Essential Oils of Myrtaceae Species Growing Wild in Tunisia: Chemical Variability and Antifungal Activity Against Biscogniauxia mediterranea,the Causative Agent of Charcoal Canker

The chemical composition of five Eucalyptus species and five Myrtus communis L. populations was investigated using GC/MS and GC‐FID. For Eucalyptus essential oils, 32 compounds, representing 88.56 – 96.83% of the total oil according to species, were identified. The main compounds were 1,8‐cineole, α‐pinene, p‐cymene, γ‐gurjunene, α‐aromadendrene, and β‐phellandrene. For Myrtle essential oils, 26 compounds, representing 93.13 – 98.91% of the total oil were identified. α‐Pinene, 1,8‐cineole, linalool, and myrtenyl acetate were found to be the major compounds. Principal component analysis (PCA) showed chemical differentiation between Eucalyptus species and between Myrtle populations. Biscogniauxia mediterranea, the causative agent of charcoal canker, was identified according to its morphological and molecular characteristics. Essential oils of the investigated Eucalyptus species and Myrtle populations were tested for their antifungal capacity against this fungus. The antifungal activity varied according to the essential oil composition. Biscogniauxia mediterranea exhibited powerful resistance to some essential oils including them of Eucalyptus lehmannii and Eucalyptus sideroxylon but it was very sensitive to Eucalyptus camaldulensis oil (IC₅₀ = 3.83 mg/ml) and M. communis oil from Zaghouan (IC₅₀ = 1 mg/ml). This sensitivity was found to be correlated to some essential oil compounds such as p‐cymene, carvacrol, cuminaldehyde, and linalool.     

Chemistry matters: biological activity of Eucalyptus essential oils on mosquito larval mortality

The mosquito Aedes aegypti L. (Diptera: Culicidae) is a vector of arboviral diseases such as dengue fever. Currently, the main approach to mosquito control is the application of synthetic insecticides, which can lead to negative environmental impacts and insecticide resistance in mosquito populations. As such, there has been increased interest in developing alternative methods for control of vector populations such as utilizing plant compounds that act as larvicides. The aim of this work is to evaluate the effectiveness of Eucalyptus sp. (Myrtaceae) essential oils for control of Ae. aegypti larvae. The essential oils of seven Eucalyptus species and hybrids were extracted by hydrodistillation and analyzed by gas chromatography coupled to mass spectrometry. The essential oils were further diluted in water with acetone (0.40%) at the following concentrations: 100, 50, 25, and 10 μg ml⁻¹. Mortality trials were conducted in plastic containers with a solution of ultrapure water and 200 μl of diluted oil for a total volume of 50 ml per treatment. The experiments for each Eucalyptus species/hybrid and concentration were performed in triplicate, using a control containing only water and acetone. Twenty larvae were added to each container and mortality was recorded at 1, 2, 4, and 24 h. The Eucalyptus essential oils showed larvicidal activity in most of the evaluated concentrations, mainly at 50 and 100 μg ml⁻¹. Eucalyptus benthamii Maiden & Cambage and the hybrid Urograndis displayed the highest larvicidal potential (100% at 24 h) in the 100 μg ml⁻¹ treatment. Larval mortality of Ae. aegypti showed a positive correlation with the compounds γ-, o-cymol, o-cymene, terpineol, 3-dodecylfuran-2,5-dione, α-pinene, globulol, and ledol. The most abundant compounds identified in the essential oils were 1,8-cineole and α-pinene. These results highlight the potential of using Eucalyptus essential oils for the isolation of natural larvicidal products.     

The Chemical Diversity of Eucalyptus spp. Essential Oils from Plants Grown in Brazil

