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Tsikolia M.,U.S. Department of Agriculture | Bernier U.R.,U.S. Department of Agriculture | Coy M.R.,U.S. Department of Agriculture | Chalaire K.C.,U.S. Navy | And 8 more authors.
Pesticide Biochemistry and Physiology | Year: 2013

Twenty trifluoromethylphenyl amides were synthesized and evaluated as fungicides and as mosquito toxicants and repellents. Against Aedes aegypti larvae, N-(2,6-dichloro-4-(trifluoromethyl)phenyl)-3,5-dinitrobenzamide (1e) was the most toxic compound (24h LC50 1940nM), while against adults N-(2,6-dichloro-4-(trifluoromethyl)phenyl)-2,2,2-trifluoroacetamide (1c) was most active (24h LD50 19.182nM, 0.5μL/insect). However, the 24h LC50 and LD50 values of fipronil against Ae. aegypti larvae and adults were significantly lower: 13.55nM and 0.787×10-4nM, respectively. Compound 1c was also active against Drosophila melanogaster adults with 24h LC50 values of 5.6 and 4.9μg/cm2 for the Oregon-R and 1675 strains, respectively. Fipronil had LC50 values of 0.004 and 0.017μg/cm2 against the two strains of D. melanogaster, respectively. In repellency bioassays against female Ae. aegypti, 2,2,2-trifluoro-N-(2-(trifluoromethyl)phenyl)acetamide (4c) had the highest repellent potency with a minimum effective dosage (MED) of 0.039μmol/cm2 compared to DEET (MED of 0.091μmol/cm2). Compound N-(2-(trifluoromethyl)phenyl)hexanamide (4a) had an MED of 0.091μmol/cm2 which was comparable to DEET. Compound 4c was the most potent fungicide against Phomopsis obscurans. Several trends were discerned between the structural configuration of these molecules and the effect of structural changes on toxicity and repellency. Para- or meta- trifluoromethylphenyl amides with an aromatic ring attached to the carbonyl carbon showed higher toxicity against Ae. aegypti larvae, than ortho- trifluoromethylphenyl amides. Ortho- trifluoromethylphenyl amides with trifluoromethyl or alkyl group attached to the carbonyl carbon produced higher repellent activity against female Ae. aegypti and Anopheles albimanus than meta- or para- trifluoromethylphenyl amides. The presence of 2,6-dichloro- substitution on the phenyl ring of the amide had an influence on larvicidal and repellent activity of para- trifluoromethylphenyl amides. © 2013 The Authors. Source


Ali A.,National United University | Tabanca N.,National United University | Demirci B.,Anadolu University | Blythe E.K.,Mississippi State University | And 5 more authors.
Records of Natural Products | Year: 2016

Essential oils of four ornamental species and hybrids of Nepeta: N. racemosa Lam. hybrid ‘Select’, N. sibirica L., N. subsessilis Maxim, and N.×faassenii Bergmans ex Stearn ‘Dropmore were studied for their chemical composition, larvicidal and biting deterrent activity. Water-distilled essential oils from aerial parts of Nepeta species were analyzed by gas chromatography (GC-FID) and gas chromatography mass spectrometry (GC-MS). Nepeta racemosa hybrid ‘Select’ and N. ×faassenii ‘Dropmore’ essential oils were rich in 1,8-cineole whereas N. sibirica and N. subsessilis essential oils mainly consisted of sesquiterpenes: (Z)- β-farnesene, β-bisabolene, δ -cadinene or β -caryophyllene, and caryophyllene oxide. Many Nepeta species essential oils are reported to be rich in nepetalactone isomers, but essential oils from these species contained either very low or no nepetalactone content. In biting deterrent bioassays, essential oils of these Nepeta species and hybrids at 100 µg/cm2 showed activity similar to DEET at 25 nmol/cm2 against Aedes aegypti, whereas this activity at the concentration of 10 µg/cm2 was lower than DEET. All the essential oils showed weak larvicidal activity and mortalities were observed only at highest dose of 125 ppm against Ae. aegypti. © 2015 ACG Publications. All rights reserved. Source


Avula B.,The University of Mississippi | Wang Y.-H.,The University of Mississippi | Rumalla C.S.,The University of Mississippi | Ali Z.,The University of Mississippi | And 4 more authors.
Journal of Pharmaceutical and Biomedical Analysis | Year: 2011

