Isoflavone-aglycone fraction from <i>Glycine max</i>: a promising raw material for isoflavone-based pharmaceutical or nutraceutical products

Yatsu, Francini K.J.; Koester, Letícia S.; Bassani, Valquiria L.

doi:10.1016/j.bjp.2015.12.004

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Original Article • Rev. bras. farmacogn. 26 (2) • Mar-Apr 2016 • https://doi.org/10.1016/j.bjp.2015.12.004 copy

Isoflavone-aglycone fraction from Glycine max: a promising raw material for isoflavone-based pharmaceutical or nutraceutical products

Authorship SCIMAGO INSTITUTIONS RANKINGS

ABSTRACT

The present work was designed to obtain a fraction containing high concentration of isoflavone-aglycones from Glycine max (L.) Merr., Fabaceae, named isoflavone enriched-fraction, from a dry extract containing isoflavones-glycosides. A simple and low cost method was proposed: extraction of isoflavone glycosides from the G. max dry extract with a proper solvent, hydrolysis of the glycosides, recovery of the aglycones, and purification of the fraction containing high isoflavone-aglycones concentration. All the extraction and purification parameters were optimized based on the isoflavones yields, which were analyzed by liquid chromatography and expressed as total isoflavone aglycones. The optimization of the process conditions was accomplished using the classical one-variable-at-a-time method. The identity and purity of the isoflavones contained in this enriched fraction were determined by LC/UV/ESI/MS analysis, Fourier transformed-infrared spectroscopy, and ¹H and ¹³C nuclear magnetic resonance spectroscopy. The physicochemical properties of the isoflavone enriched-fraction were evaluated by scanning electron microscopy, X-ray diffraction and differential scanning calorimetry. The moisture content, particle size, equilibrium solubility and thermal and photostability were also determined. The high isoflavone-aglycone content (daidzein, 489.35 mg/g; glycitein, 251.02 mg/g and genistein, 158.96 mg/g) as well as the high purity obtained (90% of total isoflavones) make this fraction a promising novel raw material for the production of isoflavone-aglycones based pharmaceuticals or functional foods.

Keywords:
Isoflavone-aglycone fraction; Daidzein; Flavonoids; Genistein; Glycitein; Soy

Isoflavones	Concentration (mg/g) (RSD)
	Glycine max dry extract	Extractive solution^* * The content (mg/g) was calculated based on the amount of isoflavones in the Glycine max dry extract.	Hydrolyzed extract^* * The content (mg/g) was calculated based on the amount of isoflavones in the Glycine max dry extract.	Crystallized product^* * The content (mg/g) was calculated based on the amount of isoflavones in the Glycine max dry extract.
Daidzein	60.77 ± 4.24	62.80 ± 1.72	53.47 ± 0.38	27.53 ± 0.47
Glycitein	19.80 ± 1.38	20.46 ± 0.56	20.97 ± 0.38	10.80 ± 0.20
Genistein	63.79 ± 3.84	60.79 ± 1.97	55.90 ± 0.70	41.27 ± 0.19
Total	144.36 ± 9.46	144.05 ± 4.25	130.34 ± 1.08	79.60 ± 1.04

Fractions	Isoflavones concentration (mg/g) (RSD)^* * The content (mg/g) was calculated based on the amount of isoflavones in the crystals obtained in the fractional recrystallization experiment performed in triplicate; significant statistical differences were determined by Tukey's test (p < 0.05); differences between the concentrations were represented by different letters (a, b, c).
	Daidzein	Glycitein	Genistein	Total
X1	124.82 ± 3.12	727.13 ± 5.23	65.75 ± 2.07	917.70 ± 9.18^a
X2	489.35 ± 5.30	251.02 ± 3.33	158.96 ± 3.06	899.33 ± 9.26^a
X3	338.70 ± 9.84	257.57 ± 3.40	205.86 ± 3.54	802.13 ± 13.23^b
X4	522.32 ± 5.07	71.86 ± 2.03	260.36 ± 4.14	854.54 ± 8.84^c

Isoflavones	Purified fraction (µg/ml) (RSD)	Standards (µg/ml) (RSD)
Daidzein	12.54 ± 0.05	1.47 ± 0.08
Glycitein	11.32 ± 1.97	0.59 ± 0.12
Genistein	20.69 ± 1.29	5.77 ± 0.24

K (mg/day)
Stress conditions	NaOH			H₂O₂
	Daidzein	Glycitein	Genistein	Daidzein	Glycitein	Genistein
60 °C	-0.53^b b First-order kinetic. ^,^c c mg/h.	-0.09^b b First-order kinetic. ^,^c c mg/h.	-0.15^b b First-order kinetic. ^,^c c mg/h.	-0.37^b b First-order kinetic.	-1.26^a a Zero-order kinetic.	-0.53^b b First-order kinetic.
UV/24 °C	-0.75^b b First-order kinetic.	-0.78^a a Zero-order kinetic.	-0.37^b b First-order kinetic.	-0.74^b b First-order kinetic.	-0.69^b b First-order kinetic.	-0.97^b b First-order kinetic.

Sociedade Brasileira de Farmacognosia Universidade Federal do Paraná, Laboratório de Farmacognosia, Rua Pref. Lothario Meissner, 632 - Jd. Botânico, 80210-170, Curitiba, PR, Brasil, Tel/FAX (41) 3360-4062 - Curitiba - PR - Brazil
E-mail: revista@sbfgnosia.org.br

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[1] * Corresponding author. E-mail:valquiria.bassani@ufrgs.br (V.L. Bassani).