Characterization of Cyclopropane Fatty-acid Synthase fromSterculia foetida

Bao, Xinhe; Thelen, Jay J.; Bonaventure, Gustavo; Ohlrogge, John B.

doi:10.1074/jbc.m212464200

Cited by 50 publications

(46 citation statements)

References 40 publications

(23 reference statements)

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“…The 438-aa Nterminal domain of SfCPA-FAS contained a hypothetical flavin-binding site (GXGXGXXXA) and was most similar to Arabidopsis tryptophan 2-monoxygenase; the function of this domain has not been determined. In Mycobacterium tuberculosis and Agrobacterium tumefaciens, related flavin-binding proteins appear to be encoded 200 and 802-nt, respectively, upstream of the cyclopropyl fatty acid synthase genes [73]. The SfCPA-FAS activity was localized to the S. foetida seed microsomal pellet and, with this membrane fraction, S-[ 14 CH 3 ]methionine and [1-14 C]oleic acid were shown to be substrates [64,73].…”

Section: Steariolic and Tariricmentioning

confidence: 98%

“…In Mycobacterium tuberculosis and Agrobacterium tumefaciens, related flavin-binding proteins appear to be encoded 200 and 802-nt, respectively, upstream of the cyclopropyl fatty acid synthase genes [73]. The SfCPA-FAS activity was localized to the S. foetida seed microsomal pellet and, with this membrane fraction, S-[ 14 CH 3 ]methionine and [1-14 C]oleic acid were shown to be substrates [64,73]. The product 5N was almost exclusively found in the PC fraction of microsomal assays, and in a subsequent investigation, it was shown the oleoyl groups in the sn-1 position of PC are likely the direct substrate for cyclopropane formation, a position unprecedented for ER-localized lipid modification reactions in plants [73].…”

Section: Steariolic and Tariricmentioning

confidence: 99%

“…The timing of chain shortening, presumably by α-oxidation, was not determined but free fatty acids were the proposed substrate. Bao and coworkers isolated the cyclopropyl fatty acid synthase (SfCPA-FAS) from S. foetida using an EST screening approach, where 0.4% of the sequenced plasmids from a library of developing S. foetida seed DNA contained a gene related to bacterial cyclopropyl fatty acid synthase [64,73]. The carboxy-terminal portion of the 864-aa SfCPA-FAS showed 32% identity (122 of 376 residues) with the bacterial synthase.…”

Section: Steariolic and Tariricmentioning

confidence: 99%

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Biosynthesis and function of polyacetylenes and allied natural products

Minto

Blacklock

2008

Progress in Lipid Research

291

228

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Polyacetylenic natural products are a substantial class of often unstable compounds containing a unique carbon-carbon triple bond functionality, that are intriguing for their wide variety of biochemical and ecological functions, economic potential, and surprising mode of biosynthesis. Isotopic tracer experiments between 1960 and 1990 demonstrated that the majority of these compounds are derived from fatty acid and polyketide precursors. During the past decade, research into the metabolism of polyacetylenes has swiftly advanced, driven by the cloning of the first genes responsible for polyacetylene biosynthesis in plants, moss, fungi, and actinomycetes, and the initial characterization of the gene products.The current state of knowledge of the biochemistry and molecular genetics of polyacetylenic secondary metabolic pathways will be presented together with an up-to-date survey of new terrestrial and marine natural products, their known biological activities, and a discussion of their likely metabolic origins.

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Section: Steariolic and Tariricmentioning

confidence: 98%

Section: Steariolic and Tariricmentioning

confidence: 99%

Section: Steariolic and Tariricmentioning

confidence: 99%

See 1 more Smart Citation

Biosynthesis and function of polyacetylenes and allied natural products

Minto

Blacklock

2008

Progress in Lipid Research

291

228

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“…DHSA has been identified in trypanosomatid protozoa and CFA synthase activity has been demonstrated (Li et al 1993). DHSA synthesis from oleoyl phospatidylcholines has recently also been observed in tobacco cells after transformation of a gene from the plant Sterculia foetida (Bao et al 2003). DHSA and cis-9,10-methyleneheptadecanoic acid occur in roots of S. foetida (Kaimal and Lakshminarayana, 1970).…”

