Insecticidal Triterpenes in Meliaceae: Plant Species,Molecules, and Activities: Part II (Cipadessa,Melia)

Plant-originated triterpenes are important insecticidal molecules. Research on the insecticidal activity of molecules from Meliaceae plants has always been a hotspot due to the molecules from this family showing a variety of insecticidal activities with diverse mechanisms of action. In this paper, we discussed 116 triterpenoid molecules with insecticidal activity from 22 plant species of five genera (Cipadessa, Entandrophragma, Guarea, Khaya, and Melia) in Meliaceae. In these genera, the insecticidal activities of plants from Entandrophragma and Melia have attracted substantial research attention in recent years. Specifically, the insecticidal activities of plants from Melia have been systemically studied for several decades. In total, the 116 insecticidal chemicals consisted of 34 ring-intact limonoids, 31 ring-seco limonoids, 48 rearranged limonoids, and 3 tetracyclic triterpenes. Furthermore, the 34 ring-intact limonoids included 29 trichilin-class chemicals, 3 azadirone-class chemicals, and 1 cedrelone-class and 1 havanensin-class limonoid. The 31 ring-seco limonoids consisted of 16 C-seco group chemicals, 8 B,D-seco group chemicals, 4 A,B-seco group chemicals, and 3 D-seco group chemicals. Furthermore, among the 48 rearranged limonoids, 46 were 2,30-linkage group chemicals and 2 were 10,11-linkage group chemicals. Specifically, the 46 chemicals belonging to the 2,30-linkage group could be subdivided into 24 mexicanolide-class chemicals and 22 phragmalin-class chemicals. Additionally, the three tetracyclic triterpenes were three protolimonoids. To sum up, 80 chemicals isolated from 19 plant species exhibited antifeedant activity toward 14 insect species; 18 chemicals isolated from 17 plant species exhibited poisonous activity toward 10 insect species; 16 chemicals isolated from 11 plant species possessed growth-regulatory activity toward 8 insect species. In particular, toosendanin was the most effective antifeedant and insect growth-regulatory agent. The antifeedant activity of toosendanin was significant. Owing to its high effect, toosendanin has been commercially applied. Three other molecules, 1,3-dicinnamoyl-11-hydroxymeliacarpin, 1-cinnamoyl-3-methacryl-11-hydroxymeliacarpin, and 1-cinnamoyl-3-acetyl-11-hydroxymeliacarpin, isolated from Melia azedarach, exhibited a highly poisonous effect on Spodoptera littoralis; thus, they deserve further attention.     

Feeding Deterrence and Toxicity of Neem Triterpenoids

The neem tree, Azadirachta indica, produces a plethora of triterpenoids. One of these is azadirachtin, a complex compound with powerful insecticidal properties. The biosynthesis of azadirachtin starts with a steroid precursor and proceeds via two levels of structural complexity, i.e., furan ring formation and C-ring opening, after which further modifications yield azadirachtin, Antifeedant and toxic properties of azadirachtin against insects were compared with those of various compounds from the two lower levels of structural complexity. To larvae of the moth Spodoptera littoralis, several compounds from the lower structural levels showed strong antifeedant activity, comparable to that of azadirachtin. Nymphs of the locust Schistocerca gregaria in antifeedancy tests were more sensitive to azadirachtin than to the other compounds tested. To Spodoptera littoralis, Schistocerca gregaria, and the bug Oncopeltus fasciatus, azadirachtin was very toxic, exerting severe growth and molt disrupting effects. In contrast, compounds from the lower structural levels than azadirachtin showed virtually no toxicity to these three insects. Thus, although several simpler triterpenoid structures other than azadirachtin have insect antifeedant activity, the combination of strong antifeedant and toxic properties of azadirachtin may provide the more important chemical protection of the neem tree. Our data reveal no explicit link between antifeedant activity and toxicity of individual neem triterpenoids.     

Differential Activity of Multiple Saponins Against Omnivorous Insects with Varying Feeding Preferences

A variety of glycosylated and unglycosylated saponins from seven different plant families (Aquifoliaceae, Asparagaceae, Caryophyllaceae, Dioscoreaceae, Leguminosae, Rosaceae, Sapindaceae) were tested against the corn earworm, Helicoverpa zea, and the fall armyworm, Spodoptera frugiperda. The corn earworm feeds readily on both monocots and dicots, while the fall armyworm is primarily a grass feeder. Most of the saponins were similarly effective or ineffective against both insect species, with the glycosides being the primary active form (compared to aglycones). However, one aglycone possessed antifeedant properties toward the fall armyworm. Thus, in contrast to many plant secondary metabolites effective against either of these two species where the aglycone is more effective, in the case of the saponins the opposite is generally true. This appears to be a contradictory strategy of plant defenses that requires further consideration. The activity of protodioscin against insects is reported for the first time and may be important in insect defense by the bioenergy crop switchgrass.     

