Evolutionarily conserved phenylpropanoid pattern on angiosperm pollen

Trends in Plant Science

Volumn 20, Issue 4, 2015, Pages 212-218

  Fellenberg, Christin ^a,b   Vogt, Thomas ^a  

^a LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

^b UNIVERSITY OF VICTORIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EMBRYOPHYTA; MAGNOLIOPHYTA;

PHENYLALANINE;

ANGIOSPERM; EVOLUTION; METABOLISM; POLLEN;

ANGIOSPERMS; BIOLOGICAL EVOLUTION; PHENYLALANINE; POLLEN;

EID: 84926420411     PISSN: 13601385     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tplants.2015.01.011     Document Type: Review

References (50)

1. Weng J.K., Chapple C. The origin and evolution of lignin biosynthesis. New Phytol. 2010, 187:273-285.
2. Pichersky E., Lewinsohn E. Convergent evolution in plant specialized metabolism. Ann. Rev. Plant Biol. 2011, 62:549-566.
3. Tohge T., et al. The evolution of phenylpropanoid metabolism in the green lineage. Crit. Rev. Biochem. Mol. Biol. 2013, 48:123-152.
4. Mihayara T., et al. Acyl-glucose-dependent glucosyltransferase catalyzes the final step of anthocyanin formation in Arabidopsis. J. Plant Physiol. 2013, 170:619-624.
5. Yonekura-Sakakibara K., et al. Comprehensive flavonol profiling and transcriptome coexpression analysis leading to decoding gene-metabolite correlation in Arabidopsis. Plant Cell 2008, 20:2160-2176.
6. Yoshida K., et al. Blue flower color development by anthocyanins: from chemical structure to cell physiology. Nat. Prod. Rep. 2009, 26:884-915.
7. Quilichini T.D., et al. New views on tapetum ultrastructure and pollen exine development in Arabidopsis. Ann. Bot. 2014, 114:1189-1201.
8. Hsieh K., Huang A.H.C. Tapetosomes in Brassica tapetum accumulate endoplasmic reticulum-derived flavonoids and alkanes for delivery to the pollen surface. Plant Physiol. 2007, 19:582-596.
9. Ariizumi T., Toriyama K. Genetic regulation of pollen sporopollenin biosynthesis and pollen exine development. Ann. Rev. Plant. Biol. 2011, 62:437-460.
10. Quilichini T.D., et al. The biosynthesis, composition and assembly of the outer pollen wall: a tough case to crack. Phytochemistry 2014, Published online June 3, 2014. http://dx.do.org/10.1016/j.phytochem.2014.05.002.
11. Wiermann R., Gubatz S. Pollen wall and sporopollenin. Int. Rev. Cytol. 1992, 140:35-72.
12. Dobritsa A.A., et al. LAP5 and LAP6 encode anther-specific proteins with similarity to chalcone synthase essential for pollen exine development in Arabidopsis. Plant Physiol. 2010, 153:937-955.
13. Kim S.S., et al. LAP6/polyketide synthase A and LAP5/Polyketide synthase B encode hydroxyalkyl α-pyrone synthases required for pollen development and sporopollenin biosynthesis in Arabidopsis thaliana. Plant Cell 2010, 22:4045-4066.
14. Grienenberger E., et al. Analysis of tetraketide α-pyrone reductase function in Arabidopsis thaliana reveals a previously unknown, but conserved, biochemical pathway in sporopollenin monomer biosynthesis. Plant Cell 2010, 22:4067-4083.
15. Edlund A.F., et al. Pollen and stigma structure and function: the role of diversity in pollination. Plant Cell 2004, 16:84-97.
16. Ishiguro S., et al. The Arabidopsis FLAKY POLLEN1 gene encodes a 3-hydroxy-3-methylglutaryl-coenzyme A synthase required for development of tapetum-specific organelles and fertility of pollen grains. Plant Cell Physiol. 2014, 51:896-911.
17. Meurer B., et al. Phenylpropanoid pattern in Fagales pollen and their phylogenetic relevance. Phytochemistry 1988, 27:823-828.
18. Pratviel-Sosa F., Percheron F. Les sophorosides des flavonols des quelques pollens. Phytochemistry 1972, 11:1809-1813.
19. Strack D., et al. Quercetin 3-glucosylgalactoside from pollen of Coryllus avellana. Phytochemistry 1984, 12:2970-2971.
20. Vogt T., Taylor L.P. Flavonol-3-O-glucosyltransferases associated with Petunia pollen produce gametophytic specific flavonoldiglycosides. Plant Physiol. 1995, 108:903-911.
21. Trapero A., et al. Characterization of a glucosyltransferase enzyme involved in the formation of kaempferol and quercetin sophorosides in Crocus sativus. Plant Physiol. 2012, 159:1335-1353.
22. Ferreres F., et al. 8-Methoxykaempferol 3-sophoroside a yellow pigment from almond pollen. Phytochemistry 1989, 28:1901-1903.
23. Mo Y., et al. Biochemical complementation of chalcone synthase mutants defines a role for flavonols in pollen. Proc. Natl. Acad. Sci. U.S.A. 1992, 89:7213-7217.
