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Quercetin Dihydrate

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Quercetin

Synopsis

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Chemistry

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Also known as: 117-39-5, Meletin, Sophoretin, Quercetine, Xanthaurine, Quercetol

Molecular Formula

C₁₅H₁₀O₇

Molecular Weight

302.23 g/mol

InChI Key

REFJWTPEDVJJIY-UHFFFAOYSA-N

FDA UNII

9IKM0I5T1E

A flavonol widely distributed in plants. It is an antioxidant, like many other phenolic heterocyclic compounds. Glycosylated forms include RUTIN and quercetrin.

1 2D Structure

Quercetin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one

2.1.2 InChI

InChI=1S/C15H10O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,16-19,21H

2.1.3 InChI Key

REFJWTPEDVJJIY-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O)O

2.2 Other Identifiers

2.2.1 UNII

9IKM0I5T1E

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3,3',4',5,7-pentahydroxyflavone

2. Dikvertin

2.3.2 Depositor-Supplied Synonyms

1. 117-39-5

2. Meletin

3. Sophoretin

4. Quercetine

5. Xanthaurine

6. Quercetol

7. Quertine

8. 3,3',4',5,7-pentahydroxyflavone

9. Quercitin

10. 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4h-chromen-4-one

11. Cyanidelonon 1522

12. 3,5,7,3',4'-pentahydroxyflavone

13. Flavin Meletin

14. Quertin

15. T-gelb Bzw. Grun 1

16. C.i. Natural Yellow 10

17. Quercetin Content

18. Kvercetin

19. C.i. 75670

20. 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4h-1-benzopyran-4-one

21. C.i. Natural Red 1

22. 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one

23. Corvitin

24. Cyanidenolon 1522

25. 4h-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-

26. 3',4',5,7-tetrahydroxyflavan-3-ol

27. Flavone, 3,3',4',5,7-pentahydroxy-

28. C.i. Natural Yellow 10 & 13

29. Nsc 9219

30. Lipoflavon

31. Ccris 1639

32. Korvitin

33. Hsdb 3529

34. Nci-c60106

35. 3',4',5,7-tetrahydroxyflavon-3-ol

36. 3'-hydroxykaempferol

37. 3,5,7-trihydroxy-2-(3,4-dihydroxyphenyl)-4h-chromen-4-on

38. Chebi:16243

39. Ai3-26018

40. Nsc9219

41. 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chromen-4-one

42. Nsc-9219

43. Chembl50

44. Mfcd00006828

45. 9ikm0i5t1e

46. 2-(3,4-dihydroxy-phenyl)-3,5,7-trihydroxy-chromen-4-one

47. Ci-75670

48. Nsc-57655

49. Kvercetin [czech]

50. 74893-81-5

51. Ldn-0052529

52. Natural Yellow 10

53. Flavone, 3,4',5,5',7-pentahydroxy-

54. 3,5,7-trihydroxy-2-(3,4-dihydroxyphenyl)-4h-chromen-4-one

55. Dsstox_cid_1218

56. Ci Natural Yellow 10

57. 7255-55-2

58. Dsstox_rid_76017

59. Dsstox_gsid_21218

60. Que

61. Brd9794

62. Brd-9794

63. Cas-117-39-5

64. Nsc57655

65. Nsc58588

66. Sr-01000076098

67. Einecs 204-187-1

68. Unii-9ikm0i5t1e

69. Mixcom3_000183

70. Brn 0317313

71. Ci 75670

72. Ritacetin

73. Quer

74. 4dfu

75. 4mra

76. Quercetin2h2o

77. Meletin;sophoretin

78. Kuc104418n

79. Kuc107684n

80. 3,3',4,5,7-pentahydroxyflavone

81. Quercetin-[d3]

82. Lim-5662

83. Lns-5662

84. Tnp00070

85. Tnp00089

86. Ksc-23-76

87. Quercetin_sathishkumar

88. Ksc-10-126

89. Quercetin (sophoretin)

90. Quercetin - Sophoretin

91. Spectrum_000124

92. Tocris-1125

93. 3cf8

94. Quercetin [dsc]

95. Quercetin [mi]

96. Biomolki_000062

97. Quercetin [hsdb]

98. Quercetin [iarc]

99. Quercetin [inci]

100. Maybridge1_008992

101. Prestwick0_000507

102. Prestwick1_000507

103. Prestwick2_000507

104. Prestwick3_000507

105. Spectrum2_000059

106. Spectrum3_000642

107. Spectrum4_000807

108. Spectrum5_001389

109. Lopac-q-0125

110. Quercetin [vandf]

111. P0042

112. C.i. Natural Yellow 13

113. Biomolki2_000068

114. Enicostemma Littorale Blume

115. Upcmld-dp081

116. Q 0125

117. Quercetin [usp-rs]

118. Quercetin [who-dd]

119. Nciopen2_007628

120. Nciopen2_007882

121. Bidd:pxr0007

122. Lopac0_000999

123. Schembl19723

124. Bspbio_000433

125. Bspbio_001068

126. Bspbio_002243

127. Kbiogr_000408

128. Kbiogr_001293

129. Kbioss_000408

130. Kbioss_000584

131. 5-18-05-00494 (beilstein Handbook Reference)

