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9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
9-cis-beta-apo-10'-carotenal + O2
carlactone + omega-OH-(4-CH3)heptanal
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additional information
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9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
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9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
CCD8-dependent conversion of beta-apo-10'-carotenal to unstable carlactone
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additional information
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enzyme additionally catalyzes the conversion of all-trans-10'-apo-beta-carotenal to 13-apo-beta-carotenone + (2E,4E,6E)-4-methylocta-2,4,6-trienedial, EC 1.13.11.70. The Formation of carlactone is about 10fold faster than the formation of 13-apo-beta-carotenone
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additional information
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CCD8-dependent conversion of all-trans-10'-apo-beta-carotenal to 13-apo-beta-carotenone, reaction of EC 1.13.11.70
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(2E)-3-(3,4-dimethoxyphenyl)-N-hydroxyprop-2-enamide
over 95% inhibition at 0.1 mM
(2E)-N-benzyl-N-hydroxy-3,7-dimethylocta-2,6-dienamide
52% inhibition at 0.1 mM
(2E)-N-hydroxy-3-(4-methoxyphenyl)prop-2-enamide
over 95% inhibition at 0.1 mM
(2E,4E)-N-benzyl-N-hydroxy-5,9-dimethyldeca-2,4,8-trienamide
47% inhibition at 0.1 mM
(2E,4E)-N-hydroxy-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienamide
over 95% inhibition at 0.1 mM
2-(2H-1,3-benzodioxol-5-yl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide
over 95% inhibition at 0.1 mM
2-(3,4-dimethoxyphenyl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide
over 95% inhibition at 0.1 mM
3-(3,4-dimethoxyphenyl)-N-hydroxy-N-octylpropanamide
over 95% inhibition at 0.1 mM
3-(3,4-dimethoxyphenyl)-N-hydroxypropanamide
78% inhibition at 0.1 mM
3-amino-N-benzyl-N-hydroxybenzamide
over 95% inhibition at 0.1 mM
abamine
over 95% inhibition at 0.1 mM
N-benzyl-2-(3,4-dimethoxyphenyl)-N-hydroxyacetamide
over 95% inhibition at 0.1 mM
N-benzyl-3-chloro-N-hydroxybenzamide
over 95% inhibition at 0.1 mM
N-benzyl-N-hydroxy-2-(4-hydroxyphenyl)acetamide
over 95% inhibition at 0.1 mM
N-benzyl-N-hydroxy-3,4-dimethoxybenzamide
over 95% inhibition at 0.1 mM
N-benzyl-N-hydroxy-3-(4-methoxyphenyl)propanamide
over 95% inhibition at 0.1 mM
N-benzyl-N-hydroxy-4-methoxybenzamide
over 95% inhibition at 0.1 mM
N-hydroxy-3-(4-methoxyphenyl)-N-octylpropanamide
over 95% inhibition at 0.1 mM
N-hydroxy-3-(4-methoxyphenyl)propanamide
over 95% inhibition at 0.1 mM
N-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-N-hydroxy-2-(4-methoxyphenyl)acetamide
70% inhibition at 0.1 mM
N-[(4-fluorophenyl)methyl]-N-hydroxy-2-(4-hydroxyphenyl)acetamide
over 95% inhibition at 0.1 mM
N-[(4-fluorophenyl)methyl]-N-hydroxy-2-(4-methoxyphenyl)acetamide
over 95% inhibition at 0.1 mM
N-[(4-fluorophenyl)methyl]-N-hydroxy-3,4-dimethoxybenzamide
over 95% inhibition at 0.1 mM
N-[(4-fluorophenyl)methyl]-N-hydroxy-3-(4-methoxyphenyl)propanamide
over 95% inhibition at 0.1 mM
N-[(4-fluorophenyl)methyl]-N-hydroxy-4-methoxybenzamide
over 95% inhibition at 0.1 mM
N1-[(4-fluorophenyl)methyl]-N1-hydroxy-N4-[(4-methoxyphenyl)methyl]butanediamide
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sodium 3-[hydroxy[(4-methoxyphenyl)acetyl]amino]propanoate
47% inhibition at 0.1 mM
sodium 3-[hydroxy[(naphthalen-2-yl)acetyl]amino]propanoate
92% inhibition at 0.1 mM
additional information
no evidence for feedback regulation
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additional information
