ENTRY       sly00902                    Pathway
NAME        Monoterpenoid biosynthesis - Solanum lycopersicum (tomato)
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 sly00902  Monoterpenoid biosynthesis
DBLINKS     GO: 0016099
ORGANISM    Solanum lycopersicum (tomato) [GN:sly]
GENE        101245212  TPS3; (-)-camphene/tricyclene synthase, chloroplastic [KO:K21925] [EC:4.2.3.117 4.2.3.105 4.2.3.16 4.2.3.15]
            101249864  (-)-camphene/tricyclene synthase, chloroplastic-like isoform X2 [KO:K21925] [EC:4.2.3.117 4.2.3.105 4.2.3.16 4.2.3.15]
            101261456  (+)-neomenthol dehydrogenase-like [KO:K15095] [EC:1.1.1.208]
            101263847  (+)-neomenthol dehydrogenase [KO:K15095] [EC:1.1.1.208]
            101251042  (+)-neomenthol dehydrogenase isoform X1 [KO:K15095] [EC:1.1.1.208]
            101268235  (+)-neomenthol dehydrogenase-like isoform X1 [KO:K15095] [EC:1.1.1.208]
            101260280  carbonyl reductase-like [KO:K15095] [EC:1.1.1.208]
            101258035  short-chain dehydrogenase/reductase 2b isoform X2 [KO:K15095] [EC:1.1.1.208]
            108281193  (+)-neomenthol dehydrogenase [KO:K15095] [EC:1.1.1.208]
            104649154  (+)-neomenthol dehydrogenase-like [KO:K15095] [EC:1.1.1.208]
            109118691  (+)-neomenthol dehydrogenase-like [KO:K15095] [EC:1.1.1.208]
            543602  8-hydroxygeraniol dehydrogenase [KO:K23232] [EC:1.1.1.324]
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   PMID:15728344
  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   PMID:11375201
  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   PMID:15299125
  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   PMID:10656401
  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   PMID:11524113
  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
REL_PATHWAY sly00900  Terpenoid backbone biosynthesis
            sly00903  Limonene and pinene degradation
KO_PATHWAY  ko00902
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