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. 2011 Feb 1;16(2):1336-48.
doi: 10.3390/molecules16021336.

Role of intestinal hydrolase in the absorption of prenylated flavonoids present in Yinyanghuo

Yan Chen  1 , Jinyan Wang, Xiaobin Jia, Xiaobin Tan, Ming Hu
Affiliations

Role of intestinal hydrolase in the absorption of prenylated flavonoids present in Yinyanghuo

Yan Chen et al. Molecules. .

Abstract

Purpose: Yinyanghuo (Herba Epimdii) is a traditional Chinese herb containing prenylated flavonoids as its active constituents. The aim of this study was to examine the significance of the intestinal hydrolysis of prenylated flavonoids by lactase phlorizin hydrolase (LPH), an enzyme at the brush border membrane of intestinal cells.

Methods: A four-site perfused rat intestinal model was used. The concentration of the flavonoids of interest and their metabolites in different intestinal segements were analyzed by HPLC, and the apparent permeabilities were calculated. A lactase phlorizin hydrolase inhibitor (gluconolactone) was employed to investigate the mechanism of the intestinal absorption, and the metabolites of the four flavonoids were identified using LC/MS/MS.

Results: Diglycosides (icariin) or triglycosides (epimedin A, epimedin B, and epimedin C) were hydrolyzed rapidly in duodenum and jejunum producing one or two metabolites, while a monoglycoside (baohuoside I) was absorbed directly. When co-perfused with glucono-lactone, both the hydrolysis of diglycosides and triglycosides were significantly inhibited, with inhibition rates for icariin (62%, 50%, 40%, 46%), epimedin A, (55%, 26%, 21%, 14%); epimedin B (42%, 40%, 74%, 22%), and epimedin C (42%, 40%, 52%, 35%) in duodenum, jejunum, ileum, and colon, respectively. Also the metabolites of icariin, epimedin A, epimedin B, and epimedin C were identified as baohuoside I (one of two), sagittatoside A, sagittatoside B, and 2"-O-rhamnosylicariside II, respectively.

Conclusions: The results showed that lactase phlorizin hydrolase was a major determinant of the intestinal absorption of prenylated flavonoids present in Yinyanghuo.

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Figures

Figure 1
Figure 1
Chemical structures of five prenylated flavonoids isolated from Yinyanghuo or Epimedium koreamum Nakai: icariin, epimedin A, epimedin B, epimedin C, and baohuoside I. The symbol “glc” refers to glucose, “rha” to rhamnose, and “xyl” to xylose.
Figure 2
Figure 2
HPLC elution profiles of five prenylflavonoids and their intestinal metabolites as following sequence: duodenum, jejunum, ileum and colon. A(baohuoside I), B(icariin), C(epimedin A), D(epimedin B), E(epimedin C). Testosterone was used as an internal standard (IS).
Figure 2
Figure 2
HPLC elution profiles of five prenylflavonoids and their intestinal metabolites as following sequence: duodenum, jejunum, ileum and colon. A(baohuoside I), B(icariin), C(epimedin A), D(epimedin B), E(epimedin C). Testosterone was used as an internal standard (IS).
Figure 3
Figure 3
Comparison of permeability of icariin, epimedine A, epimedine B, epimedine C in different intestinal segements. a: icariin, b: epimedin A, c: epimedin B, d: epimedin C. Data are expressed as mean ± SD (n = 4). The statistically significant difference is shown by the asterisk symbol, icariin vs. epimedin A, epimedin B, epimedin C, * P < 0.05.
Figure 4
Figure 4
Permeability of 10 μM flavonoids absence or presence of LPH enzyme inhibitor.
Figure 5
Figure 5
MSn spectra corresponding to the metabolite peaks of prenylflavonoids.
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