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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
-
-
-
-
?
all-trans-10'-apo-beta-carotenal + O2
13-apo-beta-carotenone + (2E,4E,6E)-4-methylocta-2,4,6-trienedial
-
-
-
-
?
antheraxathin + O2
?
-
-
-
-
?
beta-carotene + O2
beta-ionone + ?
-
-
-
-
?
delta-carotene + O2
alpha-ionone + 6-methyl-5-heptene-2-one + ?
-
-
-
-
?
epsilon-carotene + O2
2 alpha-ionone + ?
-
-
-
-
?
lycopene + O2
2 6-methyl-5-heptene-2-one + ?
-
-
-
-
?
neoxanthin + O2
?
-
-
-
-
?
phytoene + O2
2 geranylacetone + ?
-
-
-
-
?
violaxanthin + O2
?
-
-
-
-
?
zeaxanthin + O2
?
-
-
-
-
?
additional information
?
-
9-cis-10'-apo-beta-carotenal + 2 O2

carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
?
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
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
?
additional information

?
-
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
-
-
?
additional information
?
-
CCD8-dependent conversion of all-trans-10'-apo-beta-carotenal to 13-apo-beta-carotenone, reaction of EC 1.13.11.70
-
-
?
additional information
?
-
-
enzyme additionally catalyzes the conversion of 9-cis-10'-apo-beta-carotenal to carlactone and (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal, EC 1.13.11.69. The formation of carlactone is about 10fold faster than the formation of 13-apo-beta-carotenone
-
-
?
additional information
?
-
-
the enzyme cleaves differentially structured carotenoids at 5, 6 (5', 6') and 9, 10 (9',10') positions, generating C8 (6-methyl-5-hepten-2-one) and C13 (geranylacetone, alpha-ionone, and beta-ionone) apocarotenoids
-
-
-
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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
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2

carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
?
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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
-
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
-
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

-
transgenic SlCCD8 knockout lines display an increased shoot branching, reduced plant height, increased number of nodes and excessive adventitious root development. Transgenic lines show a reproductive phenotypes such as smaller flowers, fruits, as well as fewer and smaller seeds per fruit. Infestation by Phelipanche ramosa is reduced by 90% in lines with a relatively mild reduction in strigolactone biosynthesis and secretion while arbuscular mycorrhizal symbiosis, apical dominance and fruit yield are only mildly affected
malfunction
the biochemical basis of the shoot branching phenotype is due to inhibition of enzyme CCD8
malfunction
-
an enzyme mutant has morphological changes that includes dwarfing, excessive shoot branching and adventitious root formation. In addition, strigolactone-deficient mutants show a significant reduction in parasite (Phelipanche aegyptiaca) infestation compared to non-mutated tomato plants. In the mutated lines, orobanchol content is significantly reduced but total carotenoids level and expression of genes related to carotenoid biosynthesis are increased, as compared to control plants
malfunction
-
enzymatic mutants show excess branching, which is suppressed by exogenously applied strigolactones. Phelipanche aegyptiaca infection is lower in the enzyme mutants than in wild type
malfunction
-
enzyme mutants have increased shoot branching, reduced plant height, increased number of leaves and nodes, and reduced total plant biomass compared to wild type plants, however, the root-to-shoot ratio is unchanged. Enzyme mutations affect root morphology and affect plant senescence
malfunction
-
enzyme silencing favors phosphorus retention in the root and reduces phosphorus and biomass accumulation in the shoot under low phosphate
malfunction
enzyme-knockout lines show enhanced caulonema growth and enhanced susceptibility to fungal infection
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
metabolism
-
key enzymes in the biosynthesis of strigolactone
physiological function

-
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
gene disruption mutant reveals a modest increase in branching that contrasts with prominent pleiotropic changes that include marked reduction in stem diameter, reduced elongation of internodes, independent of carbon supply, and a pronounced delay in development of the centrally important, nodal system of adventitious roots