Skip to main content
PMC home page
Applied and Environmental Microbiology logoLink to Applied and Environmental Microbiology
. 1989 May;55(5):1203–1208. doi: 10.1128/aem.55.5.1203-1208.1989

C-ring cleavage of flavonoids by human intestinal bacteria.

J Winter 1, L H Moore 1, V R Dowell Jr 1, V D Bokkenheuser 1
PMCID: PMC184277  PMID: 2757380

Abstract

Four hitherto undescribed Clostridium strains capable of cleaving the C ring of quercetin, kaempferol, and naringenin at C-3-C-4 were isolated from the fecal flora of humans. None of the strains cleaved catechin. C-ring fission occurred when the substrate was either in solution or in suspension. Mixed cultures of flavonoid-hydrolyzing bacteria, flavonoid-cleaving bacteria, and Escherichia coli, which was used to provide the anaerobic environment, rapidly metabolized rutin to 3,4-dihydroxyphenylacetic acid, indicating that the intestinal half-life of the biologically active aglycone is short. The cleaving strains shared many phenotypic characteristics, including their inability to ferment sugars, but they differed sufficiently to indicate that they represent different species.

Full text

PDF
1203

Images in this article

1205Image
on p.1205

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. BOOTH A. N., DEEDS F., JONES F. T., MURRAY C. W. The metabolic fate of rutin and quercetin in the animal body. J Biol Chem. 1956 Nov;223(1):251–257. [PubMed] [Google Scholar]
  2. Bokkenheuser V. D., Morris G. N., Ritchie A. E., Holdeman L. V., Winter J. Biosynthesis of androgen from cortisol by a species of Clostridium recovered from human fecal flora. J Infect Dis. 1984 Apr;149(4):489–494. doi: 10.1093/infdis/149.4.489. [DOI] [PubMed] [Google Scholar]
  3. Bokkenheuser V. D., Shackleton C. H., Winter J. Hydrolysis of dietary flavonoid glycosides by strains of intestinal Bacteroides from humans. Biochem J. 1987 Dec 15;248(3):953–956. doi: 10.1042/bj2480953. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Bokkenheuser V. D., Winter J., Cohen B. I., O'Rourke S., Mosbach E. H. Inactivation of contraceptive steroid hormones by human intestinal clostridia. J Clin Microbiol. 1983 Sep;18(3):500–504. doi: 10.1128/jcm.18.3.500-504.1983. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Bokkenheuser V. D., Winter J., Dehazya P., de Leon O., Kelly W. G. Formation and metabolism of tetrahydrodeoxycorticosterone by human fecal flora. J Steroid Biochem. 1976 Oct;7(10):837–843. doi: 10.1016/0022-4731(76)90187-4. [DOI] [PubMed] [Google Scholar]
  6. Bokkenheuser V. D., Winter J., Morris G. N., Locascio S. Steroid desmolase synthesis by Eubacterium desmolans and Clostridium cadavaris. Appl Environ Microbiol. 1986 Nov;52(5):1153–1156. doi: 10.1128/aem.52.5.1153-1156.1986. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Cheng K. J., Jones G. A., Simpson F. J., Bryant M. P. Isolation and identification of rumen bacteria capable of anaerobic rutin degradation. Can J Microbiol. 1969 Dec;15(12):1365–1371. doi: 10.1139/m69-247. [DOI] [PubMed] [Google Scholar]
  8. Cheng K. J., Krishnamurty H. G., Jones G. A., Simpson F. J. Identification of products produced by the anaerobic degradation of naringin by Butyrivibrio sp. C3. Can J Microbiol. 1971 Jan;17(1):129–131. doi: 10.1139/m71-022. [DOI] [PubMed] [Google Scholar]
  9. Das N. P., Griffiths L. A. Studies on flavonoid metabolism. Metabolism of (+)-catechin in the guinea pig. Biochem J. 1968 Dec;110(3):449–456. doi: 10.1042/bj1100449. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Glass T. L., Winter J., Bokkenheuser V. D., Hylemon P. B. Biotransformation of 16 alpha-hydroxyprogesterone by Eubacterium sp. 144: non-enzymatic addition of L-cysteine to delta 16-progesterone. J Lipid Res. 1982 Feb;23(2):352–356. [PubMed] [Google Scholar]
  11. Griffiths L. A., Barrow A. Metabolism of flavonoid compounds in germ-free rats. Biochem J. 1972 Dec;130(4):1161–1162. doi: 10.1042/bj1301161. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Kodaka H., Armfield A. Y., Lombard G. L., Dowell V. R., Jr Practical procedure for demonstrating bacterial flagella. J Clin Microbiol. 1982 Nov;16(5):948–952. doi: 10.1128/jcm.16.5.948-952.1982. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Kodaka H., Lombard G. L., Dowell V. R., Jr Gas-liquid chromatography technique for detection of hippurate hydrolysis and conversion of fumarate to succinate by microorganisms. J Clin Microbiol. 1982 Nov;16(5):962–964. doi: 10.1128/jcm.16.5.962-964.1982. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. Krumholz L. R., Bryant M. P. Characterization of the pyrogallol-phloroglucinol isomerase of Eubacterium oxidoreducens. J Bacteriol. 1988 Jun;170(6):2472–2479. doi: 10.1128/jb.170.6.2472-2479.1988. [DOI] [PMC free article] [PubMed] [Google Scholar]
  15. Krumholz L. R., Crawford R. L., Hemling M. E., Bryant M. P. Metabolism of gallate and phloroglucinol in Eubacterium oxidoreducens via 3-hydroxy-5-oxohexanoate. J Bacteriol. 1987 May;169(5):1886–1890. doi: 10.1128/jb.169.5.1886-1890.1987. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. Kühnau J. The flavonoids. A class of semi-essential food components: their role in human nutrition. World Rev Nutr Diet. 1976;24:117–191. [PubMed] [Google Scholar]
  17. Winter J., Bokkenheuser V. D. 21-dehydroxylation of corticoids by anaerobic bacteria isolated from human fecal flora. J Steroid Biochem. 1978 May;9(5):379–384. doi: 10.1016/0022-4731(78)90604-0. [DOI] [PubMed] [Google Scholar]
  18. Winter J., Cerone-McLernon A., O'Rourke S., Ponticorvo L., Bokkenheuser V. D. Formation of 20 beta-dihydrosteroids by anaerobic bacteria. J Steroid Biochem. 1982 Dec;17(6):661–667. doi: 10.1016/0022-4731(82)90568-4. [DOI] [PubMed] [Google Scholar]
  19. Winter J., Morris G. N., O'Rourke-Locascio S., Bokkenheuser V. D., Mosbach E. H., Cohen B. I., Hylemon P. B. Mode of action of steroid desmolase and reductases synthesized by Clostridium "scindens" (formerly Clostridium strain 19). J Lipid Res. 1984 Oct;25(10):1124–1131. [PubMed] [Google Scholar]
  20. Winter J., O'Rourke S., Bokkenheuser V. D., Hylemon P. B., Glass T. L. 16 alpha-dehydration of corticoids by bacteria isolated from rat fecal flora. J Steroid Biochem. 1982 Feb;16(2):231–237. doi: 10.1016/0022-4731(82)90171-6. [DOI] [PubMed] [Google Scholar]

Articles from Applied and Environmental Microbiology are provided here courtesy of American Society for Microbiology (ASM)

RESOURCES