Show legend Show as text

Structure type: oligomer ; 663.7804 [M+H]+, 661 [M-H]-
C₃₂H₅₄O₁₄
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 7993
  Rezanka T, Guschina IA "Glycosidic compounds of murolic, protoconstipatic and allo-murolic acids from lichens of Central Asia" - Phytochemistry 54(6) (2000) 635-645
  

  Eleven compounds isolated from the extract of the Central Asian lichens comprised eight new glycosides having murolic, protoconstipatic and allo-murolic acids, as the aglycones and a saccharide moiety linked at C-18 made up of one or two sugars (glucose and apiose or rhamnose or xylose or arabinose). The structures were elucidated by using extensive spectroscopic analysis (1D and 2D NMR, MS, IR, UV and CD) and chemical methods.

  glycosides, lichens, murolic acid, glucore, Central Asia, aglycones

  NCBI PubMed ID: 10963458
  Publication DOI: 10.1016/S0031-9422(00)00147-3
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Correspondence: rezanka@biomed.cas.cz
  Institutions: Institute of Microbiology, Academy of Sciences of Czech Republic, Prague, Czech Republic, Institute of Ecology of the Volga River Basin of the Russian Academy of Sciences, Togliatti, Russia
  Methods: 13C NMR, 1H NMR, gel filtration, IR, FAB-MS, TLC, acid hydrolysis, GC, HPLC, UV, extraction, optical rotation measurement, CD, melting point determination, enzymatic assay, HR-FAB-MS, LR-FAB-MS
  
   
  
  Leptogium saturninum, Peltigera canina
  CSDB ID 45486 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 663.7806 [M+H]+, 661 [M-H]-
C₃₂H₅₄O₁₄
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 7993
  Rezanka T, Guschina IA "Glycosidic compounds of murolic, protoconstipatic and allo-murolic acids from lichens of Central Asia" - Phytochemistry 54(6) (2000) 635-645
  

  Eleven compounds isolated from the extract of the Central Asian lichens comprised eight new glycosides having murolic, protoconstipatic and allo-murolic acids, as the aglycones and a saccharide moiety linked at C-18 made up of one or two sugars (glucose and apiose or rhamnose or xylose or arabinose). The structures were elucidated by using extensive spectroscopic analysis (1D and 2D NMR, MS, IR, UV and CD) and chemical methods.

  glycosides, lichens, murolic acid, glucore, Central Asia, aglycones

  NCBI PubMed ID: 10963458
  Publication DOI: 10.1016/S0031-9422(00)00147-3
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Correspondence: rezanka@biomed.cas.cz
  Institutions: Institute of Microbiology, Academy of Sciences of Czech Republic, Prague, Czech Republic, Institute of Ecology of the Volga River Basin of the Russian Academy of Sciences, Togliatti, Russia
  Methods: 13C NMR, 1H NMR, gel filtration, IR, FAB-MS, TLC, acid hydrolysis, GC, HPLC, UV, extraction, optical rotation measurement, CD, melting point determination, enzymatic assay, HR-FAB-MS, LR-FAB-MS
  
   
  
  Cladonia furcata, Lecanora fructulosa, Xanthoparmelia camtschadalis, Xanthoparmelia tinctina
  CSDB ID 45487 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 663.7814 [M+H]+, 661 [M-H]-
C₃₂H₅₄O₁₄
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 7993
  Rezanka T, Guschina IA "Glycosidic compounds of murolic, protoconstipatic and allo-murolic acids from lichens of Central Asia" - Phytochemistry 54(6) (2000) 635-645
  

  Eleven compounds isolated from the extract of the Central Asian lichens comprised eight new glycosides having murolic, protoconstipatic and allo-murolic acids, as the aglycones and a saccharide moiety linked at C-18 made up of one or two sugars (glucose and apiose or rhamnose or xylose or arabinose). The structures were elucidated by using extensive spectroscopic analysis (1D and 2D NMR, MS, IR, UV and CD) and chemical methods.

