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Structure type: oligomer ; 1145.5734 [M+Na]+
C₅₄H₉₁O₂₄
Trivial name: quinquenoside IV
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_140628,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_241101,IEDB_983931,SB_192

• Article ID: 11329
  Yoshikawa M, Murakami T, Yashiro K, Yamahara J, Matsuda H, Saijoh R, Tanaka O "Bioactive saponins and glycosides. XI. Structures of new dammarane-type triterpene oligoglycosides, quinquenosides I, II, III, IV, and V, from American ginseng, the roots of Panax quinquefolium L." - Chemical and Pharmaceutical Bulletin 46(4) (1998) 647-654
  

  The methanolic extract and I-butanol-soluble fraction of American ginseng, the roots of Panax quinquefolium L., were found to exhibit a protective effect on liver injury induced by D-galactosamine and lipopolysaccharide. Five new dammarane-type triterpene oligoglycosides called quinquenosides I, II, III, IV, and V were isolated together with fourteen known dammarane-type triterpene oligoglycosides such as chikusetsusaponin IVa, pseudo-ginsenoside-RC1, malonyl-ginsenoside-Rb-1, and notoginsenosides-A, -C, and -K from the 1-butanol-soluble fraction. From the ethyl acetate-soluble fraction, four known acetylenic compounds and 6'-O-acetyl ginsenoside-Rg(1) were isolated. The structures of quinquenosides I, II, III, IV, and V were determined on the basis of chemical and physicochemical evidence as 3-O-[6-O-(E)-2-butenoyl-beta-D-glucopyranosyl(1 --> 2)-beta-D-glucopyranosyl]-20-O-(beta-D-glucopyranosyl) 20(S)-protopanaxadiol (quinquenoside I), 3-O-[6-O-(E)-2-octenoyl-beta-D-glucopyranosyl(1 --> 2)-beta-D-glucopyranosyl]-20-O- [beta-D-glucopyranosyl(1 --> 6)-beta-D-glucopyranosyl] 20(S)-protopanaxadiol (quinquenoside II), 3-O-[beta-D-glucopyranosyl (1 --> 2)-6-O-acetyl-beta-D-glucopyranosyl]-20-O-(beta-D-glucopyranosyl) 20(S)-protopanaxadiol (quinquenoside III), 3-O-[beta-D-glucopyranosyl(1 --> 2)-beta-D-glucopyranosyl]-20-O-[beta-D-glucopyranosyl(1 --> 6)-beta-D-glucopyranosyl]-3 beta,7 beta,20(S)-trihydroxydammar-5,24-diene (quinquenoside IV), and 3-O-[beta-D-glucopyranosyl(1 --> 2)-beta-D-glucopyranosyl]-20-O- [alpha-D-glucopyranosyl(1 --> 4)-beta-D-glucopyranosyl(1 --> 6)-beta-D-glucopyranosyl] 20(S)-protopanaxadiol (quinquenoside V).

  Panax quinquefolium, bioactive saponin, dammarane-type triterpene oligoglycoside, American ginseng, quinquenoside, hepatoprotective effect

  NCBI PubMed ID: 9579041
  Publication DOI: 10.1248/cpb.46.647
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Kyoto Pharmaceutical University, Kyoto, Japan, Suzugamine Women's College, Hiroshima, Japan, New Product Development Division, Teikoku Seiyaku Co., Ltd., Tokyo, Japan
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, HPLC, alkaline hydrolysis, UV, optical rotation measurement, ROESY, melting point determination, HMBC, HR-FAB-MS, extraciton, reverse-phase silica gel CC
  
   
  
  Panax quinquefolium
  CSDB ID 61240 (all data & tools)