Human Intestinal Bacteria Capable of Transforming Secoisolariciresinol Diglucoside to Mammalian Lignans, Enterodiol and Enterolactone.

Wang, Liquan; Meselhy, Meselhy R.; Li, Yan; Qin, Guo‐Wei; Hattori, Masao

doi:10.1248/cpb.48.1606

Cited by 169 publications

(158 citation statements)

References 0 publications

Supporting

Mentioning

145

Contrasting

Unclassified

Order By: Relevance

“…Its molecular ion peak at m/z 332 [M] ϩ in the EI-MS spectrum was 16 mass units less than that of 7. The 1 H-and 13 C-NMR (Table 2) spectra were in good agreement with those of a metabolite reported by Wang et al 9) Compound 8 was consequently determined to be 3-(3Љ-hydroxybenzyl)-2-(4Ј-hydroxy-3Ј-methoxybenzyl)butane-1,4-diol.…”

Section: Resultssupporting

confidence: 87%

“…The 1 H-and 13 C-NMR (Table 2) spectra of 9 were similar to those of 2-(3Ј-hydroxybenzyl)-3-(3Љ,4Љ-dihydroxybenzyl)butane-1,4-diol, a precursor of enterodiol, as reported by Wang et al 9) The structure of 9 was finally determined to be 2-(3Ј,4Ј-dihydroxybenzyl)-3-(3Љ-hydroxybenzyl)butane-1,4-diol on the basis of the HMQC and HMBC experiments.…”

Section: Resultssupporting

confidence: 81%

“…[7][8][9] Pinoresinol, lariciresinol, syringaresinol, 7-hydoxymatairesinol and arctigenin are newly identified enterolactone precursors, 10,11) and a possible metabolic pathway for pinoresinol (formation of mammalian lignans via lariciresinol and secoisolariciresinol) was proposed based on the biosynthetic pathway of secoisolariciresinol and matairesinol in plants. 10) Pinoresinol diglucoside is a major antihypertensive principle of Tu-Chung (the bark of Eucommia ulmoides), used in traditional Chinese medicine, 12) and pinoresinol is contained in cereals, particularly in whole-grain rye products, 1) olive oil, 13) and in various Picea, Pinus and Abies etc.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Biotransformation of Pinoresinol Diglucoside to Mammalian Lignans by Human Intestinal Microflora, and Isolation of Enterococcus faecalis Strain PDG-1 Responsible for the Transformation of (+)-Pinoresinol to (+)-Lariciresinol

et al. 2003

Self Cite

View full text Add to dashboard Cite

Asian people who are vegetarian or semi-vegetarian show a low incidence of and mortality from hormone-dependent diseases, such as breast and prostate cancers, compared with Western people, whose diets are rich in animal protein and fats.1) Consumption of fiber-rich whole grain food elevates a serum mammalian lignan, enterolactone (ENL).2,3) Furthermore, both very low and very high plasma concentrations of ENL are associated with an increased breast cancer risk, 4) and urinary excretion of mammalian lignans [enterodiol (END) and ENL] is low in patients with breast cancer.5,6) All these findings suggest a close relationship between vegetarian diet, mammalian lignans and hormone-dependent diseases. The origins of END and ENL found in human biological fluids and in feces are plant lignans contained in fibrerich whole grain food, which are transformed by intestinal microflora in the proximal colon. 7,8) Until recently, secoisolariciresinol and matairesinol are the only known precursors of END and ENL. 7-9) Pinoresinol, lariciresinol, syringaresinol, 7-hydoxymatairesinol and arctigenin are newly identified enterolactone precursors, 10,11) and a possible metabolic pathway for pinoresinol (formation of mammalian lignans via lariciresinol and secoisolariciresinol) was proposed based on the biosynthetic pathway of secoisolariciresinol and matairesinol in plants. 10) Pinoresinol diglucoside is a major antihypertensive principle of Tu-Chung (the bark of Eucommia ulmoides), used in traditional Chinese medicine, 12) and pinoresinol is contained in cereals, particularly in whole-grain rye products, 1) olive oil, 13) and in various Picea, Pinus and Abies etc.14) The present study was designed for a better understanding of the metabolism of pinoresinol diglucoside by human intestinal microflora, as well as isolation of the bacterial strains responsible for the respective reactions in the transformation. ResultsTransformation of Pinoresinol Diglucoside (PDG, 1) by a Human Intestinal Bacterial Mixture After anaerobic incubation of pinoresinol diglucoside (1) with a bacterial mixture of human feces, the culture was extracted with nBuOH and the extract was subjected to Diaion HP-20, Sephadex LH-20, preparative thin-layer chromatography (TLC) and RP-18 column chromatography. Fifteen metabolites (2-16) were isolated and identified by electron impact mass (EI-MS), one dimensional (1D) and 2D-NMR, and circular dichroic (CD) spectroscopy.Compound 2 was detected as a major metabolite after 6 h of incubation of 1 with a human fecal suspension. The [a] D 25 value measured in MeOH was ϩ69°. The 1 H-and 13 C-NMR spectra (Table 1) were in good agreement with those reported for (ϩ)-pinoresinol, bearing a (7S,7ЈS,8S,8ЈS)-configuration (Fig. 1). 15,16) Compound 3 was a second metabolite when the reaction mixture was monitored by TLC. Its molecular ion peak (m/z 360 [M] ϩ ) in the EI-MS spectrum was 2 mass units (2H) higher than that of 2, suggesting that 3 is a reduced product of 2. The [a] D 25 value in MeOH was ϩ30°. 17) Compound 3 was deter...

