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Therapeutic Potential of Secoisolariciresinol Diglucoside: a Plant Lignan

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Therapeutic Potential of Secoisolariciresinol Diglucoside: a Plant Lignan Available online at www.ijpsdr.com International Journal of Pharmaceutical Sciences and Drug Research 2012; 4(1): 15-18 Review Article ISSN 0975-248X Therapeutic Potential of Secoisolariciresinol Diglucoside: A Plant Lignan Dhaval Patel, Jitendra Vaghasiya, S. S. Pancholi, Arindam Paul* Babaria Institute of Pharmacy, Vadodara, Gujarat, India ABSTRACT Secoisolariciresinol diglucoside (SDG) is a plant lignan mainly found in dietary food and various plants. It belongs to a bioactive polyphenolic chemical class. SDG and its metabolites (mammalian enterolignan) are having various pharmacological activities, viz., antioxidant, partial agonist to estrogen receptor and inhibitor of tyrosine kinase and topoisomerase. Although, human studies are limited, its pharmacological actions explain its use in diabetes, atherosclerosis, breast cancer, colon cancer, prostate cancer and in cardiovascular disease. Keywords: Secoisolariciresinol diglucoside, plant lignan, polyphenols, antioxidant, tyrosine kinase inhibitor, topoisomerase inhibitor. INTRODUCTION Table I: Lignans in selected food [8-9] Secoisolariciresinol Plant lignans are biophenolic compounds and was first Food and foods group th diglucoside content (µg/g) identified in 19 Century from woody tissues of trees. Flaxseed 3699 Several hundreds of lignans have been documented since Seeds Sunflower 6.1 then in roots, stem, cereals, oilseeds, nuts, legumes and fruits. Caraway 2.21 [1] Nowadays, with the growing interest towards Pumpkin 213.7 Soybean 2.73 nutraceuticals, plant lignans are becoming important Legumes Peanut 3.33 therapeutically active class of compounds because of their Pigeon pea 0.5 putative beneficial health effect such as antitumor, Urad Dahl bean 2.4 antioxidant, both estrogenic and antiestrogenic activity [2] and Nuts Walnut 1.63 [3] Almond 1.07 protection against coronary heart disease. This plant Blackberry 37.1 lignans can be converted by intestinal bacteria into the Lingberry 15.1 mammalian lignan such as enterolignans, enterodiol and Berries Strawberry 12.1 enterolactone. [4-6] Cranberry 15.1 Red currant 1.6 Secoisolariciresinol diglucoside (SDG) and matairesinol are Oatmeal 0.1 the major lignans with traces of pinoresinol, lariciresinol and Oat bran 0.24 Cereals isolariciresinol found in roots, stem, cereals, oilseeds, nuts, Rye meal, whole grain 0.5 legumes and fruits. [1-2] Flax seed (Linum usitatissimum L.) is Rye bran 1.32 Broccoli 4.14 Vegetables the richest dietary source of lignans, with SDG as a major Garlic 3.79 compound (% yield being 0.37%), besides that sesame seed, Carrots 1.92 pumpkin seeds, cereals (triticle and wheat), leguminous plant Coffee and Arabica coffee (instant) 7.16 (lentils, soyabeans), fruits (pears, prunes) and certain Tea Green tea 24.6 vegetables (garlic, asparagus, carrot) also contain traces of Black tea 15.9 lignans, but concentration in flaxseed is about 1000 times as Bioavailability can be defined as the fraction of the ingested high as found in other food sources. [7] plant lignans that is absorbed and can be used for metabolic PHARMACOKINETICS OF PLANT LIGNANS process (internal exposure) and storage in the body. Following metabolism of plant lignans in the human colon, *Corresponding author: Dr. Arindam Paul, the metabolites, enterodiol and enterolactone reach the Professor & Head, Department of Pharmacology, Babaria circulation and target tissues. As metabolism is extensive, Institute of Pharmacy (BIT Campus), # NH-8, Varnama, enterodiol and enterolactone might be more important for Vadodara- 391240, Gujarat, India; Tel.: +91-9687567207; potential health effect. The bioavailability of lignans can be E-mail: [email protected] 15 Paul et al. / Therapeutic Potential of Secoisolariciresinol Diglucoside…..…… Fig. I: The possible metabolic pathway for transformation of plant lignans to enterolignans by colonic microflora. form (aglycone or conjugated) of plant lignan, chronic exposure, and other host related factor like age and gender. [10] Fig. III: Schematic overview of main bioavailability of lignans. Fig. II: Conversion of SDG by bacteria in colon. After consumption of SDG, a small fraction is absorbed as [11] [12-13] determined by several process: (a) Conversion of plant such in the small intestine , and excreted in urine. lignans to enterolignans in the human colon; (b) Absorption However, the largest fraction of the SDG is transported to of enterolignans from the colon, which determines whether colon and metabolized by intestinal flora (Fig. II). The or not enterolignans become available in blood circulation; importance of microflora in the metabolism of SDG was [14-15] (c) Distribution and metabolism, which