Metabolism of thymol and trans-anethole in larvae of Spodoptera litura and Trichoplusia ni (Lepidoptera: Noctuidae)

Metabolism of the monoterpenoid thymol and the phenylpropanoid trans-anethole, both constituents of essential oils, was investigated following topical and oral administration of the compounds to the tobacco cutworm (Spodoptera litura) and the cabbage looper (Trichoplusia ni). In both species and irrespective of route, administration of thymol resulted in the excretion of its 3-O-beta-glucoside, whereas trans-anethole was hydroxylated on the side chain methyl group. Both metabolites were isolated and their structures elucidated by interpretation of their mass and NMR spectra. Previous experiments indicated that trans-anethole synergized the toxicity of thymol in S. litura, but analyses of feces indicated that metabolism of thymol was not significantly suppressed when the two compounds were orally coadministered to T. ni larvae.     

Insecticidal and acetylcholine esterase inhibition activity of apiaceae plant essential oils and their constituents against adults of German cockroach (Blattella germanica)

We evaluated the insecticidal and acetylcholine esterase (AChE) inhibition activity of 11 Apiaceae plant essential oils and their constituents in adult male and female Blattella germanica. Of the 11 Apiaceae plant essential oils tested, dill (Anethum graveolens), carvi (Carum carvi), and cumin (Cuminum cyminum) demonstrated >90% fumigant toxicity against adult male German cockroaches at a concentration of 5 mg/filter paper. In a contact toxicity test, dill (Anethum graveolens), carvi (Carum carvi), cumin (Cuminum cyminum), and ajowan (Trachyspermum ammi) produced strong insecticidal activity against adult male and female German cockroaches. Among the test compounds, (S)-(+)-carvone, 1,8-cineole, trans-dihydrocarvone, cuminaldehyde, trans-anethole, p-cymene, and γ-terpinene demonstrated strong fumigant toxicity against adult male and female B. germanica. In a contact toxicity test, carveol, cuminaldehyde, (S)-(+)-carvone, trans-anethole, thymol, and p-cymene showed strong contact toxicity against adult male and female B. germanica. IC(50) values of α-pinene, carvacrol, and dihydrocarvone against female AChE were 0.28, 0.17, and 0.78 mg/mL, respectively. The toxicity of the blends of constituents identified in 4 active oils indicated that carvone, cuminaldehyde, and thymol were major contributors to the fumigant activity or contact toxicity of the artificial blend.     

Antifeedant effects of the limonoids from Entandrophragma candolei (Meliaceae) on the gram pod borer, Helicoverpa armigera (Lepidoptera: Noctuidae)

The biological activity of the limonoids prieurianin and epoxyprieurianin isolated from Entandrophragma candolei (Harms) (Meliaceae) and their respective acetates was assessed using the gram pod borer, Helicoverpa armigera (Hubner) (Lepidoptera: Noctuidae). The compounds exhibited strong antifeedant activity in a diet choice bioassay with epoxyprieurianin acetate being most effective with 48.3 ppm deterring feeding by 50% (DI50) and prieurianin the least effective (DI50 = 91.4 ppm). The effect on growth of larvae was concomitant with the reduced feeding by neonate and third instar larvae. In nutritional assays, all the compounds reduced growth and consumption when fed to larvae without any effect on efficiency of conversion of ingested food (ECI), suggesting antifeedant activity alone. No toxicity was observed nor was there any significant affect on nutritional indices following topical application, further suggesting that prieurianin-type limonoids act specifically as feeding deterrents.     

