ENTRY       sly00905                    Pathway
NAME        Brassinosteroid biosynthesis - Solanum lycopersicum (tomato)
DESCRIPTION Brassinosteroids are a group of plant steroid hormones that regulate growth and development. More than fifty naturally occurring brassinosteroids have been identified in a wide range of plant species. The most abundant and widely occurring brassinosteroids are C28 steroids, and among them brassinolide (BL) is the most biologically active. Plants have multiple pathways for biosynthesis of BL, which are derived from the steroid biosynthetic pathway. Two pathways from campestanol to castasterone (CS), C6 oxidation and the late-C6 oxidation pathways, operate in many plants. Another branching pathway, the early-C22 oxidation pathway, was demonstrated using a brassinosteroid-deficient mutant of Arabidopsis thaliana. Recently, a new shortcut pathway from campesterol to 6-deoxotyphasterol was demonstrated by a functional analysis of cytochrome P450 monooxygenases responsible for brassinosteroid biosynthesis. Thus, at least four pathways are involved in the biosynthesis of CS, and CS is further metabolized to BL by lactonization of the B ring.
CLASS       Metabolism; Metabolism of terpenoids and polyketides
PATHWAY_MAP sly00905  Brassinosteroid biosynthesis
MODULE      sly_M00371  Castasterone biosynthesis, campesterol => castasterone [PATH:sly00905]
DBLINKS     GO: 0016132
ORGANISM    Solanum lycopersicum (tomato) [GN:sly]
GENE        101256342  CYP90B3; cytochrome P450 90B3 [KO:K09587] [EC:1.14.14.178]
            101265305  cytochrome P450 724B1 [KO:K12639] [EC:1.14.14.178]
            101251900  CYP724B2; cytochrome P450 724B1-like [KO:K12639] [EC:1.14.14.178]
            101255105  CYP90A5; cytochrome P450 90A5 [KO:K09588] [EC:1.14.19.79]
            543801  det2; steroid 5-alpha-reductase DET2 [KO:K09591] [EC:1.3.1.22]
            101256999  steroid 5-alpha-reductase DET2 [KO:K09591] [EC:1.3.1.22]
            101245605  3-epi-6-deoxocathasterone 23-monooxygenase [KO:K12637] [EC:1.14.14.147]
            101256170  cytochrome P450 90D2 [KO:K12638] [EC:1.14.14.147]
            100037489  CYP85A1; 6-deoxocastasterone oxidase isoform 1 [KO:K09590] [EC:1.14.14.179]
            100136888  CYP85A3; cytochrome P450 85A3 [KO:K25959] [EC:1.14.14.179 1.14.14.180]
            101252066  cytochrome P450 71A1-like [KO:K20623]
            101252373  cytochrome P450 71A1 [KO:K20623]
            100736487  CYP734A8; putative brassinosteroid hydroxylase [KO:K15639] [EC:1.14.-.-]
            100736544  CYP734A7; castasterone 26-hydroxylase [KO:K15639] [EC:1.14.-.-]
            101267535  cytochrome P450 734A1-like [KO:K15639] [EC:1.14.-.-]
COMPOUND    C01789  Campesterol
            C08814  Brassinolide
            C15784  Campest-4-en-3beta-ol
            C15785  Campest-4-en-3-one
            C15786  5alpha-Campestan-3-one
            C15787  Campestanol
            C15788  6alpha-Hydroxycampestanol
            C15789  6-Oxocampestanol
            C15790  Cathasterone
            C15791  Teasterone
            C15792  3-Dehydroteasterone
            C15793  Typhasterol
            C15794  Castasterone
            C15795  22alpha-Hydroxy-campesterol
            C15796  (22S)-22-Hydroxycampest-4-en-3-one
            C15797  22alpha-Hydroxy-5alpha-campestan-3-one
            C15798  6-Deoxocathasterone
            C15799  6-Deoxoteasterone
            C15800  3-Dehydro-6-deoxoteasterone
            C15801  6-Deoxotyphasterol
            C15802  6-Deoxocastasterone
            C15803  6alpha-Hydroxycastasterone
            C16251  3-epi-6-Deoxocathasterone
            C16252  (22R,23R)-22,23-Dihydroxycampesterol
            C16253  (22R,23R)-22,23-Dihydroxy-campest-4-en-3-one
            C17733  7-Oxateasterone
            C17735  7-Oxatyphasterol
            C19873  26-Hydroxycastasterone
            C19874  26-Hydroxybrassinolide
REFERENCE   
  AUTHORS   Koshiba K, Kamiya Y.
