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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
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
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
reduction of enzyme expression by RNAi correlates with an increase in branch development and delayed senescence
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
physiological function
-
the carotenoid cleavage dioxygenase 8, CCD8, catalyzes a series of reactions and molecular rearrangements for biosynthesis of strigolactones, a class of phytohormones synthesized from carotenoids via carlactone. The complex structure of carlactone is not easily deducible from its precursor 9-cis-beta-apo-10'-carotenal, a cis-configured beta-carotene cleavage product. Carlactone and (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal, and reaction intermediates structure analysis by LC-MS and NMR, overview
physiological function
isoform CCD8a is involved in bulbil outgrowth
physiological function
isoform CCD8b is involved in bulbil outgrowth
physiological function
-
the enzyme facilitates plant tolerance to phosphate limitation
physiological function
-
the enzyme plays an important role in the development of branches and inhibits the growth of axillary buds by up-regulating its downstream gene, BRC1
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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)
-
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
Ledger, S.E.; Janssen, B.J.; Karunairetnam, S.; Wang, T.; Snowden, K.C.
Modified CAROTENOID CLEAVAGE DIOXYGENASE8 expression correlates with altered branching in kiwifruit (Actinidia chinensis)
New Phytol.
188
803-813
2010
Actinidia chinensis (E3T3A2)
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
Guan, J.C.; Koch, K.E.; Suzuki, M.; Wu, S.; Latshaw, S.; Petruff, T.; Goulet, C.; Klee, H.J.; McCarty, D.R.
Diverse roles of strigolactone signaling in maize architecture and the uncoupling of a branching-specific subnetwork
Plant Physiol.
160
1303-1317
2012
Zea mays (C4PJN4), Zea mays
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
Pisum sativum, Arabidopsis thaliana (Q8VY26)
brenda
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