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

Studies on the floral anatomy and scent chemistry of titan arum(Amorphophallus titanum, Araceae)

Amorphophallus titanum (Becc.) Becc. ex Arcang., the titan arum, is popularly known for having the world's largest unbranched inflorescence. The enormous flower-like inflorescence is also called 'corpse flower' or 'carrion flower' due to the characteristic putrid odor of the bloom. The present study illustrates detailed anatomy and micromorphology of the inflorescence by light and scanning electron microscopy. Collenchyma was found to be the major tissue providing mechanical support in the spathe. The appendix consisted of a dense parenchymatous cortex enclosing a hollow center traversed by loose networks of aerenchyma. Anthocyanin pigments found in the epidermises and cortical tissues imparted a purple color to various parts of the inflorescence. Two types of raphide crystals, Psychotria type and Lemna type, and cluster crystals were observed. The volatile compounds from different parts of the inflorescence were collected by a modified headspace-solid phase microextraction (HS-SPME) technique and the samples were analyzed by gas chromatography-mass spectrometry (GC-MS). The major volatile compounds found by this method included isovaleric acid (21.6%), butyric acid (17.0%), benzyl alcohol (16.2%), and g-butyrolactone (12.1%) in the appendix; g-butyrolactone (27.0%), tetradecane (13.4%), and 4-hydroxy-4-methyl-2-pentanone (10.5%) in the male flowers; tetradecane (19.9%), 4-hydroxy-4-methyl-2-pentanone (13.0%), and 3-hydroxy-2-butanone (10.6%) in the female flowers; and butyl acetate (44.5%) and 3-hydroxy-2-butanone (12.2%) in the spathe. Use of different types of SPME fibers and multiple analytical methods is necessary in order to obtain a complete picture of the volatile composition of titan arum blooms.Amorphophallus titanum (Becc.) Becc. ex Arcang., the titan arum, is popularly known for having the world's largest unbranched inflorescence. The enormous flower-like inflorescence is also called 'corpse flower' or 'carrion flower' due to the characteristic putrid odor of the bloom. The present study illustrates detailed anatomy and micromorphology of the inflorescence by light and scanning electron microscopy. Collenchyma was found to be the major tissue providing mechanical support in the spathe. The appendix consisted of a dense parenchymatous cortex enclosing a hollow center traversed by loose networks of aerenchyma. Anthocyanin pigments found in the epidermises and cortical tissues imparted a purple color to various parts of the inflorescence. Two types of raphide crystals, Psychotria type and Lemna type, and cluster crystals were observed. The volatile compounds from different parts of the inflorescence were collected by a modified headspace-solid phase microextraction (HS-SPME) technique and the samples were analyzed by gas chromatography-mass spectrometry (GC-MS). The major volatile compounds found by this method included isovaleric acid (21.6%), butyric acid (17.0%), benzyl alcohol (16.2%), and g-butyrolactone (12.1%) in the appendix; g-butyrolactone (27.0%), tetradecane (13.4%), and 4-hydroxy-4-methyl-2-pentanone (10.5%) in the male flowers; tetradecane (19.9%), 4-hydroxy-4-methyl-2-pentanone (13.0%), and 3-hydroxy-2-butanone (10.6%) in the female flowers; and butyl acetate (44.5%) and 3-hydroxy-2-butanone (12.2%) in the spathe. Use of different types of SPME fibers and multiple analytical methods is necessary in order to obtain a complete picture of the volatile composition of titan arum blooms

Türkiye pimpinella türlerinin uçucu yağ bileşimleri

Tez (doktora) - Anadolu ÜniversitesiAnadolu Üniversitesi, Sağlık Bilimleri Enstitüsü, Farmakognozi Anabilim DalıKayıt no: 173738Türkiye Pimpinella uçucu yağlarının bileşimlerini ortaya koymayı amaçlayan bu çalışmada, ticari önemi olan P. anisum dışındaki 18 tür doğadan toplandı. Meyve, meyvesiz herba ve kök olmak üzere üç kısma ayrılarak su distilasyonu ile uçucu yağları elde edildi. Uçucu yağların bileşimleri GK/KS, bileşiklerin relatif yüzdeleri ise GK ile belirlendi. Uçucu yağlarda tanımlanamayan bileşiklerin, izolasyonu için kolon kromatografisi, Yüksek Performanslı Flash Kromatografisi ve preparatif Yüksek Basınçlı Sıvı Kromatografisi teknikleri uygulandı. Elde edilen maddelerin yapı tayinlerinde UV, IR, NMR (lD-NMR; 1H, 13C, DEPT ve 2D-NMR; COSY, HMQC, HMBC), LC-ESI-FTMS ve EIMS yöntemlerinden yararlanıldı. İzole edilen yirmi bileşikten dört tanesi yeni [4-(2-propenil)-fenil anjelat, 4-(3-metiloksiranil)-fenil 2-metil butirat, aurean ve traginon] altı tanesi Umbelliferae familyası için yeni [4-(1-propenil)-fenil-2-metil butirat, diktamnol, 4,6-guaiadien, 4-(1-propenil)-fenil izobutirat, alismol ve 12-hidroksi-ß-karyofillen asetat] ve biri de Pimpinella cinsi için yeni [trans-izoosmorizol] maddelerdir

