Structure-function relations of strigolactone analogs: Activity as plant hormones and plant interactions

Molecular Plant

Volumn 6, Issue 1, 2013, Pages 141-152

  Cohen, Maja ^a,b   Prandi, Cristina ^c   Occhiato, Ernesto G ^d   Tabasso, Silvia ^c   Wininger, Smadar ^a   Resnick, Nathalie ^a   Steinberger, Yosef ^b   Koltai, Hinanit ^a   Kapulnik, Yoram ^a  

^a VOLCANI CENTER   (Israel)

^b BAR ILAN UNIVERSITY   (Israel)

^c UNIVERSITY OF TURIN   (Italy)

^d UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAZOLE DERIVATIVE; GAMMA BUTYROLACTONE; PHYTOHORMONE;

ANALOGS AND DERIVATIVES; ARABIDOPSIS; CHEMISTRY; DRUG EFFECTS; FUNGUS HYPHAE; GERMINATION; GROWTH, DEVELOPMENT AND AGING; METABOLISM; MYCORRHIZA; OROBANCHE; PHYSIOLOGY; PLANT SEED; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

4-BUTYROLACTONE; ARABIDOPSIS; CARBAZOLES; GERMINATION; HYPHAE; MYCORRHIZAE; OROBANCHE; PLANT GROWTH REGULATORS; SEEDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84875715344     PISSN: 16742052     EISSN: 17529867     Source Type: Journal    
DOI: 10.1093/mp/sss134     Document Type: Article

References (48)

