Compositional Analyses and Cytotoxic Activity of Star Anise (Illicium Verum) Essential Oils in Vietnam
Main Article Content
Abstract
By means of the gas chromatography-mass spectrometry (GC/MS) method, 21 volatile components have been identified in the essential oils of fruits and the leaves of star anise (Illicium verum Hook. f., Illiciaceae) in Vietnam, in which, essential oil of star anise fruits has 18 components, essential oil of star anise leaves has 16 components, with content have been determined more than 98.60% total compounds of essential oil. The major compound was identified as trans- anethole with 87.05% in leaves essential oil and 90.12% in fruits essential oil. The in vitro anti-cancer activity of star anise essential oil was evaluated by cytotoxicity assay. The results showed that the essential oil obtained from leaves of star anise inhibited the grow of liver cancer cell (IC50 = 10.22 µg/ml) and colon cancer cell (IC50 = 6.26 µg/ml). The essential oil obtained from fruits of star anise inhibited the grow of liver cancer cell and colon cancer cell with the IC50 values of 5.93 and 3.20 µg/ml, respectively.
Keywords
Illicium verum, star anise, essential oils, anticancer, cytotoxicity assay, GC/MS
Article Details
References
[1] D. T. Loi, Vietnam medicinal plants and herbs, Vietnam Medical Publishing House, Hanoi, 2004, pp. 524-525.
[2] L. Rocha, L. Armando, C. Tietbohl, Essential oils in food preservation, Flavor and Safety, UK: Elsevier, 2016, pp. 751-756.
[3] G. Singh, S. Maurya, M.P. de Lampasona, C. Catalan, Chemical constituents, antimicrobial investigations and antioxidative potential of volatile oil and acetone extract of star anise fruits, J. Sci. Food Agric., vol. 86, no. 1, pp. 111-121, Jan. 2006 https://doi.org/10.1002/jsfa.2277.
[4] C. H. Yang, F. R. Chang, H. W. Chang, S. M. Wang, M.C. Hsieh, L. Y. Chuang, Investigation of the antioxidant activity of Illicium verum extracts, J. Med. Plant Res., vol. 6, no. 2, pp. 314-324, Jan. 2012, https://doi.org/10.5897/JMPR11.983.
[5] J. Y. Kim, S. S. Kim, T. H. Oh, J. S. Baik, G. Song, N. H. Lee, C. G. Hyun, Chemical composition, antioxidant, anti-elastase, and anti-inflammatory activities of Illicium anisatum essential oil, Acta Pharm., vol. 59, no. 3, pp. 289-300, Sep. 2009 https://doi.org/10.2478/v10007-009-0022-y
[6] M. De, A. K. De, P. Sen, A. B. Banerjee, Antimicrobial properties of star anise (Illicium verum Hook f), Phytother. Res., vol.16, no. 1, pp. 94-95, Feb. 2002 https://doi.org/10.1002/ptr.989.
[7] L. Wei, R. Hua, M. Li, Y. Huang, S. Li, Y. He, Z. Shen, Chemical composition and biological activity of star anise Illicium verum extracts against maize weevil, Sitophilus zeamais adults, J. Insect Sci., vol. 14, no. 1, pp. 1-13, Jun. 2014, https://doi.org/10.1093/jis/14.1.80.
[8] Sigma Technical Bulletin, Retention index standard for gas chromatography, 2002.
[9] R.P. Adams, Identification of essential oil components by gas chromatography/quadrupole mass spectrometry, 4th Edition, Carol Stream. IL, Allured Publishing Corporation, 2010.
[10] National Institute of Standards and Technology, Data from NIST standard reference database no. 69, Chemistry web book, 2011. https://doi.org/10.18434/T4D303
[11] Jun Zhang, Aiqin Fang,1 Bing Wang, Seong Ho Kim, Bogdan Bogdanov, Zhanxiang Zhou, Craig McClain, and Xiang Zhang, iMatch: A retention index tool for analysis of gas chromatography-mass spectrometry data, J. Chromatogr. A, vol. 1218, no. 2011, pp. 6522-6530, Jul. 2011 https://doi.org/10.1016/j.chroma.2011.07.039
[12] P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J.T. Warren, H. Bokesch, S. Kenney, M.R. Boyd, New colorimetric cytotoxic assay for anticancer-drug screening, J. Natl. Cancer Inst., vol. 82, no. 13, pp. 1107-1112, Jul. 1990 https://doi.org/10.1093/jnci/82.13.1107
[13] A. Monks, D. Scudiero, P. Skehan, R. Shoemaker, K. Paull, D. Vistica, C. Hose, J. Langley, P. Cronise, A. Vaigro-Wolff, Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines, J. Natl. Cancer Inst., vol. 83, no. 11, pp. 757-766, Jun. 1991 https://doi.org/10.1093/jnci/83.11.757
[14] N. X. Cuong, T. T. H. Hanh, N. P. Thao, N. Van Thanh, N. H. Nam, D. C. Thung, P. Van Kiem, C. Van Minh, Cytotoxic triterpene saponins from Cercodemas anceps, Bioorg. Med. Chem. Lett., vol. 25, no. 16, pp. 3151-3156, Aug. 2015 https://doi.org/10.1016/j.bmcl.2015.06.005.
