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MetaCyc Pathway: brassinosteroid biosynthesis I
Inferred from experiment

Pathway diagram: brassinosteroid biosynthesis I

If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Synonyms: brassinosteroid biosynthesis - early and late C-6 oxidation pathways

Superclasses: BiosynthesisHormones BiosynthesisPlant Hormones BiosynthesisBrassinosteroids Biosynthesis

Some taxa known to possess this pathway include : Arabidopsis thaliana col, Solanum lycopersicum

Expected Taxonomic Range: Embryophyta

Brassinosteroids are steroidal hormones that regulate the growth and development of plants. Brassinosteroids are C27, C28 and C29 steroids depending on their C-24 alkyl substituents. More than 50 free, naturally occurring brassinosteroids have been identified in plants, of which brassinolide (BL) is the most biologically active C28, and together with its C28 congeners, is distributed widely in the plant kingdom [Clouse98]. The biosynthesis pathway of brassinolide was initially elucidated using cultured Catharanthus roseus cells. Extensive metabolic studies suggested parallel-branched brassinolide pathways, namely the early and late C-6 oxidation pathways [Fujioka03]. It has proposed that the late C-6 oxidation pathway plays a predominant role in the light, whereas the early C-6 oxidation pathway is dominant in the dark [Noguchi00]. Recent studies suggest that there is a crosstalk between these parallel pathways, implying that they are not totally autonomous. The operation of an early C-22 oxidation branch of the brassinosteroid biosynthetic pathway has also been demonstrated (see brassinosteroid biosynthesis II) [Fujioka02]. Thus, brassinosteroid biosynthesis pathways are highly networked. The identification of Arabidopsis mutants defective in enzymes of the various branches of the brassinosteroids biosynthesis pathway has been instrumental in the elucidation of the many steps of the biosynthesis of those compounds. Those mutants often display a dwarf phenotype. Although the current evidence indicates that both the early and late C-6 oxidation pathways are common in the plant kingdom, as seen in plants such as rice, pea and zinnia [Yamamoto01a, Nomura97a, Hong02], it appears that in tomato and tobacco the late C-6 oxidation pathway is predominant as endogenous brassinosteroids of these species comprise only members of this branch [Yokota01, Koka00, Bishop99]. A putative brassinosteroid receptor has been described: BRI1 [Wang01a]. Although many of the genes encoding brassinosteroid biosynthetic enzymes have been cloned using brassinosteroid biosynthetic mutants, with the exception of the enzymes encoded by DWF4 and DET2, few have been expressed and purified.

Citations: [Friedrichsen01, Altmann98, Ohnishi06]

Superpathways: superpathway of C28 brassinosteroid biosynthesis

Unification Links: AraCyc:PWY-699

Revised 13-Jul-2010 by Zhang P


Altmann98: Altmann T (1998). "A tale of dwarfs and drugs: brassinosteroids to the rescue." Trends Genet 1998;14(12);490-5. PMID: 9865154

Bishop99: Bishop GJ, Nomura T, Yokota T, Harrison K, Noguchi T, Fujioka S, Takatsuto S, Jones JD, Kamiya Y (1999). "The tomato DWARF enzyme catalyses C-6 oxidation in brassinosteroid biosynthesis." Proc Natl Acad Sci U S A 96(4);1761-6. PMID: 9990098

Clouse98: Clouse SD, Sasse JM (1998). "BRASSINOSTEROIDS: Essential Regulators of Plant Growth and Development." Annu Rev Plant Physiol Plant Mol Biol 49;427-451. PMID: 15012241

Friedrichsen01: Friedrichsen D, Chory J (2001). "Steroid signaling in plants: from the cell surface to the nucleus." Bioessays 2001;23(11);1028-36. PMID: 11746219

Fujioka02: Fujioka S, Takatsuto S, Yoshida S (2002). "An early C-22 oxidation branch in the brassinosteroid biosynthetic pathway." Plant Physiol 130(2);930-9. PMID: 12376657

Fujioka03: Fujioka S, Yokota T (2003). "Biosynthesis and metabolism of brassinosteroids." Annu Rev Plant Biol 54;137-64. PMID: 14502988

Hong02: Hong Z, Ueguchi-Tanaka M, Shimizu-Sato S, Inukai Y, Fujioka S, Shimada Y, Takatsuto S, Agetsuma M, Yoshida S, Watanabe Y, Uozu S, Kitano H, Ashikari M, Matsuoka M (2002). "Loss-of-function of a rice brassinosteroid biosynthetic enzyme, C-6 oxidase, prevents the organized arrangement and polar elongation of cells in the leaves and stem." Plant J 32(4);495-508. PMID: 12445121