  glycosides, lichens, murolic acid, glucore, Central Asia, aglycones

  NCBI PubMed ID: 10963458
  Publication DOI: 10.1016/S0031-9422(00)00147-3
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Correspondence: rezanka@biomed.cas.cz
  Institutions: Institute of Microbiology, Academy of Sciences of Czech Republic, Prague, Czech Republic, Institute of Ecology of the Volga River Basin of the Russian Academy of Sciences, Togliatti, Russia
  Methods: 13C NMR, 1H NMR, gel filtration, IR, FAB-MS, TLC, acid hydrolysis, GC, HPLC, UV, extraction, optical rotation measurement, CD, melting point determination, enzymatic assay, HR-FAB-MS, LR-FAB-MS
  
   
  
  Acarospora gobiensis, Xanthoria elegans
  CSDB ID 45488 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 425.1341 [M+Na]+
C₁₈H₂₆O₁₀
Trivial name: icariside F2
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 9147
  Eldin AM, Kamel Z, Hossam N "Purification and identification of surface active amphiphilic candidates produced by Geotrichum candidum MK880487 possessing antifungal property" - Journal of Dispersion Science and Technology 2020 (2020) ID 1813157
  

  The present study was held to optimize production, purify and identify biosurfactant from yeast strain Geotrichum candidum MK880487. Biosurfactant production was done on modified Hua medium and optimized in shake-flask method. Soybean oil (8%, v/v), KNO3 (0.75 g/L) and yeast extract (0.3 g/L) were the best carbon and nitrogen sources, respectively, with C:N ratio of 200:1, pH 8 at 30 °C for 168 h. Production scale-up was achieved on 2.5 L bioreactor as batch method. The resulting crude biosurfactant extract with yield of 1.75 g/L was purified by reversed phase column preparative HPLC. The resulting most active fraction F47 significantly reduced water surface tension by 51.92%. Chemical characterization using TLC, GC-MS, FTIR and LC-MS/MS methods revealed the biosurfactant to contain mainly glycolipid structure existing as mixture of Icariside F2, Cardenolide Di-Hexopyranoside and Di Galactosyl Di Acyl Glycerol glycolipid that collectively showed potential antifungal activity toward Macrophomina phaseolina.

  biosurfactant, LC-MS/MS, biocontrol, Geotrichum candidum

  Publication DOI: 10.1080/01932691.2020.1813157
  Journal NLM ID: 9878574
  Publisher: New York, M. Dekker
  Correspondence: Eldin AM
  Institutions: Department of Soil Microbiology, Soils, Waters and Environmental Research Institute, Agricultural Research Center, Giza, Egypt, Department of Microbiology, Faculty of Science, Cairo University, Giza, Egypt
  Methods: IR, GC-MS, TLC, HPLC, viscosity measurement, extraction, LC-ESI-MS, cell growth, evaporation, centrifugation, antifungal activity test
  
   
  
  Geotrichum candidum MK880487
  CSDB ID 50376 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141794,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88

• Article ID: 9832
  Nakano K, Murakami K, Takaishi Y, Tomimatsu T, Nohara T "Studies on the constituents of Heloniopsis orientalis (Thunb.) C. Tanaka" - Chemical and Pharmaceutical Bulletin 37(1) (1989) 116-118
  

  The constituents of the fresh whole plants of Heloniopsis orientalis (THUNB.) C. TANAKA (Liliaceae) were investigated and five steroidal components were obtained. Their chemical structures were characterized as dioscin (1), pennogenin3-O-β-chacotrioside(T-c)(2), pregnadienolone 3-O-β-chacotrioside(P-d)(3), 26-O-β-D-glucopyranosyl17-dehydrokryptoenin 3-O-β-chacotrioside (4) and 12-O-β-D-galactopyranosyl helonigenin 3-O-β-D-allomethylopyranosyl-(1→5)-β-D-apiofuranoside (5).

  steroidal glycoside, Liliaceae, pennogenin glycoside, Heloniopsis orientalis, dioscin, 17-dehydrokryptogenin glycoside, pregnadienolone glycoside, heloniogenin bisdesmoside, allomethylose, β-chacotrioside