Chemical composition and antifungal activity of essential oils from different tissues of Japanese Cedar (Cryptomeria japonica)

In this study antifungal activities of essential oils from different tissues of Japanese cedar (Cryptomeria japonica D. Don) against four wood decay fungi and six tree pathogenic fungi were investigated. In addition, the yields of essential oils obtained by water distillation were compared and their constituents determined by GC-MS analyses. The yield of essential oils from four tissues of Japanese cedar is in the decreasing order of leaf (27.38 mL/kg) > bark (6.31 mL/kg) > heartwood (3.80 mL/kg) > sapwood (1.27 mL/kg). Results obtained from the antifungal tests demonstrate that the essential oil of Japanese cedar heartwood used against Laetiporus sulphureus and Trametes versicolor and sapwood essential oil used against L. sulphureus had strong antifungal activities at 500 mug/mL, with IC(50) values of 39, 91, and 94 microg/mL, respectively. Besides, the essential oils of Japanese cedar heartwood used against Rhizoctonia solani, Collectotrichum gloeosporioides, Fusarium solani, and Ganoderma australe had strong antifungal activities at 500 microg/mL, with IC(50) values of 65, 80, 80, and 110 microg/mL, respectively. GC-MS analyses showed that the sesquiterpene hydrocarbon compounds dominate in the essential oil from Japanese cedar heartwood, amounting to a total percentage of 82.56%, with the major compounds of delta-cadinene (18.60%), isoledene (12.41%), and gamma-muurolene (11.82%). It is proposed that the excellent antifungal activities of Japanese cedar heartwood essential oils might correlate with the presence of these compounds.     

Insecticidal effect of phthalides and furanocoumarins from Angelica acutiloba against Drosophila melanogaster

Insecticidal activity of Angelica acutiloba extract and its constituents was investigated and compared with that of rotenone. Bioassay-guided isolation of the chloroform extract of A. acutiloba against larvae of Drosophila melanogaster afforded two phthalides, (Z)-butylidenephthalide (1) and (Z)-ligustilide (2), and two furanocoumarins, xanthotoxin (3) and isopimpinellin (4). The structures of these compounds were established by spectroscopic analysis. The isolated compounds 1, 2, 3, and 4 exhibited LC(50) values of 0.94, 2.54, 3.35, and 0.82 micromol/mL of diet concentration against larvae of D. melanogaster, respectively. Against both sexes (males/females, 1:1) of adults (5-7 days old), compound 1 showed the most potent activity with a LD(50) value of 0.84 microg/adult. Compound 1 is a more active insecticide than rotenone (LD(50) = 3.68 microg/adult) and has potential as a novel insect control agent. However, compound 2 was inactive against adults. The structure-activity relationship of phthalides isolated indicated that the aromaticity appeared to play an important role in the activity of both larvae and adults. To determine the insecticide mode of action for acute adulticidal activity, acetylcholinesterase (AChE) inhibitory activity was also investigated in vitro, and the result indicated that the acute adulticidal activity of compounds 3 and 4 was due to the inhibition of AChE.     

Chemical composition and mosquito larvicidal activity of essential oils from leaves of different Cinnamomum osmophloeum provenances

Chemical compositions of leaf essential oils from eight provenances of indigenous cinnamon (Cinnamomum osmophloeum Kaneh.) were compared. According to GC-MS and cluster analyses, the leaf essential oils of the eight provenances and their relative contents were classified into five chemotypes-cinnamaldehyde type, linalool type, camphor type, cinnamaldehyde/cinnamyl acetate type, and mixed type. The larvicidal activities of leaf essential oils and their constituents from the five chemotypes of indigenous cinnamon trees were evaluated by mosquito larvicidal assay. Results of larvicidal tests demonstrated that the leaf essential oils of cinnamaldehyde type and cinnamaldehyde/cinnamyl acetate type had an excellent inhibitory effect against the fourth-instar larvae of Aedes aegypti. The LC(50) values for cinnamaldehyde type and cinnamaldehyde/cinnamyl acetate type against A. aegypti larvae in 24 h were 36 ppm (LC(90) = 79 ppm) and 44 ppm (LC(90) = 85 ppm), respectively. Results of the 24-h mosquito larvicidal assays also showed that the effective constituents in leaf essential oils were cinnamaldehyde, eugenol, anethole, and cinnamyl acetate and that the LC(50) values of these constituents against A. aegypti larvae were <50 ppm. Cinnamaldehyde had the best mosquito larvicidal activity, with an LC(50) of 29 ppm (LC(90) = 48 ppm) against A. aegypti. Comparisons of mosquito larvicidal activity of cinnamaldehyde congeners revealed that cinnamaldehyde exhibited the strongest mosquito larvicidal activity.     