A chemical analysis of essential oils from leaves of eleven Eucalyptus L’Herit taxa, grown in Viçosa, Brazil were carried out. The identification and quantification of essential oils constituents were carried out by GC‐FID and GC/MS. The leaves of E. camaldulensis and E. tereticornis presented the highest oil content (3.00% and 2.30% respectively). In total, 48 compounds were identified in the oils. Higher levels of 1,8‐cineole were found for oils produced by E. microcorys (66.2%), E. urophylla (65.4%) and E. camaldulensis (44.8%) and the hybrid E. urophylla × E. grandis (33.0%). The oil from E. saligna was composed mainly by α‐pinene (92.3%). High concentrations of α‐phellandrene were found in the oils produced by E. camaldulensis (22.9%) and E. robusta (36.6%). The oils from E. grandis and E. pilularis were rich in p‐cymene (59.5% and 46.0%, respectively). Samples with high levels of 1,8‐cineole were classified by principal component analysis (PCA) using the accumulated variance of the PC1 and PC2 into major groups. Other samples were grouped based on their content of p‐cymene; α‐phellandrene, α‐ and β‐eudesmol; α‐pinene. The PCA allowed the separation and classification of samples with the highest levels of different compounds, a procedure that can help in the decision of grouping oils from different sources for industrial use.     

Chemical composition,insecticidal and biochemical effects of Melaleuca alternifolia essential oil on the Helicoverpa armigera

Pesticide resistance has developed as a result of long‐term and extensive use of chemical pesticides. Essential oils from aromatic plants may provide a new and safe alternative to conventional insecticides. In this study, the insecticidal activities of the essential oil of Melaleuca alternifolia and their chemical constituents against Helicoverpa armigera Hubner were investigated, and the underlying mechanisms were studied. The essential oil showed distinct antifeedant (AFC₅₀ = 8.93 mg/ml) and good contact (LD₅₀ = 50.28 μg/larva) activities against H. armigera at 24 hr. Ten chemical components were identified using a gas chromatograph/mass spectrometer, and mainly included terpinen‐4‐ol (40.09%), γ‐terpinene (21.85%), α‐terpinene (11.34%), α‐terpineol (6.91%), α‐pinene (5.86%), terpinolene (3.24%) and 1,8‐cineole (1.83%). Among them, five components were determined and results showed that these constituents possessed obvious antifeedant activities. The activities of acetylcholinesterase and glutathione S‐transferase were notably inhibited by the essential oil, as compared with the control, with strong dose‐ and time‐dependent effects. The results provide a basis for their development and utilization in the control of insects in the future.     

Variation in Volatile Leaf Oils of Eleven Eucalyptus Species Harvested from Korbous Arboreta (Tunisia)

Hydrodistillation of the dried leaves of eleven species of the genus Eucalyptus L 'Hér ., i.e., E. astringens Maiden , E. camaldulensis Dehnh ., E. diversifolia Bonpl ., E. falcata Turcz ., E. ficifolia F. Muell ., E. gomphocephala DC., E. lehmannii (Schauer ) Benth ., E. maculata Hook ., E. platypus Hook ., E. polyanthemos Schauer, and E. rudis Endl ., harvested from Korbous arboreta (region of Nabeul, northeast of Tunisia) in April 2006, afforded essential oils in yields varying from 0.1±0.1 to 3.8±0.1%, dependent on the species. E. astringens and E. ficifolia showed the highest and the lowest mean percentage of essential oil amongst all the species examined, respectively. Analysis by GC (RI) and GC/MS allowed the identification of 138 components, representing 74.0 to 99.1% of the total oil. The contents of the different samples varied according to the species. The main components were 1,8‐cineole, followed by trans‐pinocarveol ( 1 ), spathulenol ( 2 ), α‐pinene, p‐cymene, (E,E)‐farnesol, cryptone, globulol ( 3 ), β‐phellandrene, α‐terpineol, viridiflorol, and α‐eudesmol. The principal‐component and the hierarchical‐cluster analyses separated the eleven Eucalyptus leaf essential oils into seven groups, each constituting a chemotype.     

Intraspecific Variability of the Essential Oil of Ziziphora clinopodioides ssp. rigida from Iran

Hydrodistillated essential oils of Ziziphora clinopodioides ssp. rigida from nine populations of the Lashgardar protected region (Hamedan Province, Iran) were analyzed by using GC and GC/MS techniques to determine the intraspecific chemical variability. Altogether, 39 compounds were identified in the oils, and a relatively high variation in their contents was found. The main constituents of the essential oils were pulegone (0.7–44.5%), 1,8‐cineole (2.1–26.0%), neomenthol (2.5–22.5%), 4‐terpineol (0.0–9.9%), 1‐terpineol (0.0–13.2%), neomenthyl acetate (0.0–7.1%), and piperitenone (0.0–5.4%). For the determination of the chemotypes and the intraspecific chemical variability, the essential oil components were subjected to cluster analysis (CA). The five different chemotypes characterized were Chemotype I (pulegone/neomenthol), Chemotype II (pulegone), Chemotype III (pulegone/1,8‐cineole), Chemotype IV (neomenthol), and Chemotype V (1,8‐cineole/4‐terpineol).     

