Search

Pueraria lobata root and Glycine max (L.) Merrill are rich in phytoestrogens. However, these bioactive ingredients have limited bioavailability due to their high molecular weight. In this study, we extracted two natural products and fermented with Lactiplantibacillus plantarum before mixing the fermented extracts (FPE‐FGE). To understand whether FPE‐FGE could alleviate menopause with dyslipidemia, we examined their effects on ovariectomy (OVX)‐induced dyslipidemia in mice. Oral administration of the FPE‐FGE (1:9, 3:7, and 9:1) did not affect safety‐related biomarkers, such as uterus index (%), vagina index (%), aspartate aminotransferase, alanine aminotransferase, blood urea nitrogen, and creatinine. Furthermore, FPE‐FGE (1:9, 3:7, and 9:1) increased the levels of 17β‐estradiol (E2) and expression of uterus estrogen receptor β (ERβ); there was little effect on the expression of uterus estrogen receptor α (ERα), and reduced the levels of gonadotropins, such as luteinizing hormone (LH) and follicle‐stimulating hormone (FSH). However, only the FPE‐FGE (3:7) reduced the levels of blood lipids, including total cholesterol (TC) and LDL‐cholesterol (LDL‐C). Accordingly, FPE‐FGE (3:7) upregulated endothelial nitric oxide synthase (eNOS), nitric oxide (NO), cyclic guanosine monophosphate (cGMP), and protein kinase G (PKG). In conclusion, FPE‐FGE (3:7) attenuated the menopausal dyslipidemia by upregulating eNOS‐NO‐cGMP signaling pathway. [ABSTRACT FROM AUTHOR]

Introduction: Sennosides are the main active constituents of the dried leaves and/or pods of Senna alexandrina Mill. that are used as laxatives. A hypothesis is that aglycones are formed during the degradation of sennosides. However, it is unknown, whether this happens under visible light exposure and how photosensitive sennosides behave in solution. Objectives: Pure anthraquinone glycosides were tested on their behaviour during sample preparation in the lab under visible light exposure in dependence on the instability of the solvent. Materials and methods: Samples before and after exposure were analysed using UHPLC with UV/Vis and MS detection. Results: Under visible light protection, the solutions were stable for 14 days at room temperature whereas a loss of 20%–60% was measured after 1 day of light exposure. The loss of sennosides due to degradation can be as fast as up to 2%–2.5% per hour, which might have a tremendous impact on phytochemical analysis results during the course of an analysis. The formation of aglycones was not observed in the degradation of sennosides and rhein‐8‐O‐glucoside. Conclusion: Aglycones could not be found as a result of the forced degradation. The solutions of sennosides clearly need to be protected from light to obtain reliable analytical results, and light protection is a major point for the stability of liquid preparations. Sennosides are the main active constituents of leaves and pods of Senna alexandrina Mill., used as laxatives. Light‐induced degradation of sennoside references during analysis is yet unknown. Samples before and after exposure were analysed using UHPLC‐UV/Vis/MS. Under light protection, the solutions were stable for 14 days, whereas a loss of 20%−60% after 1 day of visible light exposure was observed. The degradation rate ranged between 2% and 2.5%/h. Formation of aglycones was not observed during degradation of sennosides and rhein‐8‐O‐glucoside. [ABSTRACT FROM AUTHOR]

The isoflavone aglycone (IA) contents of commercial fermented soybean products in Korea, such as cheonggukjang and doenjang, and the IA-producing ability of the Bacillus subtilis strains isolated from the products were examined. Among three commercial products, product C (doenjang), which is produced using a long fermentation method, showed the highest conversion rate of isoflavone glucosides to aglycones. Of all eight B. subtilis strains isolated from the products, four strains had the same or higher level of IA production than B. subtilis (natto), with the C-3 strain showing the highest level. Hence, the difference in the conversion rate among the products might be attributed not only to fermentation time during the manufacturing process, but also the IA-producing ability of the B. subtilis strains. Moreover, the C-3 strain produced IA during the early stage of culture with soybean liquid medium, and the IA-producing ability of the C-3 strain in the fermentation with soybean solid medium was higher than that of B. subtilis (natto). Thus, the rapid IA production by the B. subtilis C-3 strain might contribute to the high IA content of product C. [ABSTRACT FROM AUTHOR]

AbstractThe fruits of citrus family are rich in flavonoids with superior antioxidant properties; citrus bioactive components are potentially beneficial without adverse effects or cytotoxicity in healthy individuals. Citrus fruit peel contains ample amount of hesperidin which is flavanone glycoside and has showed effective role in biological systems as an antioxidant and anti-inflammatory bioactive compound. Different studies have investigated such roles of hesperidin. Due to superior antioxidant potential of hesperidin and its derivatives, these compounds have been intensively studied for their anti-cancer and cardio protective perspective. This review article is a collection of updated data covering different aspects of hesperidin and its derivatives, like occurrence, physical and chemical composition, pharmacokinetics and safety of these compounds. Moreover, effective role of these compounds against different lifestyle-related metabolic syndromes in mechanistic perspective has also been extensively discussed in this article.