mentioning

confidence: 99%

An Essential Gene for Fruiting Body Initiation in the Basidiomycete Coprinopsis cinerea Is Homologous to Bacterial Cyclopropane Fatty Acid Synthase Genes

et al. 2006

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The self-compatible Coprinopsis cinerea homokaryon AmutBmut produces fruiting bodies without prior mating to another strain. Early stages of fruiting body development include the dark-dependent formation of primary hyphal knots and their light-induced transition to the more compact secondary hyphal knots. The AmutBmut UV mutant 6-031 forms primary hyphal knots, but development arrests at the transition state by a recessive defect in the cfs1 gene, isolated from a cosmid library by mutant complementation. A normal primordia phenotype was achieved when cfs11 was embedded at both sides in at least 4.0 kb of native flanking DNA. Truncations of the flanking DNA lead to reduction in transformation frequencies and faults in primordia tissue formation, suggesting that the gene is also acting at later stages of development. The cfs1 gene encodes a protein highly similar to cyclopropane fatty acid synthases, a class of enzymes shown in prokaryotes and recently in a plant to convert membrane-bound unsaturated fatty acids into cyclopropane fatty acids. In C. cinerea 6-031, the mutant cfs1 allele carries a T-to-G transversion, leading to an amino acid substitution (Y441D) in a domain suggested to be involved in the catalytic function of the protein and/or membrane interaction.

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“…In plants, SAM is also converted to 1-aminocyclopropane-1-carboxylic acid, the direct precursor of the plant hormone ethylene (Kevin et al, 2002). SAM also provides the methylene group used in the biogenesis of cyclopropane fatty acids that accumulate in many types of seeds (Bao et al, 2002(Bao et al, , 2003.…”

Section: Introductionmentioning

confidence: 99%

ArabidopsisSAMT1 Defines a Plastid Transporter Regulating Plastid Biogenesis and Plant Development

et al. 2006

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S-Adenosylmethionine (SAM) is formed exclusively in the cytosol but plays a major role in plastids; SAM can either act as a methyl donor for the biogenesis of small molecules such as prenyllipids and macromolecules or as a regulator of the synthesis of aspartate-derived amino acids. Because the biosynthesis of SAM is restricted to the cytosol, plastids require a SAM importer. However, this transporter has not yet been identified. Here, we report the molecular and functional characterization of an Arabidopsis thaliana gene designated SAM TRANSPORTER1 (SAMT1), which encodes a plastid metabolite transporter required for the import of SAM from the cytosol. Recombinant SAMT1 produced in yeast cells, when reconstituted into liposomes, mediated the counter-exchange of SAM with SAM and with S-adenosylhomocysteine, the by-product and inhibitor of transmethylation reactions using SAM. Insertional mutation in SAMT1 and virus-induced gene silencing of SAMT1 in Nicotiana benthamiana caused severe growth retardation in mutant plants. Impaired function of SAMT1 led to decreased accumulation of prenyllipids and mainly affected the chlorophyll pathway. Biochemical analysis suggests that the latter effect represents one prominent example of the multiple events triggered by undermethylation, when there is decreased SAM flux into plastids.

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Characterization of Cyclopropane Fatty-acid Synthase fromSterculia foetida

Abstract: Cyclopropane synthase from Sterculia foetida developing seeds catalyzes the addition of a methylene group from S-adenosylmethionine to the cis double bond of oleic acid (Bao, X., Katz, S., Pollard, M., and Ohlrogge, J.

Cited by 50 publications

References 40 publications

Biosynthesis and function of polyacetylenes and allied natural products

Biosynthesis and function of polyacetylenes and allied natural products

An Essential Gene for Fruiting Body Initiation in the Basidiomycete Coprinopsis cinerea Is Homologous to Bacterial Cyclopropane Fatty Acid Synthase Genes

ArabidopsisSAMT1 Defines a Plastid Transporter Regulating Plastid Biogenesis and Plant Development

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