Show legend Show as text

Structure type: oligomer
Trivial name: glycyrrhizin, Glycyrrhizin
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_423153

• Article ID: 9743
  Kitagawa I, Zhou JL, Sakagami M, Taniyama T, Yoshikawa M "Licorice-saponins A3, B2, C2, D3, and E2, five new oleanene-type triterpene oligoglycosides from Chinese Glycyrrhizae radix" - Chemical and Pharmaceutical Bulletin 36(9) (1988) 3710-3713
  

  Ten new oleanene-type triterpene oligoglycosides were isolated from Chinese Glycyrrhizae Radix, the dried root of Glycyrrhiza uralensis Fischer [Tohoku-Kanzo (in japanese) from China], and the structures of five olygoglycosides, named licorice-saponins A3 (3), B2 (5), C2 (7), D3 (9), and E2 (12) have been determined on the basis of chemical and physicochemical evidence.

  Glycyrrhizae Radix, Glycyrrhiza uralensis, licorice-saponin A3, licorice-saponin B2, licorice-saponin C2, licorice-saponin D3, licorice-saponin E2, oleanene-type triterpene oligoglycoside

  Publication DOI: 10.1248/cpb.36.3710
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Osaka, japan
  Methods: 13C NMR, IR, methanolysis, HPLC, methylation analysis, reverse-phase silica gel CC
  
   
  
  Glycyrrhiza uralensis
  CSDB ID 119496 (all data & tools)
• Article ID: 10006
  Kitagawa I, Zhou JL, Sakagami M, Uchida E, Yoshikawa M "Licorice-saponins F3, G2, H2, J2, and K2, five new oleanene- triterpene oligoglycosides from the root of Glycyrrhiza uralensis" - Chemical and Pharmaceutical Bulletin 39(1) (1991) 244-246
  

  Following the structure elucidation of licorice-saponins A3,B2,C2,D3,and E2,the structures of five more new oleanene-triterpene oligoglycosides named licorice-saponins F3 (1), G2 (5), H2 (7), J2 (10), and K2 (12), concomitantly isolated from the root of Glycyrrhiza uralensis Fischer= (Tohoku-kanzo in Japanese), have been determined on the basis of chemical and physicochemical evidence. During the process, a facile chemical conversion method from olean-12-ene or olean-12-en-11-one oligoglycosides to an olean-11,13-diene oligoglycoside, has been found.

  Glycyrrhiza uralensis, Glycyrrhiza Radix, licorice-saponin F3, licorice-saponin G2, licorice-saponin H2, licorice-saponin J2, licorice-saponin K2, olean-11, 13-diene olygoglycoside

  Publication DOI: 10.1248/cpb.39.244
  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003628898
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Osaka, japan
  Methods: 13C NMR, 1H NMR, IR, methanolysis, methylation analysis, Fab-MS
  
   
  
  Glycyrrhiza uralensis
  CSDB ID 119724 (all data & tools)
• Article ID: 10381
  Kitagawa I, Kamigauchi T, Ohmori H, Yoshikawa M "Saponin and sapogenol. XXIX. Selective cleavage of the glucuronide linkage in oligoglycosides by anodic oxidation" - Chemical and Pharmaceutical Bulletin 28 (1980) 3078-3086
  

  In the course of studies aimed at finding a new selective cleavage method for the glucuronide linkage in glucuronide-saponins, an electrolytic oxidation reaction has been found to be useful as an initial reaction for the desired selective cleavage method. The new cleavage method comprises an anodic oxidation of glucuronide-saponin, by which the carboxyl function is converted to an acetoxyl moiety, and a subsequent alkali treatment. It has also been found that the anodic oxidation causes selective oxidation of axial hydroxyl groups and allylic oxidation in the sapogenol moiety.

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003662421
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Osaka, japan
  
   
  
  Glycyrrhiza
  CSDB ID 119002 (all data & tools)
• Article ID: 10484
  Kitagawa I, Hori K, Taniyama T, Zhou JL, Yoshikawa M "Saponin and sapogenol. XLVII. On the constituents of the roots of Glycyrrhiza uralensis FISCHER from northeastern China. (1). Licorice- saponins A3, B2, and C2" - Chemical and Pharmaceutical Bulletin 41 (1993) 43-49
  

  From the air-dried root of Glycyrrhiza uralensis, collected in the northeastern part of China, ten new oleanane-type triterpene oligoglycosides were isolated together with glycyrrhizin (1) and several known flavonoids. Among the newly isolated triterpene oligoglycosides, the chemical structures of licorice-saponin A3 (2), licorice-saponin B2 (3), and licorice-saponin C2 (4) have been determined, on the basis of chemical and physicochemical evidence, to be expressed as 30-O-β-D-glucopyranosylglycyrrhizm, 11-deoxo-glycyrrhizin, and 3-O-[β-D-glucuronopyranosyl(1→2)-β-D-glucuronopyranosyl]oleana-11,13(18)-dien-30-oic acid, respectively. During the course of these studies, facile conversions from glycyrrhizn (1) to licorice-saponins A3 (2), B2 (3), and C2 (4) have been accomplished.