Terpenes associated with resistance against the gall wasp,Leptocybe invasa,in Eucalyptus grandis

Leptocybe invasa is an insect pest causing gall formation on oviposited shoot tips and leaves of Eucalyptus trees leading to leaf deformation, stunting, and death in severe cases. We previously observed different constitutive and induced terpenes, plant specialized metabolites that may act as attractants or repellents to insects, in a resistant and susceptible clone of Eucalyptus challenged with L. invasa. We tested the hypothesis that specific terpenes are associated with pest resistance in a Eucalyptus grandis half‐sib population. Insect damage was scored over 2 infestation cycles, and leaves were harvested for near‐infrared reflectance (NIR) and terpene measurements. We used Bayesian model averaging for terpene selection and obtained partial least squares NIR models to predict terpene content and L. invasa infestation damage. In our optimal model, 29% of the phenotypic variation could be explained by 7 terpenes, and the monoterpene combination, limonene, α‐terpineol, and 1,8‐cineole, could be predicted with an NIR prediction ability of  .67. Bayesian model averaging supported α‐pinene, γ‐terpinene, and iso‐pinocarveol as important for predicting L. invasa infestation. Susceptibility was associated with increased γ‐terpinene and α‐pinene, which may act as a pest attractant, whereas reduced susceptibility was associated with iso‐pinocarveol, which may act to recruit parasitoids or have direct toxic effects.     

Larvicidal effects of some essential oils against Aedes aegypti (L.), the vector of dengue fever in Saudi Arabia

Essential oils are very popular among organic growers because they are ecologically safe, do not have mammalian toxicity, and cannot be resistant to a variety of contaminants. Four essential oils, Lemon, Lavender, Peppermint, and Neem, were tested for larvicide efficacy against the dengue fever vector Aedes aegypti larvae under laboratory conditions using dipping bioassay techniques. Among the essential oils tested, lemon, peppermint, and lavender oils showed high larvicidal activity against larvae of Ae. aegypti. Lemon oil showed the highest effects (LC₅₀ 10.676 ppm), while Peppermint, Lavender and Neem oil showed the lowest effects (LC₅₀ 21.380, 29.818 and 38.058 ppm, respectively). As a result, the mixture of lemon oil (LC₅₀) with Peppermint oil (LC₂₅) showed the highest co-toxicity factor, whereas the mixture of Lemon oil (LC₅₀) with Diesel oil (LC₂₅) showed the lowest co-toxicity factor. Based on the results of this study, it appears that essential oils may be useful as larvicides against Ae. aegypti larvae. In search of new natural larvicides, these compounds may provide an alternative to Synthetic insecticides as these are environmentally safe insecticides.     

Excito‐repellency of essential oils against an Aedes aegypti (L.) field population in Thailand

An investigation of the behavioral responses of Aedes aegypti (= Stegomyia aegypti) to various concentrations of essential oils (2.5, 5, and 10%) extracted from hairy basil (Ocimum americanum Linn), ginger (Zingiber officinale Roscoe), lemongrass (Cymbopogon citratus Stapf), citronella grass (Cymbopogon nardus Rendle), and plai (Zingiber cassumunar Roxb) were performed using an excito‐repellency test chamber. Results showed that Ae. aegypti exhibited varying levels of escape response in both the contact and noncontact chambers in response to different essential oils. The magnitude of the behaviors changed in a dose‐response fashion depending on the percent volume to volume concentration of oil used. A 2.5% concentration of hairy basil oil produced a significantly greater escape response compared to the other extracts at the same concentration (P< 0.05). Oils of ginger, lemongrass, and citronella produced stronger irritant and repellent responses at the median 5% concentration compared to the lowest and highest concentrations. There was marked suppression of escape for both contact and noncontact tests using 10% concentrations of hairy basil, lemongrass, and citronella, with high knockdown for all three oils after 30 min. Hairy basil and lemongrass had the highest insecticidal activity to Ae. aegypti, with LC₅₀ values of 6.3 and 6.7 percent, respectively. We conclude that the essential oils from native plants tested, and likely many other extracts found in plants, have inherent repellent and irritant qualities that should to be screened and optimized for their behavior‐modifying properties against Ae. aegypti and other biting arthropods of public health and pest importance.     

