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Also known as: 446-72-0, Prunetol, 4',5,7-trihydroxyisoflavone, Genisterin, Genisteol, Sophoricol
Molecular Formula
C15H10O5
Molecular Weight
270.24  g/mol
InChI Key
TZBJGXHYKVUXJN-UHFFFAOYSA-N
FDA UNII
DH2M523P0H

Genistein
An isoflavonoid derived from soy products. It inhibits PROTEIN-TYROSINE KINASE and topoisomerase-II (DNA TOPOISOMERASES, TYPE II); activity and is used as an antineoplastic and antitumor agent. Experimentally, it has been shown to induce G2 PHASE arrest in human and murine cell lines and inhibits PROTEIN-TYROSINE KINASE.
1 2D Structure

Genistein

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one
2.1.2 InChI
InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H
2.1.3 InChI Key
TZBJGXHYKVUXJN-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O
2.2 Other Identifiers
2.2.1 UNII
DH2M523P0H
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Genestein

2.3.2 Depositor-Supplied Synonyms

1. 446-72-0

2. Prunetol

3. 4',5,7-trihydroxyisoflavone

4. Genisterin

5. Genisteol

6. Sophoricol

7. 5,7-dihydroxy-3-(4-hydroxyphenyl)-4h-chromen-4-one

8. 5,7,4'-trihydroxyisoflavone

9. Bonistein

10. Differenol A

11. 5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one

12. Npi 031l

13. 5,7-dihydroxy-3-(4-hydroxyphenyl)-4h-1-benzopyran-4-one

14. 4h-1-benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)-

15. C.i. 75610

16. Sipi 807-1

17. Mfcd00016952

18. 5,7-dihydroxy-3-(4-hydroxyphenyl)-4-benzopyrone

19. Nsc 36586

20. Genistein [usan]

21. Nsc36586

22. Chembl44

23. Nsc-36586

24. Bio 300

25. Isoflavone, 4',5,7-trihydroxy-

26. Mls000738127

27. Dh2m523p0h

28. Npi-031l

29. Genestein

30. Chebi:28088

31. Bio-300

32. Sipi-807-1

33. Genistein (usan)

34. Fw-635i-2

35. Gen

36. Ncgc00015479-09

37. Dsstox_cid_2308

38. Dsstox_rid_76542

39. Dsstox_gsid_22308

40. Cas-446-72-0

41. Lactoferrin-genistein

42. Ccris 7675

43. 4',5, 7-trihydroxyisoflavone

44. Sr-01000075498

45. Einecs 207-174-9

46. Brn 0263823

47. Unii-dh2m523p0h

48. Sto514

49. Hsdb 7475

50. Pti G4660

51. Pti-g4660

52. Sipi-9764-i

53. 3kgt

54. 3kgu

55. Genistein, 8

56. Genistein,(s)

57. Pti-g 4660

58. Tnp00151

59. Genistein (flavonoid)

60. Spectrum_000320

61. Tocris-1110

62. 1x7r

63. 2qa8

64. Genistein 85% Hplc

65. Genistein [inn]

66. Specplus_000305

67. Genistein [mi]

68. Genistein [hsdb]

69. Genistein [inci]

70. Spectrum2_000638

71. Spectrum3_000678

72. Spectrum4_001543

73. Spectrum5_000106

74. Lopac-g-6649

75. 4',7-trihydroxyisoflavone

76. Genistein [mart.]

77. Molmap_000022

78. Upcmld-dp096

79. G 6649

80. Genistein [usp-rs]

81. Genistein [who-dd]

82. 4,5,7-trihydroxyisoflavone

83. Isoflavone,5,7-trihydroxy-

84. Lopac0_000520

85. Oprea1_224620

86. Oprea1_437815

87. Schembl19166

88. Bspbio_002375

89. Kbiogr_002006

90. Kbiogr_002564

91. Kbioss_000800

92. Kbioss_002573

93. Npi031l

94. Spectrum210296

95. 5-18-04-00594 (beilstein Handbook Reference)

