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Keywords = succinyl-glucosides

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12 pages, 2494 KB  
Article
Efficient Synthesis and In Vitro Hypoglycemic Activity of Rare Apigenin Glycosylation Derivatives
by Lin Zhao, Yuqiong Pei, Guoxin Zhang, Jiayao Li, Yujie Zhu, Mingjun Xia, Ke Yan, Wen Mu, Jing Han, Sen Zhang and Jinao Duan
Molecules 2023, 28(2), 533; https://doi.org/10.3390/molecules28020533 - 5 Jan 2023
Cited by 9 | Viewed by 2999
Abstract
Apigenin is a natural flavonoid with significant biological activity, but poor solubility in water and low bioavailability limits its use in the food and pharmaceutical industries. In this paper, apigenin-7-O-β-(6″-O)-d-glucoside (AG) and apigenin-7-O-β-(6″-O-succinyl)- [...] Read more.
Apigenin is a natural flavonoid with significant biological activity, but poor solubility in water and low bioavailability limits its use in the food and pharmaceutical industries. In this paper, apigenin-7-O-β-(6″-O)-d-glucoside (AG) and apigenin-7-O-β-(6″-O-succinyl)-d-glucoside (SAG), rare apigenin glycosyl and succinyl derivatives formed by the organic solvent-tolerant bacteria Bacillus licheniformis WNJ02 were used in a 10.0% DMSO (v/v) system. The water solubility of SAG was 174 times that of apigenin, which solved the application problem. In the biotransformation reaction, the conversion rate of apigenin (1.0 g/L) was 100% at 24 h, and the yield of SAG was 94.2%. Molecular docking showed that the hypoglycemic activity of apigenin, apigenin-7-glucosides (AG), and SAG was mediated by binding with amino acids of α-glucosidase. The molecular docking results were verified by an in vitro anti-α-glucosidase assay and glucose consumption assay of active compounds. SAG had significant anti-α-glucosidase activity, with an IC50 of 0.485 mM and enhanced glucose consumption in HepG2 cells, which make it an excellent α-glucosidase inhibitor. Full article
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18 pages, 3147 KB  
Article
Changes in Isoflavone Profile from Soybean Seeds during Cheonggukjang Fermentation Based on High-Resolution UPLC-DAD-QToF/MS: New Succinylated and Phosphorylated Conjugates
by Suji Lee, Ryeong Ha Kwon, Ju Hyung Kim, Hyemin Na, So-Jeong Lee, Yu-Mi Choi, Hyemyeong Yoon, So Young Kim, Yong-Suk Kim, Sang Hoon Lee, Seon Mi Yoo, Heon-Woong Kim and Chi-Do Wee
Molecules 2022, 27(13), 4120; https://doi.org/10.3390/molecules27134120 - 27 Jun 2022
Cited by 9 | Viewed by 2916
Abstract
In this study, thirty-eight isoflavone derivatives were comprehensively identified and quantified from the raw, steamed and fermented seeds of four selected soybean cultivars based on UPLC-DAD-QToF/MS results with reference to the previously reported LC-MS library and flavonoid database, and summarized by acylated group [...] Read more.
