Soyabean glyceollins: Biological effects and relevance to human health

Proceedings of the Nutrition Society

Volumn 71, Issue 1, 2012, Pages 166-174

  Kim, Hyo Jung ^a   Lim, Ji Sun ^a   Kim, Woo Keun ^b   Kim, Jong Sang ^a  

^a Kyungpook National University   (South Korea)

^b Korea Institute of Toxicology   (South Korea)

Author keywords

Anti cancer activity; Anti inflammatory activity; Antioxidants; Glyceollins; Soyabean

Indexed keywords

ANTIINFLAMMATORY AGENT; ANTINEOPLASTIC AGENT; ANTIOXIDANT; DAIDZEIN; GLUTATHIONE REDUCTASE; GLUTATHIONE TRANSFERASE A1; GLYCEOLLIN; HEME OXYGENASE 1; KELCH LIKE ECH ASSOCIATED PROTEIN 1; MELANIN; PHYTOALEXIN; REACTIVE OXYGEN METABOLITE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE OXIDASE; TRANSCRIPTION FACTOR NRF2; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ATHEROSCLEROSIS; BREAST CANCER; CANCER CELL; CANCER MODEL; CARDIOVASCULAR EFFECT; CELL MIGRATION; CELL PROLIFERATION; CONFERENCE PAPER; DRUG EFFECT; DRUG MECHANISM; FUNGUS; HUMAN; INSULIN LIKE ACTIVITY; MACROPHAGE; NONHUMAN; PLANT FUNGUS INTERACTION; PROSTATE CANCER; SKIN COLOR; SMOOTH MUSCLE FIBER; SOYBEAN; TUMOR XENOGRAFT;

ANIMALS; ANTI-INFLAMMATORY AGENTS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; ANTIOXIDANTS; ATHEROSCLEROSIS; BREAST NEOPLASMS; ESTROGEN ANTAGONISTS; FEMALE; HUMANS; MALE; PHYTOTHERAPY; PLANT EXTRACTS; PROSTATIC NEOPLASMS; PTEROCARPANS; SESQUITERPENES; SOYBEANS;

ANIMALIA; FUNGI;

EID: 84863077336     PISSN: 00296651     EISSN: 14752719     Source Type: Journal    
DOI: 10.1017/S0029665111003272     Document Type: Conference Paper

References (87)