Menopause is a significant phase in a woman's life. Menopausal symptoms can affect overall well-being and quality of life. Conventionally, hormone replacement therapy (HRT) is used to alleviate menopausal symptoms; however, depending on the conditions, HRT may lead to side effects, necessitating the exploration of alternative therapies with fewer side effects. In this study, we investigated the effects of a combination of soybean germ extract (S30) containing 30% (w/w) isoflavone and a probiotic, Lactobacillus gasseri (LGA1), on menopausal conditions in an ovariectomized (OVX) rat model. We evaluated the impact of S30+LGA on body weight, estrogen markers, uterine and bone health, vascular markers, and neurotransmitter levels. The results revealed that treatment with S30+LGA1 significantly improved body weight and uterine and bone health. Moreover, S30+LGA1 demonstrated promising effects on lipid profile, liver function, and vascular markers and positively impacted serotonin and norepinephrine levels, indicating potential mood-enhancing effects. In conclusion, S30+LGA1, possessing anti-menopausal effects in vitro and in vivo, can be recommended as a soy-based diet, which offers various health benefits, especially for menopausal women. [ABSTRACT FROM AUTHOR]

Pueraria lobata roots and Glycine max (L.) Merrill are rich in isoflavones, which are phytoestrogens known to alleviate menopausal and some disease symptoms. However, the high molecular weight and poor bioavailability of isoflavones, owing to the glucose moieties attached to these glycosides, limit their practical use. Fermentation with lactic acid bacteria has been reported to convert glycosides into their aglycone forms. In this study, we investigated the health-promoting effects of fermented P. lobata root extract (FPE) and G. max (L.) Merrill extract (FGE) using ovariectomized mice. The extract was fermented with lactic acid bacteria. Lactiplantibacillus plantarum strains that convert glycosides to aglycones were selected, and in vitro and in vivo experiments were conducted to confirm various functionalities resulting from fermentation. FPE and FGE exhibited estrogen-like activities. In particular, fermentation increased the expression of estrogen receptor beta (ERβ), as a result of which the fermented extracts should probably not be associated with increasing the incidence of various female cancers—a common side effect of hormone replacement therapy. In addition, oral administration of FPE, FGE, or a mixture of the two extracts (FPE-FGE) to ovariectomized mice improved depressive symptoms by upregulating hippocampal brain-derived neurotrophic factor (BDNF). The expression of ERβ was the highest in the FPE-FGE group. These results indicate that FPE-FGE can be used as a raw material for the development of dietary supplements for menopausal women because it increases ERβ expression and alleviates the depressive-like behavior through the regulation of BDNF and neurotransmitters.

Menopause is a significant phase in a woman’s life. Menopausal symptoms can affect overall well-being and quality of life. Conventionally, hormone replacement therapy (HRT) is used to alleviate menopausal symptoms; however, depending on the conditions, HRT may lead to side effects, necessitating the exploration of alternative therapies with fewer side effects. In this study, we investigated the effects of a combination of soybean germ extract (S30) containing 30% (w/w) isoflavone and a probiotic, Lactobacillus gasseri (LGA1), on menopausal conditions in an ovariectomized (OVX) rat model. We evaluated the impact of S30+LGA on body weight, estrogen markers, uterine and bone health, vascular markers, and neurotransmitter levels. The results revealed that treatment with S30+LGA1 significantly improved body weight and uterine and bone health. Moreover, S30+LGA1 demonstrated promising effects on lipid profile, liver function, and vascular markers and positively impacted serotonin and norepinephrine levels, indicating potential mood-enhancing effects. In conclusion, S30+LGA1, possessing anti-menopausal effects in vitro and in vivo, can be recommended as a soy-based diet, which offers various health benefits, especially for menopausal women.

The production of isoflavone aglycones (IA) from isoflavone glucosides by a commercially available Bacillus subtilis (natto) strain and β-glucosidase activity associated with the reaction were examined using various media. These results were compared with those using B. subtilis strain 168. Some production of IA by B. subtilis (natto) in semi-solid soybean medium was shown; however, almost no production was observed in solid soybean medium. B. subtilis 168 produced IA abundantly in both media. Regarding fermentation in both soybean media, β-glucosidase activity was much lower in B. subtilis (natto) than in B. subtilis 168. When using liquid soybean medium, similar amounts of IA production were observed in both strains at similar culture incubation times (after the middle of fermentation). However, β-glucosidase activity was significantly lower in B. subtilis (natto) than in B. subtilis 168. In LB medium containing isoflavone glucosides (LB-DG medium), β-glucosidase activity of B. subtilis (natto) or B. subtilis 168 cultured in LB-DG medium supplemented with 0.2 % glucose at the early stage was significantly higher than that with no added glucose. Thus, B. subtilis (natto) can be a starter for IA production in semi-solid and liquid soybean medium, and the low IA content in natto (fermented soybean) products could be attributed to not only low β-glucosidase activity, but also a delay in IA production, which does not depend on β-glucosidase activity, during fermentation with B. subtilis (natto). Furthermore, the glucose content in soybean media might affect IA production during fermentation with Bacillus subtilis. [ABSTRACT FROM AUTHOR]

