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Volumn 65, Issue 16, 2017, Pages 3305-3310

Curcuminoid Demethylation as an Alternative Metabolism by Human Intestinal Microbiota

Author keywords

curcumin; curcuminoids; demethoxycurcumin; demethylation; human intestinal metabolism; turmeric

Indexed keywords

BIOMOLECULES; CHEMICAL REACTIONS; DERIVATIVES; FOOD PRODUCTS; METABOLITES; PHYSIOLOGY;

EID: 85018849048     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/acs.jafc.7b00943     Document Type: Article
Times cited : (97)

References (29)
  • 1
    • 84921535683 scopus 로고    scopus 로고
    • Curcumin, a component of golden spice: From bedside to bench and back
    • Prasad, S.; Gupta, S. C.; Tyagi, A. K.; Aggarwal, B. B. Curcumin, a component of golden spice: from bedside to bench and back Biotechnol. Adv. 2014, 32, 1053-1064 10.1016/j.biotechadv.2014.04.004
    • (2014) Biotechnol. Adv. , vol.32 , pp. 1053-1064
    • Prasad, S.1    Gupta, S.C.2    Tyagi, A.K.3    Aggarwal, B.B.4
  • 2
    • 0018222291 scopus 로고
    • The metabolism and excretion of curcumin (1,7-bis-(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione) in the rat
    • Holder, G. M.; Plummer, J. L.; Ryan, A. J. The metabolism and excretion of curcumin (1,7-bis-(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione) in the rat Xenobiotica 1978, 8, 761-768 10.3109/00498257809069589
    • (1978) Xenobiotica , vol.8 , pp. 761-768
    • Holder, G.M.1    Plummer, J.L.2    Ryan, A.J.3
  • 3
    • 34548071764 scopus 로고    scopus 로고
    • Isolation and identification of phase 1 metabolites of demethoxycurcumin in rats
    • Zeng, Y.; Qiu, F.; Liu, Y.; Qu, G.; Yao, X. Isolation and identification of phase 1 metabolites of demethoxycurcumin in rats Drug Metab. Dispos. 2007, 35, 1564-1573 10.1124/dmd.107.015008
    • (2007) Drug Metab. Dispos. , vol.35 , pp. 1564-1573
    • Zeng, Y.1    Qiu, F.2    Liu, Y.3    Qu, G.4    Yao, X.5
  • 4
    • 33244473463 scopus 로고    scopus 로고
    • Metabolism of curcuminoids in tissue slices and subcellular fractions from rat liver
    • Hoehle, S. I.; Pfeiffer, E.; Sólyom, A. M.; Metzler, M. Metabolism of curcuminoids in tissue slices and subcellular fractions from rat liver J. Agric. Food Chem. 2006, 54, 756-764 10.1021/jf058146a
    • (2006) J. Agric. Food Chem. , vol.54 , pp. 756-764
    • Hoehle, S.I.1    Pfeiffer, E.2    Sólyom, A.M.3    Metzler, M.4
  • 5
    • 84898040154 scopus 로고    scopus 로고
    • Metabolic and colonic microbiota transformation may enhance the bioactivities of dietary polyphenols
    • Chiou, Y. S.; Wu, J. C.; Huang, Q.; Shahidi, F.; Wang, Y. J.; Ho, C. T.; Pan, M. H. Metabolic and colonic microbiota transformation may enhance the bioactivities of dietary polyphenols J. Funct. Foods 2014, 7, 3-25 10.1016/j.jff.2013.08.006
    • (2014) J. Funct. Foods , vol.7 , pp. 3-25
    • Chiou, Y.S.1    Wu, J.C.2    Huang, Q.3    Shahidi, F.4    Wang, Y.J.5    Ho, C.T.6    Pan, M.H.7
  • 8
    • 79955598016 scopus 로고    scopus 로고
    • Discovery of the curcumin metabolic pathway involving a unique enzyme in an intestinal microorganism
    • Hassaninasab, A.; Hashimoto, Y.; Tomita-Yokotani, K.; Kobayashi, M. Discovery of the curcumin metabolic pathway involving a unique enzyme in an intestinal microorganism Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 6615-6620 10.1073/pnas.1016217108
