Takahashi I

References (14)

Title : New Series of Zaxinone Mimics (MiZax) for Fundamental and Applied Research - Jamil_2023_Biomolecules_13_
Author(s) : Jamil M , Lin PY , Berqdar L , Wang JY , Takahashi I , Ota T , Alhammad N , Chen GE , Asami T , Al-Babili S
Ref : Biomolecules , 13 : , 2023
Abstract : The apocarotenoid zaxinone is a recently discovered regulatory metabolite required for proper rice growth and development. In addition, zaxinone and its two mimics (MiZax3 and MiZax5) were shown to have a remarkable growth-promoting activity on crops and a capability to reduce infestation by the root parasitic plant Striga through decreasing strigolactone (SL) production, suggesting their potential for application in agriculture and horticulture. In the present study, we developed a new series of MiZax via structural modification of the two potent zaxinone mimics (MiZax3 and MiZax5) and evaluated their effect on plant growth and Striga infestation. In general, the structural modifications to MiZax3 and MiZax5 did not additionally improve their overall performance but caused an increase in certain activities. In conclusion, MiZax5 and especially MiZax3 remain the likely most efficient zaxinone mimics for controlling Striga infestation.
ESTHER : Jamil_2023_Biomolecules_13_
PubMedSearch : Jamil_2023_Biomolecules_13_
PubMedID: 37627271

Title : Synthesis of Carlactone Derivatives to Develop a Novel Inhibitor of Strigolactone Biosynthesis - Kawada_2023_ACS.Omega_8_13855
Author(s) : Kawada K , Saito T , Onoda S , Inayama T , Takahashi I , Seto Y , Nomura T , Sasaki Y , Asami T , Yajima S , Ito S
Ref : ACS Omega , 8 :13855 , 2023
Abstract : Strigolactones (SLs), phytohormones that inhibit shoot branching in plants, promote the germination of root-parasitic plants, such as Striga spp. and Orobanche spp., which drastically reduces the crop yield. Therefore, reducing SL production via chemical treatment may increase the crop yield. To design specific inhibitors, it is valid to utilize the substrate structure of the target proteins as lead compounds. In this study, we focused on Os900, a rice enzyme that oxidizes the SL precursor carlactone (CL) to 4-deoxyorobanchol (4DO), and synthesized 10 CL derivatives. The effects of the synthesized CL derivatives on SL biosynthesis were evaluated by the Os900 enzyme assay in vitro and by measuring 4DO levels in rice root exudates. We identified some CL derivatives that inhibited SL biosynthesis in vitro and in vivo.
ESTHER : Kawada_2023_ACS.Omega_8_13855
PubMedSearch : Kawada_2023_ACS.Omega_8_13855
PubMedID: 37091382

Title : Function of hydroxycinnamoyl spermidines in seedling growth of Arabidopsis - Takahashi_2022_Biosci.Biotechnol.Biochem_86_294
Author(s) : Takahashi I , Ota T , Asami T
Ref : Biosci Biotechnol Biochem , 86 :294 , 2022
Abstract : Hydroxycinnamic acid amides are involved in various developmental processes as well as in biotic and abiotic stress responses. Among them, the presence of spermidine derivatives, such as N1,N8-di(coumaroyl)-spermidine and N1,N8-di(sinapoyl)-spermidine, and their biosynthetic genes have been reported in Arabidopsis, but their functions in plants are still unknown. We chemically synthesized the above-mentioned spermidine derivatives to assess their physiological functions in Arabidopsis. We evaluated the growth and development of chemically treated Arabidopsis and demonstrated that these compounds inhibited seed germination, hypocotyl elongation, and primary root growth, which could be due to modulation of plant hormone homeostasis and signaling. The results suggest that these compounds are regulatory metabolites that modulate plant growth and development.
ESTHER : Takahashi_2022_Biosci.Biotechnol.Biochem_86_294
PubMedSearch : Takahashi_2022_Biosci.Biotechnol.Biochem_86_294
PubMedID: 34958361