The acid hydrolysis of saponins is commonly performed by conventional heating to produce sapogenin-rich products of bioactive interest, but alternative hydrolysis methods and their impact on bioactivity have been unexplored. We compared the conventional method with microwave-assisted acid hydrolysis (MAAH) of a commercial saponin-rich extract from a typical saponin source, fenugreek, focusing on the study of temperature (100, 120, 130, 140, 150 °C) and time (10, 20, 30, 40 min) of hydrolysis. The impact of these factors was assayed on both the sapogenin yield and the bioactivity of the hydrolyzed products, specifically their antioxidant and lipase inhibitory activities. The highest sapogenin content (34 g/100 g extract) was achieved by MAAH at 140 °C and 30 min, which was higher than conventional hydrolysis at both reference conditions (100 °C, 60 min, 24.6 g/100 g extract) and comparative conditions (140 °C, 30 min, 17 g/100 g extract) (p < 0.001). Typical steroid artifacts from sapogenins were observed in very small amounts, regardless of the method of hydrolysis. Antioxidant activity of MAAH hydrolyzed extracts (around 80% DPPH inhibition) was barely affected by time and temperature, but pancreatic lipase inhibitory activity was higher (>65%) at lower MAAH temperature (<130 °C) and time (<30 min) of hydrolysis. MAAH is shown as a valid alternative to produce selective sapogenin-rich extracts from fenugreek with minor impact on their bioactivities, and whose magnitude can be modulated by the hydrolysis conditions. [ABSTRACT FROM AUTHOR]

[Display omitted] • Acid hydrolysis converts glycosidic polyphenols to their aglycone form. • Acid hydrolysis increases the content of phenolic compounds. • Acid hydrolysis enhances the antioxidant activity of extracts. • Acid-hydrolysed extracts inhibit lipid oxidation in oil-in-water emulsions. The antioxidant activity of the natural phenolic extracts is limited in particular food systems due to the existence of phenolic compounds in glycoside form. Acid hydrolysis post-treatment could be a tool to convert the glycosidic polyphenols in the extracts to aglycones. Therefore, this research investigated the effects of an acid hydrolysis post-treatment on the composition and antioxidant activity of parsley extracts obtained by an ultrasound-assisted extraction method to delay lipid oxidation in a real food system (i.e., soybean oil-in-water emulsion). Acid hydrolysis conditions were varied to maximize total phenolic content (TPC) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity. When extracts were exposed to 0.6 M HCl for 2 h at 80 ℃, TPC was 716.92 ± 24.43 µmol gallic acid equivalent (GAE)/L, and DPPH radical scavenging activity was 66.89 ± 1.63 %. Not only did acid hydrolysis increase the concentrations of individual polyphenols, but it also resulted in the release of new phenolics such as myricetin and gallic acid. The extract's metal chelating and ferric-reducing activity increased significantly after acid hydrolysis. In soybean oil-in-water emulsion containing a TPC of 400 µmol GAE/L, the acid-hydrolyzed extract had an 11-day lag phase for headspace hexanal compared to the 6-day lag phase of unhydrolyzed extract. The findings indicated that the conversion of glycosidic polyphenols to aglycones in phenolic extracts can help extend the shelf-life of emulsion-based foods. [ABSTRACT FROM AUTHOR]

Flavonoids are bioactive plant compounds that are widely present in the human diet. Estimating flavonoid intake with a high degree of certainty is challenging due to the inherent limitations of dietary questionnaires and food composition databases. This study aimed to evaluate the degree of reliability among flavonoid intakes estimated using four different approaches based on the two most comprehensive flavonoid databases, namely, United States Department of Agriculture (USDA) and Phenol Explorer (PE). In 678 individuals from the MAX study, a subcohort of the Diet, Cancer and Health-Next Generations cohort, dietary data were collected using three 24-h diet recalls over 1 year. Estimates of flavonoid intake were compared using flavonoid food content from PE as (1) aglycones (chromatography with hydrolysis), (2) aglycones transformed (converted from glycosides by chromatography without hydrolysis), (3) as they are in nature (glycosides, aglycones, and esters), and 4) using flavonoid content from USDA as aglycones (converted). Spearman's intra-class correlation (ICC) coefficient and weighted kappa (K) coefficient were calculated for the reliability analysis. When comparing PE total aglycones to USDA total aglycones, there was a moderate reliability when a continuous variable was used [ICC: 0.73, 95% confidence interval (CI): 0.70–0.76] and an excellent reliability when flavonoid intake was modeled as a categorical variable (K: 0.89, 95% CI: 0.88–0.90). The degree of reliability among all methods of estimated flavonoid intakes was very similar, especially between database pairs, for the flavanol subclass, while larger differences were observed for flavone, flavonol, and isoflavone subclasses. Our findings indicate that caution should be taken when comparing the results of the associations between flavonoid intakes and health outcomes from studies, when flavonoid intakes were estimated using different methods, particularly for some subclasses.

The acid hydrolysis of saponins is commonly performed by conventional heating to produce sapogenin-rich products of bioactive interest, but alternative hydrolysis methods and their impact on bioactivity have been unexplored. We compared the conventional method with microwave-assisted acid hydrolysis (MAAH) of a commercial saponin-rich extract from a typical saponin source, fenugreek, focusing on the study of temperature (100, 120, 130, 140, 150 °C) and time (10, 20, 30, 40 min) of hydrolysis. The impact of these factors was assayed on both the sapogenin yield and the bioactivity of the hydrolyzed products, specifically their antioxidant and lipase inhibitory activities. The highest sapogenin content (34 g/100 g extract) was achieved by MAAH at 140 °C and 30 min, which was higher than conventional hydrolysis at both reference conditions (100 °C, 60 min, 24.6 g/100 g extract) and comparative conditions (140 °C, 30 min, 17 g/100 g extract) (p < 0.001). Typical steroid artifacts from sapogenins were observed in very small amounts, regardless of the method of hydrolysis. Antioxidant activity of MAAH hydrolyzed extracts (around 80% DPPH inhibition) was barely affected by time and temperature, but pancreatic lipase inhibitory activity was higher (>65%) at lower MAAH temperature (