1. Akiyama, K. (2007). Chemical identification and functional analysis of apocarotenoids involved in the development of arbuscular mycorrhizal symbiosis. Biosci. Biotechnol. Biochem. 71, 1405-1414.
2. Akiyama, K., Matsuzaki, K., and Hayashi, H. (2005). Plant sesquiterpenes induce hyphal branching in arbuscular mycorrhizal fungi. Nature. 435, 824-827.
3. Akiyama, K., Ogasawara, S., Ito, S., and Hayashi, H. (2010). Structural requirements of strigolactones for hyphal branching in AM fungi. Plant Cell Physiol. 51, 1104-1117.
4. Arite, T., Umehara, M., Ishikawa, S., Hanada, A., Maekawa, M., Yamaguchi, S., and Kyozuka, J. (2009). d14, a strigolactoneinsensitive mutant of rice, shows an accelerated outgrowth of tillers. Plant Cell Physiol. 50, 1416-1424.
5. Besserer, A., Bécard, G., Jauneau, A., Roux, C., and Séjalon-Delmas, N. (2008). GR24, a synthetic analog of strigolactones, stimulates the mitosis and growth of the arbuscular mycorrhizal fungus Gigaspora rosea by boosting its energy metabolism. Plant Physiol. 148, 402-413.
6. Besserer, A., Puech-Pages, V., Kiefer, P., Gomez-Roldan, V., Jauneau, A., Roy, S., Portais, J.C., Roux, C., Becard, G., and Sejalon- Delmas, N. (2006). Strigolactones stimulate arbuscular mycorrhizal fungi by activating mitochondria. PLoS Biol. 4, 1239-1247.
7. Beveridge, C.A., Ross, J.J., and Murfet, I.C. (1996). Branching in pea (action of genes Rms3 and Rms4). Plant Physiol. 110, 859-865.
8. Bhattacharya, C., Bonfante, P., Deagostino, A., Kapulnik, Y., Larini, P., Occhiato, E., Prandi, C., and Venturello, P. (2009). A new class of heterocyclic strigolactone analogues with fluorescent properties: synthesis and biological activity. Org. Biomol. Chem. 7, 3413-3420.
9. Boyer, F.D., Saint Germain, A., Pillot, J.P., Pouvreau, J.B., Xiao Chen, V., Ramos, S., Stevenin, A., Simier, P., Delavault, P., Beau, J.M., et al. (2012). Structure-activity relationship studies of strigolactonerelated molecules for branching inhibition in garden pea: molecule design for shoot branching. Plant Physiol. 159, 1524-1544.
10. Butler, L.G. (1995). Chemical communication between the parasitic weed Striga and its crop host: a new dimension in allelochemistry. Allelopathie. 12, 158-166.
11. Cook, C.E., Whichard, L.P., Turner, B., Wall, M.E., and Egley, G.H. (1966). Germination of witchweed (Striga lutea Lour.): isolation and properties of a potent stimulant. Science. 154, 1189-1190.
12. Cook, C.E., Whichard, L.P., Wall, M.E., Egley, G.H., and Coggon, P. (1972). Germination stimulants. II. The structure of strigol-a potent seed germination stimulant for witchweed (Striga lutea Lour.). J. Am. Chem. Soc. 94, 6198-6199.
13. Dun, E.A., Brewer, P.B., and Beveridge, C.A. (2009). Strigolactones: discovery of the elusive shoot branching hormone. Trends Plant Sci. 14, 364-372.
14. Fernandez-Aparicio, M., Flores, F., and Rubiales, D. (2009). Recognition of root exudates by seeds of broomrape (Orobanche and Phelipanche) species. Annals of Botany. 103, 423-431.
15. Gomez-Roldan, V., Fermas, S., Brewer, P.B., Puech-Pagès, V., and Dun, E.A. (2008). Strigolactone inhibition of shoot branching. Nature. 455, 189-194.
16. Hamiaux, C., Drummond, R.S.M., Janssen, B.J., Ledger, S.E., Cooney, J.M., Newcomb, R.D., and Snowden, K.C. (2012). DAD2 is an α/β hydrolase likely to be involved in the perception of the plant branching hormone, strigolactone. Curr. Biol. 22, 2032-2036.
17. Hauck, C., Müller, S., and Schildknecht, H. (1992). A germination stimulant for parasitic flowering plants from Sorghum bicolor, a genuine host plant. J. Plant Physiol. 139, 474-478.
18. Ishikawa, S., Maekawa, M., Arite, T., Onishi, K., Takamure, I., and Kyozuka, J. (2005). Suppression of tiller bud activity in tillering dwarf mutants of rice. Plant Cell Physiol. 46, 79-86.
19. Johnson, A.W., Gowda, G., Hassanali, A., Knox, J., Monaco, S., Razavi, Z., and Rosebery G. (1981). The preparation of synthetic analogues of strigol. J. Chem. Soc. Perkin Trans. 1, 1734-1743.
20. Johnson, A.W., Rosebery, G., and Parker, C. (1976). A novel approach to Striga and Orobanche control using synthetic germination stimulants. Weed Res. 16, 223-227.
21. Kapulnik, Y., Delaux, P.M., Resnick, N., Mayzlish-Gati, E., Wininger, S., Bhattacharya, C., Séjalon-Delmas, N., Combier, J.P., Bécard, G., and Belausov, E. (2011). Strigolactones affect lateral root formation and RH elongation in Arabidopsis. Planta. 233, 209-216.
22. Kim, H.I., Xie, X., Kim, H.S., Chul, C.J., Yoneyama, K., and Nomura, T. (2010). Structure-activity relationship of naturally occurring strigolactones in Orobanche minor seed germination stimulation. J. Pestic. Sci. 35, 344-347.
23. Kohlen, W., Charnikhova, T., Liu, Q., Bours, R., Domagalska, M.A., Beguerie, S., Verstappen, F., Leyser, O., Bouwmeester, H., and Ruyter-Spira, C. (2011). Strigolactones are transported through the xylem and play a key role in shoot architectural response to phosphate deficiency in nonarbuscular mycorrhizal host Arabidopsis. Plant Physiol. 155, 974-987.
24. Koltai, H. (2011). Strigolactones are regulators of root development. New Phytol. 190, 545-549.