  glycyrrhizin, Glycyrrhizae Radix, Glycyrrhiza uralensis, Leguminosae, oleanane-type triterpene oligoglycoside, licorice-saponin

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003630278
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Osaka, japan
  Methods: 13C NMR, 1H NMR, gel filtration, IR, FAB-MS, methanolysis, HPLC, alkaline hydrolysis, methylation analysis, reduction
  
   
  
  Glycyrrhiza uralensis
  CSDB ID 120111 (all data & tools)
• Article ID: 10548
  Zani F, Cuzzoni MT, Daglia M, Benvenuti S, Vampa G, Mazza P "Inhibition of mutagenicity in Salmonella typhimurium by Glycyrrhiza glabra extract, glycyrrhizinic acid, 18α- and 18β-glycyrrhetinic acids" - Planta Medica 59 (1993) 502-507
  

  The effects of Glycyrrhiza glabra L. extract, glycyrrhizinic acid, 18α- and 18β-glycyrrhetinic acids on the mutagenicity of the ethyl methanesulfonate, N-methyl-N'-nitro-N-nitrosoguanidine, and ribose-lysine Maillard model systems were investigated by using the Salmonella/microsome reversion assay. The protocol used allowed us to detect desmutagenic and antimutagenic activity and to avoid false positive results due to toxicity. For all the compounds tested, no desmutagenic activity was observed against ethyl methanesulfonate and N-methyl-N'-nitro-N-nitrosoguanidine; only Glycyrrhiza glabra extract showed antimutagenic activity against ethyl methanesulfonate. On using the ribose-lysine mutagenic browning mixture, the desmutagenic activities of the Glycyrrhiza glabra extract, glycyrrhizinic acid, 18α- and 18β-glycyrrhetinic acids were observed. 18β-Glycyrrhetinic acid was the most active compound. Glycyrrhiza glabra extract also exhibited antimutagenic activity against ribose-lysine.

  NCBI PubMed ID: 8302947
  Publication DOI: 10.1055/s-2006-959748
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Institutions: Dipartimento Farmaceutico, Facoltà di Farmacia, Università di Parma, Italy
  
   
  
  Glycyrrhiza glabra
  CSDB ID 147289 (all data & tools)
• Article ID: 10552
  Kitagawa I, Hori K, Sakagami M, Zhou JL, Yoshikawa M "Saponin and sapogenol. XLVIII. On the constituents of the roots of Glycyrrhiza uralensis FISCHER from northeastern China. (2). Licorice- saponins D3, E2, F3, G2, H2, J2, and K2" - Chemical and Pharmaceutical Bulletin 41 (1993) 1337-1345
  

  Following the characterization of licorice-saponins A3 (2), B2 (3), and C2 (4), the chemical structures of licorice-saponins D3 (5), E2 (6), F3 (7), G2 (8), H2 (9), J2 (10), and K2 (11), seven of the ten oleanane-type triterpene oligoglycosides isolated from the air-dried roots of Glycyrrhiza uralensis FISCHER collected in the northeastern part of China, were investigated. On the basis of chemical and physicochemical evidence, the structures of licorice-saponins D3,E2,F3,G2,H2,J2,and K2 have been determined to be expressed as 3β-[α-L-rhamnopyranosyl(1→2)-β-D-glucuronopyranosyl(1→2)-β-D-glucuronopyranosyloxy]-22β-acetoxyolean-12-en-30-oic acid (5), 3-O-[β-D-glucuronopyranosyl(1→2)-β-D-glucuronopyranosyl]glabrolide (6), 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl]-11-deoxoglabrolide (7), 24-hydroxyglycyrrhizin (8), 3-O-[β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl]liquiritic acid (9), 24-hydroxy-11-deoxoglycyrrhizin (10), and 3β-[β-D-glucuronopyranosyl(1→2)-β-D-glucuronopyranosyloxy]-24-hydroxyoleana-11,13(18)-dien-30-oic acid (11), respectively.