The transmembrane 16 (TMEM16) family contains 10 subtypes, and the function of each protein is different. TMEM16A is a calcium-activated chloride channel involved in physiological and pathological situations. Liquiritigenin is an aglycone derived from Glycyrrhiza glabra, and it is generated via the metabolism of enterobacterial flora. It has been known that liquiritigenin reduces pain sensation involving TMEM16A activation in primary sensory neurons. In addition, other pharmacological effects of liquiritigenin in physiological functions involving TMEM16A have been reported. However, the relationship between TMEM16A and liquiritigenin is still unknown. Therefore, we hypothesized that TMEM16A is inhibited by liquiritigenin. To confirm this hypothesis, we investigated the effect of liquiritigenin on TMEM16A currents evoked by intracellular free calcium in HEK293T cells transfected with TMEM16A. In this study, we found that liquiritigenin inhibited the mouse and human TMEM16A currents. To further confirm its selectivity, we also investigated its pharmacological effects on other ion channels, including transient receptor potential vanilloid 1 (TRPV1) and ankyrin 1 (TRPA1), which are non-selective cation channels involved in pain sensation. However, liquiritigenin did not inhibit the currents of TRPV1 and TRPA1 induced by capsaicin and allyl isothiocyanate, respectively. Therefore, our findings indicate that selective TMEM16A inhibition could be one molecular mechanism that explains liquiritigenin-induced pain reduction. Additionally, we also investigated the inhibitory effects of estrogens on TMEM16A because liquiritigenin reportedly binds to the estrogen receptor. In this study, a pregnancy-dependent estrogen, estriol, significantly inhibited TMEM16A. However, the efficacy was weak. Although there is a possibility that TMEM16A activity could be suppressed during pregnancy, the physiological significance seems to be small. Thus, the inhibitory effect of estrogen might not be significant under physiological conditions. Furthermore, we investigated the effect of dihydrodaidzein, which is an analog of liquiritigenin that has a hydroxyphenyl at different carbon atom of pyranose. Dihydrodaidzein also inhibited mouse and human TMEM16A. However, the inhibitory effects were weaker than those of liquiritigenin. This suggests that the efficacy of TMEM16A antagonists depends on the hydroxyl group positions. Our finding of liquiritigenin-dependent TMEM16A inhibition could connect the current fragmented knowledge of the physiological and pathological mechanisms involving TMEM16A and liquiritigenin.

There is great interest in the enhancement of isoflavones as one of the functional ingredients in soybean. This study aimed to investigate the effects of changes in the ecological environment over different planting times on isoflavone content. A total of 28 Korean soybean cultivars were grown at different planting times in late May, mid-June, and early July and their isoflavone content was measured over 2 years (2017 and 2018). Analyses of variance revealed significant effects of genotypes, planting times, years, and their interactions on isoflavone content. The average content of total isoflavone, as well as its component groups of malonylglucoside and aglycon, increased significantly as the seed planting time was delayed from late May to early July. The accumulation of each isoflavone component varied with changes in the planting time. The isoflavone content of the soybean cultivars for soy-sprout and soy-paste and tofu were higher for plantings in early July than for those in late May and/or mid-June, except for the black soybean cultivars. Despite significant correlations of the isoflavone content of the 28 cultivars among the three planting times, the responses of individual cultivars varied in isoflavone content by planting time. When planting was delayed, the time to flowering and maturity was also delayed and the number of days of growth from planting or flowering to maturity decreased; however, this was not related to isoflavone content. When planting was delayed, the temperature during the ripening period from flowering to maturity was lower, which was inversely related to the isoflavone content. [ABSTRACT FROM AUTHOR]

Introduction: The analysis and detection of steroidal saponins is mainly performed using chromatographic techniques coupled with mass spectrometry. However, nuclear magnetic resonance (NMR) spectroscopy is a potential tool that can be combined with these techniques to obtain unambiguous structural characterisation. Objective: This work provides a review of the carbon‐13 (13C)‐ and proton (1H)‐NMR spectroscopic data of aglycones from Agave saponins reported in the literature and also the development of an easy identification method for these natural products. Methods: The database Scifinder was used for spectroscopic data collection in addition to data obtained from the Cadiz Allelopathy research group. The keywords used were Agave, spirostanic, furostanic, and saponin. Results: The shielding variations produced by functional groups on the aglycone core and the structural features of the most representative aglycones from Agave species are described. The effects are additive for up to four long‐range connectivities. A method for the identification of aglycones (HMAI) is proposed to classify aglycones from Agave spp. through the use of 1H‐NMR and heteronuclear multiple bond correlation (HMBC) experiments. Conclusions: The HMBC spectrum is representative of the structural features of aglycones from Agave spp. The HMBC method for aglycone identification (HMAI) method allowed the identification of pure saponins or mixtures thereof and this method can be used in combination with chromatographic techniques coupled with mass spectrometry to provide a more thorough analysis of Agave samples that contain aglycones. Proton (1H) and carbon‐13 (13C) shielding variations produced by functional groups on the aglycone core and the structural features of the most representative aglycones from Agave species are described. The effects are additive for up to four long‐range connectivities. A method for the identification of aglycones (HMAI) is proposed to classify aglycones from Agave spp. through the use of 1H‐NMR and heteronuclear multiple bond correlation (HMBC) experiments. This method allowed the identification of pure saponins or mixtures thereof and it could be used in combination with chromatographic techniques coupled with mass spectrometry to provide a more thorough analysis of Agave samples that contain aglycones. [ABSTRACT FROM AUTHOR]