25. Koltai, H., Dor, E., Hershenhorn, J., Joel, D., and Weininger, S. (2010). Strigolactones' effect on root growth and root-hair elongation may be mediated by auxin-efflux carriers. J. Plant Growth Regul. 29, 129-136.
26. Kondo, Y., Tadokoro, E., Matsuura, M., Iwasaki, K., and Sugimoto, Y. (2007). Synthesis and seed germination stimulating activity of some imino analogs of strigolactones. Biosci. Biotechnol. Biochem. 71, 2781-2786.
27. López-Rodríguez, M.L., Benhamú, B., Morcillo, M.J., Murcia, M., Viso, A., Alvaro, E., Campillo, M., and Pardo, L. (2003). The recognition of the voluminous substituent attached to the basic amino group of 5-HT4 receptor antagonists J. Computer-Aided Mol. Design. 17, 515-524.
28. López-Rodríguez, M.L., Benhamú, B., Morcillo, M.J., Murcia, M., Viso, A., Campillo, M., and Pardo, L. (2002). 5-HT4 receptor antagonists: structure-affinity relationships and ligand- receptor interactions. Curr. Top. Med. Chem. 2, 625-641.
29. Mangnus, E.M., and Zwanenburg, B. (1992). Tentative molecular mechanism for germination stimulation of Striga and Orobanche seeds by strigol and its synthetic analogs. J. Agric. Food Chem. 40, 1066-1070.
30. Matusova, R., Rani, K., Verstappen, F.W., Franssen, M.C., Beale, M.H., and Bouwmeester, H.J. (2005). The strigolactone germination stimulants of the plant-parasitic Striga and Orobanche spp. are derived from the carotenoid pathway. Plant Physiol. 139, 920-934.
31. Matusova, R., Van Mourik, T., and Bouwmeester, H.J. (2004). Changes in the sensitivity of parasitic weed seeds to germination stimulants. Seed Sci. Res. 14, 335-344.
32. Mishra, R., Jha, K.K., Kumar, S., and Tomer, I. (2011). Synthesis, properties and biological activity of thiophene: a review. Der Pharma Chemica. 3, 38-54.
33. Müller, S., Hauck, C., and Schildknecht, H. (1992). Germination stimulants produced by Vigna unguiculata Walp cv Saunders Upright. J. Plant Growth Regul. 11, 77-84.
34. Prandi, C., Occhiato, E., Tabasso, S., Bonfante, P., Novero, M., Scarpi, D., Bova, M., and Miletto, I. (2011). New potent fluorescent analogues of strigolactones: synthesis and biological activity in parasitic weed germination and fungal branching chemistry. Eur. J. Org. Chem. 21, 3781-3793.
35. Reizelman, A., Wigchert, S.C.M., del-Bianco, C., and Zwanenburg, B. (2003). Synthesis and bioactivity of labelled germination stimulants for the isolation and identification of the strigolactone receptor. Org. Biomol. Chem. 1, 950-959.
36. Ruyter-Spira, C., Kohlen, W., Charnikhova, T., van Zeijl, A., van Bezouwen, L., de Ruijter, N., Cardoso, C., Lopez-Raez, J.A., Matusova, R., and Bours, R. (2011). Physiological effects of the synthetic strigolactone analog GR24 on root system architecture in Arabidopsis: another below-ground role for strigolactones? Plant Physiol. 155, 721-734.
37. Scaffidi, A., Waters, M.T., Bond, C. S., Dixon, K.W., Smith, S.M., Ghisalberti, E.L., and Flematti, G.R. (2012). Exploring the molecular mechanism of karrikins and strigolactones Bioorg. Med. Chem. Lett. 22, 3743-3746.
38. Stirnberg, P., Furner, I.J., and Leyser, O. (2007). MAX2 participates in an SCF complex which acts locally at the node to suppress shoot branching. Plant J. 50, 80-94.
39. Stirnberg, P., Van De Sande, K., and Leyser, O. (2002). MAX1 and MAX2 control shoot lateral branching in Arabidopsis. Development. 129, 1131-1141.
40. Thuring, J., Keltjens, R., Nefkens, G.H.L., and Zwanenburg, B. (1997). Synthesis and biological evaluation of potential substrates for the isolation of the strigol receptor. Journal of the Chemical Society-Perkin Transactions. 1, 759-765.
41. Umehara, M., Hanada, A., Yoshida, S., Akiyama, K., and Arite T. (2008). Inhibition of shoot branching by new terpenoid plant hormones. Nature. 455, 195-200.
42. Waters, M.T., Nelson, D.C., Scaffidi, A., Flematti, G.R., and Sun, Y.M. (2012). Specialisation within the Dwarf14 protein family confers distinct responses to karrikins and strigolactones in Arabidopsis. Development. 139, 1285-1295.
43. Weyers, J.D.B., Paterson, N.W., and A'Brook, R. (1987). Toward a quantitative definition of plant hormone sensitivity. Plant Cell Environ. 10, 1-10.
44. Wigchert, S.C.M., Kuiper, E., Boelhouwer, G.J., Nefkens, G.H.L., Verkleij, J.A.C., and Zwanenburg, B. (1999). Dose-response of seeds of the parasitic weeds Striga and Orobanche toward the synthetic germination stimulants GR 24 and Nijmegen 1. J. Agric. Food Chem. 47, 1705-1710.
45. Xie, X., Yoneyama, K., and Yoneyama, K. (2010). The strigolactone story. Phytopathology. 48, 93-117.
46. Xie, X., Yoneyama, K., Kusumoto, D., Yamada, Y., Yokota, T., Takeuchi, Y., and Yoneyama, K. (2008). Isolation and identification of alectrol as (+)-orobanchyl acetate, a germination stimulant for root parasitic plants. Phytochemistry. 69, 427-431.
47. Zwanenburg, B., and Mwakaboko, A.S. (2011). Strigolactone analogues and mimics derived from phthalimide, saccharine, p-tolylmalondialdehyde, benzoic and salicylic acid as scaffolds. Bioorganic and Medicinal Chemistry. 19, 7394-7400.
48. Zwanenburg, B., Mwakaboko, A.S., Reizelman, A., Anilkumar, G., and Sethumadhavan, D. (2009). Structure and function of natural and synthetic signaling molecules in parasitic weed germination. Pest Manage. Sci. 65, 478-491.