1. Jeandet P, Douillet-Breuil AC, Bessis R et al. (2002) Phytoalexins from the Vitaceae: biosynthesis, phytoalexin gene expression in transgenic plants, antifungal activity, and metabolism. J Agric Food Chem 50, 2731-2741. (Pubitemid 34493577)
2. Dixon RA (2001) Natural products and plant disease resistance. Nature 411, 843-847. (Pubitemid 32588112)
3. Paxton JD (1980) A new working definition of the term "phytoalexin". Plant Dis 64, 734.
4. Paxton JD (1981) Phytoalexins-a working redefinition. J Phytopathol 101, 106-109.
5. VanEtten HD, Mansfield JW, Bailey JA et al. (1984) Two classes of plant antibiotics: phytoalexins versus "phytoanticipins". Plant Cell 6, 1191-1192.
6. Feng S, Saw CL, Lee YK et al. (2008) Novel process of fermenting black soybean [Glycine max (L.) Merrill] yogurt with dramatically reduced flatulence-causing oligosaccharides but enriched soy phytoalexins. J Agric Food Chem 56, 10078-10084.
7. Jang M, Cai L, Udeani GO et al. (1997) Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 275, 218-220. (Pubitemid 127696281)
8. Harikumar KB & Aggarwal BB (2008) Resveratrol: a multitargeted agent for age-associated chronic diseases. Cell Cycle 7, 1020-1035.
9. Baur JA, Pearson KJ, Price NL et al. (2006) Resveratrol improves health and survival of mice on a high-calorie diet. Nature 444, 337-342. (Pubitemid 44764104)
10. Dolinsky VW & Dyck JR. (2011) Calorie restriction and resveratrol in cardiovascular health and disease. Biochim Biophys Acta 812, 1477-1489.
11. Kim HJ, di Luccio E, Kong AN et al. (2011) Nrf2-mediated induction of phase 2 detoxifying enzymes by glyceollins derived from soybean exposed to Aspergillus sojae. Biotechnol J 6, 525-536.
12. Kim HJ, Suh HJ, Kim JH et al. (2010) Estrogenic activity of glyceollins isolated from soybean elicited with Aspergillus sojae. J Med Food 13, 382-390.
13. Kim HJ, Suh HJ, Kim JH et al. (2010) Antioxidant activity of glyceollins derived from soybean elicited with Aspergillus sojae. J Agric Food Chem 58, 11633-11638.
14. Burow ME, Boue SM, Collins-Burow BM et al. (2001) Phytochemical glyceollins, isolated from soy, mediate antihormonal effects through estrogen receptor a and b. J Clin Endocrinol Metab 86, 1750-1758. (Pubitemid 32377291)
15. Salvo VA, Boue SM, Fonseca JP et al. (2006) Antiestrogenic glyceollins suppress human breast and ovarian carcinoma tumorigenesis. Clin Cancer Res 12, 159-164.
16. Wood CE, Clarkson TB, Appt SE et al. (2006) Effects of soybean glyceollins and estradiol in postmenopausal female monkeys. Nutr Cancer 56, 74-81. (Pubitemid 46173416)
17. Dong JY & Qin LQ. (2011) Soy isoflavones consumption and risk of breast cancer incidence or recurrence: a meta-analysis of prospective studies. Breast Cancer Res Treat 125, 315-23.
18. Taylor CK, Levy RM, Elliott JC et al. (2009) The effect of genistein aglycone on cancer and cancer risk: a review of in vitro, preclinical, and clinical studies. Nutr Rev 67, 398-415.
19. Hwang YW, Kim SY, Jee SH et al. (2009) Soy food consumption and risk of prostate cancer: a meta-analysis of observational studies. Nutr Cancer 61, 98-606.
20. Messina M (2010) Insights gained from 20 years of soy research. J Nutr 140, 2289S-2295S.
21. Dakora FD & Phillips DA (1996) Diverse functions of isoflavonoids in legumes transcend anti-microbial definitions of phytoalexins Physiol Mol Plant Pathol 49, 1-20. (Pubitemid 26350850)
22. Farmakalidis E & Murphy PA (1985) Isolation of 60-Oacetyldaidzein and 60-O-acetylgenistein from toasted defatted soy flakes. J Agric Food Chem 33, 385-389.
23. Kudou S, Fleury Y, Welt D et al. (1991) Malonyl isoflavone glycosides in soybean seeds (Glycine max Merrill). Agric Biol Chem 55, 2227-2233.
24. Barnes S, Kirk M & Coward L (1994) Isoflavones and their conjugates in soy foods: extraction conditions and analysis by HPLC-mass spectrometry. J Agric Food Chem 42, 2466-2474.