AtCCD8 is inhibited in a time-dependent fashion by hydroxamic acids N-[(4-fluorophenyl)methyl]-N-hydroxy-2-(4-hydroxyphenyl)acetamide, N-[(4-fluorophenyl)methyl]-N-hydroxy-2-(4-methoxyphenyl)acetamide, N-benzyl-2-(3,4-dimethoxyphenyl)-N-hydroxyacetamide and 2-(3,4-dimethoxyphenyl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide with over 95% inhibition at 0.10 mM, hydroxamic acids acids N-[(4-fluorophenyl)methyl]-N-hydroxy-2-(4-hydroxyphenyl)acetamide, N-[(4-fluorophenyl)methyl]-N-hydroxy-2-(4-methoxyphenyl)acetamide, N-benzyl-2-(3,4-dimethoxyphenyl)-N-hydroxyacetamide and 2-(3,4-dimethoxyphenyl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide cause a shoot branching phenotype in Arabidopsis thaliana. Selective inhibition of CCD8 is observed using hydroxamic acids N-hydroxy-3-(4-methoxyphenyl)propanamide and N-[(4-fluorophenyl)methyl]-N-hydroxy-3-(4-methoxyphenyl)propanamide. No inhibition by N1-[(4-fluorophenyl)methyl]-N1-hydroxy-N4-[(4-methoxyphenyl)methyl]butanediamide
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malfunction
the biochemical basis of the shoot branching phenotype is due to inhibition of enzyme CCD8
metabolism
biosynthesis of strigolactones requires the action of two CCD enzymes, CCD7 (EC 1.13.11.68) and CCD8, which act sequentially on 9-cis-beta-carotene, strigolactone biosynthesis pathway from all-trans-beta-carotene to ent-2'-epi-5-deoxystrigol, overview
physiological function
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coexpression of the enzyme, CCD8, and carotenoid-9',10'-cleaving dioxygenase CCD7, EC 1.13.11.71, in Escherichia coli results in production of 13-apo-beta-carotenone. The sequential cleavages of beta-carotene by CCD7 and CCD8 are likely the initial steps in the synthesis of a carotenoid-derived signaling molecule that is necessary for the regulation lateral branching
physiological function
enzyme is involved in regulation of low phosphate stress responses. Mutants show lower anthocyanin content and longer primary root length. Mutant plants also display altered root architecture such as increased root-to-shoot ratio, lower lateral root number and root hair density compared with wild-type plants under low phosphate stress. Higher total phosphate contents are detected in shoots and roots of mutant plants than those of wild-type plants when subjected to low phosphate stress, which is associated, at least in part, with increase in expression of WRKY75 as well as AtPT1 and AtPT2 genes encoding high-affinity phosphate transporters
physiological function
loss-of-function mutants exhibit a significant decrease in petiole length and are highly branched. The axillary buds, which are typically delayed in growth in wild-type plants, grow out to produce leaves and inflorescences. The mutant plant have smaller rosette diameters due to a decrease in the lengths of petioles and leaf blades compared with wild-type plants. The phenotypes contribute to the bushy appearance of the mutants. The double mutant, additionally lacking carotenoid-9',10'-cleaving dioxygenase activity, EC 1.13.11.71, is phenotypically indistinguishable from either single mutant, indicating an interaction consistent with both genes functioning in the same pathway. Both classes of plants show a slight increase in inflorescence number compared with wild type
physiological function
mutations in the MAX4 gene of Arabidopsis result in increased and auxin-resistant bud growth. Increased branching in max4 shoots is restored to wild type by grafting to wild-type rootstocks, suggesting that MAX4 is required to produce a mobile branch-inhibiting signal, acting downstream of auxin
physiological function
biosynthesis of strigolactones requires the action of two CCD enzymes, CCD7 (EC 1.13.11.68) and CCD8, which act sequentially on 9-cis-beta-carotene
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Jiang, L.; Jian, H.; Qian, J.; Sun, Z.; Wei, Z.; Chen, X.; Cao, S.
MAX4 gene is involved in the regulation of low inorganic phosphate stress responses in Arabidopsis thaliana
Acta Physiol. Plant.
