When local phytotherapies meet biomedicine. Cross-sectional study of knowledge and intercultural practices against malaria in Eastern French Guiana.

ETHNOPHARMACOLOGICAL RELEVANCE: In French Guiana, traditional phytotherapies are an important part of self-healthcare, however, a precise understanding of the interactions between local phytotherapies and biomedicine is lacking. Malaria is still endemic in the transition area between French Guiana and Brazil, and practices of self-treatment, although difficult to detect, have possible consequences on the outcome of public health policies. AIM OF THE STUDY: The objectives of this research were 1) to document occurences of co-medication (interactions between biomedicine and local phytotherapies) against malaria around Saint-Georges de l'Oyapock (SGO), 2) to quantify and to qualify plant uses against malaria, 3) and to discuss potential effects of such co-medications, in order to improve synergy between community efforts and public health programs in SGO particularly, and in Amazonia more broadly. MATERIALS AND METHODS: This cross-sectional study was conducted in 2017 in SGO. Inhabitants of any age and nationality were interviewed using a questionnaire (122 questions) about their knowledge and habits regarding malaria, and their use of plants to prevent and treat it. They were invited to show their potential responses on a poster illustrating the most common antimalarial plants used in the area. In order to correlate plant uses and malaria epidemiology, all participants subsequently received a medical examination, and malaria detection was performed by Rapid Diagnostic Test (RDT) and Polymerase Chain Reaction (PCR). RESULTS: A total of 1566 inhabitants were included in the study. Forty-six percent of them declared that they had been infected by malaria at least once, and this rate increased with age. Every person who reported that they had had malaria also indicated that they had taken antimalarial drugs (at least for the last episode), and self-medication against malaria with pharmaceuticals was reported in 142 cases. A total of 550 plant users was recorded (35.1% of the interviewed population). Among them 95.5% associated pharmaceuticals to plants. All plants reported to treat malaria were shared by every cultural group around SGO, but three plants were primarily used by the Palikur: Cymbopogon citratus, Citrus aurantifolia and Siparuna guianensis. Two plants stand out among those used by Creoles: Eryngium foetidum and Quassia amara, although the latter is used by all groups and is by far the most cited plant by every cultural group. Cultivated species accounts for 91.3% of the use reports, while wild taxa account for only 18.4%. CONCLUSIONS: This study showed that residents of SGO in French Guiana are relying on both traditional phytotherapies and pharmaceutical drugs to treat malaria. This medical pluralism is to be understood as a form of pragmatism: people are collecting or cultivating plants for medicinal purposes, which is probably more congruent with their respective cultures and highlights the wish for a certain independence of the care process. A better consideration of these practices is thus necessary to improve public health response to malaria.

Efficacy of botanical insecticides from Piper species (Piperaceae) extracts for control of Ruropean chafer (Coleoptera: Scarabaeidae).

Biopesticides, including botanicals, can offer a safe and effective alternative to conventional insecticides for controlling major insect pests within an integrated pest management program. The current study highlights the practical application of a botanical insecticide for controlling a major insect pest of turfgrass: European chafer, Rhizotrogus majalis (Razoumowsky). Greenhouse and field trials were conducted to test the efficacy of a botanical formulation based on black pepper, Piper nigrum L. (Piperaceae), seed extracts to R. majalis larvae. The 7-d P. nigrum extract LC50 for R. majalis third instars was 2.5%. Successful treatment in the field was accomplished with the application of a 2% P. nigrum formulation to turfgrass infested with R. majalis second and third instars, whereas 4% extract was required in a second field trial with older third instars. The 2% pepper extract activity was comparable with the conventional insecticide diazinon in the first field trial. However, the 4% pepper extracts significantly affected the earthworm populations in treated plots compared with diazinon in the second field trail. The analysis of soil residues for piperamides in the P. nigrum extract determined a half-life of 1 - 2.6 d in the first and second field trials, respectively. This confirmed the expectation that under field conditions the residual activity would be less than conventional insecticides, thereby reducing the environmental risk associated with pesticide use. We recommend the pepper formulation for spot treatment applications when population densities reveal an epicenter of infestation rather than broadcasting over large areas, thus helping to minimize cost and negative affects on nontarget invertebrates.

Efficacy of Piper (Piperaceae) extracts for control of common home and garden insect pests.