96. Bidd:er0113

97. Divk1c_006401

98. Genistein, Analytical Standard

99. Spbio_000636

100. 4',5,7-trihydroxy-isoflavone

101. Gtpl2826

102. Megxp0_000568

103. 4,5,7-trihydroxy Iso-flavone

104. Dtxsid5022308

105. Upcmld-dp096:001

106. Acon1_001065

107. Bdbm19459

108. Cid_5280961

109. Kbio1_001345

110. Kbio2_000800

111. Kbio2_002564

112. Kbio2_003368

113. Kbio2_005132

114. Kbio2_005936

115. Kbio2_007700

116. Kbio3_001595

117. Kbio3_003042

118. Chebi: 28088

119. Cmap_000086

120. Bio1_000445

121. Bio1_000934

122. Bio1_001423

123. Hms2271k09

124. Hms3261h21

125. Hms3267k14

126. Hms3412i13

127. Hms3428m01

128. Hms3649b22

129. Hms3654d17

130. Hms3676i13

131. Hms3742i07

132. Act05962

133. Albb-015886

134. Amy25676

135. Bcp07581

136. Tox21_110161

137. Tox21_201428

138. Tox21_300585

139. Tox21_500520

140. Ac-472

141. Bbl010484

142. Ccg-38551

143. Lmpk12050218

144. S1342

145. Stk801619

146. Who 11073

147. Zinc18825330

148. Akos001590147

149. Tox21_110161_1

150. Cs-1534

151. Db01645

152. Ks-5128

153. Lp00520

154. Sb17235

155. Sdccgsbi-0050503.p003

156. Smp1_000133

157. Genistein; 4',5,7-trihydroxyisoflavone

158. Ncgc00015479-01

159. Ncgc00015479-02

160. Ncgc00015479-04

161. Ncgc00015479-05

162. Ncgc00015479-06

163. Ncgc00015479-07

164. Ncgc00015479-08

165. Ncgc00015479-10

166. Ncgc00015479-11

167. Ncgc00015479-12

168. Ncgc00015479-13

169. Ncgc00015479-14

170. Ncgc00015479-15

171. Ncgc00015479-16

172. Ncgc00015479-17

173. Ncgc00015479-18

174. Ncgc00015479-19

175. Ncgc00015479-20

176. Ncgc00015479-38

177. Ncgc00025005-01

178. Ncgc00025005-02

179. Ncgc00025005-03

180. Ncgc00025005-04

181. Ncgc00025005-05

182. Ncgc00025005-06

183. Ncgc00025005-07

184. Ncgc00169711-01

185. Ncgc00169711-02

186. Ncgc00254275-01

187. Ncgc00258979-01

188. Ncgc00261205-01

189. 690224-00-1

190. Hy-14596

191. Nci60_003369

192. Smr000112580

193. Sy050124

194. Eu-0100520

195. Ft-0603395

196. Ft-0668961

197. Ft-0668962

198. G0272

199. N1861

200. Sw203763-2

201. 46g720

202. C06563

203. D11680

204. G-2535

205. Genistein, Synthetic, >=98% (hplc), Powder

206. K00046

207. Us8552057, 2

208. Ab00052696_09

209. Ab00052696_12

210. 5,7-dihydroxy-3-(4-hydroxyphenyl)-chromen-4-one

211. A826657

212. Q415957

213. Genistein (constituent Of Red Clover) [dsc]

214. Genistein, Primary Pharmaceutical Reference Standard

215. Q-100484

216. Sr-01000075498-1

217. Sr-01000075498-3

218. Sr-01000075498-6

219. 3-(4-hydroxyphenyl)-5,7-bis(oxidanyl)chromen-4-one

220. Brd-k43797669-001-02-3

221. Brd-k43797669-001-03-1

222. Brd-k43797669-001-10-6

223. Genistein, From Glycine Max (soybean), ~98% (hplc)

224. Sr-01000075498-10

225. 5,7-dihydroxy-3-(4-hydroxyphenyl)-1-benzopyran-4-one

226. F0001-2388

227. Genistein (constituent Of Soy Isoflavones) [dsc]

228. 4h-1-benzopyran-4-one,7-dihydroxy-3-(4-hydroxyphenyl)-

229. Genistein, United States Pharmacopeia (usp) Reference Standard

230. Genistein, Pharmaceutical Secondary Standard; Certified Reference Material

231. 5,7-dihydroxy-3-(4-hydroxyphenyl)-4h-1-benzopyran-4-one; 4',5,7-trihydroxyisoflavone; Prunetol; Genisteol

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 270.24 g/mol
Molecular Formula C15H10O5
XLogP32.7
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count1
