Plant Source Foods
Chuong Pham-Huy, Bruno Pham Huy in Food and Lifestyle in Health and Disease, 2022
Glycosides are natural organic compounds, usually of plant origin, formed by a sugar (carbohydrate) named glycone linked to a non-sugar compound named aglycone or genin (37). By hydrolysis, glycosides yield one or more sugars. The aglycon may be a terpene, a flavonoid, a coumarin, or any other natural product. Among the sugars found in natural glycosides, D-glucose is the most abundant one, L rhamnose and L-fructose also occur quite frequently (37). Based on the chemical properties, glycosides can be classified into Cardiac glycosides, Phenolic glycosides (flavonoids, lignans and other phenolic compounds), Aldehyde glycosides, Cyanogenic glycosides, Anthraquinone and and Saponin glycosides (37). The aglycones of cardiac glycosides or digitalis glycosides are: digitoxin, digoxin, and gitoxin, and they have a direct effect on myocardial contraction. They are cardiotonic. Saponins are compounds that possess a lipid soluble aglycone consisting of either a sterol or a triterpenoid attached to a water-soluble sugar unit (monosaccharide or oligosaccharide) (33–34, 37). Saponins are found in peas, beans, tomatoes, spinach, asparagus, onions, garlic, potatoes, and ginseng (33).
Nutritional Attributes of Cereal Grains And Legumes as Functional Food: A Review
Megh R. Goyal, Durgesh Nandini Chauhan in Plant- and Marine-Based Phytochemicals for Human Health, 2018
Three main isoflavones present in soybean are: daidzein, genistein, and glycitein. Conjugated aglycones comprise esterified 6″-O-malonylβ-glycosides, 6″-O-acetyl-β-glycosides, and β-glycosides; and it includes a total of 12 isoflavones.83 Phytoestrogens present in it exhibit antiproliferative activities and also regulate the immune system.28, 85 Despite the presence of various bioactive compounds, it has anti-nutritional effects.127 Soybean is anti-allergic, affecting almost 0.4% of children and 0.25% of adults.135 The Food and Agriculture Organization has listed it as one of the eight most common allergenic foods.126 Soybean contains various allergenic glycol proteins that lead to various allergic symptoms such as eczema, atopic dermatitis, and asthma. Several soybean allergens have been classified into families such as cupin superfamily, prolamin superfamily, pathogenesis-related proteins, and profilins.5, 126, 153
Anthocyanins and Their Health Benefits
Robert E.C. Wildman, Richard S. Bruno in Handbook of Nutraceuticals and Functional Foods, 2019
The degree of glycosylation and acylation of aglycones also impact the antioxidant capabilities and bioactivity of ACNs. The antioxidant properties and biological activities of ACNs increase with a decreasing degree of glycosylation. Given that aglycones are devoid of glycosylation, they have greater levels of oxidation than their parent ACNs as measured by their ability to inhibit the fluorescence intensity decay of the extrinsic probe, 3-[p-(6-phenyl)-1,3,5-hexatrienyl]-phenylpropionic acid, due to free radicals generated during metal ion-induced peroxidation. It was also found that the anti-cancer properties of ACNs are affected by their glycosylation and acylation patterns.10 For example, when the number of sugar moieties on CYA glycosides was decreased, both the antioxidant and proinflammatory cyclooxygenase inhibitory activity increased.1,15–17 In studies in vitro, acylation of potato ACNs with different cinnamic acid derivatives led to different antioxidant activities. When potato ACNs were acylated with p-coumaric acid, they exhibited higher antioxidant activity when compared to ACNs acylated with ferulic acid and caffeic acid moieties,18 further suggesting that acylation patterns can affect the antioxidant properties of ACNs.
Targeting the gut microbial metabolic pathway with small molecules decreases uremic toxin production
Published in Gut Microbes, 2020
Yingyi Wang, Jianping Li, Chenkai Chen, Jingbo Lu, Jingao Yu, Xuejun Xu, Yin Peng, Sen Zhang, Shu Jiang, Jianming Guo, Jinao Duan
The above data showed that ISO inhibits indole production after releasing its aglycone quercetin. We then evaluated the structure-activity relationships of other flavonoid aglycones. Our data show that the inhibitory potency of myricetin and quercetin exceeds 50% (Figure 7(a,b)), which is higher compared to other flavonol aglycones. The inhibitory potencies of kaempferol (with only one OH-group in the B-ring) and galangin (with no OH-group on B-benzene) were only 20%. These data indicate that the phenolic hydroxyl group is important for aglycone activity. Interestingly, the flavonoid aglycone with more phenolic hydroxyl groups showed increased inhibitory potency. When the para-OH of the B-ring phenolic hydroxyl group was methylated (tamarixetin and kaempferide), the inhibitory potency of the methylated aglycon decreased significantly.
Flavonoids as inhibitors of human neutrophil elastase
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2021
Katarzyna Jakimiuk, Jakub Gesek, Atanas G. Atanasov, Michał Tomczyk
The significance of O-glycosylation at the A-ring (C7) and C-ring (C3) positions can be observed by comparing the inhibitory levels of apigenin and luteolin and its 7-O-glucosides cosmosiin, and cynaroside, respectively. Based on the IC50 values, aglycones possess stronger activity while their 7-O-glucosides reveal no significant inhibitory effect. It is worth mentioning that 3-O-rhamnosylation of quercetin and kaempferol also reduced their activity. The values presented in Table 3 suggest that glucosylation or rhamnosylation at positions C-7 or C-3 presumably produce steric hindrances that prevent molecules from binding to enzymes126. In addition, a comparison of an anti-elastase potential of apigenin and apigenin 4′-O-β-d-glucoside leads to the conclusion that glucosylation of the hydroxyl group in B-ring also reduces its activity70,77.
Phytochemical constituents and protective efficacy of Schefflera arboricola L. leaves extract against thioacetamide-induced hepatic encephalopathy in rats
Published in Biomarkers, 2022
Ali M. El-Hagrassi, Abeer F. Osman, Mostafa E. El-Naggar, Noha A. Mowaad, Sahar Khalil, Manal A. Hamed
Acid hydrolysis was carried out for 2 h at 100 °C using 10 mL hydrochloric acid (2 mol/L). The yielded aglycones were then extracted with ethyl acetate. The ethyl acetate layer was dried with anhydrous Na2SO4 and evaporated. The hydrolyzed extract was subjected to paper chromatography (PC) Whatman No. 1 (Whatman Ltd., Maidstone, Kent, England) using 15% AcOH/water (Acetic acid: H2O, 15: 85) and BAW (n-Butanol: Acetic acid: H2O 4:1:5, upper layer) to detect the flavonoid aglycones. Also, the aqueous layer was carefully neutralized, then subjected to PC investigation using BBPW (Benzene: n-Butanol: pyridine: Water; 1:5:3:3, upper layer) to detect the sugars. The dried chromatograms were visualized by an aniline phthalate reagent (Swanston-Flatt et al. 1990). The sugar spots were observed in daylight. The Rf values of tested sugars were compared with those of reference sugars (Al-Wakeel et al. 1988, Saleh et al. 1990).