Extracts from three species of the plant family Piperaceae, Piper nigrum [L.], Piper guineense [Schum & Thonn, and Piper tuberculatum [Jacq.], were tested for efficacy against insects from five orders. All three species contain isobutyl amides, plant secondary compounds that act as neurotoxins in insects. These materials are considered safe to mammals because Piper spp. were used for centuries for spice and medicinal purposes. When 24-h P. nigrum LC50 values were compared between common insect pests from eastern Canada and the northeastern United States, the most sensitive species in order of increasing lethal concentration were eastern tent caterpillar, Malacosoma americanum (F.) < European pine sawfly larvae, Neodiprion sertifer (Geoffroy) < spindle ermine moth larvae, Yponomeuta cagnagella [Hübner] < viburnum leaf beetle larvae, Pyrrhalta viburni [Paykull] < stripped cucumber beetle adults, Acalymma vittatum (F.) < Colorado potato beetle adults, Leptinotarsa decemlineata (Say) < Japanese beetle adults, Popillia japonica [Newman] < hairy chinch bug, Blissus leucopterus hirtis [Montandon]. The life stage tested was the point at which each species causes the greatest amount of damage to the host plant and the point at which most gardeners would likely choose to treat with a conventional synthetic insecticide. Greenhouse trials revealed that the pepper formulations also had a repellent activity, thus protecting plant leaves from 1) herbivory (lily leaf beetle, Lilioceris lilii [Scopoli], adults and larvae and stripped cucumber beetle adults) and 2) oviposition [European corn borer, Ostrinia nubilalis (Hübner)]. Combinations with other botanical extracts were additive at best in toxicity and repellent trials. Nontarget toxicity to beneficial invertebrates is a possibility because the P. nigrum LC50 for beneficial ladybird beetles was 0.2%. P. nigrum extracts can provide a reasonable level of control against lepidopteran and European pine sawfly larvae and also will work as a short-term repellent and feeding deterrent. It is recommended that the use of Piper extracts be restricted to small-scale spot treatments in residential areas where insect pest outbreaks have occurred.

Analysis of Fusarium graminearum mycotoxins in different biological matrices by LC/MS.

The purpose of this study was to develop an LC/MS assay to accurately detect three mycotoxins produced by Fusarium graminearum in various matrices. Using different LC conditions, deoxynivalenol (DON), 15-acetyldeoxynivalenol (15-ADON), and zearalenone (ZEN) were detected in four different matrices (fungal liquid cultures, maize grain, insect larvae and pig serum). The sensitivity of MS detection allowed us to detect concentrations as low as 8 ppb of DON and 12 ppb of ZEN. A very small quantity of matrix was therefore necessary for successful analysis of these toxins and a variety of experimental situations were successfully investigated using this technique. Production of 15-ADON and butenolide was monitored in a liquid culture of F. graminearum under controlled conditions. Using simple extraction procedures, the differential accumulation of DON and 15-ADON was followed in inoculated maize genotypes varying in susceptibility to F. graminearum. Toxicokinetic studies were carried out with maize insect pests reared continually on artificial diets containing ZEN and suggested that larvae may possess the ability to degrade ZEN. Finally, persistence of DON was assessed in pigs fed diet supplemented with DON, results indicated that DON accumulates quickly in pig blood and then levels decline progressively for 12 hours thereafter. The LC/MS study reported here is very useful and flexible for the detection of these mycotoxins in different media and at very low concentrations.

Botanical insecticides for controlling agricultural pests: piperamides and the Colorado Potato Beetle Leptinotarsa decemlineata say (Coleoptera: Chrysomelidae).

