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Biotransformed Metabolites of the Hop Prenylflavanone Isoxanthohumol.
Molecules. 2019 Jan 22; 24(3)M

Abstract

A metabolic conversion study on microbes is known as one of the most useful tools to predict the xenobiotic metabolism of organic compounds in mammalian systems. The microbial biotransformation of isoxanthohumol (1), a major hop prenylflavanone in beer, has resulted in the production of three diastereomeric pairs of oxygenated metabolites (2⁻7). The microbial metabolites of 1 were formed by epoxidation or hydroxylation of the prenyl group, and HPLC, NMR, and CD analyses revealed that all of the products were diastereomeric pairs composed of (2S)- and (2R)- isomers. The structures of these metabolic compounds were elucidated to be (2S,2"S)- and (2R,2"S)-4'-hydroxy-5-methoxy-7,8-(2,2-dimethyl-3-hydroxy-2,3-dihydro-4H-pyrano)-flavanones (2 and 3), (2S)- and (2R)-7,4'-dihydroxy-5-methoxy-8-(2,3-dihydroxy-3-methylbutyl)-flavanones (4 and 5) which were new oxygenated derivatives, along with (2R)- and (2S)-4'-hydroxy-5-methoxy-2"-(1-hydroxy-1-methylethyl)dihydrofuro[2,3-h]flavanones (6 and 7) on the basis of spectroscopic data. These results could contribute to understanding the metabolic fates of the major beer prenylflavanone isoxanthohumol that occur in mammalian system.

Authors+Show Affiliations

College of Pharmacy and Natural Medicine Research Institute, Mokpo National University, Muan, Jeonnam 58554, Korea. hyunkim@mokpo.ac.kr.Department of Pharmaceutical Engineering, Dongshin University, Naju, Jeonnam 58245, Korea. virshyim@dsu.ac.kr.College of Pharmacy, Chonnam National University, Gwangju 61186, Korea. hanfubo0306@gmail.com.College of Pharmacy, Chonnam National University, Gwangju 61186, Korea. bykang@chonnam.ac.kr.College of Pharmacy and Institute of Pharmaceutical Sciences, CHA University, Seongnam, Gyeonggi-do 13488, Korea. hjchoi3@cha.ac.kr.New Drug Targets Laboratory, School of Life Sciences, Gwangju Institute of Science and Technology, Gwangju 61005, Korea. jung@gist.ac.kr.New Drug Targets Laboratory, School of Life Sciences, Gwangju Institute of Science and Technology, Gwangju 61005, Korea. darren@gist.ac.kr.Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, MD 21702-1201, USA. gustafki@mail.nih.gov.Department of Biological Sciences, Lehman College, City University of New York, Bronx, NY 10468, USA. edward.kennelly@lehman.cuny.edu.College of Pharmacy, Chonnam National University, Gwangju 61186, Korea. islee@chonnam.ac.kr.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

30678278

Citation

Kim, Hyun Jung, et al. "Biotransformed Metabolites of the Hop Prenylflavanone Isoxanthohumol." Molecules (Basel, Switzerland), vol. 24, no. 3, 2019.
Kim HJ, Yim SH, Han F, et al. Biotransformed Metabolites of the Hop Prenylflavanone Isoxanthohumol. Molecules. 2019;24(3).
Kim, H. J., Yim, S. H., Han, F., Kang, B. Y., Choi, H. J., Jung, D. W., Williams, D. R., Gustafson, K. R., Kennelly, E. J., & Lee, I. S. (2019). Biotransformed Metabolites of the Hop Prenylflavanone Isoxanthohumol. Molecules (Basel, Switzerland), 24(3). https://doi.org/10.3390/molecules24030394
Kim HJ, et al. Biotransformed Metabolites of the Hop Prenylflavanone Isoxanthohumol. Molecules. 2019 Jan 22;24(3) PubMed PMID: 30678278.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Biotransformed Metabolites of the Hop Prenylflavanone Isoxanthohumol. AU - Kim,Hyun Jung, AU - Yim,Soon-Ho, AU - Han,Fubo, AU - Kang,Bok Yun, AU - Choi,Hyun Jin, AU - Jung,Da-Woon, AU - Williams,Darren R, AU - Gustafson,Kirk R, AU - Kennelly,Edward J, AU - Lee,Ik-Soo, Y1 - 2019/01/22/ PY - 2018/12/30/received PY - 2019/01/18/revised PY - 2019/01/20/accepted PY - 2019/1/26/entrez PY - 2019/1/27/pubmed PY - 2019/4/24/medline KW - hop prenylflavanone KW - isoxanthohumol KW - microbial transformation JF - Molecules (Basel, Switzerland) JO - Molecules VL - 24 IS - 3 N2 - A metabolic conversion study on microbes is known as one of the most useful tools to predict the xenobiotic metabolism of organic compounds in mammalian systems. The microbial biotransformation of isoxanthohumol (1), a major hop prenylflavanone in beer, has resulted in the production of three diastereomeric pairs of oxygenated metabolites (2⁻7). The microbial metabolites of 1 were formed by epoxidation or hydroxylation of the prenyl group, and HPLC, NMR, and CD analyses revealed that all of the products were diastereomeric pairs composed of (2S)- and (2R)- isomers. The structures of these metabolic compounds were elucidated to be (2S,2"S)- and (2R,2"S)-4'-hydroxy-5-methoxy-7,8-(2,2-dimethyl-3-hydroxy-2,3-dihydro-4H-pyrano)-flavanones (2 and 3), (2S)- and (2R)-7,4'-dihydroxy-5-methoxy-8-(2,3-dihydroxy-3-methylbutyl)-flavanones (4 and 5) which were new oxygenated derivatives, along with (2R)- and (2S)-4'-hydroxy-5-methoxy-2"-(1-hydroxy-1-methylethyl)dihydrofuro[2,3-h]flavanones (6 and 7) on the basis of spectroscopic data. These results could contribute to understanding the metabolic fates of the major beer prenylflavanone isoxanthohumol that occur in mammalian system. SN - 1420-3049 UR - https://www.unboundmedicine.com/medline/citation/30678278/Biotransformed_Metabolites_of_the_Hop_Prenylflavanone_Isoxanthohumol_ L2 - http://www.mdpi.com/resolver?pii=molecules24030394 DB - PRIME DP - Unbound Medicine ER -