Changes in the sterol compositions of milk thistle oil (Silybium marianum L.) during seed maturation


  • S. Harrabi Biochemistry Department, Faculty of Medicine Tunis, University of Tunis El-Manar
  • S. Curtis Chemistry Department, University of Ottawa
  • F. Hayet Biochemistry Department, Faculty of Medicine Tunis, University of Tunis El-Manar
  • P. M. Mayer Chemistry Department, University of Ottawa



Maturation, Milk thistle seeds, Oil, Sterols changes


In this study, the total lipid content and sterol compositions were determined during the development of milk thistle seeds. The oil content increased to a maximum value of 36±1.7% and then declined to reach a value of 30.5±0.9% at full maturity. The sterol content of milk thistle seeds was affected by the ripening degree of the seeds. At the early stages of seed maturation, Δ7-stigmastenol was the most abundant sterol followed by β-sitosterol. However, at full maturity, β-sitosterol was the most predominant sterol (46.50±0.8%). As the seed developed, campesterol and stigmasterol amounts increased, while Δ7-avenasterol content decreased. It can be concluded that milk thistle seed oil has a characteristic sterol pattern comparable to the ones elucidated for olive oil and corn oil. The extracted oil from milk thistle seeds is rich in phytosterols and could be used in food preparation and human nutrition.


Download data is not yet available.


Alonso-Salces RM, Héberger K, Holland MV, Moreno-Rojas JM, Mariani C, Bellan G, Reniero F, Guillou C. 2010. Multivariate analysis of NMR fingerprint of the unsaponifiable fraction of virgin olive oils for authentication purposes. Food Chem. 118, 956-965.

Awad AB, Chinnam M, Fink CS, Bradford PG. 2007. É¿-Sitosterol activates Fas signaling in human breast cancer cells. Phytomedicine, 14, 747-754. PMid:17350814

Azadmard-Damirchi S, Dutta PC. 2006. Novel solid-phase extraction method to separate 4-desmethyl, 4-monomethyl-, and 4,4-dimethylsterols in vegetable oils. J. Chromatogr. A 1108, 183-187. PMid:16445919

Azadmard-Damirchi S, Savage GP, Dutta PC. 2005. Sterol fractions in hazelnut and virgin olive oils and 4, 4-dimethylsterols as possible markers for detection of adulteration of virgin olive oil. J. Am. Oil Chem. Soc. 82, 717-725.

Blekas G, Boskou D. 1999. Phtosterols and stability of frying oils. In: Boskou D, Elmadfa I (Eds.) Frying of Food, VA: Technomic Publishing Co., Lancaster, Pennsylvania, pp. 205-222.

Benveniste P. 2002. The Arabidopsis Book. American Society of Plant Biologists. Rockville, MD. publications.

Berges RR, Windeler J, Trampisch HJ, Senge T. 1995. Randomised, placebo-controlled, double-blind clinical trial of beta-sitosterol in patients with benign prostatic hyperplasia. Betasitosterol Study Group. Lancet, 345, 1529-32.

Canabate-Díaz B, Segura Carretero A, Fernández-Gutiérrez A, Belmonte Vega A, Garrido Frenich A, Martínez Vidal JL, Duran Martos J. 2007. Separation and determination of sterols in olive oil by HPLC-MS. Food Chem. 102, 593-598.

Cercaci L, Passalacqua G, Poerio A, Rodriguez-Estrada MT, Lercker G. 2007. Composition of total sterols (4-desmethyl -sterols) in extravirgin olive oilsobtained with different extraction technologies and their influence on the oil oxidativestability. Food Chem. 102, 66-76.

Dabbour IR, Al-Ismail KM, Takruri HR, Azzeh FS. 2014. Chemical Characteristics and Antioxidant Content Properties of Cold Pressed Seed Oil of Wild Milk Thistle Plant Grown in Jordan. Pak. J. Nutr. 13, 67-78.

El-Mallah MH, El-Shami SM, Hassanein MM. 2003. Detailed studies on some lipids of silybummarianum (L) seed oil. Grasas Aceites, 54, 397-402.

Engelberth AS, Carrier DJ, Clausen EC. 2008. Separation of silymarins from milk thistle (Silybummarianum L.) extracted with pressurized hot water using fast centrifugal partition chromatography. J. Liq. Chromatogr. Relat. Technol. 31, 3001-3011.

Fadhil AB, Ahmed KM, Dheyab MM. 2012. Silybummarianum L. seed oil: A novel feedstock for biodiesel production. Arabian J. Chem.

Fathi-Achachlouei B, Azadmard-Damirchi S. 2009. Milk Thistle Seed Oil Constituents from Different Varieties Grown in Iran. J. Am. Oil Chem. Soc. 86, 643-649.

Gopala Krishna AG, Prashanth PA, Pragasam A, Raghavendra KV, Matoon S. 2003. Unsaponifiable matter and oxidative stability of commercially produced Indian rice bran oils. J. Food Lipids, 10, 329-340.