Antifeedant and insecticide properties of a limonoid from Melia azedarach (Meliaceae) with potential use for pest management

In the course of screening for novel naturally occurring insecticides from plants, the activity of the fruit extract of the Argentinian Melia azedarach L. (Meliaceae) and its recently described limonoid meliartenin were investigated. The antifeedant activity of the fruit extract was tested on a variety of herbivore and granivorous insects through choice tests. Sixteen of 17 species belonging to three orders consume significantly less food when treated with the extract. The bioactivity of the isolated active compound meliartenin and its interchangeable isomer 12-hydroxiamoorastatin (1) was further studied. In choice tests, compound 1 inhibited feeding of Epilachna paenulata Germ. (Coleoptera, Coccinellidae) larvae, with an ED(50) value of 0.80 microg/cm(2), comparable to that of azadirachtin (2) and lower than that of toosendanin (3) (0.72 and 3.69 microg/cm(2), respectively), both compounds used for comparison purposes. In no-choice tests, E. paenulata larvae reared on food treated with 1 or 2 ate less, gained less weight, and suffered greater mortality rates than control larvae. The activity of compound 1 was comparable to that of 2, with LD(50) values of 0.76 and 1.24 microg/cm(2), respectively, at 96 h. Shorter LT(50) values were recorded for 1 at 4 and 1 microg/cm(2) in comparison with 2. Thus, M. azedarach fruit extract and its active principle have interesting potential for use in pest control programs.     

Larvicidal and adulticidal activity of alkylphthalide derivatives from rhizome of Cnidium officinale against Drosophila melanogaster

The insecticidal activity of the chloroform extract of Cnidium officinale rhizomes and its constituents was investigated against larvae and adults of Drosophila melanogaster and compared with that of rotenone. Bioassay-guided isolation of the chloroform extract of C. officinale resulted in the isolation and characterization of four alkylphthalides, cnidilide (1), (Z)-ligustilide (2), (3S)-butylphthalide (3), and neocnidilide (4). The structures of these compounds were established by spectroscopic analysis. The isolated compounds 2, 3, and 4 exhibited LC50 values of 2.54, 4.99, and 9.90 micromol/mL of diet concentration against larvae of D. melanogaster, respectively. Against both sexes (males/females, 1:1) of adults (5-7 days old), compound 3 showed the most potent activity of the compounds isolated with the LD50 value of 5.93 microg/adult, comparable to that of rotenone (LD50 = 3.68 microg/adult). Structure-activity relationships of phthalides isolated suggest that the presence of conjugation with the carbonyl group in the lactone ring appeared to play an important role in the larvicidal activity. Acetylcholinesterase (prepared from the adult heads of D. melanogaster) inhibitory activity was also investigated in vitro to determine the insecticide mode of action for the acute adulticidal activity.     

Evaluation of insecticidal activity of diterpenes and lignans from Aristolochia malmeana against Anticarsia gemmatalis

The insecticidal activity of hexane extracts from the roots and leaves of Aristolochia malmeana was evaluated against Anticarsia gemmatalis larvae by topical application. Extract from the roots was the most active and caused 50% mortality in larvae at 308.4 microg/microL. From this extract, a clerodane diterpene, (-)-kolavenic acid, and three lignans, (-)-kusunokinin, (-)-hinokinin, and (8 S,8' R,9 S)-cubebin, were isolated by chromatography and partition procedures and then evaluated for their insecticidal activities either individually or in pairs. (-)-Kusunokinin showed higher activity against A. gemmatalis (LD10=9.3, LD50=230.1 microg/microL) than the crude extract, and its activity was dose-dependent, whereas the other constituents did not exhibit any significant activity. Together with (-)-kusunokinin and (-)-hinokinin, (-)-copalic acid, (-)-2-oxokolavenic acid, (-)- ent-6-beta-hydroxy-copalic acid, (8 R,8' R,9 R)- and (8 R,8' R,9 S)-cubebins, (-)-fargesin, and (-)-phillygenin were isolated from the hexane extract of the leaves. The compounds were identified on the basis of spectroscopic analysis.     