132. Mls006011766

133. Bidd:er0315

134. Divk1c_000485

135. Schembl219729

136. Spectrum1500672

137. Cu-01000012502-3

138. Spbio_000217

139. Spbio_002354

140. Bdbm7460

141. Bpbio1_000477

142. Gtpl5346

143. Megxp0_000381

144. Sgcut00001

145. 3,4',5,7-pentahydroxyflavone

146. Dtxsid4021218

147. Niosh/lk8760000

148. Upcmld-dp081:001

149. Acon1_000560

150. Hms501i07

151. Kbio1_000485

152. Kbio2_000408

153. Kbio2_000584

154. Kbio2_002976

155. Kbio2_003152

156. Kbio2_005544

157. Kbio2_005720

158. Kbio3_000775

159. Kbio3_000776

160. Kbio3_001463

161. 3,7,3',4'-pentahydroxyflavone

162. Ninds_000485

163. 3',5,7-tetrahydroxyflavan-3-ol

164. Bio1_000369

165. Bio1_000858

166. Bio1_001347

167. Bio2_000374

168. Bio2_000854

169. Hms1362f09

170. Hms1792f09

171. Hms1923o19

172. Hms1990f09

173. Hms3263g19

174. Hms3267m12

175. Hms3414j21

176. Hms3649d04

177. Hms3656c15

178. Hms3678j19

179. To_000078

180. Zinc3869685

181. 3,5,7,3',4'-pentahydroxyflavon

182. Tox21_202308

183. Tox21_300285

184. Tox21_500999

185. Bbl005513

186. Ccg-40054

187. Flavone,3',4',5,7-pentahydroxy-

188. Lmpk12110004

189. Nsc 57655

190. Nsc324608

191. Nsc756660

192. S2391

193. Stk365650

194. Quercetin, >=95% (hplc), Solid

195. 3,4',5,5',7-pentahydroxy-flavone

196. Akos000511724

197. Quercetin 1000 Microg/ml In Acetone

198. Cs-3981

199. Db04216

200. Ds-3416

201. Lp00999

202. Nsc-756660

203. Sdccgsbi-0050972.p003

204. Idi1_000485

205. Idi1_002129

206. Ldn 0052529

207. Smp1_000252

208. Ncgc00015870-01

209. Ncgc00015870-02

210. Ncgc00015870-03

211. Ncgc00015870-04

212. Ncgc00015870-05

213. Ncgc00015870-06

214. Ncgc00015870-07

215. Ncgc00015870-08

216. Ncgc00015870-09

217. Ncgc00015870-10

218. Ncgc00015870-11

219. Ncgc00015870-12

220. Ncgc00015870-13

221. Ncgc00015870-14

222. Ncgc00015870-15

223. Ncgc00015870-16

224. Ncgc00015870-17

225. Ncgc00015870-18

226. Ncgc00015870-19

227. Ncgc00015870-21

228. Ncgc00015870-22

229. Ncgc00015870-23

230. Ncgc00015870-24

231. Ncgc00015870-25

232. Ncgc00015870-28

233. Ncgc00015870-48

234. Ncgc00015870-50

235. Ncgc00025016-01

236. Ncgc00025016-02

237. Ncgc00025016-03

238. Ncgc00025016-04

239. Ncgc00025016-05

240. Ncgc00025016-06

241. Ncgc00025016-07

242. Ncgc00025016-08

243. Ncgc00168962-01

244. Ncgc00168962-02

245. Ncgc00168962-03

246. Ncgc00168962-04

247. Ncgc00254218-01

248. Ncgc00259857-01

249. Ncgc00261684-01

250. Quercetin 100 Microg/ml In Acetonitrile

251. Ac-19596

252. Ac-29756

253. Hy-18085

254. Nci60_042036

255. Smr000112559

256. Sy057722

257. (+)-3,3',4',5,7-pentahydroxyflavone

258. Quercetin, Sophoretin, Meletin, Quercetine

259. Eu-0100999

260. Ft-0603318

261. Ft-0655108

262. Lk87600000

263. N1841

264. Q0025

265. Sw148203-4

266. Quercetin; 3,3',4',5,7-pentahydroxyflavone

267. 17q395

268. C00389

269. K00029

270. S00057

271. Quercetin (constituent Of Ginkgo) [dsc]

272. Wln: T66 Bo Evj Cr Cq Dq & Dq Gq Iq

273. Flavone, 3,3',4',5,7-pentahydroxy-, (+)-

274. Q409478

275. Q-200333

