Xie Li-Hua, Akao Teruaki, Hamasaki Kenjiro, Deyama Takeshi, Hattori Masao
Institute of Natural Medicine, Toyama Medical and Pharmaceutical University, Sugitani, Toyama, Japan.
Chem Pharm Bull (Tokyo). 2003 May;51(5):508-15. doi: 10.1248/cpb.51.508.
By anaerobic incubation of pinoresinol diglucoside (1) from the bark of Eucommia ulmoides with a fecal suspension of humans, eleven metabolites were formed, and their structures were identified as (+)-pinoresinol (2), (+)-lariciresinol (3), 3'-demethyl-(+)-lariciresinol (4), (-)-secoisolariciresinol (5), (-)-3-(3", 4"-dihydroxybenzyl)-2-(4'-hydroxy-3'-methoxybenzyl)butane-1, 4-diol (6), 2-(3', 4'-dihydroxybenzyl)-3-(3", 4"-dihydroxybenzyl)butane-1, 4-diol (7), 3-(3"-hydroxybenzyl)-2-(4'-hydroxy-3'-methoxybenzyl)butane-1, 4-diol (8), 2-(3', 4'-dihydroxybenzyl)-3-(3"-hydroxybenzyl)butane-1, 4-diol (9), (-)-enterodiol (10), (-)-(2R, 3R)-3-(3", 4"-dihydroxybenzyl)-2-(4'-hydroxy-3'-methoxybenzyl)butyrolactone (11), (-)-(2R, 3R)-2-(3', 4'-dihydroxybenzyl)-3-(3", 4"-dihydroxybenzyl)butyrolactone (12), (-)-(2R, 3R)-3-(3"-hydroxybenzyl)-2-(4'-hydroxy-3'-methoxybenzyl)butyrolactone (13), 2-(3', 4'-dihydroxybenzyl)-3-(3"-hydroxybenzyl)butyrolactone (14), 2-(3'-hydroxybenzyl)-3-(3", 4"-dihydroxybenzyl)butyrolactone (15) and (-)-(2R, 3R)-enterolactone (16) by various spectroscopic means, including two dimensional (2D)-NMR, mass spectrometry and circular dichroism. A possible metabolic pathway was proposed on the basis of their structures and time course experiments monitored by thin-layer chromatography. Furthermore, a bacterial strain responsible for the transformation of (+)-pinoresinol to (+)-lariciresinol was isolated from a human fecal suspension and identified as Enterococcus faecalis strain PDG-1.
通过将杜仲树皮中的松脂醇二葡萄糖苷（1）与人粪便悬浮液进行厌氧培养，形成了11种代谢产物，通过包括二维（2D）-NMR、质谱和圆二色性在内的各种光谱手段鉴定出它们的结构分别为（+）-松脂醇（2）、（+）-落叶松脂醇（3）、3'-去甲基-（+）-落叶松脂醇（4）、（-）-开环异落叶松脂醇（5）、（-）-3-（3",4"-二羟基苄基）-2-（4'-羟基-3'-甲氧基苄基）丁烷-1,4-二醇（6）、2-（3',4'-二羟基苄基）-3-（3",4"-二羟基苄基）丁烷-1,4-二醇（7）、3-（3"-羟基苄基）-2-（4'-羟基-3'-甲氧基苄基）丁烷-1,4-二醇（8）、2-（3',4'-二羟基苄基）-3-（3"-羟基苄基）丁烷-1,4-二醇（9）、（-）-肠二醇（10）、（-）-（2R,3R）-3-（3",4"-二羟基苄基）-2-（4'-羟基-3'-甲氧基苄基）丁内酯（11）、（-）-（2R,3R）-2-（3',4'-二羟基苄基）-3-（3",4"-二羟基苄基）丁内酯（12）、（-）-（2R,3R）-3-（3"-羟基苄基）-2-（4'-羟基-3'-甲氧基苄基）丁内酯（13）、2-（3',4'-二羟基苄基）-3-（3"-羟基苄基）丁内酯（14）、2-（3'-羟基苄基）-3-（3",4"-二羟基苄基）丁内酯（15）和（-）-（2R,3R）-肠内酯（16）。基于它们的结构和通过薄层色谱监测的时间进程实验，提出了一条可能的代谢途径。此外，从人粪便悬浮液中分离出一株负责将（+）-松脂醇转化为（+）-落叶松脂醇的细菌菌株，并鉴定为粪肠球菌菌株PDG-1。