Exact Mass270.05282342 g/mol
Monoisotopic Mass270.05282342 g/mol
Topological Polar Surface Area87 Ų
Heavy Atom Count20
Formal Charge0
Complexity411
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

/EXPTL/ Genistein is speculated to provide beneficial effects on cardiovascular and bone health and to alleviate menopausal symptoms; studies examining such endpoints have been limited in number, provided inconsistent findings, or evaluated soy product consumption instead of exposure to genistein alone.

National Toxicology Program, Center For the Evaluation of Risks To Human Reproduction; NTP-CERHR Expert Panel Report on the Reproductive and Developmental Toxicity of Genistein; (NTP-CERHR-GENISTEIN-06) April 2006. Available from, as of August 14, 2007: https://cerhr.niehs.nih.gov/chemicals/genistein-soy/genistein/Genistein_Report_final.pdf


/EXPTL/ Interest in ... /genistein/ is concentrated in particular on its therapeutic role in menopause. This paper is a review of the main studies published to date on the efficacy of phytoestrogens in reducing the symptoms of menopause. A diet rich in isoflavones is associated with a reduced incidence of vasomotor episodes; the average supplement of genistein is approximately 50 mg/day. After supplementing the diet with phytoestrogens, studies show a reduction in total cholesterol and LDL fraction. This is accompanied by an increase in BMD (Bone mineral density) after taking 90 mg of isoflavones for 6 months. Isoflavones may reduce the risk of developing breast cancer. The data examined confirm the excellent clinical efficacy of supplementing the diet with soy extracts, particularly genistein which is indicated to alleviate both the short-term symptoms of menopause and the long-term effects, although the latter finding requires further subsantiation.

PMID:11828270 Arena S et al; Minerva Ginecol 54 (1): 53-7 (2002)


/EXPTL/ ... /The authors/ evaluated and compared the effects of the phytoestrogen genistein, estrogen-progestogen therapy (EPT), and placebo on hot flushes and endometrial thickness in postmenopausal women. ... Ninety healthy, postmenopausal women, 47 to 57 years of age, were randomly assigned to receive for 1 year continuous EPT (n = 30; 1 mg 17beta-estradiol combined with 0.5 mg norethisterone acetate), the phytoestrogen genistein (n = 30; 54 mg/day), or placebo (n = 30). Endometrial safety was evaluated by intravaginal ultrasounds at baseline, 6 and 12 months. ... By comparison with placebo, daily flushes reduced significantly by a mean of 22% (95% CI: -38 to -6.2; P < 0.01) after 3 months, by a mean of 29% (95% CI: -45 to -13; P < 0.001) after 6 months, and by a mean of 24% (95% CI: -43 to -5; P < 0.01) after 12 months of genistein treatment. Flush score decreased by a mean of 53% (95% CI: -79 to -26; P < 0.001) after 3 months, by a mean of 56% (95% CI: -83 to -28; P < 0.001) after 6 months, and by a mean of 54% (95% CI: -74 to -33; P < 0.001) after 12 months of EPT, as compared with placebo. No side effect was observed on the uterus of the participants. ... The present study confirms that genistein might have positive effects on hot flushes without a negative impact on endometrial thickness and suggests a future role of this phytoestrogen as a strategically therapeutic alternative in the management of postmenopausal symptoms.

