n-Hexanal and (Z)-3-hexenal are generated from arachidonic acid and linolenic acid by a lipoxygenase in Marchantia polymorpha L.
Most terrestrial plants form green leaf volatiles (GLVs), which are mainly composed of six-carbon (C6) compounds. In our effort to study the distribution of the ability of lipoxygenase (LOX) to form GLVs, we found that a liverwort, Marchantia polymorpha, formed n-hexanal and (Z)-3-hexenal. Some LOXs execute a secondary reaction to form short chain volatiles. One of the LOXs from M. polymorpha (MpLOX7) oxygenized arachidonic and α-linolenic acids at almost equivalent efficiency and formed C6-aldehydes during its catalysis; these are likely formed from hydroperoxides of arachidonic and α-linolenic acids, with a cleavage of the bond between carbon at the base of the hydroperoxy group and carbon of double bond, which is energetically unfavorable. These lines of evidence suggest that one of the LOXs in liverwort employs an unprecedented reaction to form C6 aldehydes as by-products of its reaction with fatty acid substrates.
a Graduate School of Medicine (Agriculture) , Yamaguchi University , Yamaguchi , Japan.|d Faculty of Science, Botany Department , Port Said University , Port Said , Egypt.
Moataz M
MM
Tawfik
b Department of Biology-Oriented Science and Technology , Kinki University , Osaka , Japan.
Katsuyuki T
KT
Yamato
c Graduate School of Biostudies , Kyoto University , Kyoto , Japan.
Takayuki
T
Kohchi
e Department of Biological Chemistry, Graduate School of Sciences and Technology for Innovation , Yamaguchi University , Yamaguchi , Japan.
Takao
T
Koeduka
a Graduate School of Medicine (Agriculture) , Yamaguchi University , Yamaguchi , Japan.|e Department of Biological Chemistry, Graduate School of Sciences and Technology for Innovation , Yamaguchi University , Yamaguchi , Japan.
Kenji
K
Matsui
D000447:Aldehydes / Q000378:metabolism*; D000595:Amino Acid Sequence; D016718:Arachidonic Acid / Q000378:metabolism*; D055162:Biocatalysis; D003001:Cloning, Molecular; D057075:Enzyme Assays; D004926:Escherichia coli / Q000235:genetics / Q000378:metabolism; D015870:Gene Expression; D007700:Kinetics; D008054:Lipid Peroxides / Q000378:metabolism; D008084:Lipoxygenase / Q000235:genetics / Q000378:metabolism*; D047008:Marchantia / Q000737:chemistry / Q000145:classification / Q000378:metabolism*; D010802:Phylogeny; D018515:Plant Leaves / Q000737:chemistry / Q000378:metabolism; D010940:Plant Proteins / Q000235:genetics / Q000378:metabolism*; D011994:Recombinant Proteins / Q000235:genetics / Q000378:metabolism; D064210:Secondary Metabolism; D016415:Sequence Alignment; D013816:Thermodynamics; D017962:alpha-Linolenic Acid / Q000378:metabolism*
D000447:Aldehydes; D008054:Lipid Peroxides; D010940:Plant Proteins; D011994:Recombinant Proteins; D017962:alpha-Linolenic Acid; D016718:Arachidonic Acid; C586688:3-hexenal; C010463:n-hexanal; D008084:Lipoxygenase
green leaf volatiles; lipoxygenase; liverworts