Laboratory evaluation of natural and synthetic aromatic compounds as potential attractants for male mediterranean fruit fly, ceratitis capitata

Ceratitis capitata, the Mediterranean fruit fly, is one of the most serious agricultural pests worldwide responsible for significant reduction in fruit and vegetable yields. Eradication is expensive and often not feasible. Current control methods include the application of conventional insecticides, leading to pesticide resistance and unwanted environmental effects. The aim of this study was to identify potential new attractants for incorporation into more environmentally sound management programs for C. capitata. In initial binary choice bioassays against control, a series of naturally occurring plant and fungal aromatic compounds and their related analogs were screened, identifying phenyllactic acid (7), estragole (24), o-eugenol (21), and 2-allylphenol (23) as promising attractants for male C. capitata. Subsequent binary choice tests evaluated five semisynthetic derivatives prepared from 2-allylphenol, but none of these were as attractive as 2-allylphenol. In binary choice bioassays with the four most attractive compounds, males were more attracted to o-eugenol (21) than to estragole (24), 2-allylphenol (23), or phenyllactic acid (7). In addition, electroantennography (EAG) was used to quantify antennal olfactory responses to the individual compounds (1–29), and the strongest EAG responses were elicited by 1-allyl-4-(trifluoromethyl)benzene (11), estragole (24), 4-allyltoluene (14), trans-anethole (9), o-eugenol (21), and 2-allylphenol (23). The compounds evaluated in the current investigation provide insight into chemical structure–function relationships and help direct future efforts in the development of improved attractants for the detection and control of invasive C. capitata

Secondary metabolites with ecologic and medicinal implications in Anthemis cretica subsp. petraea from Majella National Park

Anthemis cretica subsp. petraea (Ten.) Greuter is a plant belonging to the Asteraceae family and endemic of central Italy. In this paper, the first analysisof the ethanolic fraction of samples collected in the Majella National Park is reported. Seven compounds were isolated and identified namely parthenolide (1), 9α-acetoxyparthenolide (2), tamarixetin (3), 7-hydroxycoumarin (4), 4'-hydroxyacetophenone (5), leucanthemitol (conduritol F) (6),and proto-quercitol (7). Isolation of the compounds was achieved by means ofcolumn chromatography (CC), while their identification was achieved through spectroscopic and spectrometric techniques. The presence of these compounds is of great relevance. Compounds 1 and 2 are chemosystematic markers of the family, thus confirming the correct botanical classification of the species. Conversely, compounds 3, 5,and 7 were identified for the first time in the species and, instead, confirm the tendency of endemic entities to develop characteristic metabolite patterns in respect to cosmopolite species. Moreover, the presence of compounds 6 and 7 has ecologic implications and may be linked to this taxon’s adaption to dry environments. The production of these osmolytes may, in fact, represent the reason why this species is able to survive in extreme conditions of aridity. Lastly, from a medicinal standpoint, the isolated compounds are endowed with interesting biological activities and may justify, on a molecular base, the widespread traditional uses of the Anthemis species, as well as a basis for the use ofthe subspecies petraea

