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Isoflavones and Soy Constituents

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Isoflavones and Soy Constituents Isoflavones And Other Soy Constituents In Human Health And Disease Kathleen A. Head, N.D. Abstract In the past several years, soy and its constituents have garnered considerable attention, from both researchers and health practitioners. Epidemiological data which indicated people from Asian cultures have lower rates of certain cancers, including cancer of the breast, prostate and colon, sparked an interest in soy as a contributing factor. While soy constituents, including saponins, lignans, phytosterols, protease inhibitors, and phytates, have come under investigation, the constituents which seem to hold the most promise from a therapeutic standpoint are the two isoflavones, genistein and daidzein. Numerous epidemiological, human, animal, and in vitro studies have demonstrated that soy isoflavones are effective chemopreventive agents for certain types of cancer. Mechanisms involved include antiangiogenesis, estrogen receptor binding, modulation of sex hormone binding globulin (SHBG), anti-inflammatory and antioxidant effects, and inhibition of the enzymes protein tyrosine kinase (PTK) and 5 alpha-reductase. Interaction with many other enzymes has been suggested. Evidence also points to the beneficial effects of soy, particularly the isoflavones, in prevention of cardiovascular disease. Isoflavones appear to inhibit platelet activating factor and thrombin formation. They also increase HDL cholesterol and decrease triglycerides, LDL, VLDL, and total cholesterol. Other potential health benefits of soy include prevention of osteoporosis, via the phytoestrogen effects of isoflavones, and prevention of neovascularization in ocular conditions, via inhibition of angiogenesis. (Alt Med Rev 1997;2(6):433-450) Introduction Recent interest in the constituents of soybeans, particularly the isoflavones, has catapulted soy to the status of a promising nutraceutical with potentially significant health benefits. The principle isoflavones in soy are genistein (4',5,7-trihydroxyisoflavone), daidzein (4',7- dihydroxyisoflavone) (see Figure 1), and their metabolites. In addition, soy products are a source of lignans, coumestans, saponins, plant sterols, phytates (inositol hexaphosphate), and protease inhibitors, all of which are also garnering attention for their health-promoting benefits.1 Soy constituents have been shown to have estrogenic, anti-estrogenic, antiviral,2 anticarcino- genic,3-5 bacteriocidal, and antifungal6 effects. Isoflavones also have antimutagenic,4 antioxidant,7,8 mild anti-inflammatory,9 antihypertensive,9 and antiproliferative effects.3,10 This article will focus Kathi Head, N.D.—Technical Advisor, Thorne Research, Inc.; Associate Editor, Alternative Medicine Review. Correspondence address: P.O. Box 3200, Sandpoint, ID 83864, e-mail: [email protected] Alternative Medicine Review N Volume 3, Number 1 N 1998 Page 433 Copyright©2001Copyright©2001 ThorneThorne Research,Research, Inc.Inc. AllAll RightsRights Reserved.Reserved. NoNo ReprintReprint WithoutWithout WrittenWritten PermissionPermission Figure 1. Structure of Genistein and Daidzein Genistein the fact that the 5 hydroxy group on the HO O genistein binds to the 4 ketonic oxygen, genistein is a more hydrophobic molecule than daidzein. This affords genistein some of its unique therapeutic effects. OH O OH Daidzein Absorption, Metabolism and Excre- O tion of Soy Isoflavones HO Isoflavones undergo extensive metabo- lism in the intestinal tract prior to absorption. Genistein is formed from biochanin A, and daidzein from formononetin.1 Genistein and O OH daidzein also occur in soy products in the form of their glycosides, genistin and daidzin. In the case of the glycosides, intestinal bacterial glu- cosidases cleave the sugar moieties, releasing primarily on isoflavones as these are the the biologically active isoflavones, genistein constituents found in greatest quantity in soy and daidzein. In adults, these are futher trans- products. Brief reference will be made to other formed by bacteria to specific metabolites: beneficial constituents. equol, O-desmethylangolensis, dihydro- genistein, and p-ethylphenol. Due to soy in- Classification of Isoflavones take by livestock, isoflavone metabolites are Flavonoids are a subgroup of the larger also consumed directly in a diet high in dairy group of plant constituents, the polypenols. products and meat.12 In at least one study, Flavonoids are further differentiated into genistein was well-absorbed in the small in- isoflavonoids, with isoflavones a subcategory testines by human subjects fed a soy bever- of isoflavonoids. See Figure 2. Isoflavonoids age.13 After absorption, the isoflavones are differ from other classes of flavonoids by their transported to the liver