Preparation of Glycyrrhetic Acid .BETA.-Glycosides Having .BETA.(1.RAR.2)-Linked Disaccharides by the Use of 2-O-Trichloroacetyl-.BETA.-D-pyranosyl Chlorides and Their Cytoprotective Effects on Hepatic Injury in Vivo.

Saito, Setsuo; Sasaki, Yuka; Kuroda, Kaoru; Hayashi, Yasunobu; Sumita, Shigeya; Nagamura, Yoichi; Nishida, Keiji; Ishiguro, Isao

doi:10.1248/cpb.41.539

Cited by 21 publications

(13 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…However, the cultivated strain derived from the seed was identified as G. uralensis based on the morphologic characteristics of the falcate fruits, ovate leaflets (4-8 paired), and dense and compact racemes. 6) The underground parts of strain 83-555 were analyzed by HPLC. Figure 1 shows the HPLC profiles of the methanol extracts of the underground parts of strains 83-555 and 01A26-6 (a GL-producing strain).…”

Section: Resultsmentioning

confidence: 99%

“…Thus, GGL was isolated for the first time from higher plants; however, it has been previously reported to be synthesized from glycyrrhetic acid by stepwise glycosidation. 7) GGL has a sweet taste and has been reported to have a potent cytoprotective effect on CCl 4 -induced hepatotoxicity. , it is suggested that the glucuronidation of MGGA leading to GL is inhibited in strain 83-555.…”

Section: Isolation and Characterization Of A Triterpene Saponin In Thmentioning

confidence: 99%

See 1 more Smart Citation

Characterization of a Glycyrrhizin-Deficient Strain of <i>Glycyrrhiza uralensis</i>

Hayashi

Fujii

Iinuma

et al. 2013

Biological & Pharmaceutical Bulletin

View full text Add to dashboard Cite

A triterpene saponin, glucoglycyrrhizin, was isolated from a glycyrrhizin-deficient strain 83-555 of Glycyrrhiza uralensis (Leguminosae), and the structure was determined by chemical and spectral data to be 3-O-[β-D-glucopyranosyl-(1→2)-β-D-glucuronopyranosyl]-glycyrrhetinic acid. Since this saponin has a 2′-O-β-D-glucopyranosyl moiety instead of the 2′-O-β-D-glucuronopyranosyl moiety of glycyrrhizin, the glucuronidation of 3-O-β-D-glucuronopyranosyl-glycyrrhetinic acid leading to glycyrrhizin is inhibited in this strain. All 4 offspring of the 83-555 strain produced glucoglycyrrhizin. Interestingly, 2 of the offspring produced both glycyrrhizin and glucoglycyrrhizin, and sequence analysis of the pkr gene suggested that these 2 offspring were hybrids of 83-555 strain and glycyrrhizin-producing strains.Key words Glycyrrhiza uralensis; glycyrrhizin; mutant; saponin variation Glycyrrhizin (GL) is a sweet-tasting triterpene diglucuronide isolated from the roots and stolons of the Glycyrrhiza plant (licorice), which belongs to the family Leguminosae. Licorice is one of the most frequently used components in traditional medicine in Japan, and Glycyrrhiza uralensis FISCH. is mainly used for this purpose.1,2) Since G. uralensis is the most important Glycyrrhiza plant used for traditional medicine in Japan, it is important to elucidate the variations in the G. uralensis strains from the viewpoint of the medicinal resources related to licorice. In our previous study, comparative analysis of G. uralensis strains was undertaken to characterize variations in G. uralensis.3) During this process, we found a unique G. uralensis strain, 83-555, producing only a trace amount of glycyrrhizin. Therefore, in the present study, chemical characterization of the GL-deficient strain was examined, and a major triterpene saponin, glucoglycyrrhizin (GGL), was isolated and characterized from this strain. Furthermore, offspring of the strain 83-555 were analyzed to select for a high-GGLproducing strain. MATERIALS AND METHODS General Methods 1H-NMR and 13 C-NMR spectra were recorded using a Unity Inova-500 (Varian) spectrometer. Chemical shifts are given on a δ (ppm) scale with tetramethylsilane as the internal standard. Specific rotation was measured on a SEPA-300 (Horiba, Japan) spectrometer. Quantitative HPLC analysis and negative electrospray ionization (ESI)-MS were measured on an LCMS-IT-TOF (Shimadzu, Kyoto, Japan) spectrometer.Plant Materials G. uralensis strain 83-555 was derived from a seed obtained from the former East Germany in 1983 and was cultivated in the Kyoto Herbal Garden, Takeda Pharmaceutical Co., Ltd. G. uralensis strain 01A26-6 was derived from a seed collected in Kazakhstan, as reported previously. 4)Strain 83-555 was also cultivated in the Herbal Garden at the Osaka University of Pharmaceutical Sciences, and the harvested roots were used for the isolation of saponin. Seeds of strain 83-555 were collected from the Kyoto Herbal Garden, Takeda Pharmaceutical Co., Ltd., and 4 offspring derived from the seeds were cultivat...