33
867-875
2011
Arabidopsis thaliana (Q8VY26)
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brenda
Sorefan, K.; Booker, J.; Haurogne, K.; Goussot, M.; Bainbridge, K.; Foo, E.; Chatfield, S.; Ward, S.; Beveridge, C.; Rameau, C.; Leyser, O.
MAX4 and RMS1 are orthologous dioxygenase-like genes that regulate shoot branching in Arabidopsis and pea
Genes Dev.
17
1469-1474
2003
Arabidopsis thaliana (Q8VY26)
brenda
Schwartz, S.H.; Qin, X.; Loewen, M.C.
The biochemical characterization of two carotenoid cleavage enzymes from Arabidopsis indicates that a carotenoid-derived compound inhibits lateral branching
J. Biol. Chem.
279
46940-46945
2004
Arabidopsis thaliana
brenda
Bainbridge, K.; Sorefan, K.; Ward, S.; Leyser, O.
Hormonally controlled expression of the Arabidopsis MAX4 shoot branching regulatory gene
Plant J.
44
569-580
2005
Arabidopsis thaliana (Q8VY26)
brenda
Auldridge, M.E.; Block, A.; Vogel, J.T.; Dabney-Smith, C.; Mila, I.; Bouzayen, M.; Magallanes-Lundback, M.; DellaPenna, D.; McCarty, D.R.; Klee, H.J.
Characterization of three members of the Arabidopsis carotenoid cleavage dioxygenase family demonstrates the divergent roles of this multifunctional enzyme family
Plant J.
45
982-993
2006
Arabidopsis thaliana (Q8VY26)
brenda
Alder, A.; Jamil, M.; Marzorati, M.; Bruno, M.; Vermathen, M.; Bigler, P.; Ghisla, S.; Bouwmeester, H.; Beyer, P.; Al-Babili, S.
The path from beta-carotene to carlactone, a strigolactone-like plant hormone
Science
335
1348-1351
2012
Arabidopsis thaliana (Q8VY26), Pisum sativum
brenda
Harrison, P.J.; Newgas, S.A.; Descombes, F.; Shepherd, S.A.; Thompson, A.J.; Bugg, T.D.
Biochemical characterization and selective inhibition of beta-carotene cis-trans isomerase D27 and carotenoid cleavage dioxygenase CCD8 on the strigolactone biosynthetic pathway
FEBS J.
282
3986-4000
2015
Arabidopsis thaliana (Q8VY26)
brenda
Priya, R.; Sneha, P.; Rivera Madrid, R.; Doss, C.G.P.; Singh, P.; Siva, R.
Molecular modeling and dynamic simulation of Arabidopsis thaliana carotenoid cleavage dioxygenase gene a comparison with Bixa orellana and Crocus sativus
J. Cell. Biochem.
118
2712-2721
2017
Arabidopsis thaliana (Q8VY26)
brenda
Jia, K.; Baz, L.; Al-Babili, S.
From carotenoids to strigolactones
J. Exp. Bot.
69
2189-2204
2018
Arabidopsis thaliana
brenda
Fernandez, I.; Cosme, M.; Stringlis, I.; Yu, K.; de Jonge, R.; van Wees, S.; Pozo, M.; Pieterse, C.; van der Heijden, M.
Molecular dialogue between arbuscular mycorrhizal fungi and the nonhost plant Arabidopsis thaliana switches from initial detection to antagonism
New Phytol.
223
867-881
2019
Arabidopsis thaliana (Q8VY26)
brenda
Batra, R.; Agarwal, P.; Tyagi, S.; Saini, D.K.; Kumar, V.; Kumar, A.; Kumar, S.; Balyan, H.S.; Pandey, R.; Gupta, P.K.
A study of CCD8 genes/proteins in seven monocots and eight dicots
PLoS ONE
14
e0213531
2019
Aegilops tauschii, Arabidopsis thaliana (Q8VY26), Brachypodium distachyon, Glycine max (A0A2H4GW71), Medicago truncatula (G7J3F4), Oryza sativa Japonica Group (Q8LIY8), Populus trichocarpa, Prunus persica, Solanum lycopersicum, Sorghum bicolor (C5XK17), Theobroma cacao (A0A061GRL5), Triticum aestivum, Triticum urartu, Vitis vinifera, Zea mays (C4PJN4)
brenda