In this study, thirty-eight isoflavone derivatives were comprehensively identified and quantified from the raw, steamed and fermented seeds of four selected soybean cultivars based on UPLC-DAD-QToF/MS results with reference to the previously reported LC-MS library and flavonoid database, and summarized by acylated group including glucosides (Glu), malonyl-glucosides (Mal-Glu), acetyl-glucosides (Ac-Glu), succinyl-glucosides (Suc-Glu) and phosphorylated conjugates (Phos) in addition to aglycones. Among them, Suc-Glu and Phos derivatives were newly generated due to fermentation by B. subtilis AFY-2 (cheonggukjang). In particular, Phos were characterized for the first time in fermented soy products using Bacillus species. From a proposed roadmap on isoflavone-based biotransformation, predominant Mal-Glu (77.5–84.2%, raw) decreased rapidly by decarboxylation and deesterification into Ac-Glu and Glu (3.5–8.1% and 50.0–72.2%) during steaming, respectively. As fermentation continued, the increased Glu were mainly succinylated and phosphorylated as well as gradually hydrolyzed into their corresponding aglycones. Thus, Suc-Glu and Phos (17.3–22.4% and 1.5–5.4%, 36 h) determined depending on cultivar type and incubation time, and can be considered as important biomarkers generated during cheonggukjang fermentation. Additionally, the changes of isoflavone profile can be used as a fundamental report in applied microbial science as well as bioavailability research from fermented soy foods. Full article
(This article belongs to the Special Issue Bioactive Compounds in Fermented Foods and Beverages)
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8 pages, 1040 KB  
Article
Functional Characterization of an Anthocyanin Dimalonyltransferase in Maize
by Michael Paulsmeyer and John Juvik
Molecules 2021, 26(7), 2020; https://doi.org/10.3390/molecules26072020 - 1 Apr 2021
Cited by 9 | Viewed by 3592
Abstract
Anthocyanins are pigments with appealing hues that are currently being used as sources of natural colorants. The interaction of acylation on the stability of anthocyanin molecules has long been known. Maize is an abundant source of malonylglucoside and dimalonylglucoside anthocyanins. The enzyme Aat1 [...] Read more.
Anthocyanins are pigments with appealing hues that are currently being used as sources of natural colorants. The interaction of acylation on the stability of anthocyanin molecules has long been known. Maize is an abundant source of malonylglucoside and dimalonylglucoside anthocyanins. The enzyme Aat1 is an anthocyanin acyltransferase known to synthesize the majority of acylated anthocyanins in maize. In this paper, we characterize the substrate specificity and reaction kinetics of Aat1. It was found that Aat1 has anthocyanin 3-O-glucoside dimalonyltransferase activity and is only the second enzyme of this type characterized to this date. Our results indicate that Aat1 can utilize malonyl-CoA; succinyl-CoA and every anthocyanin 3-O-glucoside tested. Results of this study provide insight into the structure–function relations of dimalonyltransferases and give a unique insight into the activity of monocot anthocyanin acyltransferases. Full article
(This article belongs to the Special Issue Anthocyanins: Extraction, Purification and Applications)
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9 pages, 3054 KB  
Article
Sequential Biotransformation of Antcin K by Bacillus subtilis ATCC 6633
by Te-Sheng Chang, Chien-Min Chiang, Yi-Yun Siao and Jiumn-Yih Wu
Catalysts 2018, 8(9), 349; https://doi.org/10.3390/catal8090349 - 27 Aug 2018
Cited by 7 | Viewed by 5130
Abstract
The biotransformation of antcin K, a major ergostane triterpenoid from the fruiting bodies of Antrodia cinnamomea, by Bacillus subtilis (B. subtilis) ATCC 6633 was studied. Four metabolites from the biotransformation were isolated with preparative high-performance liquid chromatography and identified as [...] Read more.
The biotransformation of antcin K, a major ergostane triterpenoid from the fruiting bodies of Antrodia cinnamomea, by Bacillus subtilis (B. subtilis) ATCC 6633 was studied. Four metabolites from the biotransformation were isolated with preparative high-performance liquid chromatography and identified as 25S-antcin K 26-O-β-glucoside, 25R-antcin K 26-O-β-glucoside, 25S-antcin K 26-O-β-(6′-O-succinyl)-glucoside, and 25R-antcin K 26-O-β-(6′-O-succinyl)-glucoside with mass and nuclear magnetic resonance spectral analysis. By using either 25S-antcin K 26-O-β-glucoside or 25R-antcin K 26-O-β-glucoside as the biotransformation precursor, it was proven that 25S-antcin K 26-O-β-(6′-O-succinyl)-glucoside and 25R-antcin K 26-O-β-(6′-O-succinyl)-glucoside were biotransformed from 25S-antcin K 26-O-β-glucoside and 25R-antcin K 26-O-β-glucoside, respectively. To the best of our knowledge, this is the first study on the glycosylation of triterpenoids from A. cinnamomea, and the first time the succinylation of triterpenoid glycosides by microorganisms has been found. In addition, all four antcin K glucoside derivatives are new compounds. Full article
(This article belongs to the Special Issue Novel Enzyme and Whole-Cell Biocatalysis)
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