  Publication DOI: 10.1248/cpb.37.116
  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003627245
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Tokushima University, Tokushima, Japan, Faculty of Pharmaceutical Sciences, Kumamoto University, Kumamoto, Japan
  Methods: 13C NMR, 1H NMR, EI-MS, IR, FAB-MS, partial acid hydrolysis, TLC, acid hydrolysis, melting point determination, acetylation analysis
  
   
  
  Heloniopsis orientalis
  CSDB ID 119524 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: 6′-O-apiosyl-ebuloside
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 9993
  Gross GA, Sticher O, Anklin C "New iridoid glycosides and a monoterpene glycoside from Sambucus ebulus L. (Caprifoliaceae)" - Helvetica Chimica Acta 70 (1987) 91-101
  

  From the roots of Sambucus ebulus L., two novel valeriana-type ester iridoid glycosides, 6′-O-apiosylebuloside (1) and 7,7-O-dihydroebuloside (3), along with the open-chain monoterpene glycoside 5 were isolated. Their structure elucidation is based mainly on one- and two-dimensional NMR methods. 1H,1H-COSY experiments permitted complete assignment of signals arising from the disaccharide unit in 1. Biogenetically, 3 seems to represent the equivalent of loganin in the valeriana-type series of iridoid glycosides. (In German.)

  Publication DOI: 10.1002/hlca.19870700111
  Journal NLM ID: 2985094R
  Publisher: Verlag Helvetica Chimica Acta
  Methods: 13C NMR, 1H NMR, IR, acid hydrolysis, MS
  
   
  
  Sambucus ebulus
  CSDB ID 129506 (all data & tools)

Show legend Show as text

Structure type: oligomer
C₂₁H₃₆O₁₁
Trivial name: cis-Linalool 3,7-oxide 6-O-β-D-apiofuranosyl-β-D-glycopyranoside
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 10012
  Moon JH, Watanabe N, Ijima Y, Yagi A, Sakata K "cic-and trans-Linalool 3,7-oxides and methyl salicylate glycosides and (Z)-3-hexenyl β-D-glycopyranoside as aroma precursors from tea leaves for oolong tea" - Bioscience, Biotechnology, and Biochemistry 60 (1996) 1815-1819
  

  Two new alcoholic aroma precursors, cis- and trans-linalool, 3,7-oxides 6-O-β-D-apiofuranosyl-β-D-glucopyranosides (1 and 2), as well as two already known compounds, (Z)-3-hexenyl β-D-glucopyranoside (3) and methyl salicylate 6-O-β-D-xylopyranosyl-β-D-glucopyranoside (β-primeveroside: 4), and another new monoterpendiol glycoside, 8-hydroxygeranyl β-primeveroside (5) have recently been isolated as aroma precursors in tea leaves (Camellia sinensis var. sinensis cv. Maoxie) ready for oolong tea processing.

  oolong tea, aroma precursor, linalool 3, 7-oxides, β-primeveroside, 6-O-β-D-apiofuranosyl-β-D-glucopyranoside

  NCBI PubMed ID: 8987857
  Publication DOI: 10.1271/bbb.60.1815
  Journal NLM ID: 9205717
  Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry
  Institutions: Department of Applied Biological Chemistry, Faculty of Agriculture, Shizuoka University, Japan
  Methods: 13C NMR, 1H NMR, enzymatic hydrolysis, HPLC, HR-FAB-MS
  
   
  
  Camellia sinensis var. sinensis cv. Maoxie
  CSDB ID 111522 (all data & tools)
• Article ID: 12631
  Sakata K "β-Primeverosidase relationship with floral tea aroma formation during processing of oolong tea and black tea" - Book: Caffeinated Beverages (series: ACS Symposium Series, 754) (2000) Vol. 33, 327-336
  

