PATHWAY: rn00902 Help
Entry Name Monoterpenoid biosynthesis
Description Monoterpenoids (C10 terpenoids) are a group of terpenoids consisting of two isoprene units. They are derived from geranyl diphosphate (GPP). Most monoterpenoids are volatile oils with highly distinctive aromas and flavors, such as essential oils, turpentine, and oleoresins of coniferous plants. This map shows some examples. The monoterpene ketone l-menthone is specifically converted to l-menthol and d-neomenthol in mature peppermint leaves. The iridoids constitute a family of highly oxygenated monoterpenes, mixtures of which are present in many medicinal plants, such as valerian. They are derived from geraniol or nerol via oxidation of a terminal methyl group. The cyclopentane ring of loganin can itself be cleaved in a further P450-dependent step, leading to secologanin, which provides the carbon skeleton for many powerfully bioactive secondary metabolites of indole alkaloids.
Class Metabolism; Metabolism of terpenoids and polyketides
Pathway map Other DBs Reaction R02004 geranyl-diphosphate diphosphate-lyase [cyclizing, (-)-endo-fenchol-forming]
R02006 geranyl-diphosphate diphosphate-lyase (cyclizing, sabinene-hydrate-forming)
R02007 (+)-bornyl-diphosphate lyase (decyclizing)
R02009 geranyldiphosphate diphosphate-lyase (myrcene-forming)
R02013 geranyl-diphosphate diphosphate-lyase [cyclizing; (4S)-limonene-forming]
R02177 (-)-menthol:NADP+ oxidoreductase
R02468 (S)-limonene,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (6-hydroxylating)
R02469 (S)-limonene,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3-hydroxylating)
R02470 (S)-limonene,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (7-hydroxylating)
R02548 (+)-neomenthol:NADP+ oxidoreductase
R02944 (+)-borneol:NAD+ oxidoreductase
R02994 6-endo-hydroxycineole:NAD+ 6-oxidoreductase
R02995 6-oxocineole,NADPH:oxygen oxidoreductase
R03114 (-)-trans-carveol:NADP+ oxidoreductase
R03261 (-)-trans-isopiperitenol:NAD+ oxidoreductase
R03554 S-adenosyl-L-methionine:loganate 11-O-methyltransferase
R03555 loganin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (ring-cleaving)
R03556 7-deoxyloganin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (7alpha-hydroxylating)
R05765 geranyl-diphosphate diphosphate-lyase [cyclizing, (-)-alpha-pinene-forming]
R05766 geranyl-diphosphate diphosphate-lyase [cyclizing, (-)-beta-pinene-forming]
R05832 7-deoxyloganate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (7alpha-hydroxylating)
R05833 loganate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (ring-cleaving)
R05834 S-adenosyl-L-methionine:secologanate 11-O-methyltransferase
R06117 (+)-trans-carveol: NAD+ oxidoreductase
R06119 (R)-limonene,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (6-hydroxylating)
R06120 geranyldiphosphate diphosphate lyase [(+)-(R)-limonene-forming]
R06417 (+)-cis-isopulegone:NADP+ oxidoreductase
R06418 (+)-cis-isopulegone isomerase
R06419 (-)-menthone:NADP+ oxidoreductase
R06421 geranyl-diphosphate diphosphate-lyase [cyclizing, (-)-alpha-terpineol-forming]
R07631 geranyl-diphosphate diphosphate-lyase [(3S)-linalool-forming]
R07632 geranyl-diphosphate diphosphate-lyase [(3R)-linalool-forming]
R08396 geranyl-diphosphate diphosphohydrolase
R08499 (6E)-8-hydroxygeraniol:NADP+ oxidoreductase
R08529 monoterpenyl-diphosphate pyrophosphohydrolase
