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2 (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate = (9Z,11E)-12-[(1Z)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + (9Z,11Z)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + 2 H2O
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate = (9Z,11Z)-12-[(1E,3Z)-hexa-1,3-dien-1-yloxy]dodeca-9,11-dienoic acid
2 (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate = (9Z,11E)-12-[(1Z)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + (9Z,11Z)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + 2 H2O
the conversion of 13-hydroperoxides into (11Z)-etheroleic and (11Z)-etherolenic acids by divinyl ether synthase is remarkable in the sense that it involves a thermodynamically unfavorable E/Z isomerization of the DELTA11 double bond
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2 (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate = (9Z,11E)-12-[(1Z)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + (9Z,11Z)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + 2 H2O
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(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate = (9Z,11Z)-12-[(1E,3Z)-hexa-1,3-dien-1-yloxy]dodeca-9,11-dienoic acid
the conversion of 13-hydroperoxides into (11Z)-etheroleic and (11Z)-etherolenic acids by divinyl ether synthase is remarkable in the sense that it involves a thermodynamically unfavorable E/Z isomerization of the DELTA11 double bond
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(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate = (9Z,11Z)-12-[(1E,3Z)-hexa-1,3-dien-1-yloxy]dodeca-9,11-dienoic acid
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(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
(9Z,11E)-12-[(1Z)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + (9Z,11Z)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
(9Z,11Z)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
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an essentially complete loss of isotope is noted with the (14R)-deuterated precursor, whereas incubation of the 14(S)-deuterated precursor affords products that retained most of the deuterium label
i.e. (11Z)-etheroleic acid, reaction with leaf homogenate
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(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
(9Z,11E)-12[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
i.e. 13-HPOD
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(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate
(9Z,11Z)-12-[(1E,3Z)-hexa-1,3-dien-1-yloxy]dodeca-9,11-dienoic acid + H2O
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
(9Z,11E)-12[(1Z,3Z)-hexa-1,3-dien-1-yloxy]dodeca-9,11-dienoic acid + H2O
i.e. 13-HPOT
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additional information
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(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
(9Z,11E)-12-[(1Z)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + (9Z,11Z)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
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(9Z,11E)-12-[(1Z)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid (i.e. omega5(Z)-etheroleic acid) and (9Z,11Z)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid (11Z-etheroleic acid) are formed in proportions 40:60, reaction with leaf homogenate
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(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
(9Z,11E)-12-[(1Z)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + (9Z,11Z)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
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a two-step pathway involving 13-lipoxygenase and divinyl ether synthase is responsible for biosynthesis of divinyl ethers in the plant
(9Z,11E)-12-[(1Z)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid (i.e. omega5(Z)-etheroleic acid) and (9Z,11Z)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid (11Z-etheroleic acid)
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(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
(9Z,11E)-12-[(1Z)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + (9Z,11Z)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
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(9Z,11E)-12-[(1Z)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid (i.e. omega5(Z)-etheroleic acid) and (9Z,11Z)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid ((11Z)-etheroleic acid) are formed in proportions 40:60, reaction with leaf homogenate
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(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
(9Z,11E)-12-[(1Z)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + (9Z,11Z)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
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a two-step pathway involving 13-lipoxygenase and divinyl ether synthase is responsible for biosynthesis of divinyl ethers in the plant
(9Z,11E)-12-[(1Z)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid (i.e. omega5(Z)-etheroleic acid) and (9Z,11Z)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid (11Z-etheroleic acid)
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(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate
(9Z,11Z)-12-[(1E,3Z)-hexa-1,3-dien-1-yloxy]dodeca-9,11-dienoic acid + H2O
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i.e. (11Z)-etherolenic acid, i.e. (11Z)-etherolenic acid is the main product
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(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate
(9Z,11Z)-12-[(1E,3Z)-hexa-1,3-dien-1-yloxy]dodeca-9,11-dienoic acid + H2O
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i.e. (11Z)-etherolenic acid, i.e. (11Z)-etherolenic acid is the main product
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additional information
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(9S,10E,12Z,15Z)-9-hydroperoxy-19,12,15-octadecatrienoate is not converted into divinyl ethers, reaction with leaf homogenate
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additional information
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(9S,10E,12Z,15Z)-9-hydroperoxy-19,12,15-octadecatrienoate is not converted into divinyl ethers, reaction with leaf homogenate
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additional information
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products are analyzed by gas chromatography-mass spectrometry, Individual oxylipins are purified by HPLC and finally identified by their NMR data, including the 1H NMR, 2D-COSY, HSQC and HMBC, overview. Enzyme CYP74M1 (SmDES1) specifically converts 13-HPOT to (11Z)-etherolenic acid and 13-HPOD to (11Z)-etheroleic acid via a (Z)-vinyl ether radial intermediate. The enzyme is inactive towards (9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid (9-HPOT) and (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid (9-HPOD)
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additional information
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products are analyzed by gas chromatography-mass spectrometry, Individual oxylipins are purified by HPLC and finally identified by their NMR data, including the 1H NMR, 2D-COSY, HSQC and HMBC, overview. Enzyme CYP74M1 (SmDES1) specifically converts 13-HPOT to (11Z)-etherolenic acid and 13-HPOD to (11Z)-etheroleic acid via a (Z)-vinyl ether radial intermediate. The enzyme is inactive towards (9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid (9-HPOT) and (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid (9-HPOD)
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(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
(9Z,11E)-12-[(1Z)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + (9Z,11Z)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
(9Z,11E)-12[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
i.e. 13-HPOD
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(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate
(9Z,11Z)-12-[(1E,3Z)-hexa-1,3-dien-1-yloxy]dodeca-9,11-dienoic acid + H2O
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
(9Z,11E)-12[(1Z,3Z)-hexa-1,3-dien-1-yloxy]dodeca-9,11-dienoic acid + H2O
i.e. 13-HPOT
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(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
(9Z,11E)-12-[(1Z)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + (9Z,11Z)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
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a two-step pathway involving 13-lipoxygenase and divinyl ether synthase is responsible for biosynthesis of divinyl ethers in the plant
(9Z,11E)-12-[(1Z)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid (i.e. omega5(Z)-etheroleic acid) and (9Z,11Z)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid (11Z-etheroleic acid)
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(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
(9Z,11E)-12-[(1Z)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + (9Z,11Z)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
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a two-step pathway involving 13-lipoxygenase and divinyl ether synthase is responsible for biosynthesis of divinyl ethers in the plant
(9Z,11E)-12-[(1Z)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid (i.e. omega5(Z)-etheroleic acid) and (9Z,11Z)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid (11Z-etheroleic acid)
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(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate
(9Z,11Z)-12-[(1E,3Z)-hexa-1,3-dien-1-yloxy]dodeca-9,11-dienoic acid + H2O
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i.e. (11Z)-etherolenic acid
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(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate
(9Z,11Z)-12-[(1E,3Z)-hexa-1,3-dien-1-yloxy]dodeca-9,11-dienoic acid + H2O
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i.e. (11Z)-etherolenic acid
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4.2.1.B6 (11Z)-etheroleic acid synthase
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