Variation in volatile leaf oils of five Eucalyptus species harvested from Jbel Abderrahman arboreta (Tunisia)

Hydrodistillation of the dried leaves of five species of the genus Eucalyptus L' Hér ., viz., E. dundasii Maiden , E. globulus Labill ., E. kitsoniana Maiden , E. leucoxylon F. Muell ., and E. populifolia Hook ., harvested from Jbel Abderrahman arboreta (region of Nabeul, northeast of Tunisia) in April 2006, afforded essential oils in yields varying from 0.9±0.3 to 3.8±0.6%, dependent on the species. E. globulus and E. Kitsoniana provided the highest and the lowest percentage of essential oil amongst the species examined, respectively. Analysis by GC (RI) and GC/MS allowed the identification of 127 compounds, representing 93.8 to 98.7% of the total oil composition. The contents of the different samples varied according to the species. The main components were 1,8‐cineole ( 2 ; 4.7–59.2%), followed by α‐pinene ( 1 ; 1.9–23.6%), trans‐pinocarveol ( 6 ; 3.5–21.6%), globulol ( 8 ; 4.3–12.8%), p‐cymene ( 3 ; 0.5–6.7%), α‐terpineol (1.5–4.5%), borneol (0.2–4.4%), pinocarvone (1.1–3.8%), aromadendrene (1.4–3.4%), isospathulenol (0.0–1.9%), fenchol ( 4 ; 0.1–2.5%), limonene (1.0–2.4%), epiglobulol (0.6–2.1%), viridiflorol ( 9 ; 0.8–1.8%), and spathulenol (0.1–1.6%). E. leucoxylon was the richest species in 2 . Principal component analysis (PCA) and hierarchical cluster analysis (HCA) separated the five Eucalyptus leaf essential oils into four groups, each constituting a chemotype.     

Chemical composition and larvicidal activity of essential oils of three Artemisia species

Aedes aegypti L. (Diptera: Culicidae) is a vector for serious diseases in tropical regions. This pest is mainly controlled by commercial larvicides but the application of such products has led to environmental problems. Essential oils (EO) have been consistently reported as molecules with insecticidal activity and can be used to produce more environmentally friendly larvicides in the control of A. aegypti. In this study, the larvicidal effect of essential oils (EO) from the leaves of three Artemisia species was evaluated against A. aegypti. The oils were obtained from steam distillation and their chemical composition was determined by gas chromatography–mass spectrometry. The EO of Artemisia camphorata was the most active in the screening bioassay and presented LC₅₀ and LC₉₅ of 64.95 and 74.18 μg ml⁻¹, respectively. In addition, we found that germacrene D-4-ol was the constituent responsible for the toxicity of this EO. Artemisia camphorata EO and its major constituent, germacrene D-4-ol, are promising for the development of natural larvicides against A. aegypti.     

Corymbia leaf oils,latitude, hybrids and herbivory: A test using common‐garden field trials

Foliar oils, particularly monoterpenes, can influence the susceptibility of plants to herbivory. In plants, including eucalypts, monoterpenes are often associated with plant defence. A recent analysis revealed an increase in foliar oil content with increasing latitudinal endemism, and we tested this pattern using three eucalypt taxa comprising a latitudinal replacement cline. We also examined the relative concentrations of two monoterpenes (α‐pinene and 1,8‐cineole), for which meta‐analyses also showed latitudinal variation, using hybrids of these three taxa with Corymbia torelliana. These, and pure C. torelliana, were then assessed in common‐garden field plots for the abundance and distribution of herbivory by four distinct herbivore taxa. Differing feeding strategies among these herbivores allowed us to test hypotheses regarding heritability of susceptibility and relationships to α‐pinene and 1,8‐cineole. We found no support for an increase in foliar oil content with increasing latitude, nor did our analysis support predictions for consistent variation in α‐pinene and 1,8‐cineole contents with latitude. However, herbivore species showed differential responses to different taxa and monoterpene contents. For example, eriophyid mites, the most monophagous of our censused herbivores, avoided the pure species, but fed on hybrid taxa, supporting hypotheses on hybrid susceptibility. The most polyphagous herbivore (leaf blister sawfly Phylacteophaga froggatti) showed no evidence of response to plant secondary metabolites, while the distribution and abundance patterns of Paropsis atomaria showed some relationship to monoterpene yields.     