  Flavor is one the most important factors to determine the quality of beverages. Tea aroma, especially floral aroma liberated from brewed oolong tea and black tea, is so attractive. This study covers the molecular basis of the floral aroma formation during the tea processing. Previous work demonstrated the tea aroma precursors of geraniol, linalool, etc. as β-primeverosides (6-Ο-β-D-xylopyranosyl-β-D-glucopyranosides) from the tea leaves (Camellia sinensis var. sinensis cvs. Shuixian and Maoxie) which can be processed to oolong tea. We have also purified β-primeverosidases from fresh leaves of cv. Yabukita for Japanese green tea, cv. Shuixian for oolong tea and a cultivar of C. s. var. assamica for black tea. The molecular weight of each enzyme was shown to be 60,500, 60,200 and 60,300 by TOFMS, respectively. The enzymatic characteristics (optimum temperature, 45 °C; stable temp., 40-45 °C; optimum pH, 4; pH stability, pH 3-5; specific activity, 0.90-0.99 unit/mg) were very similar to each other. The enzyme was confirmed to effectively hydrolyze the aroma precursors, β-primeverosides as well as 6-O-β-D-apiofuranosyl-β-D-glucopyranoside, into disaccharides and each aglycon without further hydrolysis. Most of the alcoholic tea aroma, which contribute to the floral tea aroma, are primarily stored as disaccharide glycosides (β-primeverosides and 6-O-β-D-apiofuranosyl-β-D-glucopyranosides) and generated by the action of a specific enzyme, β-primeverosidase, during the fermentation process of tea manufacturing.

  fermentation, tea, primeverosides, β-primeverosidase

  Publication DOI: 10.1021/bk-2000-0754.ch033
  Publisher: American Chemical Society
  Editors: Parliment TH, Ho C-T, Schieberle P
  Institutions: Institute for Chemical Research, Kyoto University, Uji, Japan
  Methods: enzymatic digestion, CC
  
   
  
  Camellia sinensis var. sinensis cv. Maoxie
  CSDB ID 67561 (all data & tools)

Show legend Show as text

Structure type: oligomer
C₂₁H₃₆O₁₁
Trivial name: trans-Linalool 3,7-oxide 6-O-β-D-apiofuranosyl-β-D-glycopyranoside
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 10012
  Moon JH, Watanabe N, Ijima Y, Yagi A, Sakata K "cic-and trans-Linalool 3,7-oxides and methyl salicylate glycosides and (Z)-3-hexenyl β-D-glycopyranoside as aroma precursors from tea leaves for oolong tea" - Bioscience, Biotechnology, and Biochemistry 60 (1996) 1815-1819
  

  Two new alcoholic aroma precursors, cis- and trans-linalool, 3,7-oxides 6-O-β-D-apiofuranosyl-β-D-glucopyranosides (1 and 2), as well as two already known compounds, (Z)-3-hexenyl β-D-glucopyranoside (3) and methyl salicylate 6-O-β-D-xylopyranosyl-β-D-glucopyranoside (β-primeveroside: 4), and another new monoterpendiol glycoside, 8-hydroxygeranyl β-primeveroside (5) have recently been isolated as aroma precursors in tea leaves (Camellia sinensis var. sinensis cv. Maoxie) ready for oolong tea processing.

  oolong tea, aroma precursor, linalool 3, 7-oxides, β-primeveroside, 6-O-β-D-apiofuranosyl-β-D-glucopyranoside

  NCBI PubMed ID: 8987857
  Publication DOI: 10.1271/bbb.60.1815
  Journal NLM ID: 9205717
  Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry
  Institutions: Department of Applied Biological Chemistry, Faculty of Agriculture, Shizuoka University, Japan
  Methods: 13C NMR, 1H NMR, enzymatic hydrolysis, HPLC, HR-FAB-MS
  
   
  
  Camellia sinensis var. sinensis cv. Maoxie
  CSDB ID 111523 (all data & tools)
• Article ID: 12631
  Sakata K "β-Primeverosidase relationship with floral tea aroma formation during processing of oolong tea and black tea" - Book: Caffeinated Beverages (series: ACS Symposium Series, 754) (2000) Vol. 33, 327-336
  