where they are removed greater structural variability, their frequent from the portal blood. However, a percentage presence in plants in their free form, rather than of the isoflavones in the portal blood can es- as a glycoside, and by the greater frequency cape uptake by the liver and enter the periph- of isoprenoid substitution. They are not as eral circulation. The effectiveness of this he- ubiquitous in nature as some of the other fla- patic first-pass clearance influences the vonoids such as flavones and flavonols, being amount which reaches peripheral tissues.13 The found primarily in one subfamily of isoflavones are then eliminated, primarily via Leguminosae, the Papilionoideae.11 Approxi- the kidneys, similar to endogenous estrogens.14 mately 600 isoflavonoids have been identified. After examining plasma, fecal and They are divided into subclasses depending urinary concentrations of isoflavones in on the oxidation level of the central pyran ring. healthy volunteers, Xu et al concluded the Isoflavones are the most abundant of the sub- bioavailability of soy isoflavones is influenced classes of isoflavonoids. Genistein and by an intact, healthy gut, with microflora daidzein are two important isoflavones. As can capable of converting these isoflavones to their be seen in Figure 1, genistein has a hydroxy active forms.15 Wheat fiber appears to decrease group in the 5 position, giving it three hydroxy the bioavailability of genistein. A small cross- groups, while daidzein has just two. Due to over study of seven healthy women found a Page 434 Alternative Medicine Review N Volume 3, Number 1 N 1998 Copyright©2001 Thorne Research, Inc. All Rights Reserved. No Reprint Without Written Permission Soy Isoflavones Figure 2. Polyphenol classification Polyphenols Tannins Stilbenes Hydroxycinnamic Acid Aaphthoquinones Lignans Xanthones Flavonoids Hydroxybenzoic Acid Hydrolysable Condensed enterolactone enterodiol (proanthocyanidin) Flavones Flavanones Flavanolols Chalcones Anthocyanidins Flavans Neoflavonoids Flavonols Catechin Aurons Isoflavonoid Isoflavanones Isoflavans Isoflavones Pterocarpans Rotenoids Daidzein Genistein Other non-soy (from formononetin) (from biochanin A) isoflavones (eg. irilone, luteone, prunetin, pratensein, etc.) metabolized to Equol O-desmethylangolensis Dihydrogenestein P-ethylphenol There are thousands of polyphenolic compounds and over 600 isoflavonoids. This is by no means a complete list but is intended to offer some perspective. more fiber-rich diet resulted in 55 percent less increases bioavailability of the isoflavones. plasma genistein 24 hours after soy intake and Plasma levels of soy isoflavones were also a 20 percent reduction in total urinary increased after consumption of soy flour and genistein. The researchers postulated the fairly clover sprouts.19 insoluble wheat fiber reduced the absorption of genistein by its bulking effect and Isoflavone Content of Soy Products 16 hydrophobic binding. Karr et al found urinary Fukutake et al analyzed soy products excretion of isoflavones to be reflective of the for genistein and genistin (the glycoside of 17 type and amount of soy ingested. A study genistein) content. The results are outlined in conducted on healthy male subjects between Table 1. In general, they found fermented soy the ages of 20 and 40 found urinary excretion products contain more genistein than soy- of genistein and daidzein was greater after beans, soy milk and tofu.20 Alcohol extraction, consumption of 112 grams of tempeh, a a process used in the production of many soy fermented soy product, than after 125 grams protein concentrates and isolates (used in soy 18 of unfermented soy pieces. This finding protein powders), results in the removal seems to indicate fermentation of soy products of up to 90 percent of the isoflavones.21 Alternative Medicine Review N Volume 3, Number 1 N 1998 Page 435 Copyright©2001 Thorne Research, Inc. All Rights Reserved. No Reprint Without Written Permission Table 1. Levels of Genistein and its glycoside, Genistin in soy foods (analyzed by high performance liquid chromatography)20 Genistein Genistin Soybeans, Soy nuts 4.6 - 18.2 mcg/g* 200.6 - 968.1 mcg/g and Soy powder Soy milk and Tofu 1.9 - 13.9 mcg/g 94.8 - 137.7 mcg/g Fermented Soy** 38.5 - 229.1 mcg/g 71.7 - 492.8 mcg/g Miso and Natto Calcuted daily dietary 1.5 - 4.1 mg/day/person 6.3 - 8.3 mg/day/person intake by the Japanese * mcg/gram of food ** soy sauce was found to contain both isoflavones but at lower levels than miso or natto (fermented soy beans) The isoflavone content of soybeans varies con- by a non-specific effect on metabolism.28,29 siderably depending on the variety of soybean Some researchers have theorized the dietary (there are over 10,000 varieties of soybeans), intake of exogenous PIs indirectly increases the year harvested,
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