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Literature summary for 4.2.1.B6 extracted from

  • Hamberg, M.
    Biosynthesis of new divinyl ether oxylipins in Ranunculus plants (2002), Lipids, 37, 427-433.
    View publication on PubMed
Search for more literature for 4.2.1.B6

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate Ranunculus lingua 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 + (9Z,11Z)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O (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) ?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate Ranunculus peltatus 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 + (9Z,11Z)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O (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) ?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate Ranunculus lingua
-
 (9Z,11Z)-12-[(1E,3Z)-hexa-1,3-dien-1-yloxy]dodeca-9,11-dienoic acid + H2O i.e. (11Z)-etherolenic acid ?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate Ranunculus peltatus
-
 (9Z,11Z)-12-[(1E,3Z)-hexa-1,3-dien-1-yloxy]dodeca-9,11-dienoic acid + H2O i.e. (11Z)-etherolenic acid ?

Organism

Organism UniProt Comment Textmining
Ranunculus lingua
-
-
-
Ranunculus peltatus
-
-
-

Reaction

Reaction Comment Organism Reaction ID
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 Ranunculus lingua
a
(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 Ranunculus lingua
a

Source Tissue

Source Tissue Comment Organism Textmining
leaf
-
 Ranunculus lingua
-
leaf
-
 Ranunculus peltatus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
-
 Ranunculus peltatus (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)-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 ?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
-
 Ranunculus lingua (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)-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 ?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate a two-step pathway involving 13-lipoxygenase and divinyl ether synthase is responsible for biosynthesis of divinyl ethers in the plant Ranunculus lingua (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)-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) ?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate a two-step pathway involving 13-lipoxygenase and divinyl ether synthase is responsible for biosynthesis of divinyl ethers in the plant Ranunculus peltatus (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)-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) ?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate
-
 Ranunculus lingua (9Z,11Z)-12-[(1E,3Z)-hexa-1,3-dien-1-yloxy]dodeca-9,11-dienoic acid + H2O i.e. (11Z)-etherolenic acid ?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate
-
 Ranunculus peltatus (9Z,11Z)-12-[(1E,3Z)-hexa-1,3-dien-1-yloxy]dodeca-9,11-dienoic acid + H2O i.e. (11Z)-etherolenic acid ?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate
-
 Ranunculus lingua (9Z,11Z)-12-[(1E,3Z)-hexa-1,3-dien-1-yloxy]dodeca-9,11-dienoic acid + H2O i.e. (11Z)-etherolenic acid is the main product ?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate
-
 Ranunculus peltatus (9Z,11Z)-12-[(1E,3Z)-hexa-1,3-dien-1-yloxy]dodeca-9,11-dienoic acid + H2O i.e. (11Z)-etherolenic acid is the main product ?
additional information (9S,10E,12Z,15Z)-9-hydroperoxy-19,12,15-octadecatrienoate is not converted into divinyl ethers, reaction with leaf homogenate Ranunculus lingua ?
-
 ?
additional information (9S,10E,12Z,15Z)-9-hydroperoxy-19,12,15-octadecatrienoate is not converted into divinyl ethers, reaction with leaf homogenate Ranunculus peltatus ?
-
 ?