Grandmougin A, Bouvier-Nave P, Ullman P, Benveniste P, Hartmann MA. 1989. Cyclopropyl sterol and phospholipids composition of membrane fractions from maize roots treated withfenpropimorth. Plant Physiol. 90, 591-597. PMID: 16666813. PMid:16666813 PMCid:PMC1061766

Harrabi S, Sakouhi F, St-Amand A, Boukhchina S, Kallel H, Mayer PM. 2007. Accumulation of phytoterols, triterpene alcohols and phytostanols in developing zea mays L. kernels. J. Plant Sci. 2, 260-272.

Jones PJ, Raeini-Sarjaz M, Ntanios FY, Vanstone CA, Feng JY, Parsons WE. 2000. Modulation of plasma lipid levels and cholesterol kinetics by phytosterol versus phytostanol esters. J. Lipid Research, 41, 697-705. PMid:10787430

Karkanis A, Bilalis D, Efthimiadou A, 2011. Cultivation of milk thistle (Silybummarianum L. Gaertn.), a medicinal weed. Ind. Crops Prod. 34, 825-830.

Malekzadeh M, Mirmazloum SI, Anguorani HR, Mortazavi SN, Panahi M. 2011. The physicochemical properties and oil constituents of milk thistle (Silybummarianum Gaertn. cv. Budakalászi) under drought stress. J. Med. Plant. Res. 5, 1485-1488.

Mezghache M, Henchiri C, Martine L, Berdeaux O, Aouf N, Juaneda P. 2010. Etude de la composition stérolique de trois huiles d'olive issues des variétés Guasto, Rougette et Blanquette plantés dans l'est algérien. O.C.L. 17, 337-344.

Miettinen TA, Puska P, Gylling H, Vanhanen H, Vartiainen E. 1995. Reduction of serum cholesterol with sitostanol-ester margarine in a mildly hypercholesterolemic population. N. Engl. J. Med. 333, 1308-1312. PMid:7566021

Ma_ecka M. 2002. Antioxidant properties of the unsaponifiable matter isolated from tomato seeds, oat grains and wheat germ oil. Food Chem. 79, 327-330.

Mohamed HAM, Awatif II. 1998. The use of sesame oil unsaponifiable matter as a natural antioxidant. Food Chem. 62, 269-276.

LagardaMJ, García-Llatas G, Farré R. 2006. Analysis of phytosterols in foods. J. Pharmaceut. Biomed. Anal. 41, 1486-1496. PMid:16621410

Li TSC, Beveridge THJ, Drover JCG. 2007. Phytosterol content of seabuckthorn (Hippophaerhamnoides L.) seed oil: Extraction and identification. Food Chem. 101, 1633-1639.

Ntanios F. 2001. Plant sterol-ester-enriched spreads as an example of a new functional food. Eur. J. Lipid Sci. Technol. 103, 102-106.<102::AID-EJLT102>3.0.CO;2-A

Ostlund RE Jr, Racette SB, Okeke A, Stenson WF. 2002. Phytosterols that are naturally present in commercial corn oil significantly reduce cholesterol absorption in humans. Am. J. Clin. Nutr. 75, 1000-1004. PMid:12036805

Phillips KM, Ruggio DM, Toivo JI, Swank MA, Simpkins AH. 2002. Free and esterified sterol composition of edible oils and fats. J. Food Compos. Anal. 15, 123-142.

Ronco A, De Stefani E, Boffetta P, Deneo-Pellegrini H, Mendilaharsu M, Leborgne F. 1999. Vegetables, fruits, and related nutrients and risk of breast cancer: a case-control study in Uruguay. Nutr. Cancer, 35, 111-119. PMid:10693163

Sánchez Casas J, Bueno EO, García AMM, Cano MM. 2004. Sterol and erythrodiol+uvaol content of virgin olive oils from cultivars of Extremadura (Spain). Food Chem. 87, 225-230.

Stefanoudaki E, Chartzoulakis K, Koutsaftakis A, Kotsifaki F. 2001. Effect of drought stress on qualitative characteristics of olive oil of cvKoroneiki. Grasas Aceites, 52, 202-206.

Voelker T, Kinney AJ. 2001. Variations in the biosynthesis of seed-storage lipids. Annu. Rev. Plant Mol. Biol. 52, 335-361. PMid:11337402

Wallace SN, Carrier DJ, Clausen EC. 2005. Batch solvent extraction of flavonoligans from milk thistle (Silybummarianum L. Gaertner). Phytochem. Anal. 16, 7-16. PMid:15688950

Weihrauch JL, Gardner JM. 1978. Sterol content of foods of plant origin. J. Am. Diet. Assoc. 73, 39-47. PMid:659760

Williamson E. 1998. The antioxidant activity of ɢ5-avenasterol. PhD Thesis, University of Reading, Reading, UK.

Yoshida Y, Niki E. 2003. Antioxidant effects of phytosterol and its components. J. Nutr. Sci. Vitaminol. 49, 277-280.

Zheljazkov VD, Zhalnov I, Nedkov NK. 2006. Herbicides for weed control in blessed thistle (Silybummarianum). Weed Technol. 20, 1030-1034.



How to Cite

Harrabi S, Curtis S, Hayet F, Mayer PM. Changes in the sterol compositions of milk thistle oil (Silybium marianum L.) during seed maturation. grasasaceites [Internet]. 2016Mar.31 [cited 2022Nov.29];67(1):e123. Available from: