Chemical composition and cytotoxic activity of the essential oil of Hinterubera imbricata species collected in Venezuelan Andes

References

• Takhtajan, A. (1997). Diversity and classification of flowering plants. Columbia University Press.
   Google Scholar
• Judd, W.S., Campbell, C.S., Kellog, E.A. and Sterens, S.P.F. (1999). Plant systematics: A phylogenetic approach. Sinauer Associates, Inc.
   Google Scholar
• The Angiosperm Phylogeny Group. (2003). An update of the Angiosperm Phylogeny Group classification for the orders and families of flowering plants: APG II. Bot. J. Linn. Soc.141: 399-436. doi: 10.1046/j.1095-8339.2003.t01-1-00158.x
   Web of Science ®Google Scholar
• Anderberg, A.A., Baldwin, B.G., Bayer, R.G., Breitwieser, J., Jeffrey, C., Dillon, M.O., Elden€as, P., Funk, V.A., Garcia-Jacas, N., Hind, D.J.N., Karis, P.O., Lack, H.W., Nesom, G., Nordenstam, B., Oberprieler, C., Panero, J.L., Puttock, C., Robinson, H., Stuessy, T.F., Susanna, A., Urtubey, E., Vogt, R., Ward, J. and Watson, L.E. (2007). Compositae, in: Kadereit, J.W., Jeffrey, C. (Eds.), The families and genera of vascular plants. Flowering plants. Eudicots. Asterales (pp. 61–588) Springer.
   Google Scholar
• Carrillo, M., Lapp, M. and Torrecilla, P. (2016). Nueva especie de Hinterhubera Sch. Bip. ex Wedd. (Astereae-Asteraceae). Ernstia. 26(2): 43-52.
   Google Scholar
• Badillo, V., Díaz-Piedrahita, S. and Benítez, C.E. (2008). Asteraceae, in: Hokche, O., Berry, P., Huber, O. (Eds.), Nuevo catálogo de la flora vascular de Venezuela (p. 859). Fundación Instituto Botánico de Venezuela “Dr. Tobías Lasser”.
   Google Scholar
• Morillo, G. and Briceño, B. (2000). Distribución de las Asteraceae de los páramos venezolanos. Acta Bot. Venez. 23(1): 47-68.
   Google Scholar
• Stearn, W. (2005). Botanical Latin, six ed. British Library.
   Google Scholar
• Vivas, Y. and Ubiergo, P. (2010). Asteraceae del Valle Morrénico de Mucubají, estado Mérida, Venezuela. Revista de la Facultad de Agronomía de la Universidad del Zulia. 27(1): 39-60.
   Web of Science ®Google Scholar
• Carrillo, M., Lapp, M. and Torrecilla, P. (2018). Taxonomía de Hinterhubera Sch. Bip. ex Wedd. (Asteroideae-Asteraceae) en Venezuela. Ernstia. 28(1): 1-44.
   Google Scholar
• Mangal, M., Sagar, P., Singh, H., Raghava, G.P. and Agarwal, S.M. (2013). NPACT: Naturally occurring plant-based anti-cancer compound-activity-target database. Nucleic Acids Res. 41(Database Issue): D1124-D1129. doi: 10.1093/nar/gks1047
   PubMed Web of Science ®Google Scholar
• Ranwa, A., Elrayess, H.N., Gad and El-Hak, M. (2019). Anticancer natural products: A Review. Cancer. Stud. Mol. Med. Open J. 5(1): 14-25.
   Google Scholar
• Balunas, M.J. and Kinghorn, A.D. (2005). Drug discovery from medicinal plants. Life Sci. 78(5): 431-441. doi: 10.1016/j.lfs.2005.09.012
   PubMed Web of Science ®Google Scholar
• Davies, N. (1990). Gas chromatographic retention indices of monoterpenes and sesquiterpenes on methyl silicone and carbowax 20 M phases. J. Chromatogr. A. 503: 1-24. doi: 10.1016/S0021-9673(01)81487-4
   Web of Science ®Google Scholar
• Adams, R.P. (2007). Identification of essential oil components by gas chromatography/mass spectroscopy. Allured Pub Corp.
   Google Scholar
• Rojas, J., Buitrago, A., Arvelo, F.A., Sojo, F.J., Suarez, A.I., Rojas, L. (2020). Essential oil composition and cytotoxic activity in two species of the plant genus Vismia (Hypericaceae) from the Venezuelan Andes. Rev. Biol. Trop. 68(3): 884-891.
