An oligomer from flaxseed composed of secoisolariciresinoldiglucoside and 3-hydroxy-3-methyl glutaric acid residues

Kamal‐Eldin, Afaf; Peerlkamp, Nienke; Johnsson, Pernilla; Andersson, Roger; Andersson, Ronnie; Lundgren, L.; Åman, Per

doi:10.1016/s0031-9422(01)00279-5

Cited by 98 publications

(58 citation statements)

References 17 publications

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“…Secoisolariciresinol (SECO) is produced by acid hydrolysis of secoisolariciresinol diglycoside. Secoisolariciresinol diglycoside existing bound form as a complex of five secoisolariciresinol diglycoside residues held together by four HMGA (3-hydroxy-3-methylglutaric acid) residues in the outer layers of the seed (Kamal-Eldin et al 2001;Raffaelli et al 2002;Muir 2006). Structures of the flaxseed lignans complied from different sources (Toure and Xueming 2010;Meagher et al 1999) are presented in Fig.…”

Section: Lignansmentioning

confidence: 99%

Flaxseed—a potential functional food source

2014

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There is currently much interest in phytochemicals as bioactive molecules of food. Functional foods are an emerging field in food science due to their increasing popularity among health conscious consumers. Flaxseed is cultivated in many parts of world for fiber, oil as well as for medicinal purposes and also as nutritional product. In this review, nutrients, anti-nutrients, functional properties, processing, metabolism and health benefits of bioactive molecules viz., essential fatty acids, lignans and dietary fiber of flaxseed are discussed.

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Section: Lignansmentioning

confidence: 99%

Flaxseed—a potential functional food source

2014

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“…However, the flaxseed lignans extracted with alcohol are part of complex polymeric structures and therefore they are not readily available for quantification. A hydrolysis step is required in order to break the ester bonds between the flaxseed lignan glucoside, and the 3-hydroxy-3-methyl-glutaric acid in order to release the SDG from the complex structures (Ford et al 2001;Kamal-Eldin et al 2001). Various researchers who used alkaline hydrolysis for quantifying the flaxseed lignans reported only one type of lignan, SDG (Eliasson et al 2003;Johnsson et al 2000;Kamal-Eldin et al 2001;Westcott and Muir 2003a;Zhang and Xu 2007).…”

Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Extraction of Secoisolariciresinol Diglucoside—Method Development

Nemes

Orsat

2009

Food Bioprocess Technol

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An optimized microwave-assisted extraction (MAE) method was developed for extracting secoisolariciresinol diglucoside (SDG) from flaxseed. This paper presents the optimization of factors for maximizing the extraction yield of SDG. This work was conducted using the experimental domain identified in a previous study by means of screening designs, that is, samples of 1 g defatted flaxseed meal (DFM) were extracted with 50 ml NaOH of concentration of 0.5-1 M, at microwave power levels of 60-360 W, for 3-9 min, with the microwave power applied intermittently (power on 30 s/min) and continuously (power on 60 s/min). The MAE of SDG was maximized when 1 g DFM was extracted with 50 ml 0.5 M NaOH, at 135 W, for 3 min in intermittent power mode (power on 30 s/min). The optimized MAE achieved a 6% increase in the extraction yield (21.45 mg SDG per gram DFM) as opposed to a direct hydrolysis method (20.22 mg SDG per gram DFM). The MAE of SDG was governed by the microwave-NaOH interaction, which had a curvilinear dependence on the microwave power level, and linear dependence on the NaOH concentration. The microwave-induced effects accounted for a 10% increase in the SDG extraction yield (21.45 mg SDG per gram DFM) as opposed to a microwaveless control method (19.45 mg SDG per gram DFM). The optimized MAE method has good repeatability, a 97% recovery of the target compound; it is fast and efficient and can be used for precise quantification of SDG in flaxseed.

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“…An oligomer composed of five SDG residues interconnected by four 3-hydroxy-3-methyl glutaric acid (HMGA) residues is identified as the main lignan of flaxseed 95 . SDG oligomers in the flaxseed extract are often hydrolyzed to break the ester linkages for the release of SDG and the glycosidic bonds for the release of SECO 96 .…”

Section: The Absorbable Form Of Lignansmentioning

confidence: 99%

The Comparison of Rat and Human Intestinal and Hepatic Glucuronidation of Enterolactone Derived from Flaxseed Lignans

Lin¹,

Krol²,

Alcorn

2013

NPJ

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The mammalian lignan, enterolactone (EL), is a gut microbe metabolite of plant lignan secoisolariciresinol diglucoside (SDG), which is most abundant in flaxseed. Numerous epidemiological, experimental and clinical studies suggest the protective effects of EL against various chronic diseases such as cancer, cardiovascular disease, and inflammation. However, EL's oral bioavailability is low and highly variable due to extensive first-pass metabolism, especially glucuronidation, which results in the large amount of glucuronide metabolites but low levels of free EL in human plasma. Hepatocytes and enterocytes express UDP-glucuronosyltransferases (UGT), the enzymes responsible for the conjugation of glucuronic acid to EL. To better understand the contribution of liver and intestine to the first-pass glucuronidation, I conducted an in vitro enzyme kinetic analysis of EL glucuronidation using hepatic and intestinal microsomal fractions from both human and rat.An intrinsic clearance (CL int ) value was calculated using the substrate depletion approach. In addition to monitoring substrate depletion, high-pressure liquid chromatography (HPLC) analysis allowed detection of EL glucuronides, which were further substantiated by LC-MS.EL monoglucuronide was identified in rat and human intestinal and liver microsomes.Enzyme kinetic studies indicated the extent of hepatic microsomal glucuronidation exceeded intestinal glucuronidation in both human and rat, while the human liver CL int value was slightly higher than that of rat liver. The CL int value generated in human intestinal microsomes was only one third of the value of human liver, whereas, the CL int of rat jejunum or colon was one-twentieth of rat liver, suggesting the human intestine makes a greater contribution to EL glucuronidation than rat intestine. These results suggest that both liver and intestine contribute to EL glucuronidation and the human intestine may exert a greater influence on the first-pass glucuronidation of EL than rat intestine, thereby significantly decreasing EL's oral bioavailability. The rat might underestimate the extent of intestinal metabolism of EL relative to human.iii

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An oligomer from flaxseed composed of secoisolariciresinoldiglucoside and 3-hydroxy-3-methyl glutaric acid residues

Cited by 98 publications

References 17 publications

Flaxseed—a potential functional food source

Flaxseed—a potential functional food source

Microwave-Assisted Extraction of Secoisolariciresinol Diglucoside—Method Development

The Comparison of Rat and Human Intestinal and Hepatic Glucuronidation of Enterolactone Derived from Flaxseed Lignans

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