Chemical composition, oxidative stability and antiproliferative activity of <em>Anethum graveolens</em> (dill) seed hexane extract

I. A. Nehdia; N. Abutaha; H. M. Sbihi; C. P. Tan; S. I. Al-Resayes

doi:10.3989/gya.0455191

Authors

I. A. Nehdia Chemistry Department, College of Science, King Saud University - Chemistry Department, Science College, Tunis El Manar University. https://orcid.org/0000-0001-9312-4683
N. Abutaha Bioproducts Researach Chair, Zoology Department, College of Science, King Saud University https://orcid.org/0000-0002-1887-7789
H. M. Sbihi Chemistry Department, College of Science, King Saud University https://orcid.org/0000-0002-0249-1224
C. P. Tan Department of Food Technology, Faculty of Food Science and Technology, Universiti Putra Malaysia https://orcid.org/0000-0003-4177-4072
S. I. Al-Resayes Chemistry Department, College of Science, King Saud University https://orcid.org/0000-0002-2498-3609

DOI:

https://doi.org/10.3989/gya.0455191

Keywords:

Anethum graveolens, Antiproliferative activity, Dill seed hexane extract, Oxidative stability, Thermal property, Volatile compounds

Abstract

This study aimed to evaluate the physicochemical properties, chemical composition, and antiproliferative activity of the hexane extract of Anethum graveolens L. (dill) seeds using gas chromatography mass spectrometry (GC-MS). Two fractions, namely the lipid fraction (74%) and volatile fraction (26%), were detected. The extract content of the seeds was about 9.4% and the extract had a pleasant spicy aroma. Oleic acid (52%), cis-vaccenic acid (6.2%), linoleic acid (5.5%), and palmitic acid (3.3%) were the key fatty acids in the lipid fraction, while apiol (23%) and d-carvone (2.4%) were the major volatile components. Tocols (tocopherols and tocotrienols) were also detected in the A. Graveolens extract (155 mg/100 g) and b-tocopherol was identified as the major tocol (71%). Dill extract showed a high oxidative stability (induction time = 45.22 h). Furthermore, dill extract showed antiproliferative activity against breast cancer cell lines.

Downloads

Download data is not yet available.

References

Aludatt MH, Rababah T, Alhamad MN, Gammoh S, Ereifej K, Al-Mahasneh MA, Kubow S. 2017. Application of olive oil as nutraceutical and pharmaceutical food: composition and biofunctional constituents and their roles in functionality, therapeutic, and nutraceutical properties. In: Grumezescu A, Holban AM, editors, Soft Chemistry and Food Fermentation. London, Academic Press; pp. 265-298. https://doi.org/10.1016/B978-0-12-811412-4.00010-2

Bozan B, Temelli F. 2008. Chemical composition and oxidative stability of flax, safflower and poppy seed and seed oils. Bioresour. Technol. 99, 6354-6359. https://doi.org/10.1016/j.biortech.2007.12.009 PMid:18198133

Bray F, Ferlay J, Soerjomataram I, Siegel RL, Torre LA, Jemal A. 2018. Global cancer statistics 2018: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA Cancer J. Clin. 68, 394-424. https://doi.org/10.3322/caac.21492 PMid:30207593

Djoussé L, Matsumoto C, Hanson NQ, Weir NL, Tsai MY, Gaziano JM. 2014. Plasma cis-vaccenic acid and risk of heart failure with antecedent coronary heart disease in male physicians. Clin. Nutr. 33, 478-482. https://doi.org/10.1016/j.clnu.2013.07.001 PMid:23880347 PMCid:PMC3851975

Elmastas M¸ Dermirtas I, Isildak O. 2006. Antioxidant Activity of S-Carvone Isolated from Spearmint (Mentha Spicata L. Fam Lamiaceae). J. Liq. Chromatogr. Relat. Technol. 29, 1465-1475. https://doi.org/10.1080/10826070600674893

Fatope MO, Marwah RG, Onifade AK, Ochei JE, Al Mahroqi YKS. 2006. C-13 NMR analysis and antifungal and insecticidal activities of Oman dill herb oil. Pharm. Biol. 44, 44-49. https://doi.org/10.1080/13880200500530716