Variation in Volatile Leaf Oils of 13 Eucalyptus Species Harvested from Souinet Arboreta (Tunisia)

Hydrodistillation of the dried leaves of 13 species of the genus Eucalyptus L' Hér ., viz., E. bicostata Maiden, Blakely & Simmonds , E. cinerea F. Muell . ex Benth ., E. exerta F. Muell ., E. gigantea Hook . f ., E. gunnii Hook . f ., E. macarthurii Deane & Maiden ., E. macrorrhyncha F. Muell ., E. maidenii F. Muell ., E. odorata Behr ., E. pauciflora Sieber ex Sprengel , E. sideroxylon A. Cunn . ex Woolls , E. tereticornis Sm ., and E. viminalis Labill ., harvested from Souinet arboreta (region of Ain Draaham, north of Tunisia) in June 2006, afforded essential oils in yields varying from 0.5±0.2 to 3.9±0.4%, dependent on the species. E. cinerea and E. exerta provided the highest and the lowest percentage of essential oil amongst all the species examined, respectively. Analysis by GC (RI) and GC/MS allowed the identification of 142 components, representing 81.5 to 98.9% of the total oil. The contents of the different samples varied according to the species. The main components were 1,8‐cineole ( 1 ), followed by cryptone, spathulenol ( 4 ), p‐cymene ( 2 ), viridiflorol ( 6 ), globulol ( 7 ), β‐eudesmol, α‐terpineol ( 5 ), limonene ( 8 ), D ‐piperitone, α‐pinene ( 3 ), cuminal, and γ‐eudesmol. The principal component and the hierarchical cluster analyses separated the 13 Eucalyptus leaf essential oils into three groups, each constituting a chemotype.     

Essential Oil and Bioactive Compounds Variation in Myrtle (Myrtus communis L.) as Affected by Seasonal Variation and Salt Stress

The effect of different NaCl concentrations (control, 2, 4 and 6 dS/m) and three harvesting times in different seasons including spring (9 April), summer (5 July), and fall (23 September) was evaluated on essential oil (EO) yield, composition, phenolic, flavonoid content, and antioxidant activity of myrtle. Essential oil yield ranged from 0.2% in control and fall to 1.6% in moderate salinity (4 dS/m) and spring season. The main constituents obtained from gas chromatography/mass spectrometry analysis were α‐pinene, 1,8‐cineole, limonene, linalool, α‐terpineol, and linalyl acetate in which α‐pinene ranged from 11.70% in moderate and fall to 30.99% in low salinity (2 dS/m) and spring, while 1,8‐cineole varied from 7.42% in high salinity (6 dS/m) and summer to 15.45% in low salinity and spring, respectively. Salt stress also resulted in an increase in total phenolic, flavonoid content, and antioxidant activity. The highest antioxidant activity based on DPPH radical scavenging activity, reducing power (FTC) and β‐carotene/linoleic acid model systems was found in plants harvested in spring and summer in high stress condition. The lowest IC₅₀ values obtained in 6 dS/m in spring (375.23 μg/ml) followed by summer (249.41 μg/ml) and fall (618.38 μg/ml). Eight major phenolic and flavonoid compounds were determined in three harvesting times using high performance liquid chromatography analysis. In overall, late harvesting time of myrtle in fall can lead to reduce the most of major EO components, while it can improve the amount of phenolic acids.     