25. Setchell KD (1998) Phytoestrogens: the biochemistry, physiology, and implications for human health of soy isoflavones. Am J Clin Nutr 68, 1333S-1346S. (Pubitemid 28550909)
26. Kraus C, Spiteller G, Mithöfer A et al. (1995) Quantification of glyceollins in nonelicited seedlings of Glycine max by gas chromatography-mass spectrometry. Phytochemistry 40, 739-743.
27. Akashi T, Sasaki K, Aoki T et al. (2009) Molecular cloning and characterization of a cDNA for pterocarpan 4-dimethylallyltransferase catalyzing the key prenylation step in the biosynthesis of glyceollin, a soybean phytoalexin. Plant Physiol 149, 683-693.
28. Tilghman SL, Boué SM & Burow ME (2010) Glyceollins, a novel class of antiestrogenic phytoalexins. Mol Cell Pharmacol 2, 155-160.
29. Boue SM, Tilghman SL, Elliott S et al. (2009) Identification of the potent phytoestrogen glycinol in elicited soybean (Glycine max). Endocrinology 150, 2446-2453.
30. Banks SW & Dewick PM (1993) Biosynthesis of glyceollins I, II, and III in soybean. Phytochemistry 22, 2729-2733.
31. Lee MR, Kim JY, Chun J et al. (2011) Induction of glyceollins by fungal infection in varieties of Korean soybean. J Microbiol Biotechnol 20, 1226-1229.
32. Smith DA & Banks SW (1986) Biosynthesis, elicitation and biological activity of isoflavonoid phytoalexins. Phytochemistry 25, 979-995.
33. Gore RS & Miller KJ (1993) Cyclic [b]-1,6-1,3 glucans are synthesized by Bradyrhizobium japonicum bacteroids within soybean (Glycine max) root nodules. Plant Physiol 102, 191-194.
34. Miller KJ, Hadley JA & Gustine DL (1994) Cyclic [b]-1,6-1,3-glucans of Bradyrhizobium japonicum USDA 110 elicit isoflavonoid production in the soybean (Glycine max) host. Plant Physiol 104, 917-923.
35. Kim HJ, Suh HJ, Lee CH et al. (2010) Antifungal activity of glyceollins isolated from soybean elicited with Aspergillus sojae. J Agric Food Chem 58, 9483-9487.
36. Keen NT & Bruegger B (1977) Phytoalexins and chemicals that elicit their production in plants. ACS Symp Ser 62, 1-26.
37. Halliwell B (2007) Biochemistry of oxidative stress. Biochem Soc Trans 35, 1147-1150.
38. Sies H (1991) Oxidative stress: from basic research to clinical application. Am J Med 91, 31S-38S.
39. Markesbery WR (1999) The role of oxidative stress in Alzheimer disease. Arch Neurol 56, 1449-1452.
40. Finkel T & Holbrook NJ (2000) Oxidants, oxidative stress and the biology of ageing. Nature 408, 239-247.
41. Kensler TW, Wakabayashi N & Biswal S (2007) Cell survival responses to environmental stresses via the Keap1-Nrf2-ARE pathway. Annu Rev Pharmacol Toxicol 47, 89-116.
42. Itoh K, Chiba T, Takahashi S, Ishii T et al. (1997) An Nrf2 small Maf heterodimer mediates the induction of phase II detoxifying enzyme genes through antioxidant response elements. Biochem Biophys Res Commun 236, 313-322. (Pubitemid 27373291)
43. Dinkova-Kostova AT, Massiah MA, Bozak RE et al. (2001) Potency of Michael reaction acceptors as inducers of enzymes that protect against carcinogenesis depends on their reactivity with sulfhydryl groups. Proc Natl Acad Sci USA 2001, 98, 3404-3409. (Pubitemid 32220858)
44. Jeong WS, Jun M & Kong AN (2006) Nrf2: a potential molecular target for cancer chemoprevention by natural compounds. Antioxid Redox Signal 8, 99-106. (Pubitemid 43324535)
45. Kobayashi M, Li L, Iwamoto N et al. (2009) The antioxidant defense system Keap1-Nrf2 comprises a multiple sensing mechanism for responding to a wide range of chemical compounds. Mol Cell Biol 29, 493-502.
46. Ogura T, Tong KI, Mio K et al. (2010) Keap1 is a forkedstem dimer structure with two large spheres enclosing the intervening, double glycine repeat, and C-terminal domains. Proc Natl Acad Sci USA 107, 2842-2847.