    • (2011) Proc. Natl. Acad. Sci. U. S. A. , vol.108 , pp. 6615-6620
    • Hassaninasab, A.1    Hashimoto, Y.2    Tomita-Yokotani, K.3    Kobayashi, M.4
  • 10
    • 31344440514 scopus 로고    scopus 로고
    • Curcumin and its analogues as potent inhibitors of low density lipoprotein oxidation: H-atom abstraction from the phenolic groups and possible involvement of the 4-hydroxy-3-methoxyphenyl groups
    • Chen, W. F.; Deng, S. L.; Zhou, B.; Yang, L.; Liu, Z. L. Curcumin and its analogues as potent inhibitors of low density lipoprotein oxidation: H-atom abstraction from the phenolic groups and possible involvement of the 4-hydroxy-3-methoxyphenyl groups Free Radical Biol. Med. 2006, 40, 526-535 10.1016/j.freeradbiomed.2005.09.008
    • (2006) Free Radical Biol. Med. , vol.40 , pp. 526-535
    • Chen, W.F.1    Deng, S.L.2    Zhou, B.3    Yang, L.4    Liu, Z.L.5
  • 11
    • 84978859488 scopus 로고    scopus 로고
    • Polyhydroxycurcuminoids but not curcumin upregulate neprilysin and can be applied to the prevention of Alzheimer's disease
    • Chen, P. T.; Chen, Z. T.; Hou, W. C.; Yu, L. C.; Chen, R. P. Y. Polyhydroxycurcuminoids but not curcumin upregulate neprilysin and can be applied to the prevention of Alzheimer's disease Sci. Rep. 2016, 6, 29760 10.1038/srep29760
    • (2016) Sci. Rep. , vol.6 , pp. 29760
    • Chen, P.T.1    Chen, Z.T.2    Hou, W.C.3    Yu, L.C.4    Chen, R.P.Y.5
  • 12
    • 84953347339 scopus 로고    scopus 로고
    • Association of neuroprotective effect of di-O-demethylcurcumin on Aβ25-35-induced neurotoxicity with suppression of NF-B and activation of Nrf2
    • Pinkaew, D.; Changtam, C.; Tocharus, C.; Govitrapong, P.; Jumnongprakhon, P.; Suksamrarn, A.; Tocharus, J. Association of neuroprotective effect of di-O-demethylcurcumin on Aβ25-35-induced neurotoxicity with suppression of NF-B and activation of Nrf2 Neurotoxic. Res. 2016, 29, 80-91 10.1007/s12640-015-9558-4
    • (2016) Neurotoxic. Res. , vol.29 , pp. 80-91
    • Pinkaew, D.1    Changtam, C.2    Tocharus, C.3    Govitrapong, P.4    Jumnongprakhon, P.5    Suksamrarn, A.6    Tocharus, J.7
  • 13
    • 84920379442 scopus 로고    scopus 로고
    • Di-O-demethylcurcumin protects SK-N-SH cells against mitochondrial and endoplasmic reticulum-mediated apoptotic cell death induced by Aβ 25-35
    • Pinkaew, D.; Changtam, C.; Tocharus, C.; Thummayot, S.; Suksamrarn, A.; Tocharus, J. Di-O-demethylcurcumin protects SK-N-SH cells against mitochondrial and endoplasmic reticulum-mediated apoptotic cell death induced by Aβ 25-35 Neurochem. Int. 2015, 80, 110-119 10.1016/j.neuint.2014.10.008
    • (2015) Neurochem. Int. , vol.80 , pp. 110-119
    • Pinkaew, D.1    Changtam, C.2    Tocharus, C.3    Thummayot, S.4    Suksamrarn, A.5    Tocharus, J.6
  • 14
    • 0018146189 scopus 로고
    • A study on the fate of curcumin in the rat
    • Wahlstrom, B.; Blennow, G. A study on the fate of curcumin in the rat Acta Pharmacol. Toxicol. 1978, 43, 86-92 10.1111/j.1600-0773.1978.tb02240.x
    • (1978) Acta Pharmacol. Toxicol. , vol.43 , pp. 86-92
    • Wahlstrom, B.1    Blennow, G.2
  • 15
    • 84919779924 scopus 로고    scopus 로고