Enantiomeric Distribution of Some Linalool Containing Essential Oils and Their Biological Activities

WOS: 000282706200002The enantiomeric composition of linalool was determined in 42 essential oils using chiral columns. Essential oils were analyzed by multidimentional gas chromatography-mass spectrometry using a non-chiral and chiral FSC columns combination with modified gamma-cyclodextrine (Lipodex E) as the chiral stationary phase without previous isolation of the compound from the mixture. The essential oils of Achillea, Ballota, Calamintha, Micromeria, Hedychium, Tanacetum, Coriandrum, Xanthoxylum, Ocimum, Thymus, Lavandula, Elettaria, Cinnamomum, Salvia, Origanum, Satureja, Nepeta, Stachys were used as source material for enantiomeric separation of linalool. Enantiomeric distribution of linalool showed (-)-linalool was much more common than the (+)-linalool in the essential oils in this study. (-)- and (+)-linalool enantiomers were evaluated for antimicrobial, antifungal and antimalarial activities. Both enantiomers demonstrated approximately 50% growth inhibition of Botrytis cinerea at 48 hrs.USDA ARS NPURU; NIH, NIAID, Division of AIDS [AI 27094]Authors would like to thank S. Alan, I. Aslanyurek, E.S. Biskup, I. Chaudhary, H. Duman, N. Goren, M. Koyuncu, S. Kusmenoglu, S. Nacar, G. Tumen, B. Yildiz and late Prof. T. Baytop for supplying samples. The authors thank Ms. J. Linda Robertson, Mr. M. Dewayne Harries and Ms. Bethany Case for assistance with the bioautography and microdilution broth assays and the USDA ARS NPURU for financial support. We also thank Dr. Shabana I. Khan, Dr. Melissa R. Jacob, Mr. John Trott, Ms. Marsha Wright for their contributions in performing antimalarial and antimicrobial assays, which was supported by the NIH, NIAID, Division of AIDS, grant no. AI 27094

Development of a Kairomone-Based Attractant as a Monitoring Tool for the Cocoa Pod Borer, Conopomorpha cramerella (Snellen) (Lepidoptera: Gracillariidae)

The cocoa pod borer (CPB), Conopomorpha cramerella, is a major economic pest of cocoa, Theobroma cacao, in Southeast Asia. CPB monitoring programs currently use a costly synthetic pheromone lure attractive to males. Field trapping experiments demonstrating an effective plant-based alternative are presented in this study. Five lychee-based products were compared for their attractiveness to CPB males. The organic lychee flavor extract (OLFE), the most attractive product, captured significantly more CPB as a 1 mL vial formulation than unbaited traps, while being competitive with the commercial pheromone lures. Additional experiments show that a 20 mL membrane OLFE lure was most effective, attracting significantly more CPB than the pheromone. When the kairomone and pheromone lures were combined, no additive or synergistic effects were observed. Concentrating the OLFE product (OLFEc) using a rotary evaporator increased the lure attractiveness to field longevity for up to 28 weeks; in contrast, pheromone lures were effective for approximately 4 weeks. The 20 mL concentrated OLFE membrane lures should provide a cheaper and more efficient monitoring tool for CPB than the current commercial pheromone lures

Chemical composition and mosquitocidal activity of n-hexane and methanolic extracts from Euphorbia anacampseros var. tmolea: An endemic species of Turkey against Aedes aegypti