Supercritical CO2 extraction of Persea indica: Effect of extraction parameters, modelling and bioactivity of its extracts

The objective of the work was to optimize the extraction of Persea indica L. bioactive compounds by means of supercritical fluid extraction (SFE) and analyze their insecticidal effects. P. indica L. is one of the dominant species of the Canarian laurel forest, a relict of the Tertiary flora. Different extraction conditions (pressure, plant material particle size, temperature, CO₂ flow) and the influence of entrainer were tested and the evolution of the extracted compounds was screened by HPLC-MS. A comparison with conventional techniques such as hydrodistillation (HD) or organic solvent extraction (OSE) was also presented. Particularly, four CO₂ densities ranging from 628.61 kg/m³ to 839.81 kg/m³ were studied in the range of 10.0-20.0 MPa and 40-50 °C. The extracts contained insecticidal ryanodanes of great interest, previously described as insecticidal components of P. indica. The insecticidal antifeedant activity of selected extracts was inspected. A model based on mass transfer equations, the Sovová model, was successfully applied to correlate the experimental data.     

Antifeedant Comparisons of GABA/Glycinergic Antagonists for Diabroticite Leaf Beetles (Coleoptera: Chrysomelidae)

The phagostimulatory sensitivity of diabroticite (Coleoptera, Chrysomelidae, Galerucinae) species to cucurbitacins is not correlated with Cucurbitaceae specialization, indicating that other factors, including the absence of feeding deterrents, may influence host–plant affinities among these beetles. Quinoline, indole, and isoquinoline alkaloids and sesquiterpene lactones believed to antagonize γ-aminobutyric acid/glycine Cl^? ionophores mediating chemoreception were tested on squash blossom disks for antifeedant activity to four diabroticite species with different host plant specializations. Most alkaloids were antifeedant below 30 nmol/disk. Antifeedant concentrations of sesquiterpene lactones were higher than alkaloids for all species. Oligophagous Diabrotica virgifera virgifera was more sensitive to quinoline alkaloids than polyphagous D. undecimpuntata howardi. Diabrotica virgifera virgifera was also more sensitive to the indole alkaloids strychnine, brucine, eburnamonine, and vincamine than D. u. howardi. The closely related D. barberi had sensitivities similar to those of D. v. virgifera but the more distantly related Acalymma vittatum was less sensitive to the antifeedants than D. v. virgifera The isoquinoline alkaloid hydrastine was uniformly antifeedant to all diabroticites. All the GABA/glycine neurotoxicams tested against diabroticites were feeding deterrents and suggest that beetles share a common antifeedant mechanism.     

麻疯树种子提取物对几种害虫的杀虫活性

在室内测定并比较了3种麻疯树种子提取物对同翅目、鳞翅目和鞘翅目害虫桃蚜、菜青虫和米象的杀虫活性。结果显示种子油、种子乙醇提取物和石油醚提取物对3种害虫都具有一定杀虫活性，对桃蚜的触杀活性LC50分别为5．1154、2．0796、13．9882g／L；对米象的杀虫活性LC50分别为8．0243、3．0701、24．3458g／L；种子油和乙醇提取物对菜青虫的胃毒活性LC加分别为18．1043、3．0796g／L，此外这2种提取物对菜青虫也显示出较强的拒食活性；而种子石油醚提取物对菜青虫无明显胃毒活性，拒食活性也很弱。麻疯树种子提取物对3种害虫的相对毒力顺序为乙醇提取物〉种子油〉石油醚提取物。     

Extractives of seeds of the meliaceae: Effects onSpodoptera frugiperda (J.E. Smith),Acalymma vittatum (F.), andArtemia salina Leach

Hexane and ethanol extracts of seeds from 22 species of plants of the family Meliaceae from a number of countries were prepared. The extracts were submitted to antifeedant and toxicity bioassays utilizing fall armyworm [Spodoptera frugiperda (J.E. Smith)] (Lepidoptera: Noctuidae) larvae and striped cucumber beetle [Acalymma vittatum (F.)] (Coleoptera: Chrysomelidae) adults. Toxicity tests were also performed with brine shrimp,Anemia salina Leach. Feeding inhibition and mortality produced by some of these extracts were comparable to and, in certain cases, slightly greater than the effects produced by comparable neem (Azadiracta indica A. Juss.) seed preparations. Brine shrimp toxicity data do not extrapolate to insect activity, and vice versa.Presented at the national meeting of the Entomological Society of America in Hollywood, Florida, December 8–12, 1985.Mention of firm or product names does not imply recommendation or endorsement by USDA over others not mentioned.     