Composition and anti-insect activity of essential oils from Tagetes L. species (Asteraceae, Helenieae) on Ceratitis capitata Wiedemann and Triatoma infestans Klug

Essential oils from four species of the genus Tagetes L. (Asteraceae, Helenieae) collected in Tucuma?n province, Argentina, were evaluated for their chemical composition, toxicity, and olfactory activity on Mediterranean fruit fly Ceratitis capitata Wiedemann adults and for repellent properties on Triatoma infestans (Klug) (Chagas disease vector). Yields of essential oils range from 0.2 to 0.8% (v/w). The same main constituents among Tagetes minuta L., Tagestes rupestris Cabrera, and Tagetes terniflora Kunth, (cis-trans)-ocimenes, (cis-trans)-tagetones, and (cis-trans)-ocimenones showed important differences in their relative compositions. Tagetes filifolia Lag. was characterized by the recognized phenylpropanoids methylchavicol and trans-anethole as the main components. LD(50) was ≤20 μg/insect in topical bioassays. T. rupestris was the most toxic to C. capitata females, whereas the other oils presented similar toxicities against males and females. Tagetes rupestris oil attracted both sexes of C. capitata at 5 μg, whereas T. minuta showed opposite activities between males (attractant) and females (repellent). Oils from T. minuta and T. filifolia were the most repellent to T. infestans. The results suggest that compositions of essential oils influence their insecticidal and olfactory properties. The essential oils from Tagetes species show an important potential as infochemical agents on insects' behaviors. This study highlights the chemical variability of essential oils as a source of variation of anti-insect properties.     

6beta-hydroxygedunin from Azadirachta indica. Its potentiation effects with some non-azadirachtin limonoids in neem against lepidopteran larvae

The biological activity of 6beta-hydroxygedunin isolated from Azadirachta indica A. Juss. was assessed using the gram pod borer, Helicoverpa armigera (Hubner), and Asian armyworm, Spodoptera litura (Fabricius) (Lepidoptera: Noctuidae), alone and in combination with other limonoids, gedunin, salannin, nimbinene, and azadirachtin. The compound exhibited growth inhibitory activity in artificial diet bioassays, with 24.2 and 21.5 ppm, respectively, inhibiting growth by 50%. This efficacy was higher in comparison to gedunin (EC(50) = 50.8 and 40.4 ppm), salannin (EC(50) = 74.5 and 72.0 ppm), and nimbinene (EC(50) = 391.4 and 404.5 ppm). Azadirachtin, however, remained the most active neem allelochemical against both insect species. Nutritional assays clearly demonstrated that, though relative consumption and growth rates of fourth instar larvae were reduced, gedunin-type compounds induced physiological toxicity, evident by reduced efficiency of conversion of ingested food (ECI) in feeding experiments. Salannin and nimbinene, on the contrary, induced concentration-dependent feeding deterrence only. In feeding experiments, combinations of the compounds revealed that when azadirachtin was present in a mixture, EC(50) values did not deviate from the individual efficacy of azadirachtin (0.26 and 0.21 ppm, respectively) against H. armigera and S. litura larvae. However, a combination without azadirachtin did show a potentiation effect with potent EC(50) values among structurally different molecules, i.e., when salannin or nimbinene was combined with 6beta-hydroxygedunin or gedunin rather than structurally similar salannin + nimbinene or 6beta-hydroxygedunin + gedunin. Obviously, azadirachtin being the most active compound in neem is not synergized or influenced by any other limonoid, but other non-azadirachtin limonoids were more potent in specific combinations vis-à-vis the structural chemistry of the compound. It is obvious from the present study that potentiation among non-azadirachtin limonoids having explicitly two different modes of action, such as feeding deterrence and physiological toxicity, may be playing a significant role in the potentiation effect.     