Volatile composition of the n-hexane and methanol extracts from E. anacampseros var. tmolea was analyzed by head space-solid phase microextraction (HS-SPME) coupled with gas chromatography-mass spectrometry (GC-MS). Chemical characterization of the methanolic extract was determined by LC-ESI-MS/MS. Both extracts were bioassayed against 1st instar larvae and adult female Ae. aegypti. The main components identified from the E. anacampseros var. tmolea n-hexane fraction were 1,8-cineole (27.5 %), p-cymene (25 %), ?-terpinene (12.8 %), limonene (9.9 %). Methyl hexanoate (18.8 %), methyl nonanoate (13.3 %), dimethyl succinate (6.5 %), methyl octanoate (6 %) and methyl phenylacetate (5.3 %) were identified from the methanolic fraction. The n-hexane extract showed 100 % mortality at 0.1 µg/ µL against 1st instar larvae of Ae. aegypti and the methanolic extract exhibited 83.3 % mortality at 5 µg/mosquito against adult female Ae. aegypti. The bioassay-guided study demonstrates that n-hexane and methanol extracts of E. anacampseros var. tmolea contain compounds with natural mosquito larvicidal and adulticidal activity.U.S. Department of DefenseThis study was partly funded by the Deployed War-Fighter Protection Research Program via grants from the U.S. Department of Defense through the Armed Forces Pest Management Board. The authors thank Miss Jessica Louton (USDA-ARS, CMAVE, Gainesville, FL) for the mosquito bioassays

The Identification of Suberosin from Prangos pabularia Essential Oil and Its Mosquito Activity Against Aedes aegypti

WOS: 000372803000006A detailed analysis of Prangos pabularia Lindl. (Apiaceae) fruit oil was performed by gas chromatography (GC-FID) and gas chromatography-mass spectrometry (GC-MS). Bicyclogermacrene (21%), (Z)-beta-ocimene (19%), alpha-humulene (8%), alpha-pinene (8%) and spathulenol (6%) were the main constituents of the oil. One compound with 1.8% at RI 3420 remained unidentified or tentatively identified as suberosin from the Wiley GC-MS Library. The assumed compound, suberosin was synthesized in two steps and its structure was confirmed by 1D NMR and GC-MS analyses. As part of our continued research to discover new chemicals for use in mosquito control agents as repellents and larvicides, suberosin and its parent compound coumarin were investigated for the mosquito biting deterrent and larvicidal activity against Aedes aegypti. Both suberosin and coumarin showed biting deterrent activity but the activity was lower than the positive control, DEET (N,N-diethyl-3-methylbenzamide). In larval bioassays, suberosin with LC50 value of 8.1 ppm was significantly more toxic than coumarin (LC50 = 49.6 ppm) at 24-h post treatment. These results indicate that suberosin may be useful for use as mosquito larvicidal agent.USDA-ARS [56-6402-1-612]; Deployed War-Fighter Protection Research Program Grant - U.S. Department of Defense through the Armed Forces Pest Management BoardThis study was supported in part by USDA-ARS grant No. 56-6402-1-612, Deployed War-Fighter Protection Research Program Grant funded by the U.S. Department of Defense through the Armed Forces Pest Management Board. We thank Nucleic Magnetic Resonance facility of the University of Florida and Dr. James J. Becnel, Mosquito and Fly Research Unit, Center for Medical, Agricultural and Veterinary Entomology, USDA-ARS, Gainesville, for supplying Ae. aegypti eggs. The authors wish to thank Dr. Jon F. Parcher, National Center for Natural Products Research, The University of Mississippi, University, MS 38677 USA, for English grammar corrections and suggestions

Chemical Composition of a New Taxon, Seseli gummiferum subsp ilgazense, and its Larvicidal Activity against Aedes aegypti

WOS: 000416971500009Mosquitoes are vectors for many pathogens and parasites that cause human diseases including dengue, yellow fever, West Nile, chikungunya, filariasis and malaria which cause high rates of human morbidity and mortality under extreme conditions. Plants are an excellent source for mosquito control agents because they constitute rich sources of bioactive chemicals. They are also biodegradable and environment-friendly. The present study reports on the larvicidal activity of the essential oil of Seseli gummiferum. subsp. ilgazense (Apiaceae) against Aedes aegypti larvae. Essential oil showed 100 and 70% mortality at 125 and 62.6 ppm, respectively, with no mortality at 31.25 ppm. Aerial parts of S. gummiferum subsp. ilgazense were subjected to hydrodistillation to yield 0.6% oil. The essential oil was analyzed by GC-FID and GC-MS techniques. The main constituents in the oil were sabinene (28.8%), germacrene D (9.5%) and alpha-pinene (7.2%).Deployed War-Fighter Protection Research Program Grant - U.S. Department of Defense through the Armed Forces Pest Management BoardThis study was partly supported by the Deployed War-Fighter Protection Research Program Grant funded by the U.S. Department of Defense through the Armed Forces Pest Management Board. We thank Dr. James J. Becnel, Mosquito and Fly Research Unit, Center for Medical, Agricultural and Veterinary Entomology, USDA-ARS, Gainesville, for supplying Ae. aegypti eggs. Part of this work was presented as a poster presentation during the Inaugural Symposium of the Phytochemical Society of Asia (ISPSA 2015), 30 August - 2 September 2015, Tokushima, Japan

