Neohesperidin Dihydrochalcone Degradation
J. Agric. Food Chem., Vol. 53, No. 5, 2005 1789
rhamnoglucosides to the respective phenolic acids. Therefore,
the transformation of these flavonoid glycosides is probably
brought about by cooperative action of different bacterial species
present in the complex intestinal microbiota. For example, the
cleavage of hesperidin by methanogenic consortia enriched from
digested municipal sludge led to the formation of phloroglucinol,
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Anaerobic degradation of flavonoids by Clostridium orbiscin-
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3-(3,4-dihydroxyphenyl)propionic acid, and 3-(3-hydroxy-4-
methoxyphenyl)propionic acid as a transient intermediate (51).
Since only bacteria are able to attack flavonoid rhamnogluco-
sides and the absorption of these glycosides has not been
observed in most of the studies performed, it may be concluded
that the bioavailability of neohesperidin dihydrochalcone and
similar compounds depends on the activity of gut bacteria.
However, in one human study a fraction of only 0.02% of the
administered dose of naringin was recovered intact from urine
(
(
(
(30). When released from the bacteria, the glucosides or
aglycons formed can be either absorbed by the human host or
further transformed by other gut bacteria. However, the cleavage
of flavonoid structures as shown for hesperetin dihydrochalcone
by E. ramulus and C. orbiscindens herein is exclusively
catalyzed by bacterial enzymes. By releasing phenolic acids,
such as 3-(3-hydroxy-4-methoxyphenyl)propionic and 3-(3,4-
hydroxyphenyl)propionic acid, bacteria influence not only the
bioavailability but also the effects of the ingested flavonoids
considered to be bioactive.
(19) Bloor, S. J. Overview of methods for analysis and identification
of flavonoids. Methods Enzymol. 2001, 335, 3-14.
(20) Robinson, R.; Sugasawa, S. Preliminary synthetical experiments
in the morphin group, Part I. J. Chem. Soc. 1931, 3136-3172.
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Richards, R. K. Local anesthetics. IV. The synthesis of local
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(
22) Braune, A.; G u¨ tschow, M.; Engst, W.; Blaut, M. Degradation
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Microbiol. 2001, 67, 5558-5567.
ACKNOWLEDGMENT
We are indebted to Michael G u¨ tschow (Pharmaceutical Institute,
University of Bonn, Germany) for synthesis of 3-(3-hydroxy-
(23) Schneider, H.; Schwiertz, A.; Collins, M. D.; Blaut, M. Anaerobic
transformation of quercetin-3-glucoside by bacteria from the
human intestinal tract. Arch. Microbiol. 1999, 171, 81-91.
4
-methoxyphenyl)propionic acid and performing the NMR
(24) Herles, C.; Braune, A.; Blaut, M. First bacterial chalcone
analyses. We thank Sabine Zimmerman for technical assistance.
isomerase isolated from Eubacterium ramulus. Arch. Microbiol.
2
004, 181, 428-434.
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