Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: root
The structure was elucidated in this paperNCBI PubMed ID: 9579041Publication DOI: 10.1248/cpb.46.647Journal NLM ID: 0377775Publisher: 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
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
Structure type: oligomer
Location inside paper: p. 650, Chart 3, compound 14
Trivial name: ginsenoside-F2, ginsenoside F2
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
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
Related record ID(s): 61237, 61238, 61239, 61240, 61241, 61242, 61243, 61244, 61245, 61246, 61247, 61248, 61249, 61251, 61252, 61253, 61254, 61255, 61954, 61955
NCBI Taxonomy refs (TaxIDs): 44588Reference(s) to other database(s): CCSD:
27076, CBank-STR:2956
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
report error
(later renamed to: Panax quinquefolius)