Patterns of Bioactivity and Herbivory on Nothofagus Species from Chile and New Zealand

Nothofagus species from Chile and New Zealand were surveyed in the field for invertebrate abundance and leaf feeding damage and in the laboratory for antifeedant activity against leafrollers (Ctenopsteustis obliquana, Epiphyas postvittana), deterrent activity against pea aphid (Acyrthosiphon pisum), insect growth regulatory activity (Oncopeltus fasciatus), nematicidal activity (Caenorhabditis elegans), antibiotic activity (Pseudomonas solanaciarium), and general toxicity. A data matrix indicated that N. alessandri and N. pumilio most likely have a chemical barrier to insect attack as leaves showed low faunal abundance, low herbivory, and activity in the leafroller antifeedant, aphid deterrent, and nematicidal assays. A chemical examination of N. alessandri that used the leafroller antifeedant test to guide the separation yielded an active fraction containing the flavonoid, galangin, and the stilbene, pinosylvin, which appear to act in concert to deter leafroller feeding. The discovery of the phytoalexin, pinosylvin, in the leaves, raises the possibility that Nothofagus in general, and N. alessandri in particular, may have induced chemical defense mechanisms.     

Action of Extracts of Apiaceae on Feeding Behavior and Neurophysiology of the Field Slug Deroceras reticulatum

A systematic examination was made of the plant family Apiaceae (Umbelliferae) in which extracts of 33 species, representing 32 genera, were screened for antifeedant activity against the field slug Deroceras reticulatum by using an electrophysiological recording assay. In this assay, the olfactory sensory epithelium of the posterior tentacle of the slug was exposed to volatile components of the plant extracts presented in an airstream, and any subsequent activity of the olfactory nerve was recorded. Extracts of 22 species elicited a range of nervous activity in the preparation. A feeding bioassay was used to measure any change in consumption when extracts were added to a standard food. Statistical analysis of data obtained from both electrophysiological traces and the feeding bioassays identified extracts of Petroselinum crispum, Conium maculatum, and Coriandrum sativum as being the most neuroactive as well as the most antifeedant.     

Extraction of natural insecticide azadirachtin from neem (Azadirachta indica A. Juss) seed kernels using pressurized hot solvent

Plant-derived pesticides are gaining popularity on account of the increasing sustainable farming practices and also due to the environmental and health hazards resulting from excessive usage of their synthetic counterparts. The neem (Azadirachta indica A. Juss) tree, belonging to the Meliaceae family, is a storehouse of insecticidal azadirachtin, which possess antifeedant, growth disrupting and larvicidal properties against an array of agricultural insect pests. Pressurized Hot Solvent Extraction (PHSE) is fast emerging as an efficient means for recovering valuable active ingredients from natural plant matrices at an accelerated rate and with a reduced solvent consumption. The technique employing heated organic solvents at elevated pressures is a potential green substitute for conventional solvent extractions. The present study deals with the extraction of azadirachtin from defatted neem seed kernels (NSK) using pressurized methanol. Important operating variables like temperature, pressure, extraction time, solvent flow rate and particle size influencing the extraction efficiency were investigated in detail. The azadirachtin content in the extracts was determined by HPLC. The optimum conditions for maximizing azadirachtin yield were found to be 50 °C temperature, 50 bar pressure, −60 + 80 mesh particle size and 5 mL/min extractant flow rate. Under optimal conditions, 210.93 mg azadirachtin was extracted per 100 g defatted NSK within an extraction time of 100 min. Moreover, the proposed method resulted in 1.5 fold reduction in solvent consumption as compared to conventional maceration.     