  Flavor is one the most important factors to determine the quality of beverages. Tea aroma, especially floral aroma liberated from brewed oolong tea and black tea, is so attractive. This study covers the molecular basis of the floral aroma formation during the tea processing. Previous work demonstrated the tea aroma precursors of geraniol, linalool, etc. as β-primeverosides (6-Ο-β-D-xylopyranosyl-β-D-glucopyranosides) from the tea leaves (Camellia sinensis var. sinensis cvs. Shuixian and Maoxie) which can be processed to oolong tea. We have also purified β-primeverosidases from fresh leaves of cv. Yabukita for Japanese green tea, cv. Shuixian for oolong tea and a cultivar of C. s. var. assamica for black tea. The molecular weight of each enzyme was shown to be 60,500, 60,200 and 60,300 by TOFMS, respectively. The enzymatic characteristics (optimum temperature, 45 °C; stable temp., 40-45 °C; optimum pH, 4; pH stability, pH 3-5; specific activity, 0.90-0.99 unit/mg) were very similar to each other. The enzyme was confirmed to effectively hydrolyze the aroma precursors, β-primeverosides as well as 6-O-β-D-apiofuranosyl-β-D-glucopyranoside, into disaccharides and each aglycon without further hydrolysis. Most of the alcoholic tea aroma, which contribute to the floral tea aroma, are primarily stored as disaccharide glycosides (β-primeverosides and 6-O-β-D-apiofuranosyl-β-D-glucopyranosides) and generated by the action of a specific enzyme, β-primeverosidase, during the fermentation process of tea manufacturing.

  fermentation, tea, primeverosides, β-primeverosidase

  Publication DOI: 10.1021/bk-2000-0754.ch033
  Publisher: American Chemical Society
  Editors: Parliment TH, Ho C-T, Schieberle P
  Institutions: Institute for Chemical Research, Kyoto University, Uji, Japan
  Methods: enzymatic digestion, CC
  
   
  
  Camellia sinensis var. sinensis cv. Maoxie
  CSDB ID 67560 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_114701,IEDB_115015,IEDB_115136,IEDB_136045,IEDB_136906,IEDB_137472,IEDB_1394181,IEDB_140630,IEDB_141794,IEDB_142489,IEDB_144562,IEDB_149135,IEDB_151528,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_225177,IEDB_423153,IEDB_885823,SB_7,SB_86

• Article ID: 10073
  Stevenson TT, Darvill AG, Albersheim P "Structure of plant cell walls XXIII. Structural features of the plant cell-wall polysaccharide rhamnogalacturonan-II" - Carbohydrate Research 182 (1988) 207-226
  

  Rhamnogalacturonan-II (RG-II), isolated from the cell walls of suspension-cultured sycamore cells, has been further characterized. End-group analysis of RG-II showed that the polysaccharide contains about 30 glycosyl residues. Some 28 residues have been found as constituents of well characterized oligosaccharide fragments of RG-II. RG-II was treated with lithium metal dissolved in ethylenediamine to degrade the glycosyluronic acid residues. The major product was isolated, characterized, and shown to be the triglycosylalditol α-Xyl-(1→3)-α-Fuc-(1→4)-β-Rha-(1→31)-apiitol. This tetrasaccharide fragment of RG-II has three residues in common with a previously characterized heptasaccharide that had been derived from RG-II by partial hydrolysis with acid. RG-II was found to contain a large number of branched galactosyluronic acid residues that have not yet been identified as components of oligosaccharide fragments, although they are undoubtedly part of an octa(galactosyluronic acid) fragment generated by partial acid hydrolysis. The results of sequential partial acid hydrolysis provided evidence that, in RG-II, the extremely acid-labile 3-deoxy-d-manno-2-octulosonic-acid and 3-deoxy-d-lyxo-2-heptulosaric acid residues are attached to O-3 of 3,4-linked galactosyluronic acid residues, and that the mildly acid-labile apiofuranosyl residues are attached to O-2 of 2,4-linked galactosyluronic acid residues. These and previously published data suggested that RG-II has a highly branched structure, arranged around an α-(1→4)-linked galactosyluronic acid backbone.

