Phytochemical inve stigation of the purified fractions of the active dichloromethane extract of Hysterionica pinifolia (Poir.) Baker led to the identification of five compounds. New acetylenic alcohol (E)-undec-3-en-5,7-diyne-1-ol (1) and three other compounds (3) , (4) , and (5) were reported for the first time in this species. Furthermore, forty-six components from the volatile fraction of H. pinifolia were identified. These compounds were elucidated using 1D and 2D NMR spectroscopy as well as MS-ESI and GC-FID-MS experiments. The dichloromethane extract, its fractions , and the methanolic extract were tested for insecticidal activity against Tribolium castaneum under laboratory conditions. The dichloromethane extract and the fraction F2 were found to be activ e, showing high larval mortality. The dichloromethane extract was also active against T . castaneum adults. The results have shown that H. pinifolia could be considered, in a near future, as a potential source for the developmen t of a botanical insecticide for pest control .
Cabrera, A.L. (1963) Flora de la provincia de Buenos Aires. Colección Científica del INTA. INTA Ed, Buenos Aires.
Bohlmann, F., Burkhardt, T. and Zdero, C. (1973) Naturally Occurring Acetylenes. Academic Press, London, New York.
Cufre, I., Tarcaya, V., Broussalis, A. and Miño, J. (2014) Hybanthus parviflorus and H. bigibbosus (Violaceae): Acute and Subchronic Oral Toxicity Assessment of Hydroalcoholic Extracts in Rodents. Revista Latinoamericana de Química, 42, 50-56.
Chen, Y., Luo, J., Zhang, N., Yu, W., Jiang, J. and Dai, G. (2021) Insecticidal Activities of Salvia hispanica L. Essential Oil and Combinations of Their Main Compounds against the Beet Armyworm Spodoptera exigua. Industrial Crops and Products, 162, Article ID: 113271. https://doi.org/10.1016/j.indcrop.2021.113271
Broussalis, A., Clemente, S. and Ferraro, G. (2010) Hybanthus parviflorus (Violaceae): Insecticidal Activity of a South American Plant. Crop Protection, 29, 953-956. https://doi.org/10.1016/j.cropro.2010.06.001
Céspedes, C.L., Salazar, J.R., Ariza-Castolo, A., Yamaguchi, L., ávila, J.G., Aqueveque, P., Kubo, I. and Alarcón, J. (2014) Biopesticides from plants: Calceolaria integrifolia s.l. Environmental Research, 132, 391-406. https://doi.org/10.1016/j.envres.2014.04.003
Tarcaya, V., Di Leo Lira, P., Cufre I., González, S., Clemente, S. and Broussalis, A. (2014) Ovidia andina: actividad insecticida, extracto y compuestos bioactivos. Revista Latinoamericana de Química, 42, 89-96.
IRAM (Argentine Institute for Standardization and Certification) (1996) IRAM Standard 18729.
Bingol, K., Bruschweiler-Li, L., Cao, Y., Somogyi, A., Zhang, F. and Bruschweiler F. (2015) Metabolomics beyond Spectroscopic Databases: A Combined MS/NMR. Strategy for the Rapid Identification of New Metabolites in Complex Mixtures. Analytical Chemistry, 87, 3864–3870. https://doi.org/10.1021/ac504633z
Wang, C., He, L., Li, D., Bruschweiler-Li, L., Marshall, A. and Bruschweiler R. (2017) Accurate Identification of Unknown and Known Metabolic Mixture Components by Combining 3D NMR with FT-ICR MS/MS. Journal of Proteome Research, 16, 3774-3786. https://doi.org/10.1021/acs.jproteome.7b00457
Joulain, D. and König, W. (1998) The Atlas of Spectral Data of Sesquiterpene Hydrocarbons. E. B.-Verlag, Hamburg.
Babushok, V., Linstrom, P. and Zenkevich, I. (2011) Retention Indices for Frequently Reported Compounds of Plant Essential Oils. Journal of Physical and Chemical Reference Data, 40, Article ID: 043101. https://doi.org/10.1063/1.3653552
Adams, R. (2007) Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry. 4th Edition, Allured Publishing, Illinois.
Wiley/NIST (2008) The Wiley/NBS Registry of Mass Spectral Data. 8th Edition, J. Wiley & Sons, Inc., New York.
Clemente, S., Mareggiani, G., Broussalis, A., Martino, V. and Ferraro, G. (2003) Insecticidal Effects of Lamiaceae Species against Stored Products Insects. Boletín de Sanidad Vegetal. Plagas, 29, 421-426.