Response of Epilachna paenulata to Two Flavonoids, Pinocembrin and Quercetin, in a Comparative Study

We examined the effects of the flavonoids pinocembrin and quercetin on the feeding behavior, survival, and development of the Cucurbitaceae pest Epilachna paenulata (Coleoptera: Coccinellidae). In no-choice experiments, 48 hr-consumption of Cucurbita maxima Duch. leaves treated with pinocembrin at 1, 5, and 50 μg/cm² was less than one third of that for leaves treated with 0.1 μg/cm² of pinocembrin or untreated leaves. Larvae stopped feeding after 9 days of high doses of pinocembrin (5 and 50 μg/cm²), and larval weight and survival were negatively affected by pinocembrin at 1–50 μg/cm². Delayed mortality in comparison to food-deprived larvae suggests that the mechanism of action for pinocembrin is chronic intoxication, rather than simple starvation from antifeedant effects. In contrast, leaf consumption and larval weight were not significantly affected by quercetin (at 0.1, 1, 5, and 50 μg/cm²) while mortality rates were only slightly increased. The response of E. paenulata larvae in a choice-test to combinations of pinocembrin at antifeedant doses (5 and 50 μg/cm²) and quercetin at phagostimulant doses (0.01 and 0.1 μg/cm²) indicated that the feeding deterrent activity of the former completely overshadowed the stimulant activity of the latter. These results demonstrate the different responses of one insect species to two widely distributed plant flavonoids. Pinocembrin strongly affected survival of E. paenulata while quercetin had only a weak effect without major consequences on the insect life-cycle.     

The Phorbol Ester Fraction from Jatropha curcas Seed Oil: Potential and Limits for Crop Protection against Insect Pests

The physic nut shrub, Jatropha curcas (Euphorbiaceae), has been considered as a “miracle tree”, particularly as a source of alternate fuel. Various extracts of the plant have been reported to have insecticidal/acaricidal or molluscicidal/anthelminthic activities on vectors of medical or veterinary interest or on agricultural or non-agricultural pests. Among those extracts, the phorbol ester fraction from seed oil has been reported as a promising candidate for use as a plant-derived protectant of a variety of crops, from a range of pre-harvest and post-harvest insect pests. However, such extracts have not been widely used, despite the “boom” in the development of the crop in the tropics during recent years, and societal concerns about overuse of systemic chemical pesticides. There are many potential explanations to such a lack of use of Jatropha insecticidal extracts. On the one hand, the application of extracts potentially harmful to human health on stored food grain, might not be relevant. The problem of decomposition of phorbol esters and other compounds toxic to crop pests in the field needing further evaluation before such extracts can be widely used, may also be a partial explanation. High variability of phorbol ester content and hence of insecticidal activity among physic nut cultivars/ecotypes may be another. Phytotoxicity to crops may be further limitation. Apparent obstacles to a wider application of such extracts are the costs and problems involved with registration and legal approval. On the other hand, more studies should be conducted on molluscicidal activity on slugs and land snails which are major pests of crops, particularly in conservation agriculture systems. Further evaluation of toxicity to natural enemies of insect pests and studies on other beneficial insects such as pollinators are also needed.     

Screening and Molecular Identification of Bacteria from the Midgut of Amphimallon solstitiale Larvae Exhibiting Antagonistic Activity against Bacterial Symbionts of Entomopathogenic Nematodes

Entomopathogenic nematodes (Rhabditida: Steinernematidae and Heterorhabditidae) are a group of organisms capable of infecting larvae of insects living in soil, including representatives of the family Scarabaeidae. Their insecticidal activity is related to the presence of symbiotic bacteria Xenorhabdus spp. or Photorhabdus spp. in the alimentary tract, which are released into the insect body, leading to its death caused by bacterial toxins and septicemia. Although the antibacterial activities of symbionts of entomopathogenic nematodes have been well described, there is insufficient knowledge of the interactions between these bacteria and microorganisms that naturally inhabit the alimentary tract of insects infested by nematodes. In this study, 900 bacterial strains isolated from midgut samples of Amphimallon solstitiale larvae were tested for their antagonistic activity against the selected five Xenorhabdus and Photorhabdus species. Cross-streak tests showed significant antibacterial activity of 20 isolates. These bacteria were identified as Bacillus [Brevibacterium] frigoritolerans, Bacillus toyonensis, Bacillus wiedmannii, Chryseobacterium lathyri, Chryseobacterium sp., Citrobacter murliniae, Enterococcus malodoratus, Paenibacillus sp., Serratia marcescens and Serratia sp. Since some representatives of the intestinal microbiota of A. solstitiale are able to inhibit the growth of Xenorhabdus and Photorhrhabdus bacteria in vitro, it can be assumed that this type of bacterial interaction may occur at certain stages of insect infection by Steinernema or Heterorhabditis nematodes.     

