Novel agents for enzymatic and fungal hydrolysis of stevioside

Abstract

A comparative study on the potential of some biological agents to perform the hydrolysis of stevioside was carried out, aiming at establishing an alternative methodology to achieve the aglycon steviol or its rearranged derivative isosteviol, in high yields to be used in the preparation of novel bioactive compounds. Hydrolysis reactions were performed by using filamentous fungi (Aspergillus niger, Rhizopus stolonifer and Rhizopus arrhizus), a yeast (Saccharomyces cerevisiae) and enzymes (pancreatin and lipases PL250 and VFL 8000). Pancreatin showed the best hydrolytic activity, furnishing isosteviol at 93.9% of yield, at pH 4.0, using toluene as a co-solvent. Steviol was produced using both pancreatin at pH 7.0 (20.2% yield) and A. niger at pH 7 (20.8% yield).

Enzymatic Production of Steviol Glucosides Using β-Glucosidase and Their Applications

“…Unlike Ste, steviol is rare in nature. Therefore, few studies have reported its synthetic methods (Ogawa et al, 1980;Ko et al, 2013;Nguyen et al, 2016;Milagre et al, 2009;Chen et al, 2014). Steviol is an aglycone of steviol glucosides.…”

“…This process requires a highly diluted system and a large amount of costly sodium periodate to achieve meaningful yields (Ogawa et al, 1980;Ko et al, 2013). To produce steviol from Ste, enzymatic methods have also been reported (Wan et al, 2012;Ko et al, 2013;Milagre et al, 2009;Nguyen et al, 2016;Chen et al, 2014;Mizukami et al, 1982) (Table 23.2). Steviol yield has been reported to be 20% by using pancreatin with ethanol as a cosolvent at pH 7.0 (Milagre et al, 2009).…”

“…To produce steviol from Ste, enzymatic methods have also been reported (Wan et al, 2012;Ko et al, 2013;Milagre et al, 2009;Nguyen et al, 2016;Chen et al, 2014;Mizukami et al, 1982) (Table 23.2). Steviol yield has been reported to be 20% by using pancreatin with ethanol as a cosolvent at pH 7.0 (Milagre et al, 2009). The yield is 10% with fungal lipase/ethanol at pH 4.0 and 20.8% with Aspergillus niger at pH 7.0 for seven days (Milagre et al, 2009).…”

“…Steviol yield has been reported to be 20% by using pancreatin with ethanol as a cosolvent at pH 7.0 (Milagre et al, 2009). The yield is 10% with fungal lipase/ethanol at pH 4.0 and 20.8% with Aspergillus niger at pH 7.0 for seven days (Milagre et al, 2009). Crude hesperidinase containing β-1,4-rhamnoglucosidase and flavonoid-β-glucosidase from a culture medium of A. niger has been used to break the glycoside bonds of Ste into steviol (Mizukami et al, 1982).…”

Structure-activity relationship study of diterpenes for treatment of Alzheimer’s disease

“…Stevioside (27) was obtained from Stevita Cristal® (gift of Steviafarma Industrial S.A., Brazil). 13 Nuclear Magnetic Resonance (NMR) spectra were determined on a Bruker Avance DRX 200 or 400 MHz or on a Agilent 400 MHz with tetramethylsilane (TMS) as internal standard in CDCl 3 , CD 3 OD, CD 3 COCD 3 and D 2 O. Chemical shifts (δ) are given in parts per million (ppm) relative to TMS.…”