Liquid chromatography/mass spectrometry-based structural analysis of soyasaponin Ab metabolites by human fecal microflora

Chang, Seo-Young; Han, Myung Joo; Joh, Eun-Ha; Kim, Dong-Hyun

doi:10.1016/j.jpba.2010.02.011

Cited by 10 publications

(7 citation statements)

References 20 publications

(26 reference statements)

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“…SA (purity, > 91%) and SB (purity, > 95%) were obtained as previously reported. − Briefly, dried soybeans (3 kg) were pulverized using a coffee mill, defatted with hexane (10 L), allowed to dry, extracted with ethanol (10 L) twice and concentrated in vacuo (65 g; soybean ethanol extract [SE] contained 0.1% soyasaponin Ab [SA] and 1.6% soyasaponin Bb [SB], whose contents were analyzed by high-performance liquid chromatography [HPLC], Figure C). The extract was suspended in water, extracted with n -butanol (15 L), and evaporated to dryness under reduced pressure (40 g).…”

Section: Methodsmentioning

confidence: 99%

Soyasaponins Ab and Bb Prevent Scopolamine-Induced Memory Impairment in Mice without the Inhibition of Acetylcholinesterase

Hong

Yoo

Woo

et al. 2014

J. Agric. Food Chem.

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Soy (Glycine max, family Leguminosae), which contains isoflavones and saponins as main constituents, is known to exhibit memory-enhancing effects. Therefore, to investigate the role of soyasaponins in memory impairments, we isolated soyasaponins Ab (SA) and Bb (SB) from soybean and measured their protective effects against scopolamine-induced memory impairment in mice. SA and SB significantly prevented scopolamine-induced memory impairment in passive avoidance and Y-maze tasks. Compared to SA, SB rescued memory impairment more potently. Treatment with SB (10 mg/kg, p.o.) protected memory impairment in passive avoidance and Y-maze tasks to 97% (F = 68.10, P < 0.05) and 78% (F = 35.57, P < 0.05) of untreated normal control level, respectively. SA and SB (10 mg/kg) also rescued scopolamine-induced memory impairment in Morris water maze task (F = 14.51, P < 0.05). In addition, soyasaponins preserved brain-derived neurotrophic factor (BNDF) expression (F = 33.69, P < 0.05) and cAMP response element-binding (CREB) protein phosphorylation (F = 91.62, P < 0.05) in the hippocampus of scopolamine-treated mice. However, SA and SB did not inhibit acetylcholinesterase in vitro and ex vivo. On the basis of these findings, we suggest that soybean, particularly soyasaponins, may protect memory impairment by increasing BDNF expression and CREB phosphorylation.

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Section: Methodsmentioning

confidence: 99%

Soyasaponins Ab and Bb Prevent Scopolamine-Induced Memory Impairment in Mice without the Inhibition of Acetylcholinesterase

Hong

Yoo

Woo

et al. 2014

J. Agric. Food Chem.

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“…8 The anaerobic incubation of soyasaponin Ab with human fecal specimens produced two main metabolites, soyasapogenol A and soyasapogenol A 3-β-Dglucuronide, despite the different metabolic activities and pathways among individuals. 9 When group B soyasaponins were digested by healthy women, the metabolite was soyasapogenol B and was excreted in the feces. 10 In particular, soyasaponin I was metabolized to soyasapogenol B by human fecal microorganisms via soyasaponin III or, alternatively, via soyasaponin III and soyasapogenol B 3-β-D-glucuronide with apparent first-order kinetics.…”

Section: ■ Introductionmentioning

confidence: 99%

“…The physiological effects of soyasaponins are dependent on their metabolism and absorption . The anaerobic incubation of soyasaponin Ab with human fecal specimens produced two main metabolites, soyasapogenol A and soyasapogenol A 3-β- d -glucuronide, despite the different metabolic activities and pathways among individuals . When group B soyasaponins were digested by healthy women, the metabolite was soyasapogenol B and was excreted in the feces .…”

Section: Introductionmentioning

confidence: 99%

Biological Functionality of Soyasaponins and Soyasapogenols

Guang

Chen

Sang

et al. 2014

J. Agric. Food Chem.

101

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Soyasaponins are a group of structurally complex oleanane triterpenoids primarily found in soybeans and have diverse biological properties. The recent investigations and findings (since 2000) regarding the biological functions of soyasaponins and their aglycones, including their anti-inflammatory, antimutagenic, anticarcinogenic, antimicrobial, and hepato- and cardiovascular-protective activities, are herein summarized. The primary conclusion is that the use of soyasaponins and soyasapogenols in functional foods should be considered.

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“…The resultant anaerobic medium was autoclaved at 121˝C for 20 min. Human fecal specimens were prepared according to previous methods [23,24], fresh human fecal sample was obtained from a healthy female volunteer who was not on any medication for three months, and had not drank alcohol or smoked for 48 h before fecal collection. A 10 g fecal sample was weighed and mixed with 50 mL of anaerobic dilution medium.…”

Section: Preparation Of Human Intestinal Bacterial Specimenmentioning

confidence: 99%

Ardipusilloside-I Metabolites from Human Intestinal Bacteria and Their Antitumor Activity

Cao

Wang

et al. 2015

Molecules

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Ardipusilloside-I (ADS-I) is a triterpenoid saponin extracted from Ardisia pusilla DC, and has been demonstrated to have potent antitumor activity. However, ADS-I metabolism in humans has not been investigated. In this study, we studied the biotransformation of ADS-I in human intestinal bacteria, and examined the in vitro antitumor activity of the major metabolites. Ultra-high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) was used to detect ADS-I biotransformation products, and their chemical structures were identified by high performance liquid chromatography-nuclear magnetic resonance (HPLC-NMR). The antitumor activity of the major metabolites was determined by the MTT assay. Here, we show that main reaction seen in the metabolism of ADS-I in human intestinal bacteria was deglycosylation, which produced a total of four metabolites. The structures of the two major metabolites M1 and M2 were confirmed by using NMR. MTT assay showed that ADS-I metabolites M1 and M2 have the same levels of inhibitory activities as ADS-I in cultured SMMC-7721 cells and MCF-7 cells. In conclusion, this study demonstrates deglycosylation as a primary pathway of ADS-I metabolism in human intestinal bacteria, and suggests that the pharmacological activity of ADS-I may be mediated, at least in part, by its metabolites.

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Liquid chromatography/mass spectrometry-based structural analysis of soyasaponin Ab metabolites by human fecal microflora

Cited by 10 publications

References 20 publications

Soyasaponins Ab and Bb Prevent Scopolamine-Induced Memory Impairment in Mice without the Inhibition of Acetylcholinesterase

Soyasaponins Ab and Bb Prevent Scopolamine-Induced Memory Impairment in Mice without the Inhibition of Acetylcholinesterase

Biological Functionality of Soyasaponins and Soyasapogenols

Ardipusilloside-I Metabolites from Human Intestinal Bacteria and Their Antitumor Activity

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