determines whether studied in germfree rats. Although the intestinal metabolites reach the target tissues where they can be have bacteria play a crucial role in lignan metabolism, few studies an effect or further metabolized. Finally, (d) Enterolignans had been published that identify organism involved in lignan are excreted from the body via faeces or urine (Fig. III). breakdown. Two anaerobes (Peptostreptococcus and Various factors may influence lignan bioavailability such as Eubacterium) catalyze the demethylation and [16] intestinal microflora, antibiotic use, food matrix, type and dehydroxylation of SDG. Recently, two microorganisms IJPSDR January-March, 2012, Vol 4, Issue 1 (15-18) 16 Paul et al. / Therapeutic Potential of Secoisolariciresinol Diglucoside…..…… Peptostreptococcus productus and Eggerthella inta were women. [24, 35-38] It showed the suppression of mammary isolated that were able to demethylate and dehydroxylate tumorigenesis by its partial estrogenic activity, antioxidant SDG and pinoresinol. However, concentrations of activity or reduction of plasma insulin like growth factor-1. enterolactone are usually higher than enterodiol in humans. [38-41] Besides, its antioxidant and partial estrogenic activity of [17] One bacterial strain (ED-Mt61/PYCt-s6) was identified to SDG and enterolignans also affect to beta glucouronidase be responsible for transformation of enterodiol to activity, which may be the cause of protective effect against enterolactone. [18] colon cancer. It has been observed that pretreatment of SDG and majority of lignan converted to enterolignans are flaxseed decrease the risk of colon carcinogenesis, with absorbed by the large intestine into the blood stream or reduced total number of aberrant crypts and foci significantly directly excreted via faeces. Plasma enterodiol and by 41-53% and 48-57% respectively. [38, 42-43] Metabolites of enterolactone circulate either as glucouronide and sulfate SDG also appeared to influence steroid metabolism in- vitro, conjugates or as free forms. [19] They are excreted via urine or not only by acting on steroid receptor but also by steroid bile, in urine; enterodiol and enterolactone are excreted in metabolism, for e.g. sex hormone binding globulin synthesis conjugated forms; primarily as monoglucouronides (85 and [44-45] 5α-reductase and 17-β hydroxyl-steroid dehydrogenase. 95% respectively) with small percentage being excreted as [46] On the virtue of these all property and inhibition of monosulfates (2-10%) and free aglycones (0.3-1%). [20-21] tyrosine kinase and topoisomerase contribute the lower Conjugated enterolignans that are excreted via bile can incidence of prostate cancer. [47] undergo enterohepatic circulation (i.e. excreted through bile Anti-diabetic activity: It has been demonstrated that SDG duct into the intestinal tract, further metabolized in the colon, prevented development of diabetes mellitus by 75%. The and reabsorbed from the large intestine into the bloodstream). reactive oxygen species play an important role in [15, 22] The mean residence time and half lives measured after development of debates mellitus (DM) therefore it was single dose of SDG (0.9 mg SDG/kg bodyweight) in healthy suggested that the antioxidant activity may be playing role men and women indicates that enterolignan accumulate in for its antidiabetic activity. [48-49] plasma when consumed 2-3 times a day and reach steady Effect on Cardiovascular system: There are several state. [23] mechanisms by which SDG protect against cardiovascular diseases. It appeared beneficial role in endotoxic shock. [25, 50] PHARMACOLOGICAL ACTIVITIES OF Apart from reducing cholesterol level it also induced SECOISOLARICIRESINOL DIGLUCOSIDE (SDG) angiogenesis mediated cardioprotection by increased Antioxidant activity: The plant lignans demonstrated neovascularization in the peri-infarct zone, leading to less extreme radical scavenging activity. In both lipid and ventricular remodeling. Thus, SDG is a great clinical aqueous, in-vitro model systems SDG and its metabolites potential for treatment of ischemic heart disease. [51] appeared as antioxidant. All three lignans significantly inhibited the linoleic acid peroxidation at 10 and 100µM over REFERENCES a 24-48 h of incubation at 40°C. [24-25] However, it has been 1. Willtor SM, Smeds AI, Holmbom BR. Chromatographic analysis of demonstrated that enterodiol and enterolactone were not Lignans (Review). J Chromatography A. 2006; 1112:64-77. 2. Sicilia T, Niemeyer HB, Honig DM, Metzler M. Identification and effective in preventing H2O2 induced DNA damage in HT-29 stereochemical characterization of lignans in flaxseed and pumpkin cells and enterolactone did not reduced intracellular oxidative seeds. J Agri Food Chem. 2003; 51:1181-1118. stress at similar concentration. [26] 3. Smeds AI, Eklund PC, Sjoholm RE, Willfer SM,
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