Title : Canonical strigolactones are not the major determinant of tillering but important rhizospheric signals in rice - Ito_2022_Sci.Adv_8_eadd1278
Author(s) : Ito S , Braguy J , Wang JY , Yoda A , Fiorilli V , Takahashi I , Jamil M , Felemban A , Miyazaki S , Mazzarella T , Chen GE , Shinozawa A , Balakrishna A , Berqdar L , Rajan C , Ali S , Haider I , Sasaki Y , Yajima S , Akiyama K , Lanfranco L , Zurbriggen MD , Nomura T , Asami T , Al-Babili S
Ref : Sci Adv , 8 :eadd1278 , 2022
Abstract : Strigolactones (SLs) are a plant hormone inhibiting shoot branching/tillering and a rhizospheric, chemical signal that triggers seed germination of the noxious root parasitic plant Striga and mediates symbiosis with beneficial arbuscular mycorrhizal fungi. Identifying specific roles of canonical and noncanonical SLs, the two SL subfamilies, is important for developing Striga-resistant cereals and for engineering plant architecture. Here, we report that rice mutants lacking canonical SLs do not show the shoot phenotypes known for SL-deficient plants, exhibiting only a delay in establishing arbuscular mycorrhizal symbiosis, but release exudates with a significantly decreased Striga seed-germinating activity. Blocking the biosynthesis of canonical SLs by TIS108, a specific enzyme inhibitor, significantly lowered Striga infestation without affecting rice growth. These results indicate that canonical SLs are not the determinant of shoot architecture and pave the way for increasing crop resistance by gene editing or chemical treatment.
ESTHER : Ito_2022_Sci.Adv_8_eadd1278
PubMedSearch : Ito_2022_Sci.Adv_8_eadd1278
PubMedID: 36322663

Title : On improving strigolactone mimics for induction of suicidal germination of the root parasitic plant Striga hermonthica - Takahashi_2021_aBIOTECH_2_1
Author(s) : Takahashi I , Fukui K , Asami T
Ref : aBIOTECH , 2 :1 , 2021
Abstract : Strigolactones (SLs) are plant hormones that regulate the branching of plants and seed germination stimulants of root parasitic plants. As root parasites are a great threat to agricultural production, the use of SL agonists could be anticipated to provide an efficient method for regulating root parasites as suicidal germination inducers. A series of phenoxyfuranone-type SL mimics, termed debranones, has been reported to show potent bioactivities, including reduction of the tiller number on rice, and stimulation of seed germination in the root parasite Striga hermonthica. To exert both activities, two substituents on the phenyl ring of the molecules were important but at least a substituent at the 2-position must be an electron-withdrawing group. However, little is known about the effect of the properties of the substituents at the 2-position on bioactivities. Here, we found that different substituents at the 2-position give different preferences for bioactivities. Halogenated debranones were more effective than the others and SL agonist GR24 for inhibiting rice tiller but far less effective in the induction of S. hermonthica germination. Meanwhile, nitrile and methyl derivatives clearly stimulated the germination of S. hermonthica seeds. Although their IC50 values were 100 times higher than that of GR24 in the receptor competitive binding assay, their physiological activities were approximately 1/10 of GR24. These differences could be due to their uptake in plants and/or their physicochemical stability under our experimental conditions. These findings could support the design of more potent and selective SL agonists that could contribute to solving big agricultural issues.
ESTHER : Takahashi_2021_aBIOTECH_2_1
PubMedSearch : Takahashi_2021_aBIOTECH_2_1

Title : Efficient Mimics for Elucidating Zaxinone Biology and Promoting Agricultural Applications - Wang_2020_Mol.Plant_13_1654
Author(s) : Wang JY , Jamil M , Lin PY , Ota T , Fiorilli V , Novero M , Zarban RA , Kountche BA , Takahashi I , Martinez C , Lanfranco L , Bonfante P , de Lera AR , Asami T , Al-Babili S
Ref : Mol Plant , 13 :1654 , 2020
Abstract : Zaxinone is an apocarotenoid regulatory metabolite required for normal rice growth and development. In addition, zaxinone has a large application potential in agriculture, due to its growth-promoting activity and capability to alleviate infestation by the root parasitic plant Striga through decreasing strigolactone (SL) production. However, zaxinone is poorly accessible to the scientific community because of its laborious organic synthesis that impedes its further investigation and utilization. In this study, we developed easy-to-synthesize and highly efficient mimics of zaxinone (MiZax). We performed a structure-activity relationship study using a series of apocarotenoids distinguished from zaxinone by different structural features. Using the obtained results, we designed several phenyl-based compounds synthesized with a high-yield through a simple method. Activity tests showed that MiZax3 and MiZax5 exert zaxinone activity in rescuing root growth of a zaxinone-deficient rice mutant, promoting growth, and reducing SL content in roots and root exudates of wild-type plants. Moreover, these compounds were at least as efficient as zaxinone in suppressing transcript level of SL biosynthesis genes and in alleviating Striga infestation under greenhouse conditions, and did not negatively impact mycorrhization. Taken together, MiZax are a promising tool for elucidating zaxinone biology and investigating rice development, and suitable candidates for combating Striga and increasing crop growth.
ESTHER : Wang_2020_Mol.Plant_13_1654
PubMedSearch : Wang_2020_Mol.Plant_13_1654
PubMedID: 32835886