Promising assets of South Africa? Cyclopia genistoides and Hoodia gordonii

Previous pharmacological studies have shown that H. gordonii could have different mechanism of action than the already withdrawn sympathomimetic weight-loss medicines, thus a possibly better risk/benefit ratio than the former antiobesity drugs. Yet, sympathomimetic effect with substantial β-receptor-mediated contribution similar to the mechanism of action of several already withdrawn weight loss medications was recorded in our investigation. Hence, the use of Hoodia gordonii as a possible anti-obesity drug is questionable. The phytoestrogenic activity of C. genistoides extracts was linked to compounds, isolated via bioactivity-guided fractionation, using the transgenic plant system pER8:GUS. The extracts of the plant materials were subjected to multiple step chromatographic separation (including CC, VLC, MPLC, HPLC, PLC, RPC) resulting in the isolation of 17 compounds from which 14 were first isolated from this species and 10 from the genus. Antiproliferative MTT assays were also performed on A2780 and T47D human cancer cell lines. The results suggested, that oestrogen induced cell-proliferation or oestrogen independent antiproliferative effect might have played a role. The recorded xanthine oxidase inhibitory activity of two compounds isolated from the dichloromethane layers, added to the long list of bioactivities of Cyclopia species. The effect of fermentation on the phytochemical content was also investigated with the means of HPLC. The results supported the tradition, as the fermented honeybush tea was rich in compounds with stronger phytoestrogenic activity, while the non-fermented tea contained larger amounts from the less active glycoside. However, bacterial fermentation levelled the difference in the concentration of naringenin between the aqueous extracts from fermented and non-fermented plant materials. Although, the quantitative comparison of fermented and non-fermented honeybush implies, that the fermented tea has higher amount of these phytoestrogens except the least active compound, the measured low amounts question the biological activity of the traditionally used infusion. However, it does not exclude the possibility that synergism or antagonism of multiple polyphenols targeting different ER isoforms can result in phytoestrogenic effect of different extracts, even if the individual compounds are small in quantity

Insect herbivory (Choristoneura fumiferana, Tortricidea) underlies tree population structure (Picea glauca, Pinaceae)

Variation in insect herbivory can lead to population structure in plant hosts as indicated by defence traits. In annual herbaceous, defence traits may vary between geographic areas but evidence of such patterns is lacking for long-lived species. This may result from the variety of selection pressures from herbivores, long distance gene flow, genome properties, and lack of research. We investigated the antagonistic interaction between white spruce (Picea glauca) and spruce budworm (SBW, Choristoneura fumiferana) the most devastating forest insect of eastern North America in common garden experiments. White spruces that are able to resist SBW attack were reported to accumulate the acetophenones piceol and pungenol constitutively in their foliage. We show that levels of these acetophenones and transcripts of the gene responsible for their release is highly heritable and that their accumulation is synchronized with the most devastating stage of SBW. Piceol and pungenol concentrations negatively correlate with rate of development in female SBW and follow a non-random geographic variation pattern that is partially explained by historical damage from SBW and temperature. Our results show that accumulation of acetophenones is an efficient resistance mechanism against SBW in white spruce and that insects can affect population structure of a long-lived plant

first isolation of acetovanillone and piceol from crinum buphanoides and crinum graminicola i verd amaryllidaceae

Screening of three native South African Amaryllidaceae bulbs, aimed at finding new metabolites for their promising biological activities, lead to the initial discovery of two interesting non-alkaloid compounds viz., acetovanillone 1 (also known as apocynin) and 4-hydroxyacetophenone 2 (also named piceol) isolated from Crinum buphonoides, while only the former was isolated from Crinum graminicola. This is the first time that acetovanillone 1 and piceol 2 were isolated from C. graminicola and C. buphanoides, respectively. Acetovanillone 1 was recently reported as a metabolite of Boophane disticha (L.f.), another South Africa Amaryllidacea species

White spruce resistance against the spruce budworm : genetic control and insect-host interaction

