Chemical composition and cytotoxicity of Araucaria heterophylla (Salisb.) franco essential oils

Abstract

The Norfolk Island pine, Araucaria heterophylla (Salisb.) Franco (Araucariaceae), is a plant that exhibits several pharmacological potentials. Essential oils (EOs) from the plant’s fresh stem bark (FRS) and dry stem bark (DRS) were hydrodistilled in an all-glass Clevenger apparatus and further characterized by Gas Chromatography-Mass Spectrometry analysis. Using Artemia salina eggs hatched in sea water, the brine shrimp lethality assay was carried out for toxicity. The FRS and DRS yielded 0.33% and 0.29% EOs, respectively, constituting 48 and 42 compounds, representing 94.38% and 84.30% of the total oil fractions. The classes of compounds identified in the FRS and DRS EOs, respectively, include sesquiterpenes (40.8% and 41.36%), oxygenated sesquiterpenes (34.93% and 34.22%), oxygenated monoterpenes (11.58% and 2.84%), diterpenes (3.39% and 2.85%), oxygenated diterpenes (3.68% and 2.29%), and oxygenated triterpenes (0.74%, only in the DRS). The major constituents in the FRS EOs are spathulenol (12.12%), germacrene B (10.63%), dihydroedulan I (10.23%), γ-cadinene (6.90%), (-)-globulol(4.67%), aromadendrene (3.62%) and copaene (3.34%) while spathulenol (16.13%), germacrene B (10.37%), aromadendrene (4.93%), copaene (3.54%), β-panasinsene (3.06%) and guaiol (2.99%) majorly constitute the DRS oil. Constituents common and as well dominant in the two EOs include Spathulenol, Germacrene B, Aromadendrene and Copaene. The result of the cytotoxicity analysis showed that both the fresh and dry essential oils have LC50 of 10 ppm. A LC50<100 ppm indicates high toxicity, thus, the EOs possess significant cytotoxicity against A. salina.

Keywords

• Araucaria heterophylla
• GC and GC-MS
• Essential oil
• Spathulenol
• Cytotoxicity

References

1. Abd-ElGawad, A.M., Saleh, I., El-Razek, M.H.A., Elkarim, A.S.A., El-Amier, Y.A., Mohamed, T.A., El Gendy, A.E-N.G., Afifi, S.M., Esatbeyoglu, T., & Elshamy, A.I. (2023). Chemical profiling of significant antioxidant and phytotoxic microwave-extracted essential oil from Araucaria heterophylla Resin. Separations, 10, 141. https://doi.org/10.3390/separations10020141
2. Abdel-Sattar, E., Monem, A.R.A., Ezzat, S.M., El-Halawany, A.M., & Mouneir, S.M. (2009). Chemical and biological investigation of Araucaria heterophylla Salisb. resin. Z. Naturforsch., C 64, 819-823.
3. Aboaba, S., Akande, A., & Flamini, G. (2013). Chemical constituents, toxicity and antimicrobial activities of the essential oil from the leaves of Tectona grandis. Elixir Bio Technology, 61, 16795-16798.
4. Aboaba, S., Akande, A., & Flamini, G. (2014). Chemical composition and toxicity of essential oil of Vitellaria paradoxa (C.F. Gaertn.) from Nigeria. Journal of Essential Oil Bearing Plants, 17(1), 126-130. http://dx.doi.org/10.1080/0972060X.2014.884757
5. Adams, R.P. (2007). Identification of essential oil components by gas chromatography / quadrupole Mass Spectrometry (4th ed.). Allured Publishing, Carol Stream, Illinois, USA.
6. Akande, A., Aboaba, S., & Flamini, G. (2018). Variation in chemical constituents and anthelmintic activity of Albizia zygia (DC.) J.F.Macbr. essential oils from Ibadan, Nigeria. Journal of Science Research, 17, 30-37.
7. Ali, D.E, Abd el‑Aziz, M.M., Ibrahim, S.S.A., Sheta, E., & Abdel‑Sattar, E. (2023). Gastroprotective and anti‑Helicobacter pylori potentials of essential oils from the oleoresins of Araucaria bidwillii and Araucaria heterophylla. Inflammopharmacology, 31, 465-483. https://doi.org/10.1007/s10787-022-01112-w
8. Aslam, M.S., Choudhary, B.A., Uzair, M., & Ijaz, A.S. (2013). Phytochemical and ethno-pharmacological review of the genus Araucaria–review. Tropical Journal of Pharmaceutical Research, 12, 651-659.