276. Sr-01000076098-1

277. Sr-01000076098-3

278. Sr-01000076098-7

279. Sr-01000076098-8

280. Brd-k97399794-001-02-1

281. Brd-k97399794-001-07-0

282. Brd-k97399794-001-09-6

283. Brd-k97399794-001-11-2

284. Brd-k97399794-335-03-1

285. Sr-01000076098-11

286. 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chromone;hydrate

287. 49643640-fd4c-4b93-bd28-0d7c2021cc52

288. 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4h-chromen-4-one #

289. Quercetin (constituent Of Hawthorn Leaf With Flower) [dsc]

290. (+)-4h-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-

291. 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4h-benzopyran-4-one

292. 4h-1-benzopyran-4-one,2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-,zirconium(2+)salt(1:1)

293. 4h-1-benzopyran-4-one,2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-, Zirconium(2+) Salt (1:1)

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₁₀O₇
Molecular Weight	302.23 g/mol
XLogP3	1.5
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	1
Exact Mass	302.04265265 g/mol
Monoisotopic Mass	302.04265265 g/mol
Topological Polar Surface Area	127 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	488
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Therapeutic Uses

Quercetin has been used in medicine to decrease capillary fragility.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V73 P498 (1999)

/EXPL THER/ ... In a randomized, double-blind, placebo-controlled trial ... /among patients with category III chronic prostatitis syndromes (nonbacterial chronic prostatitis and prostatodynia)/ ... Significant improvement was achieved in the treated group, as measured by the NIH chronic prostatitis score. Some 67% of the treated subjects had at least 25% improvement in symptoms, compared with 20% of the placebo group achieving this same level of improvement. In a follow up, unblind, open-label study ... quercetin was combined with bromelain and papain, which may enhance its absorption. In this study, 82% achieved a minimum 25% improvement score.

Thomson Healthcare. PDR for Nutritional Supplements. Thomson Health Care Inc. Montvale, NJ. p.393 (2001)

/EXPL THER/ Lymphocyte protein kinase phosphorylation was inhibited by quercetin in 9 of 11 cancer patients in a phase I clinical trial. Fifty-one patients with microscopically confirmed cancer not amenable to standard therapies and with a life expectancy of at least 12 wk participated in this trial ... The patients were treated at 3-wk intervals at the beginning of the study. Quercetin was admin iv as quercetin dihydrate ... The max allowed dose was reached when 2 of 3 patients on each dose schedule reached grade 3 or 4 general toxicity, or grad 2 renal toxicity, cardiac toxicity, or neurotoxicity. Phosphorylation was inhibited at 1 hr and persisted for 16 hr. In one patient with ovarian cancer refractory to cisplatin, cancer antigen-125 (CA 125) fell from 295 to 55 units/mL after treatment with 2 courses of quercetin ... A hepatoma patient had serum alpha-fetoprotein fall.