Investigation of the Origanum onites L. essential oil using the chorioallantoic membrane (CAM) assay

The in vivo test on the chorioallantoic membrane of the fertilized hen's egg (CAM assay) is a current method to determine antiangiogenic, antiinflammatory activity and toxic effects of individual compounds or complex plant extracts. The method is used for testing natural compounds in small amounts for revealing various modes of action and the complex mechanisms related to angiogenesis and inflammation. Furthermore, possible side effects such as membrane irritation, toxic, and anticoagulant properties of the investigated material in question can be detected. For the evaluation, the essential oil obtained by hydrodistillation of the aerial parts of Origanum onites L., a common spice and medicinal plant, was tested for its effect in the chorioallantoic membrane (CAM) assay. The essential oil composition was revealed by means of gas chromatography-mass spectrometry (GC-MS). Eighty three components were identified, representing 99.1% of the total oil. Carvacrol, thymol, p-cymene, and gamma-terpinene were found as major components and were also individually tested in the CAM assay. Along with the monoterpenes carvacrol and thymol, their methyl ether derivatives were also examined for comparison of their physiological action. Neither the essential oil nor its components showed any pronounced antiinflammatory or antiangiogenic property in the CAM assay, at 10-250 microg/pellet. However, the irritant effect of the essential oil was linked to thymol in a dose-response fashion, up to 10 microg/pellet, where it was still showing irritation.     

Effect of maturation on the composition and biological activity of the essential oil of a commercially important Satureja species from Turkey: Satureja cuneifolia Ten. (Lamiaceae)

The essential oil obtained by hydrodistillation from aerial parts of Satureja cuneifolia Ten., collected in three different maturation stages such as preflowering, flowering, and postflowering, were analyzed simultaneously by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). Thymol (42.5-45.2%), p-cymene (19.4-24.3%), and carvacrol (8.5-13.2%) were identified as the main constituent in all stages. At the same time, the essential oils and main components were evaluated for their antimicrobial activity using a microdilution assay resulting in the inhibition of a number of common human pathogenic bacteria including methicillin-resistant Staphylococcus aureus (MRSA) and the yeasts Candida albicans and Candida tropicalis. The minimum inhibitory concentrations (MIC) varied between 62.5 and 250 microg/mL within a moderate antimicrobial activity range. Furthermore, the antioxidant capacity of the essential oils and major components thymol and carvacrol were examined in vitro. The essential oils obtained from S. cuneifolia in three different stages and its main components were interacted with 1,1-diphenyl-2-picrylhydrazyl (DPPH (*)) as a nitrogen-centered stable radical, resulting in IC 50 = 1.6-2.1 mg/mL. In addition, the effects on inhibition of lipid peroxidation of the essential oils were assayed using the beta-carotene bleaching method. All of the tested oils inhibited the linoleic acid peroxidation at almost the same level as butylated hydroxytoluene (BHT) (93.54-94.65%). BHT and ascorbic acid were used as positive controls in the antioxidant assays.     

Chemical composition, seasonal variability, and antifungal activity of Lavandula stoechas L. ssp. stoechas essential oils from stem/leaves and flowers

Essential oils from the stems/leaves (L) and flowers (F) of Lavandula stoechas L. ssp. stoechas growing wild in southern Sardinia (Italy) were extracted by hydrodistillation and analyzed by gas chromatography coupled with flame ionization detector and ion trap mass spectrometry. The major compound was fenchone, accounting for, on average, 52.60% in L and 66.20% in F, followed by camphor (13.13% versus 27.08%, in L and F, respectively). F essential oil yields (volume per dry weight) decreased from the beginning to the end of the flowering stage, whereas L yields remained constant during the year. The nine main compounds derived from two different subpathways, A and B. The compounds that belong to the same subpathway showed a similar behavior during the year. The essential oils were tested for their antifungal activity using the paper disk diffusion method. The essential oils tested were effective on the inactivation of Rhizoctonia solani and Fusarium oxysporum and less effective against Aspergillus flavus. Among the single compounds tested, fenchone, limonene, and myrtenal appeared to be the more effective on the inhibition of R. solani growth.     