  Glycyrrhizae Radix, Glycyrrhiza uralensis, Leguminosae, oleanane-type triterpene oligoglycoside, licorice-saponin

  NCBI PubMed ID: 8403082
  Publication DOI: 10.1248/cpb.41.1337
  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003630619
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Japan
  Methods: 13C NMR, 1H NMR, EI-MS, IR, TLC, acid hydrolysis, GLC, methanolysis, alkaline hydrolysis, methylation analysis, reduction, acetylation analysis
  
   
  
  Glycyrrhiza uralensis
  CSDB ID 120179 (all data & tools)
• Article ID: 10553
  Kitagawa I, Hori K, Sakagami M, Hashiuchi F, Yoshikawa M, Ren J "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" - Chemical and Pharmaceutical Bulletin 41 (1993) 1350-1357
  

  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.

  Glycyrrhizae Radix, oleanane-type triterpene oligoglycoside, Glycyrrhiza inflata, apioglycyrrhizin, diazomethane methylation unusual

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003630621
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Japan, Xinjiang Institute of Chemistry, Academia Sinica, China
  Methods: 13C NMR, 1H NMR, gel filtration, IR, methanolysis, alkaline hydrolysis, methylation analysis, reduction, SI-MS, acetylation analysis
  
   
  
  Glycyrrhiza inflata
  CSDB ID 270190 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_423153

• Article ID: 9743
  Kitagawa I, Zhou JL, Sakagami M, Taniyama T, Yoshikawa M "Licorice-saponins A3, B2, C2, D3, and E2, five new oleanene-type triterpene oligoglycosides from Chinese Glycyrrhizae radix" - Chemical and Pharmaceutical Bulletin 36(9) (1988) 3710-3713
  

  Ten new oleanene-type triterpene oligoglycosides were isolated from Chinese Glycyrrhizae Radix, the dried root of Glycyrrhiza uralensis Fischer [Tohoku-Kanzo (in japanese) from China], and the structures of five olygoglycosides, named licorice-saponins A3 (3), B2 (5), C2 (7), D3 (9), and E2 (12) have been determined on the basis of chemical and physicochemical evidence.

  Glycyrrhizae Radix, Glycyrrhiza uralensis, licorice-saponin A3, licorice-saponin B2, licorice-saponin C2, licorice-saponin D3, licorice-saponin E2, oleanene-type triterpene oligoglycoside

  Publication DOI: 10.1248/cpb.36.3710
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Osaka, japan
  Methods: 13C NMR, IR, methanolysis, HPLC, methylation analysis, reverse-phase silica gel CC
  
   
  
  Glycyrrhiza uralensis
  CSDB ID 219496 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_423153

• Article ID: 9743
  Kitagawa I, Zhou JL, Sakagami M, Taniyama T, Yoshikawa M "Licorice-saponins A3, B2, C2, D3, and E2, five new oleanene-type triterpene oligoglycosides from Chinese Glycyrrhizae radix" - Chemical and Pharmaceutical Bulletin 36(9) (1988) 3710-3713
  

  Ten new oleanene-type triterpene oligoglycosides were isolated from Chinese Glycyrrhizae Radix, the dried root of Glycyrrhiza uralensis Fischer [Tohoku-Kanzo (in japanese) from China], and the structures of five olygoglycosides, named licorice-saponins A3 (3), B2 (5), C2 (7), D3 (9), and E2 (12) have been determined on the basis of chemical and physicochemical evidence.

  Glycyrrhizae Radix, Glycyrrhiza uralensis, licorice-saponin A3, licorice-saponin B2, licorice-saponin C2, licorice-saponin D3, licorice-saponin E2, oleanene-type triterpene oligoglycoside

  Publication DOI: 10.1248/cpb.36.3710
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Osaka, japan
  Methods: 13C NMR, IR, methanolysis, HPLC, methylation analysis, reverse-phase silica gel CC
  
   
  
  Glycyrrhiza uralensis
  CSDB ID 269496 (all data & tools)

Show legend Show as text

Structure type: oligomer
C₄₈H₇₂H₂₁
Trivial name: licorice-saponin A3
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_423153,IEDB_983931,SB_192

• Article ID: 9743
  Kitagawa I, Zhou JL, Sakagami M, Taniyama T, Yoshikawa M "Licorice-saponins A3, B2, C2, D3, and E2, five new oleanene-type triterpene oligoglycosides from Chinese Glycyrrhizae radix" - Chemical and Pharmaceutical Bulletin 36(9) (1988) 3710-3713
  

  Ten new oleanene-type triterpene oligoglycosides were isolated from Chinese Glycyrrhizae Radix, the dried root of Glycyrrhiza uralensis Fischer [Tohoku-Kanzo (in japanese) from China], and the structures of five olygoglycosides, named licorice-saponins A3 (3), B2 (5), C2 (7), D3 (9), and E2 (12) have been determined on the basis of chemical and physicochemical evidence.

