THERAPEUTIC POTENTIAL OF SECOISOLARICIRESINOL DIGLUCOSIDE: A PLANT LIGNAN
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 inhibitorDOI
https://doi.org/10.25004/IJPSDR.2012.040103References
1. Willtor SM, Smeds AI, Holmbom BR. Chromatographic analysis of Lignans (Review). J Chromatography A. 2006; 1112:64-77.
2. Sicilia T, Niemeyer HB, Honig DM, Metzler M. Identification and stereochemical characterization of lignans in flaxseed and pumpkin seeds. J Agri Food Chem. 2003; 51:1181-1118.
3. Smeds AI, Eklund PC, Sjoholm RE, Willfer SM, Nishibe S, Deyama T. Quantification of a broad spectrum of lignans in cereals, oil seeds and nuts. J Agri Food Chem. 2007; 55:1337-1346.
4. Axelson M, Sjoevall J, Gustafsson BE. Origin of lignans in mammals and identification of precursor from plants. Nature.1982; 298:659-660.
5. Borriello SP, Setchell KD, Axelson M, Lawson AM. Production and metabolism of lignans by the human faecal flora. J Appl Bacteriol. 1985; 58:37-43.
6. Mazur WM, Uehara M, Wahala K, Adlercreutz H. Phytoestrogen content of berries and plasma concentration and urinary excretion of enterolactone after a single strawberry-meal in human subjects. Br J Nutrition. 2000; 83:381-387.
7. Milder IEJ, Arts ICW, Putte B, Venema DP, Hollman PCH. Lignan content of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol. Br J Nutrition. 2005; 93:393.
8. Adlercreutz H, Mazur W. Phytoestrogen and western disease. Ann. Med. 1997; 29:95-120.
9. Mazur W. Phytoestrogen contents in food. Baillieres Clin Endocrinol Metab. 1998; 12:729-42.
10. Rowald l, Faughnan M, Hoey L, Wahala K. Williamson G, Cassidy A. Bioavailability of Phytoestrogens. Br J Nutr. 2003; 89(Suppl): 838-852.
11. Penalvo J L, Nurmi T, Haajnen K, Al-Maharik N. Determination of lignans in human plasma by liquid chromatography with coulometric electrode array detection. Anal Biochem. 2004; 332:384-393.
12. Nurmi T, Voutilainen S, Nyyssonen K, Adlercreutz H, Salonen JT. Liquid chromatography method for plant and mammalian lignans in human urine. J Chromatography B. 2003; 798:101-110.
13. Bannwart C, Adlercreutz H, Wahala K, Brunow G, Hase T. Detection and identification of the plant lignans lariciresinol, isolariciresinol and secoisolariciresinol in human urine. Clin Chimica Acta.1989; 180:293-301.
14. Bowey E, Adlercreutz H, Rowland l. Metabolism of isoflavones and lignans by the gut microflora: a study in germ free and human flora associated rats. Food Chem Toxicol. 2003; 41:631-636.
15. Axelson M, Setchell KD. The excretion of the lignans in rats evidence for an intestinal bacterial source for this new group of compounds. FEBS Lett.1981; 123:337-342.
16. Wang LQ, Meselhy MR, Li Y, Quin GW, Hattori M. Human intestinal bacteria capable of transforming secoisolariciresinol diglucoside to mammalian lignans, enterodiol and enterolactone. Chem Pharm Bull. 2000; 48:1606-1610.
17. Clavel T, Henderson G, Alpert CA, Philippe C, Rigotter-Gois L, Dore J, Blaut M. Intestinal bacteria communities that produce active estrogen like compounds enterodiol and enterolactone in humans. Appl Environ Microbiol. 2005; 71:6077-6085.
18. Clavel T, Henderson G, Engest W, Dore J, Blaut M. Phylogeny of human intestinal bactaria that activate the dietary lignans secoisolariciresinol diglucoside. FEMS Microbiol Ecol. 2006; 55:471-478.
19. Adlercreutz H, Fotsis T, Lampe J, Wahala K, Makela T, Brunow G, Hase T. Quantitative determination of lignans and isoflavonoids in plasma of omnivorous and vegetarian women by isotope dilution gas chromatography – mass spectrometry. Scandinavian J Clin Lab Invest. 1993; 215:5-18.
20. Adlercreutz H, Vanderwildt J, Kinzel J, Attalla H, Wahala K, Makela T, Hase T, Fotsis T. Lignans and isoflavonoids conjugates in human urine. J Steroid Biochem Mol Biol. 1995; 25:97-103.
