title: Regioselective and stereospecific hydroxylation of GR24 by Sorghum bicolor and evaluation of germination inducing activities of hydroxylated GR24 stereoisomers toward seeds of Striga species.
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, irrespective of position of hydroxylation, induced germination of Striga gesnerioides. The results confirm previous reports on structural requirements of SLs and ascribe a critical role to hydroxylation, but not to the position of the hydroxyl group in the AB part of the molecule, in induction of S. gesnerioides seed germination.
authors: Graduate School of Agricultural Science, Kobe University, Nada, Kobe 657-8501, Japan.
authors: Kotomi
authors: K
authors: Ueno
authors: Graduate School of Agricultural Science, Kobe University, Nada, Kobe 657-8501, Japan.
authors: Shunsuke
authors: S
authors: Ishiwa
authors: Graduate School of Agricultural Science, Kobe University, Nada, Kobe 657-8501, Japan.
authors: Hitomi
authors: H
authors: Nakashima
authors: Graduate School of Agricultural Science, Kobe University, Nada, Kobe 657-8501, Japan.
authors: Masaharu
authors: M
authors: Mizutani
authors: Graduate School of Agricultural Science, Kobe University, Nada, Kobe 657-8501, Japan.
authors: Hirosato
authors: H
authors: Takikawa
authors: Graduate School of Agricultural Science, Kobe University, Nada, Kobe 657-8501, Japan. Electronic address: yukihiro@kobe-u.ac.jp.
authors: Yukihiro
authors: Y
authors: Sugimoto
mesh_terms: D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D018525:Germination / Q000187:drug effects; D006900:Hydroxylation; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013058:Mass Spectrometry; D018517:Plant Roots / Q000737:chemistry / Q000378:metabolism; D012639:Seeds / Q000254:growth & development / Q000378:metabolism; D045868:Sorghum / Q000737:chemistry* / Q000378:metabolism; D013237:Stereoisomerism; D034362:Striga / Q000254:growth & development / Q000378:metabolism
chemical_list: C507382:GR24 compound; D007783:Lactones
keywords: GR24; Germination; Hydroxylation; Sorghum; Striga; Strigolactone