TY - JOUR
T1 - Characterization of 12-oxophytodienoic acid reductases from rose-scented geranium (pelargonium graveolens)
AU - Iijima, Miu
AU - Kenmoku, Hiromichi
AU - Takahashi, Hironobu
AU - Lee, Jung Bum
AU - Toyota, Masao
AU - Asakawa, Yoshinori
AU - Kurosaki, Fumiya
AU - Taura, Futoshi
PY - 2016/12
Y1 - 2016/12
N2 - Pelargonium graveolens L'Hér, also referred to as rose geranium, is a popular herbal plant with typical rosy fragrance largely based on the blend of monoterpenoid constituents. Among them, citronellol, which is biosynthesized from geraniol via double bond reduction, is the most abundant scent compound. In this study, three 12-oxophytodienoic acid reductases (PgOPR1-3) have been cloned from P. graveolens, as possible candidates for the double-bond reductase involved in citronellol biosynthesis. The bacterially expressed recombinant PgOPRs did not reduce geraniol to citronellol, but stereoselectively converted citral into (S)-citronellal in the presence of NADPH. Thus, the α,β-unsaturated carbonyl moiety in the substrate is essential for the catalytic activity of PgOPRs, as reported for OPRs from other plants and structurally related yeast old yellow enzymes. PgOPRs promiscuously accepted linear and cyclic α,β- unsaturated carbonyl substrates, including methacrolein, a typical reactive carbonyl compound. The possible biotechnological applications for PgOPRs in plant metabolic engineering, based on their catalytic properties, are discussed herein.
AB - Pelargonium graveolens L'Hér, also referred to as rose geranium, is a popular herbal plant with typical rosy fragrance largely based on the blend of monoterpenoid constituents. Among them, citronellol, which is biosynthesized from geraniol via double bond reduction, is the most abundant scent compound. In this study, three 12-oxophytodienoic acid reductases (PgOPR1-3) have been cloned from P. graveolens, as possible candidates for the double-bond reductase involved in citronellol biosynthesis. The bacterially expressed recombinant PgOPRs did not reduce geraniol to citronellol, but stereoselectively converted citral into (S)-citronellal in the presence of NADPH. Thus, the α,β-unsaturated carbonyl moiety in the substrate is essential for the catalytic activity of PgOPRs, as reported for OPRs from other plants and structurally related yeast old yellow enzymes. PgOPRs promiscuously accepted linear and cyclic α,β- unsaturated carbonyl substrates, including methacrolein, a typical reactive carbonyl compound. The possible biotechnological applications for PgOPRs in plant metabolic engineering, based on their catalytic properties, are discussed herein.
KW - 12-Oxophytodienoic acid reductase
KW - Monoterpene biosynthesis
KW - Pelargonium graveolens
KW - Reactive carbonyl species
KW - Substrate specificity
UR - http://www.scopus.com/inward/record.url?scp=85019107284&partnerID=8YFLogxK
U2 - 10.1177/1934578x1601101201
DO - 10.1177/1934578x1601101201
M3 - 学術論文
AN - SCOPUS:85019107284
SN - 1934-578X
VL - 11
SP - 1775
EP - 1782
JO - Natural Product Communications
JF - Natural Product Communications
IS - 12
ER -