A new method for fast isolation of insect antifeedant compounds from complex mixtures

Bioassay-guided isolation of bioactive natural substances requires monitoring of all fractionation and purification steps using a bioassay system. This is often a long and tedious process, especially with insect feeding bioassays. We report here a new method, based on the principle of bioautography, for a quick isolation of insect antifeedant compounds. TLC plates, after development, are coated with a thin layer of artificial diet and fed toSpodoptera litura larvae. The location of uneaten areas is then compared with theR _fvalues of the TLC spots, in order to determine rapidly the active fractions. This methods allows for a very fast determination of the most active antifeedant compounds in a complex mixture and considerably speeds up the isolation process. This new method was successfully applied in the study of antifeedant activity of several plant samples, and results are presented here for a model plant,Skimmia japonica (Rutaceae). Using this new method, the compounds responsible for the feeding-deterrent activity, three furanocoumarins (bergapten, xanthotoxin, and oxypeucedanin), were quickly and efficiently identified.     

Survey of a Salivary Effector in Caterpillars: Glucose Oxidase Variation and Correlation with Host Range

Salivary glucose oxidase (GOX) has been reported in a few insect species where it plays a role in protection against infectious disease. Our recent research has focused on the role of this salivary enzyme in the noctuid Helicoverpa zea, where it functions as an effector to suppress the induced defenses of the host plant Nicotiana tabacum. In this study, we examined the labial gland GOX activities in 23 families of Lepidoptera (85 species) and two families of plant-feeding Hymenoptera (three species). We analyzed the relationship between host breadth and GOX activities, and we found a significant relationship, where highly polyphagous species were more likely to possess relatively high levels of GOX compared to species with more limited host range. We also examined the effect of diet on GOX activity and found that the host plant had a significant effect on enzyme activity. The significance of these findings is discussed in relation to caterpillar host breadth.     

Structural Diversity and Defensive Properties of Norditerpenoid Alkaloids

We have tested the insect antifeedant and toxic activity of 43 norditerpenoid alkaloids on Spodoptera littoralis and Leptinotarsa decemlineata including eserine (physostigmine), anabasine, and atropine. Antifeedant effects of the test compounds were structure- and species-dependent. The most active antifeedants to L. decemlineata were 1,14-diacetylcardiopetaline (9) and 18-hydroxy- 14-O-methylgadesine (33), followed by 8-O-methylconsolarine (12), 14-O-acetyldelectinine (27), karakoline (7), cardiopetaline (8), 18-O-demethylpubescenine (13), 14-O-acetyldeltatsine (18), takaosamine (21), ajadine (24), and 8-O-methylcolumbianine (6) (EC50 < 1 microg/cm2). This insect showed a moderate response to atropine. S. littoralis had the strongest antifeedant response to 24, 18, 14-O-acetyldelcosine (19), and delphatine (29) (EC50 < 3 microg/cm2). None of the model substances affected the feeding behavior of this insect. The most toxic compound to L. decemlineata was aconitine (1), followed by cardiopetalidine (10) (% mortality > 60), 14-deacetylpubescenine (14), 18-O-benzoyl-18-O-demethyl-14-O-deacetylpubescenine (17), 14-O-acetyldelcosine (19), 14-deacetylajadine (25) and methyllycaconitine (30) (% mortality > 45). Orally injected S. littoralis larvae were negatively affected by 1, cardiopetaline (8), 10, 1,14-O-acetylcardiopetalidina (11), 12, 14, 1,18-O-diacetyl-19-oxo-gigactonine (41), olivimine (43), and eserine in varying degrees. Their antifeedant or insecticidal potencies did not parallel their reported nAChR binding activity, but did correlate with the agonist/antagonist insecticidal/antifeedant model proposed for nicotininc insecticides. A few compounds [14, tuguaconitine (38), 14-demethyldelboxine (40), 19, dehydrodelsoline (36), 18-O-demethylpubescenine (13), 41, 9, and delcosine (23)] had selective cytotoxic effects to ward insect-derived Sf9 cells. None were cytotoxic to mammalian CHO cells and none increased Trypanosoma cruzi mortality. The selective cytotoxic effects of some structures indicate that they can act on biological targets other than neuroreceptors.     

