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Developmental regulation of sterol biosynthesis inZea mays

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Lipids

Abstract

Sixty-one sterols and pentacyclic triterpenes have been isolated and characterized by chromatographic and spectral methods fromZea mays (corn). Several plant parts were examined; seed, pollen, cultured hypocotyl cells, roots, coleoptiles (sheaths), and blades. By studying reaction pathways and mechanisms on plants fed radiotracers ([2-14C]mevalonic acid, [2-14C]acetate, and [2-3H]acetate), and stable isotopes (D2O), we discovered that hydroxymethylglutaryl CoA reductase is not “the” rate-limiting enzyme of sitosterol production. Additionally, we observed an ontogenetic shift and kinetic isotope effect in sterol biosynthesis that was associated with the C-24 alkylation of the sterol side chain. Blades synthesized mainly 24α-ethyl-sterols, sheaths synthesized mainly 24-methyl-sterols, pollen possessed an interrupted sterol pathway, accumulating 24(28)-methylene-sterols, and germinating seeds were found to lack an activede novo pathway. Shoots, normally synthesizing (Z)-24(28)-ethylidine-cholesterol, after incubation with deuterated water, synthesized the rearranged double-bond isomer, stigmasta-5,23-dien-3β-ol. Examination of the mass spectrum and1H nuclear magnetic resonance spectrum of the deuterated 24-ethyl-sterol indicated the Bloch-Cornforth route originating with acetyl-CoA and passing through mevalonic acid to sterol was not operative at this stage of development. An alternate pathway giving rise to sterols is proposed.

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Abbreviations

DBED:

N,N′-dibenzylethylenediammonium

GLC:

gas-liquid chromatography

HMG-CoA:

hydroxymethylglutaryl CoA

HPLC:

high-performance liquid chromatography

KIE:

kinetic isotope effect

MS:

mass spectrometry

NMR:

nuclear magnetic resonance spectroscopy

RRTc :

relative retention time, relative to cholesterol

SAM:

S-adenosyl-l-methionine

TLC:

thin-layer chromatography

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Author information

Author notes

  1. De-an Guo (Visiting Professor)

    Present address: Department of Pharmacognosy, Beijing Medical University, 100083, Beijing, China

Authors and Affiliations

  1. Department of Chemistry and Biochemistry, Texas Tech University, P.O. Box 4260, 79409, Lubbock, Texas

    De-an Guo (Visiting Professor), M. Venkatramesh & W. David Nes

Authors
  1. De-an Guo
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  2. M. Venkatramesh
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  3. W. David Nes
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Additional information

Dedicated to the distinguished insect steroid biochemist Dr. James A. Svoboda on occasion of his sixtieth birthday.

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Guo, Da., Venkatramesh, M. & Nes, W.D. Developmental regulation of sterol biosynthesis inZea mays . Lipids 30, 203–219 (1995). https://doi.org/10.1007/BF02537823

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  • DOI: https://doi.org/10.1007/BF02537823

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