year 21, Issue 81 (3-2022)                   J. Med. Plants 2022, 21(81): 1-11 | Back to browse issues page


XML Persian Abstract Print


Download citation:
BibTeX | RIS | EndNote | Medlars | ProCite | Reference Manager | RefWorks
Send citation to:

Tavakoli S, Khalighi-Sigaroodi F, Hagiaghaee R, Yaghoobi M, Ghafarzadegan R. Purification, identification, and standardization of silybin A & B composition from Silybum marianum (L.) Gaertn.. J. Med. Plants. 2022; 21 (81) :1-11
URL: http://jmp.ir/article-1-3113-en.html
1- Medicinal Plants Research Center, Institute of Medicinal Plants, ACECR, Karaj, Iran
2- Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, Tehran, Iran
3- Medicinal Plants Research Center, Institute of Medicinal Plants, ACECR, Karaj, Iran , Ghafarzadegan@imp.ac.ir
Abstract:   (472 Views)
Background: Silybum marianum (L.) Gaertn. (Milk thistle) is a perennial herb with medicinal properties. The seeds of these plants contain silymarin compounds with flavonolignan structure and antioxidant, anti-inflammatory and hepatoprotective effects. The major bioactive constituent of S. marianum is silybin A and B. It is used in the treatment of various liver conditions and exhibits high anti-tumor promoting activity. Objective: The purpose of this study was to purify, identify, and standardize of silybin A and B from the seeds extract of Silybum marianum. Methods: At first, the milk thistle seeds were defatted with hexane and then extracted with methanol as solvent. Isolation and further purification of silybin A and B was carried out by column chromatography using Diaion HP-20 resin, silica gel and Sephadex LH-20 as stationary phase, respectively. 1H-NMR and 13C-NMR techniques were used to identify these compounds. Finally, the HPLC method has been used to standardize. Results: 1H-NMR and 13C-NMR techniques characterized the structure of silybin A and B extracted from Silybum marianum L. and standardization and determination of their purity was performed using HPLC. Conclusion: Our proposed system presented significant advantages in increasing efficiency and reducing cost, and the diastereoisomers of silybin A and silybin B in silymarin were successfully isolated with high purities.
Full-Text [PDF 692 kb]   (329 Downloads)    
Type of Study: Research | Subject: Pharmacognosy & Pharmaceutics
Received: 2021/05/21 | Accepted: 2021/11/20 | Published: 2022/03/1