Farzaei MH, Abbasabadi Z, Ardekani MRS, Rahimi R, Fatemeh F. 2013. Parsley: a review of ethnopharmacology, phytochemistry and biological activities. J. Tradit. Chin. Med. 33, 815-826. https://doi.org/10.1016/S0254-6272(14)60018-2

Galanakis CM, Tsatalas P, Charalambous Z, Galanakis IM. 2018. Polyphenols recovered from olive mill wastewater as natural preservatives in extra virgin olive oils and refined olive kernel oils. Environ. Technol. Innov. 10, 62-70. https://doi.org/10.1016/j.eti.2018.01.012

Girgis A, Lambert S, Johnson C, Waller A, Currow D. 2012. Physical, psychosocial, relationship, and economic burden of caring for people with cancer: a review. J. Oncol. Pract. 9, 197-202. https://doi.org/10.1200/JOP.2012.000690 PMid:23942921 PMCid:PMC3710169

He WP, Huang BK. 2011. Research progress in chemical constituents in dried fruits of Anethum graveolens and their pharmacological effects. Drugs Cl. 26, 457-460.

ISO. 1996. Animal and vegetable fats and oils-Determination of acid value and acidity: ISO 660. International Organisation for Standardisation.

ISO. 2001. Animal and vegetable fats and oils-Determination of peroxide value: ISO 3960. International Organisation for Standardisation.

Jana S, Shekhawat GS. 2010. Anethum graveolens: An Indian traditional medicinal herb and spice. Pharmacogn. Rev. 4, 179-184. https://doi.org/10.4103/0973-7847.70915 PMid:22228959 PMCid:PMC3249919

Kalinichenko SG, Matveeva NY. 2008. Morphological characteristics of apoptosis and its significance in neurogenesis. Neurosci. Behav. Physiol. 38, 333-344. https://doi.org/10.1007/s11055-008-0046-7 PMid:18401722

Lanky PS, Schilcher H, Phillipson JD, Loew D. 1993. Plants that lower cholesterol. Acta Hortic. 332, 131-136. https://doi.org/10.17660/ActaHortic.1993.332.17

Lopez P, Sanchez C, Batlle R, Nerin C. 2005. Solid- and vapor-phase antimicrobial activities of six essential oils: susceptibility of selected foodborne bacterial and fungal strains. J. Agric. Food Chem. 53, 6939-6946 https://doi.org/10.1021/jf050709v PMid:16104824

Mohammed FA, Elkady AI, Syed FQ, Mirza MB, Hakeem KR, Alkarim S. 2018. Anethum graveolens (dill)-A medicinal herb induces apoptosis and cell cycle arrest in HepG2 cell line. J. Ethnopharmacol. 219, 15-22. https://doi.org/10.1016/j.jep.2018.03.008 PMid:29530611

Mokbli S, Nehdi IA, Sbihi H, Tan CP, Al-Resayes SI, Rashid U. 2018. Yucca aloifolia seed oil: a new source of bioactive compounds. Waste Biomass. Valor. 9, 1087-1093. https://doi.org/10.1007/s12649-017-9892-2

Nehdi IA, Sbihi H, Tan CP, Al-Resayes SI. 2013. Evaluation and characterization of Citrullus colocynthis (L.) Schrad seed oil: Comparison with Helianthus annuus (sunflower) seed oil. Food Chem. 136, 348-353. https://doi.org/10.1016/j.foodchem.2012.09.009 PMid:23122069

Nehdi IA, Mokbli S, Sbihi H, Tan CP, Al-Resayes SI. 2014a. Chamaerops humilis L. var. argentea Andre Date Palm Seed Oil: A Potential Dietetic Plant Product. J. Food Sci. 79, C534-C539. https://doi.org/10.1111/1750-3841.12420 PMid:24666023

Nehdi IA, Sbihi H, Tan CP, Al-Resayes SI. 2014b. Leucaena leucocephala (Lam.) de Wit seed oil: Characterization and uses. Ind. Crops Prod. 52, 582-587. https://doi.org/10.1016/j.indcrop.2013.11.021