Thomson Healthcare. PDR for Herbal Medicines 4th Ed. Thomson Health Care Inc. Montvale, NJ. 2008, p. 1002

/EXPL THER/ ... Quercetin was reported to inhibit tumor necrosis factor-alpha (TNF-alpha) overproduction and attenuate pathophysiological conditions during acute and chronic inflammation ... In asthma, the activation of mast cells and basophils by allergen releases chemical mediators and synthesizeds cytokines leading to inflammatory conditions ... Quercetin was reported to inhibit cytokine expression and synthesis by human basophils ... A metabolite of quercetin, 3-O-methylquercetin (3-MQ), was reported to provide beneficial effects on asthma by inhibiting cAMP- and cGMP-phosphodiesterase (PDE). ...

Coates, P.M., Blackman, M.R., Cragg, G.M., Levine, M., Moss, J., White, J.D. (Ed), Encyclopedia of Dietary Supplements. Marcel Dekker, New York, NY, p. 580 (2005)

4.2 Drug Warning

Although quercetin seems to have potential as an anticancer agent, future studies are needed, because most studies are based on in vitro experiments using high concn of quercetin unachievable by dietary ingestion, and because its beneficial effects on cancer are still inconclusive in animal and/or human studies.

Coates, P.M., Blackman, M.R., Cragg, G.M., Levine, M., Moss, J., White, J.D. (Ed), Encyclopedia of Dietary Supplements. Marcel Dekker, New York, NY, p. 580 (2005)

... Quercetin has been shown to protect low density lipoprotein (LDL) from oxidation and prevent platelet aggregation. It was also reported to inhibit the proliferation and migration of smooth muscle cells ... Quercetin was reported to significantly lower the plasma lipid, lipoprotein and hepatic cholesterol levels, inhibit the production of oxLDL produced by oxidative stress, and protect an enzyme, which can hydrolyzed specific lipid peroxides in oxidized lipoproteins and in atherosclerotic lesions ... /It/ induced endothelium-dependent vasorelaxation in rat aorta via incr nitric oxide production ... Quercetin and its glycosides were also reported to inhibit the angiotensin-converting enzyme activity, and ANG II-induced JNK activation inducing vascular smooth muscle cell (VSMC) hypertrophy ... However, some effects may not be feasible or negligible in physiological conditions, because concn of quercetin in most studies are too high to be achieved by dietary ingestion ... and beneficial effects of quercetin on cardiovascular diseases are still inconclusive in human studies ...

Coates, P.M., Blackman, M.R., Cragg, G.M., Levine, M., Moss, J., White, J.D. (Ed), Encyclopedia of Dietary Supplements. Marcel Dekker, New York, NY, p. 580 (2005)

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antioxidants

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)

5.2 Absorption, Distribution and Excretion

After oral administration of a single dose of 4 g quercetin to four male and two female volunteers, neither quercetin nor its conjugates was detected in the blood or urine during the first 24 hr; 53% of the dose was recovered in the feces within 72 hr. After a single intravenous injection of 100 mg quercetin to six volunteers, the blood plasma levels declined biphasically, with half-lives of 8.8 min and 2.4 hr; protein binding exceeded 98%. In the urine, 0.65% of the intravenous dose was excreted as unchanged quercetin and 7.4% as a conjugate within 9 hr; no further excretion occurred up to 24 hr ...

When 14C-quercetin was administered orally to ACI rats, about 20% of the administered dose was absorbed from the digestive tract, more than 30% was decomposed to yield 14-CO2 & about 30% was excreted unchanged in feces..

PMID:6876476 UENO K ET AL; JPN J EXP MED 53(1): 41 (1983)

One male and one female volunteer were given a diet containing quercetin glucosides (64.2 mg expressed as the aglycone). The mean peak plasma concentration of quercetin was 196 ng/mL which was reached 2.9 hr after ingestion. The time-course of the plasma concentration of quercetin was biphasic, with half-lives of 3.8 hr for the distribution phase and 16.8 hr for the elimination phase. Quercetin was still present in plasma 48 hr after ingestion ... /Quercetin glucosides/

Autoradiographic analysis of a fasted rat 3 hr after administration of a single oral dose of 2.3 mg/kg (4-(14)C)quercetin showed that although most of the radiolabel remained in the digestive tract it also occurred in blood, liver, kidney, lung and ribs. After oral administration of 630 mg/kg of the labelled compound to rats, 34% of the radiolabel excreted within 24 hr ... was expired carbon dioxide, 12% in bile and 9% in urine; within 48 hr, 45% was recovered in the feces. Approximately 60% of the radiolabel in the feces was identified as unmetabolized quercetin ...