PMID:15243277 Crisafulli A et al; Menopause 11 (4): 400-4 (2004)


/EXPTL/ There is a growing body of in vitro and animal studies suggesting that genistein may be helpful in preventing and treating some cancers, principally breast and prostate cancers. The clinical studies that might support or refute claims that genistein has anti-atherogenic properties and that it can safely and effectively be used as natural estrogen-replacement therapy have not been conducted. There are, however, preliminary data suggesting that soy isoflavones, including genistein, may be helpful in some problems associated with menopause, including osteoporosis and hot flashes.

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ p.180 (2001)


For more Therapeutic Uses (Complete) data for GENISTEIN (6 total), please visit the HSDB record page.


4.2 Drug Warning

Genistein/genistin intake has been associated with hypothyroidism in some.

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ p.180 (2001)


Women with estrogen receptor-positive tumors should exercise caution in the use of genistein/genistin supplements and should only use them if they are recommended and monitored by a physician.

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ p.180 (2001)


Men with prostate cancer should discuss the advisability of the use of genistein/genistin supplements with their physicians before deciding to use them.

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ p.180 (2001)


Pregnant women and nursing mothers should avoid the use of genistein/genistin supplements pending long-term safety studies.

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ p.180 (2001)


Caution is warranted for postmenopausal women consuming dietary genistein while on tamoxifen therapy for estrogen-responsive breast cancer.

PMID:11980635 Ju YH et al; Cancer Res 62(9):2474-7 (2002)


4.3 Drug Indication

Currently Genistein is being studied in clinical trials as a treatment for prostate cancer.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Phytoestrogens

Compounds derived from plants, primarily ISOFLAVONES that mimic or modulate endogenous estrogens, usually by binding to ESTROGEN RECEPTORS. (See all compounds classified as Phytoestrogens.)


Protein Kinase Inhibitors

Agents that inhibit PROTEIN KINASES. (See all compounds classified as Protein Kinase Inhibitors.)


Anticarcinogenic Agents

Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved. (See all compounds classified as Anticarcinogenic Agents.)


5.2 Absorption, Distribution and Excretion

... Genistein is rapidly absorbed in humans following oral intake. Before absorption into the systemic circulation, most genistein is conjugated with glucuronic acid and excreted in the bile to undergo enterohepatic circulation ... . Therefore, genistein bioavailability is very limited. Times to obtain maximum plasma concentrations were reported at 1 to 6 hours for free genistein ... and 3 to 8 hours for total genistein (aglycone + conjugates ...). In one of the studies, the lowest dose used (2 mg/kg bw) was stated to provide more than twice the level of isoflavones ingested in a Japanese daily diet. A study in which menopausal women were given a 50 mg commercial isoflavone extract incorporated into fruit juice, chocolate, or a cookie showed no significant effect of the food matrix on genistein absorption or urinary excretion parameters. In a study in which 8 women were dosed with 0.4 or 0.8 mg/kg bw 13C-labeled genistein, the area under the curve (AUC) at the higher dose was less than double the AUC at the lower dose, suggesting a decrease in fractional absorption with increasing dose.

National Toxicology Program, Center For the Evaluation of Risks To Human Reproduction; NTP-CERHR Expert Panel Report on the Reproductive and Developmental Toxicity of Genistein; (NTP-CERHR-GENISTEIN-06) April 2006. Available from, as of August 14, 2007: https://cerhr.niehs.nih.gov/chemicals/genistein-soy/genistein/Genistein_Report_final.pdf


There is considerable individual variation in the absorption and metabolism of ingested genistin and genistein. There are some data suggesting that genistein may be more bioavailable than genistin. However, other data suggest that the extent of absorption of genistein is similar for the aglycone and the glucoside forms. There are little data available on the tissue distribution of genistein.

