본문 바로가기
KERD
논문KCI 등재

Hydroxylation of Resveratrol with DoxA In Vitro: An Enzyme with the Potential for the Bioconversion of a Bioactive Stilbene

2

조회

0

다운로드

1

인용

0

참고문헌

키워드

주제분류생물학

초록

The late-stage doxorubicin biosynthesis pathway acting enzyme (DoxA) from Streptomyces peucetius CYP129A2 exhibited substrate promiscuity towards the stilbene group of compounds such as resveratrol. DoxA along with two accessory enzymes ferrdoxin reductase and ferredoxin from spinach hydroxylated resveratrol at the 3’-position in vitro to produce piceatannol. The product was identified by HPLC-PDA and high-resolution HR-qTOF-ESI/ MS analyses in positive mode. The ESI/MS fragments resembled the hydroxylated product of resveratrol.

Abstract

The late-stage doxorubicin biosynthesis pathway acting enzyme (DoxA) from Streptomyces peucetius CYP129A2 exhibited substrate promiscuity towards the stilbene group of compounds such as resveratrol. DoxA along with two accessory enzymes ferrdoxin reductase and ferredoxin from spinach hydroxylated resveratrol at the 3’-position in vitro to produce piceatannol. The product was identified by HPLC-PDA and high-resolution HR-qTOF-ESI/ MS analyses in positive mode. The ESI/MS fragments resembled the hydroxylated product of resveratrol.

참고문헌 (15)

  1. Sirerol JA, "Role of natural stilbenes in the prevention of cancer", Oxid. Med. Cell Longev., 2016 (2016)
  2. Lin Y, "Biotechnological production of plant-specific hydroxylated phenylpropanoids", Biotechnol. Bioeng., 111, pp.1895~1899 (2014)[DOI]
  3. Brisdelli F, "Resveratrol: a natural polyphenol with multiple chemopreventive properties", Curr. Drug Metab., 10, pp.530~546 (2009)[DOI]
  4. Potter GA, "The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYP1B1", Br. J. Cancer, 86, pp.774~778 (2002)[DOI]
  5. Piotrowska H, "Biological activity of piceatannol: leaving the shadow of resveratrol", Mutat. Res., 750, pp.60~82 (2012)[DOI]
  6. Seyed MA, "Comprehensive review on the chemotherapeutic potential of piceatannol for cancer treatment, with mechanistic insights", J. Agric. Food Chem., 64, pp.725~737 (2016)[DOI]
  7. Furuya T, "Biocatalytic synthesis of 3,4,5,3',5'-pentahydroxy-trans-stilbene from piceatannol by two-component flavin-dependent monooxygenase HpaBC", Biosci. Biotechnol. Biochem., 80, pp.193~198 (2015)
  8. Walczak RJ, "Purification, properties, and characterization of recombinant Streptomyces sp. strain C5 DoxA, a cytochrome P-450 catalyzing multiple steps in doxorubicin biosynthesis", J. Bacteriol., 181, pp.298~304 (1999)
  9. Dickens ML, "In vivo and in vitro bioconversion of <TEX>$\varepsilon$<", TEX>-rhodomycinone glycoside to doxorubicin: functions of DauP, DauK, and DoxA, 1997, pp.179, 2641~2650
  10. Rimal H, "Understanding of real alternative redox partner of Streptomyces peucetius DoxA: prediction and validation using in silico and in vitro analyses", Arch. Biochem. Biophys., 585, pp.64~74 (2015)[DOI]
  11. Omura T, "The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature", J. Biol. Chem., 239, pp.2370~2378 (1964)
  12. (-) species of resveratrol and piceatannol investigated by deuterium labelling and accurate mass measurements, "Rapid Commun. Mass Spectrom.", 2008, 3867~3872, 10.1002[DOI]
  13. Bavaresco L, "The occurrence of the stilbene piceatannol in grapes", Vitis, 41, pp.133~136 (2002)
  14. Wishart DS, "HMDB 4.0: the human metabolome database for 2018", Nucleic Acids Res., 46, pp.D608~D617 (2018)[DOI]
  15. Khatri Y, "Structural characterization of CYP260A1 from Sorangium cellulosum to investigate the <TEX>$1{\alpha}$<", TEX>-hydroxylation of a mineralocorticoid, 2016, pp.590, 4638~4648

관련 논문AI추천

이 간행물의 다른 논문 (9건)