This work is designed to reveal the varietal characteristics of terpene glycosides (TGs) in ripe Meili grapes. TGs in grape skins were extracted using three ethanol/water solvents, purified and enriched using XAD-2 resin, and collected using ethyl acetate/methanol (9:1, v/v). The aglycones released from TGs were analyzed by headspace solid-phase microextraction–gas chromatography–mass spectrometry (HS-SPME–GC–MS). TGs were detected by ultra-high-performance liquid chromatography–quadrupole time-of-flight mass spectrometry (UPLC–Q-TOF-MS), the identification was conducted by both mass fragmentation and TGs database, and the quantitation was realized by octyl-β-d-glucopyranoside. Results showed that 19 aglycones for TGs were found in grape skins by GC–MS, which was mainly monoterpenol with molecular formula C10H18O (linalool, l-α-terpineol, geraniol, nerol, etc.), C10H20O (citronellol), and C10H18O2 (pyranoid/furanoid linalool oxide, etc.). C10H18O aglycones may be the most stable ones, and linalool was the most abundant, occupying 44.88–47.99% of the total content. Forty-nine TGs were detected by UPLC–Q-TOF-MS. Monoterpenol pentosyl-glucosides were the main TGs, especially C10H18O2 pentosyl-glucoside, which constituted 51.94–52.72% of the total concentration. [ABSTRACT FROM AUTHOR]

Basing on 2-fluoro-4-methoxyacetophenone 2-fluoro-4-hydroxyphenyl-1,2,3-thiadiazole was synthesized by means of the Hurd-Mori reaction. Under the conditions of phase transfer catalysis in water-chloroform system it was glycosylated with 1-α-bromo-2,3,4-tri-O-acetyl-D-xylopyranose. 2-Fluoro-4-hydroxy-1,2,3-selenadiazole can be prepared by oxidation of 2-fluoro-4-hydroxyacetophenone with selenium dioxide in acetic acid. Glycosylation of 2-fluoro-4-hydroxy-1,2,3-selenadiazole with 1-α-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose leads to formation of corresponding glycoside. Alternative pathway for preparing of 1-β-[3-fluoro-4-(1,2,3-selenadiazol-4-yl)-phenyl]-2,3,4-tri-O-acetyl-D-xylopyranose including synthesis of 2-fluoro-4-hydroxyacetophenone xyloside and subsequent formation of selenadiazole ring was developed. [ABSTRACT FROM AUTHOR]

An efficient first total synthesis of highly polar ulmoside A and (2 R ,3 R)-taxifolin-6- C -β- d -glucopyranoside, useful for the prevention of metabolic disorders, has been described. Key elements of the synthesis include a Sc(OTf)3-catalyzed regio- and stereoselective C -glycosidation on taxifolin in 35% yield with d -glucose and chiral semipreparative reverse-phase high-performance liquid chromatography (HPLC) for the separation of both taxifolins and the diastereomeric mixture of taxifolin-6- C -β- d -glucopyranosides. Correlation of the analytical data of synthetic ulmoside A and its diastereomer with a natural ulmoside A sample confirmed the assigned absolute stereochemistry of the natural products. [ABSTRACT FROM AUTHOR]

Aim: Studies on the anticancer effects of synbiotic fermented soymilk are rare. The aim of the present study was to evaluate the effect of synbiotic fermented soymilk supplemented with xylooligosaccharides and inoculated with Weissella cibaria FB069 (FSMXW) in the proliferation of colon cancer cell and compare it with the effect of soymilk inoculated with Lactobacillus rhamnosus GG (LGG). Methods and Results: Both FB069 and LGG were able to grow in soy‐based products and rapidly reduce their pH as a result of fermentation. The addition of XOS significantly enhanced the acidification rate, viscosity and total cell concentration in fermented soymilk inoculated with W. cibaria FB069. However, the same effect was not observed following inoculation with LGG. Moreover, the synbiotic FSMXW showed higher dextran, folate, GABA and aglycone content. FSMXW inhibited the proliferation of Caco‐2 and HCT116 cell lines, by reducing the transcription of MD2, TLR4, MyD88, and NF‐κb. Conclusions: The synbiotic soymilk containing XOS and W. cibaria FB069 increase nutrient and functional compounds through fermentation process. Significance and Impact of the Study: Our finding suggests that W. cibaria and XOS can be potentially employed in developing functional foods and health‐related products. [ABSTRACT FROM AUTHOR]