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ p.180 (2001)


A recently completed study has also shown inter-individual variation in the urinary excretion of isoflavones and their metabolites following soy challenge in adults. In this study, 76 volunteers were fed either a high (104+/-24 mg total isoflavones/day) or low (0.5+/-0.5 mg total isoflavones/day) soya diet for 10 weeks. Volunteers on the high soya diet showed extensive urinary excretion of daidzein, genistein and their metabolites. Of the volunteers on the high soya diet 34% were identified as good equol excretors ( 1000 nmol/24 hours). Comparative analysis of the fecal flora between equol and non-equol producers was investigated, however, the microflora (bacteria) responsible for equol production could not be isolated and therefore, were not be identified

Hughs I, Woods HF; Committee on Toxicity of Chemicals in Food, Consumer Products and the Environment Phytoestrogens and Health. UK Food Standards Agency, 444 p. (May 2003). Available from, as of August 14, 2007: https://www.food.gov.uk/multimedia/pdfs/phytoreport0503


The pharmacokinetics of isoflavones in 10 healthy women were determined from serum appearance/disappearance concentration profiles and urinary excretions after single-bolus ingestion of 10, 20 or 40 g of soy nuts delivering increasing amounts of the conjugated forms of daidzein (6.6, 13.2 and 26.4 mg) and genistein (9.8, 19.6 and 39.2 mg). Peak serum daidzein and genistein concentrations were attained after 4-8 hr, and elimination half-lives were 8.0 and 10.1 hr, respectively. There were no differences in the pharmacokinetics of daidzein and genistein between pre- and postmenopausal women, indicating absorption and disposition of isoflavones to be independent of age or menopausal status. A curvilinear relationship was observed between the bioavailability of daidzein and genistein, apparent from the area under the curve to infinity (AUC(inf)) of the serum concentration-time profiles and the amount of isoflavones ingested. The mean fraction of the isoflavones excreted in urine decreased with increasing intake when expressed as a percentage of the administered dose (63.2 + or - 8.0, 54.4 + or - 8.1 and 44.0 + or - 4.3%, respectively, for daidzein, and correspondingly, 25.2 + or - 5.3, 13.4 + or - 2.1 and 15.8 + or - 2.7% for genistein), underscoring the trend toward nonlinear pharmacokinetics. Equol was identified as a metabolite in 30% of women; it was present consistently in urine and blood from the same subjects. Its delayed appearance was consistent with colonic synthesis. On the basis of the pharmacokinetics, optimum steady-state serum isoflavone concentrations would be expected from modest intakes of soy foods consumed regularly throughout the day rather than from a single highly enriched product.

PMID:12672914 Setchell KD et al; J Nutr 133 (4): 1027-35 (2003)


For more Absorption, Distribution and Excretion (Complete) data for GENISTEIN (15 total), please visit the HSDB record page.


5.3 Metabolism/Metabolites

Toxicokinetic and metabolism data in humans and experimental animals indicate that genistein is absorbed into the systemic circulation of infants and adults. Genistein ... circulates as its glucuronide conjugate, and a much smaller percentage circulates as the aglycone. Genistein can be glucuronidated in the intestine or liver, but the intestine appears to play the major role in glucuronidation. Genistein glucuronides undergo enterhepatic cycling, and in the process can be deconjugated by intestinal bacteria. The role of gut bacteria in the metabolism of genistein has been clearly established. Genistein can be metabolized through a pathway that ultimately leads to the formation of 6'-hydroxy-O-demethylangolensin. Once absorbed, genistein glucuronide, and to a smaller extent genistien aglycone, are widely distributed to organ systems and the conceptus. The majority of a genistein dose is excreted in urine within 24 hours.