For more Absorption, Distribution and Excretion (Complete) data for QUERCETIN (9 total), please visit the HSDB record page.

5.3 Metabolism/Metabolites

The glycosides are hydrolyzed in the body to corresponding aglycones, which are then further metabolized by scission of the heterocyclic ring to give 3,4-dihydroxy-phenyl-substituted acids ... The site of ring scission depends on structure ... with flavonols (quercetin) scission occurs at the 1,2 & 3,4 bonds to yield homoprotocatechuic acid ... These acids are further metabolized by beta-oxidation of acyl side-chain, o-methylation & demethylation, & aromatic dehydroxylation.

Parke, D. V. The Biochemistry of Foreign Compounds. Oxford: Pergamon Press, 1968., p. 151

o-Beta-hydroxyethylated derivatives of quercetin were isolated from urine samples & separated by HPLC. The 5,7,3',4'-tetra compd was separated from 3,7,3',4'-tetra derivative. The 7,3',4'-tri & 7'-mono compounds gave 1 common peak, separated from the peak for the 7,4'-di compd.

KUHNZ W ET AL; STUD ORG CHEM (AMSTERDAM) 11(FLAVONOIDS BIOFLAVONOIDS): 293 (1982)

After oral admin to ACI rats, the absorbed (14)C-quercetin was rapidly excreted into the bile & urine within 48 hr as the glucuronide & sulfate conjugates of (14)C-quercetin, 3'-o-monomethyl quercetin & 4'-o-monomethyl quercetin. Efficient metabolism and elimination of quercetin may be one reason for the lack of carcinogenicity in rats.

PMID:6876476 UENO K ET AL; JPN J EXP MED 53(1): 41 (1983)

The metabolites of quercetin flavonols identified in urine samples collected from two male volunteers who consumed their habitual diets for three days were 3,4-dihydroxyphenylacetic acid, meta-hydroxyphenylacetic acid, and 4-hydroxy-3-methoxyphenylacetic acid ...

For more Metabolism/Metabolites (Complete) data for QUERCETIN (10 total), please visit the HSDB record page.

Quercetin has known human metabolites that include Dihydroquercetin and Mikwelianin.

Quercetin is a known human metabolite of Quercitrin and tamarixetin.

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

5.4 Biological Half-Life

One male and one female volunteer were given a diet containing quercetin glucosides (64.2 mg expressed as the aglycone) ... Half-lives /were/ 3.8 hr for the distribution phase and 16.8 hr for the elimination phase ... /Quercetin glucosides/

...The elimination half-life of quercetin is approx 25 hr.

Thomson Healthcare. PDR for Nutritional Supplements. Thomson Health Care Inc. Montvale, NJ. p.391 (2001)

5.5 Mechanism of Action

Quercetin is a specific quinone reductase 2 (QR2) inhibitor, an enzyme (along with the human QR1 homolog) which catalyzes metabolism of toxic quinolines. Inhibition of QR2 in plasmodium may potentially cause lethal oxidative stress. The inhibition of antioxidant activity in plasmodium may contribute to killing the malaria causing parasites.

... The 5, 7, 3', 4'-hydroxyl groups on quercetin are capable of donating electrons to quench various radical oxygen species (ROS) and other radical species ... Oxygen radicals (superoxide, hydrogen peroxide, hydroxyl radicals, and other related radicals) ... are quenched by ... antioxidant systems, including antioxidant cmpd, which balance cellular redox status involved in cellular processes for cell homeostasis ... Generally, 3 criteria are considered to assess the antioxidant activity of flavonoids in vitro: first, B ring with 2 hydroxyl groups (adjacent), second, C ring with 2,3-double bond, 4-oxo, and 3-hydroxyl group, and third, A ring with 5,7-dihydroxyl groups. Quercetin meets all 3 criteria, indicating stronger antioxidant activity ... The flavonol was reported to prevent radicals from damaging carbohydrates, proteins, nucleotides, and lipids ... The glucuronide conjugates found in the plasma were also reported to have potent antioxidant activity, indicating that the activity may be retained depending on conjugation positions ...