Koka00: Koka CV, Cerny RE, Gardner RG, Noguchi T, Fujioka S, Takatsuto S, Yoshida S, Clouse SD (2000). "A putative role for the tomato genes DUMPY and CURL-3 in brassinosteroid biosynthesis and response." Plant Physiol 122(1);85-98. PMID: 10631252

Noguchi00: Noguchi T, Fujioka S, Choe S, Takatsuto S, Tax FE, Yoshida S, Feldmann KA (2000). "Biosynthetic pathways of brassinolide in Arabidopsis." Plant Physiol 2000;124(1);201-9. PMID: 10982435

Nomura97a: Nomura T, Nakayama M, Reid JB, Takeuchi Y, Yokota T (1997). "Blockage of Brassinosteroid Biosynthesis and Sensitivity Causes Dwarfism in Garden Pea." Plant Physiol 113(1);31-37. PMID: 12223591

Ohnishi06: Ohnishi T, Szatmari AM, Watanabe B, Fujita S, Bancos S, Koncz C, Lafos M, Shibata K, Yokota T, Sakata K, Szekeres M, Mizutani M (2006). "C-23 hydroxylation by Arabidopsis CYP90C1 and CYP90D1 reveals a novel shortcut in brassinosteroid biosynthesis." Plant Cell 18(11);3275-88. PMID: 17138693

Wang01a: Wang ZY, Seto H, Fujioka S, Yoshida S, Chory J (2001). "BRI1 is a critical component of a plasma-membrane receptor for plant steroids." Nature 2001;410(6826);380-3. PMID: 11268216

Yamamoto01a: Yamamoto R, Fujioka S, Demura T, Takatsuto S, Yoshida S, Fukuda H (2001). "Brassinosteroid levels increase drastically prior to morphogenesis of tracheary elements." Plant Physiol 125(2);556-63. PMID: 11161013

Yokota01: Yokota T, Sato T, Takeuchi Y, Nomura T, Uno K, Watanabe T, Takatsuto S (2001). "Roots and shoots of tomato produce 6-deoxo-28-norcathasterone, 6-deoxo-28-nortyphasterol and 6-deoxo-28-norcastasterone, possible precursors of 28-norcastasterone." Phytochemistry 58(2);233-8. PMID: 11551544

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Asami01: Asami T, Mizutani M, Fujioka S, Goda H, Min YK, Shimada Y, Nakano T, Takatsuto S, Matsuyama T, Nagata N, Sakata K, Yoshida S (2001). "Selective interaction of triazole derivatives with DWF4, a cytochrome P450 monooxygenase of the brassinosteroid biosynthetic pathway, correlates with brassinosteroid deficiency in planta." J Biol Chem 276(28);25687-91. PMID: 11319239

Asami03: Asami T, Mizutani M, Shimada Y, Goda H, Kitahata N, Sekimata K, Han SY, Fujioka S, Takatsuto S, Sakata K, Yoshida S (2003). "Triadimefon, a fungicidal triazole-type P450 inhibitor, induces brassinosteroid deficiency-like phenotypes in plants and binds to DWF4 protein in the brassinosteroid biosynthesis pathway." Biochem J 369(Pt 1);71-6. PMID: 12350224

Bancos02: Bancos S, Nomura T, Sato T, Molnar G, Bishop GJ, Koncz C, Yokota T, Nagy F, Szekeres M (2002). "Regulation of transcript levels of the Arabidopsis cytochrome p450 genes involved in brassinosteroid biosynthesis." Plant Physiol 130(1);504-13. PMID: 12226529

Choe01: Choe S, Fujioka S, Noguchi T, Takatsuto S, Yoshida S, Feldmann KA (2001). "Overexpression of DWARF4 in the brassinosteroid biosynthetic pathway results in increased vegetative growth and seed yield in Arabidopsis." Plant J 26(6);573-82. PMID: 11489171

Choe98: Choe S, Dilkes BP, Fujioka S, Takatsuto S, Sakurai A, Feldmann KA (1998). "The DWF4 gene of Arabidopsis encodes a cytochrome P450 that mediates multiple 22alpha-hydroxylation steps in brassinosteroid biosynthesis." Plant Cell 1998;10(2);231-43. PMID: 9490746

Choe99: Choe S, Noguchi T, Fujioka S, Takatsuto S, Tissier CP, Gregory BD, Ross AS, Tanaka A, Yoshida S, Tax FE, Feldmann KA (1999). "The Arabidopsis dwf7/ste1 mutant is defective in the delta7 sterol C-5 desaturation step leading to brassinosteroid biosynthesis." Plant Cell 1999;11(2);207-21. PMID: 9927639