Antifeedants against <Emphasis Type="Italic">Hylobius abietis</Emphasis> Pine Weevils: An Active Compound In Extract of Bark of <Emphasis Type="Italic">Tilia cordata</Emphasis> Linden

Linden (Tilia cordata) bark was shown to contain an antifeedant effective against the large pine weevil, Hylobius abietis. Soxhlet extraction of inner and outer bark resulted in an extract that showed antifeedant activity in a microfeeding assay. The extract was fractionated by chromatography on silica gel using gradient elution with solvents of increasing polarity. The content of the fractions obtained was monitored by thin layer- and gas chromatography. Fractions of similar chemical composition were merged. Two of the 17 fractions showed antifeedant activity in the microfeeding assay. Nonanoic acid was identified in both of these fractions. Subsequent testing in the microfeeding assay showed that nonanoic acid possessed strong antifeedant activity against H. abietis adults.     

Antifeedant Effects of Some Novel Terpenoids on Chrysomelidae Beetles: Comparisons with Alkaloids on an Alkaloid-Adapted and Nonadapted Species

Structure–dose–feeding deterrency relationships were compared between the Colorado potato beetle, Leptinotarsa decemlineata (Say), and the western corn rootworm, Diabrotica virgifera virgifera LeConte, using 15 alkaloids, terpenoids, and phenolic derivatives. The former species, a specialist herbivore on selected alkaloid-rich Solanaceae species, was on average 100-times less sensitive to the antifeedant effects of alkaloids, but more similarly sensitive to the terpenoids and phenolics than the latter species, a generalist flower herbivore predominantly on Graminae, Cucurbitaceae, and Compositae species. Antifeedant ED₅₀ values for the potato beetle and corn rootworm, each from closely related subfamilies of Chrysomelidae, ranged over four orders of dose magnitude among the 15 compounds with major species differences in stereosensitivity to -hydrastines and analog sensitivity with the silphinenes. Extremes in sensitivity ranged from silphinene, a rare tricyclic sesquiterpene that is 53 times more active on the potato beetle to aconitine, which is 430 times more antifeedant to the corn rootworm. Among silphinene and its two hydrolysis derivatives, there was not a strong correlation between antifeedant potency and injected toxicity for the two beetle species, but there was correlation between behavioral activity and galeal taste cell electrophysiological threshold and frequency responses. That all of the established GABA- and glycinergic compounds tested were antifeedant for both species suggests a shared molecular mechanism for antifeedant taste chemoreception in these divergent Chrysomelidae species. Moreover, the wide differences in antifeedant sensitivities among these and other chrysomelids to a suite of ligand-gated ion channel antagonists implicate a common protein neuroreceptor type with extraordinary heterogeneity in beetle taste.     

(1<Emphasis Type="Italic">S</Emphasis>,3<Emphasis Type="Italic">R</Emphasis>)-<Emphasis Type="Italic">cis</Emphasis>-Chrysanthemyl Tiglate: Sex Pheromone of the Striped Mealybug, <Emphasis Type="Italic">Ferrisia virgata</Emphasis>

Derivatives of 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid (chrysanthemic acid) are classic natural pyrethroids discovered in pyrethrum plants and show insecticidal activity. Chrysanthemic acid, with two asymmetric carbons, has four possible stereoisomers, and most natural pyrethroids have the (1R,3R)-trans configuration. Interestingly, chrysanthemic acid–related structures are also found in insect sex pheromones; carboxylic esters of (1R,3R)-trans-(2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl)methanol (chrysanthemyl alcohol) have been reported from two mealybug species. In the present study, another ester of chrysanthemyl alcohol was discovered from the striped mealybug, Ferrisia virgata (Cockerell), as its pheromone. By means of gas chromatography–mass spectrometry, nuclear magnetic resonance spectrometry, and high-performance liquid chromatography analyses using a chiral stationary phase column and authentic standards, the pheromone was identified as (1S,3R)-(?)-cis-chrysanthemyl tiglate. The (1S,3R)-enantiomer strongly attracted adult males in a greenhouse trapping bioassay, whereas the other enantiomers showed only weak activity. The cis configuration of the chrysanthemic acid–related structure appears to be relatively scarce in nature, and this is the first example reported from arthropods.     

The influence of dietaryβ-carboline alkaloids on growth rate,food consumption,and food utilization of larvae ofSpodoptera exigua (Hubner)

-Carboline alkaloids are found worldwide in many plant families. Harman, harmine, and other simple -carboline alkaloids were tested for activity against a generalist phytophagous insect, the beet army worm [Spodoptera exigua (Hubner)]. Chronic dietary exposure tests (neonate to pupa) reveal potent antifeedant and possible toxic effects. Acute dietary exposure tests on fifth-instar larvae also demonstrate antifeedant activity.