Nehdi IA, Sbihi H, Tan CP, Rashid U, Al-Resayes SI. 2018. Chemical Composition of Date Palm (Phoenix dactylifera L.) Seed Oil from Six Saudi Arabian Cultivars. J. Food Sci. 83, 624-630. https://doi.org/10.1111/1750-3841.14033 PMid:29377104

Prakash OM, Kumar A, Kumar P. 2013. Anticancer potential of plants and natural products: a review. Am. J. Pharmacol. Sci. 1, 104-115. https://doi.org/10.12691/ajps-1-6-1

Ruiz-Canela M, Martínez-González MA. 2011. Olive oil in the primary prevention of cardiovascular disease. Maturitas 68, 245-250. https://doi.org/10.1016/j.maturitas.2010.12.002 PMid:21216542

Rajeshwari T, Raja B. 2015. Antioxidant and Free radical Scavenging Effect of d-carvone in Hypertensive Rats. In Vivo and In Vitro study. Int. Let. Nat. Sci. 35, 6-12. https://doi.org/10.18052/www.scipress.com/ILNS.35.6

Safhi MM, Sivakumar SM, Jabeen A, Zakir F, Islam F, Anwer T, Bagul US, Elmobark ME, Khan G, Siddiqui R, Hussien A, Alam MF. 2017. Nanoparticle System for Anticancer Drug Delivery: Targeting to Overcome Multidrug Resistance. In: Grumezescu AM, editor, Multifunctional Systems for Combined Delivery, Biosensing and Diagnostics. Elsevier, pp. 159-169. https://doi.org/10.1016/B978-0-323-52725-5.00008-3

Schwarz A, Bhardwaj R, Aragane Y, Mahnke K, Riemann H, Metze D, Schwarz T. 1995. Ultraviolet-B-induced apoptosis of keratinocytes: Evidence for partial involvement of tumor necrosis factor-alpha in the formation of sunburn cells. J. Invest. Derm.104, 922-927. https://doi.org/10.1111/1523-1747.ep12606202 PMid:7769259

Shyu YS, Lin JT, Chang YT, Chiang CJ, Yang DJ. 2009. Evaluation of antioxidant ability of ethanolic extract from dill (Anethum graveolens L.) flower. Food Chem. 115, 515-521. https://doi.org/10.1016/j.foodchem.2008.12.039

Siger A, Dwiecki K, Borzyszkowski W, Turski M, Rudzinska M, Nogala-Kałucka M. 2017. Physicochemical characteristics of the cold-pressed oil obtained from seeds of Fagus sylvatica L. Food Chem. 225, 239-245. https://doi.org/10.1016/j.foodchem.2017.01.022 PMid:28193421

Stefano V di, Pitonzo R, Schillaci D. 2011. Antimicrobial and antiproliferative activity of Athamanta sicula L. (Apiaceae). Pharmacogn. Mag. 7, 31-34. https://doi.org/10.4103/0973-1296.75893 PMid:21472076 PMCid:PMC3065153

Stojanov N. 1973. Dill, Anethum graveolens L. In: Stojanov N, editor, Our Medicinal Plants. Sofia, Bulgaria: Nauka Izkustvo Press; pp. 110-113.

Taghvaei M, Jafari SM, Mahoonak AS, Nikoo AM, Rahmanian N, Hajitabar J, Meshginfar N. 2014. The effect of natural antioxidants extracted from plant and animal resources on the oxidative stability of soybean oil. LWT-Food Sci. Technol. 56, 124-130. https://doi.org/10.1016/j.lwt.2013.11.009

Tebbe B, Mansmann U, Wollina U, Auer-Grumbach P, Licht- Mbalyohere A, Arensmeier M, Orfanos CE. 1997. Markers in cutaneous lupus erythematosus indicating systemic involvement: A multicenter study on 296 patients. Acta Derm. Venereol. 77, 305-308.

Yang Y, Huang CY, Peng SS, Li J. 1996. Carotenoid analysis of several dark green leafy vegetables associated with a lower risk of cancers. Biomed. Environ. Sci. 9, 386-392.

Zhang H, Chen F, Wang X, Yao HY. 2006. Evaluation of antioxidant activity of parsley (Petroselinum crispum) essential oil and identification of its antioxidant constituents. Food Res. Int. 39, 833-839. https://doi.org/10.1016/j.foodres.2006.03.007