KEGG   PATHWAY: ko00902
Entry
ko00902                     Pathway                                
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
ko00902  Monoterpenoid biosynthesis
ko00902

Other DBs
GO: 0016099
Orthology
K12467  myrcene/ocimene synthase [EC:4.2.3.15]
K21925  (-)-camphene/tricyclene/(4S)-limonene/myrcene synthase [EC:4.2.3.117 4.2.3.105 4.2.3.16 4.2.3.15]
K21069  ipsdienol synthase [EC:1.14.14.31]
K20142  ipsdienol dehydrogenase [EC:1.1.1.386]
K15086  (3S)-linalool synthase [EC:4.2.3.25]
K22049  S-linalool synthase [EC:4.2.3.25]
K15087  (3R)-linalool synthase [EC:4.2.3.26]
K05525  linalool 8-monooxygenase [EC:1.14.14.84]
K23810  (E)-8-carboxylinalool synthase [EC:1.14.14.-]
K15088  (4S)-limonene synthase [EC:4.2.3.16]
K21926  (+)-alpha-terpineol/(4S)-limonene synthase [EC:4.2.3.112 4.2.3.16]
K15089  (S)-limonene 3-monooxygenase [EC:1.14.14.99]
K15090  isopiperitenol dehydrogenase [EC:1.1.1.223]
K15091  (-)-isopiperitenone reductase [EC:1.3.1.82]
K15092  (+)-pulegone reductase [EC:1.3.1.81]
K15093  (+)-menthofuran synthase [EC:1.14.14.143]
K15094  (-)-menthol dehydrogenase [EC:1.1.1.207]
K15095  (+)-neomenthol dehydrogenase [EC:1.1.1.208]
K07381  (S)-limonene 6-monooxygenase [EC:1.14.14.51]
K07382  (S)-limonene 7-monooxygenase [EC:1.14.14.52]
K15096  (R)-limonene synthase [EC:4.2.3.20]
K07384  (-)-alpha/(-)-beta-pinene synthase [EC:4.2.3.119 4.2.3.120]
K22050  (-)-beta-pinene synthase [EC:4.2.3.120]
K15097  (-)-endo-fenchol synthase [EC:4.2.3.10]
K07385  1,8-cineole synthase [EC:4.2.3.108]
K18108  (-)-alpha-terpineol synthase [EC:4.2.3.111]
K21120  1,8-cineole 2-endo-monooxygenase [EC:1.14.14.133]
K22208  (-)-camphene synthase [EC:4.2.3.117]
K21938  (+)-car-3-ene synthase [EC:4.2.3.107]
K15098  bornyl diphosphate synthase [EC:5.5.1.8]
K20979  geranyl diphosphate diphosphatase [EC:3.1.7.11]
K20986  geranyl diphosphate phosphohydrolase [EC:3.6.1.68]
K15099  geraniol 8-hydroxylase [EC:1.14.14.83]
K23232  8-hydroxygeraniol dehydrogenase [EC:1.1.1.324]
K20144  (S)-8-oxocitronellyl enol synthase [EC:1.3.1.122]
K23990  nepetalactol dehydrogenase / (+)-cis,trans-nepetalactol synthase [EC:1.1.1.419 5.5.1.34]
K23862  (+)-cis,trans-nepetalactol synthase [EC:5.5.1.34]
K20618  nepetalactol monooxygenase [EC:1.14.14.161]
K21373  7-deoxyloganetic acid glucosyltransferase [EC:2.4.1.323]
K21374  7-deoxyloganetin glucosyltransferase [EC:2.4.1.324]
K23276  7-deoxyloganate 7-hydroxylase [EC:1.14.14.85]
K13400  secologanin synthase [EC:1.14.19.62]
Compound
C00341  Geranyl diphosphate
C00400  (-)-Menthol
C00521  (S)-Limonene
C00553  (+)-Neomenthol
C00808  (+)-Camphor
C00843  (-)-Menthone
C00848  6-Oxocineole
C00964  (-)-trans-Carveol
C01123  (-)-trans-Isopiperitenol
C01433  Loganin
C01500  Geraniol
C01512  Loganate
C01765  (+)-Borneol
C01767  (-)-Carvone
C01852  Secologanin
C01957  Secologanate
C02344  (-)-endo-Fenchol
C02452  (-)-Perillyl alcohol
C02462  Sabinene hydrate
C02485  (-)-Isopiperitenone
C03092  6-endo-Hydroxycineole
C03190  (+)-Bornyl diphosphate
C04433  (6E)-8-Hydroxylinalool
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
C06070  Iridotrial
C06071  Deoxyloganin
C06074  Myrcene
C06099  (R)-Limonene
C06304  (+)-Camphene
C06305  (-)-Camphene
C06307  (-)-beta-Pinene
C06308  (-)-alpha-Pinene
C09769  Asperuloside
C09782  Gentiopicrin
C09804  cis-trans-Nepetalactol
C09844  1,8-Cineole
C09893  Pulegone
C11382  (+)-3-Carene
C11383  (+)-(S)-Carvone
C11388  (-)-Linalool
C11389  (+)-Linalool
C11393  (-)-alpha-Terpineol
C11409  (+)-trans-Carveol
C11636  7-Deoxyloganate
C11672  10-Deoxygeniposidic acid
C11673  Geniposidic acid
C11951  (+)-cis-Isopulegone
C11952  (+)-Isomenthone
C17621  (6E)-8-Hydroxygeraniol
C17622  (6E)-8-Oxogeranial
C18025  (+)-Menthofuran
C18027  (4R,7S)-7-Isopropyl-4-methyloxepan-2-one
C20221  (6E)-8-Oxolinalool
C20789  7-Deoxyloganetate
C20790  7-Deoxyloganetin
C20943  (R)-Ipsdienol
C20944  Ipsdienone
C21203  Geranyl phosphate
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
Plant Physiol 137:873-81 (2005)
DOI:10.1104/pp.104.053306
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
Appl Environ Microbiol 67:2829-32 (2001)
DOI:10.1128/AEM.67.6.2829-2832.2001
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
Plant Physiol 135:1956-66 (2004)
DOI:10.1104/pp.104.044388
Reference
PMID:1368150
  Authors
Trudgill PW
  Title
Microbial metabolism of monoterpenes--recent developments.
  Journal
Biodegradation 1:93-105 (1990)
DOI:10.1007/BF00058829
Reference
PMID:1864846
  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
Phytochemistry 53:7-12 (2000)
DOI:10.1016/S0031-9422(99)00471-9
Reference
  Authors
Katano N, Yamamoto H, Iio R, Inoue K.
  Title
7-Deoxyloganin 7-hydroxylase in Lonicera japonica cell cultures.
  Journal
Phytochemistry 58:53-8 (2001)
DOI:10.1016/S0031-9422(01)00181-9
Related
pathway
ko00900  Terpenoid backbone biosynthesis
ko00901  Indole alkaloid biosynthesis
ko00903  Limonene degradation
ko00907  Pinene, camphor and geraniol degradation
LinkDB

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