Title : A New Series of Carlactonoic Acid Based Strigolactone Analogs for Fundamental and Applied Research - Jamil_2020_Front.Plant.Sci_11_434
Author(s) : Jamil M , Kountche BA , Wang JY , Haider I , Jia KP , Takahashi I , Ota T , Asami T , Al-Babili S
Ref : Front Plant Sci , 11 :434 , 2020
Abstract : Strigolactones (SLs) are a group of carotenoid derived plant hormones that play a key role in establishing plant architecture and adapting it to environmental changes, and are involved in plants response to biotic and abiotic stress. SLs are also released into the soil to serve as a chemical signal attracting beneficial mycorrhizal fungi. However, this signal also induces seed germination in root parasitic weeds that represent a major global threat for agriculture. This wide spectrum of biological functions has made SL research one of the most important current topics in fundamental and applied plant science. The availability of SLs is crucial for investigating SL biology as well as for agricultural application. However, natural SLs are produced in very low amounts, and their organic synthesis is quite difficult, which creates a need for efficient and easy-to-synthesize analogs and mimics. Recently, we have generated a set of SL analogs, Methyl Phenlactonoates (MPs), which resemble the non-canonical SL carlactonoic acid. In this paper, we describe the development and characterization of a new series of easy-to-synthesize MPs. The new analogs were assessed with respect to regulation of shoot branching, impact on leaf senescence, and induction of seed germination in different root parasitic plants species. Some of the new analogs showed higher efficiency in inhibiting shoot branching as well as in triggering parasitic seed germination, compared to the commonly used GR24. MP16 was the most outstanding analog showing high activity in different SL biological functions. In summary, our new analogs series contains very promising candidates for different applications, which include the usage in studies for understanding different aspects of SL biology as well as large scale field application for combating root parasitic weeds, such as Striga hermonthica that devastates cereal yields in sub-Saharan Africa.
ESTHER : Jamil_2020_Front.Plant.Sci_11_434
PubMedSearch : Jamil_2020_Front.Plant.Sci_11_434
PubMedID: 32373143

Title : Synthesis and Biological Evaluation of Novel Triazole Derivatives as Strigolactone Biosynthesis Inhibitors - Kawada_2019_J.Agric.Food.Chem_67_6143
Author(s) : Kawada K , Takahashi I , Arai M , Sasaki Y , Asami T , Yajima S , Ito S
Ref : Journal of Agricultural and Food Chemistry , 67 :6143 , 2019
Abstract : Strigolactones (SLs) are one of the plant hormones that control several important agronomic traits, such as shoot branching, leaf senescence, and stress tolerance. Manipulation of the SL biosynthesis can increase the crop yield. We previously reported that a triazole derivative, TIS108, inhibits SL biosynthesis. In this study, we synthesized a number of novel TIS108 derivatives. Structure-activity relationship studies revealed that 4-(2-phenoxyethoxy)-1-phenyl-2-(1 H-1,2,4-triazol-1-yl)butan-1-one (KK5) inhibits the level of 4-deoxyorobanchol in roots more strongly than TIS108. We further found that KK5-treated Arabidopsis showed increased branching phenotype with the upregulated gene expression of AtMAX3 and AtMAX4. These results indicate that KK5 is a specific SL biosynthesis inhibitor in rice and Arabidopsis.
ESTHER : Kawada_2019_J.Agric.Food.Chem_67_6143
PubMedSearch : Kawada_2019_J.Agric.Food.Chem_67_6143
PubMedID: 31083983

