CDNA cloning and characterization of chalcone isomerase-fold proteins from snapdragon (Antirrhinum majus L.) flowers

Plant Biotechnology

Volumn 31, Issue 2, 2014, Pages 105-114

  Fujino, Naoto ^a   Yamazaki, Tatsuya ^a   Li, Yanbing ^a   Kera, Kota ^a   Furuhashi, Erika ^a   Yamashita, Satoshi ^a   Morita, Yasumasa ^b,c   Nakayama, Masayoshi ^b   Takahashi, Seiji ^a   Nakayama, Toru ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b NATIONAL INSTITUTE OF VEGETABLE AND TEA SCIENCE   (Japan)

^c KAGAWA UNIVERSITY   (Japan)

Author keywords

Antirrhinum majus L.; Aurone; Chalcone isomerase; Enhancer of flavonoid production; Snapdragon

Indexed keywords

EID: 84903531842     PISSN: 13424580     EISSN: 13476114     Source Type: Journal    
DOI: 10.5511/plantbiotechnology.14.0109c     Document Type: Article

References (32)

1. Akashi T, Fukuchi-Mizutani M, Aoki T, Ueyama Y, Yonekura-Sakakibara K, Tanaka Y, Kusumi T, Ayabe S (1999) Molecular cloning and biochemical characterization of a novel cytochrome P450, flavone synthase II, that catalyzes direct conversion of flavanones to flavones. Plant Cell Physiol 40: 1182-1186.
2. Asen S, Norris KH, Stewart RN (1972) Copigmentation of aurone and flavone from petals of Antirrhinum majus. Phytochemistry 11: 2739-2741.
3. Farag MA, Deavours BE, de Fatima A, Naoumkina M, Dixon RA, Sumner LW (2009) Integrated metabolite and transcript profiling identify a biosynthetic mechanism for hispidol in Medicago truncatula cell cultures. Plant Physiol 151: 1096-1113.
4. Forkmann G, Stotz G (1981) Genetic control of flavanone 3-hydroxylase activity and flavonoid 3′-hydroxylase activity in Antirrhinum majus (Snapdragon). Z Naturforsch 36C: 411-416.
5. Gilbert RI (1973) Chalcone glycosides of Antirrhinum majus. Phytochemistry 12: 809-810.
6. Harborne JB (1963) Plant Polyphenols. X. Flavone and aurone glycosides of Antirrhinum. Phytochemistry 2: 327-334.
7. Hatayama M, Ono E, Yonekura-Sakakibara K, Tanaka Y, Nishino T, Nakayama T (2006) Biochemical characterization and mutational studies of a chalcone synthase from yellow snapdragon (Antirrhinum majus) flowers. Plant Biotechnol 23: 373-378.
8. Hur S, Bruice TC (2003) Enzymes do what is expected (chalcone isomerase versus chorismate mutase). J Am Chem Soc 125: 1472-1473.
9. Hur S, Newby ZE, Bruice TC (2004) Transition state stabilization by general acid catalysis, water expulsion, and enzyme reorganization in Medicago savita chalcone isomerase. Proc Natl Acad Sci USA 101: 2730-2735.
10. Iida S, Morita Y, Choi JD, Park KI, Hoshino A (2004) Genetics and epigenetics in flower pigmentation associated with transposable elements in morning glories. Adv Biophys 38: 141-159.
11. Jez JM, Bowman ME, Dixon RA, Noel JP (2000) Structure and mechanism of the evolutionarily unique plant enzyme chalcone isomerase. Nat Struct Biol 7: 786-791.
12. Jez JM, Bowman ME, Noel JP (2002) Role of hydrogen bonds in the reaction mechanism of chalcone isomerase. Biochemistry 41: 5168-5176.
13. Jez JM, Noel JP (2002) Reaction mechanism of chalcone isomerase: pH dependence, diffusion control, and product binding differences. J Biol Chem 277: 1361-1369.
14. Laemmli UK (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227: 680-685.
15. Martin C, Prescott A, Mackay S, Bartlett J, Vrijlandt E (1991) Control of anthocyanin biosynthesis in flowers of Antirrhinum majus. Plant J 1: 37-49.