Picea glauca (Moench) Voss (l’épinette blanche) est l’un des principaux hôtes de la tordeuse des bourgeons de l’épinette (TBE), le défoliateur épidémique le plus dommageable de l’est du Canada qui est à l’origine de la mortalité d’arbres et de pertes économiques d’envergure considérables. Un mécanisme constitutif de résistance contre la TBE a récemment été découvert. Dans la présente thèse, nous avons étudié ce mécanisme basé sur l’accumulation foliaire du picéol et du pungénol, deux acétophénones découlant de la surexpression du gène Pgglu-1. Ces trois facteurs sont désignés comme étant des «biomarqueurs de résistance». Nous avons aussi étudié la picéine, un acétophénone glycosilé qui est le précurseur du picéol, et l’ensemble des quatre facteurssont désignés «biomarqueurs de défense». La première partie de la thèse présente une approche de génétique quantitative s’appuyant sur l’analyse de 874 arbres représentant 33 familles et 71 lignées clonales répartis dans sept emplacements de l’est du Canada. Nos objectifs étaient : i) de déterminer le contrôle génétique des biomarqueurs de défense, ii) d’estimer les corrélations génétiques et phénotypiques entre les quatre traits de défense, iii) d’évaluer la présence de compromis entre les biomarqueurs de défense et la croissance primaire. Nous avons conclu que l’héritabilité au sens strict du picéol, du pungénol et de l’expression du gène Pgglu-1 était modérée (0,55, 0,50 et 0,58 respectivement), et obtenu des estimés un peu plus élevées pour l’héritabilité au sens large du picéol et du pungénol (0,66 et 0,60 respectivement), ce qui indique que ces traits de résistance sont soumis à un contrôle génétique additif. Les traits de résistance et la croissance montrent des corrélations génétiques positives (de 0,14 à 0,30), ce qui suggère que le mécanisme de résistance n’entraine pas un effet négatif sur la croissance de l’épinette blanche. Dans la deuxième partie de la thèse, nous avons étudié l’interaction insecte-hôte en menant des essais d’élevage d’insectes sur différents clones d’épinettes blanches. Nos objectifs étaient iv) de caractériser la variation développementale des acétophénones de défense, v) d’évaluer l’influence du stade phénologique de l’hôte sur le niveau de résistance indiqué par la performance biologique de la TBE et vi) de déterminer si les traits de résistance sont inductibles. Nous concluons que la variation des acétophénones dépend du phénotype de résistance de l’arbre, et que l’efficacité des traits de résistance dépend du synchronisme entre le Piceaglauca et l’alimentation des insectes. Finalement, nous avons démontré que ce mécanisme de résistance peut être inductible.Picea glauca (Moench) Voss (white spruce) is one of the main hosts of the spruce budworm (SBW), anepidemic defoliator that is the most damaging in forests of eastern North America causing tree mortality and large economic losses. A constitutive resistance mechanism against the SBW was recently discovered. In this thesis, we studied this mechanism based on the foliar accumulation of aglycon acetophenones ̶piceol and pungenol ̶resulting from the expression of the Pgglu-1gene; and we refer to them as resistance biomarkers. Picein, the glycoside precursor of piceol was also investigated and we refer to all four traits togetheras defense biomarkers. The first part of this thesis presents a quantitative genetic study, which analysed 874 trees representing 33 full-sib families and 71 clonal lines from seven field locations in Eastern Canada. The goals were to i) determine the genetic control of the defense biomarkers, ii) estimate the genetic and phenotypic correlations among the four defensive traits and growth, and iii) evaluate the occurrence of trade-offs between the defense biomarkers and primary growth. Narrowsense heritability of piceol, pungenol and Pgglu-1 gene expression was moderate (0.55, 0.50 and 0.58, respectively). Slightly higher broad sense heritability estimates were obtained for acetophenones (0.66 and 0.60 respectively), indicating that additive genetic effects playa major role in these resistance biomarkers. Positive genetic correlations were found between the resistance traits and growth (from 0.14 to 0.30), suggesting that the resistance mechanism does not compromise growth in white spruce. In the second partof the thesis, we studied the insect-host interaction by use of insect rearing trials in severalwhite spruce clones. Our objectives were to iv) characterize the developmental and phenological variation of the defense acetophenones, v) evaluate the impact of the matched and delayed host phenology windows on the biological performance of the SBW, and vi) assess the inducibility potential of the resistance traits. Weshow that there are considerable variations in the acetophenone accumulation profiles between individual trees supporting their classification as Resistant (R) and Non-Resistant (NR); that the efficiency of the resistance traits is influenced by the synchronization between the P. glauca phenology and the insect feeding. Finally, we show that the resistance mechanism can be inducible