Title : Methylation at the C-3' in D-Ring of Strigolactone Analogs Reduces Biological Activity in Root Parasitic Plants and Rice - Jamil_2019_Front.Plant.Sci_10_353
Author(s) : Jamil M , Kountche BA , Haider I , Wang JY , Aldossary F , Zarban RA , Jia KP , Yonli D , Shahul Hameed UF , Takahashi I , Ota T , Arold ST , Asami T , Al-Babili S
Ref : Front Plant Sci , 10 :353 , 2019
Abstract : Strigolactones (SLs) regulate plant development and induce seed germination in obligate root parasitic weeds, e.g. Striga spp. Because organic synthesis of natural SLs is laborious, there is a large need for easy-to-synthesize and efficient analogs. Here, we investigated the effect of a structural modification of the D-ring, a conserved structural element in SLs. We synthesized and investigated the activity of two analogs, MP13 and MP26, which differ from previously published AR8 and AR36 only in the absence of methylation at C-3'. The de-methylated MP13 and MP26 were much more efficient in regulating plant development and inducing Striga seed germination, compared with AR8. Hydrolysis assays performed with purified Striga SL receptor and docking of AR8 and MP13 to the corresponding active site confirmed and explained the higher activity. Field trials performed in a naturally Striga-infested African farmer's field unraveled MP13 as a promising candidate for combating Striga by inducing germination in host's absence. Our findings demonstrate that methylation of the C-3' in D-ring in SL analogs has a negative impact on their activity and identify MP13 and, particularly, MP26 as potent SL analogs with simple structures, which can be employed to control Striga, a major threat to global food security.
ESTHER : Jamil_2019_Front.Plant.Sci_10_353
PubMedSearch : Jamil_2019_Front.Plant.Sci_10_353
PubMedID: 31001294

Title : Regulation of biosynthesis, perception, and functions of strigolactones for promoting arbuscular mycorrhizal symbiosis and managing root parasitic weeds - Yoneyama_2019_Pest.Manag.Sci_75_2353
Author(s) : Yoneyama K , Xie X , Nomura T , Takahashi I , Asami T , Mori N , Akiyama K , Kusajima M , Nakashita H
Ref : Pest Manag Sci , 75 :2353 , 2019
Abstract : Strigolactones (SLs) are carotenoid-derived plant secondary metabolites that play important roles in various aspects of plant growth and development as plant hormones, and in rhizosphere communications with symbiotic microbes and also root parasitic weeds. Therefore, sophisticated regulation of the biosynthesis, perception and functions of SLs is expected to promote symbiosis of beneficial microbes including arbuscular mycorrhizal (AM) fungi and also to retard parasitism by devastating root parasitic weeds. We have developed SL mimics with different skeletons, SL biosynthesis inhibitors acting at different biosynthetic steps, SL perception inhibitors that covalently bind to the SL receptor D14, and SL function inhibitors that bind to the serine residue at the catalytic site. In greenhouse pot tests, TIS108, an azole-type SL biosynthesis inhibitor effectively reduced numbers of attached root parasites Orobanche minor and Striga hermonthica without affecting their host plants; tomato and rice, respectively. AM colonization resulted in weak but distinctly enhanced plant resistance to pathogens. SL mimics can be used to promote AM symbiosis and to reduce the application rate of systemic-acquired resistance inducers which are generally phytotoxic to horticultural crops. (c) 2019 Society of Chemical Industry.
ESTHER : Yoneyama_2019_Pest.Manag.Sci_75_2353
PubMedSearch : Yoneyama_2019_Pest.Manag.Sci_75_2353
PubMedID: 30843315

Title : Triazole Ureas Covalently Bind to Strigolactone Receptor and Antagonize Strigolactone Responses - Nakamura_2019_Mol.Plant_12_44
Author(s) : Nakamura H , Hirabayashi K , Miyakawa T , Kikuzato K , Hu W , Xu Y , Jiang K , Takahashi I , Niiyama R , Dohmae N , Tanokura M , Asami T
Ref : Mol Plant , 12 :44 , 2019
Abstract : Strigolactones, a class of plant hormones with multiple functions, mediate plant-plant and plant-microorganism communications in the rhizosphere. In this study, we developed potent strigolactone antagonists, which covalently bind to the strigolactone receptor D14, by preparing an array of triazole urea compounds. Using yeast two-hybrid and rice-tillering assays, we identified a triazole urea compound KK094 as a potent inhibitor of strigolactone receptors. Liquid chromatography-tandem mass spectrometry analysis and X-ray crystallography revealed that KK094 was hydrolyzed by D14, and that a reaction product of this degradation covalently binds to the Ser residue of the catalytic triad of D14. Furthermore, we identified two triazole urea compounds KK052 and KK073, whose effects on D14-D53/D14-SLR1 complex formation were opposite due to the absence (KK052) or presence (KK073) of a trifluoromethyl group on their phenyl ring. These results demonstrate that triazole urea compounds are potentially powerful tools for agricultural application and may be useful for the elucidation of the complicated mechanism underlying strigolactone perception.
ESTHER : Nakamura_2019_Mol.Plant_12_44
PubMedSearch : Nakamura_2019_Mol.Plant_12_44
PubMedID: 30391752
Gene_locus related to this paper: orysj-Q10QA5

