- TRITERPENE GLUCURONIDES AND THEIR USE AS FLAVOR MODIFIERS
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The present disclosure generally provides triterpene glucuronides, and the use of such compounds and related compounds as flavor modifiers. In some aspects, the disclosure provides certain compositions that include such triterpene glucuronides, such as compositions that include such triterpene glucuronides and one or more other sweeteners. In some other aspects, the disclosure provides methods of reducing the caloric content of a sweetened article, such as a sweetened food or beverage product.
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Page/Page column 41-42
(2021/07/02)
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- Chemical synthesis method of glycyrrtinic acid 3-O-mono-beta-D-glucuronide (GAMG)
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The invention discloses a chemical synthesis method of glycyrrtinic acid 3-O-mono-beta-D-glucuronide (GAMG), and belongs to the fields of organic synthesis, medicinal chemistry, and food science. Abundant and cheap glycyrrhetinic acid is taken as the primary raw material, and GAMG is simply and easily synthesized by following five steps: carboxyl to benzyl ester conversion, glycosidation between C3 hydroxyl groups and a fully benzoylated methyl glucuronate glycosyl donor, methyl removal, benzoyl removal, and benzyl removal. The raw materials and reagents are cheap, the reaction conditions aremild, the operation is simple, the yield is good, and the GAMG chemical synthesis method is feasible.
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- The mechanism of hydrothermal hydrolysis for glycyrrhizic acid into glycyrrhetinic acid and glycyrrhetinic acid 3-O-mono-β-d-glucuronide in subcritical water
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To improve the bioactivity and sweetness properties of glycyrrhizic acid (GL), the hydrothermal hydrolysis of GL into glycyrrhetinic acid (GA) and glycyrrhetinic acid 3-O-mono-β-d-glucuronide (GAMG) in subcritical water was investigated. The effects of temperature, time and their interaction on the conversion ratios were analyzed and the reactions were elaborated with kinetics and thermodynamics. The results showed that GL hydrothermal hydrolysis was significantly (P 0.05) affected by reaction time and temperature, as well as their interaction, and could be fitted into first-order kinetics. The thermodynamic analysis indicated that the hydrolysis of GL was endergonic and non-spontaneous. The hydrolytic pathways were composed of complex consecutive and parallel reactions. It was concluded that subcritical water may be a potential medium for producing GAMG and GA.
- Fan, Rui,Li, Nan,Xu, Honggao,Xiang, Jun,Wang, Lei,Gao, Yanxiang
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p. 912 - 921
(2015/06/30)
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- Synthesis, molecular docking and biological evaluation of Glycyrrhizin analogs as anticancer agents targeting EGFR
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Glycyrrhizin (GA) analogs in the form of 3-glucuronides and 18-epimers were synthesized and their anticancer activities were evaluated. Alkaline isomerization of monoglucuronides is reported. In vitro and in vivo studies showed that glycyrrhetinic acid monoglucuronides (GAMGs) displayed higher anticancer activities than those of bisglucuronide GA analogs, while anticancer activity of the 18α-epimer was superior to that of the 18βepimer. 18α-GAMG was firstly nicely bound to epidermal growth factor receptor (EGFR) via six hydrogen bonds and one charge interaction, and the docking calculation proved the correlation between anticancer activities and EGFR inhibitory activities. Highly active 18α-GAMG is thus of interest for the further studies as a potential anticancer agent.