16. Mol JNM, Robbinst MP, Dixon RA, Veltkamp E (1985) Spontaneous and enzymic rearrangement of naringenin chalcone to flavanone. Phytochemistry 24: 2267-2269.
17. Morita Y, Takagi K, Fukuchi-Mizutani M, Ishiguro K, Tanaka Y, Nitasaka E, Nakayama M, Saito N, Kagami T, Hoshino A, et al. (2014) A chalcone isomerase-like protein enhances flavonoid production and flower pigmentation. Plant J, DOI 10. 1111/tpj. 12469.
18. Moustafa E, Wong E (1967) Purification and properties of chalcone-flavanone isomerase from soya bean seed. Phytochemistry 6: 625-632.
19. Nakayama T, Sato T, Fukui Y, Yonekura-Sakakibara K, Hayashi H, Tanaka Y, Kusumi T, Nishino T (2001) Specificity analysis and mechanism of aurone synthesis catalyzed by aureusidin synthase, a polyphenol oxidase homolog responsible for flower coloration. FEBS Lett 499: 107-111.
20. Nakayama T, Yonekura-Sakakibara K, Sato T, Kikuchi S, Fukui Y, Fukuchi-Mizutani M, Ueda T, Nakao M, Tanaka Y, Kusumi T, et al. (2000) Aureusidin synthase: A polyphenol oxidase homolog responsible for flower coloration. Science 290: 1163-1166.
21. Ngaki MN, Louie GV, Philippe RN, Manning G, Pojer F, Bowman ME, Li L, Larsen E, Wurtele ES, Noel JP (2012) Evolution of the chalcone-isomerase fold from fatty-acid binding to stereospecific catalysis. Nature 485: 530-533.
22. Ono E, Fukuchi-Mizutani M, Nakamura N, Fukui Y, Yonekura-Sakakibara K, Yamaguchi M, Nakayama T, Tanaka T, Kusumi T, Tanaka Y (2006a) Yellow flowers generated by expression of the aurone biosynthetic pathway. Proc Natl Acad Sci USA 103: 11075-11080.
23. Ono E, Hatayama M, Isono Y, Sato T, Watanabe R, Yonekura-Sakakibara K, Fukuchi-Mizutani M, Tanaka Y, Kusumi T, Nishino T, et al. (2006b) Localization of a flavonoid biosynthetic polyphenol oxidase in vacuoles. Plant J 45: 133-143.
24. Ralston L, Subramanian S, Matsuno M, Yu O (2005) Partial reconstruction of flavonoid and isoflavonoid biosynthesis in yeast using soybean type I and type II chalcone isomerases. Plant Physiol 137: 1375-1388.
25. Rozen S, Skaletsky H (2000) Primer3 on the WWW for general users and for biologist programmers. Methods Mol Biol 132: 365-386.
26. Ruiz-Pernia JJ, Tunon I, Moliner V, Hynes JT, Roca M (2008) Dynamic effects on reaction rates in a Michael addition catalyzed by chalcone isomerase: Beyond the frozen environment approach. J Am Chem Soc 130: 7477-7488.
27. Saslowsky D, Winkel-Shirley B (2001) Localization of flavonoid enzymes in Arabidopsis roots. Plant J 27: 37-48.
28. Saslowsky DE, Warek U, Winkel BSJ (2005) Nuclear localization of flavonoid enzymes in Arabidopsis. J Biol Chem 280: 23735-23740.
29. Sato T, Nakayama T, Kikuchi S, Fukui Y, Yonekura-Sakakibara K, Ueda T, Nishino T, Tanaka Y, Kusumi T (2001) Enzymatic formation of aurones in the extracts of yellow snapdragon flowers. Plant Sci 160: 229-236.
30. Schwarz-Sommer Z, Davies B, Hudson A (2003) An everlasting pioneer: The story of Antirrhinum research. Nat Rev Genet 4: 657-666.
31. Shimada N, Aoki T, Sato S, Nakamura Y, Tabata S, Ayabe S (2003) A cluster of genes encodes the two types of chalcone isomerase involved in the biosynthesis of general flavonoids and legumespecific 5-deoxy(iso)flavonoids in Lotus japonicus. Plant Physiol 131: 941-951.
32. Shirzadegan M, Christie P, Seemann JR (1991) An efficient method for isolation of RNA from tissue cultured plant cells. Nucleic Acids Res 19: 6055.