  Publication DOI: 10.1016/0008-6215(88)84004-7
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: Complex Carbohydrate Research Center and Department of Biochemistry, University of Georgia, Russell Research Center of the United States Department of Agriculture, Athens, Georgia, U.S.A.
  Methods: 1H NMR, gel filtration, FAB-MS, partial acid hydrolysis, GC-MS, acid hydrolysis
  
   
  
  Acer pseudoplatanus
  CSDB ID 115517 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_136045,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142489,IEDB_144562,IEDB_151528,IEDB_152214,IEDB_153553,IEDB_174333,IEDB_190606,IEDB_225177,IEDB_885823,SB_154,SB_7,SB_86

• Article ID: 10073
  Stevenson TT, Darvill AG, Albersheim P "Structure of plant cell walls XXIII. Structural features of the plant cell-wall polysaccharide rhamnogalacturonan-II" - Carbohydrate Research 182 (1988) 207-226
  

  Rhamnogalacturonan-II (RG-II), isolated from the cell walls of suspension-cultured sycamore cells, has been further characterized. End-group analysis of RG-II showed that the polysaccharide contains about 30 glycosyl residues. Some 28 residues have been found as constituents of well characterized oligosaccharide fragments of RG-II. RG-II was treated with lithium metal dissolved in ethylenediamine to degrade the glycosyluronic acid residues. The major product was isolated, characterized, and shown to be the triglycosylalditol α-Xyl-(1→3)-α-Fuc-(1→4)-β-Rha-(1→31)-apiitol. This tetrasaccharide fragment of RG-II has three residues in common with a previously characterized heptasaccharide that had been derived from RG-II by partial hydrolysis with acid. RG-II was found to contain a large number of branched galactosyluronic acid residues that have not yet been identified as components of oligosaccharide fragments, although they are undoubtedly part of an octa(galactosyluronic acid) fragment generated by partial acid hydrolysis. The results of sequential partial acid hydrolysis provided evidence that, in RG-II, the extremely acid-labile 3-deoxy-d-manno-2-octulosonic-acid and 3-deoxy-d-lyxo-2-heptulosaric acid residues are attached to O-3 of 3,4-linked galactosyluronic acid residues, and that the mildly acid-labile apiofuranosyl residues are attached to O-2 of 2,4-linked galactosyluronic acid residues. These and previously published data suggested that RG-II has a highly branched structure, arranged around an α-(1→4)-linked galactosyluronic acid backbone.

  Publication DOI: 10.1016/0008-6215(88)84004-7
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: Complex Carbohydrate Research Center and Department of Biochemistry, University of Georgia, Russell Research Center of the United States Department of Agriculture, Athens, Georgia, U.S.A.
  Methods: 1H NMR, gel filtration, FAB-MS, partial acid hydrolysis, GC-MS, acid hydrolysis
  
   
  
  Acer pseudoplatanus
  CSDB ID 265517 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_115015,IEDB_115136,IEDB_136045,IEDB_136906,IEDB_137472,IEDB_1394181,IEDB_140630,IEDB_141794,IEDB_142489,IEDB_144562,IEDB_149135,IEDB_151528,IEDB_152214,IEDB_174333,IEDB_190606,IEDB_225177,IEDB_423153,IEDB_885823,SB_7,SB_86

• Article ID: 10073
  Stevenson TT, Darvill AG, Albersheim P "Structure of plant cell walls XXIII. Structural features of the plant cell-wall polysaccharide rhamnogalacturonan-II" - Carbohydrate Research 182 (1988) 207-226
  