The efficacy of extracts from two Piperaceae species, Piper nigrum L. and P. tuberculatum Jacq. were evaluated using larvae and adults of the Colorado Potato Beetle Leptinotarsa decemlineata (Say). Young larvae and neonates were the most susceptible; a 24-h LD(50) of 0.064% extract of P. tuberculatum was determined for 4-day-old larvae, while 0.05% extract of P. nigrum reduced larval survival up to 70% within one week after treatment of potato Solanum tuberosum L. (Solanaceae) plants. When an insecticide resistant strain of L. decemlineata larvae was tested with the P. tuberculatum extract, there was less than a 2-fold tolerance ratio compared to the 22-fold tolerance ratio to cypermethrin, a pyrethroid. Older larvae, pre-pupal stage and adults, were less sensitive to the P. nigrum extracts; the 24-h LD(50) was 0.5% (95% C.I. = 0.36, 0.65). However, the same concentration was equally effective under field conditions. In the greenhouse, P. nigrum at 0.5% was as effective at reducing adult L. decemlineata feeding as combinations with 2 separate botanical mixtures, garlic and lemon grass oil. Under field conditions, the residual activity of the P. nigrum extracts was less than 3 h. When adult L. decemlineata were placed on treated plants exposed to full sunlight for 0, 1.5, and 3 h, leaf damage progressively increased as the main active compound, piperine, was found to degrade by 80% after 3 h. An in vitro polysubstrate monoxygenase (PSMO) enzyme assay, using the substrate methoxyresorufin O-demethylation (MROD), determined that the principal P. nigrum active compound, piperine, is responsible for inhibition of that specific enzyme. The results suggest that Piper extracts could be used effectively as contact botanical insect control agents to protect potato plants from developing L. decemlineata larvae at concentrations less than 0.1%. There is also potential for Piper extracts to control insecticide resistant populations in conjunction with other integrated pest management (IPM) strategies used in conventional and organic agriculture.

Traditionally-used antimalarials from the Meliaceae.

A quantitative ethnobotanical approach to antimalarial drug discovery led to the identification of Lansium domesticum Corr. Ser. (Meliaceae) as an important antimalarial used by Kenyah Dyak healers in Indonesian Borneo. Triterpenoid lansiolides with antimalarial activity were isolated from the bark and shown to have activity in both in vitro bioassays with Plasmodium falciparum, and in mice infected with P. berghei. A survey of African and tropical American Meliaceae led to further development of the limonoid gedunin from the traditionally used medicinal plants, tropical cedar, Cedrela odorata L., and neem, Azadirachta indica A. Juss. Gedunin has significant in vitro activity but initially showed poor in vivo activity. In vivo activity was improved by (1) incorporation into an easy to absorb suspension, (2) preparation of a more stable compound, 7-methoxygedunin; and (3) synergism with dillapiol, a cytochrome P450 3A4 inhibitor. The results show the potential for both antimalarial drug and phytomedicine development from traditionally used plants.

Dehydrodimers of Ferulic Acid in Maize Grain Pericarp and Aleurone: Resistance Factors to Fusarium graminearum.

ABSTRACT The relationship between the primary cell wall phenolic acids, dehydrodimers of ferulic acid, and maize grain resistance to Fusarium graminearum, the causal agent of gibberella ear rot, was investigated. Concentrations of dehydrodimers of ferulic acid were determined in the pericarp and aleurone tissues of five inbreds and two hybrids of varying susceptibility and in a segregating population from a cross between a resistant and susceptible inbred. Significant negative correlations were found between disease severity and diferulic acid content. Even stronger correlations were observed between diferulic acid and the fungal steroid ergosterol, which is an indicator of fungal biomass in infected plant tissue. These results were consistent over two consecutive field seasons, which differed significantly for temperature and rainfall during pollination, the most susceptible stage of ear development. No correlation was found between the levels of these phenolics and deoxynivalenol levels. This is the first report of in vivo evidence that the dehydrodimers of ferulic acid content in pericarp and aleurone tissues may play a role in genotypic resistance of maize to gibberella ear rot.

Synergistic insecticidal mode of action between sesquiterpene lactones and a phototoxin, alpha-terthienyl.

The synergistic insecticidal action of characteristic defensive substances produced by the plant family Asteraceae was investigated under controlled laboratory conditions. Sesquiterpene lactones isolated from Asteraceae that may form, through a Michael addition process, conjugates with glutathione were administered in a meridic diet to a herbivorous insect, Manduca sexta. By administering sesquiterpenes, variable in vivo reduced glutathione levels were observed in the insect larvae. When the Asteraceae-derived photooxidant alpha-terthienyl was co-administered, lipid peroxidation and larval mortality were significantly enhanced in the treated groups of insects with lowered in vivo glutathione levels.

Insecticidal defenses of Piperaceae from the neotropics.

Insecticidal and growth-reducing properties of extracts of 14 species of American neotropical Piperaceae were investigated by inclusion in diets of a polyphagous lepidopteran, the European corn borer,Ostrinia nubilalis. Nutritional indices suggested most extracts acted by postdigestive toxicity.Piper aduncum, P. tuberculatum, andP. decurrens were among the most active species and were subjected to bioassay-guided isolation of the active components. Dillapiol was isolated from the active fraction ofP. aduncum, piperlonguminine was isolated fromP. tuberculatum, and a novel neolignan fromP. decurrens. The results support other studies on Asian and AfricanPiper species, which suggest that lignans and isobutyl amides are the active defence compounds in this family.

