EST analysis of hop glandular trichomes identifies an O-methyltransferase that catalyzes the biosynthesis of xanthohumol

被引:161
作者
Nagel, Jana [1 ,2 ]
Culley, Lana K. [1 ]
Lu, Yuping [1 ]
Liu, Enwu [1 ]
Matthews, Paul D. [3 ]
Stevens, Jan F. [4 ,5 ]
Page, Jonathan E. [1 ]
机构
[1] Natl Res Council Canada, Inst Plant Biotechnol, Saskatoon, SK S7N 0W9, Canada
[2] Leibniz Inst Plant Biochem, D-06120 Halle, Germany
[3] SS Steiner, Hopsteiner, New York, NY 10065 USA
[4] Oregon State Univ, Dept Pharmaceut Sci, Corvallis, OR 97331 USA
[5] Oregon State Univ, Linus Pauling Inst, Corvallis, OR 97331 USA
关键词
D O I
10.1105/tpc.107.055178
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The glandular trichomes (lupulin glands) of hop (Humulus lupulus) synthesize essential oils and terpenophenolic resins, including the bioactive prenylflavonoid xanthohumol. To dissect the biosynthetic processes occurring in lupulin glands, we sequenced 10,581 ESTs from four trichome-derived cDNA libraries. ESTs representing enzymes of terpenoid biosynthesis, including all of the steps of the methyl 4-erythritol phosphate pathway, were abundant in the EST data set, as were ESTs for the known type III polyketide synthases of bitter acid and xanthohumol biosynthesis. The xanthohumol biosynthetic pathway involves a key O-methylation step. Four S-adenosyl-L-methionine-dependent O-methyltransferases (OMTs) with similarity to known flavonoid-methylating enzymes were present in the EST data set. OMT1, which was the most highly expressed OMT based on EST abundance and RT-PCR analysis, performs the final reaction in xanthohumol biosynthesis by methylating desmethylxanthohumol to form xanthohumol. OMT2 accepted a broad range of substrates, including desmethylxanthohumol, but did not form xanthohumol. Mass spectrometry and proton nuclear magnetic resonance analysis showed it methylated xanthohumol to 4-O-methylxanthohumol, which is not known from hop. OMT3 was inactive with all substrates tested. The lupulin gland-specific EST data set expands the genomic resources for H. lupulus and provides further insight into the metabolic specialization of glandular trichomes.
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页码:186 / 200
页数:15
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