R08784 1,8-cineole,[reduced flavodoxin]:oxygen oxidoreductase (2-endo-hydroxylating)
R08785 geraniol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (8-hydroxylating)
R08923 (+)-pulegone,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (9-hydroxylating)
R08925 (-)-menthone,NADPH:oxygen oxidoreductase
R09702 (+)-linalool hydro-lyase (myrcene-forming)
R09922 (+)-linalool,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (8-hydroxylating)
R09923 (-)-linalool,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (8-hydroxylating)
R09924 8-hydroxylinalool,[reduced NADPH---hemoprotein reductase]:oxygen 8-oxidoreductase
R09963 geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-car-3-ene-forming]
R09971 geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-camphene-forming]
R09972 geranyl-diphosphate diphosphate-lyase [cyclizing, (-)-camphene-forming]
R10834 UDP-alpha-D-glucose:7-deoxyloganetate O-D-glucosyltransferase
R10835 UDP-alpha-D-glucose:7-deoxyloganetin O-D-glucosyltransferase
R10918 (R)-ipsdienol:NAD+ oxidoreductase
R10919 (R)-ipsdienol:NADP+ oxidoreductase
R11055 myrcene,NADPH---hemoprotein reductase:O2 oxidoreductase (hydroxylating)
R11551 geranyl-diphosphate phosphohydrolase
R11552 geranyl-phosphate phosphohydrolase
R12182 iridotrial,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase
R12231 (+)-cis,trans-nepetalactol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase
R12253 7-deoxyloganetic alcohol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase
R12517 (S)-8-oxocitronellyl enol:NAD+ oxidoreductase
R12518 (S)-8-oxocitronellyl enol:NADP+ oxidoreductase
R12520 (S)-8-oxocitronellyl enol cyclase [(+)-cis,trans-nepetalactol-forming]
Compound C01123 (-)-trans-Isopiperitenol
C04718 1,6,6-Trimethyl-2,7-dioxabicyclo[3.2.2]nonan-3-one
C06066 4,5-Dihydro-5,5-dimethyl-4-(3-oxobutyl)furan-2(3H)-one
C11672 10-Deoxygeniposidic acid
C18027 (4R,7S)-7-Isopropyl-4-methyloxepan-2-one
C22014 7-Deoxyloganetic alcohol
C22225 (S)-8-Oxocitronellyl enol
Reference Authors Davis EM, Ringer KL, McConkey ME, Croteau R
Title Monoterpene metabolism. Cloning, expression, and characterization of menthone reductases from peppermint.
Journal Reference Authors Duetz WA, Fjallman AH, Ren S, Jourdat C, Witholt B
Title Biotransformation of D-limonene to (+) trans-carveol by toluene-grown Rhodococcus opacus PWD4 cells.
Journal Reference Authors Chen F, Ro DK, Petri J, Gershenzon J, Bohlmann J, Pichersky E, Tholl D
Title Characterization of a root-specific Arabidopsis terpene synthase responsible for the formation of the volatile monoterpene 1,8-cineole.
Journal Reference Authors Trudgill PW
Title Microbial metabolism of monoterpenes--recent developments.
Journal Reference Authors Ikeda H, Esaki N, Nakai S, Hashimoto K, Uesato S, Soda K, Fujita T
Title Acyclic monoterpene primary alcohol:NADP+ oxidoreductase of Rauwolfia serpentina cells: the key enzyme in biosynthesis of monoterpene alcohols.
Journal J Biochem 109:341-7 (1991)
Reference Authors Yamamoto H, Katano N, Ooi A, Inoue K.
Title Secologanin synthase which catalyzes the oxidative cleavage of loganin into secologanin is a cytochrome P450.
Journal Reference Authors Katano N, Yamamoto H, Iio R, Inoue K.
Title 7-Deoxyloganin 7-hydroxylase in Lonicera japonica cell cultures.
Journal Related rn00900 Terpenoid backbone biosynthesis
rn00901 Indole alkaloid biosynthesis
rn00907 Pinene, camphor and geraniol degradation
KO pathway
