phytosterol biosynthesis (plants)

Benveniste P. Biosynthesis and accumulation of sterols. Annu Rev Plant Biol. 2004;55():429–57. doi: 10.1146/annurev.arplant.55.031903.141616. PMID: 15377227.; Schrick K, Fujioka S, Takatsuto S, Stierhof Y, Stransky H, Yoshida S, Jürgens G. A link between sterol biosynthesis, the cell wall, and cellulose in Arabidopsis. The Plant Journal. 2004 Mar;38(2):227–43. doi: 10.1111/j.1365-313x.2004.02039.x.; Holmberg N, Harker M, Gibbard CL, Wallace AD, Clayton JC, Rawlins S, Hellyer A, Safford R. Sterol C-24 methyltransferase type 1 controls the flux of carbon into sterol biosynthesis in tobacco seed. Plant Physiol. 2002 Sep;130(1):303–11. PMID: 12226510; PMCID: PMC166563.; Clouse SD. Arabidopsis mutants reveal multiple roles for sterols in plant development. Plant Cell. 2002 Sep;14(9):1995–2000. PMID: 12215500; PMCID: PMC543216.; Schrick K, Mayer U, Martin G, Bellini C, Kuhnt C, Schmidt J, Jürgens G. Interactions between sterol biosynthesis genes in embryonic development of Arabidopsis. The Plant Journal. 2002 Jul;31(1):61–73. doi: 10.1046/j.1365-313x.2002.01333.x.; Kushiro M, Nakano T, Sato K, Yamagishi K, Asami T, Nakano A, Takatsuto S, Fujioka S, Ebizuka Y, Yoshida S. Obtusifoliol 14a-Demethylase (CYP51) Antisense Arabidopsis Shows Slow Growth and Long Life. Biochemical and Biophysical Research Communications. 2001 Jul;285(1):98–104. doi: 10.1006/bbrc.2001.5122.; Schaeffer A, Bronner R, Benveniste P, Schaller H. The ratio of campesterol to sitosterol that modulates growth in Arabidopsis is controlled by STEROL METHYLTRANSFERASE 2;1. The Plant Journal. 2001 Mar;25(6):605–15. doi: 10.1046/j.1365-313x.2001.00994.x.; Rondet S, Taton M, Rahier A. Identification, characterization, and partial purification of 4 alpha-carboxysterol-C3-dehydrogenase/ C4-decarboxylase from Zea mays. Arch Biochem Biophys. 1999 Jun 15;366(2):249–60. doi: 10.1006/abbi.1999.1218. PMID: 10356290.; Choe S, Noguchi T, Fujioka S, Takatsuto S, Tissier CP, Gregory BD, Ross AS, Tanaka A, Yoshida S, Tax FE, Feldmann KA. The Arabidopsis dwf7/ste1 Mutant Is Defective in the ?7 Sterol C-5 Desaturation Step Leading to Brassinosteroid Biosynthesis. Plant Cell. 1999 Feb;11(2):207–21. doi: 10.1105/tpc.11.2.207.; Grebenok RJ, Ohnmeiss TE, Yamamoto A, Huntley ED, Galbraith DW, Della Penna D. Isolation and characterization of an Arabidopsis thaliana C-8,7 sterol isomerase: functional and structural similarities to mammalian C-8,7 sterol isomerase/emopamil-binding protein. Plant Mol Biol. 1998 Nov;38(5):807–15. doi: 10.1023/a:1006028623875. PMID: 9862498.; Klahre U, Noguchi T, Fujioka S, Takatsuto S, Yokota T, Nomura T, Yoshida S, Chua N. The Arabidopsis DIMINUTO/DWARF1 Gene Encodes a Protein Involved in Steroid Synthesis. Plant Cell. 1998 Oct;10(10):1677–90. doi: 10.1105/tpc.10.10.1677.; Pascal S, Taton M, Rahier A. Plant Sterol Biosynthesis: Identification of a NADPH Dependent Sterone Reductase Involved in Sterol-4 Demethylation. Archives of Biochemistry and Biophysics. 1994 Jul;312(1):260–71. doi: 10.1006/abbi.1994.1308.; Taton M, Rahier A. Properties and structural requirements for substrate specificity of cytochrome P-450-dependent obtusifoliol 14 alpha-demethylase from maize (Zea mays) seedlings. Biochem J. 1991 Jul 15;277 ( Pt 2)():483–92. PMID: 1859375; PMCID: PMC1151260.