Casadío, A. and Zerba, E. (1996) Desarrollo poblacional de Triboilum castaneum (Herbst) (coleoptera: Tenebrionidae) en distintas dietas y su influencia sobre la toxicidad y resistencia a Malatión. Boletín de sanidad vegetal. Plagas, 22, 511-520.
Steel, R. and Torrie, J. (1993) Bioestadística. Principios y procedimientos. McGraw-Hill, México.
Finney, D.J. (1971) Probit Analysis. Cambridge University Press, New York.
Demarque, D., Crotti, A., Vessecch, R., Lopes, J. and Lopes, N. (2016) Fragmentation Reactions Using Electrospray Ionization Mass Spectrometry: An Important Tool for the Structural Elucidation and Characterization of Synthetic and Natural Products. Natural Products Research, 33, 432-455. https://doi.org/10.1039/C5NP00073D
Konovalov, D. (2014) Polyacetylene Compounds of Plants of the Asteraceae Family (Review). Pharmaceutical Chemistry Journal, 48, 613-631. https://doi.org/10.1007/s11094-014-1159-7
Albuquerque, M., Souza, E., Lins, M., Nogueira, N., Leda Lemos, T., Silveira, E. and Pessoa, O. (2004) Composition and Antimicrobial Activity of the Essential Oil from Aerial Parts of Baccharis trinervis (Lam.) Pers. ARKIVOC, 6, 59-65. https://doi.org/10.3998/ark.5550190.0005.608
Kumar, V., Shekhar, M. C., Tewari, G., Singh, D., Tewari, A. and Bisht, K. (2014) Chemical Composition and Antifungal Activity of Essential Oils from three Hymalayan Erigeron Species. Food Science and Technology, 56, 278-283. https://doi.org/10.1016/j.lwt.2013.12.007
Sreeramoju, P., Prasad, M. and Lakshmipathi, X. (2016) Complete Study of Life Cycle of Tribolium castaneum and its Weight Variations in the Developing Stages. International Journal of Plant, Animal and Environmental Sciences, 6, 95-100.
Kumar, V., Shekhar, M.C., Tewari, G. and Kumar, P.A. (2015) Biopesticide potential of (7R)-Trans, Trans-Nepetalactone and cis Lachnophyllum Ester in Control of Mustard Aphid, Lipaphis erysimi (kalt.). Journal Teknology, 77, 19-24. https://doi.org/10.11113/jt.v77.5981
Kimura, Y., Mori, Y., Suzuki, A. and Bayashi, A. (1981) Isolation and Identification of Two Nematicidal Substances from Roots of Erigeron philadelphicus L. and Nematicidal Activities of Their Related Compounds. Agricultural and Biological Chemistry, 45, 2915-2917. https://doi.org/10.1271/bbb1961.45.2915
Faini, F., Labbe, C. and Coll, J. (1999) Seasonal Changes in Chemical Composition of Epicuticular Waxes from the Leaves of Baccharis linearis. Biochemical Systematics and Ecology, 27, 673-679. https://doi.org/10.1016/S0305-1978(98)00131-8
Eckenbach, U., Lampman, R., Seigler, D., Ebinger, J. and Novak, R. (1999) Mosquitocidal Activity of Acetylenic Compounds from Cryptotaenia canadensis. Journal of Chemical Ecology, 25, 1885-1893. https://doi.org/10.1023/A:1020938001272
Clemente, S., Mareggiani, G., Broussalis, A. and Ferraro, G. (2007) Actividad insecticida de 1,8-cineol sobre mosca de los frutos, Ceratitis capitata Wied. (Diptera: Tephritidae). Dominguezia, 23, 29-34.
Park, I.-K. (2014) Fumigant Toxicity of Oriental Sweetgum (Liquidambar orientalis) and Valerian (Valeriana wallichii) Essential Oils and Their Components, Including Their Acetylcholinesterase Inhibitory Activity, against Japanese Termites (Reticulitermes speratus). Molecules, 19, 12547-12558. https://doi.org/10.3390/molecules190812547
Silva, D., Arrigoni-Blank, M., Bacci, L., Fitzgerald Blank, A., Nunes Faro, R., Oliveira Pinto, J. and Garcia Pereira, K. (2019) Toxicity and Behavioral Alterations of Essential Oils of Eplingiella fruticosa Genotypes and Their Major Compounds to Acromyrmex balzani. Crop Protection, 116, 181-187. https://doi.org/10.1016/j.cropro.2018.11.002