References
1. Rainone F. Milk thistle. Am. Fam. Physician. 2005; 72 (7): 1285-1288.
2. Wianowska D and Gil M. Silymarin Extraction From Silybum marianum L. Gaertner. In: Water Extraction of Bioactive Compounds: From Plants to Drug Development. Vol: Elsevier; 2017: 385-397. [DOI:10.1016/B978-0-12-809380-1.00015-2]
3. Abenavoli L, Capasso R, Milic N and Capasso F. Milk thistle in liver diseases: past, present, future. Phytother. Res. 2010; 24 (10): 1423-1432. [DOI:10.1002/ptr.3207]
4. Hackett ES, Mama KR, Twedt DC and Gustafson DL. Pharmacokinetics and safety of silibinin in horses. Am. J. Vet. Res. 2013; 74 (10): 1327-1332. [DOI:10.2460/ajvr.74.10.1327]
5. Hutchinson C, Bomford A and Geissler CA. The iron-chelating potential of silybin in patients with hereditary haemochromatosis. European J. Clinical Nutrition 2010; 64 (10): 1239-1241. [DOI:10.1038/ejcn.2010.136]
6. Pietrangelo A, Borella F, Casalgrandi G, Montosi G, Ceccarelli D, Gallesi D, Giovannini F, Gasparetto A and Masini A. Antioxidant activity of silybin in vivo during long-term iron overload in rats. Gastroenterol. 1995; 109 (6): 1941-1949. [DOI:10.1016/0016-5085(95)90762-9]
7. Federico A, Dallio M and Loguercio C. Silymarin/Silybin and Chronic Liver Disease: A Marriage of Many Years. Molecules 2017; 22 (2). [DOI:10.3390/molecules22020191]
8. Azadpour M, Farajollahi MM, Varzi AM, Hashemzadeh P, Mahmoudvand H and Barati M. Extraction, chemical composition, antioxidant property, and in-vitro an-ticancer activity of silymarin from Silybum marianum on kb and a549 cell lines. Curr. Drug Discov. Technol. 2021; 18 (4): 511-517. [DOI:10.2174/1570163817666200827111127]
9. Pashaei-Asl F, Pashaei-Asl R, Khodadadi K, Akbarzadeh A, Ebrahimie E and Pashaiasl M. Enhancement of anticancer activity by silibinin and paclitaxel combination on the ovarian cancer. Artif. Cells Nanomed. Biotechnol. 2018; 46 (7): 1483-1487. [DOI:10.1080/21691401.2017.1374281]
10. Patel AR and Vavia PR. Preparation and in vivo evaluation of SMEDDS (self-microemulsifying drug delivery system) containing fenofibrate. Aaps. J. 2007; 9 (3): E344-352. [DOI:10.1208/aapsj0903041]
11. Gorgisen G, Ozkol H, Tuluce Y, Arslan A, Ecer Y, Keskin S, Kaya Z and Ragbetli MC. Silibinin and ellagic acid increase the expression of insulin receptor substrate 1 protein in ultraviolet irradiated rat skin. Biotech. Histochem. 2020; 95 (8): 641-646. [DOI:10.1080/10520295.2020.1753238]
12. MacDonald-Ramos K, Michán L, Martínez-Ibarra A and Cerbón M. Silymarin is an ally against insulin resistance: A review. Ann. Hepatol. 2021; 23. [DOI:10.1016/j.aohep.2020.08.072]
13. Poruba M, Matušková Z, Kazdová L, Oliyarnyk O, Malínská H, Tozzi di Angelo I and Večeřa R. Positive effects of different drug forms of silybin in the treatment of metabolic syndrome. Physiol. Res. 2015; 64: S507-S512. [DOI:10.33549/physiolres.933235]
14. Wang F, Li Z, Song T, Jia Y, Qi L, Ren L and Chen S. Proteomics study on the effect of silybin on cardiomyopathy in obese mice. Sci. Rep. 2021; 11 (1). [DOI:10.1038/s41598-021-86717-x]
15. Yao J, Zhi M, Gao X, Hu P, Li C and Yang X. Effect and the probable mechanisms of silibinin in regulating insulin resistance in the liver of rats with non-alcoholic fatty liver. Braz. J. Med. Biol. Res. 2013; 46 (3): 270-277. [DOI:10.1590/1414-431X20122551]
16. Liu K, Zhou S, Liu J, Wang Y, Zhu F and Liu M. Silibinin attenuates high-fat diet-induced renal fibrosis of diabetic nephropathy. Drug Des. Dev. Ther. 2019; 13: 3117-3126. [DOI:10.2147/DDDT.S209981]
17. Christodoulou E, Kechagia IA, Tzimas S, Balafas E, Kostomitsopoulos N, Archontaki H, Dokoumetzidis A and Valsami G. Serum and tissue pharmacokinetics of silibinin after per os and i.v. administration to mice as a HP-β-CD lyophilized product. Int. J. Pharm. 2015; 493 (1-2): 366-373. [DOI:10.1016/j.ijpharm.2015.07.060]
18. Wu S and Chappell J. Metabolic engineering of natural products in plants; tools of the trade and challenges for the future. Curr. Opin. Biotechnol. 2008; 19 (2): 145-152. [DOI:10.1016/j.copbio.2008.02.007]
19. British Pharmacopoeia Commission. British Pharmacopoeia 2017. London: TSO; 2017.
20. Biedermann D, Hurtová M, Benada O, Valentová K, Biedermannová L and Křen V. Continuous diastereomeric kinetic resolution-silybins A and B. Catalysts 2021; 11 (9). [DOI:10.3390/catal11091106]
21. Kim N-C, Graf TN, Sparacino CM, Wani MC and Wall ME. Complete isolation and characterization of silybins and isosilybins from milk thistle (Silybum marianum). Organic & Biomolecular Chem. 2003; 1 (10): 1684-1689. [DOI:10.1039/b300099k]
22. Davis-Searles PR, Nakanishi Y, Kim NC, Graf TN, Oberlies NH, Wani MC, Wall ME, Agarwal R and Kroll DJ. Milk thistle and prostate cancer: differential effects of pure flavonolignans from Silybum marianum on antiproliferative end points in human prostate carcinoma cells. Cancer Res. 2005; 65 (10): 4448-4457. [DOI:10.1158/0008-5472.CAN-04-4662]
23. Hoh CS, Boocock DJ, Marczylo TH, Brown VA, Cai H, Steward WP, Berry DP and Gescher AJ. Quantitation of silibinin, a putative cancer chemopreventive agent derived from milk thistle (Silybum marianum), in human plasma by high-performance liquid chromatography and identification of possible metabolites. J. Agric. Food Chem. 2007; 55 (7): 2532-2535. [DOI:10.1021/jf063156c]
24. Lee JI, Narayan M and Barrett JS. Analysis and comparison of active constituents in commercial standardized silymarin extracts by liquid chromatography-electrospray ionization mass spectrometry. J. Chromatogr B Analyt Technol Biomed Life Sci. 2007; 845 (1): 95-103. [DOI:10.1016/j.jchromb.2006.07.063]
25. Wen Z, Dumas TE, Schrieber SJ, Hawke RL, Fried MW and Smith PC. Pharmacokinetics and metabolic profile of free, conjugated, and total silymarin flavonolignans in human plasma after oral administration of milk thistle extract. Drug Metab Dispos. 2008; 36 (1): 65-72. [DOI:10.1124/dmd.107.017566]
26. Smith WA, Lauren DR, Burgess EJ, Perry NB and Martin RJ. A silychristin isomer and variation of flavonolignan levels in milk thistle (Silybum marianum) fruits. Planta Med. 2005; 71 (9): 877-880. [DOI:10.1055/s-2005-864187]

Add your comments about this article : Your username or Email:
CAPTCHA

Send email to the article author


Rights and permissions
Creative Commons License This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.

© 2022 CC BY-NC 4.0 | Journal of Medicinal Plants

Designed & Developed by : Yektaweb