Bioactive saponins and glycosides. VIII. Notoginseng (1) : new dammarane-type triterpene oligoglycosides, notoginsenosides-A, -B, -C, and -D, from the dried root of Panax notoginseng (Burk.) F.H. Chen
Yoshikawa, M.; Murakami, T.; Ueno, T.; Yashiro, K.; Hirokawa, N.; Murakami, N.; Yamahara, J.; Matsuda, H.; Saijoh, R.; Tanaka, O.
Chemical and Pharmaceutical Bulletin 45(6): 1039-1045
1997
ISSN/ISBN: 0009-2363 PMID: 9214709 DOI: 10.1248/cpb.45.1039
Accession: 030293095
The glycosidic fraction from the dried roots of Panax notoginseng (BURK.) F. H. CHEN was found to show protective effect on liver injury induced by D-galactosamine and lipopolysaccharide. From the glycosidic fraction with hepatoprotective effect, nine new dammarane-type triterpene oligoglycosides, notoginsenosides-A, -B, -C, -D, -E, -G, -H, -I, and -J and an acetylenic fatty acid glycoside, notoginsenic acid beta-sophoroside, were isolated together with fourteen known dammarane-type triterpene oligoglycosides. The structures of notoginsenosides-A, -B, -C, and -D were determined on the basis of chemical and physicochemical evidence, which included the chemical correlation with ginsenoside-Rb-1 using photosensitized oxygenation, as follows: notoginsenoside A; 3-O-(beta-D-glucopyranosyl (1 fwdarw 2)-beta-D-glucopyranosyl)-20-O-(beta-D-glucopyranosyl (1 fwdarw 6)-beta-D-glucopyranosyl) 3-beta,12-beta,20(S),25-tetrahydroxydammar-23-ene, B; 3-O-(beta-D-glucopyranosyl (1 fwdarw 2)-beta-D-glucopyranosyl)-20-O-(beta-D-glucopyranosyl (1 fwdarw 6)-beta-D-glucopyranosyl) 3-beta,12-beta,20(S)-trihydroxydammar-25-en-24-one, C; 3-O-(beta-D-glucopyranosyl (1 fwdarw 2)-beta-D-glucopyranosyl)-20-O-(beta-D-glucopyranosyl (1 fwdarw 6)-beta-D-glucopyranosyl) 3-beta,12-beta,20(S)-trihydroxy-24-xi-hydroperoxydammar-25-ene, and D; 3-O-(beta-D-xylopyranosyl (1 fwdarw 2)-beta-D-glucopyranosyl (1 fwdarw 2)-beta-D-glucopyranosyl)-20-O-(beta-D-xylopyranosyl (1 fwdarw 6)-beta-D-glucopyranosyl (1 fwdarw 6)-beta-D-glucopyranosyl) 20(S)-protopanaxadiol, respectively.