47. Sun Z, Huang Z & Zhang DD (2009) Phosphorylation of Nrf2 at multiple sites by MAP kinases has a limited contribution in modulating the Nrf2-dependent antioxidant response. PLoS One 4, e6588.
48. Nakaso K, Yano H, Fukuhara Y et al. (2003) PI3K is a key molecule in the Nrf2-mediated regulation of antioxidative proteins by hemin in human neuroblastoma cells. FEBS Lett 546, 181-184. (Pubitemid 36782407)
49. Lim JH, Kim KM, Kim SW et al. (2008) Bromocriptine activates NQO1 via Nrf2-PI3K/Akt signaling: novel cytoprotective mechanism against oxidative damage. Pharmacol Res 57, 325-331.
50. Wakabayashi N, Itoh K, Wakabayashi J et al. (2003) Keap1-null mutation leads to postnatal lethality due to constitutive Nrf2 activation. Nat Genet 35, 238-245. (Pubitemid 37363177)
51. Okawa H, Motohashi H, Kobayashi A et al. (2006) Hepatocyte-specific deletion of the Keap1 gene activates Nrf2 and confers potent resistance against acute drug toxicity. Biochem Biophys Res Commun 339, 79-88. (Pubitemid 41697517)
52. Osburn WO, Yates MS, Dolan PD et al. (2008) Genetic or pharmacologic amplification of nrf2 signaling inhibits acute inflammatory liver injury in mice. Toxicol Sci 104, 218-227. (Pubitemid 351859044)
53. Halliwell B (1992) Reactive oxygen species and the central nervous system. J Neurochem 59, 1609-1623.
54. Gutteridge JM & Halliwell B (2010) Antioxidants: molecules, medicines, and myths. Biochem Biophys Res Commun 393, 561-564.
55. Yu X & Kensler T (2005) Nrf2 as a target for cancer chemoprevention. Mutat Res 591, 93-102. (Pubitemid 41654841)
56. Lee JS & Surh YJ (2005) Nrf2 as a novel molecular target for chemoprevention. Cancer Lett 224, 171-184.
57. Kwak MK, Wakabayashi N & Kensler TW (2004) Chemoprevention through the Keap1-Nrf2 signaling pathway by phase 2 enzyme inducers. Mutat Res 555, 133-148. (Pubitemid 39345402)
58. Seo JY, Park J, Kim HJ et al. (2009) Isoalantolactone from Inula helenium caused Nrf2-mediated induction of detoxifying enzymes. J Med Food 12, 1038-1045.
59. Lundberg IE (2000) The role of cytokines, chemokines, and adhesion molecules in the pathogenesis of idiopathic inflammatory myopathies. Curr Rheumatol Rep 2, 216-224.
60. Libby P, Ridker PM & Maseri A (2002) Inflammation and atherosclerosis. Circulation 105, 1135-1143. (Pubitemid 34212626)
61. Xavier RJ & Podolsky DK (2007) Unravelling the pathogenesis of inflammatory bowel disease. Nature 448, 427-434. (Pubitemid 47123518)
62. Ross JS, Stagliano NE, Donovan MJ et al. (2001) Atherosclerosis and cancer: common molecular pathways of disease development and progression. Ann NY Acad Sci 947, 271-292.
63. Bosca L, Zeini M, Traves PG et al. (2005) Nitric oxide and cell viability in inflammatory cells: a role for NO in macrophage function and fate. Toxicology 208, 249-258. (Pubitemid 40187335)
64. Kaplanski G, Marin V, Montero-Julian F et al. (2003) IL-6: a regulator of the transition from neutrophil to monocyte recruitment during inflammation. Trends Immunol 24, 25-29. (Pubitemid 35462110)
65. Labinskyy N, Csiszar A, Veress G et al. (2006) Vascular dysfunction in aging: potential effects of resveratrol, an antiinflammatory phytoestrogen. Curr Med Chem 13, 989-996.
66. Park MJ, Lee EK, Heo HS et al. (2009) The antiinflammatory effect of kaempferol in aged kidney tissues: the involvement of nuclear factor-kB via nuclear factor-inducing kinase/IkB kinase and mitogen-activated protein kinase pathways. J Med Food 12, 351-358.
67. Fan GW, Gao XM, Wang H et al. (2009) The antiinflammatory activities of Tanshinone IIA, an active component of TCM, are mediated by estrogen receptor activation and inhibition of iNOS. J Steroid Biochem Mol Biol 113, 275-280.
68. Kim HJ, Sung MK & Kim JS (2011) Anti-inflammatory effects of glyceollins derived from soybean by elicitation with Aspergillus sojae. Inflamm Res 60, 909-917.