  Glycyrrhizae Radix, Glycyrrhiza uralensis, licorice-saponin A3, licorice-saponin B2, licorice-saponin C2, licorice-saponin D3, licorice-saponin E2, oleanene-type triterpene oligoglycoside

  Publication DOI: 10.1248/cpb.36.3710
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Osaka, japan
  Methods: 13C NMR, IR, methanolysis, HPLC, methylation analysis, reverse-phase silica gel CC
  
   
  
  Glycyrrhiza uralensis
  CSDB ID 119497 (all data & tools)
• Article ID: 10484
  Kitagawa I, Hori K, Taniyama T, Zhou JL, Yoshikawa M "Saponin and sapogenol. XLVII. On the constituents of the roots of Glycyrrhiza uralensis FISCHER from northeastern China. (1). Licorice- saponins A3, B2, and C2" - Chemical and Pharmaceutical Bulletin 41 (1993) 43-49
  

  From the air-dried root of Glycyrrhiza uralensis, collected in the northeastern part of China, ten new oleanane-type triterpene oligoglycosides were isolated together with glycyrrhizin (1) and several known flavonoids. Among the newly isolated triterpene oligoglycosides, the chemical structures of licorice-saponin A3 (2), licorice-saponin B2 (3), and licorice-saponin C2 (4) have been determined, on the basis of chemical and physicochemical evidence, to be expressed as 30-O-β-D-glucopyranosylglycyrrhizm, 11-deoxo-glycyrrhizin, and 3-O-[β-D-glucuronopyranosyl(1→2)-β-D-glucuronopyranosyl]oleana-11,13(18)-dien-30-oic acid, respectively. During the course of these studies, facile conversions from glycyrrhizn (1) to licorice-saponins A3 (2), B2 (3), and C2 (4) have been accomplished.

  glycyrrhizin, Glycyrrhizae Radix, Glycyrrhiza uralensis, Leguminosae, oleanane-type triterpene oligoglycoside, licorice-saponin

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003630278
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Osaka, japan
  Methods: 13C NMR, 1H NMR, gel filtration, IR, FAB-MS, methanolysis, HPLC, alkaline hydrolysis, methylation analysis, reduction
  
   
  
  Glycyrrhiza uralensis
  CSDB ID 120112 (all data & tools)
• Article ID: 10552
  Kitagawa I, Hori K, Sakagami M, Zhou JL, Yoshikawa M "Saponin and sapogenol. XLVIII. On the constituents of the roots of Glycyrrhiza uralensis FISCHER from northeastern China. (2). Licorice- saponins D3, E2, F3, G2, H2, J2, and K2" - Chemical and Pharmaceutical Bulletin 41 (1993) 1337-1345
  

  Following the characterization of licorice-saponins A3 (2), B2 (3), and C2 (4), the chemical structures of licorice-saponins D3 (5), E2 (6), F3 (7), G2 (8), H2 (9), J2 (10), and K2 (11), seven of the ten oleanane-type triterpene oligoglycosides isolated from the air-dried roots of Glycyrrhiza uralensis FISCHER collected in the northeastern part of China, were investigated. On the basis of chemical and physicochemical evidence, the structures of licorice-saponins D3,E2,F3,G2,H2,J2,and K2 have been determined to be expressed as 3β-[α-L-rhamnopyranosyl(1→2)-β-D-glucuronopyranosyl(1→2)-β-D-glucuronopyranosyloxy]-22β-acetoxyolean-12-en-30-oic acid (5), 3-O-[β-D-glucuronopyranosyl(1→2)-β-D-glucuronopyranosyl]glabrolide (6), 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl]-11-deoxoglabrolide (7), 24-hydroxyglycyrrhizin (8), 3-O-[β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl]liquiritic acid (9), 24-hydroxy-11-deoxoglycyrrhizin (10), and 3β-[β-D-glucuronopyranosyl(1→2)-β-D-glucuronopyranosyloxy]-24-hydroxyoleana-11,13(18)-dien-30-oic acid (11), respectively.

  Glycyrrhizae Radix, Glycyrrhiza uralensis, Leguminosae, oleanane-type triterpene oligoglycoside, licorice-saponin

  NCBI PubMed ID: 8403082
  Publication DOI: 10.1248/cpb.41.1337
  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003630619
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Japan
  Methods: 13C NMR, 1H NMR, EI-MS, IR, TLC, acid hydrolysis, GLC, methanolysis, alkaline hydrolysis, methylation analysis, reduction, acetylation analysis
  
   
  
  Glycyrrhiza uralensis
  CSDB ID 120180 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_423153,IEDB_983931,SB_192

• Article ID: 9743
  Kitagawa I, Zhou JL, Sakagami M, Taniyama T, Yoshikawa M "Licorice-saponins A3, B2, C2, D3, and E2, five new oleanene-type triterpene oligoglycosides from Chinese Glycyrrhizae radix" - Chemical and Pharmaceutical Bulletin 36(9) (1988) 3710-3713
  

  Ten new oleanene-type triterpene oligoglycosides were isolated from Chinese Glycyrrhizae Radix, the dried root of Glycyrrhiza uralensis Fischer [Tohoku-Kanzo (in japanese) from China], and the structures of five olygoglycosides, named licorice-saponins A3 (3), B2 (5), C2 (7), D3 (9), and E2 (12) have been determined on the basis of chemical and physicochemical evidence.