National Toxicology Program, Center For the Evaluation of Risks To Human Reproduction; NTP-CERHR Expert Panel Report on the Reproductive and Developmental Toxicity of Genistein; (NTP-CERHR-GENISTEIN-06) April 2006. Available from, as of August 14, 2007: https://cerhr.niehs.nih.gov/chemicals/genistein-soy/genistein/Genistein_Report_final.pdf


Prior to entering the systemic circulation, most genistein is conjugated with glucuronic acid by uridine diphosphate (UDP)-glucuronosyltransferase (UDPGT); a much smaller amount is conjugated to sulfate by sulfotransferase enzymes. Conjugation of genistein occurs in the intestine, although it also has been reported to occur in liver. One study demonstrated that the ability to catalyze glucuronidation of genistein was greatest with microsomes from kidney > colon > liver. UDPGT isoenzymes including 1A1, 1A4, 1A6, 1A7, 1A9, and 1A10 were observed to catalyze the glucuronidation of genistein. The UGT 1A10 isoform, which is present in colon, gastric, and biliary epithelium but not in liver, was observed to have the highest activity and specificity for genistein. Based on those observations, the study authors concluded that the intestine plays a major role in the glucuronidation of genistein. The glucuronide and sulfate conjugates can enter the systemic circulation, and the majority of isoflavone compounds in the circulation are present in conjugated form. In studies where humans were exposed to genistein alone or in combination with other isoflavone aglycones (calculated as genistein doses of 1-16 mg/kg bw), most of the genistein was present in plasma in conjugated form; free genistein represented 1-3% of total plasma genistein levels. The conjugated isoflavones undergo enterohepatic circulation, and upon return to the intestine, they are deconjugated by bacteria possessing beta-glucuronidase or arylsulfatase activity. The metabolites may be reabsorbed or further metabolized by gut microflora. One review reported that about 10% of isoflavonoids are circulated in plasma unconjugated.

National Toxicology Program, Center For the Evaluation of Risks To Human Reproduction; NTP-CERHR Expert Panel Report on the Reproductive and Developmental Toxicity of Genistein; (NTP-CERHR-GENISTEIN-06) April 2006. Available from, as of August 14, 2007: https://cerhr.niehs.nih.gov/chemicals/genistein-soy/genistein/Genistein_Report_final.pdf


Biotransformations by gut microflora play a pivotal role in determining the biological activity of isoflavones that occur in soya-based foods predominantly as betaglycosyl conjugates. Microflora prepared from rat caeca and human feces were used to investigate the metabolic fate of genistein beta-glycosides extracted from soya flour. The end-products of such metabolism were determined by parallel incubations of microflora with [2',3,5',6'-3H] and [4-14C]-labelled genistein. ... Quantitative analysis by LC-MS/IS indicated very rapid and complete degradation of genistin, which was associated with a transient increase in genistein. Qualitative studies indicated that the malonyl and acetyl glycosides of genistein were also degraded by the microflora. ... Incubation of caecal and fecal microflora with (3)H and (14)C genistein yielded similar radiolabelled metabolites, which were identified by radio-LC-MS(n) as the intermediates dihydrogenistein and 6'-hydroxy-O-desmethylangolensin and end-product 4-hydroxyphenyl-2-propionic acid. This profile of genistein metabolites indicated selective hydrolysis of 6'-hydroxy-O-desmethylangolensin between carbon atoms 1' and 1 to yield the end-products 4-hydroxyphenyl-2-propionic acid and 1,3,5-trihydroxybenzene. ... The biological significance of the products of genistein metabolism warrant further investigation since they may play an important role in mediating the beneficial antioxidant health effects associated with the consumption of isoflavones in food.

