Phytochemical investigation
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) werereported 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
active, 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 development of a botanical insecticide for pest control.
References
[1]
Cabrera, A.L. (1963) Flora de la provincia de Buenos Aires. Colección Científica del INTA. INTA Ed, Buenos Aires.
[2]
Bohlmann, F., Burkhardt, T. and Zdero, C. (1973) Naturally Occurring Acetylenes. Academic Press, London, New York.
[3]
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.
[4]
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
[5]
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
[6]
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
[7]
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.
[8]
IRAM (Argentine Institute for Standardization and Certification) (1996) IRAM Standard 18729.
[9]
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
[10]
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
[11]
Joulain, D. and König, W. (1998) The Atlas of Spectral Data of Sesquiterpene Hydrocarbons. E. B.-Verlag, Hamburg.
[12]
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
[13]
Adams, R. (2007) Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry. 4th Edition, Allured Publishing, Illinois.
[14]
Wiley/NIST (2008) The Wiley/NBS Registry of Mass Spectral Data. 8th Edition, J. Wiley & Sons, Inc., New York.
[15]
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.
[16]
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.
[17]
Steel, R. and Torrie, J. (1993) Bioestadística. Principios y procedimientos. McGraw-Hill, México.
[18]
Finney, D.J. (1971) Probit Analysis. Cambridge University Press, New York.
[19]
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
[20]
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
[21]
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
[22]
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
[23]
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.
[24]
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
[25]
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
[26]
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
[27]
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
[28]
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.
[29]
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
[30]
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