Bioactive Lignans from Flaxseed: Biological Properties and Patented Recovery Technologies (original) (raw)

Human metabolism of mammalian lignan precursors in raw and processed flaxseed

The American Journal of Clinical Nutrition, 1999

Background: The mammalian lignans enterolactone and enterodiol are produced in the colon by the action of bacteria on the plant precursor secoisolariciresinol diglycoside, which is found in high concentrations in flaxseed. Objective: Two experiments were conducted to determine 1) whether there is a dose response in urinary lignan excretion with increasing flaxseed intake, 2) whether flaxseed processing affects lignan excretion, 3) peak plasma lignan concentrations, and 4) plasma lignan concentrations after chronic supplementation. Design: Nine healthy young women supplemented their diets with 5, 15, or 25 g raw or 25 g processed (muffin or bread) flaxseed for 7 d during the follicular phase of their menstrual cycles. Twentyfour-hour urine samples were collected at baseline and on the final day of supplementation. As an adjunct to the 25-g-flaxseed arm, subjects consumed the supplement for an additional day and blood and urine samples were collected at specific intervals. All blood and urine samples were analyzed for enterolactone and enterodiol by gas chromatography-mass spectroscopy. Results: A dose-dependent urinary lignan response to raw flaxseed was observed (r = 0.72, P ≤ 0.001). The processing of flaxseed as a muffin or bread did not affect the quantity of lignan excretion. Plasma lignan concentrations were greater (P ≤ 0.05) than baseline by 9 h after flaxseed ingestion (29.35 ± 3.69 and 51.75 ± 7.49 nmol/L, respectively). The total plasma area under the curve was higher on the eighth than on the first day (1840.15 ± 343.02 and 1027.15 ± 95.71 nmol • h/L, respectively). Conclusion: Mammalian lignan production from flaxseed precursors is dependent on time and dose but not on processing.

“ Lignan ”-Antioxidant of Linseed

2016

One of the most interesting characteristics of flaxseed is its content of complex phenols, such as lignans. The most remarkable one is secoisolariciresinol (SDG), although isolariciresinol, pinoresinol, mataresinol and other derivatives of ferulic acid are also present. Lignan consumption reduces cardiovascular risk and inhibits the development of some types of diabetes. Health benefits of flax lignans reside in their antioxidant capacity as sequestrators of hydroxyl radicals and as estrogenic compounds due to their structural similarity to 17--estradiol. The antioxidant capacity of SDG is related to the suppression of the oxidant conditions due to oxygen species. SDG diglycoside and its aglycone, secoisolariciresinol display a very high antioxidant capacity and act as protectors against damage to DNA and liposomes especially in the epithelial cells of the colon exposed to these compounds during the metabolism of colon bacteria, which transform them into mammal lignans. The food an...

Anticancer potentiality of lignan rich fraction of six Flaxseed cultivars

Scientific reports, 2018

The objective of our study is to highlight the therapeutic effect and mechanism of action by which purified Flaxseed hydrolysate (PFH) which is a lignan rich fraction exerts its anticancer activity on a human breast cancer cell line (T47D) and in mice bearing tumor. HPLC analysis of PFH of six flaxseed cultivars had shown that PFH of the cultivar Giza 9 (PFH-G9) contains the highest concentration of SDG (81.64 mg/g). The in vitro cytotoxic potentiality of PFH's of six flaxseed cultivars was screened against a panel of human cancer cell lines. PFH -G9 showed the most significant cytotoxic activity against ER-receptor positive breast cell lines MCF7 and T47D with IC50 13.8 and 15.8 µg/ml, respectively. Moreover, PFH-G9 reduced the expression of the metastasis marker, 1-α, metalloproteinases and vascular endothelial growth factor (VEGF), one of the most potent stimulators of angiogenesis, while it increased the caspase-3 dependent apoptosis. Our study also showed that dietary intak...

Antioxidant capacity of flaxseed lignans in two model systems

Journal of the American Oil Chemists' Society, 2006

The flaxseed lignans secoisolariciresinol (SECO) and its diglucoside secoisolariciresinol diglucoside (SDG) are reported to have a number of health benefits associated with their consumption that have in part been attributed to their antioxidant properties. In this study the relative antioxidant capacity of the flaxseed lignans vs. BHT was determined in two model systems. First, an antioxidant stoichiometric value was determined for SECO and SDG in a liposomal system as a mimic of lipid peroxidation. Stoichiometric values for SECO (1.5) and SDG (1.2) vs. BHT (2.0) were measured from the lag time for the formation of conjugated dienes; all values were significantly different (P < 0.01). Second, the ability of flaxseed lignans to prevent oxidative degradation of canola oil was determined. Samples were stored at room temperature and analyzed at 30-d intervals over 120 d using a Rancimat TM analyzer. The lignans prevented degradation of canola oil, as measured by induction time, in a concentration-dependent manner. Although SECO demonstrated a trend for better protection than either SDG or polymer containing SDG, they were not significantly different (P > 0.01). There was also no significant difference between SECO or SDG and BHT, suggesting flaxseed lignans may be good alternatives to minimize rancidity in oil-based food products.

Lignans: Insight to Chemistry and Pharmacological Applications-An Overview

Lignans are widely distributed in the plant kingdom and have been found in species belonging to more than seventy families. These are found in several foods, mostly in seeds, beans and berries. Sesame seed lignans are perhaps best known for their positive health effects as antioxidants. In recent times, lignans attracted much interest in the researchers due to their wide range of biological applications and their utility as useful synthons. This review describes up to date developments in the lignan chemistry, with a more emphasis on their natural sources, methods developed for synthetic analogues and critical discussion on biological activities.

An update on bioactive plant lignans

Natural Product Reports, 2005

Lignans are a class of secondary plant metabolites produced by oxidative dimerization of two phenylpropanoid units. Although their molecular backbone consists only of two phenylpropane (C 6 -C 3 ) units, lignans show an enormous structural diversity. There is a growing interest in lignans and their synthetic derivatives due to applications in cancer chemotherapy and various other pharmacological effects. This review deals with lignans possessing anticancer, antioxidant, antimicrobial, anti-inflammatory and immunosuppressive activities, and comprises the data reported in more than 100 peer-reviewed articles, so as to highlight the recently reported bioactive lignans that could be a first step towards the development of potential new therapeutic agents.