Sesquiterpene-like inhibitors of a 9-cis-epoxycarotenoid dioxygenase regulating abscisic acid biosynthesis in higher plants

Boyd, Jason; Gai, Ying; Nelson, Ken M.; Lukiwski, Erica; Talbot, James; Owen, Stacey J.; Zaharia, L. Irina; Cutler, Adrian J.; Abrams, Suzanne R.; Loewen, Michèle C.

doi:10.1016/j.bmc.2009.01.076

Cited by 24 publications

(18 citation statements)

References 41 publications

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“…These inhibitors were designed based on the structures of NCED substrates (Table 1; corresponding to the cleavage site of the NCED substrate. Computational docking to AtNCED3 constructed by homology modeling based on the crystal structure of the fungal homologue supports a mechanism of inhibition through the coordination of a heteroatom with a non-heme iron in the enzyme activation sites (Boyd et al 2009). Computational docking simulation of the enzyme and the compound should also be useful for screening enzyme inhibitors since the structure of enzymes and their inhibitors can be predicted using virtual chemical libraries without chemical synthesis.…”

Section: Aba Biosynthesis Inhibitorsmentioning

confidence: 98%

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Chemical biology of abscisic acid

Kitahata

Asami

2011

J Plant Res

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Chemical biology is a discipline that utilizes chemicals to elucidate biological mechanisms and physiological functions. Various abscisic acid (ABA) derivatives have revealed the structural requirement for the perception by ABA receptors while biotin or caged derivatives of ABA have disclosed the localization of several ABA-binding proteins. Recently, selective ABA agonist has been used to identify ABA receptors. Furthermore, ABA biosynthesis and catabolic inhibitors have contributed to the identification of new ABA functions in plant growth and development. The physiological function of ABA in non-plant organisms has gradually been revealed. In this review, we discuss the development of small bioactive chemicals and their significance in ABA research.

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Section: Aba Biosynthesis Inhibitorsmentioning

confidence: 98%

“…Boyd et al 2009). These sesquiterpene-like inhibitors possess a nitrogen or sulfur atom at the position…”

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confidence: 93%

Chemical biology of abscisic acid

Kitahata

Asami

2011

J Plant Res

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“…Hydroxamic acid analogs (9; Figure 3A ), which were designed based on the structures of abamine (6) and abamineSG (7), inhibited the activities of many CCDs, including AtCCD7, and increased the number of branches in inhibitor-treated Arabidopsis at a concentration of 100 μM (Sergeant et al, 2009). Similarly, sesquiterpene-like inhibitors of NCED (10; Figure 3A ) have been designed based on the structure of abamine (6; Boyd et al, 2009). Therefore, abamine (6) can be used as a scaffold for designing new inhibitors targeting several types of CCDs, including CCD7 and CCD8, and CCDs may be good targets for designing and developing specific inhibitors of SL biosynthesis.…”

Section: Sl Biosynthesis Inhibitorsmentioning

confidence: 99%

Target sites for chemical regulation of strigolactone signaling

Nakamura

Asami

2014

Front. Plant Sci.

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Demands for plant growth regulators (PGRs; chemicals that control plant growth) are increasing globally, especially in developing countries. Both positive and negative PGRs are widely used to enhance crop production and to suppress unwanted shoot growth, respectively. Strigolactones (SLs) are multifunctional molecules that function as phytohormones, inhibiting shoot branching and also functioning in the rhizospheric communication with symbiotic fungi and parasitic weeds. Therefore, it is anticipated that chemicals that regulate the functions of SLs will be widely used in agricultural applications. Although the SL biosynthetic pathway is not fully understood, it has been demonstrated that β-carotene isomerases, carotenoid cleavage dioxygenases (CCDs), and a cytochrome P450 monooxygenase are involved in strigolactone biosynthesis. A CCD inhibitor, abamine, which is also an inhibitor of abscisic acid biosynthesis, reduces the levels of SL in several plant species and reduces the germination rate of Orobanche minor seeds grown with tobacco. On the basis of the structure of abamine, several chemicals have been designed to specifically inhibit CCDs during SL synthesis. Cytochrome P450 monooxygenase is another target enzyme in the development of SL biosynthesis inhibitors, and the triazole-derived TIS series of chemicals is known to include SL biosynthesis inhibitors, although their target enzyme has not been identified. Recently, DWARF14 (D14) has been shown to be a receptor for SLs, and the D-ring moiety of SL is essential for its recognition by D14. A variety of SL agonists are currently under development and most agonists commonly contain the D-ring or a D-ring-like moiety. Several research groups have also resolved the crystal structure of D14 in the last two years. It is expected that this information on the D14 structure will be invaluable not only for developing SL agonists with novel structures but also in the design of inhibitors of SL receptors.

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“…Likewise, sesquiterpene-like inhibitors of an NCED have been designed based on the structure of abamine, as reported by Boyd et al 25) (Fig. 5).…”

Section: )mentioning

confidence: 99%

Abamine as a basis for new designs of regulators of strigolactone production

et al. 2011

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Nine-cis-epoxycarotenoid dioxygenase (NCED), belonging to the family of carotenoid-cleaving dioxygenases (CCDs), is the ratelimiting step in the abscisic acid (ABA) biosynthetic pathway in plants. Abamine is the first reported abscisic acid biosynthesis inhibitor to target NCED. Its utility has also been considered in the inhibition of other enzymes. As CCDs other than NCED are also involved in the strigolactone biosynthetic pathway, abamine may affect strigolactone biosynthesis. In this study, we found that abamine decreases the level of strigolactones in several plant species and reduces the germination rate of Orobanche minor seeds co-grown with tobacco. Taken together, these data suggest that abamine may be used as a scaffold for the development of specific regulators of strigolactone production.

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Sesquiterpene-like inhibitors of a 9-cis-epoxycarotenoid dioxygenase regulating abscisic acid biosynthesis in higher plants

Cited by 24 publications

References 41 publications

Chemical biology of abscisic acid

Chemical biology of abscisic acid

Target sites for chemical regulation of strigolactone signaling

Abamine as a basis for new designs of regulators of strigolactone production

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