Development and Certification of Formononetin Reference Material for Quality Control of Functional Foods and Botanical Supplements

Page: [553 - 559] Pages: 7

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Abstract

Background: Formononetin is a common soy isoflavonoid that can be found abundantly in many natural plants. Previous studies have shown that formononetin possesses a variety of activities which can be applied for various medicinal purposes. Certified Reference Materials (CRMs) play a fundamental role in the food, traditional medicine and dietary supplement fields, and can be used for method validation, uncertainty estimation, as well as quality control.

Methods: The purity of formononetin was determined by Differential Scanning Calorimetry (DSC), Coulometric Titration (CT) and Mass Balance (MB) methods.

Results: This paper reports the sample preparation methodology, homogeneity and stability studies, value assignment, and uncertainty estimation of a new certified reference material of formononetin. DSC, CT and MB methods proved to be sufficiently reliable and accurate for the certification purpose. The purity of the formononetin CRM was therefore found to be 99.40% ± 0.24 % (k = 2) based on the combined value assignments and the expanded uncertainty.

Conclusion: This CRM will be a reliable standard for the validation of the analytical methods and for quality assurance/quality control of formononetin and formononetin-related traditional herbs, food products, dietary supplements and pharmaceutical formulations.

Keywords: Isoflavonoid, purity determination, mass balance method, differential scanning calorimetry, coulometric titration, formononetin.