  Rhamnogalacturonan-II (RG-II), isolated from the cell walls of suspension-cultured sycamore cells, has been further characterized. End-group analysis of RG-II showed that the polysaccharide contains about 30 glycosyl residues. Some 28 residues have been found as constituents of well characterized oligosaccharide fragments of RG-II. RG-II was treated with lithium metal dissolved in ethylenediamine to degrade the glycosyluronic acid residues. The major product was isolated, characterized, and shown to be the triglycosylalditol α-Xyl-(1→3)-α-Fuc-(1→4)-β-Rha-(1→31)-apiitol. This tetrasaccharide fragment of RG-II has three residues in common with a previously characterized heptasaccharide that had been derived from RG-II by partial hydrolysis with acid. RG-II was found to contain a large number of branched galactosyluronic acid residues that have not yet been identified as components of oligosaccharide fragments, although they are undoubtedly part of an octa(galactosyluronic acid) fragment generated by partial acid hydrolysis. The results of sequential partial acid hydrolysis provided evidence that, in RG-II, the extremely acid-labile 3-deoxy-d-manno-2-octulosonic-acid and 3-deoxy-d-lyxo-2-heptulosaric acid residues are attached to O-3 of 3,4-linked galactosyluronic acid residues, and that the mildly acid-labile apiofuranosyl residues are attached to O-2 of 2,4-linked galactosyluronic acid residues. These and previously published data suggested that RG-II has a highly branched structure, arranged around an α-(1→4)-linked galactosyluronic acid backbone.

  Publication DOI: 10.1016/0008-6215(88)84004-7
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: Complex Carbohydrate Research Center and Department of Biochemistry, University of Georgia, Russell Research Center of the United States Department of Agriculture, Athens, Georgia, U.S.A.
  Methods: 1H NMR, gel filtration, FAB-MS, partial acid hydrolysis, GC-MS, acid hydrolysis
  
   
  
  Acer pseudoplatanus
  CSDB ID 265518 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: canadensissaponin 5
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_167188,IEDB_174332,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88

• Article ID: 10088
  Reznicek G, Jurenitsch J, Freiler M, Korhammer S, Haslinger E, Hiller K, Kubelka W "Isolation and structure elucidation of further new saponins from Solidago canadensis" - Planta Medica 58 (1992) 94-98
  

  Four new main saponins (canadensis-saponins 5-8) (compounds 5-8) were isolated from Solidago canadensis L. (Asteraceae). Using GC/MS, FAB-MS, and mainly 2D-NMR techniques their structures were identified as 3-O-[β-D-glucopyranosyl(1→3)-β-D-glucopyranosyl]-28-O-[β-D-galactopyranosyl(1→2)-α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-[β-D-xylopyranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-[β-D-apio-D-furanosyl-(1→3)]-β-D-6-deoxyglucopyranosyl-(1→)]-bayogenin (5), 3-O-[β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl]-28-O-[β-D-galactopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-[β-D-xylopyranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-[β-D-apio-D-furanosyl-(1→3)]-arabinopyranosyl-(1→)]bayogenin (6), 3-O-[β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl]-28-O-[β-D-galactopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-[β-D-xylopyranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-6-deoxyglucopyranosyl-(1→)]-bayogenin (7), and 3-O-[β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl]-28-[O-β-D-galactopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-[β-D-xylopyranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]arabinopyranosyl-(1→bayogenin (8).

  NCBI PubMed ID: 1620749
  Publication DOI: 10.1055/s-2006-961398
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Institutions: Institut für Pharmakognosie, Universität Wien, Austria
  Methods: NMR-2D, FAB-MS, GC-MS
  
   
  
  Solidago canadensis
  CSDB ID 147272 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: canadensissaponin 6
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_167188,IEDB_174332,IEDB_190606,IEDB_225177,IEDB_581506,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88

• Article ID: 10088
  Reznicek G, Jurenitsch J, Freiler M, Korhammer S, Haslinger E, Hiller K, Kubelka W "Isolation and structure elucidation of further new saponins from Solidago canadensis" - Planta Medica 58 (1992) 94-98
  