Contact and fumigant toxicity of a botanical-based feeding deterrent of the stable fly, Stomoxys calcitrans (Diptera: Muscidae)

The stable fly, Stomoxys calcitrans (L.), has been considered one of the most serious biting flies of confined and pastured livestock. The economic losses caused by the stable fly to the cattle industry in the United States exceed $2 billion annually. Current practices for managing stable flies using insecticides provide only marginal control. Insecticide resistance has also been recently reported in stable flies. The present study reports the use of plant-based insecticides, for example, essential oils, as alternatives for managing this fly pest. The toxicity of several plant essential oils and selected ingredient compounds was evaluated by contact and fumigant toxicity bioassays. Catnip oil (20 mg dosage) showed the highest toxicity against stable flies, the shortest knock-down time (～7 min), and the quickest lethal time (～19 min). Toxicity levels similar to catnip oil were found among three insect repellent compounds (N,N-diethyl-3-methylbenzamide, 2-methylpiperidinyl-3-cyclohexene-1-carboxamide, (1S,2'S)-2-methylpiperidinyl-3-cyclohexene-1-carboxamide). No differences in knock-down and lethal times were found among the catnip oil and its two active ingredient compounds. Similar stable fly mortality was observed using a 20 mg dose of catnip oil in a modified K&D system and a fumigant jar. When catnip oil was topically applied to stable flies, the least lethal dose was 12.5 μg/fly, and a 50 μg/fly dose resulted in 100% mortality. The blood-feeding behavior of stable flies was also negatively affected by the topical application of catnip oil, and the effect was dose-dependent. This study demonstrated that catnip oil has both contact and fumigant toxicity against the stable fly and thus has the potential as an alternative for stable fly control.     

Composition of the essential oils of Thymus and Origanum species from Algeria and their antioxidant and antimicrobial activities

The composition of the essential oils of Origanum and Thymus species restricted to Algeria and the North Africa region was determined. Antioxidant and antibacterial activities of the isolated essential oils were also determined. The oils of oregano plants were strongly characterized by p-cymene (16.8-24.9%), gamma-terpinene (16.8-24.9%), thymol (8.4-36.0%), and carvacrol (1.1-29.7%), a thymol chemotype for Origanum floribundum and a alpha-terpineol chemotype for Thymus numidicus being described for the first time. The strains of Listeria monocytogenes tested were relatively resistant to the action of essential oils of either Origanum or Thymus species. All essential oils possessed antioxidant activity, but this was dependent on the specific chemical composition and the method employed to determine such activity.     

Feeding deterrents from Dictamnus dasycarpus Turcz against two stored-product insects

The screening for insecticidal principles from several Chinese medicinal herbs showed that the root bark of Dictamnus dasycarpus possessed significant feeding deterrence against two stored-product insects (Tribolium castaneum and Sitophilus zeamais). From the methanol extract, two feeding deterrents were isolated by bioassay-guided fractionation. The compounds were identified as fraxinellone and dictamnine from their spectroscopic data. Fraxinellone was demonstrated to possess feeding deterrent activity against adults and larvae of T. castaneum as well as S. zeamais adults with EC50 values of 36.4, 29.1, and 71.2 ppm, respectively. Dictamnine was shown to have feeding deterrent activity against adults and larvae of T. castaneum as well as S. zeamais adults with EC50 values of 57.6, 47.9, and 91.7 ppm, respectively.     

