to result in a loss of insecticidal activity.
Biologically active constituents of tropical and subtropical plants
Pure and Applied Chemistry, 1994
Methanol extracts of a number of tropical and subtropical plants, such as Ailanthus altissima, Acanthospennum hispidum, Hentiera littoralis, and seed cake of Azadirachta indica ("neem cake"), have been tested for antifeedant, insecticidal, insect growth regulating (IGR), nematicidal, bactericidal, and fungicidal activity. Antifeedant activities towards Epilachna vanvestis were observed with the Ailanthus, Acanthospennum, Hentiera, and neem cake extracts, resp., IGR activities were found in addition with Ailanthus and neem cake extracts. Bactericidal and fungicidal effects were observed with extracts from A. hispidum. We report on isolation, structure, and biological activity of some of the active principles.
Joseph fJ Karchesy This study identified new compounds with pest control activities. The two sources of candidates that were followed here were the main heartwood extract of Alaska Yellow Cedar (AYC) constituents and several semi-synthetic counterparts. Five compounds were isolated and identified for the first time in AYC heartwood in this research: two monoterpenes, two sesquiterpenes, and one lignan. The two monoterpenes were (1 S)-2-oxo-3-p-menthenol (41) and (4R)-4-10 10