    • Metabolism of Kaempferia parviflora polymethoxyflavones by human intestinal bacterium Blautia sp. MRG-PMF1
    • Kim, M.; Kim, N.; Han, J. Metabolism of Kaempferia parviflora polymethoxyflavones by human intestinal bacterium Blautia sp. MRG-PMF1 J. Agric. Food Chem. 2014, 62, 12377-12383 10.1021/jf504074n
    • (2014) J. Agric. Food Chem. , vol.62 , pp. 12377-12383
    • Kim, M.1    Kim, N.2    Han, J.3
  • 16
    • 84862806476 scopus 로고    scopus 로고
    • Anti-obesity effect of a standardised ethanol extract from Curcuma longa L. Fermented with Aspergillus oryzae in ob/ob mice and primary mouse adipocytes
    • Ho, J. N.; Jang, J. Y.; Yoon, H. G.; Kim, Y.; Kim, S.; Jun, W.; Lee, J. Anti-obesity effect of a standardised ethanol extract from Curcuma longa L. fermented with Aspergillus oryzae in ob/ob mice and primary mouse adipocytes J. Sci. Food Agric. 2012, 92, 1833-1840 10.1002/jsfa.5592
    • (2012) J. Sci. Food Agric. , vol.92 , pp. 1833-1840
    • Ho, J.N.1    Jang, J.Y.2    Yoon, H.G.3    Kim, Y.4    Kim, S.5    Jun, W.6    Lee, J.7
  • 17
    • 84977493572 scopus 로고    scopus 로고
    • Deglycosylation of flavonoid O-glucosides by human intestinal bacteria Enterococcus sp. MRG-2 and Lactococcus sp. MRG-IF-4. Appl
    • Kim, M.; Kim, N.; Han, J. Deglycosylation of flavonoid O-glucosides by human intestinal bacteria Enterococcus sp. MRG-2 and Lactococcus sp. MRG-IF-4. Appl Biol. Chem. 2016, 59, 443-449 10.1007/s13765-016-0183-6
    • (2016) Biol. Chem. , vol.59 , pp. 443-449
    • Kim, M.1    Kim, N.2    Han, J.3
  • 18
    • 85014184358 scopus 로고    scopus 로고
    • Demethylation of ppolymethoxyflavones by human gut bacterium, Blautia sp. MRG-PMF1
    • Burapan, S.; Kim, M.; Han, J. Demethylation of ppolymethoxyflavones by human gut bacterium, Blautia sp. MRG-PMF1 J. Agric. Food Chem. 2017, 65, 1620-1629 10.1021/acs.jafc.7b00408
    • (2017) J. Agric. Food Chem. , vol.65 , pp. 1620-1629
    • Burapan, S.1    Kim, M.2    Han, J.3
  • 19
    • 84871859202 scopus 로고    scopus 로고
    • Probiotic metabolites as epigenetic targets in the prevention of colon cancer
    • Kumar, M.; Nagpal, R.; Verma, V.; Kumar, A.; Kaur, N.; Hemalatha, R.; Gautam, S. K.; Singh, B. Probiotic metabolites as epigenetic targets in the prevention of colon cancer Nutr. Rev. 2013, 71, 23-34 10.1111/j.1753-4887.2012.00542.x
    • (2013) Nutr. Rev. , vol.71 , pp. 23-34
    • Kumar, M.1    Nagpal, R.2    Verma, V.3    Kumar, A.4    Kaur, N.5    Hemalatha, R.6    Gautam, S.K.7    Singh, B.8
  • 20
    • 84930677473 scopus 로고    scopus 로고
    • Deglycosylation of isoflavone C-glycosides by newly isolated human intestinal bacteria
    • Kim, M.; Lee, J.; Han, J. Deglycosylation of isoflavone C-glycosides by newly isolated human intestinal bacteria J. Sci. Food Agric. 2015, 95, 1925-1931 10.1002/jsfa.6900
    • (2015) J. Sci. Food Agric. , vol.95 , pp. 1925-1931
    • Kim, M.1    Lee, J.2    Han, J.3
  • 21
    • 84890696397 scopus 로고    scopus 로고
    • Overview of metabolism and bioavailability enhancement of polyphenols
    • Lewandowska, U.; Szewczyk, K.; Hrabec, E.; Janecka, A.; Gorlach, S. Overview of metabolism and bioavailability enhancement of polyphenols J. Agric. Food Chem. 2013, 61, 12183-12199 10.1021/jf404439b
