Structure-activity relationship studies of flavonol analogues on pollen germination

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 10, 2014, Pages 2175-2181

  Forbes, Alaina M ^a   Meier, G Patrick ^a   Haendiges, Stacey ^a   Taylor, Loverine P ^a  

^a WASHINGTON STATE UNIVERSITY   (United States)

Author keywords

agonist; antagonist; conditionally male infertile; flavonoids; flavonols; hydrogen bonding; hydrophilic; hydrophobic; kaempferol; pollen germination sequence; steric hindrance; structure activity relationship; Suzuki Miyaura cross coupling

Indexed keywords

CHEMICAL REACTIONS; CULTIVATION; HYDROGEN BONDS; HYDROPHOBICITY; PLANTS (BOTANY); STRUCTURES (BUILT OBJECTS); CHEMICAL ACTIVATION; HYDROGEN; POLYPHENOLIC COMPOUNDS;

AGONIST; ANTAGONIST; CONDITIONALLY MALE INFERTILE; FLAVONOLS; HYDROPHILIC; HYDROPHOBIC; KAEMPFEROL; POLLEN GERMINATION; STERIC HINDRANCES; STRUCTURE ACTIVITY RELATIONSHIPS; SUZUKI-MIYAURA CROSS-COUPLING;

FLAVONOIDS;

FLAVONOID; FLAVONOL DERIVATIVE; GALANGIN; KAEMPFERIDE; KAEMPFEROL; KAEMPFEROL DERIVATIVE;

ARTICLE; CHEMISTRY; DRUG EFFECT; DRUG POTENTIATION; GENETICS; GERMINATION; HYDROGEN BOND; PETUNIA; PHYSIOLOGY; POLLEN; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TRANSGENIC PLANT;

CHEMISTRY TECHNIQUES, SYNTHETIC; FLAVONOIDS; FLAVONOLS; GERMINATION; HYDROGEN BONDING; KAEMPFEROLS; PETUNIA; PLANTS, GENETICALLY MODIFIED; POLLEN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84896350590     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf405688d     Document Type: Article

References (36)

