82166-13-0

Upstream product

• 88156-44-9 malonyl-ginsenoside Rb₂ 
• 1346522-90-4 (20S)-3-O-{β-D-6-O-[(E)-but-2-enoyl]glucopyranosyl-(1->2)-β-D-glucopyranosyl}-20-O-[α-L-arabinopyranosyl-(1->6)-β-D-glucopyranosyl]protopanaxadiol 

Downstream Products

• 6892-79-1 protopanaxadiol 
• 52705-93-8 ginsenoside Rd 
• 62025-49-4 ginsenoside F₂ 
• 364779-15-7 ginsenoside Rk₃ 
• 39262-14-1 compound K 

Relevant academic research and scientific papers

Studies on absorption, distribution, excretion and metabolism of Ginseng saponins. VIII. Isotope labeling of ginsenoside Rb2

To clarify the pharmacokinetics of absorption, distribution and excretion of ginsenoside Rb2 (Rb2), one of the major saponins of the root of Panax ginseng, following oral administration to rats, a tritium (3H) labeling of Rb2 was examined. The C-12 position of Rb2 was labeled with 3H-sodium borohydride (3H-NaBH4) and 12-3H Rb2 and 12-3H-epi Rb2 was synthesized. This method of specific position labeling of Rb2 may be applicable to other ginsenosides. In the near future, the pharmacokinetics of Rb2 in rats may be clarified with 3H labeled Rb2.

Synthetic access toward the diverse ginsenosides

All the possible types of the protopanaxatriol and protopanaxadiol glycosides, the major active yet extremely heterogeneous principles of ginsengs, could be accessed by the present sequence of transformations, including global removal of the sugar residue

Acylated protopanaxadiol-type ginsenosides from the root of Panax ginseng

Six new protopanaxadiol-type ginsenosides, named ginsenosides Ra 4-Ra9 (1-6, resp.), along with 14 known dammarane-type triterpene saponins, were isolated from the root of Panax ginseng, one of the most important Chinese medicinal herbs. The structures of the new compounds were determined by spectroscopic methods, including 1D- and 2D-NMR, HR-MS, and chemical transformation as (20S)- 3-O-{β-D-6-O-[(E)-but-2-enoyl] glucopyranosyl-(1→2)-β-D-glucopyranosyl}-20-O-[β-D-xylopyranosyl- (1→4)-α-L-arabinopyranosyl-(1→6)-β-D-glucopyranosyl] protopanaxadiol (1), (20S)-3-O-[β-D-6-O-acetylglucopyranosyl-(1→2)- β-D-glucopyranosyl]-20-O-[β-D-xylopyranosyl-(1→4) -α-L-arabinopyranosyl-(1→6)-β-D-glucopyranosyl]protopanaxadiol (2), (20S)-3-O-{β-D-6-O-[(E)-but-2-enoyl]glucopyranosyl-(1→2)-β- D-glucopyranosyl}-20-O-[β-D-glucopyranosyl-(1→6)-β-D- glucopyranosyl]protopanaxadiol (3), (20S)-3-O-{β-D-6-O-[(E)-but-2-enoyl] glucopyranosyl-(1→2)-β-D-glucopyranosyl}-20-O-[α-L- arabinopyranosyl-(1→6)-β-D-glucopyranosyl]protopanaxadiol (4), (20S)-3-O-{β-D-4-O-[(E)-but-2-enoyl]glucopyranosyl-(1→2) -β-D-glucopyranosyl}-20-O-[α-L-arabinofuranosyl-(1→6) -β-D-glucopyranosyl]protopanaxadiol (5), (20S)-3-O-{β-D-6-O-[(E)-but- 2-enoyl]glucopyranosyl-(1→2)-β-D-glucopyranosyl}-20-O-[α-L- arabinofuranosyl-(1→6)-β-D-glucopyranosyl]protopanaxadiol (6). The sugar moiety at C(3) of the aglycone of each new ginsenoside is butenoylated or acetylated. Copyright

Purification and characterization of ginsenoside Ra-hydrolyzing beta-D-xylosidase from Bifidobacterium breve K-110, a human intestinal anaerobic bacterium.

Beta-D-Xylosidase (EC 3.2.1.37) has been purified from ginsenoside Ra-metabolizing Bifidobacterium breve K-110, which was isolated from human intestinal microflora. beta-D-Xylosidase was purified to apparent homogeneity by a combination of ammonium sulfate precipitation, QAE-cellulose, butyl-toyopearl, hydroxyapatit and Q-Sepharose column chromatographies with the final specific activity of 51.8 micromol/min/mg. Molecular weight of beta-D-xylosidase is 49 kDa by SDS-PAGE and gel filtration, which consisted of a single subunit. beta-D-Xylosidase showed optimal activity at pH 5.0 and 37 degrees C. The purified enzyme was potently inhibited by PCMS. beta-D-Xylosidase acted to the greatest extent on p-nitrophenyl-beta-D-xylopyranoside, followed by ginsenoside Ra1 and ginsenoside Ra2. This enzyme hydrolyzed xylan to xylose, but did not act on p-nitrophenyl-beta-glucopyranoside, p-nitrophenyl-beta-galactopyranoside or p-nitrophenyl-beta-D-fucopyranoside. These findings suggest that this is the first reported purification of ginsenoside-hydrolyzing beta-D-xylosidase from an anaerobic Bifidobacterium sp.

Malonyl-ginsenosides Rb1, Rb2, Rc and Rd, four new malonylated dammarane-type triterpene oligoglycosides from Ginseng Radix

Four new malonylated dammarane-type triterpene oligoglycosides, named malonyl-ginsenosides Rb1 (1), Rb2 (2), Rc (3), and Rd (4), were isolated from Ginseng Radix, the root of Panax ginseng, and their structures were elucidated on the basis of chemical and physicochemical evidence.