Detection of a Pathway From Linoleate to a Novel Cyclopentenone: cis‐12‐Oxo‐10‐Phytoenoic Acid in Sunflower Roots

@article{Grechkin2007DetectionOA,
  title={Detection of a Pathway From Linoleate to a Novel Cyclopentenone: cis‐12‐Oxo‐10‐Phytoenoic Acid in Sunflower Roots},
  author={Alexander N Grechkin and Anna V. Ogorodnikova and Oleg I. Gnezdilov and Lucia S. Mukhtarova},
  journal={ChemBioChem},
  year={2007},
  volume={8}
}
The lipoxygenase pathway in sunflower roots was studied in vitro. A preliminary incubation of linoleic acid with 15 000 g supernatant of homogenate of sunflower roots (1.5–6 days after germination) revealed the predominant activity of 13‐lipoxygenase. The exogenously added linoleic acid 13‐hydroperoxide is further utilized through two competing pathways. One of them is directed towards formation of the ketodiene (9Z,11E)‐13‐oxooctadeca‐9,11‐dienoic acid. The second pathway, which is controlled… 
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Background Citations
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Methods Citations
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14 Citations

Novel Allene Oxide Synthase Products Formed via Favorskii‐Type Rearrangement: Mechanistic Implications for 12‐Oxo‐10,15‐phytodienoic Acid Biosynthesis

In vitro incubations of AOSs with α‐linolenic acid 13(S)‐hydroperoxide reliably afforded 1 along with 12‐oxo‐PDA and α‐ketol demonstrated that cyclopropanones are short‐lived AOS products along with allene oxides.

Tomato CYP74C3 is a Multifunctional Enzyme not only Synthesizing Allene Oxide but also Catalyzing its Hydrolysis and Cyclization

The results indicate that in contrast to the ordinary allene oxide synthases, LeAOS3 (CYP74C subfamily) is a multifunctional enzyme, catalyzing not only the synthesis, but also the hydrolysis and cyclization of allenes oxide.

Allene Oxide Synthase Pathway in Cereal Roots: Detection of Novel Oxylipin Graminoxins

Young roots of wheat, barley, and sorghum, as well as methyl jasmonate pretreated rice seedlings, undergo an unprecedented allene oxide synthase pathway targeted to previously unknown oxylipins 1–3, indicating that conversion of the allenes oxide into the cyclopropanone is controlled by soluble cyclase.

Stereospecific biosynthesis of (9S,13S)-10-oxo-phytoenoic acid in young maize roots.

Thermal conversions of fatty acid peroxides to cyclopentenones: a biomimetic model for allene oxide synthase pathway.

A lipoxygenase-divinyl ether synthase pathway in flax (Linum usitatissimum L.) leaves.

Biosynthesis of Jasmonates from Linoleic Acid by the Fungus Fusarium oxysporum. Evidence for a Novel Allene Oxide Cyclase.

The presence of AOS and the biosynthesis of the allene oxide 12,13(S)-epoxy-9,11-octadecadienoic acid confirms the conclusion that the fungal AOC is distinct from the corresponding plant enzyme.

Hydroperoxide lyase cascade in pea seedlings: Non-volatile oxylipins and their age and stress dependent alterations.

Detection of divinyl ether synthase in Lily-of-the-Valley (Convallaria majalis) roots.

Impact of Cr(VI) on the oxidation of polyunsaturated fatty acids in Helianthus annuus roots studied by metabolomic tools.

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