Coates, P.M., Blackman, M.R., Cragg, G.M., Levine, M., Moss, J., White, J.D. (Ed), Encyclopedia of Dietary Supplements. Marcel Dekker, New York, NY, p. 579 (2005)

Cytokines such as tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) can induce apoptosis in colon cancer cells through engagement of death receptors. Nevertheless, evading apoptosis induced by anticancer drugs characterizes many types of cancers. This results in the need for combination therapy. In this study ... whether the flavonoid quercetin could sensitize human colon adenocarcinoma cell lines to TRAIL-induced apoptosis /was investigated/ ... Quercetin enhanced TRAIL-induced apoptosis by causing the redistribution of DR4 and DR5 into lipid rafts. Nystatin, a cholesterol-sequestering agent, prevented quercetin-induced clustering of death receptors and sensitization to TRAIL-induced apoptosis in colon adenocarcinoma cells ... Qercetin, in combination with TRAIL, triggered the mitochondrial-dependent death pathway, as shown by Bid cleavage and the release of cytochrome c to the cytosol. Together /the/ findings propose that quercetin, through its ability to redistribute death receptors at the cell surface, facilitates death-inducing signaling complex formation and activation of caspases in response to death receptor stimulation. Based on these results, this study provides a challenging approach to enhance the efficiency of TRAIL-based therapies.

PMID:17876056 Psahoulia FH et al; Mol Cancer Ther 6(9):2591-9 (2007)

Previously /the authors/ reported that isoflavone (genistein) activated bone sialoprotein (BSP) gene transcription is mediated through an inverted CCAAT box in the proximal BSP gene promoter. The present study investigates the regulation of BSP transcription in a rat osteoblast-like cell line, ROS 17/2.8 cells, by quercetin and its conjugated metabolite quercetin 3-glucuronide. Quercetin and quercetin 3-glucuronide (5 uM) increased the BSP mRNA levels at 12 hr and quercetin upregulated the Cbfa1/Runx2 mRNA expression at 12 hr. From transient transfection assays using various sized BSP promoter-luciferase constructs, quercetin increased the luciferase activity of the construct (pLUC3), including the promoter sequence nucleotides -116 to -43. Transcriptional stimulations by quercetin were almost completely abrogated in the constructs that included 2 bp mutations in the inverted CCAAT and FRE elements whereas the CCAAT-protein complex did not change after stimulation by quercetin according to gel shift assays. Quercetin increased the nuclear protein binding to the FRE and 3'-FRE. These data suggest that quercetin and quercetin 3-glucuronide increased the BSP mRNA expression, and that the inverted CCAAT and FRE elements in the promoter of the BSP gene are required for quercetin induced BSP transcription.

PMID:17243115 Kim DS et al; J Cell Biochem 101(3):790-800 (2007)

Connexin proteins form gap junctions, which permit direct exchange of cytoplasmic contents between neighboring cells. Evidence indicates that gap junctional intercellular communication (GJIC) is important for maintaining homeostasis and preventing cell transformation. Furthermore, connexins may have independent functions including tumor growth suppression. Most tumors express less connexins, have reduced GJIC and have increased growth rates compared with non-tumorigenic cells. The purpose of this study was to determine whether common flavonoids, genistein and quercetin, increase connexin43 (Cx43) levels, improve GJIC and suppress growth of a metastatic human breast tumor cell line (MDA-MB-231). Quercetin (2.5, 5 ug/mL) and genistein (0.5, 2.5, 15 ug/mL) upregulated Cx43 but failed to increase GJIC. Cx43 localized to the plasma membrane following genistein treatment (2.5, 15 ug/mL). In contrast, Cx43 aggregated in the perinuclear region following quercetin treatment (0.5, 2.5, 5, 15 ug/mL). Both genistein (15 ug/mL) and quercetin (2.5, 5, 15 ug/mL) significantly reduced MDA-MB-231 cell proliferation. In summary, genistein and quercetin increase Cx43 and suppress MDA-MB-231 cell proliferation at physiologically relevant concentrations. These results demonstrate that genistein and quercetin are potential anti-breast cancer agents.

PMID:16777995 Conklin CM et al; Carcinogenesis 28(1):93-100 (2007)

For more Mechanism of Action (Complete) data for QUERCETIN (12 total), please visit the HSDB record page.

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