21. Axelson M, Setchell KD. Conjugation of lignans in human urine. FEBS Letters. 1980; 122:49-53.
22. Knudsen KEB, Serena A, Kjaer AKB, Tetens L, Heinonen SM, Nurmi T, Adlercreutz H. Rye bread in the diet of pigs enhances the formation of enterolactone and increase its levels in plasma, urine and feces. J Nutrition. 2003; 133:1368-1375.
23. Anneleen K, Iija CWA, Tom BV, Peter CHH. Pharmacokinetics of enterolignans in healthy men and women consuming a single dose of secoisolariciresinol diglucoside. J Nutrition. 2005; 135:795-801.
24. Kitts DD, Vyan YV, Wijewickreme AN, Thompson LU. Antioxidant property of flaxseed lignans SDG and its mammalian lignan metabolites enterodiol and enterolactone. Mol Cell Biochem. 1999; 202:91-100.
25. Prasad K. Antioxidant activity of secoisolariciresinol diglucoside derived metabolites enterodiol and enterolactone. International J Angiol. 2000; 9:220-225.
26. Pool-Zobel BL, Adlercreutz H, Glei M, Liegibel UM, Sittlingon J, Rowland I, Wahala K, Rechkemmer G. Isoflavonoid and lignans have different potential to modulate oxidative genetic damage in human colon cells. Carcinogenesis. 2000; 21:1247-1252.
27. Ogborn MR, Nitschmann E, Weiler HA. Flaxseed ameliorates intestinal nephritis in rat polycystic kidney disease. Kidney Int. 1919; 55:417-423.
28. Prasad K. Dietary flaxseed in prevention of hypercholesterolemic atherosclerosis. Atherosclerosis. 1997; 132:69-76.
29. Prasad K. Reduction of serum cholesterol and hypercholesterolemic atherosclerosis in rabbit by secoisolariciresinol diglucoside isolated from flaxseed. Circulation. 1999; 99:1355-1362.
30. Prasad K. Hypercholesterolemic and antiatherosclerotic effect of flax lignan complex isolated from flaxseed. Atherosclerosis. 2005; 179:269-275.
31. Serraino M, Thompson LU. The effect of flaxseed supplementation on early risk markers for mammary carcinogenesis. Cancer Lett. 1991; 60:135-142.
32. Serraino M, Thompson LU. The effect of flaxseed supplementation on the initiation and promotional stages of mammary tumorigenesis. Nutrition Cancer. 1992; 17:153-159.
33. Muller SO, Simon S, Chae K, Metzler M, Korach KS. Phytoestrogens and their human metabolites show distinct agonistic and antagonistic properties on estrogen receptor α and β in human cells. Toxicol Sci. 2004; 80:14-25.
34. Wang LQ. Mammalian phytoestrogens: enterodiol and enterolactone. J Chromatography B. 2002; 777:289-309.
35. Haggans CJ, Olson BA, Thomul W. Effect of flaxseed consumption on urinary estrogen metabolites in postmenopausal women. Nutrition Cancer. 1919; 33:188-195.
36. Tou JCL, Thompson LU. Exposure to flaxseed or its lignans components during different developmental stages influences rat mammary gland structures. Carcinogenesis. 1999; 20:1831-1835.
37. Tou JCL, Chen J, Thompson LU. Flaxseed and its lignan precursor, secoisolariciresnol diglucoside affect pregnancy outcome and reproductive development in rats. J Nutrition. 1998; 128:1861-1868.
38. Sung MK, Lautens M, Thompson LU. Mammalian lignan inhibit the growth of estrogen-independent human colon tumor cells. Anticancer Res. 1998; 18:1405-1408.
39. Rickard SE, Yuan YV, Chen J, Thompson LU. Dose effect of flaxseed and its lignan on N-methyl-N-nitrosourea induced mammary tumorigenesis in rats. Nutrition Cancer. 1999; 35:50-57.
40. Thompson LU, Seidl MM, Rickard SE, Orcheson LJ, Fong HHS. Antitumorigenic effect of mammalian lignan precursor from flaxseed. Nutrition Cancer. 1996; 26:159-165.
41. Thompson LU, Rickard SE, Orcheson LJ, Seidl MM. Flaxseed and its lignan and oil component reduce mammary tumor growth at late stage of carcinogenesis. Carcinogenesis. 1996; 17:1373-1376.