   Web of Science ®Google Scholar
• Rojas, J., Buitrago, J., Rojas, L., Cárdenas, J., Carmona, J. (2013). Chemical composition of the essential oil of Croton huberi Steyerm. (Euphorbiaceae) collected from Tachira-Venezuela. J. Essent. Oil-Bear. Plants. 16(5): 646-650. doi: 10.1080/0972060X.2013.854502
   Web of Science ®Google Scholar
• Buitrago, A., Rojas, J., Velasco, J., Morillo, M., Joly, N., Rojas, L., Martin, P. (2023). Chemical composition and antibacterial activity of essential oils from fruits of Vismia baccifera and Vismia macrophylla collected at different locations in Venezuelan Andes. European J. Med. Plants. 34(12): 45-56. doi: 10.9734/ejmp/2023/v34i121182
   Google Scholar
• Mosmann, T. (1983). Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Methods. 65: 55-63. doi: 10.1016/0022-1759(83)90303-4
   PubMed Web of Science ®Google Scholar
• van Meerloo, J., Kaspers, G.J. and Cloos, J. (2011). Cell sensitivity assays: the MTT assay. Methods Mol. Biol. 731: 237-245. doi: 10.1007/978-1-61779-080-5_20
   PubMedGoogle Scholar
• Merchán-Arenas., D.R., Sojo, F., Arvelo, F. and Kouznetsov, V.V. (2020). Synthesis of dihydroisoindolo[2,1-a]quinolin-11-ones, their in silico ADMET properties and in vitro antitumor activities. RSC Adv. 10(69): 42287-42296. doi: 10.1039/D0RA04555A
   PubMed Web of Science ®Google Scholar
• Suárez, A.I., Mancebo, M., Delle-Monache, F., Tirric, M.M., Sojo, F., Arvelo, F. and Tillett, S. (2016). A new indole-alkaloid and a new phenolic-glycoside with cytotoxic activity from Strychnos fendleri. Nat. Prod. Res. 30(4): 399-405. doi: 10.1080/14786419.2015.1019351
   PubMed Web of Science ®Google Scholar
• Nugroho, A.E., Hermawan, A., Putri, D.D., Novika, A., Meiyanto, E. and Kawaichi, M. (2013). Combinational effects of hexane insoluble fraction of Ficus septica Burm. F. and doxorubicin chemotherapy on T47D breast cancer cells. Asian Pac. J. Trop. Biomed. 3(4): 297-302. doi: 10.1016/S2221-1691(13)60066-0
   PubMedGoogle Scholar
• Radice, M., Durofil, A., Buzzi, R., Baldini, E., Martínez, A.P., Scalvenzi, L. and Manfredini, S. (2022). Alpha-phellandrene and alpha-phellandrene-Rich essential oils: A systematic review of biological activities, pharmaceutical and food applications. Life. 12(10): 1602. doi: 10.3390/life12101602
   PubMedGoogle Scholar
• Wojtunik-Kulesza, K.A., Kasprzak, K., Oniszczuk, T. and Oniszczuk, A. (2019). Natural monoterpenes: Much more than only a scent. Chem. Biodivers. 16(12). doi: 10.1002/cbdv.201900434
   Web of Science ®Google Scholar
• Tan, X.C., Chua, K.H., Ravishankar Ram, M. and Kuppusamy, U.R. (2016). Monoterpenes: novel insights into their biological effects and roles on glucose uptake and lipid metabolism in 3T3-L1 adipocytes. Food Chem. 196: 242-250. doi: 10.1016/j.foodchem.2015.09.042
   PubMed Web of Science ®Google Scholar
• Adams, T.B., Gavin, C.L, McGowen, M.M., Waddell, W.J., Cohen, S.M., Feron, V.J., Marnett, L.J., Munro, I.C., Portoghese, P.S., Rietjens, I.M. and Smith, R.L. (2011). The FEMA GRAS assessment of aliphatic and aromatic terpene hydrocarbons used as flavor ingredients. Food Chem. Toxicol. 49(10): 2471-2494. doi: 10.1016/j.fct.2011.06.011
   PubMed Web of Science ®Google Scholar
• Lin, J.J., Hsu, S.C., Lu, K.W., Ma, Y.S., Wu, C.C., Lu, H.F., Chen, J.C., Lin, J.G., Wu, P.P. and Chung, J.G. (2015). Alpha-phellandrene-induced apoptosis in mice leukemia WEHI-3 cells in vitro. Environ. Toxicol. 31(11): 1640-1651. doi: 10.1002/tox.22168
   PubMed Web of Science ®Google Scholar
• Lin, J.J., Lin, J.U.H., Hsu, S.C., Weng, S.W., Huang, Y.I.P., Tang, N.Y., Lin, J.G. and Chung, J.G. (2013). Alpha-phellandrene promotes immune responses in normal mice through enhancing macrophage phagocytosis and natural killer cell activities. In Vivo. 27(6): 809-814.
