brassinosteroid biosynthesis I

Ohnishi T, Szatmari AM, Watanabe B, Fujita S, Bancos S, Koncz C, Lafos M, Shibata K, Yokota T, Sakata K, Szekeres M, Mizutani M. C-23 hydroxylation by Arabidopsis CYP90C1 and CYP90D1 reveals a novel shortcut in brassinosteroid biosynthesis. Plant Cell. 2006 Nov;18(11):3275–88. PMID: 17138693; PMCID: PMC1693957.; Kim TW, Hwang JY, Kim YS, Joo SH, Chang SC, Lee JS, Takatsuto S, Kim SK. Arabidopsis CYP85A2, a cytochrome P450, mediates the Baeyer-Villiger oxidation of castasterone to brassinolide in brassinosteroid biosynthesis. Plant Cell. 2005 Aug;17(8):2397–412. PMID: 16024588; PMCID: PMC1182497.; Fujioka S, Yokota T. Biosynthesis and metabolism of brassinosteroids. Annu Rev Plant Biol. 2003;54():137–64. doi: 10.1146/annurev.arplant.54.031902.134921. PMID: 14502988.; Friedrichsen D, Chory J. Steroid signaling in plants: from the cell surface to the nucleus. Bioessays. 2001 Nov;23(11):1028–36. doi: 10.1002/bies.1148. PMID: 11746219.; Shimada Y, Fujioka S, Miyauchi N, Kushiro M, Takatsuto S, Nomura T, Yokota T, Kamiya Y, Bishop GJ, Yoshida S. Brassinosteroid-6-oxidases from Arabidopsis and tomato catalyze multiple C-6 oxidations in brassinosteroid biosynthesis. Plant Physiol. 2001 Jun;126(2):770–9. PMID: 11402205; PMCID: PMC111167.; Wang ZY, Seto H, Fujioka S, Yoshida S, Chory J. BRI1 is a critical component of a plasma-membrane receptor for plant steroids. Nature. 2001 Mar 15;410(6826):380–3. doi: 10.1038/35066597. PMID: 11268216.; Noguchi T, Fujioka S, Choe S, Takatsuto S, Tax FE, Yoshida S, Feldmann KA. Biosynthetic pathways of brassinolide in Arabidopsis. Plant Physiol. 2000 Sep;124(1):201–9. PMID: 10982435; PMCID: PMC59135.; Altmann T. A tale of dwarfs and drugs: brassinosteroids to the rescue. Trends Genet. 1998 Dec;14(12):490–5. doi: 10.1016/s0168-9525(98)01598-4. PMID: 9865154.

Metabolites

3-Dehydroteasterone

Formula: C28H46O4 (446.3395916)

CAS ID: 124853-28-7

5alpha-Campestan-3-one

Formula: C28H48O (400.37049579999996)

CAS ID: 27212-88-0

6-Deoxocastasterone

Formula: C28H50O4 (450.37089000000003)

CAS ID: 87833-54-3

6-Deoxocathasterone

Formula: C28H50O2 (418.38106)

CAS ID: 198416-73-8

6-Deoxoteasterone

Formula: C28H50O3 (434.37597500000004)

CAS ID: 188397-19-5

6-Deoxotyphasterol

Formula: C28H50O3 (434.37597500000004)

CAS ID: 164034-47-3

6-Oxocampestanol

Formula: C28H48O2 (416.36541079999995)

CAS ID: 168113-32-4

Campest-4-en-3-one

Formula: C28H46O (398.3548466)

CAS ID: 22260-46-4

Campestanol

Formula: C28H50O (402.386145)

CAS ID: 474-60-2

Campesterol

Formula: C28H48O (400.37049579999996)

CAS ID: 474-62-4

Castasterone

Formula: C28H48O5 (464.3501558)

CAS ID: 80736-41-0

Cathasterone

Formula: C28H48O3 (432.36032579999994)

CAS ID: 168146-23-4

H+

Formula: H (1.0078246)

CAS ID: 12408-02-5

H2O

Formula: H2O (18.0105642)

CAS ID: 7732-18-5

Oxygen

Formula: O2 (31.98983)

CAS ID: 7782-44-7

Teasterone

Formula: C28H48O4 (448.3552408)

CAS ID: 92751-21-8

Typhasterol

Formula: C28H48O4 (448.3552408)

CAS ID: 87734-68-7

NADPH(4-)

Formula: C21H26N7O17P3 (741.0598016)

CAS ID: 53-57-6

NAD(1-)

Formula: C21H26N7O14P2 (662.1012936000001)

CAS ID: 53-84-9

NADP(3-)

Formula: C21H25N7O17P3 (740.051977)

CAS ID: 53-59-8



Enzyme

EC Number name full name note
1.14.14.-
1.14.14.147 22alpha-hydroxysteroid 23-monooxygenase 22alpha-hydroxysteroid,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (C-23-hydroxylating)
1.14.14.178 steroid 22S-hydroxylase steroid,NADPH-hemoprotein reductase:oxygen 22S-oxidoreductase (hydroxylating)
1.14.14.179 brassinosteroid 6-oxygenase 6-deoxocastasterone,NADPH-hemoprotein reductase:oxygen 6-oxidoreductase (castasterone-forming)
1.14.14.180 brassinolide synthase castasterone,NADPH-hemoprotein reductase:oxygen oxidoreductase (lactonizing, brassinolide-forming)
1.14.19.79 3beta,22alpha-dihydroxysteroid 3-dehydrogenase 3beta,22alpha-dihydroxysteroid,[reduced NADPH-hemoprotein reductase]:oxygen 3-oxidoreductase
1.3.1.22 3-oxo-5alpha-steroid 4-dehydrogenase (NADP+) 3-oxo-5alpha-steroid:NADP+ DELTA4-oxidoreductase


Proteins

Protein ID name full name