Developmental regulation of sterol biosynthesis in Zea mays
Abstract
Sixty-one sterols and pentacyclic triterpenes have been isolated and characterized by chromatographic and spectral methods from Zea 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-(14)C]mevalonic acid, [2-(14)C]acetate, and [2-(3)H]acetate), and stable isotopes (D2O), we discovered that hydroxymethylgutaryl 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 24 alpha-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 active de 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-3 beta-ol. Examination of the mass spectrum and 1H 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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Invertebrates cannot synthesize ECs; rather, they consume phytosterols and convert them into ECs.
“Additionally, invertebrates cannot synthesize ECs; rather, they consume phytosterols and convert them into ECs.”
From Phytoecdysteroids: Distribution, Structural Diversity, Biosynthesis, Activity, and Crosstalk with Phytohormones (2022) · cites this paper as [116]
Plants produce ECs via mevalonic acid (MVA) and cholesterol.
“On the other hand, plants produce ECs via mevalonic acid (MVA) and cholesterol [21,22,115,116].”
From Phytoecdysteroids: Distribution, Structural Diversity, Biosynthesis, Activity, and Crosstalk with Phytohormones (2022) · cites this paper as [116]
In corn, MVA is not the pathway for synthesizing phytosterols; other pathways participate in synthesizing IPP.
“In corn, MVA is not the pathway for synthesizing phytosterols; other pathways participate in synthesizing IPP [18,116,143,144].”
From Phytoecdysteroids: Distribution, Structural Diversity, Biosynthesis, Activity, and Crosstalk with Phytohormones (2022) · cites this paper as [116]
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“HE 20-hydroxyecdysone BR brassinosteroid CK cytokinin DMAPP dimethylallyl diphosphate EC ecdysteroid ET ethylene GA gibberellin HPLC high-performance column chromatography IPP isopentenyl diphosphate iPR isopentenyladenosine JA jasmonic acid MDA malondialdehyde MeJA methyl jasmonate MeOH methanol MEP 2C-methyl-erythri…”
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“The epimeric mixture of 24-methylcholesterol (24R, campesterol; 24S, 24-epi-campesterol) is ubiquitous, whereas 24-ethylsterols are exclusively (24R)-24-ethylsterols, such as sitosterol and stigmasterol (Nes et al., 1977; Guo et al., 1995; Schaller, 2003) (Figure S2) with the exception of a few plant genera that are a…”
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BackgroundSoybean sterol composition and utilization by Phytophthora sojae
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5 Sterol metabolism and functions in higher plants
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Enzymology of Phytosterol Transformations
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Organization and dynamics of functional plant membrane microdomains
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Overturning dogma: tolerance of insects to mixed-sterol diets is not universal
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“Determination of stigmasterol, b-sitosterol, and campesterol was used to characterize the DRMs from bean leaves and maize embryos because they are the most abundant sterols in these plant species [42,44–47].”
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Sterol specificity of theSaccharomyces cerevisiae ERG6 gene product expressed inEscherichia coli
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Terpenoid Esters Are the Major Constituents From Leaf Lipid Droplets of Camellia sinensis
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“Additionally, the synthesis of 24-ethyl-sterols (sitosterol and stigmasterol) is kinetically favored over 24-methyl-sterols (campesterol) at some stages of corn development (Guo et al., 1995), and, thus, the first sterols are the principal ones.”
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“Another study, in which 61 sterols and pentacyclinc triterpenes were characterized from Zea mays seedlings, reported the lack of active de novo synthesis in seedlings relative to other tissues (Guo et al., 1995).”
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“However, relevant to the understanding of sterol biosynthesis in Acanthamoeba for the purpose of inhibition, the phyla-specific canonical routes to alternate sterol products must also be considered, because different steps in sterol metabolism – sterol side chain or nucleus revisions-could interface uniquely through s…”
BackgroundMethodStereochemistry of Hydrogen Migration from C-24 to C-25 during Phytosterol Biomethylation
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Herbicide symptomology and the mechanism of action of methiozolin
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Membrane Sterol Composition in Arabidopsis thaliana Affects Root Elongation via Auxin Biosynthesis
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Three New Multiflorane-Type Triterpenes from Pumpkin (Cucurbita maxima) Seeds
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Metabolomic profiling of developing perilla leaves reveals the best harvest time
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Lipids in Fruits and Vegetables
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Evidence for multiple sterol methyl transferase pathways in Pneumocystis carinii
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Phytosterol biosynthesis pathway in Mortierella alpina
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Fatty acid profiles from the plasma membrane and detergent resistant membranes of two plant species
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Symmetric and Asymmetric Models for the Arabidopsis thaliana Plasma Membrane: A Simulation Study
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Druggable Sterol Metabolizing Enzymes in Infectious Diseases: Cell Targets to Therapeutic Leads
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Effects of impaired steryl ester biosynthesis on tomato growth and developmental processes
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- Authors
- Guo, D., Venkatramesh, M., & Nes, W. D.
- Affiliations
- Texas Tech University (US)
- Venue
- Lipids
- Publisher
- Wiley
- Published
- 1995-03
- Volume
- 30
- Issue
- 3
- Pages
- 203-19
- ISSN
- 0024-4201 (ISSN-L)
- 1558-9307
- OpenAlex
- W2035132561
- Cited by
- 130
- References
- 52
- Citations by year
- 2026: 3 · 2025: 1 · 2024: 3 · 2023: 2 · 2022: 4 · 2021: 3 · 2020: 3 · 2019: 9 · 2018: 4 · 2017: 5 · 2016: 4 · 2015: 4 · 2014: 1 · 2013: 4 · 2012: 6
- FWCI
- 2.48
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Lipids (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Plant biochemistry and biosynthesis
- Health Sciences › Medicine › Surgery › Cholesterol and Lipid Metabolism
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Lipid metabolism and biosynthesis
- Keywords
- sterol biosynthesis, maize, plant development, sitosterol, rate-limiting enzyme, kinetic isotope effects, heavy water, mevalonate pathway, pollen, seed germination, coleoptile, blades, roots
- MeSH terms
- Acetates, Alkylation, Carbon Radioisotopes, Chromatography, High Pressure Liquid, Zea mays, Hydroxymethylglutaryl CoA Reductases, Mevalonic Acid, Models, Biological, Oxidation-Reduction, Phytosterols, Seeds, Sitosterols, Mass Spectrometry, Tissue Distribution, Plant Roots, Plant Shoots
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