Search for Author, Title, Keyword
Optimization of Distillation Conditions for Improved Recovery of Phthalides from Celery (Apium graveolens L.) Seeds
More details
Hide details
Department of Pharmacognosy, Faculty of Pharmacy, Medical University of Gdańsk, Hallera 107, 80-416 Gdańsk, Poland
Department of Biopharmacy, Ludwik Rydygier Collegium Medicum in Bydgoszcz, Nicolaus Copernicus University in Toruń, Jurasza 2, 85-089 Bydgoszcz, Poland
Submission date: 2021-02-04
Final revision date: 2021-05-17
Acceptance date: 2021-05-18
Online publication date: 2021-06-07
Publication date: 2021-06-07
Corresponding author
Adam Kokotkiewicz   

Department of Pharmacognosy, Faculty of Pharmacy, Medical University of Gdańsk, Hallera 107, 80-416 Gdańsk, Poland
Pol. J. Food Nutr. Sci. 2021;71(2):197-210
The essential oil of celery (Apium graveolens) is characterized by exceptionally high content of alkylphthalides. The mentioned compounds exhibit a number of biological effects (including hypotensive, lipid-lowering, neuroprotective, and cytotoxic) and are also responsible for distinctive aroma of the plant. In the current work, parameters of conventional hydrodistillation (HD) and simultaneous distillation-extraction (SDE) were optimized to obtain phthalide-enriched fractions of celery seeds. A positive correlation was shown between hydrodistillation time and improved essential oil and phthalide yields. The 6-h HD of comminuted seeds yielded essential oil (2.9%) with a higher total phthalide content (51%), as compared to the samples collected after 1.5-3.0 h, which gave 2.4-2.7% of oil containing 24.6-39.2% of total phthalides. The oil contained sedanenolide (36.7%), 3-n-butylphthalide (13.1%), and sedanolide (1.1%). A further increase in the total phthalide content was achieved by omitting the size reduction step prior to hydrodistillation (68.8%) and utilization of the salting-out effect (84.3%). Enzyme pretreatment had a negligible effect on essential oil and phthalide yields. The change of distillation mode from HD to SDE significantly increased the oil yield of whole seeds (from 2.8 to 5.8% for 6 h processing) while maintaining its high phthalide content (62.5%), which translated to an increase in the total phthalide yield from 19.4 to 36.0 g/kg.
This research received no external funding.
Bartsch, A., Hammerschmidt, F.-J. (1993). Separation of fragrance materials from perfumed consumer products. Perfumer & Flavorist, 18, 41–48.
Bicchi, C. (2000). Essential oils/Gas chromatography. In I.D. Wilson, C. Poole, M. Cooke (Eds.), Encyclopedia of Separation Science, Academic Press, Cambridge, UK, pp. 2744–2755.
Chaintreau, A. (2001). Simultaneous distillation–extraction: from birth to maturity—review. Flavour and Fragrance Journal, 16(2), 136–148.
Dąbrowska, J.A., Kunicka-Styczyńska, A., Śmigielski, K.B. (2020). Biological, chemical, and aroma profiles of essential oil from waste celery seeds (Apium graveolens L.). Journal of Essential Oil Research, 32(4), 308-315.
El-Beltagi, H.S., Dhawi, F., Aly, A.A., El-Ansary, A.E. (2020). Chemical compositions and biological activities of the essential oils from gamma irradiated celery (Apium graveolens L.) seeds. Notulae Botanicae Horti Agrobotanici Cluj-Napoca, 48(4), 2114-2133.
Filly, A., Fabiano-Tixier, A.S., Louis, C., Fernandez, X., Chemat, F. (2016). Water as a green solvent combined with different techniques for extraction of essential oil from lavender flowers. Comptes Rendus Chimie, 19(6), 707–717.
Gong, S., Zhang, J., Guo, Z., Fu, W. (2018). Senkyunolide A protects neural cells against corticosterone-induced apoptosis by modulating protein phosphatase 2A and α-synuclein signaling. Drug Design, Development and Therapy, 12, 1865–1879.
Hsieh, S.L., Chen, C.T., Wang, J.J., Kuo, Y.H., Li, C.C., Hsieh, L.C., Wu, C.C. (2015). Sedanolide induces autophagy through the PI3K, p53 and NF-κB signaling pathways in human liver cancer cells. International Journal of Oncology, 47(6), 2240–2246.
Huang, L., Wang, S., Ma, F., Zhang, Y., Peng, Y., Xing, C., Feng, Y., Wang, X., Peng, Y. (2018). From stroke to neurodegenerative diseases: The multi-target neuroprotective effects of 3-n-butylphthalide and its derivatives. Pharmacological Research, 135, 201–211.