9. Baz, M.M., Khater, H.F., Baeshen, R.S., Selim, A., Shaheen, E.S., El‐Sayed, Y.A., Salama, S.A., & Hegazy, M.M. (2022). Novel pesticidal efficacy of Araucaria heterophylla and Commiphora molmol extracts against Camel and Cattle blood‐sucking ectoparasites. Plants, 11, 1682. https://doi.org/10.3390/plants11131682
10. Beigi, M., Torki-Harchegani, M., & Pirbalouti, A.G. (2018). Quantity and chemical composition of essential oil of peppermint (Mentha × piperita L.) leaves under different drying methods. International Journal of Food Properties, 21(1), 267-276. https://doi.org/10.1080/10942912.2018.1453839
11. Branco, C.S., Rodrigues, T.S., Lima, É.D., Calloni, C., Scola, G., & Salvador, M. (2016). Chemical constituents and biological activities of Araucaria angustifolia (Bertol.) O. Kuntze: A review. Journal of Organic & Inorganic Chemistry, 2(1), 1. https://doi.org/10.21767/2472-1123.100008
12. Brophy, J.J., Goldsack, R.J., Wu, M.Z., Fookes, C.J.R., & Forster, P.I. (2000). The steam volatile oil of Wollemia nobilis and its comparison with other members of the Araucariaceae (Agathis and Araucaria). Biochemical Systematics and Ecology, 28(6), 563-578.
13. Caputo, L., Amato, G., de Bartolomeis, P., De Martino, L., Manna, F., Nazzaro, F., De Feo, V., & Barba, A.A. (2022). Impact of drying methods on the yield and chemistry of Origanum vulgare L. essential oil. Scientific Reports 12, 3845. https://doi.org/10.1038/s41598-022-07841-w
14. do Nascimento, K.F., Moreira, F.M.F., Santos, J.A., Kassuya, C.A.L., Croda, J.H.R., Cardoso, C.A.L., … Formagio, A.S.N. (2018). Antioxidant, anti-inflammatory, antiproliferative and antimycobacterial activities of the essential oil of Psidium guineense Sw. and spathulenol. Journal of Ethnopharmacology, 210, 351-358. http://dx.doi.org/10.1016/j.jep.2017.08.030
15. Elkady, W.M. & Ayoub, I.M. (2018). Chemical profiling and antiproliferative effect of essential oils of two Araucaria species cultivated in Egypt. Industrial Crops Products, 118, 188-195. https://doi.org/10.1016/j.indcrop.2018.03.051
16. Elshamy, A.I., Ammar, N.M., Hassan, H.A., Al-Rowaily, S.L., Ragab, T.I., El Gendy, A.G., & Abd-ElGawad, A.M. (2020). Essential oil and its nanoemulsion of Araucaria heterophylla Resin: Chemical characterization, anti-inflammatory, and antipyretic activities. Industrial Crops & Products, 148, 112272 (10 pp). https://doi.org/10.1016/j.indcrop.2020.112272
17. Ferrer, J.P., Zampini, I.C., Cuello, A.S., Francisco, M., Romero, A., Valdivia, D., Gonzalez, M., Salas, C., Lamar, A.S., & Isla, M.I. (2016). Cytotoxic compounds from aerial organs of Xanthium strumarium. Natural Product Communication, 11(3), 371-374.
18. Hazrati, S., Lotfi, K., Govahi, M., & Ebadi, M-T. (2021). A comparative study: Influence of various drying methods on essential oil components and biological properties of Stachys lavandulifolia. Food Science & Nutrition, 9, 2612-2619. https://doi.org/10.1002/fsn3.2218.
19. Hong, S.L., Lee, G-S., Abdul Rahman, S.N.S., Hamdi, O.A.A., Awang, K., Nugroho, N.A., & Malek, S.N.A. (2014). Essential oil content of the rhizome of Curcuma purpurascens Bl. (Temu Tis) and its antiproliferative effect on selected human carcinoma cell lines. Scientific World Journal, 2014, 397430. http://dx.doi.org/10.1155/2014/397430