    • (2013) J. Agric. Food Chem. , vol.61 , pp. 12183-12199
    • Lewandowska, U.1    Szewczyk, K.2    Hrabec, E.3    Janecka, A.4    Gorlach, S.5
  • 22
    • 34548071764 scopus 로고    scopus 로고
    • Isolation and identification of phase 1 metabolites of demethoxycurcumin in rats
    • Zeng, Y.; Qiu, F.; Liu, Y.; Qu, G.; Yao, X. Isolation and identification of phase 1 metabolites of demethoxycurcumin in rats Drug Metab. Dispos. 2007, 35, 1564-1573 10.1124/dmd.107.015008
    • (2007) Drug Metab. Dispos. , vol.35 , pp. 1564-1573
    • Zeng, Y.1    Qiu, F.2    Liu, Y.3    Qu, G.4    Yao, X.5
  • 23
    • 80052629054 scopus 로고    scopus 로고
    • Stereospecific microbial production of isoflavanones from isoflavones and isoflavone glucosides
    • Park, H. Y.; Kim, M.; Han, J. Stereospecific microbial production of isoflavanones from isoflavones and isoflavone glucosides Appl. Microbiol. Biotechnol. 2011, 91, 1173-1181 10.1007/s00253-011-3310-7
    • (2011) Appl. Microbiol. Biotechnol. , vol.91 , pp. 1173-1181
    • Park, H.Y.1    Kim, M.2    Han, J.3
  • 24
    • 77954180759 scopus 로고    scopus 로고
    • Absolute configuration determination of isoflavan-4-ol stereoisomers
    • Kim, M.; Won, D.; Han, J. Absolute configuration determination of isoflavan-4-ol stereoisomers Bioorg. Med. Chem. Lett. 2010, 20, 4337-4341 10.1016/j.bmcl.2010.06.074
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 4337-4341
    • Kim, M.1    Won, D.2    Han, J.3
  • 25
    • 77954203090 scopus 로고    scopus 로고
    • Conversion of (3S,4R)-tetrahydrodaidzein to (3S)-equol by THD reductase: Proposed mechanism involving a radical intermediate
    • Kim, M.; Marsh, E. N. G.; Kim, S. U.; Han, J. Conversion of (3S,4R)-tetrahydrodaidzein to (3S)-equol by THD reductase: proposed mechanism involving a radical intermediate Biochemistry 2010, 49, 5582-5587 10.1021/bi100465y
    • (2010) Biochemistry , vol.49 , pp. 5582-5587
    • Kim, M.1    Marsh, E.N.G.2    Kim, S.U.3    Han, J.4
  • 26
    • 66249090545 scopus 로고    scopus 로고
    • Stereospecific biotransformation of dihydrodaidzein into (3S)-equol by the human intestinal bacterium Eggerthella strain Julong 732
    • Kim, M.; Kim, S. I.; Han, J.; Wang, X. L.; Song, D. G.; Kim, S. U. Stereospecific biotransformation of dihydrodaidzein into (3S)-equol by the human intestinal bacterium Eggerthella strain Julong 732 Appl. Environ. Microbiol. 2009, 75, 3062-3068 10.1128/AEM.02058-08
    • (2009) Appl. Environ. Microbiol. , vol.75 , pp. 3062-3068
    • Kim, M.1    Kim, S.I.2    Han, J.3    Wang, X.L.4    Song, D.G.5    Kim, S.U.6
  • 27
    • 84922245736 scopus 로고    scopus 로고
    • Application of ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry to identify curcumin metabolites produced by human intestinal bacteria
    • Lou, Y.; Zheng, J.; Hu, H.; Lee, J.; Zeng, S. Application of ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry to identify curcumin metabolites produced by human intestinal bacteria J. Chromatogr. B: Anal. Technol. Biomed. Life Sci. 2015, 985, 38-47 10.1016/j.jchromb.2015.01.014
    • (2015) J. Chromatogr. B: Anal. Technol. Biomed. Life Sci. , vol.985 , pp. 38-47
    • Lou, Y.1    Zheng, J.2    Hu, H.3    Lee, J.4    Zeng, S.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.