Jain, M.P., Sama, J.K., Jain, S.M., Sharma, V.K., Singh, B. (2003). An improved method for the recovery of essential oil from celery seeds. Indian Journal of Chemical Technology, 10(4), 370–372.
Kokotkiewicz, A., Luczkiewicz, M. (2016). Chapter 37 – Celery (Apium graveolens var. dulce (Mill.) Pers.) oils. In V.R. Preedy (Ed.), Essential Oils in Food Preservation, Flavor and Safety, Academic Press, pp. 325–338.
Kurobayashi, Y., Kouno, E., Fujita, A., Morimitsu, Y., Kubota, K. (2006). Potent odorants characterize the aroma quality of leaves and stalks in raw and boiled celery. Bioscience, Biotechnology, and Biochemistry, 70(4), 958–965.
Lei, W., Deng, Y.F., Hu, X.Y., Ni, J.N., Jiang, M., Bai, G. (2019). Phthalides, senkyunolide A and ligustilide, show immunomodulatory effect in improving atherosclerosis, through inhibiting AP-1 and NF-κB expression. Biomedicine & Pharmacotherapy, 117, 109074.
León, A., Del-Ángel, M., Ávila, J.L., Delgado, G. (2017). Phthalides: Distribution in nature, chemical reactivity, synthesis, and biological activity. In A.D. Kinghorn, H. Falk, S. Gibbons, J. Kobayashi (Eds), Progress in the Chemistry of Organic Natural Products, Volume 104, Springer, pp. 127-246.
Li, S.-L., Chan, S.S.-K., Lin, G., Ling, L., Yan, R., Chung, H.-S., Tam, Y.-K. (2003). Simultaneous analysis of seventeen chemical ingredients of Ligusticum chuanxiong by on-line high performance liquid chromatography-diode array detector-mass spectrometry. Planta Medica, 69(5), 445–451.
Liu, M.M., Huang, K.M., Qian, L., Chatterjee, P., Zhang, S., Li, R., Zhou, S., Wang, Z., Luo, Y., Huang, Y. (2018). Effects of bioactive constituents in the Traditional Chinese Medicinal formula Si–Wu–Tang on Nrf2 signaling and neoplastic cellular transformation. Phytomedicine, 40, 1–9.
Ludwiczuk, A., Najda, A. B., Wolski, T., Baj, T. (2001). Chromatographic determination of the content and the composition of extracts and essential oils from the fruits of three varieties of stalk celery (Apium graveolens L. var. dulce Mill. Pers.). Journal of Planar Chromatography—Modern TLC, 14(6), 400–404.
MacLeod, G., Ames, J.M. (1989). Volatile components of celery and celeriac. Phytochemistry, 28(7), 1817–1824.
Malhotra, S.K. (2006). 18 – Celery. In K.V. Peter (Ed.), Handbook of Herbs and Spices, Volume 3, Academic Press, pp. 317–336.
Mukhopadhyay, M. (2000). Spice extracts. In M. Mukhopadhyay (Ed.), Natural Extracts Using Supercritical Carbon Dioxide (1st ed.), CRC Press, Boca Raton, pp. 177-200.
Naqvi, A.A., Mandal, S., Chattopadhyay, A., Prasad, A. (2002). Salt effect on the quality and recovery of essential oil of citronella (Cymbopogon winterianus Jowitt). Flavour and Fragrance Journal, 17(2), 109–110.
Niu, Z.Q., Sun, Y.M., Niu, F., Han, J., Chen, D.W. (2008). Study of electrospray ionization tandem mass spectrometry of the benzofuranone compounds. Chinese Chemical Letters, 19(3), 324–328.
Rożek, E., Nurzyńska-Wierdak, R., Sałata, A., Gumiela, P. (2016). The chemical composition of the essential oil of leaf celery (Apium graveolens L. var. secalinum alef.) under the plants' irrigation and harvesting method. Acta Scientiarum Polonorum. Hortorum Cultus, 15(1), 149-159.
Salehi, B., Venditti, A., Frezza, C., Yücetepe, A., Altunta, Ü., Uluata, S., Butnariu, M., Sarac, I., Shaheen, S., Petropoulos, S.A., Matthews, K.R., Kılıç, C.S., Atanassova, M., Adetunji, C.O., Ademiluyi, A.O., Özçelik, B., Fokou, P.V.T., Martins, N., Cho, W.C., Sharifi-Rad, J. (2019). Apium plants: Beyond simple food and phytopharmacological applications. Applied Sciences, 9(17), art. no. 3547.