PMID:11820509 Coldham NG et al; Xenobiotica 32 (1): 45-62 (2002)


Biotransformation of the phytoestrogen (14-C)genistein was investigated in male and female rats by application of narrow-bore radio-HPLC-MSn (LCQ, Finnigan) to determine intermediates in metabolism. Urine contained five metabolites, Gm1-Gm5, 24 hr after dosing by gavage with [14C]genistein (4 mg kg(-1)). Structural analysis following ESI revealed molecular ions (M+H)+ of m/z 447, 449, 273, and 271 for metabolites Gm2, Gm3, Gm5 and genistein, respectively and an [M-H]- of m/z 349 for Gm4. Metabolite structure was deduced by evaluation of product ion spectra derived from unlabelled and (14)C-labelled ions and sensitivity to treatment with beta-glucuronidase. These studies indicated identity of metabolites with genistein glucuronide (Gm2), dihydrogenistein glucuronide (Gm3), genistein sulphate (Gm4) and dihydrogenistein (Gm5). Detection of the beta-glucuronidase resistant major metabolite Gm1 by ESI was poor and so was analysed by negative ion APCI; this revealed a deprotonated molecular ion of m/z 165 which had chromatographic and mass spectral properties consistent with authentic 4-hydroxyphenyl-2-propionic acid, a novel metabolite of genistein. In vitro metabolism studies with anaerobic caecal cultures derived from male and female rats revealed metabolism of genistein to Gm1 via Gm5 and an additional metabolite (Gm6) which was identified from product ion spectra as 6'-hydroxy-O-desmethylangolensin. Biotransformation of genistein by both isolated hepatocytes and precision-cut liver slices was limited to glucuronidation of parent compound. Commonality of genistein metabolites found in rats with those reported in man suggest similar pathways of biotransformation, primarily involving gut micro-flora.

PMID:10622405 Coldham NG et al; J Steroid Biochem Mol Biol 70 (4-6): 169-84 (1999)


For more Metabolism/Metabolites (Complete) data for GENISTEIN (7 total), please visit the HSDB record page.


Genistein has known human metabolites that include (2S,3S,4S,5R)-3,4,5-Trihydroxy-6-[5-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxane-2-carboxylic acid, Dihydrogenistein, and Orobol.

Genistein is a known human metabolite of biochanin a.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.4 Biological Half-Life

... Thirty healthy men ingested a single dose of 1 of 2 isoflavone preparations purified from soy. The delivered doses of genistein (1, 2, 4, 8, or 16 mg/kg body wt) were higher than those previously administered to humans. Formulation A was composed of 90 +/- 5% genistein, 10% daidzein, and 1% glycitein. Formulation B was composed of 43% genistein, 21% daidzein, and 2% glycitein. ... The mean elimination half-lives with both formulations were 3.2 hr for free genistein and 4.2 hr for free daidzein. The mean pseudo half-lives were 9.2 hr for total genistein and 8.2 hr for total daidzein.

PMID:11756070 Busby MG et al; Am J Clin Nutr 75 (1): 126-36 (2002)


The pharmacokinetics of isoflavones in 10 healthy women were determined from serum appearance/disappearance concentration profiles and urinary excretions after single-bolus ingestion of 10, 20 or 40 g of soy nuts delivering increasing amounts of the conjugated forms of daidzein (6.6, 13.2 and 26.4 mg) and genistein (9.8, 19.6 and 39.2 mg). Peak serum daidzein and genistein concentrations were attained after 4-8 hr, and elimination half-lives were 8.0 and 10.1 hr, respectively.

PMID:12672914 Setchell KD et al; J Nutr 133 (4): 1027-35 (2003)


Mass balance, plasma pharmacokinetics, tissue distribution, and metabolism of (14-C)genistein were investigated in male and female rats (n = 5) following an oral dose of (14-C)genistein (4 mg/kg) to determine potential sites and mechanisms of biological action. Mean total excretion of radioactivity in urine and feces for both sexes was 66 and 33% of the dose respectively at 166 hr after administration. Mean and maximal concentrations of radioactivity in plasma were significantly (P < 0.02) higher in male than female rats, with half-lives of 12.4 and 8.5 hr, respectively.