- Yang, Yong-An,Tang, Wen-Jian,Zhang, Xin,Yuan, Ji-Wen,Liu, Xin-Hua,Zhu, Hai-Liang
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p. 6368 - 6381
(2014/06/10)
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- Efficient synthesis of glycyrrhetinic acid glycoside/glucuronide derivatives using silver zeolite as promoter
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3-O-Glycopyranosides of glycyrrhetinic acid have been synthesized in good to high yields and excellent stereoselectivity using glycosyl bromide donors and silver zeolite as promoter. In addition to the preparation of glycosides containing β-linked glucosy
- Ruiz, Maria Carmen del Ruiz,Amer, Hassan,Stanetty, Christian,Beseda, Igor,Czollner, Laszlo,Shah, Priti,Jordis, Ulrich,Kueenburg, Bernhard,Classen-Houben, Dirk,Hofinger, Andreas,Kosma, Paul
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experimental part
p. 1063 - 1071
(2009/09/05)
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- In vitro and in vivo evaluation of the enhancing activity of glycyrrhizin on the intestinal absorption of drugs
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Purpose. The enhancing activity of dipotassium glycyrrhizinate (Grz) on the intestinal absorption of drugs has been demonstrated in an in vitro study using Caco-2 cell monolayers and in an in vivo absorption study in rats. Methods. The hydrolysis of Grz by luminal content and mucosa of the rat colon was investigated. The absorption-enhancing activity of Grz and its hydrolysates was estimated by changes in transepithelial electrical resistance (TEER) and the permeation of sodium fluorescein (Flu-Na) in Caco- 2 cell monolayers. It was further evaluated through the absorption of salmon calcitonin (SCT) in the rat colon. Results. Grz was not hydrolyzed to glycyrrhetinylmonoglucuronide (GrMG) and glycyrrhetinic acid (GA) by colonic mucosa, but, rather by the β-glucuronidase in colonic flora. The hydrolysis of Grz to GrMG was extremely slow and the GrMG produced was rapidly regenerated to GA. Grz and GrMG had no effect on TEER nor on the permeability of Flu-Na across Caco-2 cell monolayers. On the other hand, GA decreased TEER and increased the permeability of Flu-Na in a dose-dependent manner. However, Grz and GrMG enhanced the plasma calcium-lowering effect of sCT after administration in the rat colon. The coadministration of sCT and GA in the rat colon induced the strongest plasma calcium-lowering effect and the highest plasma concentration of sCT. Conclusions. The in vivo enhancing- activity of Grz in the absorption of drugs is dependent on GA, a hydrolysis product of Grz resulting from the action of β-glucuronidase in intestinal flora.
- Imai, Teruko,Sakai, Michinori,Ohtake, Hiroshi,Azuma, Hidekazu,Otagiri, Masaki
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- Sweetness of glycyrrhetic acid 3-O-beta-D-monoglucuronide and the related glycosides.
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To improve the taste profile of glycyrrhizin (1, the saponin of licorice root, relative sweetness to sucrose: x170), a variety of 3-O-glycosides of glycyrrhetic acid were prepared and their sweetness evaluated. It was found that a significant enhancement of sweetness was observed for the 3-O-beta-D-xyloside and the 3-O-beta-D-glucuronide (MGGR). Especially, MGGR had a high sweetness relative to sucrose; x941, and would appear to be a new potent sweetener.
- Mizutani,Kuramoto,Tamura,Ohtake,Doi,Nakaura,Tanaka
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p. 554 - 555
(2007/10/02)
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- Saponin and sapogenol. XLIX. On the constituents of the roots of Glycyrrhiza inflata BATALIN from Xinjiang, China. Characterization of two sweet oleanane-type triterpene oligoglycosides, apioglycyrrhizin and araboglycyrrhizin
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Two sweet oleanane-type triterpene oligoglycosides named apioglycyrrhizin and araboglycyrrhizin were isolated from the air-dried roots of Glycyrrhiza inflata BATALIN, collected in Xinjiang province (Shinkyo-Kanzo in Japanese), together with glycyrrhizin (3), licorice-saponins A3 (8), G2 (10), and H2 (11) and known flavonoid glycosides. On the basis of chemical and physicochemical evidence, the structures of apioglycyrrhizin and araboglycyrrhizin have been determined to be expressed as 3-O-[β-D- apiofuranosyl(1 → 2)-β-D-glucuronopyranosyl]glycyrrhetic acid (1) and 3-O- [α-L-arabinopyranosyl(1 → 2)-β-D-glucuronopyranosyl]glycyrrhetic acid (2), respectively. During the course of these studies, it has been found that the hydroxyl groups in the oligosaccharide moiety of the glucuronide saponins may be partially methylated by prolonged treatment with diazomethane in methanol. The sweetness of the saponins hitherto isolated from various Glycyrrhizae Radix has been examined and a structure-sweetness relationship, as compared with glycyrrhizin, has been found.
- Kitagawa,Hori,Sakagami,Hashiuchi,Yoshikawa,Ren
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p. 1350 - 1357
(2007/10/02)
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