Graphical Abstract

[1]
Zhang, J.; Du, F.; Peng, B.; Lu, R.; Gao, H.; Zhou, Z. Structure, electronic properties, and radical scavenging mechanisms of daidzein, genistein, formononetin, and biochanin A: A density functional study. J. Mol. Struct-THEOCH., 2010, 955(1-3), 1-6.
[2]
Zielinska, A.; Paradowska, K.; Jakowski, J.; Wawer, I. 13C CP MAS NMR and GIAO-CHF/DFT calculations of flavonoids: Morin, formononetin, tricin, genistein, formononetin and 3,7-dihydroxyflavone. J. Mol. Struct., 2008, 873(1-3), 109-116.
[3]
Wu, J.H.; Li, Q.; Wu, M.Y.; Guo, D.J.; Chen, H.L.; Chen, S.L.; Seto, S.W.; Au, A.L.; Poon, C.C.; Leung, G.P.; Lee, S.M.; Kwan, Y.W.; Chan, S.W. Formononetin, an isoflavone, relaxes rat isolated aorta through endothelium-dependent and endotheliumin dependent pathways. J. Nutr. Biochem., 2009, 21(7), 613-620.
[4]
Maurya, R.; Yadav, D.K.; Singh, G.; Bhargavan, B.; Narayana, M.P.S.; Sahai, M.; Singh, M.M. Osteogenic activity of constituents from Butea monosperma. Bioorg. Med. Chem. Lett., 2009, 19(3), 610-613.
[5]
Sun, T.; Wang, J.; Huang, L.H.; Cao, Y.X. Antihypertensive effect of formononetin through regulating the expressions of eNOS,5-HT2A/1B receptors and a1-adrenoceptors in spontaneously rat arteries. Eur. J. Pharmacol., 2013, 699(1-3), 241-249.
[6]
Huang, J.; Xie, M.; Gao, P.; Ye, Y.; Liu, Y.; Zhao, Y.; Luo, W.; Ling, Z.; Cao, Y.; Zhang, S.; Gao, F.; Tang, W. Antiproliferative effects of formononetin on human colorectal cancer via suppressing cell growth in vitro and in vivo. Process Biochem., 2015, 50(6), 912-917.
[7]
Li, Z.; Dong, X.; Zhang, J.; Zeng, G.; Zhao, H.; Liu, Y.; Qiu, R.; Mo, L.; Ye, L. Formononetin protects TBI rats against neurological lesions and the underlying mechanism. J. Neurol. Sci., 2014, 338(1-2), 112-117.
[8]
Liang, K.; Ye, Y.; Wang, Y.; Zhang, J.; Li, C. Formononetin mediates neuroprotection against cerebral ischemia/reperfusion in rats via downregulation of the Bax/Bcl-2 ratio and upregulation PI3K/Akt signaling pathway. J. Neurol. Sci., 2014, 344(1-2), 100-104.
[9]
Huh, J.E.; Nam, D.W.; Baek, Y.H.; Kang, J.W.; Park, D.S.; Choi, D.Y.; Lee, J.D. Formononetin accelerates wound repair by the regulation of early growth response factor-1 transcription factor through the phosphorylation of the ERK and p38 MAPK pathways. Int. Immunopharmacol., 2011, 11(1), 46-54.
[10]
Lo, Y.L.; Wang, W. Formononetin potentiates epirubicin-induced apoptosis via ROS production in HeLa cells in vitro. Chem. Biol. Interact., 2013, 205(3), 188-197.
[11]
11 Chen, C.Y.; Zu, Y.G.; Fu, Y.J.; Luo, M.; Zhao, C.J.; Wang, W.; Zhao, B.S.; Li, J.; Efferth, T. Preparation and antioxidant activity of Radix Astragali residues, extracts rich in calycosin and formononetin. Biochem. Eng. J., 2011, 56(1-2), 84-93.
[12]
Mu, H.; Bai, Y.H.; Wang, S.T.; Zhu, Z.M.; Zhang, Y.W. Research on antioxidant effects and estrogenic effect of formononetin from Trifolium pratense (red clover). Phytomedicine, 2009, 16(4), 314-319.
[13]
Ma, W.; Nomura, M.; Takahashi-Nishioka, T.; Kobayashi, S. Combined effects of fangchinoline from Stephania tetrandra Radix and formononetin and calycosin from Astragalus membranaceus Radix on hyperglycemia and hypoinsulinemia in streptozotocin-diabetic mice. Biol. Pharm. Bull., 2007, 30(11), 2079-2083.
[14]
Wang, Y.; Zhu, Y.; Gao, L.; Yin, H.; Xie, Z.; Wang, D.; Zhu, Z.; Han, X. Formononetin Attenuates IL-1β-Induced Apoptosis and NF-κB Activation in INS-1 Cells. Molecules, 2012, 17(9), 10052-10064.
[15]
Mutai, P.; Pavadai, E.; Wiid, I.; Ngwane, A.; Baker, B.; Chibale, K. Synthesis, antimycobacterial evaluation and pharmacophore modeling of analogues of the natural product formononetin. Bioorg. Med. Chem. Lett., 2015, 25(12), 2510-2513.
[16]
Auyeung, K.K.; Law, P.C.; Ko, J.K. Novel anti-angiogenic effects of formononetin in human colon cancer cells and tumor xenograft. Oncol. Rep., 2012, 28(6), 2188-2194.
[17]
ISO Guide 34. General requirements for the competence of reference material producers. International Organization for Standardization: Geneva, 2009.
[18]
Espinoza, M.; Olea-Azar, C.; Massiff, G.; Villa, A.E. Development of a reference material for copper and iron in wine. J. Food Compos. Anal., 2008, 21(8), 684-688.
[19]
Sin, D.W.M.; Chan, P.K.; Cheung, S.T.C.; Wong, Y.L.; Wong, S.K.; Mok, C.S.; Wong, Y.C. Development of a candidate certified reference material of cypermethrin in green tea. Anal. Chim. Acta, 2012, 721, 110-114.
[20]
ISO Guide 35. Reference materials–General and statistical principles for certification, International Organization for Standardization: Geneva, 2006.
[21]
Bruni, G.; Berbenni, V.; Milanese, C.; Girella, A.; Cardini, A.; Lanfranconi, S.; Marini, A. Determination of the nateglinide polymorphic purity through DSC. J. Pharmaceut. Biomed., 2011, 54(5), 1196-1199.
[22]
Gong, N.B.; Wang, X.Y.; Zhang, B.X.; Gao, Z.L.; Du, G.H.; Lv, Y. Characterization and uncertainty evaluation of a new certified reference material of Baicalein. J. Pharmaceut. Biomed., 2014, 89, 106-110.
[23]
Gong, N.B.; Liu, S.C.; Xu, W.; Shi, Y.Q.; Du, G.H.; Lu, Y. Purity assessment of luteolin reference material candidates by coulometric titration method. Anal. Methods-UK, 2013, 5, 784-788.
[24]
Tan, R.H.; An, X.H. Isolation and synthesis of formnonetin. Chem. Res. Appl., 2009, 21(5), 764-765.
[25]
Pelter, A.; Ward, R.S.; Whalley, J.L. A Facile Synthesis of 2-Substituted isoflavones for immunoassay: Assembly of the isoflavonoid skeleton by means of a novel cyclisation reaction. Synthesis-Stuttgart., 1998, 1998(12), 1793-1802.