show abstract

Section: Resultssupporting

confidence: 87%

Section: Resultssupporting

confidence: 81%

mentioning

confidence: 99%

See 1 more Smart Citation

Biotransformation of Pinoresinol Diglucoside to Mammalian Lignans by Human Intestinal Microflora, and Isolation of Enterococcus faecalis Strain PDG-1 Responsible for the Transformation of (+)-Pinoresinol to (+)-Lariciresinol

et al. 2003

Self Cite

View full text Add to dashboard Cite

show abstract

“…Potential cancer prevention by dietary lignan glycoside, i.e., secoisolariciresinol 37 diglucoside (SDG), has been suggested to be mediated through its metabolites, enterolactone and 38 enterodiol [1][2][3][4][5]. The chemical structures of SDG and its mammalian metabolite enterolactone 39 are shown in Figure 1.…”

Section: Introduction 36mentioning

confidence: 99%

Cytostatic inhibition of cancer cell growth by lignan secoisolariciresinol diglucoside

Ayella¹,

Lim²,

Jiang³

et al. 2010

Nutrition Research

View full text Add to dashboard Cite

“…In addition to being esterified into an oligomer, SDG is complexed with insoluble fiber, gums, polysaccharides, and mucilage associated with the hull (Thompson, Robb, Serraino, & Cheung, 1991). SDG is the main precursor of the mammalian lignans enterodiol (ED) and enterolactone (EL), which are formed by intestinal mammalian bacteria (Clavel, Borrmann, Braune, Dore, & Blaut, 2006;Eeckhaut et al, 2008;Wang, Meselhy, Li, Qin, & Hattori, 2000). The enterolignans ED and EL have phytoestrogenic effects due to their similarity to 17β-estradiol, which regulates sex-specific functions, and may be involved in preventing some cancers (Muir & Wescott, 2003).…”

Section: Introductionmentioning

confidence: 99%

Optimization of secoisolariciresinol diglucoside extraction from flaxseed (Linum usitatissimumL.) and isolation by a simple HPLC-UV method

Fuentealba

Figuerola

Estévez

et al. 2014

CyTA - Journal of Food

View full text Add to dashboard Cite

Optimization of secoisolariciresinol diglucoside extraction from flaxseed (Linum usitatissimum L.) and isolation by a simple HPLC-UV method Optimización de la extracción de secoisolariciresinol diglucósido desde linaza (Linum usitatissimum L.) y su purificación a través de un método simple HPLC-UV This research was conducted to develop and optimize a methodology to quantify the content of secoisolariciresinol diglucoside (SDG), the main vegetable lignan present in flaxseed. However, at the time of this work, commercial SDG was not available for standard use. Therefore, an effective method to obtain purified SDG from flaxseed was developed using chromatographic techniques. The SDG obtained was of approximately 97% purity. The methanol extraction time, alkali concentrations, and reaction temperature were optimized through a response surface methodology (RSM), and the optimal conditions established for the extractions were 47°C, 58 mmol L −1 sodium methoxide, and 24 h. This methodology was then applied to study the variation of SDG content in flaxseed from different cultivars. The SDG content in different varieties of flaxseed ranged from 10.8 to 17.9 mg g −1 in defatted flaxseed flour and from 6.0 to 10.9 mg g −1 in whole flaxseed.Keywords: flaxseed; lignan; secoisolariciresinol diglucoside; RSM El objetivo de esta investigación fue desarrollar y optimizar una metodología para cuantificar el contenido de secoisolariciresinol diglucósido (SDG), el cual es el principal lignano vegetal presente en linaza. Sin embargo, al realizar este trabajo no existía SDG comercial para ser utilizado como estándar externo. Por lo tanto, se desarrolló un método efectivo para obtener SDG purificado usando técnicas cromatográficas. El SDG obtenido fue de 97% de pureza. Se optimizó el tiempo de extracción metanólica, concentración de alcali y temperatura de reacción a través de un diseño de superficie respuesta. Las condiciones óptimas establecidas fueron: 47°C, 58 mmol L −1 de metóxido de sodio y 24 h. Esta metodología luego fue aplicada para estudiar la variación del contenido de SDG en linaza de diferentes cultivares. El contenido de SDG en diferentes variedades de linaza se encontró en el rango de 10,8 a 17,9 mg g −1 en harina desgrasada de linaza y de 6,0 a 10,9 mg g −1 en linaza entera.

show abstract

Human Intestinal Bacteria Capable of Transforming Secoisolariciresinol Diglucoside to Mammalian Lignans, Enterodiol and Enterolactone.

Cited by 169 publications

References 0 publications

Biotransformation of Pinoresinol Diglucoside to Mammalian Lignans by Human Intestinal Microflora, and Isolation of Enterococcus faecalis Strain PDG-1 Responsible for the Transformation of (+)-Pinoresinol to (+)-Lariciresinol

Biotransformation of Pinoresinol Diglucoside to Mammalian Lignans by Human Intestinal Microflora, and Isolation of Enterococcus faecalis Strain PDG-1 Responsible for the Transformation of (+)-Pinoresinol to (+)-Lariciresinol

Cytostatic inhibition of cancer cell growth by lignan secoisolariciresinol diglucoside

Optimization of secoisolariciresinol diglucoside extraction from flaxseed (Linum usitatissimumL.) and isolation by a simple HPLC-UV method

Contact Info

Product

Resources

About