Insecticide synergists: role, importance, and perspectives.

Synergists have been used commercially for about 50 years and have contributed significantly to improve the efficacy of insecticides, particularly when problems of resistance have arisen. In the current article we review the nature, mode of action, role in resistance management, natural occurrence, and significance in research of insecticide synergists. These natural or synthetic chemicals, which increase the lethality and effectiveness of currently available insecticides, are by themselves considered nontoxic. The mode of action of the majority of synergists is to block the metabolic systems that would otherwise break down insecticide molecules. They interfere with the detoxication of insecticides through their action on polysubstrate monooxygenases (PSMOs) and other enzyme systems. The role of synergists in resistance management is related directly to an enzyme-inhibiting action, restoring the susceptibility of insects to the chemical, which would otherwise require higher levels of the toxicant for their control. For this reason synergists are considered straightforward tools for overcoming metabolic resistance, and can also delay the manifestation of resistance. However, the full potential of these compounds may not have been realized in resistance management. Synergists have an important role to play in the ongoing investigation of insecticide toxicity and mode of action and the nature of resistance mechanism. They also can be used in understanding the effects of other xenobiotics in non-target organisms. The search for and the need of new molecules capable of synergizing existing or new pesticides has reactivated the identification and characterization of secondary plant compounds possessing such activity. Plants do possess and utilize synergists to overcome the damage produced by phytophages. This has to be exploited in pest management programs. Hopefully, it will lead to a new perspective on the nature and significance of synergism.

Behavioral responses of western corn rootworm larvae to naturally occurring and synthetic hydroxamic acids.

Hydroxamic acids have been shown to be toxic to many pest insects and pathogens. In this study, the behavioral responses of western corn rootworm larvae to naturally occurring and synthetic hydroxamic acids were investigated. In a choice test between corn roots treated with hydroxamic acids and roots treated with distilled water (control), western corn rootworm larvae chose to burrow into the control roots significantly more often than compoundtreated roots. In addition, when corn roots were treated with different hydroxamic acids in a designed searching-behavior test, neonate larvae of western corn rootworm responded by significantly reducing the number of turns, while the area searched and locomotor rate significantly increased. The responses were dependent on the concentrations of the test compounds. These results suggested that hydroxamic acids were acting as behavior-modifying and possibly feeding-deterrent chemicals.

The protective effect of antioxidants to a phototoxin-sensitive insect herbivore,Manduca sexta.

Photo-activated plant secondary compounds have been shown to be toxic to many organisms including insects. Insect defenses include behavioral mechanisms such as light avoidance, as well as specific biochemical defenses such as antioxidants and antioxidant enzymes. These antioxidant defenses eliminate or quench the deleterious singlet oxygen and free radicals formed by these phototoxins. In this paper we examined the role of dietary antioxidants in protecting the phototoxin-sensitive insect herbivoreManduca sexta. Elevated dietary levels of the lipid-soluble antioxidantsΒ-carotene and vitamin E resulted in a concentration-dependent reduction in the mortality associated with treatment ofM. sexta larvae with the phototoxic thiopheneα-terthienyl. Elevated levels of dietary ascorbic acid had no effect, whereas reduced levels greatly increased the toxicity ofα-terthienyl. Tissue levels of antioxidants were shown to increase substantially in larvae fed antioxidant-supplemented diets. The results suggest that the ability to absorb and utilize plant-derived antioxidants could be an important defense against photo-activated plant secondary compounds and may have allowed some insects to exploit phototoxic plants.

Correlation of phenolic acid content of maize to resistance toSitophilus zeamais, the maize weevil, in CIMMYT'S collections.

The (E)-ferulic acid content of the grain of nine populations of land races of maize derived from CIMMYT's collections was found to be negatively correlated to susceptibility characteristics towards the maize weevilSitophilus zeamais. Correlation coefficients for six susceptibility parameters and (E)-ferulic acid content were significant and ranged from -0.58 to -0.79. A multiple regression analysis by the SAS forward procedure using the primary seed characteristics associated with susceptibility indicated that the ferulic acid content was the only significant factor in explaining variation in at least two susceptibility parameters: the Dobie index and adult preference. In 15 CIMMYT pools, correlations between four susceptibility parameters and (E)-ferulic acid content were also significant (-0.76 to -0.81). The results suggest that phenolic acid content is a leading indicator of grain resistance or susceptibility to insects and may represent a newly identified mechanism of resistance.