  Glycyrrhizae Radix, Glycyrrhiza uralensis, licorice-saponin A3, licorice-saponin B2, licorice-saponin C2, licorice-saponin D3, licorice-saponin E2, oleanene-type triterpene oligoglycoside

  Publication DOI: 10.1248/cpb.36.3710
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Osaka, japan
  Methods: 13C NMR, IR, methanolysis, HPLC, methylation analysis, reverse-phase silica gel CC
  
   
  
  Glycyrrhiza uralensis
  CSDB ID 269497 (all data & tools)
• Article ID: 10484
  Kitagawa I, Hori K, Taniyama T, Zhou JL, Yoshikawa M "Saponin and sapogenol. XLVII. On the constituents of the roots of Glycyrrhiza uralensis FISCHER from northeastern China. (1). Licorice- saponins A3, B2, and C2" - Chemical and Pharmaceutical Bulletin 41 (1993) 43-49
  

  From the air-dried root of Glycyrrhiza uralensis, collected in the northeastern part of China, ten new oleanane-type triterpene oligoglycosides were isolated together with glycyrrhizin (1) and several known flavonoids. Among the newly isolated triterpene oligoglycosides, the chemical structures of licorice-saponin A3 (2), licorice-saponin B2 (3), and licorice-saponin C2 (4) have been determined, on the basis of chemical and physicochemical evidence, to be expressed as 30-O-β-D-glucopyranosylglycyrrhizm, 11-deoxo-glycyrrhizin, and 3-O-[β-D-glucuronopyranosyl(1→2)-β-D-glucuronopyranosyl]oleana-11,13(18)-dien-30-oic acid, respectively. During the course of these studies, facile conversions from glycyrrhizn (1) to licorice-saponins A3 (2), B2 (3), and C2 (4) have been accomplished.

  glycyrrhizin, Glycyrrhizae Radix, Glycyrrhiza uralensis, Leguminosae, oleanane-type triterpene oligoglycoside, licorice-saponin

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003630278
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Osaka, japan
  Methods: 13C NMR, 1H NMR, gel filtration, IR, FAB-MS, methanolysis, HPLC, alkaline hydrolysis, methylation analysis, reduction
  
   
  
  Glycyrrhiza uralensis
  CSDB ID 270111 (all data & tools)
• Article ID: 10552
  Kitagawa I, Hori K, Sakagami M, Zhou JL, Yoshikawa M "Saponin and sapogenol. XLVIII. On the constituents of the roots of Glycyrrhiza uralensis FISCHER from northeastern China. (2). Licorice- saponins D3, E2, F3, G2, H2, J2, and K2" - Chemical and Pharmaceutical Bulletin 41 (1993) 1337-1345
  

  Following the characterization of licorice-saponins A3 (2), B2 (3), and C2 (4), the chemical structures of licorice-saponins D3 (5), E2 (6), F3 (7), G2 (8), H2 (9), J2 (10), and K2 (11), seven of the ten oleanane-type triterpene oligoglycosides isolated from the air-dried roots of Glycyrrhiza uralensis FISCHER collected in the northeastern part of China, were investigated. On the basis of chemical and physicochemical evidence, the structures of licorice-saponins D3,E2,F3,G2,H2,J2,and K2 have been determined to be expressed as 3β-[α-L-rhamnopyranosyl(1→2)-β-D-glucuronopyranosyl(1→2)-β-D-glucuronopyranosyloxy]-22β-acetoxyolean-12-en-30-oic acid (5), 3-O-[β-D-glucuronopyranosyl(1→2)-β-D-glucuronopyranosyl]glabrolide (6), 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl]-11-deoxoglabrolide (7), 24-hydroxyglycyrrhizin (8), 3-O-[β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl]liquiritic acid (9), 24-hydroxy-11-deoxoglycyrrhizin (10), and 3β-[β-D-glucuronopyranosyl(1→2)-β-D-glucuronopyranosyloxy]-24-hydroxyoleana-11,13(18)-dien-30-oic acid (11), respectively.