The reactions of abamectin and ivermectin aglycones with equimolar quantities of acid chlorides, succinic anhydride (pyridine, DMAP), or aryl isocyanates (DCM, Et 3 N) at ambient temperature resulted in absolutely selective monoacylation of the OH group in position 5 (5-OH) of the macrocyclic skeleton and afforded the monoesters in 20–87 % yields. The reaction of the aglycones or their 5-monoesters with acid chlorides in a 1:2 M ratio (pyridine, DMAP, rt) afforded the diesters bearing identical or different acyloxy fragments in positions 5 and 13. Theoretical studies suggested that the higher reactivity of 5-OH compared to 13-OH is related to both thermodynamic and kinetic preference of the corresponding tetrahedral intermediate and transition state structures stabilized via an intramolecular hydrogen bond. 2009 Elsevier Ltd. All rights reserved. [Display omitted] [ABSTRACT FROM AUTHOR]

In this study, the extraction conditions of bioactive aglycones from a celery extract supplemented with germinated soy were optimised by a response surface methodology. For subsequent enzymatic hydrolysis to enhance the apigenin content, increased production of its precursor apigetrin was firstly achieved through acidic extraction at optimal conditions, involving water at pH 1, at 75 °C for 2 h. Subsequently, a central composite design was conducted to analyse the pH (3–11) and temperature (25–35 °C) effects on the aglycone levels (apigenin, daidzein and genistein). The optimal extraction conditions were pH 7.02 and 29.99 °C, which resulted in a 40-fold increase in apigenin. The novel and cost-effective application of germinated soy β-glucosidase for the conversion of aglycones in non-soy foods is demonstrated. The enhanced bioactivities of aglycones may suggest potential applications for similar formulations as functional food ingredients.

Bacillus velezensis S141, a plant growth-promoting rhizobacteria (PGPR), was isolated from a soybean field in Thailand. Previous studies demonstrated that S141 enhanced soybean growth, stimulating nodulation for symbiotic nitrogen fixation with soybean root nodule bacteria, including Bradyrhizobium diazoefficience USDA110. Isoflavone glycosides are produced in soybean roots and hydrolyzed into their aglycones, triggering nodulation. This study revealed that S141 efficiently hydrolyzed two isoflavone glycosides in soybean roots (daidzin and genistin) to their aglycones (daidzein and genistein, respectively). However, S141, Bacillus subtilis 168, NCIB3610, and B. velezensis FZB42 hydrolyzed isoflavone glucosides into aglycones. A BLASTp search suggested that S141 and the other three strains shared four genes encoding β-glucosidases corresponding to bglA, bglC, bglH, and gmuD in B. subtilis 168. The gene inactivation analysis of B. subtilis 168 revealed that bglC encoded the major β-glucosidase, contributing about half of the total activity to hydrolyze isoflavone glycosides and that bglA, bglH, and gmuD, all barely committed to the hydrolysis of isoflavone glycosides. Thus, an unknown β-glucosidase exists, and our genetic knowledge of β-glucosidases was insufficient to evaluate the ability to hydrolyze isoflavone glycosides. Nevertheless, S141 could predominate in the soybean rhizosphere, releasing isoflavone aglycones to enhance soybean nodulation.

This study examines the direct chemical defensive role of maltol, a previously identified secondary metabolite found in balsam fir, Abies balsamea (L.) Mill. (Pinaceae), that was detected during herbivory of spruce budworm, Choristoneura fumiferana (Clemens) (Lepidoptera: Tortricidae). Although used extensively in many industries, in addition to being found in multiple plant species, its functional role in plants remains unknown. The objectives of this study were to quantify the amount of free maltol and its potential conjugated form, maltol glucoside, in various foliage age classes and to evaluate whether constitutive foliage levels of maltol have an impact on spruce budworm fitness in maltol supplementation assays. Gas chromatography–mass spectrometry (GC‐MS) analysis of balsam fir foliage showed that maltol is produced in all foliage age classes tested; however, concentrations were significantly higher in older foliage. Liquid chromatography–mass spectrometry–mass spectrometry (LC‐MS‐MS) analysis showed that maltol also exists in balsam fir in its glucosylated form, a unique discovery in conifers. Similar to maltol, maltol glucoside is also present in current and 1‐year‐old balsam fir foliage and in significantly higher concentration in older foliage. We investigated the impact of maltol‐treated diet on spruce budworm fitness. Maltol additions that reflected constitutive foliage concentrations caused a significant reduction in larval development rate and pupal mass, whereas higher concentrations were required to cause significant mortality. These results suggest that maltol may be an important component of a direct defense strategy in balsam fir against spruce budworm herbivory. [ABSTRACT FROM AUTHOR]

Soybean seed isoflavones are affected by various factors, but their responses to phosphorus (P) fertilization is largely unknown. A field experiment was conducted at Jackson and Milan in Tennessee from 2008 to 2010 to investigate the effects of P application rates on concentrations and production of individual and total isoflavone in the form of aglycones in soybean seeds on low and high P soils under no-tillage. Five P application rates (0, 10, 20, 30, and 40 kg P ha−1) plus the University of Tennessee recommended P fertilizer rate based on initial soil-test P were arranged in a randomized complete block design with four replicates. Phosphorus application rates exerted more frequent and greater impacts on aglycone concentrations on the low testing P soil at Milan, particularly under the dry year of 2008. Application of 10–20 kg P ha−1 was adequate for producing high individual and total aglycone concentrations in seeds on the low testing P soil. Genistein concentration was more responsive to P fertilization than daidzein and glycitein concentrations. Individual aglycone concentrations were positively correlated (r = 0.25–0.91) among each other. Total aglycone was positively correlated with seed protein but not with oil in concentration. In conclusion, pre-plant fertilization of 10–20 kg P ha−1 is frequently beneficial for producing high concentrations of individual and total aglycones in soybean seeds on low P soils, particularly under dry years, without any significant reductions in other key quality attributes such as protein or oil. [ABSTRACT FROM AUTHOR]