Field responses of certain forest Coleoptera to conifer monoterpenes and ethanol.

Field experiments using baited sticky stovepipe traps and Lindgren multiple funnel traps were done near Chalk River, Ontario, Canada, to determine the effects of conifer monoterpenes (α-pinene, ß-pinene, myrcene, limonene, camphene and carene) and ethanol on the number of beetles captured. Several species of conifer-feeding beetles were attracted to the monoterpenes or to monoterpenes and ethanol, including species in the families Cerambycidae (Asemum striatum, Acmaeops proteus, Xylotrechus undulatus, Monochamus scutellatus), Curculionidae (Pissodes strobi, Hylobius pales), and Scolytidae (Dryocetes autographus, Ips grandicollis). Species of Buprestidae generally did not respond to the monoterpenes or to ethanol. Species of Cleridae (Thanasimus dubius, Enoclerus nigripes rufiventris, Enoclerus nigrifrons gerhardi) which are predators of conifer bark beetles were attracted to the monoterpenes. Synergism between monoterpenes and ethanol was evident forM. scutellatus, H. pales, andD. autographus. While α-pinene was the most potent attractant for most beetle species, monoterpenes other than α-pinene synergized attraction to ethanol forD. autographus. Attraction of beetles to commercial turpentine and ethanol did not differ significantly from attraction to a pure monoterpene blend and ethanol.

Toxicokinetics of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) in the European corn borer,Ostrinia nubilalis (Hübner).

2,4-Dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA), the major hydroxamic acid present in corn, and its tritiated derivative, were prepared synthetically for use in the determination of the toxicokinetics of this insect deterrent in the European corn borer (ECB),Ostrinia nubilalis. In growth studies with DIMBOA (0, 0.05, 0.2, and 0.5 mg/g diet), the mean time to pupation and adult emergence were significantly lengthened by an increase in concentration. Pupal and adult weights, for both female and male, decreased with an increase in concentration. Increased larval and pupal mortality occurred at the highest concentration of DIMBOA. DIMBOA, at concentrations of 0.2 and 0.5 mg/g diet, resulted in a decrease in the number of egg masses produced per female, and at 0.5 mg/g diet, in a decrease in the number of eggs per egg mass. Larvae fed from the neonate stage on a diet containing 0.2 mg [(3)H]- + [(1)H]DIMBOA/g diet showed an increase in the content of label from fourth to fifth instar, but levels declined at pupation and emergence. A large amount of the labeled compounds was excreted by the insect in the pupal case. In dose-related studies, both uptake and excretion increased with an increase in concentration of DIMBOA (0.05, 0.2, 0.4 mg/g diet), while a body burden (concentration in the tissues/concentration in the frass) of approximately 0.25 was maintained for all concentrations. At the highest dose of DIMBOA (0.4 mg/g), the ECB increased consumption, possibly to compensate for the toxic effects of the compound. In topical application studies, elimination of the labeled compound in the frass was rapid, reaching 65% by 4 hr and 88% by 48 hr. Accumulation of label in tissues other than hemolymph was low. The results show that the ECB does possess adaptive mechanisms to deal with the effects of this host-derived compound.

Toxicity and toxicokinetics of 6-methoxybenzoxazolinone (MBOA) in the european corn borer,Ostrinia nubilalis (Hübner).

The maize-derived secondary chemical 6-methyoxybenzoxazoii-none (MBOA) and a tritiated derivative were prepared synthetically for a detailed examination of their toxicity and toxicokinetics in the European corn borer (ECB),Ostrinia nubilalis. During feeding trials with MBOA incorporated into meridic diets (at 0, 0.5, 1.5, 2.5, and 4.0 mg/g diet), the mean time to pupation and adult emergence was significantly lengthened at concentrations of 1.5 mg MBOA/g diet and above. Increased mortality occurred at concentrations at 1.5 mg/g and above. A decrease in the sex ratio (female/ total) and fecundity was observed at concentrations of 0.5 mg/g and above. The latter observations represent new biological effects related to MBOA. In tracer studies, both uptake and excretion of MBOA administered in diets to larvae increased linearly with concentration. Body burden values indicated that the ECB larvae were capable of excreting enough compound to maintain total tissue levels at approximately 50% of the dietary concentration. Total amount of label increased with larval stage, but decreased in adults due to a large amount of label eliminated in the pupal case. In topical application studies, elimination of the label in the frass was rapid, reaching 60% by 6 hr and 82% of applied dose by 24 hr. Accumulation of label in tissues other than hemolymph was small. The results show that MBOA is toxic to ECB, but the insect has efficient methods for minimizing these effects.

