Isolation of 2,4,4′-Trihydroxydeoxybenzoin and 3′-Hydroxydaidzein from Soybean Miso (original) (raw)

Efficient protocol for isolation and purification of different soyasaponins from soy hypocotyls

Journal of Separation Science, 2012

Soyasaponins are naturally occurring triterpenoid glycosides associated with many biological activities. The aim of the present study was to develop an effective method for isolation and purification of differently glycosylated, acetylated, and 2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP)-conjugated soyasaponins from soy hypocotyls. Both gel filtration using Sephadex LH-20 chromatography (Amersham Pharmacia Biotech AB; elution phase: methanol, flow rate: 3.0 mL/min, sample loading: 60 mg) and high-speed countercurrent chromatography (stationary phase: n-butanol-acetic acid (5.0%, v/v), mobile phase: water flow rate: 3.0 mL/min, sample loading: 100 mg) could effectively fractionate isoflavones and soyasaponins from the crude extract with yield of soyasaponin complexes 20.5 mg and 22.3 mg, respectively. After fractionation, the soyasaponin complexes could be purified further using preparative HPLC to separate individuals. A total of nine soyasaponins, triacetyl soyasaponin Ab (yield 1.55%, HPLC purity >98%), Aa (2.68%, >99%), Ab (18.53%, >98%), Ae (0.85%, >98%), Ba (0.63%, >91%), Af (1.12%, >85%), Bb (3.45%, >98%) and Be (0.59%, >76.8%) were obtained. DDMP-conjugated groups, ␣g (2.06%, >85%), ␤g (7.59%, >85%), and ␥g (0.29%, >85%) that were very labile even in mild conditions, were also collected. The method described here can be used as an effective protocol to separate different soyasaponins occurring in the original sample.

Quantification of the Group B Soyasaponins by High-Performance Liquid Chromatography

Journal of Agricultural and Food Chemistry, 2002

High-performance liquid chromatographic methods were developed for the isolation and quantitative determination of the group B soyasaponins, including 2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP)-conjugated soyasaponins Rg, g, and a, and their non-DDMP counterparts, soyasaponins V, I, and II, respectively, with formononetin used as the internal standard. The limits of quantification for soy products were 0.11-4.86 µmol/g. The within-day and between-days assay coefficients of variation were <9.8 and < 14.3%, respectively. The group B soyasaponin concentrations in 46 soybean varieties ranged from 2.50 to 5.85 µmol/g. Soy ingredients (soybean flour, toasted soy hypocotyls, soy protein isolates, textured vegetable protein, soy protein concentrates, and Novasoy) and soy foods (commercial soy milk, tofu, and tempeh) contained the group B soyasaponins from 0.20 to 114.02 µmol/g. There was no apparent correlation between isoflavone and soyasaponin concentrations in the soy products examined.

Overproduction of Soyasaponin I by Tipuana speciosa (Benth.) cell culture

African Journal of Biological Sciences, 2021

Plant cell and tissue cultures are promising biotechnological tools for the production of a myriad of bioactive secondary metabolites on demand. Discoveries of cell cultures capable of producing specific medicinal compounds at a rate similar or superior to that of intact plants have been accelerated in the last few years. Soyasaponins have recently gained more attention due to their biological activities and health-promoting functions. There are many reports relating the bioactive benefits of soyasaponins to their chemical structure mainly Soyasaponin I which possess unique pharmacological actions. Our previous study indicated that Tipuana speciosa (Benth.) leaves extract showed promising antimalarial and nephroprotective activities. This study aimed to isolate Soyasaponin I, a major compound in the leaves extract and the use of cell suspension culture as a biotechnological route for high-yield production of this bioactive molecule. The compound was identified by LC-MS/MS analysis and other NMR techniques. To the best of our knowledge, there is no previous studies have been undertaken for the isolation and the production of Soyasaponin I from T. speciosa leaves using plant tissue culture technology. Our data showed that the callus and cell aggregate of T. speciosa represent an over producer cell lines (220 folds) compared to the whole plant.