PMID:10764634 Coldham NG et al; Toxicol Appl Pharmacol 164 (2): 206-15 (2000)


5.5 Mechanism of Action

Genistein may inhibit cancer cell growth by blocking enzymes required for cell growth. Genistein may decrease cardiovascular risk in postmenopausal women by interacting with the nuclear estrogen receptors to alter the transcription of cell specific genes. In randomized clinical trials, genistein was seen to increase the ratio of nitric oxide to endothelin and improved flow-mediated endothelium dependent vasodilation in healthy postmenopausal women. In addition, genistein may have beneficial effects on glucose metabolism by inhibiting islet tyrosine kinase activity as well as insulin release dependent on glucose and sulfonylurea.


Several mechanisms have been proposed for genistein's putative anticarcinogenic activity. These include upregulation of apoptosis, inhibition of angiogenesis, inhibition of DNA topoisomerase II and inhibition of protein tyrosine kinases. Genistein's weak estrogenic activity has been suggested as another mechanism for genistein's putative anti-prostate cancer activity. In addition to the above mechanisms, other mechanisms of genistein's putative anti-prostate cancer activity include inhibition of nuclear factor (NF)-Kappa B in prostate cancer cells, downregulation of TGF (transforming growth factor)-beta and inhibition of EGF (epidermal growth factor)-stimulated growth. Genistein's anti-estrogenic action may be another possible mechanism to explain its putative anti-breast cancer activity. In the final analysis, the mechanism of genistein's putative anticarcinogenic activity is unclear.

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ p.179 (2001)


A number of studies have shown that genistein can interact with topoisomerase II in vitro. ... Genistein (3.7 M) stabilizes the topoisomerase II-DNA complex. ... stimulating topoisomerase II dependent DNA cleavage (in the ranges 80-370 M and 12.5-250 M, respectively). ... Genistein 50 M) inhibited unwinding of DNA by topoisomerase II in primary hematopoietic cells and stimulated strand breakage. ...The effect of genistein on the DNA cleavage and ATP hydrolysis steps of the topoisomerase II catalysed reactions /was investigated and/ genistein inhibited enzyme-catalysed ATP hydrolysis with an IC50 of 7 M. However, genistein did not stimulate DNA cleavage. Further studies ... showed that genistein (50 M) and daidzein (100 M) induced cleavage of the MLL gene in primary hematopoietic cells. Further in vitro experiments suggested that inhibition of topoisomerase II catalysed re-ligation of DNA strand breaks as the mechanism of action.

Hughs I, Woods HF; Committee on Toxicity of Chemicals in Food, Consumer Products and the Environment Phytoestrogens and Health. UK Food Standards Agency, 444 p. (May 2003). Available from, as of August 14, 2007: https://www.food.gov.uk/multimedia/pdfs/phytoreport0503


Genistein has been found to have a number of antioxidant activities. It is a scavenger of reactive oxygen species and inhibits lipid peroxidation. It also inhibits superoxide anion generation by the enzyme xanthine oxidase. In addition, genistein, in animal experiments, has been found to increase the activities of the antioxidant enzymes superoxide dismutase, glutathione peroxidase, catalase and glutathione reductase.

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ p.179 (2001)


Genistein has weak estrogenic activity as measured in in vivo and in vitro assays. In vivo, its estrogenic activity is one-third that of glycitein and four times greater than that of daidzein.

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ p.179 (2001)


For more Mechanism of Action (Complete) data for GENISTEIN (9 total), please visit the HSDB record page.


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About the Company : Since 2008, Sunriver Biotech has been a leader in the research and utilizing plant resources for people’s well-being and quality of life.Through 12 years development, Sunriver Bi...

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28-Jan-2021
30-Sep-2024
KGS
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