69. Kanwar JR, Kanwar RK, Burrow H et al. (2009) Recent advances on the roles of NO in cancer and chronic inflammatory disorders. Curr Med Chem 16, 2373-2394.
70. Lee SH, Soyoola E, Chanmugam P et al. (1992) Selective expression of mitogen-inducible cyclooxygenase in macrophages stimulated with lipopolysaccharide. J Biol Chem 267, 25934-25938. (Pubitemid 23013998)
71. Verma IM, Stevenson JK, Schwarz EM et al. (1995) Rel/NFkB/IkB family: intimate tales of association and dissociation. Genes Dev 9, 2723-2735. (Pubitemid 3009952)
72. Baeuerle PA & Baltimore D (1996) NF-kB: ten years after. Cell 87, 13-20.
73. Reddy DB & Reddanna P (2009) Chebulagic acid (CA) attenuates LPS-induced inflammation by suppressing NF-kB and MAPK activation in RAW 264.7 macrophages. Biochem Biophys Res Commun 381, 112-117.
74. Hamalainen M, Nieminen R, Vuorela P et al. (2007) Antiinflammatory effects of flavonoids: genistein, kaempferol, quercetin, and daidzein inhibit STAT-1 and NF-kB activations, whereas flavone, isorhamnetin, naringenin, and pelargonidin inhibit only NF-kB activation along with their inhibitory effect on iNOS expression and NO production in activated macrophages. Mediators Inflamm 2007, article ID 45673.
75. Setchell KD, Borriello SP, Hulme P et al. (1984) Nonsteroidal estrogens of dietary origin: possible roles in hormone-dependent disease. Am J Clin Nutr 40, 569-578. (Pubitemid 14035518)
76. Kim J & Kwon C (2001) Estimated dietary isoflavone intake of Korean population based on National Nutrition Survey. Nutr Res 21, 947-953. (Pubitemid 32641706)
77. Chan SG, Ho SC, Kreiger N et al. (2007) Dietary sources and determinants of soy isoflavone intake among midlife Chinese Women in Hong Kong. J Nutr 137, 2451-2455. (Pubitemid 350058715)
78. Yamamoto S, Sobue T, Sasaki S et al. (2001) Validity and reproducibility of a self-administered food-frequency questionnaire to assess isoflavone intake in a Japanese population in comparison with dietary records and blood and urine isoflavones. J Nutr 131, 2741-2747. (Pubitemid 32947803)
79. Messina M (1999) Soy, soy phytoestrogens (isoflavones), and breast cancer. Am J Clin Nutr 70, 574-575. (Pubitemid 29463454)
80. Wu AH, Ziegler RG, Nomura AM et al. (1998) Soy intake and risk of breast cancer in Asians and Asian Americans. Am J Clin Nutr 68, 1437S-1443S. (Pubitemid 28550926)
81. Kim HJ, Cha BY, Choi B et al. (2011) Glyceollins inhibit platelet-derived growth factor-mediated human arterial smooth muscle cell proliferation and migration. Br J Nutr (Epublication ahead of print version)
82. Urabe K, Nakayama J & Hori Y (1998) Mixed epidermal and dermal hypermelanoses. In The Pigmentary System: Physiology and Pathophysiology, pp. 909-911 [JJ Norlund, RE Boissy, VJ Hearing, RA King & JP Ortonne, editors]. New York: Oxford University Press.
83. Cullen MK (1998) Genetic epidermal syndromes: disorders characterized by lentigines. In The Pigmentary System: Physiology and Pathophysiology, pp. 760-766 [JJ Norlund, RE Boissy, VJ Hearing, RA King & JP Ortonne, editors]. New York: Oxford University Press.
84. Schallreuter KU, Kothari S, Chavan B et al. (2008) Regulation of melanogenesis-controversies and new concepts. Exp Dermatol 17, 395-404. (Pubitemid 351513953)
85. Lee YS, Kim HK, Lee KJ et al. (2010) Inhibitory effect of glyceollin isolated from soybean against melanogenesis in B16 melanoma cells. BMB Rep 43, 461-467.
86. Park S, Ahn IS, Kim JH, et al. (2010) Glyceollins, one of the phytoalexins derived from soybeans under fungal stress, enhance insulin sensitivity and exert insulinotropic actions. J Agric Food Chem 58, 1551-1557.
87. Surh YJ (2003) Cancer prevention with dietary phytochemicals. Nat Rev Cancer 3, 768-780.