Supplemental Information 6: Raw data - Figure 4

Eastern spruce budworm (Choristoneura fumiferiana Clemens) (ESBW) is a major forest pest which feeds on young shoots of white spruce (Picea glauca) and can cause landscape level economic and ecological losses. Release of acetophenone metabolites, piceol and pungenol, from their corresponding glycosides, picein and pungenin, can confer natural resistance of spruce to ESBW. A beta-glucosidase gene, Pgβglu-1, was recently discovered and the encoded enzyme was characterized in vitro to function in the release of the defensive acetophenone aglycons. Here we describe overexpression of Pgβglu-1 in a white spruce genotype whose metabolome contains the glucosylated acetophenones, but no detectable amounts of the aglycons. Transgenic overexpression of Pgβglu-1 resulted in release of the acetophenone aglycons in planta. This work provides in vivo evidence for the function of Pgβglu-1

The Health-Promoting Potential of Salix spp. Bark Polar Extracts: Key Insights on Phenolic Composition and In Vitro Bioactivity and Biocompatibility

Salix spp. have been exploited for energy generation, along with folk medicine use of bark extracts for antipyretic and analgesic benefits. Bark phenolic components, rather than salicin, have demonstrated interesting bioactivities, which may ensure the sustainable bioprospection of Salix bark. Therefore, this study highlights the detailed phenolic characterization, as well as the in vitro antioxidant, anti-hypertensive, Staphylococcus aureus growth inhibitory effects, and biocompatibility of Salix atrocinerea Brot., Salix fragilis L., and Salix viminalis L. bark polar extracts. Fifteen phenolic compounds were characterized by ultra-high-performance liquid chromatography-ultraviolet detection-mass spectrometry analysis, from which two flavan-3-ols, an acetophenone, five flavanones, and a flavonol were detected, for the first time, as their bark components. Salix bark extracts demonstrated strong free radical scavenging activity (5.58–23.62 µg mL−1 IC50 range), effective inhibition on angiotensin-I converting enzyme (58–84%), and S. aureus bactericidal action at 1250–2500 µg mL−1 (6–8 log CFU mL−1 reduction range). All tested Salix bark extracts did not show cytotoxic potential against Caco-2 cells, as well as S. atrocinerea Brot. and S. fragilis L. extracts at 625 and 1250 µg mL−1 against HaCaT and L929 cells. These valuable findings can pave innovative and safer food, nutraceutical, and/or cosmetic applications of Salix bark phenolic-containing fractions.info:eu-repo/semantics/publishedVersio

GC MS Based Comparative Phytochemical Profiling of Rhodiola Imbricata Roots Collected from Different High Mountain Passes of Ladakh India and a First Report of Apocynin from Genus Rhodiola

Rhodiola imbricata is a high value medicinal plant of trans-Himalayan mountain passes in Ladakh. This plant is a highly sought after in national and international herbal product market due to its unique phytochemical composition and resultant medicinal properties. However, compositional variation in the raw material from different geographical locations results in variation in quality as well as efficacy of the final products. The current study was designed to generate the comparative GC-MS profiles of hydro-methanolic extracts of Rhodiola imbricata root samples collected from various locations in Ladakh i.e., Chang La (17605 ft), Khardung La (18,379 ft), and Shashi La (13908 ft) mountain passes. The study highlighted variations in volatile phytochemical composition in root samples collected from different locations, especially with respect to phenols, terpenes and fatty acids. Samples from Chang La had maximum amount of phenolic compounds (96.78 per cent), followed by samples from Khardung La (77.05 per cent) while they were undetected in samples from Shashi La pass. Specifically, comparative GC-MS profiling revealed that peak area percentage of two important bioactive compounds (i.e. piceol and apocynin) varied amongst samples. In the samples collected from Chang La, the piceol covered (94 per cent) and apocynin covered (2.78 per cent) peak area whereas in samples collected from Khardung La, piceol covered (73.8 per cent) and apocynin covered (3.25 per cent) peak areas respectively, however, samples collected from Shashi La showed none of these compounds. Interestingly, in the present study, apocynin (a potent NADPH oxidase inhibitor) is being reported for the first time from Rhodoila genus. On the basis of present findings, samples collected from Chang La and Khardung La passes showed better phytochemical composition of pharmacological active phenolic compounds than Shashi La sample

Las coordenadas espacio-temporales en la «Caccia di Diana» de Giovanni Boccaccio.

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