Catechine

Compound Catechine 
Animal species human intestinal bacteria Eubacterium sp. straun SDG-2 
Metabolism parameters  
Metabolites (+)-(2R, 3S)-Catechin
(R)-2-(3-(3,4-dihydroxyphenyl)-2-hydroxypropyl)benzene-1,3,5-triol
(-)-(2R, 3S)-Catechin
(S)-2-(3-(3,4-dihydroxyphenyl)-2-hydroxypropyl)benzene-1,3,5-triol
(S)-2-(2-hydroxy-3-(3-hydroxyphenyl)propyl)benzene-1,3,5-triol
(-)-Gallocatechin (2S, 3R)
(S)-5-(2-hydroxy-3-(2,4,6-trihydroxyphenyl)propyl)benzene-1,2,3-triol
(S)-2-(3-(3,5-dihydroxyphenyl)-2-hydroxypropyl)benzene-1,3,5-triol
Crude drug  
References 1) Wang L., Meselhy M. R., Li Y., Nakamura N., Min B., Qin G. and Hattori M.: The heterocyclic ring fission and dehydroxylation of catechins and related compounds by Eubacterium sp. strain SDG-2, a human intestinal bacterium. Chem. Pharm. Bull., 49, 1640-1643 (2001). 
Remarks ※Incubation of (+)-catechin (1a) with Eubacterium sp. strain SDG-2
(+)-Catechin (1a) (30 mg in 2 ml MeOH) was added to a bacterial suspension (50 ml) of E. sp. strain SDG-2, and incubated at 37°C in an anaerobic incubator for 36 h. The reaction mixture was then extracted with water-saturated BuOH (3 × 50 ml). The organic layer was evaporated under reduced pressure to give a residue (95 mg). The residue was applied to a column of silica gel. The column was thoroughly washed with CHCl3 and then eluted with CHCl3-MeOH (10:1). Fractions were pooled to give fr. A and B. Repeated column chromatography on Sephadex LH-20 (aq. 95% MeOH) and RP-18 (MeOH-H2O, 4:6) of fr. B to give 2a (16 mg). [Wang et al., Chem. Pharm. Bull., 49, 1640-1643 (2001)]

※Incubation of (-)-catechin (1b) with E. sp. strain SDG-2
(-)-Catechin (1b) (10 mg in 1 ml MeOH) was anaerobically incubated with a bacterial suspension (20 ml) at 37°C for 36 h. After extraction and evaporation, the residue was applied to a column of silica gel, which was washed thoroughly with CHCl3, followed by CHCl3-MeOH (20:1 and 10:1) to give fr. A-C. After repeated column chromatography on Sephadex LH-20 (aq. 95% MeOH) and RP-18 (MeOH-H2O, 4:6), fr. B and C gave 3b (2.0 mg) and 2b (1.5 mg), respectively. [Wang et al., Chem. Pharm. Bull., 49, 1640-1643 (2001)] 
 

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