1. Middleton, E., Jr.; Kandaswami, C.; Theoharides, T. C. The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer Pharmacol. Rev. 2000, 52, 673-751
2. Taylor, L. P.; Grotewold, E. Flavonoids as developmental regulators Curr. Opin. Plant Biol. 2005, 8, 317-323
3. Solovchenko, A.; Merzlyak, M. Optical properties and contribution of cuticle to UV protection in plants: experiments with apple fruit Photochem. Photobiol. Sci. 2003, 2, 861-866
4. Smith, G. J.; Markham, R. K. Tautomerism of flavonol glucosides: relevance to plant UV protection and flower color J. Photochem. Photobiol. 1998, 118, 99-105
5. Vogt, T.; Pollak, P.; Tarlyn, N.; Taylor, L. P. Pollination-or wound-induced kaempferol accumulation in petunia stigmas enhances seed production Plant Cell 1994, 6, 11-23
6. Pollak, P. E.; Vogt, T.; Mo, Y.; Taylor, L. P. Chalcone synthase and flavonol accumulation in stigmas and anthers of petunia hybrida Plant Physiol. 1993, 102, 925-932
7. Taylor, L. P.; Hepler, P. K. Pollen germination and tube growth Annu. Rev. Plant Physiol. Plant Mol. Biol. 1997, 48, 461-491
8. Neera Garg, G. Symbiotic nitrogen fixation in legume nodules: process and signaling Agron. Sustain. Dev. 2007, 27, 59-68
9. Shaw, L. J.; Morris, P.; Hooker, J. E. Perception and modification of plant flavonoid signals by rhizosphere microorganisms Environ. Microbiol. 2006, 8, 1867-1880
10. Harborne, J. B. The Flavonoids: Advances in Research since 1980; Chapman and Hall: New York, 1988.
11. Vogt, T.; Wollenweber, E.; Taylor, L. P. The structural requirements of flavonols that induce pollen germination of conditionally male fertile petunia Phytochemistry 1995, 38, 589-592
12. Mo, Y.; Nagel, C.; Taylor, L. P. Biochemical complementation of chalcone synthase mutants defines a role of flavonols in functional pollen Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 7213-7217
13. Schijlen, E. G.; de Vos, C. H.; Martens, S.; Jonker, H. H.; Rosin, F. M.; Molthoff, J. W.; Tikunov, Y. M.; Angenent, G. C.; van Tunen, A. J.; Bovy, A. G. RNA interference silencing of chalcone synthase, the first step in the flavonoid biosynthesis pathway, leads to parthenocarpic tomato fruits Plant Physiol. 2007, 144, 1520-1530
14. Dumont-BeBoux, N.; von Aderkas, P. In vitro pollen tube growth in Douglas-fir Can. J. For. Res. 1997, 27, 674-678
15. Ylstra, B.; Touraev, A.; Moreno, R. M.; Stoger, E.; van Tunen, A. J.; Vicente, O.; Mol, J. N.; Heberle-Bors, E. Flavonols stimulate development, germination, and tube growth of tobacco pollen Plant Physiol. 1992, 100, 902-907
16. Mahajan, M.; Ahuja, P. S.; Yadav, S. K. Post-transcriptional silencing of flavonol synthase mRNA in tobacco leads to fruits with arrested seed set PLoS One 2011, 6, e28315
17. Yin, R.; Messner, B.; Faus-Kessler, T.; Hoffmann, T.; Schwab, W.; Hajirezaei, M. R.; von Saint Paul, V.; Heller, W.; Schaffner, A. R. Feedback inhibition of general phenylpropanoid and flavonol biosynthesis pathways upon a compromised flavonol-3-O-glycosylation J. Exp. Bot. 2012, 63, 2465-2478
18. Thompson, E. P.; Wilkins, C.; Demidchik, V.; Davies, J. M.; Glover, B. J. An Arabidopsis flavonoid transporter is required for anther dehiscence and pollen development J. Exp. Bot. 2010, 61, 439-451
19. Jia, L.; Wu, Q.; Ye, N.; Liu, R.; Shi, L.; Xu, W.; Zhi, H.; Rahman, A. N.; Xia, Y.; Zhang, J. Proanthocyanidins inhibits seed germination by maintaining a high level of abscisic acid in Arabidopsis thaliana J. Integr. Plant Biol. 2012, 54, 663-673
20. Muir, S. R.; Collins, G. J.; Robinson, S.; Hughes, S.; Bovy, A.; Ric De Vos, C. H.; van Tunen, A. J.; Verhoeyen, M. E. Overexpression of petunia chalcone isomerase in tomato results in fruit containing increased levels of flavonols Nat. Biotechnol. 2001, 19, 470-474
21. Charkraborty, K.; Devakumar, C. Ethyloxanilates as specific male gametocides for wheat (Triticum aestivum L.) Plant Breed. 2006, 125, 441-447
22. Charkraborty, K.; Devakumar, C. N -Acylanilines, herbicide-CHA chimera, and amino acid analogues as novel chemical hybridizing agents for wheat (Triticum aestivum L.) J. Agric. Food Chem. 2005, 53, 7899-7907
23. Cheng, S. H.; Zhuang, J. Y.; Fan, Y. Y.; Du, J. H.; Cao, L. Y. Progress in research and development on hybrid rice: a super-domesticate in China Ann. Bot. 2007, 100, 959-966
24. Tanaka, H.; Stohlmeyer, M. M.; Wandless, T. J.; Taylor, L. P. Synthesis of flavonol derivatives as probes of biological processes Tetrahedron Lett. 2000, 41, 9735-9739
25. Boumendjel, A.; Bois, F.; Beney, C.; Mariotte, A. M.; Conseil, G.; Di Pietro, A. B-ring substituted 5,7-dihydroxyflavonols with high-affinity binding to P-glycoprotein responsible for cell multidrug resistance Bioorg. Med. Chem. Lett. 2001, 11, 75-77
26. Azimova, S. S.; Vinogradova, V. I. G. Natural Compounds: Flavonoids: Plant Sources, Structure and Properties; Springer: New York, 2013; pp 96.
27. Batirov, E. K.; Kiyamitdinova, F.; Malikov, V. M. Flavonoids of the epigeal part of Glycyrrhiza glabra Chem. Nat. Compd. 1986, 22, 107-108
28. Yuldashev, M. P. Flavonoids of the epigeal part of Glycyrrhiza uralensis Chem. Nat. Compd. 1998, 34, 508-509
29. 13C NMR spectroscopy of flavonoids Heterocycles 1981, 16, 2181
30. Molander, G. A.; Biolatto, B. Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of potassium aryl-and heteroaryltrifluoroborates J. Org. Chem. 2003, 68, 4302-4314
31. Taylor, L. P.; Jorgenson, R. Conditional male fertility in chalcone synthase-deficient petunia J. Hered. 1992, 83, 11-17
32. Ichikawa, M.; Pamukcu, A. M.; Bryan, G. T. A convenient method for the synthesis of kaempferol Org. Prep. Proc. Int. 1982, 14, 183-187
33. 2 receptors J. Med. Chem. 1991, 34, 1511-1514
34. Newman, M. S.; Sankaran, V.; Olson, D. R. Phenolic and ketonic tautomers in polycyclic aromatic hydrocarbons J. Am. Chem. Soc. 1976, 98, 3237-3242
35. Landini, D.; Montanari, F.; Rolla, F. Cleavage of dialkyl and aryl alkyl ethers with hydrobromic acid in the presence of phase-transfer catalysts Synthesis 1978, 10, 771-773
36. Taylor, L. P.; Miller, K. D. The use of a photoactivatable kaempferol analogue to probe the role of flavonol 3-O -galactosyltransferase in pollen germination Adv. Exp. Med. Biol. 2002, 505, 41-50