42. Serraino M, Thompson LU. Flaxseed supplementation and early markers of colon carcinogenesis. Cancer Lett. 1992; 63:159-165.
43. Jenab M, Thompson LU. The influence of flaxseed and lignans on colon carcinogenesis and beta-glucuronidase activity. Carcinogenesis. 1996; 17:1343-1348.
44. Schottner M, Gansser D, Spiteller G. Interaction of lignan with human sex hormone binding globulin (SHBG). J Biosci. 1997; 52:834-843.
45. Adlercreutz H, Hockerstedt K, Bannwart C. A effect of dietary components, including lignan and phytoestrogens on enterohepatic circulation and liver metabolism of estrogen and on sex hormone binding globulin (SHBG). J Steroid Biochem Mol Biol. 1987; 27:1135-1144.
46. Evans BAJ, Grifftiths K, Morton MS. Inhibition of 5α-reductase in genital skin fibroblast and prostate tissue by dietary lignans and isoflavonoids. J Endocrinol. 1995; 147:295-302.
47. Tou JCL, Chen J, Thompson LU. Dose, timing and duration of flaxseed exposure alter reproductive indices and sex hormone in rats. J Toxicol Environ Health. 1990; 56:555-570.
48. Prasad K. Oxidative stress as a mechanism of diabetes BB Prone rats: effect of SDG. Mol Cell Biochem. 2000; 209:89-96.
49. Prasad K, Mantha SV, Muir AD, Westcott ND. Protective effect of secoisolariciresinol diglucoside against streptozotocin induced diabetes and its mechanism. Mol Cell Biochem. 2000; 206:141-150.
50. Pattanik U, Prasad K. Oxygen free radicals and endotoxic shock: effect of flaxseed. J Cardiovascular Pharmacol Ther. 1998; 3:305-318.
51. Penumathsa SV, Koneru S, Mahesh TV, Zhan L, Prasad K. Secoisolariciresinol diglucoside: Relevance to angiogenesis and cardioprotection against ischemia-reperfusion injury. J Pharmacol Exp Ther. 2007; 320:951-959.
2. Sicilia T, Niemeyer HB, Honig DM, Metzler M. Identification and stereochemical characterization of lignans in flaxseed and pumpkin seeds. J Agri Food Chem. 2003; 51:1181-1118.
3. Smeds AI, Eklund PC, Sjoholm RE, Willfer SM, Nishibe S, Deyama T. Quantification of a broad spectrum of lignans in cereals, oil seeds and nuts. J Agri Food Chem. 2007; 55:1337-1346.
4. Axelson M, Sjoevall J, Gustafsson BE. Origin of lignans in mammals and identification of precursor from plants. Nature.1982; 298:659-660.
5. Borriello SP, Setchell KD, Axelson M, Lawson AM. Production and metabolism of lignans by the human faecal flora. J Appl Bacteriol. 1985; 58:37-43.
6. Mazur WM, Uehara M, Wahala K, Adlercreutz H. Phytoestrogen content of berries and plasma concentration and urinary excretion of enterolactone after a single strawberry-meal in human subjects. Br J Nutrition. 2000; 83:381-387.
7. Milder IEJ, Arts ICW, Putte B, Venema DP, Hollman PCH. Lignan content of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol. Br J Nutrition. 2005; 93:393.
8. Adlercreutz H, Mazur W. Phytoestrogen and western disease. Ann. Med. 1997; 29:95-120.
9. Mazur W. Phytoestrogen contents in food. Baillieres Clin Endocrinol Metab. 1998; 12:729-42.
10. Rowald l, Faughnan M, Hoey L, Wahala K. Williamson G, Cassidy A. Bioavailability of Phytoestrogens. Br J Nutr. 2003; 89(Suppl): 838-852.
11. Penalvo J L, Nurmi T, Haajnen K, Al-Maharik N. Determination of lignans in human plasma by liquid chromatography with coulometric electrode array detection. Anal Biochem. 2004; 332:384-393.
12. Nurmi T, Voutilainen S, Nyyssonen K, Adlercreutz H, Salonen JT. Liquid chromatography method for plant and mammalian lignans in human urine. J Chromatography B. 2003; 798:101-110.
13. Bannwart C, Adlercreutz H, Wahala K, Brunow G, Hase T. Detection and identification of the plant lignans lariciresinol, isolariciresinol and secoisolariciresinol in human urine. Clin Chimica Acta.1989; 180:293-301.