   PubMed Web of Science ®Google Scholar
• Lin, J.J., Lu, K.W., Ma, Y.S., Tang, N.Y., Wu, P.P., Wu, C.C., Lu, H.F., Lin, J.G. and Chung, J.G. (2014). Alpha-phellandrene, a natural active monoterpene, influences a murine WEHI-3 Leukemia model in Vivo by enhancing macrophage phagocytosis and natural killer cell activity. In Vivo. 28(4): 583-588.
   PubMed Web of Science ®Google Scholar
• Lin, J.J., Wu, C.C., Hsu, S.C., Weng, S.W., Ma, Y.S., Huang, Y.P., Lin, J.G. and Chung, J.G. (2014). Alpha-phellandrene-induced DNA damage and affect DNA repair protein expression in WEHI-3 murine leukemia cells in Vitro. Environ. Toxicol. 30(11): 1322-1330. doi: 10.1002/tox.22003
   PubMed Web of Science ®Google Scholar
• Lin, J.J., Yu, C.C., Lu, K.W., Chang, S.J., Yu, F.S., Liao, C.L., Lin, J.G. and Chung, J.G. (2014). Alpha-phellandrene alters expression of genes associated with DNA damage, cell cycle, and apoptosis in murine leukemia WEHI-3 cells. Anticancer Res. 34(8): 4161-4180.
   PubMed Web of Science ®Google Scholar
• Pinheiro-Neto, F.R., Lopes, E.M., Acha, B.T., Gomes, L.D.S., Dias, W.A., Reis Filho, A.C.D., Leal, B.S., Rodrigues, D.C.D.N., Silva, J.D.N., Dittz, D., Ferreira, P.M.P. and Almeida, F.R.C. (2021). Alpha-Phellandrene exhibits antinociceptive and tumor-reducing effects in a mouse model of oncologic pain. Toxicol. Appl. Pharmacol. 418: 115497. doi: 10.1016/j.taap.2021.115497
   PubMed Web of Science ®Google Scholar
• Sybilska, D., Kowalczyk, J., Asztemborska, M., Ochocka, R.J. and Lamparczyk, H. (1994). Chromatographic studies of the enantiomeric composition of some therapeutic compositions applied in the treatment of liver and kidney diseases. J. Chromatogr. A. 665(1): 67-73. doi: 10.1016/0021-9673(94)87033-0
   PubMed Web of Science ®Google Scholar
• Alma, M.H., Nitz, S., Kollmannsberger, H., Digrak, M., Efe, F.T. and Yilmaz, N. (2004). Chemical composition and antimicrobial activity of the essential oils from the gum of Turkish pistachio (Pistacia vera L.). J. Agric. Food Chem. 52(12): 3911-3914. doi: 10.1021/jf040014e
   PubMed Web of Science ®Google Scholar
• Rivas da Silva, A.C., Lopes, P.M., Barros de Azevedo, M.M., Costa, D.C., Alviano, C.S. and Alviano, D.S. (2012). Biological activities of α-pinene and β-pinene enantiomers. Molecules. 17(6): 6305-6316. doi: 10.3390/molecules17066305
   PubMed Web of Science ®Google Scholar
• Zapata, B., Durán, C., Stashenko, E., Correa-Royero, J. and Betancur-Galvis, L. (2009). Actividad citotóxica de aceites esenciales de Lippia origanoides H.B.K. y componentes mayoritarios. Salud UIS. 41: 215-222
   Google Scholar
• Winnacker, M. (2018). Pinenes: Abundant and Renewable Building Blocks for a Variety of Sustainable Polymers. Angew. Chem. Int. Ed. 57(44): 14362-14371. doi: 10.1002/anie.201804009
   PubMed Web of Science ®Google Scholar
• Zhou, J.Y., Tang, F.D., Mao, G.G. and Bian, R.L. (2004). Efect of alpha-pinene on nuclear translocation of NF-kappa B in THP-1 cells. Acta Pharmacol. Sin. 25(4): 480-484.
   PubMed Web of Science ®Google Scholar
• Salehi, B., Upadhyay, S., Erdogan Orhan, I., Kumar Jugran, A., Jayaweera, S.L D, Dias, D.A., Sharopov, F., Taheri, Y., Martins, N., Baghalpour, N., Cho, W.C. and Sharifi-Rad, J. (2019). Therapeutic potential of α- and β-pinene: A miracle gift of nature. Biomolecules. 9(11): 738. doi: 10.3390/biom9110738
   PubMed Web of Science ®Google Scholar
• Balahbib, A., El Omari, N., Hachlafi, N.E., Lakhdar, F., El Menyiy, N., Salhi, N., Mrabti, H.N., Bakrim, S., Zengin, G. and Bouyahya, A. (2021). Health beneficial and pharmacological properties of p-cymene. Food Chem. Toxicol. 153: 112259. doi: 10.1016/j.fct.2021.112259
   PubMed Web of Science ®Google Scholar