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Ipriflavone: an Important Bone-Building Isoflavone

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Ipriflavone: an Important Bone-Building Isoflavone Ipriflavone: An Important Bone-Building Isoflavone Kathleen A. Head, N.D. Abstract Ipriflavone, an isoflavone synthesized from the soy isoflavone daidzein, holds great promise in the prevention and treatment of osteoporosis and other metabolic bone diseases. It has been widely studied in humans and found effective for inhibiting bone resorption and enhancing bone formation, the net result being an increase in bone density and a decrease in fracture rates in osteoporotic women. While ipriflavone appears to enhance estrogen’s effect, it does not possess intrinsic estrogenic activity, making it an attractive adjunct or alternative to conventional hormone replacement therapy. Preliminary studies have also found ipriflavone effective in preventing bone loss associated with chronic steroid use, immobility, ovariectomy, renal osteodystro- phy, and gonadotrophin hormone-releasing hormone agonists. In addition, it holds prom- ise for the treatment of other metabolic diseases affecting the bones, including Paget’s disease of the bone, hyperparathyroidism, and tinnitus caused by otosclerosis. (Altern Med Rev 1999;4(1):10-22) Introduction Ipriflavone (chemical structure: 7-isopropoxyisoflavone), derived from the soy isoflavone, daidzein, holds great promise for osteoporosis prevention and treatment (see Figure 1). Ipriflavone (IP) was discovered in the 1930s but has only recently begun to be embraced by the medical community in this country. Over 150 studies on safety and effective- ness, both animal and human, have been conducted in Italy, Hungary, and Japan. As of 1997, 2,769 patients had been treated a total of 3,132 patient years.1 Pharmacokinetics IP is metabolized mainly in the liver and excreted in the urine. Food appears to enhance its absorption. When given to healthy male volunteers, 80 percent of a 200 mg dose of IP was absorbed when taken after breakfast.2 IP appears to be extensively metabolized. In dogs and rats, seven metabolites were identified in the plasma, labeled MI-MVII. In humans, however, only MI, MII (daidzein), MIII, and MV seem to predominate. The mean excretion half-life in healthy human volunteers was 9.8 hours for ipriflavone and ranged from 2.7-16.1 hours for its metabolites. Ipriflavone metabolism was not found to be significantly different in elderly osteoporotic or mild kidney failure patients than in younger, healthy subjects.3 Studies using Kathi Head, N.D.—Technical Advisor, Thorne Research, Inc.; Senior Editor, Alternative Medicine Review. Correspondence address: P.O. Box 25, Dover, ID 83825, e-mail: [email protected] Page 10 Alternative Medicine Review ◆ Volume 4, Number 1 ◆ 1999 Copyright©1999 Thorne Research, Inc. All Rights Reserved. No Reprint Without Written Permission Ipriflavone Figure 1. Chemical structure of Ipriflavone and Daidzein. labeled IP in rats found growth factor demon- it concentrated primarily Ipriflavone O strate mainly bone form- in the gastrointestinal ing activity.4-5 While IP is tract, liver, kidneys, considered to be prima- CH3 bones, and adrenal rily an anti-resorptive, it 3 glands. H3C OO also possesses bone forming properties. Review Of Bone Anti-resorptive mecha- Remodeling HO nisms: An animal study Daidzein found IP inhibited par- Bone is subject O athyroid hormone-, vita- to continual remodeling; min D-, PGE2- and i.e., the bone is renewed interleukin 1ß-stimulated through a process of re- bone resorption.6 sorption of old bone by HO O Bonnuci et al found osteoclasts and forma- parathyroid-stimulated tion of new bone by osteoclastic activity and resulting hypercalce- osteoblasts. Osteoclastic activity is stimulated mia were inhibited in a dose-dependent man- by parathyroid hormone when serum calcium ner by IP supplementation in rats.7 levels are low. Conversely, calcitonin is se- Ipriflavone metabolites have also been creted from the thyroid in response to hyper- found to inhibit bone resorption. An in vitro calcemia, and antagonizes the bone-resorptive study on fetal rat long bones found all metabo- effects of parathyroid hormone. This process lites capable of inhibiting parathyroid-stimu- occurs in discrete sections called basic multi- lated bone resorption.8 MIII was the strongest cellular units (BMUs). This interaction be- inhibitor, approximately three times more po- tween osteoclasts and osteoblasts is a coupled tent than MII; MI and MV were the least po- process. tent. Azria et al observed no inhibition of Mechanisms of Action bone resorption of incubated bone slices or Ipriflavone appears to have several changes in rat osteoclast motility at IP con- mechanisms of action, all of which enhance centrations greater than 100 times peak blood bone density, making IP seemingly