24. Ylstra B., et al. Flavonols stimulate germination, development, and tube growth of tobacco Pollen. Plant Physiol. 1992, 902-907.
25. Taylor L.P., Hepler P.K. Pollen germination and tube growth. Annu. Rev. Plant Physiol. Plant Mol. Biol. 1997, 48:461-491.
26. Forbes A.M., et al. Structure-activity relationship studies of flavonol analogues on pollen germination. J. Agric. Food Chem. 2014, 62:2175-2181.
27. Burbulis I.A., et al. A null mutation in the first enzyme of flavonoid biosynthesis does not affect male fertility in Arabidopsis. Plant Cell 1996, 8:1013-1025.
28. Stracke R., et al. Analysis of production of flavonol glycosides-dependent flavonol glycoside accumulation in Arabidopsis thaliana plants reveals MYB11- MYB12- and MYB111-independent flavonol glycoside accumulation. New Phytol. 2011, 188:985-1000.
29. Yonekura-Sakakibara K., et al. A flavonoid 3-O-glucoside:2"-O-glucosyltransferase responsible for terminal modification of pollen-specific flavonols in Arabidopsis thaliana. Plant J. 2014, 79:769-782.
30. Bassard J.E., et al. Phenolamides: bridging polyamines to the phenolic metabolism. Phytochemistry 2010, 71:1808-1824.
31. Negri G., et al. Hydroxycinnamic acid amide derivatives, phenolic compounds and antioxidant activities of extracts of pollen samples from southeast Brazil. J. Agric. Food Chem. 2011, 59:5516-5522.
32. Grienenberger E., et al. A BAHD acyltransferase is expressed in the tapetum of Arabidopsis anthers and is involved in the synthesis of hydroxycinnamoyl spermidines. Plant J. 2009, 58:246-259.
33. Matsuno M., et al. Evolution of a novel phenolic pathway for pollen development. Science 2009, 326:1688-1692.
34. Fellenberg C., et al. Tapetum-specific localization of a cation-dependent O-methyltransferase in Arabidopsis thaliana. Plant J. 2008, 56:132-145.
35. Handrick V., et al. Profiling of hydroxycinnamic amides in Arabidopsis thaliana pollen by tandem mass spectrometry. Anal. Bioanal. Chem. 2010, 398:2789-2801.
36. Luo J., et al. A novel polyamine acyltransferase responsible for the accumulation of spermidine conjugates in Arabidopsis seed. Plant Cell 2009, 21:318-333.
37. Onkokesung N., et al. MYB8 controls inducible phenolamide levels by activating three novel hydroxycinnamoyl-coenzyme A:polyamine transferases in Nicotiana attenuata. Plant Physiol. 2012, 158:389-407.
38. Agati G., et al. Functional roles of flavonoids in photoprotection: new evidence, lessons from the past. Plant Biochem. Physiol. 2013, 72:35-45.
39. Taylor L.P., Grotewold E. Flavonoids as developmental regulators. Curr. Opin. Plant Biol. 2005, 8:317-323.
40. Yue, et al. Transcriptional evidence for Inferred pattern of pollen tube-stigma metabolic coupling during pollination. PLoS ONE 2014, 9:e107046.
41. Quilichini T.D., et al. ABCG26-mediated polyketide trafficking and hydroxycinnamoyl spermidines contribute to pollen wall exine formation in Arabidopsis. Plant Cell 2014, 26:4483-4496.
42. Wollenweber E., Dietz H. Occurrence and distribution of free flavonoid aglycones in plants. Phytochemistry 1981, 20:869-932.
43. Martin-Tanguy J., et al. Hydroxycinnamic acids in fertile and cytoplasmatic male sterile lines of maize. Phytochemistry 1982, 8:1939-1945.
44. Fellenberg C., et al. Phenylpropanoid conjugate biosynthesis in flower buds of Arabidopsis thaliana. Phytochemistry 2009, 70:1392-1400.
45. Schweigert N., et al. Chemical properties of catechols and their molecular modes of toxic action in cells, from microorganisms to mammals. Environ. Microbiol. 2001, 3:81-91.
46. Gubatz S., et al. The location of hydroxycinnamic acid amides in the exine of Corylus pollen. Pollen Spores 1986, 28:347-354.
47. Kaur H., et al. R2R3-NaMYB8 regulates the accumulation of phenylpropanoid-polyamine conjugates, which are essential for local and systemic defense against insect herbivores in Nicotiana attenuata. Plant Physiol. 2010, 152:1731-1747.
48. Gaquerel E., et al. Revealing insect herbivory-induced phenolamide metabolism: from single genes to metabolic network plasticity analysis. Plant J. 2014, 79:679-692.
49. Daglia M. Polyphenols as antimicrobial agents. Curr. Opin. Biotechnol. 2012, 73:174-181.
50. Niphakis M.J., Cravatt B.F. Enzyme inhibitor discovery by affinity-based protein profiling. Ann. Rev. Biochem. 2014, 83:341-377.