  Glycyrrhizae Radix, Glycyrrhiza uralensis, Leguminosae, oleanane-type triterpene oligoglycoside, licorice-saponin

  NCBI PubMed ID: 8403082
  Publication DOI: 10.1248/cpb.41.1337
  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003630619
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Japan
  Methods: 13C NMR, 1H NMR, EI-MS, IR, TLC, acid hydrolysis, GLC, methanolysis, alkaline hydrolysis, methylation analysis, reduction, acetylation analysis
  
   
  
  Glycyrrhiza uralensis
  CSDB ID 270179 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 9743
  Kitagawa I, Zhou JL, Sakagami M, Taniyama T, Yoshikawa M "Licorice-saponins A3, B2, C2, D3, and E2, five new oleanene-type triterpene oligoglycosides from Chinese Glycyrrhizae radix" - Chemical and Pharmaceutical Bulletin 36(9) (1988) 3710-3713
  

  Ten new oleanene-type triterpene oligoglycosides were isolated from Chinese Glycyrrhizae Radix, the dried root of Glycyrrhiza uralensis Fischer [Tohoku-Kanzo (in japanese) from China], and the structures of five olygoglycosides, named licorice-saponins A3 (3), B2 (5), C2 (7), D3 (9), and E2 (12) have been determined on the basis of chemical and physicochemical evidence.

  Glycyrrhizae Radix, Glycyrrhiza uralensis, licorice-saponin A3, licorice-saponin B2, licorice-saponin C2, licorice-saponin D3, licorice-saponin E2, oleanene-type triterpene oligoglycoside

  Publication DOI: 10.1248/cpb.36.3710
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Osaka, japan
  Methods: 13C NMR, IR, methanolysis, HPLC, methylation analysis, reverse-phase silica gel CC
  
   
  
  Glycyrrhiza uralensis
  CSDB ID 269498 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_423153,IEDB_983931,SB_192,SB_61

• Article ID: 9743
  Kitagawa I, Zhou JL, Sakagami M, Taniyama T, Yoshikawa M "Licorice-saponins A3, B2, C2, D3, and E2, five new oleanene-type triterpene oligoglycosides from Chinese Glycyrrhizae radix" - Chemical and Pharmaceutical Bulletin 36(9) (1988) 3710-3713
  

  Ten new oleanene-type triterpene oligoglycosides were isolated from Chinese Glycyrrhizae Radix, the dried root of Glycyrrhiza uralensis Fischer [Tohoku-Kanzo (in japanese) from China], and the structures of five olygoglycosides, named licorice-saponins A3 (3), B2 (5), C2 (7), D3 (9), and E2 (12) have been determined on the basis of chemical and physicochemical evidence.

  Glycyrrhizae Radix, Glycyrrhiza uralensis, licorice-saponin A3, licorice-saponin B2, licorice-saponin C2, licorice-saponin D3, licorice-saponin E2, oleanene-type triterpene oligoglycoside

  Publication DOI: 10.1248/cpb.36.3710
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Osaka, japan
  Methods: 13C NMR, IR, methanolysis, HPLC, methylation analysis, reverse-phase silica gel CC
  
   
  
  Glycyrrhiza uralensis
  CSDB ID 269499 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_423153

• Article ID: 10484
  Kitagawa I, Hori K, Taniyama T, Zhou JL, Yoshikawa M "Saponin and sapogenol. XLVII. On the constituents of the roots of Glycyrrhiza uralensis FISCHER from northeastern China. (1). Licorice- saponins A3, B2, and C2" - Chemical and Pharmaceutical Bulletin 41 (1993) 43-49
  

  From the air-dried root of Glycyrrhiza uralensis, collected in the northeastern part of China, ten new oleanane-type triterpene oligoglycosides were isolated together with glycyrrhizin (1) and several known flavonoids. Among the newly isolated triterpene oligoglycosides, the chemical structures of licorice-saponin A3 (2), licorice-saponin B2 (3), and licorice-saponin C2 (4) have been determined, on the basis of chemical and physicochemical evidence, to be expressed as 30-O-β-D-glucopyranosylglycyrrhizm, 11-deoxo-glycyrrhizin, and 3-O-[β-D-glucuronopyranosyl(1→2)-β-D-glucuronopyranosyl]oleana-11,13(18)-dien-30-oic acid, respectively. During the course of these studies, facile conversions from glycyrrhizn (1) to licorice-saponins A3 (2), B2 (3), and C2 (4) have been accomplished.

  glycyrrhizin, Glycyrrhizae Radix, Glycyrrhiza uralensis, Leguminosae, oleanane-type triterpene oligoglycoside, licorice-saponin

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003630278
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Osaka, japan
  Methods: 13C NMR, 1H NMR, gel filtration, IR, FAB-MS, methanolysis, HPLC, alkaline hydrolysis, methylation analysis, reduction
  