Assessment of selected Saudi and Yemeni plants for mosquitocidal activities against the yellow fever mosquito Aedes aegypti

As part of our continuing investigation for interesting biological activities of native medicinal plants, thirty-nine plants, obtained from diverse areas in Saudi Arabia and Yemen, were screened for insecticidal activity against yellow fever mosquito Aedes aegypti (L.). Out of the 57 organic extracts, Saussurea lappa, Ocimum tenuiflorum, Taraxacum officinale, Nigella sativa, and Hyssopus officinalis exhibited over 80% mortality against adult female Ae. aegypti at 5 µg/mosquito. In the larvicidal bioassay, the petroleum ether extract of Aloe perryi flowers showed 100% mortality at 31.25 ppm against 1st instar Ae. aegypti larvae. The ethanol extract of Saussurea lappa roots was the second most active displaying 100% mortality at 125 and 62.5 ppm. Polar active extracts were processed using LC-MS/MS to identify bioactive compounds. The apolar A. perryi flower extract was analyzed by headspace SPME-GC/MS analysis. Careful examination of the mass spectra and detailed interpretation of the fragmentation pattern allowed the identification of various biologically active secondary metabolites. Some compounds such as caffeic and quinic acid and their glycosides were detected in most of the analyzed fractions. Additionally, luteolin, luteolin glucoside, luteolin glucuronide and diglucuronide were also identified as bioactive compounds in several HPLC fractions. The volatile ketone, 6-methyl-5-hepten-2-one was identified from A. perryi petroleum ether fraction as a major compoundU.S. Department of Defense, DOD Deanship of Scientific Research, King Saud UniversityThe authors extend their appreciation to the Deanship of Scientific Research at King Saud University for funding this work through research group No. RG-1437-021 . This study was in part funded by the Deployed War-Fighter Protection Research Program via grants from the U.S. Department of Defense through the Armed Forces Pest Management Board. We thank Miss Jessica Louton, (USDA-ARS, CMAVE, Gainesville FL) for mosquito bioassays. Appendix

Rhanterium epapposum Oliv. essential oil: Chemical composition and antimicrobial, insect-repellent and anticholinesterase activities

WOS: 000406021100005PubMed ID: 28725142The essential oil (EO) of the aerial parts of Rhanterium epapposum Oliv. (Asteraceae), was obtained by hydrodistillation. The oil was subsequently analyzed by both GC-FID and GC-MS, simultaneously. Forty-five components representing 99.2% of the oil composition were identified. The most abundant compounds were camphene (38.5%), myrcene (17.5%), limonene (10.1%) and alpha-pinene (8.7%). Referring to the ethnobotanical utilization, an insecticidal assay was performed, where the oil repelled the yellow fever mosquito Aedes aegypti L. at a minimum effective dose (MED of 0.035 +/- 0.010 mg/cm(2)) compared to the positive control DEET (MED of 0.015 +/- 0.004 mg/cm(2)). Additionally, the in vitro antimicrobial activity against a panel of pathogens was determined using a microdilution method. The acetyl- and butyrylcholine esterase inhibitory activities were measured using the colorimetric Ellman method. The bioassay results showed that the oil was rather moderate in antimicrobial and cholinesterase inhibitions when compared to the standard compoundsDeployed War-Fighter Protection Research Program - U.S. Department of Defense through Armed Forces Pest Management BoardWe thank Greg Allen (USDA-ARS, Center for Medical, Agricultural, and Veterinary Entomology, Gainesville, FL) for performing the mosquito bioassays. This study was supported partially by the Deployed War-Fighter Protection Research Program Grant funded by the U.S. Department of Defense through the Armed Forces Pest Management Board