Ephritikhine99: Ephritikhine G, Pagant S, Fujioka S, Takatsuto S, Lapous D, Caboche M, Kendrick RE, Barbier-Brygoo H (1999). "The sax1 mutation defines a new locus involved in the brassinosteroid biosynthesis pathway in Arabidopsis thaliana." Plant J 18(3);315-20. PMID: 10377996

Finsterbusch99: Finsterbusch A, Lindemann P, Grimm R, Eckerskorn C, Luckner M (1999). "Delta(5)-3beta-hydroxysteroid dehydrogenase from Digitalis lanata Ehrh. - a multifunctional enzyme in steroid metabolism?." Planta 209(4);478-86. PMID: 10550629

Fujioka97: Fujioka S, Li J, Choi YH, Seto H, Takatsuto S, Noguchi T, Watanabe T, Kuriyama H, Yokota T, Chory J, Sakurai A (1997). "The Arabidopsis deetiolated2 mutant is blocked early in brassinosteroid biosynthesis." Plant Cell 9(11);1951-62. PMID: 9401120

Fujita06: Fujita S, Ohnishi T, Watanabe B, Yokota T, Takatsuto S, Fujioka S, Yoshida S, Sakata K, Mizutani M (2006). "Arabidopsis CYP90B1 catalyses the early C-22 hydroxylation of C27, C28 and C29 sterols." Plant J 45(5);765-74. PMID: 16460510

Katsumata08: Katsumata T, Hasegawa A, Fujiwara T, Komatsu T, Notomi M, Abe H, Natsume M, Kawaide H (2008). "Arabidopsis CYP85A2 catalyzes lactonization reactions in the biosynthesis of 2-deoxy-7-oxalactone brassinosteroids." Biosci Biotechnol Biochem 72(8);2110-7. PMID: 18685225

Kim05a: Kim GT, Fujioka S, Kozuka T, Tax FE, Takatsuto S, Yoshida S, Tsukaya H (2005). "CYP90C1 and CYP90D1 are involved in different steps in the brassinosteroid biosynthesis pathway in Arabidopsis thaliana." Plant J 41(5);710-21. PMID: 15703058

Kim05b: Kim TW, Hwang JY, Kim YS, Joo SH, Chang SC, Lee JS, Takatsuto S, Kim SK (2005). "Arabidopsis CYP85A2, a cytochrome P450, mediates the Baeyer-Villiger oxidation of castasterone to brassinolide in brassinosteroid biosynthesis." Plant Cell 17(8);2397-412. PMID: 16024588

Lachance90: Lachance Y, Luu-The V, Labrie C, Simard J, Dumont M, de Launoit Y, Guerin S, Leblanc G, Labrie F (1990). "Characterization of human 3 beta-hydroxysteroid dehydrogenase/delta 5-delta 4-isomerase gene and its expression in mammalian cells." J Biol Chem 265(33);20469-75. PMID: 2243100

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Li97a: Li J, Biswas MG, Chao A, Russell DW, Chory J (1997). "Conservation of function between mammalian and plant steroid 5alpha-reductases." Proc Natl Acad Sci U S A 94(8);3554-9. PMID: 9108014

Noguchi99: Noguchi T, Fujioka S, Takatsuto S, Sakurai A, Yoshida S, Li J, Chory J (1999). "Arabidopsis det2 is defective in the conversion of (24R)-24-methylcholest-4-En-3-one to (24R)-24-methyl-5alpha-cholestan-3-one in brassinosteroid biosynthesis." Plant Physiol 120(3);833-40. PMID: 10398719

Nomura04: Nomura T, Jager CE, Kitasaka Y, Takeuchi K, Fukami M, Yoneyama K, Matsushita Y, Nyunoya H, Takatsuto S, Fujioka S, Smith JJ, Kerckhoffs LH, Reid JB, Yokota T (2004). "Brassinosteroid deficiency due to truncated steroid 5alpha-reductase causes dwarfism in the lk mutant of pea." Plant Physiol 135(4);2220-9. PMID: 15286289

Nomura05: Nomura T, Kushiro T, Yokota T, Kamiya Y, Bishop GJ, Yamaguchi S (2005). "The last reaction producing brassinolide is catalyzed by cytochrome P-450s, CYP85A3 in tomato and CYP85A2 in Arabidopsis." J Biol Chem 280(18);17873-9. PMID: 15710611

Rheaume91: Rheaume E, Lachance Y, Zhao HF, Breton N, Dumont M, de Launoit Y, Trudel C, Luu-The V, Simard J, Labrie F (1991). "Structure and expression of a new complementary DNA encoding the almost exclusive 3 beta-hydroxysteroid dehydrogenase/delta 5-delta 4-isomerase in human adrenals and gonads." Mol Endocrinol 5(8);1147-57. PMID: 1944309

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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