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Isolation and Characterization Of A Triterpene Saponin In Thmentioning

confidence: 99%

Characterization of a Glycyrrhizin-Deficient Strain of <i>Glycyrrhiza uralensis</i>

Hayashi

Fujii

Iinuma

et al. 2013

Biological & Pharmaceutical Bulletin

View full text Add to dashboard Cite

show abstract

“…

…”

mentioning

confidence: 99%

“…Use of mercury salts for practical syntheses of triterpene glycosides is limited by their high toxicity whereas silver salts are expensive. As a rule, both methods produce a mixture of D-and E-O-glycosides in 30-70% yields [1][2][3][4].In continuation of our studies of the synthesis of biologically active GA analogs [8], we studied glycosylation of triterpenoids from licorice root using the convenient and inexpensive reagent iodine monobromide (I-Br), which was proposed earlier by Field and Kartha for synthesizing various simple glycosides and disaccharides [9,10]. However, it has not yet been used to synthesize triterpene glycosides.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and anti-HIV activity of triterpene 3-O-galactopyranosides, analogs of glycyrrhizic acid

et al. 2010

View full text Add to dashboard Cite

The synthesis of model triterpene glycosides that are analogs of glycyrrhizic acid (GA) with a modified carbohydrate chain is of great interest for studying the molecular mechanisms of GA biological activity, toxicity, and structure-activity relationships [1][2][3][4][5].The sugar moiety in most natural triterpene glycosides is bonded to the sapogenin 3-OH through a 1,2-trans-glycosidic bond [6]. Therefore, a key step in the synthesis of saponins is 3-O-glycosylation of the corresponding triterpene sapogenins by mono-and disaccharide glycosyl donors (GD). Forming such a bond between GD and sterically hindered 3-OH of triterpene alcohols is a rather complicated problem. Glycosylation of natural triterpenoids by readily available GD such as glycosylhalides is usually carried out using compounds of mercury [Hg(CN) 2 , HgBr 2 ] and silver (Ag 2 O, Ag 2 CO 3 , AgOTf) as promoters [1][2][3][4][5]7]. Use of mercury salts for practical syntheses of triterpene glycosides is limited by their high toxicity whereas silver salts are expensive. As a rule, both methods produce a mixture of D-and E-O-glycosides in 30-70% yields [1][2][3][4].In continuation of our studies of the synthesis of biologically active GA analogs [8], we studied glycosylation of triterpenoids from licorice root using the convenient and inexpensive reagent iodine monobromide (I-Br), which was proposed earlier by Field and Kartha for synthesizing various simple glycosides and disaccharides [9,10]. However, it has not yet been used to synthesize triterpene glycosides.We used methyl esters of 18E-glycyrrhetic acid (MeGLA) (3) and 18,19-dehydro-GLA (7) as alcohol components for glycosylation; 2,3,4,6-tetra-O-acetyl-D-D-galactopyranosylbromide (GalBr), as the GD [11], because glycosylation of sterically hindered triterpene alcohols by galactopyranosyl GD is rather complicated and poorly studied from a chemical viewpoint. Table 1 gives the results from the glycosylation. Carrying out the reaction in a mixture of anhydrous CH 3 CN:CH 2 Cl 2 (5:1, v/v) at -20 o -10°C for 18 h with GalBr:MeGLA:I-Br (2:1:2) formed a mixture of D-and E-D-galactopyranosides 4 and 5 in overall yield 35.6% (Scheme 1). The ratio of D-and E-anomers was 6:1 after separation of the reaction products over a column of silica gel (SG), i.e., the major product was the D-anomer 4, which was easily isolated from the product mixture also by recrystallization from EtOH. MeGLA 3-O-acetate 6 was isolated in small quantities as a side product.

show abstract

Current Synthesis of Triterpene Saponins

Sun

2009

Chemistry An Asian Journal

View full text Add to dashboard Cite

Triterpene saponins are a structurally and biologically diverse class of glycoconjugates of triterpenes that are widely distributed in terrestrial plants and some marine organisms. Current synthesis of these complex glycoconjugates has been discussed, whereupon the stereocontrolled glycosylation, global protection/deprotection, and the total synthesis of four unusual triterpene saponins are highlighted.

show abstract

Preparation of Glycyrrhetic Acid .BETA.-Glycosides Having .BETA.(1.RAR.2)-Linked Disaccharides by the Use of 2-O-Trichloroacetyl-.BETA.-D-pyranosyl Chlorides and Their Cytoprotective Effects on Hepatic Injury in Vivo.

Cited by 21 publications

References 1 publication

Characterization of a Glycyrrhizin-Deficient Strain of <i>Glycyrrhiza uralensis</i>

Characterization of a Glycyrrhizin-Deficient Strain of <i>Glycyrrhiza uralensis</i>

Synthesis and anti-HIV activity of triterpene 3-O-galactopyranosides, analogs of glycyrrhizic acid

Current Synthesis of Triterpene Saponins

Contact Info

Product

Resources

About