Background and objectives: In this study, 165 lactic acid bacteria (LAB) strains were isolated from three traditional Qu (LQ, XQ, and DQ) starters and screened for isoflavone glycoside biotransformation ability. The selected and identified strains were used as starter culture to enrich isoflavone aglycone in soybean sourdough bread (SSB). The in vitro gastrointestinal digestion, nutritional, and baking quality of soybean sourdough bread were determined. Findings: Based on yield, three strains identified as Pediococcus pentosaceus (D14, X11; 0.4940 and 0.5243 mg/g, respectively) and Lactobacillus plantarum group (L1, 0.6113 mg/g) showed the highest (p < 0.05) yield. The Lactobacillus plantarum group was confirmed to be L. plantarum using species‐specific multiplex PCR based on recA gene. L. plantarum was used as starter culture in soybean sourdough fermentation and bread preparation. In sourdough fermentation, sucrose was the preferred carbon source, as it supported cell growth and exhibited the highest β‐glucosidase enzyme activity (9.86 U/g). The aglycone content of SSB was increased under L. plantarum (5.93 mg/100 g). Similarly, the amino acid content was increased compared with soybean bread (SB) and wheat bread (WB). In vitro gastrointestinal digestion, SSB showed significant high release, absorption, and bioavailability of aglycone in bread. Baking quality (specific volume and texture) and overall acceptability of SSB were higher (p < 0.05) than SB and closer to WB. Conclusions: The use of β‐glucosidase from LAB strains during sourdough fermentation enhanced the bioactivity and overall acceptability of sourdough bread. Significance and novelty: This added new knowledge and the application potential as commercial starter in sourdough fermentation applications in the food industry. [ABSTRACT FROM AUTHOR]

Fermentation with filamentous fungi is known for the ability to convert bioactive compounds. The aim of this research was to investigate the metabolism of glycosidic derivatives of kaempferol and quercetin during fungal fermentation of extracts from cauliflower outer leaves and onion by Rhizopus oryzae and R. azygosporus. The highest release of kaempferol and quercetin was observed after 2 days and 1 day of fermentation with R. oryzae, respectively. It was proposed that glycosidic compounds were initially deglycosylated to form kaempferol-3-glucoside and quercetin-3-glucoside and then further metabolized into their aglycones. Clear differences in conversion efficiency towards the aglycones were observed between the two Rhizopus strains. Although both flavonoids only differ in one hydroxyl group, the metabolism of the glycosides towards their respective aglycones, kaempferol or quercetin, was different. It is concluded that the fermentation with R. oryzae and R. azygosporus could be considered as a way to produce kaempferol and quercetin aglycone from their glycosidic derivatives. [ABSTRACT FROM AUTHOR]

Carbohydrate structures containing alkyl groups as aglycones are useful for investigating enzyme activity and glycan-protein interactions. Moreover, linker-containing oligosaccharides with a spacer group are commonly used to print glycan microarrays or to prepare protein-conjugates as vaccine candidates. The structural accuracy of these synthesized glycans are essential for interpretation of results from biological experiments in which the compounds have been used and NMR spectroscopy can unravel and confirm their structures. An approach for efficient 1H and 13C NMR chemical shift assignments employed a parallel NOAH-10 measurement followed by NMR spin-simulation to refine the 1H NMR chemical shifts, as exemplified for a disaccharide with an azidoethyl group as an aglycone, the NMR chemical shifts of which have been used to enhance the quality of CASPER (http://www.casper.organ.su.se/casper/). The CASPER program has been further developed to aid characterization of linker-containing oligo- and polysaccharides, either by chemical shift prediction for comparison to experimental NMR data or as structural investigation of synthesized glycans based on acquired unassigned NMR data. The ability of CASPER to elucidate structures of linker-containing oligosaccharides is demonstrated and comparisons to assigned or unassigned NMR data show the utility of CASPER in supporting a proposed oligosaccharide structure. Prediction of NMR chemical shifts of an oligosaccharide, corresponding to the repeating unit of an O-antigen polysaccharide, having a linker as an aglycone and a non-natural substituent derivative thereof are presented to exemplify the diversity of structures handled. Furthermore, NMR chemical shift predictions of synthesized polysaccharides, corresponding to bacterial polysaccharides, containing a linker are described showing that in addition to oligosaccharide structures also polysaccharide structures having an aglycone spacer group can be analyzed by CASPER. [Display omitted] • Application of NOAH supersequences for sequential, parallel and time-shared acquisition of NMR experiments. • Automated structural elucidation of carbohydrate structures using unassigned 1D and 2D NMR chemical shift data. • Determination of absolute configuration of carbohydrate residues within oligosaccharide based on NMR data using CASPER. • Prediction of NMR chemical shifts of oligosaccharides having aglycones commonly used in synthetic carbohydrate chemistry. [ABSTRACT FROM AUTHOR]