Sgorbini, B., Cagliero, C., Pagani, A., Sganzerla, M., Boggia, L., Bicchi, C., Rubiolo, P. (2015). Determination of free and glucosidically-bound volatiles in plants. Two case studies: L-menthol in peppermint (Mentha x piperita L.) and eugenol in clove (Syzygium aromaticum (L.) Merr. & L.M.Perry). Phytochemistry, 117, 296–305.
Shamspur, T., Mohamadi, M., Mostafavi, A. (2012). The effects of onion and salt treatments on essential oil content and composition of Rosa damascena Mill. Industrial Crops and Products, 37(1), 451–456.
Sowbhagya, H.B. (2014). Chemistry, technology, and nutraceutical functions of celery (Apium graveolens L.): an overview. Critical Reviews in Food Science and Nutrition, 54(3), 389–398.
Sowbhagya, H.B., Purnima, K.T., Florence, S.P., Appu Rao, A.G., Srinivas, P. (2009). Evaluation of enzyme-assisted extraction on quality of garlic volatile oil. Food Chemistry, 113(4), 1234–1238.
Sowbhagya, H.B., Sampathu, S.R., Krishnamurthy, N. (2007). Evaluation of size reduction on the yield and quality of celery seed oil. Journal of Food Engineering, 80(4), 1255–1260.
Sowbhagya, H.B., Srinivas, P. (2013). Enrichment of bio-active phthalides in celery seed oil. Journal of Pharmacy and Nutrition Sciences, 3, 250–257.
Sowbhagya, H.B., Srinivas, P., Krishnamurthy, N. (2010). Effect of enzymes on extraction of volatiles from celery seeds. Food Chemistry 120(1), 230–234.
Tang, J., Zhang, Y., Hartman, T.G., Rosen, R.T., Ho, C.-T. (1990). Free and glycosidically bound volatile compounds in fresh celery (Apium graveolens L.). Journal of Agricultural and Food Chemistry, 38(10), 1937–1940.
Turner, L., Lignou, S., Gawthrop, F., Wagstaff, C. (2021). Investigating the factors that influence the aroma profile of Apium graveolens: A review. Food Chemistry, 345, art. no. 128673.
Van Wassenhove, F., Dirinck, P., Vulsteke, G., Schamp, N. (1990). Aromatic volatile composition of celery and celeriac cultivars. HortScience, 25(5), 556–559.
Venditti, A. (2020). What is and what should never be: artifacts, improbable phytochemicals, contaminants and natural products. Natural Product Research, 34(7), 1014-1031.
Wang, N., Zhao, X., Li, Y., Cheng, C., Huai, J., Bi, K., Dai, R. (2018). Identification of the absorbed components and metabolites of modified Huo Luo Xiao Ling Dan in Rat Plasma by UHPLC-Q-TOF/MS/MS. Biomedical Chromatography, 32(6), art. no. e4195.
Zhang, L., Zhu, L., Wang, Y., Jiang, Z., Chai, X., Zhu, Y., Gao, X., Qi, A. (2012). Characterization and quantification of major constituents of Xue Fu Zhu Yu by UPLC-DAD–MS/MS. Journal of Pharmaceutical and Biomedical Analysis, 62, 203–209.
Zhang, X., Xiao, H., Xu, Q., Li, X., Wang, J., Liang, X. (2003). Characterization of phthalides in Ligusticum chuanxiong by liquid chromatographic-atmospheric pressure chemical ionization-mass spectrometry. Journal of Chromatographic Science, 41(8), 428–433.
Zheng, G.Q., Kenney, P.M., Zhang, J., Lam, L.K. (1993). Chemoprevention of benzo[a]pyrene-induced forestomach cancer in mice by natural phthalides from celery seed oil. Nutrition and Cancer, 19, 77–86.
Zorga, J., Kunicka-Styczyńska, A., Gruska, R., Śmigielski, K. (2020). Ultrasound-assisted hydrodistillation of essential oil from celery seeds (Apium graveolens L.) and its biological and aroma profiles. Molecules, 25(22), art. no. 5322.
Zuo, A., Wang, L., Xiao, H., Li, L., Liu, Y., Yi, J. (2011). Identification of the absorbed components and metabolites in rat plasma after oral administration of Rhizoma chuanxiong decoction by HPLC–ESI-MS/MS. Journal of Pharmaceutical and Biomedical Analysis, 56(5), 1046–1056.
An Overview of Natural and Synthetic Phthalides Involved in Cancer Studies: Past, Present, and Future
Bleda Sadıkoğulları, Pelin Şenel, Nejla Çini, Abdullah Faysal, Mustafa Odabaşoğlu, Ayşe Özdemir, Ayşegül Gölcü
Advances in the phytochemistry and pharmacology of plant-derived phthalides
Yulong Chen, QingZhou Cheng, Site Lv, Zhen Kang, Shan Zeng
Journals System - logo
Scroll to top