Forty‐two compounds in eleven essential oils elicit antennal responses from Aedes aegypti

Essential oils of various plants can be effective at repelling mosquitoes. The repellent properties are often ascribed to their dominant constituents. Our objective was to analyse several essential oils by coupled gas chromatographic‐electroantennographic detection (GC‐EAD) on the premise that those compounds that are detected by the antennae of the yellow fever mosquito, Aedes aegypti L. (Diptera: Culicidae), are candidate repellents even though they may be minor constituents and thus be overlooked in GC‐mass spectrometric analyses of essential oils. In the essential oils of catnip, cinnamon, citronella, cumin, eucalyptus, geranium, ginger, melissa, peppermint, rosemary, and thyme, 42 components induced antennal responses, most commonly β‐caryophyllene, linalool, 1,8‐cineole, geraniol, and geranial. Some of these 42 components are known insect repellents, indicating that GC‐EAD screening of essential oils is a viable analytical technique to detect quantitatively minor constituents, which could be potent repellents when tested at an appropriate dose.     

Chemical Constituents and Insecticidal Activities of Ajania fruticulosa Essential Oil

The insecticidal activity and chemical constituents of the essential oil from Ajania fruticulosa were investigated. Twelve constituents representing 91.0% of the essential oil were identified, and the main constituents were 1,8‐cineole ( 41.40% ), (+)‐camphor ( 32.10% ), and myrtenol (8.15%). The essential oil exhibited contact toxicity against Tribolium castaneum and Liposcelis bostrychophila adults with LD₅₀ values of 105.67 μg/adult and 89.85 μg/cm², respectively. The essential oil also showed fumigant toxicity against two species of insect with LC₅₀ values of 11.52 and 0.65 mg/l, respectively. 1,8‐Cineole exhibited excellent fumigant toxicity (LC₅₀ = 5.47 mg/l) against T. castaneum. (+)‐Camphor showed obvious fumigant toxicity (LC₅₀ = 0.43 mg/l) against L. bostrychophila. Myrtenol showed contact toxicity (LD₅₀ = 29.40 μg/cm²) and fumigant toxicity (LC₅₀ = 0.50 mg/l) against L. bostrychophila. 1,8‐Cineole and (+)‐camphor showed strong insecticidal activity to some important insects, and they are main constituents of A. fruticulosa essential oil. The two compounds may be related to insecticidal activity of A. fruticulosa essential oil against T. castaneum and L. bostrychophila.     

Achillea filipendulina Lam.: Chemical Constituents and Antimicrobial Activities of Essential Oil of Stem,Leaf, and Flower

In this study, we extracted the essential oils of the stem, leaf, and flower of Achillea filipendulina, analyzed them, and studied their antibacterial properties. Of 16, 53, and 35 compounds identified in the stem, leaf, and flowers, respectively, only five are present in all three segments of the plant. The essential oil of the stem was mainly composed of neryl acetate, spathulenol, carvacrol, santolina alcohol, and trans‐caryophyllene oxide. However, the main identified components of leaf were 1,8‐cineole, camphor, ascaridole, trans‐isoascaridole, and piperitone oxide and the main components of the flower oil were ascaridole, trans‐isoascaridole, 1,8‐cineole, p‐cymene, and camphor. The extracted oil from different segments demonstrated varying antibacterial properties against both Gram‐positive and Gram‐negative bacteria, demonstrated by disk, minimum inhibitory concentration, and minimum bactericidal concentration methods. These suggest that the application of all segments of aerial parts of A. filipendulina may have a better therapeutic effect in fighting pathogenic systems.     

Comparison of volatile organic compounds from uninfested and Monochamus alternatus Hope infested Pinus massoniana Lamb.

Monochamus alternatus is a destructive stem‐boring herbivore of Pinus massoniana, and the principal vector of pine wood nematode. To investigate the impacts of boring by M. alternatus larvae on the emission of volatile organic compounds (VOCs) from their host trees, the VOCs from uninfested and M. alternatus larvae infested P. massoniana trees were observed using a gas chromatograph–mass spectrometer. We detected 12, 9, 18 and 14 volatile organic compounds from infested xylem, infested phloem, uninfested xylem and uninfested phloem, respectively. In P. massoniana xylem, the boring of M. alternatus larvae induced cyclosativene, and inhibited 4‐carene, humulene, styrene, α‐phellandrene, β‐myrcene, β‐phellandrene and γ‐terpinene. The relative amounts of camphene, copacamphene, longicyclene, longifolene, tricyclene and α‐longipinene were significantly increased, and the relative amounts of α‐pinene and β‐pinene were significantly decreased by the boring behaviors of M. alternatus larvae. In P. massoniana phloem, the boring of M. alternatus larvae induced 2‐bornanone, copacamphene, longicyclene and α‐longipinene, and inhibited 2‐carene, 4‐carene, styrene, α‐phellandrene, β‐myrcene, β‐phellandrene, β‐pinene, γ‐terpinene and ο‐cymene. The relative amounts of camphene, caryophyllene and longifolene were significantly increased by the boring behaviors of M. alternatus larvae. The results indicate that the boring behaviors of M. alternatus larvae changed both the sorts and contents of the VOCs from P. massoniana trees.     