Title : Target-based selectivity of strigolactone agonists and antagonists in plants and their potential use in agriculture - Takahashi_2018_J.Exp.Bot_69_2241
Author(s) : Takahashi I , Asami T
Ref : J Exp Bot , 69 :2241 , 2018
Abstract : Strigolactones (SLs) are small carotenoid-derived molecules that possess a wide spectrum of functions, including plant hormonal activities and chemical mediation of rhizosphere communication with both root parasitic plants and symbiotic arbuscular mycorrhizal fungi. Chemicals that regulate the functions of SLs may therefore have the potential to become widely used in agricultural applications. For example, various SL analogs and mimics have been developed to reduce the seed banks of root parasites in the field. Other analogs and mimics act selectively to suppress branching, with weak, or no stimulation, of germination in root parasites. In addition, some antagonists for SL receptors have been developed based on the mechanisms of SL perception. A better understanding of the modes of action of SL perception by various receptors will help to support the design of SL analogs, mimics, and antagonists with high activity and selectivity. Here, we review the compounds reported so far from the viewpoint of their selectivity to their targets, and the possibilities for their use in agriculture.
ESTHER : Takahashi_2018_J.Exp.Bot_69_2241
PubMedSearch : Takahashi_2018_J.Exp.Bot_69_2241
PubMedID: 29635308

Title : Strigolactone-induced senescence of a bamboo leaf in the dark is alleviated by exogenous sugar - Tian_2018_J.Pestic.Sci_43_173
Author(s) : Tian MQ , Jiang K , Takahashi I , Li GD
Ref : J Pestic Sci , 43 :173 , 2018
Abstract : Strigolactones (SLs) are a series of sesquiterpene lactones that serve as plant hormones to regulate plant growth and development, such as shoot branching, lateral root formation, and root hair elongation. Recently, SLs have been reported to accelerate the leaf senescence, which is also regulated by sugar signals. In this study, we utilized segments of a bamboo leaf to observe leaf senescence and confirmed that SL accelerates leaf senescence and triggers cell death under a dark condition rather than under a light condition. Further studies showed that the co-treatment of sugars suppressed SL-induced leaf senescence and cell death under dark conditions, suggesting a crosstalk between SL and the sugar signal in regulating leaf senescence.
ESTHER : Tian_2018_J.Pestic.Sci_43_173
PubMedSearch : Tian_2018_J.Pestic.Sci_43_173
PubMedID: 30363134

Title : Chemical modification of a phenoxyfuranone-type strigolactone mimic for selective effects on rice tillering or Striga hermonthica seed germination - Takahashi_2016_Pest.Manag.Sci_72_2048
Author(s) : Takahashi I , Fukui K , Asami T
Ref : Pest Manag Sci , 72 :2048 , 2016
Abstract : BACKGROUND: We previously reported that a series of phenoxyfuranone compounds, designated 'debranones', mimic strigolactone (SL) activity. 4-Bromodebranone (4BD) is a functionally selective SL mimic that reduces the number of shoot branches on rice more potently than GR24, a typical synthetic SL analogue, but does not induce seed germination in the root-parasitic plant Striga hermonthica. To enhance the selective activity of debranones in stimulating the seed germination of root-parasitic plants, we prepared several analogues of 4BD in which the chlorine atom was substituted with an H atom at the o-, m- or p-position on the phenyl ring (designated 2-, 3-, or 4-chlorodebranone, respectively) or had a bicyclic group instead of the phenyl ring. We evaluated the biological activities of the compounds with rice tillering assays and S. hermonthica seed germination assays. RESULTS: Both assays showed that the substituent position affected debranone efficiency, and among the monochlorodebranones, 2-chlorodebranone was more effective than the other two isomers in both assays. When the activities of the bicyclic debranones were compared in the same two assays, one was more active than GR24 in the rice tillering assay. This debranone also stimulated the germination of S. hermonthica seeds. Thus, some debranone derivatives induced the germination of S. hermonthica seeds, although their activities were still approximately 1/20 that of GR24. CONCLUSION: These results strongly suggest that further and rigorous structure-activity relationship studies of the debranones will identify derivatives that more potently stimulate the suicidal germination of S. hermonthica seeds. (c) 2016 Society of Chemical Industry.
ESTHER : Takahashi_2016_Pest.Manag.Sci_72_2048
PubMedSearch : Takahashi_2016_Pest.Manag.Sci_72_2048
PubMedID: 26929041