  TITLE     [Atarasii Syokubutuhorumon no Kagaku] (In Japanese)
  JOURNAL   Koudansya saientific:199-138 (2002)
REFERENCE   
  AUTHORS   Fukuda H, Matida Y, Kamiya Y, Kakimoto T.
  TITLE     [Shinpan Syokubutuhorumon no Sigunarudentatu] (In Japanese)
  JOURNAL   Syujyunsya:165-186 (2004)
REFERENCE   PMID:12529536
  AUTHORS   Shimada Y, Goda H, Nakamura A, Takatsuto S, Fujioka S, Yoshida S.
  TITLE     Organ-specific expression of brassinosteroid-biosynthetic genes and distribution of endogenous brassinosteroids in Arabidopsis.
  JOURNAL   Plant Physiol 131:287-97 (2003)
            DOI:10.1104/pp.013029
REFERENCE   
  AUTHORS   Choe, S.
  TITLE     Brassinosteroid biosynthesis and inactivation.
  JOURNAL   Physiol Plant 126:539-548 (2006)
            DOI:10.1111/j.1399-3054.2006.00681.x
REFERENCE   PMID:17138693
  AUTHORS   Ohnishi T, Szatmari AM, Watanabe B, Fujita S, Bancos S, Koncz C, Lafos M, Shibata K, Yokota T, Sakata K, Szekeres M, Mizutani M
  TITLE     C-23 hydroxylation by Arabidopsis CYP90C1 and CYP90D1 reveals a novel shortcut in brassinosteroid biosynthesis.
  JOURNAL   Plant Cell 18:3275-88 (2006)
            DOI:10.1105/tpc.106.045443
REFERENCE   PMID:17693126
  AUTHORS   Bishop GJ
  TITLE     Refining the plant steroid hormone biosynthesis pathway.
  JOURNAL   Trends Plant Sci 12:377-80 (2007)
            DOI:10.1016/j.tplants.2007.07.001
REFERENCE   PMID:15710611
  AUTHORS   Nomura T, Kushiro T, Yokota T, Kamiya Y, Bishop GJ, Yamaguchi S
  TITLE     The last reaction producing brassinolide is catalyzed by cytochrome P-450s, CYP85A3 in tomato and CYP85A2 in Arabidopsis.
  JOURNAL   J Biol Chem 280:17873-9 (2005)
            DOI:10.1074/jbc.M414592200
REFERENCE   PMID:18685225
  AUTHORS   Katsumata T, Hasegawa A, Fujiwara T, Komatsu T, Notomi M, Abe H, Natsume M, Kawaide H
  TITLE     Arabidopsis CYP85A2 catalyzes lactonization reactions in the biosynthesis of 2-deoxy-7-oxalactone brassinosteroids.
  JOURNAL   Biosci Biotechnol Biochem 72:2110-7 (2008)
            DOI:10.1271/bbb.80192
REFERENCE   PMID:15705958
  AUTHORS   Tanabe S, Ashikari M, Fujioka S, Takatsuto S, Yoshida S, Yano M, Yoshimura A, Kitano H, Matsuoka M, Fujisawa Y, Kato H, Iwasaki Y
  TITLE     A novel cytochrome P450 is implicated in brassinosteroid biosynthesis via the characterization of a rice dwarf mutant, dwarf11, with reduced seed length.
  JOURNAL   Plant Cell 17:776-90 (2005)
            DOI:10.1105/tpc.104.024950
REFERENCE   PMID:14615594
  AUTHORS   Hong Z, Ueguchi-Tanaka M, Umemura K, Uozu S, Fujioka S, Takatsuto S, Yoshida S, Ashikari M, Kitano H, Matsuoka M
  TITLE     A rice brassinosteroid-deficient mutant, ebisu dwarf (d2), is caused by a loss of function of a new member of cytochrome P450.
  JOURNAL   Plant Cell 15:2900-10 (2003)
            DOI:10.1105/tpc.014712
REL_PATHWAY sly00100  Steroid biosynthesis
KO_PATHWAY  ko00905
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