[15] L. Vajrabhaya, S. Korsuwannawong, Cytotoxicity evaluation of a Thai herb using tetrazolium (MTT) and sulforhodamine B (SRB) assays, J. Anal. Sci. Technol., vol. 15, Jul. 2018, https://doi.org/10.1186/s40543-018-0146-0.
[16] Vietnam Ministry of Science and Technology, Vietnam Standard 8853:2001 Oil of star anise (Illicium verum Hook. f.), 2011.
[17] S. E. Aly, B. A. Sabry, M. S. Shaheen, A. S. Hathout, Assessment of antimycotoxigenic and antioxidant activity of star anise (Illicium verum) in vitro, J. Saudi Soc. Agric. Sci., vol, 15, no. 1, pp. 20-27, Jan. 2016 https://doi.org/10.1016/j.jssas.2014.05.003.
[18] M. Wichtl, Herbal drugs and phytopharmaceuticals: A handbook for practice on a scientific basis, MedPharm GmbH Scientific Publishers, Stuttgart, 2014, pp. 566 https://doi.org/10.1002/ffj.2730100512
[19] Y. Nakagawa, T. Suzuki, Cytotoxic and xenoestrogenic effects via biotransformation of trans-anethole on isolated rat hepatocytes and cultured MCF-7 human breast cancer cells, Biochem. Pharmacol., vol. 6, no.1, pp. 663-673, Jul. 2003 https://doi.org/10.1016/S0006-2952(03)00208-9
[20] E. J. Choo, Y. H. Rhee, S. J. Jeong, H. J. Lee, H. S. Kim, H. S. Ko, J. H. Kim, T. R. Kwon, J. H. Jung, J. H. Kim, H. J. Lee, E. O. Lee, D. K. Kim, C. Y. Chen, S. H. Kim, Anethole exerts antimetatstaic activity via inhibition of matrix metalloproteinase 2/9 and AKT/mitogen-activated kinase/nuclear factor kappa B signaling pathways, Biol. Pharm. Bull., vol. 34, no. 1, pp. 41-46, Jan. 2011 https://doi.org/10.1248/bpb.34.41
[21] V. Marinov, S. Valcheva-Kuzmanova, Review on the pharmacological activities of anethole, Scripta Scientifica Pharmaceutica, vol. 2, no. 2, pp. 14-19, Nov. 2015 http://doi.org/10.14748/ssp.v2i2.1141
[22] Muhammad Asif, Ashwaq Hamid Salem Yehya, Majed Ahmed Al-Mansoub, Vageesh Revadigar, Mohammed Oday Ezzat, Mohamed B. Khadeer Ahamed, Chern Ein Oon, Vikneswaran Murugaiyah, Aman Shah Abdul Majid, Amin Malik Shah Abdul Majid, Anticancer attributes of Illicium verum essential oils against colon cancer, S. Afr. J. Bot., vol. 103, pp. 156-161, Mar. 2016 https://doi.org/10.1016/j.sajb.2015.08.017
[2] L. Rocha, L. Armando, C. Tietbohl, Essential oils in food preservation, Flavor and Safety, UK: Elsevier, 2016, pp. 751-756.
[3] G. Singh, S. Maurya, M.P. de Lampasona, C. Catalan, Chemical constituents, antimicrobial investigations and antioxidative potential of volatile oil and acetone extract of star anise fruits, J. Sci. Food Agric., vol. 86, no. 1, pp. 111-121, Jan. 2006 https://doi.org/10.1002/jsfa.2277.
[4] C. H. Yang, F. R. Chang, H. W. Chang, S. M. Wang, M.C. Hsieh, L. Y. Chuang, Investigation of the antioxidant activity of Illicium verum extracts, J. Med. Plant Res., vol. 6, no. 2, pp. 314-324, Jan. 2012, https://doi.org/10.5897/JMPR11.983.
[5] J. Y. Kim, S. S. Kim, T. H. Oh, J. S. Baik, G. Song, N. H. Lee, C. G. Hyun, Chemical composition, antioxidant, anti-elastase, and anti-inflammatory activities of Illicium anisatum essential oil, Acta Pharm., vol. 59, no. 3, pp. 289-300, Sep. 2009 https://doi.org/10.2478/v10007-009-0022-y
[6] M. De, A. K. De, P. Sen, A. B. Banerjee, Antimicrobial properties of star anise (Illicium verum Hook f), Phytother. Res., vol.16, no. 1, pp. 94-95, Feb. 2002 https://doi.org/10.1002/ptr.989.
[7] L. Wei, R. Hua, M. Li, Y. Huang, S. Li, Y. He, Z. Shen, Chemical composition and biological activity of star anise Illicium verum extracts against maize weevil, Sitophilus zeamais adults, J. Insect Sci., vol. 14, no. 1, pp. 1-13, Jun. 2014, https://doi.org/10.1093/jis/14.1.80.