   
  
  Glycyrrhiza uralensis
  CSDB ID 220111 (all data & tools)
• Article ID: 10552
  Kitagawa I, Hori K, Sakagami M, Zhou JL, Yoshikawa M "Saponin and sapogenol. XLVIII. On the constituents of the roots of Glycyrrhiza uralensis FISCHER from northeastern China. (2). Licorice- saponins D3, E2, F3, G2, H2, J2, and K2" - Chemical and Pharmaceutical Bulletin 41 (1993) 1337-1345
  

  Following the characterization of licorice-saponins A3 (2), B2 (3), and C2 (4), the chemical structures of licorice-saponins D3 (5), E2 (6), F3 (7), G2 (8), H2 (9), J2 (10), and K2 (11), seven of the ten oleanane-type triterpene oligoglycosides isolated from the air-dried roots of Glycyrrhiza uralensis FISCHER collected in the northeastern part of China, were investigated. On the basis of chemical and physicochemical evidence, the structures of licorice-saponins D3,E2,F3,G2,H2,J2,and K2 have been determined to be expressed as 3β-[α-L-rhamnopyranosyl(1→2)-β-D-glucuronopyranosyl(1→2)-β-D-glucuronopyranosyloxy]-22β-acetoxyolean-12-en-30-oic acid (5), 3-O-[β-D-glucuronopyranosyl(1→2)-β-D-glucuronopyranosyl]glabrolide (6), 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl]-11-deoxoglabrolide (7), 24-hydroxyglycyrrhizin (8), 3-O-[β-D-glucuronopyranosyl-(1→2)-β-D-glucuronopyranosyl]liquiritic acid (9), 24-hydroxy-11-deoxoglycyrrhizin (10), and 3β-[β-D-glucuronopyranosyl(1→2)-β-D-glucuronopyranosyloxy]-24-hydroxyoleana-11,13(18)-dien-30-oic acid (11), respectively.

  Glycyrrhizae Radix, Glycyrrhiza uralensis, Leguminosae, oleanane-type triterpene oligoglycoside, licorice-saponin

  NCBI PubMed ID: 8403082
  Publication DOI: 10.1248/cpb.41.1337
  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003630619
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Japan
  Methods: 13C NMR, 1H NMR, EI-MS, IR, TLC, acid hydrolysis, GLC, methanolysis, alkaline hydrolysis, methylation analysis, reduction, acetylation analysis
  
   
  
  Glycyrrhiza uralensis
  CSDB ID 220179 (all data & tools)
• Article ID: 10553
  Kitagawa I, Hori K, Sakagami M, Hashiuchi F, Yoshikawa M, Ren J "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" - Chemical and Pharmaceutical Bulletin 41 (1993) 1350-1357
  

  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.

  Glycyrrhizae Radix, oleanane-type triterpene oligoglycoside, Glycyrrhiza inflata, apioglycyrrhizin, diazomethane methylation unusual

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003630621
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Japan, Xinjiang Institute of Chemistry, Academia Sinica, China
  Methods: 13C NMR, 1H NMR, gel filtration, IR, methanolysis, alkaline hydrolysis, methylation analysis, reduction, SI-MS, acetylation analysis
  
   
  
  Glycyrrhiza inflata
  CSDB ID 270195 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_115136,IEDB_140629,IEDB_140630,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_423153,IEDB_983931,SB_192

• Article ID: 10497
  Mizutani K, Kuramoto T, Tamura Y, Ohtake N, Doi S, Nakaura M, Tanaka O "Sweetness of glycyrrhetic acid 3-O-β-D-monoglucuronide and the related glycosides" - Bioscience, Biotechnology, and Biochemistry 58 (1994) 554-555
  

  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-β-D-xyloside and the 3-O-β-D-glucuronide (MGGR). Especially, MGGR had a high sweetness relative to sucrose; x941, and would appear to be a new potent sweetener.

  NCBI PubMed ID: 7764694
  Journal NLM ID: 9205717
  Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry
  Institutions: Research Laboratories, Maruzen Pharmaceuticals Co., Ltd., Hiroshima, Japan
  
   
  
  Glycyrrhiza
  CSDB ID 111287 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_423153,IEDB_983931,SB_192

• Article ID: 10497
  Mizutani K, Kuramoto T, Tamura Y, Ohtake N, Doi S, Nakaura M, Tanaka O "Sweetness of glycyrrhetic acid 3-O-β-D-monoglucuronide and the related glycosides" - Bioscience, Biotechnology, and Biochemistry 58 (1994) 554-555
  

  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-β-D-xyloside and the 3-O-β-D-glucuronide (MGGR). Especially, MGGR had a high sweetness relative to sucrose; x941, and would appear to be a new potent sweetener.

