Regioselective and stereospecific hydroxylation of GR24 by Sorghum bicolor and evaluation of germination inducing activities of hydroxylated GR24 stereoisomers toward seeds of Striga species

Bioorganic & Medicinal Chemistry
Kotomi UenoYukihiro Sugimoto

Abstract

Bioconversion of GR24, the most widely used synthetic strigolactone (SL), by hydroponically grown sorghum (Sorghum bicolor) and biological activities of hydroxylated GR24 stereoisomers were studied. Analysis of extracts and exudates of sorghum roots previously fed with a racemic and diastereomeric mixture of GR24, using liquid chromatography-tandem mass spectrometry with multiple reaction monitoring (MRM), confirmed uptake of GR24 and suggested its conversion to mono-hydroxylated products. Two major GR24 metabolites, 7-hydroxy-GR24 and 8-hydroxy-GR24, were identified in the root extracts and exudates by direct comparison of chromatographic behavior with a series of synthetic mono-hydroxylated GR24 analogues. Separate feeding experiments with each of the GR24 stereoisomers revealed that the hydroxylated products were derived from 2'-epi-GR24, an evidence of sterical recognition of the GR24 molecule by sorghum. Trans-4-hydroxy-GR24 isomers derived from all GR24 stereoisomers were detected in the exudates as minor metabolites. The synthetic hydroxy-GR24 isomers induced germination of Striga hermonthica in decreasing order of C-8>C-7>C-6>C-5>C-4. In contrast the stereoisomers having the same configuration of orobanchol, irrespectiv...Continue Reading

References

Nov 8, 2007·Bioscience, Biotechnology, and Biochemistry·Yuki KondoMitsuru Sasaki
Feb 18, 2009·Pest Management Science·Binne ZwanenburgDivakaramenon Sethumadhavan
Apr 27, 2010·Plant & Cell Physiology·Kohki AkiyamaHideo Hayashi
Nov 26, 2010·Chemistry : a European Journal·Victor X ChenJean-Marie Beau
Feb 16, 2011·Organic & Biomolecular Chemistry·Heetika MalikBinne Zwanenburg
Aug 9, 2011·Journal of Agricultural and Food Chemistry·Kotomi UenoYukihiro Sugimoto
Mar 17, 2012·Science·Adrian AlderSalim Al-Babili
Nov 28, 2012·Trends in Plant Science·Carolien Ruyter-SpiraHarro Bouwmeester
Dec 4, 2012·Molecular Plant·Binne Zwanenburg, Tomás Pospísil
Apr 20, 2013·Phytochemistry·Noriko MotonamiYukihiro Sugimoto
Jan 18, 2014·Proceedings of the National Academy of Sciences of the United States of America·Yoshiya SetoShinjiro Yamaguchi
Oct 27, 2014·Nature Chemical Biology·Yanxia ZhangHarro J Bouwmeester

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Citations

Jul 19, 2019·Pest Management Science·Daniel Blanco-AniaBinne Zwanenburg
Oct 27, 2018·Journal of Pesticide Science·Kotomi UenoYukihiro Sugimoto
Jul 17, 2018·Bioorganic & Medicinal Chemistry·Misa YamauchiYukihiro Sugimoto

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