Herein, five undescribed oleanane-type triterpenoid saponins, namely, psammosaponins A–E, along with nine known compounds, were isolated from the roots of Psammosilene tunicoides. Moreover, part of the ethanolic extract of P. tunicoides was acid-hydrolyzed and three aglycones were isolated from the resulting hydrolysate. The structures of all compounds were established through extensive analysis involving 1D and 2D NMR experiments, HRESIMS measurements, chemical derivatization, and comparison of spectroscopic data with the values reported in the literature. In all, 10 of the isolated saponins and the three aglycones were evaluated in the acetic acid-induced writhing model for their antinociceptive activity. At a dose of 40 mg/kg, these compounds exhibited significant inhibitory effects on the mouse writhing response, with inhibitions ranging from 31.9% to 79.3%. In addition, the structure–activity relationships of the isolates were discussed. Among the isolates, quillaic acid 3- O -glucuronide and 16α-hydroxygypsogenic acid showed better antinociceptive activity with inhibitions of 79.3% and 73.7%, respectively. Both isolates also exhibited antinociceptive activities in hot plate and formalin tests on mice. Their antinociceptive mechanism was explored in lipopolysaccharide–stimulated RAW 264.7 cells. These isolates could significantly inhibit the production of nitric oxide and interleukin-6 and downregulate the expression levels of inducible NO synthase, COX-1, and COX-2. Fourteen oleanane-type triterpenoid saponins including five undescribed triterpenoid saponins, psammosaponins A–E, were isolated from Psammosilene tunicoides , and three aglycones were obtained by hydrolysis of its ethanolic extract. Some of them showed significant antinociceptive activity. [Display omitted] • Five undescribed oleanane-triterpenoid saponins were isolated from Psammosilene tunicoides. • 13 isolated compounds exhibited antinociceptive activity with high inhibitions, up to 79.3%. • Two compounds could effectively inhibit the production of COX-1, iNOS, and IL-6. [ABSTRACT FROM AUTHOR]

[Display omitted] • P. lobata (PE) and G. max (L.) Merrill (GE) are rich in glycosidic phytoestrogens. • Aglycones in PE and GE fermented with lactic acid bacteria were identified. • The fermented extracts suppressed the depressive-like behavior in OVX mice. • The observed effect was through upregulation of hippocampal BDNF. • These extract can be raw materials for dietary supplements for menopausal women. Pueraria lobata roots and Glycine max (L.) Merrill are rich in isoflavones, which are phytoestrogens known to alleviate menopausal and some disease symptoms. However, the high molecular weight and poor bioavailability of isoflavones, owing to the glucose moieties attached to these glycosides, limit their practical use. Fermentation with lactic acid bacteria has been reported to convert glycosides into their aglycone forms. In this study, we investigated the health-promoting effects of fermented P. lobata root extract (FPE) and G. max (L.) Merrill extract (FGE) using ovariectomized mice. The extract was fermented with lactic acid bacteria. Lactiplantibacillus plantarum strains that convert glycosides to aglycones were selected, and in vitro and in vivo experiments were conducted to confirm various functionalities resulting from fermentation. FPE and FGE exhibited estrogen-like activities. In particular, fermentation increased the expression of estrogen receptor beta (ERβ), as a result of which the fermented extracts should probably not be associated with increasing the incidence of various female cancers—a common side effect of hormone replacement therapy. In addition, oral administration of FPE, FGE, or a mixture of the two extracts (FPE-FGE) to ovariectomized mice improved depressive symptoms by upregulating hippocampal brain-derived neurotrophic factor (BDNF). The expression of ERβ was the highest in the FPE-FGE group. These results indicate that FPE-FGE can be used as a raw material for the development of dietary supplements for menopausal women because it increases ERβ expression and alleviates the depressive-like behavior through the regulation of BDNF and neurotransmitters. [ABSTRACT FROM AUTHOR]

The present study evaluated the effects of acid-treated rutin on hyperlipidemia and obesity in high-fat diet (HFD)-induced obese mice. The mice consumed a HFD with or without acid-treated rutin for 7 weeks. Body weight gain considerably decreased, by approximately 33%, in the acid-treated rutin (AR) and quercetin (Q) groups compared to that in the HFD group. The adipocytes’ size in epididymal fat in AR and Q groups was significantly reduced compared to that in the HFD group (p < 0.05). Treatment with AR decreased the levels of triglycerides, total cholesterol, and low-density lipoprotein cholesterol compared to the HFD group. In particular, administration of AR significantly decreased serum triglyceride (36.82 mg/dL) by 46% compared to HFD (69.30 mg/dL). The AR group also showed significantly decreased atherogenic indices and cardiac risk factors. These results suggest that deglycosylated rutin generated by acid treatment enhances the anti-obesity and hypolipidemic effects in obese mice, and provides valuable information for improving the functional properties of glycosidic flavonoids.

Four new nerolidol-type sesquiterpene glucosides, triptergosidols A-D ( 1 - 4 ) were isolated from the leaves of Tripterygium wilfordii . Three aglycones, named triptergerols A ( 1 a), B ( 2 a), and C ( 3 a), were acquired by enzymatic hydrolysis of 1 - 3 . The structures of nerolidol-type sesquiterpenes were elucidated on base of kinds of spectroscopic analysis, and their absolute configurations were determined by CD method. In addition, compounds 1 - 4 were tested for cytotoxicity against two cell lines and inhibitory effects against NO production in RAW264.7 macrophage. [ABSTRACT FROM AUTHOR]