  NCBI PubMed ID: 7764694
  Journal NLM ID: 9205717
  Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry
  Institutions: Research Laboratories, Maruzen Pharmaceuticals Co., Ltd., Hiroshima, Japan
  
   
  
  Glycyrrhiza
  CSDB ID 111288 (all data & tools)

Show legend Show as text

Structure type: oligomer
C₄₁H₆₄O₁₄
Trivial name: apioglycyrrhizin
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_423153

• Article ID: 10553
  Kitagawa I, Hori K, Sakagami M, Hashiuchi F, Yoshikawa M, Ren J "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" - Chemical and Pharmaceutical Bulletin 41 (1993) 1350-1357
  

  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.

  Glycyrrhizae Radix, oleanane-type triterpene oligoglycoside, Glycyrrhiza inflata, apioglycyrrhizin, diazomethane methylation unusual

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003630621
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Japan, Xinjiang Institute of Chemistry, Academia Sinica, China
  Methods: 13C NMR, 1H NMR, gel filtration, IR, methanolysis, alkaline hydrolysis, methylation analysis, reduction, SI-MS, acetylation analysis
  
   
  
  Glycyrrhiza inflata
  CSDB ID 120190 (all data & tools)

Show legend Show as text

Structure type: oligomer
C₄₃H₆₆O₁₄
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_423153

• Article ID: 10553
  Kitagawa I, Hori K, Sakagami M, Hashiuchi F, Yoshikawa M, Ren J "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" - Chemical and Pharmaceutical Bulletin 41 (1993) 1350-1357
  

  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.

  Glycyrrhizae Radix, oleanane-type triterpene oligoglycoside, Glycyrrhiza inflata, apioglycyrrhizin, diazomethane methylation unusual

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003630621
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Japan, Xinjiang Institute of Chemistry, Academia Sinica, China
  Methods: 13C NMR, 1H NMR, gel filtration, IR, methanolysis, alkaline hydrolysis, methylation analysis, reduction, SI-MS, acetylation analysis
  
   
  
  Glycyrrhiza inflata
  CSDB ID 270191 (all data & tools)

Show legend Show as text

Structure type: oligomer
C₄₂H₆₆O₁₃
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 10553
  Kitagawa I, Hori K, Sakagami M, Hashiuchi F, Yoshikawa M, Ren J "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" - Chemical and Pharmaceutical Bulletin 41 (1993) 1350-1357
  

  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.

  Glycyrrhizae Radix, oleanane-type triterpene oligoglycoside, Glycyrrhiza inflata, apioglycyrrhizin, diazomethane methylation unusual

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003630621
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Japan, Xinjiang Institute of Chemistry, Academia Sinica, China
  Methods: 13C NMR, 1H NMR, gel filtration, IR, methanolysis, alkaline hydrolysis, methylation analysis, reduction, SI-MS, acetylation analysis
  
   
  
  Glycyrrhiza inflata
  CSDB ID 270192 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 821 [M+H]+
C₄₄H₆₈O₁₄
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_423153

• Article ID: 10553
  Kitagawa I, Hori K, Sakagami M, Hashiuchi F, Yoshikawa M, Ren J "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" - Chemical and Pharmaceutical Bulletin 41 (1993) 1350-1357
  

  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.

  Glycyrrhizae Radix, oleanane-type triterpene oligoglycoside, Glycyrrhiza inflata, apioglycyrrhizin, diazomethane methylation unusual

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003630621
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Japan, Xinjiang Institute of Chemistry, Academia Sinica, China
  Methods: 13C NMR, 1H NMR, gel filtration, IR, methanolysis, alkaline hydrolysis, methylation analysis, reduction, SI-MS, acetylation analysis
  
   
  
  Glycyrrhiza inflata
  CSDB ID 270198 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 821 [M+H]+
C₄₄H₆₈O₁₄
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_423153

• Article ID: 10553
  Kitagawa I, Hori K, Sakagami M, Hashiuchi F, Yoshikawa M, Ren J "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" - Chemical and Pharmaceutical Bulletin 41 (1993) 1350-1357
  

  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.

  Glycyrrhizae Radix, oleanane-type triterpene oligoglycoside, Glycyrrhiza inflata, apioglycyrrhizin, diazomethane methylation unusual

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003630621
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Japan, Xinjiang Institute of Chemistry, Academia Sinica, China
  Methods: 13C NMR, 1H NMR, gel filtration, IR, methanolysis, alkaline hydrolysis, methylation analysis, reduction, SI-MS, acetylation analysis
  
   
  
  Glycyrrhiza inflata
  CSDB ID 270199 (all data & tools)