Structure–Activity Relationship Studies on Derivatives of Eudesmanolides from Inula helenium as Toxicants against Aedes aegypti Larvae and Adults

An Aedes aegypti larval toxicity bioassay was performed on compounds representing many classes of natural compounds including polyacetylenes, phytosterols, flavonoids, sesquiterpenoids, and triterpenoids. Among these compounds, two eudesmanolides, alantolactone, and isoalantolactone showed larvicidal activities against Ae. aegypti and, therefore, were chosen for further structure–activity relationship study. In this study, structural modifications were performed on both alantolactone and isoalantolactone in an effort to understand the functional groups necessary for maintaining and/or increasing its activity, and to possibly lead to more effective insect‐control agents. All parent compounds and synthetic modification reaction products were evaluated for their toxic activities against Ae. aegypti larvae and adults. Structure modifications included epoxidations, reductions, catalytic hydrogenations, and Michael additions to the α,β‐unsaturated lactones. None of the synthetic isomers synthesized and screened against Ae. aegypti larvae were more active than isoalantolactone itself which had an LC₅₀ value of 10.0 μg/ml. This was not the case for analogs of alantolactone for which many of the analogs had larvicidal activities ranging from 12.4 to 69.9 μg/ml. In general, activity trends observed from Ae. aegypti larval screening were not consistent with observations from adulticidal screening. The propylamine Michael addition analog of alantolactone was the most active adulticide synthesized with an LC₅₀ value of 1.07 μg/mosquito. In addition, the crystal structures of both alantolactone and isoalantolactone were determined using CuK_α radiation, which allowed their absolute configurations to be determined based on resonant scattering of the light atoms.     

Chemical Composition of the Essential Oil of Nigeria Grown Hoslundia opposita Vahl (Lamiaceae) Dried Leaves and Its Bioactivity against Cowpea Seed Bruchid

Due to several ecological and human hazards of synthetic pesticides in postharvest crop protection, there is the need to search for eco‐friendly alternatives. In this study, chemical composition and insecticidal activities of essential oil (EO) obtained from Hoslundia opposita dried leaves were evaluated against cowpea seed bruchid. Eight constituents, predominated by oxygenated monoterpenes (78.86%), were identified using Gas Chromatography (GC)/MS. The constituents were 1,8‐cineole ( 1 ; 61.15%), followed by α‐terpineol ( 2 ; 16.81%), β‐phellandrene ( 3 ; 13.24%), β‐farnesene (4; 3.55%), α‐pinene ( 5 ; 1.89%), Germacrene D ( 6 ; 1.83%), cis‐sabinene hydrate ( 7 ; 0.90%) and caryophyllene ( 8 ; 0.63%). In fumigation bioassay, at 6 h after exposure (HAE), 0.78 ml EO/l air caused 35.33% mortality which was significantly lower than 60.90% and 63.6% observed at 3.15 and 6.25 ml/l air, respectively. Mortality reached 90.0% at 24 HAE regardless of the applied concentration. Lethal time for 50% of the bruchids (LT₅₀) at concentration of 0.78 ml/l air (6.89 h) was higher than the LT₅₀ at 3.15 and 6.25 ml/l air (4.72 and 4.44 h, respectively). H. opposita EO reduced Callosobruchus maculatus oviposition, while progeny emergence observed in EO‐treated seeds (2.42 – 25.73) was significantly (P < 0.05) lower than 51.56 observed in control. The results confirm H. opposita EO's potentials for control of cowpea bruchids.