Analytical methods including HPLC, UPLC and HPTLC are presented for the determination of major alkaloid and triterpene saponins from the roots of Caulophyllum thalictroides (L.) Michx. (blue cohosh) and dietary supplements claiming to contain blue cohosh. A separation by LC was achieved using a reversed phase column, PDA with ELS detection, and ammonium acetate/acetonitrile gradient as the mobile phase. Owing to their low UV absorption, the triterpene saponins were detected by evaporative light scattering. The eight triterpene saponins (cauloside H, leonticin D, cauloside G, cauloside D, cauloside B, cauloside C, cauloside A and saponin PE) and the alkaloid magnoflorine could be separated within 35. min using HPLC method and within 8.0. min using UPLC method with detection limits of 10μg/mL for saponins and 1μg/mL for magnoflorine. The detection wavelength was 320. nm for magnoflorine and ELS detection was used for the eight saponins. The methods were also successfully applied to analyze different dietary supplements. For the products claiming to contain blue cohosh, there was a significant variability in the amounts of triterpene saponins detected. Calculations based on the analysis results for dietary supplements showed that maximum daily intake of alkaloid and saponins vary with the form (solids/liquids) and recommended doses according to the products label. Intakes varied from 0.57 to 15.8. mg/day for magnoflorine and from 5.97 to 302.4. mg/day for total saponins. LC-mass spectrometry coupled with electrospray ionization (ESI) method is described for the identification and confirmation of nine compounds in plant samples and dietary products. A HPTLC method was also developed for the fast chemical fingerprint analysis of C. thalictroides samples. © 2011 Elsevier B.V. Source


Avula B.,The University of Mississippi | Sagi S.,The University of Mississippi | Gafner S.,American Botanical Council | Upton R.,American Herbal Pharmacopoeia | And 3 more authors.
Analytical and bioanalytical chemistry | Year: 2015

Ginkgo biloba is one of the most widely sold herbal supplements and medicines in the world. Its popularity stems from having a positive effect on memory and the circulatory system in clinical studies. As ginkgo popularity increased, non-proprietary extracts were introduced claiming to have a similar phytochemical profile as the clinically tested extracts. The standardized commercial extracts of G. biloba leaf used in ginkgo supplements contain not less than 6% sesquiterpene lactones and 24% flavonol glycosides. While sesquiterpene lactones are unique constituents of ginkgo leaf, the flavonol glycosides are found in many other botanical extracts. Being a high value botanical, low quality ginkgo extracts may be subjected to adulteration with flavonoids to meet the requirement of 24% flavonol glycosides. Chemical analysis by ultra high performance liquid chromatography-mass spectrometry revealed that adulteration of ginkgo leaf extracts in many of these products is common, the naturally flavonol glycoside-rich extract being spiked with pure flavonoids or extracts made from another flavonoid-rich material, such as the fruit/flower of Japanese sophora (Styphnolobium japonicum), which also contains the isoflavone genistein. Recently, genistein has been proposed as an analytical marker for the detection of adulteration of ginkgo extracts with S. japonicum. This study confirms that botanically authenticated G. biloba leaf and extracts made therefrom do not contain genistein, and the presence of which even in trace amounts is suggestive of adulteration. In addition to the mass spectrometric approach, a high performance thin layer chromatography method was developed as a fast and economic method for chemical fingerprint analysis of ginkgo samples. Source


Avula B.,The University of Mississippi | Sagi S.,The University of Mississippi | Gafner S.,American Botanical Council | Upton R.,American Herbal Pharmacopoeia | And 4 more authors.
Analytical and Bioanalytical Chemistry | Year: 2015

Ginkgo biloba is one of the most widely sold herbal supplements and medicines in the world. Its popularity stems from having a positive effect on memory and the circulatory system in clinical studies. As ginkgo popularity increased, non-proprietary extracts were introduced claiming to have a similar phytochemical profile as the clinically tested extracts. The standardized commercial extracts of G. biloba leaf used in ginkgo supplements contain not less than 6 % sesquiterpene lactones and 24 % flavonol glycosides. While sesquiterpene lactones are unique constituents of ginkgo leaf, the flavonol glycosides are found in many other botanical extracts. Being a high value botanical, low quality ginkgo extracts may be subjected to adulteration with flavonoids to meet the requirement of 24 % flavonol glycosides. Chemical analysis by ultra high performance liquid chromatography-mass spectrometry revealed that adulteration of ginkgo leaf extracts in many of these products is common, the naturally flavonol glycoside-rich extract being spiked with pure flavonoids or extracts made from another flavonoid-rich material, such as the fruit/flower of Japanese sophora (Styphnolobium japonicum), which also contains the isoflavone genistein. Recently, genistein has been proposed as an analytical marker for the detection of adulteration of ginkgo extracts with S. japonicum. This study confirms that botanically authenticated G. biloba leaf and extracts made therefrom do not contain genistein, and the presence of which even in trace amounts is suggestive of adulteration. In addition to the mass spectrometric approach, a high performance thin layer chromatography method was developed as a fast and economic method for chemical fingerprint analysis of ginkgo samples. © 2015 Springer-Verlag Berlin Heidelberg Source

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