14. Bowey E, Adlercreutz H, Rowland l. Metabolism of isoflavones and lignans by the gut microflora: a study in germ free and human flora associated rats. Food Chem Toxicol. 2003; 41:631-636.
15. Axelson M, Setchell KD. The excretion of the lignans in rats evidence for an intestinal bacterial source for this new group of compounds. FEBS Lett.1981; 123:337-342.
16. Wang LQ, Meselhy MR, Li Y, Quin GW, Hattori M. Human intestinal bacteria capable of transforming secoisolariciresinol diglucoside to mammalian lignans, enterodiol and enterolactone. Chem Pharm Bull. 2000; 48:1606-1610.
17. Clavel T, Henderson G, Alpert CA, Philippe C, Rigotter-Gois L, Dore J, Blaut M. Intestinal bacteria communities that produce active estrogen like compounds enterodiol and enterolactone in humans. Appl Environ Microbiol. 2005; 71:6077-6085.
18. Clavel T, Henderson G, Engest W, Dore J, Blaut M. Phylogeny of human intestinal bactaria that activate the dietary lignans secoisolariciresinol diglucoside. FEMS Microbiol Ecol. 2006; 55:471-478.
19. Adlercreutz H, Fotsis T, Lampe J, Wahala K, Makela T, Brunow G, Hase T. Quantitative determination of lignans and isoflavonoids in plasma of omnivorous and vegetarian women by isotope dilution gas chromatography – mass spectrometry. Scandinavian J Clin Lab Invest. 1993; 215:5-18.
20. Adlercreutz H, Vanderwildt J, Kinzel J, Attalla H, Wahala K, Makela T, Hase T, Fotsis T. Lignans and isoflavonoids conjugates in human urine. J Steroid Biochem Mol Biol. 1995; 25:97-103.
21. Axelson M, Setchell KD. Conjugation of lignans in human urine. FEBS Letters. 1980; 122:49-53.
22. Knudsen KEB, Serena A, Kjaer AKB, Tetens L, Heinonen SM, Nurmi T, Adlercreutz H. Rye bread in the diet of pigs enhances the formation of enterolactone and increase its levels in plasma, urine and feces. J Nutrition. 2003; 133:1368-1375.
23. Anneleen K, Iija CWA, Tom BV, Peter CHH. Pharmacokinetics of enterolignans in healthy men and women consuming a single dose of secoisolariciresinol diglucoside. J Nutrition. 2005; 135:795-801.
24. Kitts DD, Vyan YV, Wijewickreme AN, Thompson LU. Antioxidant property of flaxseed lignans SDG and its mammalian lignan metabolites enterodiol and enterolactone. Mol Cell Biochem. 1999; 202:91-100.
25. Prasad K. Antioxidant activity of secoisolariciresinol diglucoside derived metabolites enterodiol and enterolactone. International J Angiol. 2000; 9:220-225.
26. Pool-Zobel BL, Adlercreutz H, Glei M, Liegibel UM, Sittlingon J, Rowland I, Wahala K, Rechkemmer G. Isoflavonoid and lignans have different potential to modulate oxidative genetic damage in human colon cells. Carcinogenesis. 2000; 21:1247-1252.
27. Ogborn MR, Nitschmann E, Weiler HA. Flaxseed ameliorates intestinal nephritis in rat polycystic kidney disease. Kidney Int. 1919; 55:417-423.
28. Prasad K. Dietary flaxseed in prevention of hypercholesterolemic atherosclerosis. Atherosclerosis. 1997; 132:69-76.
29. Prasad K. Reduction of serum cholesterol and hypercholesterolemic atherosclerosis in rabbit by secoisolariciresinol diglucoside isolated from flaxseed. Circulation. 1999; 99:1355-1362.
30. Prasad K. Hypercholesterolemic and antiatherosclerotic effect of flax lignan complex isolated from flaxseed. Atherosclerosis. 2005; 179:269-275.
31. Serraino M, Thompson LU. The effect of flaxseed supplementation on early risk markers for mammary carcinogenesis. Cancer Lett. 1991; 60:135-142.
32. Serraino M, Thompson LU. The effect of flaxseed supplementation on the initiation and promotional stages of mammary tumorigenesis. Nutrition Cancer. 1992; 17:153-159.