杀虫剂对苹果黄蚜与七星瓢虫的毒力及选择性研究

采用FAO推荐的点滴法,测定了15种常用杀虫剂对苹果黄蚜及其天敌七星瓢虫幼虫的毒力,比较了药剂在二者之间的毒力选择性。结果表明,供试杀虫剂中以吡虫啉对七星瓢虫幼虫和苹果黄蚜的选择性最高,其选择性比值(七里瓢虫LD50/苹果黄蚜LD50)为135．56,其次为氟氯氰菊酯、氯氰菊酯和马拉硫磷,其选择性比值分别为114．00、62．86和45．43。吡虫啉、氟氯氰菊酯、氯氰菊酯和马拉硫磷等选择性高的杀虫剂对苹果黄蚜相对毒力高,而对其天敌七星瓢虫相对安全,在协调苹果黄蚜的化学防治与生物防治策略中应选用对害虫毒力高,而对天敌相对安全的杀虫剂。     

Evaluation of the cytotoxicity, genotoxicity, mutagenicity, and antimutagenicity of propolis from Tucuman, Argentina

This study evaluates the toxic, genotoxic/mutagenic, and antimutagenic effects of propolis extract from Amaicha del Valle, Tucumán, Argentina. The cytotoxicity assays carried out with the lethality test of Artemia salina revealed that the LD50 was around 100 microg/mL. Propolis extracts showed no toxicity to Salmonella typhimurium TA98 and TA100 strains and Allium cepa at concentrations that have antibiotic and antioxidant activities. Otherwise, for the testing doses, neither genotoxicity nor mutagenicity was found in any sample. The propolis extracts were able to inhibit the mutagenesis of isoquinoline (IQ) and 4-nitro o-phenylenediamine (NPD) with ID50 values of 40 and 20 microg/plate, respectively. From this result, the studied propolis may be inferred to contain some chemical compounds capable of inhibiting the mutagenicity of direct-acting and indirect-acting mutagens. A compound isolated from Amaicha del Valle propolis, 2',4'-dihydroxychalcone, showed cytotoxic activity (LC50 values of 0.5 microg/mL) but was not genotoxic or mutagenic. Furthermore, this compound was able to inhibit the mutagenicity of IQ (ID50 values of 1 microg/plate) but was unable to inhibit the mutagenicity of NPD. Our results suggest a potential anticarcinogenic activity of Amaicha del Valle propolis and the chalcone isolated from it.     

Acaricidal constituents isolated from Sinapis alba L. seeds and structure-activity relationships

Allyl isothiocyanate (AITC) and phenethyl isothiocyanate (PEITC) were isolated from Sinapis alba L. seeds and their effects against Dermatophagoides farinae and D. pteronyssinus were evaluated using the impregnated fabric disk method. The LD 50 values of their compounds and derivatives were then compared with those of a commercial acaricide, benzyl benzoate. On the basis of the LD 50 values against D. farinae, PEITC (0.21 microg/cm(2)) was the most toxic, followed by benzyl isothiocyanate (0.55 microg/cm(2)), phenyl isothiocyanate (1.09 microg/cm(2)), butyl isothiocyanate (1.24 microg/cm(2)), and AITC (1.36 microg/cm(2)); acetyl isothiocyanate (195.01 microg/cm(2)) was the least toxic. In addition, the acaricidal effects of AITC and PEITC against D. farinae were 7.4- and 47.8-fold greater than those of benzyl benzoate, respectively. Against D. pteronyssinus, PEITC was the most toxic (0.19 microg/cm(2)), followed by benzyl isothiocyanate (0.77 microg/cm(2)), phenyl isothiocyanate (1.37 microg/cm(2)), butyl isothiocyanate (1.50 microg/cm(2)), and AITC (2.88 microg/cm(2)); acetyl isothiocyanate (168.82 microg/cm(2)) was the least toxic. AITC and PEITC were 3.3- and 50.4-fold more active than benzyl benzoate against D. pteronyssinus, respectively. Taken together, these findings indicate that AITC, PEITC, and partial derivatives may be useful as preventive agents against dust mites. In addition, these results indicate that structure-activity is related to the aromatic structure, the number of carbon atoms, and the compounds hydrophobicity.