20. Hosseini, K., Jasori, S., Delazar, A., Asgharian, P., & Tarhriz, V. (2021). Phytochemical analysis and anticancer activity of Falcaria vulgaris Bernh growing in Moghan plain, northwest of Iran. BMC Complementary Medicine and Therapies, 21, 294. https://doi.org/10.1186/s12906-021-03464-2
21. Jaramillo, D., Calva, J., Bec, N., Larroque, C., Vidari, G., & Armijos, C. (2022). Chemical characterization and biological activity of the essential oil from Araucaria brasiliensis collected in Ecuador. Molecules, 27, 3793. https://doi.org/10.3390/molecules27123793
22. Joulain, D., & Koening, W.A. (1998). The Atlas of Spectra Data of Sesquiterpene Hydrocarbons. EB- Verlag, Hamburg.
23. Manjima, R.B., Ramya, S., Kavithaa, K., Paulpandi, M., Saranya, T., Winster, S.B.H., Balachandar, V., & Arul, N. (2021). Spathulenol attenuates 6-hydroxydopamine inducedneurotoxicity in SH-SY5Y neuroblastoma cells. Gene Reports, 25, 101396. https://doi.org/10.1016/j.genrep.2021.101396
24. Michael, H.N., Awad, H.M., El-Sayed, N.H., & Pare, P.W. (2010). Chemical and antioxidant investigations: Norfolk pine needles (Araucaria excelsa). Pharmaceutical Biology, 48(5), 534-538.
25. Nascimento, L.D.d., Silva, S.G., Cascaes, M.M., Costa, K.S.d., Figueiredo, P.L.B., Costa, C.M.L., Andrade, E.H.d.A., & de Faria, L.J.G. (2021). Drying effects on chemical composition and antioxidant activity of Lippia thymoides essential oil, a natural source of thymol. Molecules, 26, 2621. https://doi.org/10.3390/molecules26092621
26. Oladimeji, A.O., Babatunde, O., Musa, R.T., M’civer, F.A., Lawal, A.T., & Ogunwande, I.A. (2016). GC-MS analysis and cytotoxic activity of essential oils from the leaves of Abrus precatorius L. Gaertn. Asian Pacific Journal of Tropical Disease, 6(5), 372-375. https://doi.org/10.1016/S2222-1808(15)61050-7
27. Shahabipour, S., Firuzi, O., Asadollahi, M., Miri, M., & Javidnia, K. (2013). Essential oil composition and cytotoxic activity of Libanotis transcaucasica Schischk. from Iran. Natural Products Chemistry & Research, 1(2), 108. https://doi.org/10.4172/2329-6836.1000108
28. Soliman, A.F., Sabry, M.A., & Abdelwahab, G. (2023). Araucaria heterophylla oleogum resin essential oil is a novel aldose reductase and butyryl choline esterase enzymes inhibitor: In vitro and in silico evidence. Scientific Reports, 13, 11446. https://doi.org/10.1038/s41598-023-38143-4
29. Stafford, F. (2016). The long, long life of trees. Yale University Press.
30. Tewari, L.M., Rana, L., Arya, S.K., Tewari, G., Chopra, N., Pandey, N.C., … Gahtori, R. (2019). Effect of drying on the essential oil traits and antioxidant potential Juglans regia L. leaves from Kumaun Himalaya. SN Applied Sciences, 1, 1606. https://doi.org/10.1007/s42452-019-1575-0
31. Verma, R.S., Padalia, R.C., Goswami, P., Verma, S.K., Chauhan, A., & Darokar, M.P. (2014). Chemical composition and antibacterial activity of foliage and resin essential oils of Araucaria cunninghamii Aiton ex D. Don and Araucaria heterophylla (Salisb.) Franco from India. Industrial Crops and Products, 61, 410 416. http://dx.doi.org/10.1016/j.indcrop.2014.07.040