superior concentrations after a standard therapeutic to many of the other treatments available for dose.9 osteoporosis prevention and treatment. While On the contrary, Notoya et al found it has been popular to label osteoporosis drugs ipriflavone to inhibit bone resorption by mouse as primarily either anti-resorptive or bone- osteoclasts. The mechanisms involved forming, this does not take into account the included inhibition of both the activation of fact these two processes are coupled. Because mature osteoclasts and the formation of new of this coupling, substances which have a ben- osteoclasts.10 When IP was combined with eficial effect on prevention of bone resorption vitamin K in cell media, an additive inhibition by osteoclasts may also prevent osteoblastic of bone resorption was noted. In this respect, activity when taken long-term. Treatments vitamin K and ipriflavone appear to have which are primarily anti-resorptive include similar mechanisms of action. However, estrogen, calcium, bisphosphonates, and cal- ipriflavone, but not vitamin K, was found to citonin, while sodium fluoride, anabolic frag- stimulate alkaline phosphatase activity, an ments of parathyroid hormone, and insulin-like Alternative Medicine Review ◆ Volume 4, Number 1 ◆ 1999 Page 11 Copyright©1999 Thorne Research, Inc. All Rights Reserved. No Reprint Without Written Permission indicator of new bone formation. The authors Further evidence of ipriflavone’s direct concluded the inhibitory effects of IP on bone action on osteoblastic activity was provided resorption are similar to those of vitamin K, by Sortino et al, who found IP to affect intrac- while mechanisms for osteoblastic activity are ellular messenger systems in UMR-106a cells different.11 by inhibiting both calcium influx into osteo- Other in vitro studies of isolated os- blasts and phosphoinositide hydrolysis. Both teoclasts using bone resorption assays and calcitonin and estrogen act to preserve bone measurements of intraosteoclastic calcium in a similar manner.16 found ipriflavone inhibited osteoclastic activ- Bonucci et al found in vitro IP appli- ity (motility and resorptive activity) by modu- cations stimulated osteoblast-like cell prolif- lating intracellular free calcium. These results eration and inhibited both parathyroid-induced were achieved at concentrations mimicking the bone degeneration and preosteoclastic cell pro- plasma concentrations reached from typical liferation. The researchers concluded the in- oral IP dosages in vivo.12 Other researchers hibition of resorption may be an indirect ef- confirmed the effect of ipriflavone on calcium fect, mediated by osteoblasts.17 influx in chicken, rat, and rabbit osteoclasts Effect on Advanced Glycation End and preosteoclasts.13 The effect of calcium in- Products (AGE): AGE (proteins nonenzymati- flux into osteoclasts has not been clearly elu- cally reacted with sugar) have been implicated cidated. Miyauchi et al found IP increased in- in a number of chronic degenerative conditions tracellular calcium in osteoclasts and pre-os- especially related to diabetes and aging. AGE teoclasts, and that osteoclast maturation was have also been implicated in bone resorption inhibited. These findings suggest the high cal- around amyloid deposits in dialysis-related cium concentration in precursor cells inhibit amyloidosis. Both ipriflavone and calcitonin osteoclastic maturation. were found, in vitro, to inhibit this AGE-asso- Bone-forming mechanisms: An in vitro ciated bone resorption.18 This may have im- examination of the osteoblastic effect of IP and plications for age- and diabetes-related os- its metabolites resulted in some interesting teoporosis as well. findings. Ipriflavone and metabolite II stimu- Lack of Estrogen Effect: One of the lated cell proliferation of an osteoblast-like cell benefits of ipriflavone in the treatment of os- line (UMR-106a – a cell line often used to de- teoporosis is its lack of estrogenic effect. Melis termine the effect of various hormones and et al administered ipriflavone or placebo to a drugs on bone metabolism). IP and metabo- group of 15 postmenopausal women. lite I increased alkaline phosphatase activity, Leutinizing hormone, follicle-stimulating hor- metabolite V enhanced collagen formation, mone, prolactin, and estradiol were measured and IP alone inhibited parathyroid hormone after a single oral dose of 600 or 1000 mg, activity.14 and after 7, 14, and 21 days of treatment with Bone marrow osteoprogenitor cells 600 or 1000 mg doses. No differences in en- and trabecular bone osteoblasts were isolated docrine effect were noted between the from human donors and incubated with IP and ipriflavone and placebo groups. To examine its metabolites. These substances were found the neuroendocrine effect, the women received to regulate osteoblastic differentiation by en- a naloxone
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