Comparative effects of two plant secondary metabolites on host-parasitoid association.

Two plant-derived allelochemicals, berberine and α-terthienyl (α- T), were tested for their effects on the European corn borer,Ostrinia nubilalis, and its endoparasitoidDiadegma terebrans. The compounds were administered to the host insect in meridic diets, and the responses of the host larvae and parasitoids reared from treated hosts were measured in terms of growth parameters and survival. InO. nubilalis, survival to pupation and adult emergence were reduced significantly by the inclusion of berberine and α-T in larval diets at a concentration of 100 µg/g. However, in the parasitoid, adverse effects were much more apparent with the α-T treatment than with the berberine treatment. α-T and one of its metabolites were found in host larvae and in emerged adult parasitoids and their cocoons. Berberine residues were not detected. The implications of these responses to compounds of widely differing physiological properties are discussed with reference to host-plant resistance and biological control.

Mode of action of the sesquiterpene lactone, tenulin, from Helenium amarum against herbivorous insects.

Tenulin [1], a sesquiterpene lactone from Helenuim amarum, is a potent antifeedant to the European corn borer Ostrinia nubilalis. At 3 mumol/g in artificial diets, 1 reduced growth and delayed larval development of O. nubilalis and the variegated cutworm Peridroma saucia larvae. An especially pronouned carry-over effect in O. nubilis was substantial reduction in fecundity of adult moths resulting from treated larvae. The LD50 (lethal dose for 50% mortality) of 1 by injection in the migratory grasshopper Melanoplus sanguinipes was 0.88 mumol/insect. Toxicity in M. sanguinipes was antagonized by co-administration of cysteine, suggesting that the cyclopentenone group of tenulin undergoes Michael addition of biological nucleophiles in vivo. This mechanism was partially confirmed by the finding that only tenulin analogues capable of acting as electrophic acceptors had significant antifeedant activity.

Factors contributing to resistance of exotic maize populations to maize weevil,Sitophilus zeamais.

Factors contributing to resistance of maize to infestation by the corn weevilSitophilus zeamais were investigated in four populations of indigenous and improved maize from Belize. Resistance was related to the antifeedant properties of grain as well as sugar content and mechanical hardness. Grain extracts of all populations of maize significantly reduced insect feeding on treated artificial diets when compared to control diets. Consumption of treated diets was negatively correlated with phenolic content of the grain extract. An analysis by GC-MS indicated that ferulic acid andp-coumaric acid were the principal phenolics present in the extracts, and insect feeding was strongly deterred when pure substances were added to insect diets. Fluorescence associated with ferulic acid and related compounds in grain sections was located in the pericarp and aleurone layer and was especially intense in the most resistant grain variety.

Light-mediated allelochemical effects of naturally occurring polyacetylenes and thiophenes from asteraceae on herbivorous insects.

Polyacetylenes and their thiophene derivatives, characteristic secondary metabolites of the Asteraceae, were examined for their effects on herbivorous insects. Three thiophenes (a monothiophene, a bithiophene, and α-terthienyl) and four polyacetylenes (phenylheptatriyne, phenylheptadiynene, phenylheptadiyene acetate, and matricaria lactone) were studied for their phototoxicity and light-independent toxicity to (1) a polyphagous lepidopteran,Ostrinia nubilalis, whose host range includes a number of phototoxic Asteraceae, (2) a polyphagous lepidoteran,Euxoa messoria, whose host range includes very few species of Asteraceae, and (3) an oligophagous lepidopteran,Manduca sexta, which is a specialist on Solanaceae. Several compounds were phototoxic toM. sexta andE. messoria even at very low irradiance levels, but behavioral adaptations, including spinning silk and boring into diet, allowedO. nubilalis to avoid photosensitization. Light-independent activity of the compounds to all three species involved feeding deterrence increasing in the orderO. nubilalis, E. messoria, andM. sexta, and longterm metabolic toxicity in the form of impaired nutrient utilization. The biosynthetically derived thiophenes were more toxic than their acetylenic precursors, and toxicity increased with increasing number of thiophene rings. The results are discussed in terms of plant-insect coevolution.