[8] Sigma Technical Bulletin, Retention index standard for gas chromatography, 2002.
[9] R.P. Adams, Identification of essential oil components by gas chromatography/quadrupole mass spectrometry, 4th Edition, Carol Stream. IL, Allured Publishing Corporation, 2010.
[10] National Institute of Standards and Technology, Data from NIST standard reference database no. 69, Chemistry web book, 2011. https://doi.org/10.18434/T4D303
[11] Jun Zhang, Aiqin Fang,1 Bing Wang, Seong Ho Kim, Bogdan Bogdanov, Zhanxiang Zhou, Craig McClain, and Xiang Zhang, iMatch: A retention index tool for analysis of gas chromatography-mass spectrometry data, J. Chromatogr. A, vol. 1218, no. 2011, pp. 6522-6530, Jul. 2011 https://doi.org/10.1016/j.chroma.2011.07.039
[12] P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J.T. Warren, H. Bokesch, S. Kenney, M.R. Boyd, New colorimetric cytotoxic assay for anticancer-drug screening, J. Natl. Cancer Inst., vol. 82, no. 13, pp. 1107-1112, Jul. 1990 https://doi.org/10.1093/jnci/82.13.1107
[13] A. Monks, D. Scudiero, P. Skehan, R. Shoemaker, K. Paull, D. Vistica, C. Hose, J. Langley, P. Cronise, A. Vaigro-Wolff, Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines, J. Natl. Cancer Inst., vol. 83, no. 11, pp. 757-766, Jun. 1991 https://doi.org/10.1093/jnci/83.11.757
[14] N. X. Cuong, T. T. H. Hanh, N. P. Thao, N. Van Thanh, N. H. Nam, D. C. Thung, P. Van Kiem, C. Van Minh, Cytotoxic triterpene saponins from Cercodemas anceps, Bioorg. Med. Chem. Lett., vol. 25, no. 16, pp. 3151-3156, Aug. 2015 https://doi.org/10.1016/j.bmcl.2015.06.005.
[15] L. Vajrabhaya, S. Korsuwannawong, Cytotoxicity evaluation of a Thai herb using tetrazolium (MTT) and sulforhodamine B (SRB) assays, J. Anal. Sci. Technol., vol. 15, Jul. 2018, https://doi.org/10.1186/s40543-018-0146-0.
[16] Vietnam Ministry of Science and Technology, Vietnam Standard 8853:2001 Oil of star anise (Illicium verum Hook. f.), 2011.
[17] S. E. Aly, B. A. Sabry, M. S. Shaheen, A. S. Hathout, Assessment of antimycotoxigenic and antioxidant activity of star anise (Illicium verum) in vitro, J. Saudi Soc. Agric. Sci., vol, 15, no. 1, pp. 20-27, Jan. 2016 https://doi.org/10.1016/j.jssas.2014.05.003.
[18] M. Wichtl, Herbal drugs and phytopharmaceuticals: A handbook for practice on a scientific basis, MedPharm GmbH Scientific Publishers, Stuttgart, 2014, pp. 566 https://doi.org/10.1002/ffj.2730100512
[19] Y. Nakagawa, T. Suzuki, Cytotoxic and xenoestrogenic effects via biotransformation of trans-anethole on isolated rat hepatocytes and cultured MCF-7 human breast cancer cells, Biochem. Pharmacol., vol. 6, no.1, pp. 663-673, Jul. 2003 https://doi.org/10.1016/S0006-2952(03)00208-9
[20] E. J. Choo, Y. H. Rhee, S. J. Jeong, H. J. Lee, H. S. Kim, H. S. Ko, J. H. Kim, T. R. Kwon, J. H. Jung, J. H. Kim, H. J. Lee, E. O. Lee, D. K. Kim, C. Y. Chen, S. H. Kim, Anethole exerts antimetatstaic activity via inhibition of matrix metalloproteinase 2/9 and AKT/mitogen-activated kinase/nuclear factor kappa B signaling pathways, Biol. Pharm. Bull., vol. 34, no. 1, pp. 41-46, Jan. 2011 https://doi.org/10.1248/bpb.34.41
[21] V. Marinov, S. Valcheva-Kuzmanova, Review on the pharmacological activities of anethole, Scripta Scientifica Pharmaceutica, vol. 2, no. 2, pp. 14-19, Nov. 2015 http://doi.org/10.14748/ssp.v2i2.1141
[22] Muhammad Asif, Ashwaq Hamid Salem Yehya, Majed Ahmed Al-Mansoub, Vageesh Revadigar, Mohammed Oday Ezzat, Mohamed B. Khadeer Ahamed, Chern Ein Oon, Vikneswaran Murugaiyah, Aman Shah Abdul Majid, Amin Malik Shah Abdul Majid, Anticancer attributes of Illicium verum essential oils against colon cancer, S. Afr. J. Bot., vol. 103, pp. 156-161, Mar. 2016 https://doi.org/10.1016/j.sajb.2015.08.017