Metabolites

24-Ethylidenelophenol

Formula: C30H50O (426.386145)

CAS ID: 474-40-8

24-Methylenecholesterol

Formula: C28H46O (398.3548466)

CAS ID: 474-63-5

24-Methylenelophenol

Formula: C29H48O (412.37049579999996)

CAS ID: 1176-52-9

4alpha-Methylfecosterol

Formula: C29H48O (412.37049579999996)

CAS ID: 17757-07-2

5-Dehydroavenasterol

Formula: C29H46O (410.3548466)

CAS ID: 29560-28-9

5-Dehydroepisterol

Formula: C28H44O (396.3391974)

CAS ID: 23582-83-4

Brassicasterol

Formula: C28H46O (398.3548466)

CAS ID: 474-67-9

CO2

Formula: CO2 (43.98983)

CAS ID: 124-38-9

Cycloartenol

Formula: C30H50O (426.386145)

CAS ID: 469-38-5

Cycloeucalenol

Formula: C30H50O (426.386145)

CAS ID: 469-39-6

Delta7-Avenasterol

Formula: C29H48O (412.37049579999996)

CAS ID: 23290-26-8

Formate

Formula: CH2O2 (46.0054792)

CAS ID: 64-18-6

gamma-Sitosterol

Formula: C29H50O (414.386145)

CAS ID: 83-47-6

H+

Formula: H (1.0078246)

CAS ID: 12408-02-5

H2O

Formula: H2O (18.0105642)

CAS ID: 7732-18-5

Indole-3-acetate

Formula: C10H9NO2 (175.0633254)

CAS ID: 87-51-4

Isofucosterol

Formula: C29H48O (412.37049579999996)

CAS ID: 481-14-1

Oxygen

Formula: O2 (31.98983)

CAS ID: 7782-44-7

Stigmasterol

Formula: C29H48O (412.37049579999996)

CAS ID: 83-48-7

Dihydrobrassicasterol

Formula: C28H48O (400.37049579999996)

CAS ID: 4651-51-8

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

A25822B

Formula: C28H45NO (411.350096)

CAS ID: 50686-98-1



Enzyme

EC Number name full name note
1.1.1.418 plant 3beta-hydroxysteroid-4alpha-carboxylate 3-dehydrogenase (decarboxylating) 3beta-hydroxysteroid-4alpha-carboxylate:NAD+ 3-oxidoreductase (decarboxylating)
1.14.18.11 plant 4alpha-monomethylsterol monooxygenase 24-ethylidenelophenol,ferrocytochrome-b5:oxygen oxidoreductase (C-4alpha-methyl-hydroxylating)
1.14.18.9 4alpha-methylsterol monooxygenase 4,4-dimethyl-5alpha-cholest-7-en-3beta-ol,ferrocytochrome-b5:oxygen oxidoreductase (C4alpha-methyl-hydroxylating)
1.14.19.20 DELTA7-sterol 5(6)-desaturase DELTA7-sterol,ferrocytochrome b5:oxygen oxidoreductase 5,6-dehydrogenating
1.14.19.41 sterol 22-desaturase ergosta-5,7,24(28)-trien-3beta-ol,NADPH:oxygen oxidoreductase (22,23-dehydrogenating)
1.3.1.21 7-dehydrocholesterol reductase cholesterol:NADP+ DELTA7-oxidoreductase
1.3.1.70 DELTA14-sterol reductase 4,4-dimethyl-5alpha-cholesta-8,24-dien-3beta-ol:NADP+ DELTA14-oxidoreductase
1.3.1.72 DELTA24-sterol reductase sterol:NADP+ DELTA24-oxidoreductase
2.1.1.143 24-methylenesterol C-methyltransferase S-adenosyl-L-methionine:24-methylenelophenol C-methyltransferase
2.1.1.41 sterol 24-C-methyltransferase S-adenosyl-L-methionine:zymosterol 24-C-methyltransferase
5.3.3.5 cholestenol DELTA-isomerase DELTA7-Cholestenol DELTA7-DELTA8-isomerase
5.5.1.9 Cycloeucalenol cycloisomerase Cycloeucalenol lyase (cyclopropane-decyclizing)


Proteins

Protein ID name full name