Identification of a flavin-containing S-oxygenating monooxygenase involved in alliin biosynthesis in garlic

The Plant Journal : for Cell and Molecular Biology
Naoko YoshimotoKazuki Saito

Abstract

S-Alk(en)yl-l-cysteine sulfoxides are cysteine-derived secondary metabolites highly accumulated in the genus Allium. Despite pharmaceutical importance, the enzymes that contribute to the biosynthesis of S-alk-(en)yl-l-cysteine sulfoxides in Allium plants remain largely unknown. Here, we report the identification of a flavin-containing monooxygenase, AsFMO1, in garlic (Allium sativum), which is responsible for the S-oxygenation reaction in the biosynthesis of S-allyl-l-cysteine sulfoxide (alliin). Recombinant AsFMO1 protein catalyzed the stereoselective S-oxygenation of S-allyl-l-cysteine to nearly exclusively yield (RC SS )-S-allylcysteine sulfoxide, which has identical stereochemistry to the major natural form of alliin in garlic. The S-oxygenation reaction catalyzed by AsFMO1 was dependent on the presence of nicotinamide adenine dinucleotide phosphate (NADPH) and flavin adenine dinucleotide (FAD), consistent with other known flavin-containing monooxygenases. AsFMO1 preferred S-allyl-l-cysteine to γ-glutamyl-S-allyl-l-cysteine as the S-oxygenation substrate, suggesting that in garlic, the S-oxygenation of alliin biosynthetic intermediates primarily occurs after deglutamylation. The transient expression of green fluorescent pro...Continue Reading

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Citations

Apr 19, 2017·Chemical Reviews·Kyle L DunbarChristian Hertweck
Apr 1, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yukihioro KoderaToshiaki Matsutomo
Jan 10, 2018·Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan·Kazuki Saito
Jul 24, 2018·The Plant Journal : for Cell and Molecular Biology·Michael Hartmann, Jürgen Zeier
Jun 20, 2019·The Plant Journal : for Cell and Molecular Biology·Jaya JoshiFrédéric Marsolais
Jun 1, 2017·Electrophoresis·María Molina-CalleMaría D Luque de Castro
Mar 1, 2018·Bioscience, Biotechnology, and Biochemistry·Yusuke AminoYutaka Ishiwatari
Jun 25, 2019·Journal of Experimental Botany·Jaya JoshiFrédéric Marsolais
Mar 13, 2018·Journal of the American College of Nutrition·Sedigheh AsgaryMahtab Keshvari
Mar 6, 2019·Annual Review of Plant Biology·Guangtao ZhuSanwen Huang
Sep 26, 2020·PeerJ·Kiran KhandagaleAshutosh Rai
Jun 13, 2020·The Journal of Biological Chemistry·Hannah ValentinoPablo Sobrado
Mar 7, 2017·Evidence-based Complementary and Alternative Medicine : ECAM·Yawen ZengShuming Yang
Sep 13, 2020·Communications Biology·Sara ThodbergElizabeth Heather Jakobsen Neilson
Mar 3, 2018·Journal of Agricultural and Food Chemistry·Masashi NakamotoYukihiro Kodera

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