  Four new main saponins (canadensis-saponins 5-8) (compounds 5-8) were isolated from Solidago canadensis L. (Asteraceae). Using GC/MS, FAB-MS, and mainly 2D-NMR techniques their structures were identified as 3-O-[β-D-glucopyranosyl(1→3)-β-D-glucopyranosyl]-28-O-[β-D-galactopyranosyl(1→2)-α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-[β-D-xylopyranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-[β-D-apio-D-furanosyl-(1→3)]-β-D-6-deoxyglucopyranosyl-(1→)]-bayogenin (5), 3-O-[β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl]-28-O-[β-D-galactopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-[β-D-xylopyranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-[β-D-apio-D-furanosyl-(1→3)]-arabinopyranosyl-(1→)]bayogenin (6), 3-O-[β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl]-28-O-[β-D-galactopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-[β-D-xylopyranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-6-deoxyglucopyranosyl-(1→)]-bayogenin (7), and 3-O-[β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl]-28-[O-β-D-galactopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-[β-D-xylopyranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]arabinopyranosyl-(1→bayogenin (8).

  NCBI PubMed ID: 1620749
  Publication DOI: 10.1055/s-2006-961398
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Institutions: Institut für Pharmakognosie, Universität Wien, Austria
  Methods: NMR-2D, FAB-MS, GC-MS
  
   
  
  Solidago canadensis
  CSDB ID 147273 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_115015,IEDB_115136,IEDB_136044,IEDB_136105,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_142489,IEDB_146664,IEDB_149135,IEDB_167188,IEDB_174332,IEDB_190606,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_86,SB_88

• Article ID: 10116
  Higuchi R, Tokimitsu Y, Fujioka T, Komori T, Kawasaki T, Oakenful DG "Structure of desacylsaponins obtained from the bark of Quillaja saponaria" - Phytochemistry 26 (1986) 229-235
  

  A triterpenoid saponin mixture (so-called quillajasaponin) obtained from the bark of Quillaja saponaria was treated with weak alkali and two major desacylsaponins were isolated. On the basis of chemical and spectral evidence, they were determined as 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-apiofuranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside and 28-O-β-D-apiofuranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside. Diazomethane degradation providing selectively the 28-O-glycoside from the 3,28-O-bisglycoside was a useful method for the structure elucidation.

  quillaic acid, triterpenoid saponin, rosaceae, Quillaja saponaria, quillaja bark, quillajasaponin, desacylsaponin, diazomethane degradation, quillaic acid 3, 28-O-bisglycoside

  Publication DOI: 10.1016/S0031-9422(00)81518-6
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Faculty of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan, CSIRO, Division of Food Research, North Ryde, New South Wales, Australia
  Methods: 13C NMR, 1H NMR, EI-MS, FAB-MS, TLC, GLC, methanolysis, alkaline hydrolysis, partial methanolysis, diazomethane degradation
  
   
  
  Quillaja saponaria
  CSDB ID 145524 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_114701,IEDB_115015,IEDB_136105,IEDB_142489,IEDB_149135,IEDB_167188,IEDB_174332,IEDB_225177,IEDB_885823,SB_86

• Article ID: 10116
  Higuchi R, Tokimitsu Y, Fujioka T, Komori T, Kawasaki T, Oakenful DG "Structure of desacylsaponins obtained from the bark of Quillaja saponaria" - Phytochemistry 26 (1986) 229-235
  

  A triterpenoid saponin mixture (so-called quillajasaponin) obtained from the bark of Quillaja saponaria was treated with weak alkali and two major desacylsaponins were isolated. On the basis of chemical and spectral evidence, they were determined as 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-apiofuranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside and 28-O-β-D-apiofuranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside. Diazomethane degradation providing selectively the 28-O-glycoside from the 3,28-O-bisglycoside was a useful method for the structure elucidation.

  quillaic acid, triterpenoid saponin, rosaceae, Quillaja saponaria, quillaja bark, quillajasaponin, desacylsaponin, diazomethane degradation, quillaic acid 3, 28-O-bisglycoside

  Publication DOI: 10.1016/S0031-9422(00)81518-6
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Faculty of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan, CSIRO, Division of Food Research, North Ryde, New South Wales, Australia
  Methods: 13C NMR, 1H NMR, EI-MS, FAB-MS, TLC, GLC, methanolysis, alkaline hydrolysis, partial methanolysis, diazomethane degradation
  
   
  
  Quillaja saponaria
  CSDB ID 295529 (all data & tools)