32773-56-1Relevant articles and documents
Biotransformation of saponins by endophytes isolated from Panax notoginseng
Luo, Shao-Liu,Dang, Li-Zhi,Li, Jian-Fang,Zou, Cheng-Gang,Zhang, Ke-Qin,Li, Guo-Hong
, p. 2021 - 2031 (2013/12/04)
The biotransformation of the major saponins in Panax notoginseng, including the ginsenosides Rg1, Rh1, Rb1, and Re, by endophytes isolated from P. notoginseng was studied. One hundred and thirty-six endophytes were isolated and screened for their biotransformational abilities. The results showed that five of the tested endophytes were able to transform these saponins. These five strains were identified based on their ITS or 16S rDNA sequences, which revealed that they belonged to the genera Fusarium, Nodulisporium, Brevundimonas, and Bacillus genera. Ten transformed products were isolated and identified, including a new compound 6-O-[α-L-rhamnopyranosyl-(1→2)-β-D- glucopyranosyl]-20-O-β-D-glucopyranosyldammarane-3,6,12,20,24,25-hexaol (3), and nine known compounds, compound K (1), ginsenoside F2 (2), vinaginsenoside R13 (4), vinaginsenoside R22 (5), pseudo-ginsenoside RT4 (6), (20S)-protopanaxatriol (7), ginsenoside Rg1 (8), vinaginsenoside R15 (9), and (20S)-3-O-β-D-glucopyranosyl-6-O-β-D-glucopyranosylprotopanaxatriol (10). This is the first study on the biotransformation of chemical components in P. notoginseng by endophytes isolated from the same plant. Copyright
Characterization of metabolism and in vitro permeability study of notoginsenoside R1 from radix notoginseng
Ruan, Jian-Qing,Leong, Weng-Im,Yan, Ru,Wang, Yi-Tao
experimental part, p. 5770 - 5776 (2011/08/05)
As a main and characteristic constituent in Radix notoginseng, the fate of notoginsenoside R1 (NGR1) in human is largely unknown. The present study investigated, for the first time, NGR1 metabolism by human intestinal bacteria and liver subcellular fractions, and permeability properties of NGR1 and resultant metabolites on a Caco-2 model. Samples were qualitatively analyzed using HPLC-MS/MS and quantitatively determined using HPLC-UV. When incubated with pooled human intestinal bacteria anaerobically, NGR1 showed biphasic elimination: an insignificant decrease in the first 8 h followed by a rapid elimination during 8-48 h. Four metabolites, three unambiguously identified as ginsenosides Rg1, F1 and 20(S)-protopanaxatriol formed via stepwise deglycosylation, and one tentatively assigned as a dehydrogenated protopanaxatriol with transformation occurring at the tetracyclic triterpenoid skeleton, were produced sequentially. Rg1 and F1 were formed transiently at low apparent velocities, while 20(S)-protopanaxatriol was the major metabolite with a formation rate close to the rate of NGR1 elimination and a low elimination rate. NGR1 remained intact in human liver S9 or microsomes over 1 h. Transport study of NGR1 and its metabolites revealed an ascending permeability order with stepwise deglycosylation. Taken together, the results revealed a determinant role of intestinal bacteria in the overall disposition and potential bioactivity of NGR1 in human.
Novel Mechanism for Oxidative Cleavage of Glycosidic Bonds: Evidence for an Oxygen Dependent Reaction
Cui, Jian-Fang,Bystroem, Styrbjoern,Eneroth, Peter,Bjoerkhem, Ingemar
, p. 8251 - 8255 (2007/10/02)
In a previous work from our laboratory, an optimized procedure was worked out for cleavage of the glucosidic bonds in ginsenosides (Cui, J.F.; Garle, M.; Lund, E.; Bjoerkhem, I.; Eneroth, P.Anal.Biochem. 1993, 210, 411-417).When the reaction was performed in n-butanol, alkaline conditions were found to give a considerably better and almost quantitative yield of intact aglyconic-specific products than did acidic conditions.This is surprising in view of the current concept that glucosidic bonds are more stable under alkaline than acidic conditions.It is shown here that the alkaline cleavage is oxygen dependent and that there is little or no conversion when oxygen or air is replaced with nitrogen.Addition of an anti-oxidant, glucose or water also reduces the degree of cleavage under the conditions employed.Replacement of n-butanol for sec-, iso- or 2-methyl-2-propanol, decreased the yield of products to about 75percent and when n- or isopropanol was used as solvent the yield decreased to about 40percent.It was shown that the glucose moiety was completely degraded under the conditions employed and that formate and carbonate, in a ratio of 5/1, were the major products.A mechanistic rationale for the oxygen dependent cleavage of the glucosidic bonds is suggested.The possibility that this mechanism may be of protective importance in biological systems under some specific conditions is also discussed.