33. Muller SO, Simon S, Chae K, Metzler M, Korach KS. Phytoestrogens and their human metabolites show distinct agonistic and antagonistic properties on estrogen receptor α and β in human cells. Toxicol Sci. 2004; 80:14-25.
34. Wang LQ. Mammalian phytoestrogens: enterodiol and enterolactone. J Chromatography B. 2002; 777:289-309.
35. Haggans CJ, Olson BA, Thomul W. Effect of flaxseed consumption on urinary estrogen metabolites in postmenopausal women. Nutrition Cancer. 1919; 33:188-195.
36. Tou JCL, Thompson LU. Exposure to flaxseed or its lignans components during different developmental stages influences rat mammary gland structures. Carcinogenesis. 1999; 20:1831-1835.
37. Tou JCL, Chen J, Thompson LU. Flaxseed and its lignan precursor, secoisolariciresnol diglucoside affect pregnancy outcome and reproductive development in rats. J Nutrition. 1998; 128:1861-1868.
38. Sung MK, Lautens M, Thompson LU. Mammalian lignan inhibit the growth of estrogen-independent human colon tumor cells. Anticancer Res. 1998; 18:1405-1408.
39. Rickard SE, Yuan YV, Chen J, Thompson LU. Dose effect of flaxseed and its lignan on N-methyl-N-nitrosourea induced mammary tumorigenesis in rats. Nutrition Cancer. 1999; 35:50-57.
40. Thompson LU, Seidl MM, Rickard SE, Orcheson LJ, Fong HHS. Antitumorigenic effect of mammalian lignan precursor from flaxseed. Nutrition Cancer. 1996; 26:159-165.
41. Thompson LU, Rickard SE, Orcheson LJ, Seidl MM. Flaxseed and its lignan and oil component reduce mammary tumor growth at late stage of carcinogenesis. Carcinogenesis. 1996; 17:1373-1376.
42. Serraino M, Thompson LU. Flaxseed supplementation and early markers of colon carcinogenesis. Cancer Lett. 1992; 63:159-165.
43. Jenab M, Thompson LU. The influence of flaxseed and lignans on colon carcinogenesis and beta-glucuronidase activity. Carcinogenesis. 1996; 17:1343-1348.
44. Schottner M, Gansser D, Spiteller G. Interaction of lignan with human sex hormone binding globulin (SHBG). J Biosci. 1997; 52:834-843.
45. Adlercreutz H, Hockerstedt K, Bannwart C. A effect of dietary components, including lignan and phytoestrogens on enterohepatic circulation and liver metabolism of estrogen and on sex hormone binding globulin (SHBG). J Steroid Biochem Mol Biol. 1987; 27:1135-1144.
46. Evans BAJ, Grifftiths K, Morton MS. Inhibition of 5α-reductase in genital skin fibroblast and prostate tissue by dietary lignans and isoflavonoids. J Endocrinol. 1995; 147:295-302.
47. Tou JCL, Chen J, Thompson LU. Dose, timing and duration of flaxseed exposure alter reproductive indices and sex hormone in rats. J Toxicol Environ Health. 1990; 56:555-570.
48. Prasad K. Oxidative stress as a mechanism of diabetes BB Prone rats: effect of SDG. Mol Cell Biochem. 2000; 209:89-96.
49. Prasad K, Mantha SV, Muir AD, Westcott ND. Protective effect of secoisolariciresinol diglucoside against streptozotocin induced diabetes and its mechanism. Mol Cell Biochem. 2000; 206:141-150.
50. Pattanik U, Prasad K. Oxygen free radicals and endotoxic shock: effect of flaxseed. J Cardiovascular Pharmacol Ther. 1998; 3:305-318.
51. Penumathsa SV, Koneru S, Mahesh TV, Zhan L, Prasad K. Secoisolariciresinol diglucoside: Relevance to angiogenesis and cardioprotection against ischemia-reperfusion injury. J Pharmacol Exp Ther. 2007; 320:951-959.
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01-01-2012
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“THERAPEUTIC POTENTIAL OF SECOISOLARICIRESINOL DIGLUCOSIDE: A PLANT LIGNAN”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 4, no. 1, Jan. 2012, pp. 15-18, https://doi.org/10.25004/IJPSDR.2012.040103.
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“THERAPEUTIC POTENTIAL OF SECOISOLARICIRESINOL DIGLUCOSIDE: A PLANT LIGNAN”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 4, no. 1, Jan. 2012, pp. 15-18, https://doi.org/10.25004/IJPSDR.2012.040103.
