The D iversity of Flower Color of the O rnam en ta l Sunflower and the Rela tion to An thocyan in s

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2008, 35 (6) : 863-868 Acta Horticulturae Sinica 1, 2, 1, 1, 1, 1, 1, 13, 13 ( 1, 100093; 2, 100049) : (RHSCC) 36, ; (HPLC), 9, 9,, / ;, : ; ; ; ; ; : S 68 : A : 05132353X (2008) 0620863206 The D iversity of Flower Color of the O rnam en ta l Sunflower and the Rela tion to An thocyan in s ZHANG Yuan2yuan 1, 2, Q IDong2mei 1, L IU Hui 1, ZHANG J i2chong 1, L I Chong2hui 1, ZHANG jie 1, WANG L iang2sheng 13, and L IU Gong2she 13 ( 1 Institute of B otany, the Chinese A cadem y of Sciences, B eijing 100093, China; 2 Graduate U niversity, the Chinese A cadem y of Sciences, B eijing 100049, China) Abstract: Flower color is one of the most important ornam ental characters. on the polymorphism of flower color of the ornam ental sunflower. This study is the first report The floral color was m easured according to the Royal Horticultural Society Colour Chart ( RHSCC) and by a NF333 spectrophotometer. And UV 2V isible spectra of flower p igm ents were performed. The results indicated that the floral color of the ornamental sunflow2 er includes the red group and the yellow group. The results also showed that there are 9 anthocyanins of all 36 ornam ental sunflower genotypes. Only one anthocyanin was detected in all 36 experim ental materials. The re2 sults of the m ultilevel mass spectrum showed that the anthocyandin of the sunflower was cyanidin. The cyani2 din was combined to glucose, rhamnose and /or arabinose to form glucosides. B ut we did not detect the cyanin in the pure yellow sunflower. sunflower. Key words: This supposes that the cyanin was the m atter of the red group of the ornamental sunflower; ornam ental sunflower; ray flower; flower color; polymorphism; anthocyanin (ornamental sunflower) ( colorful sunflower), ( Heli2 anthus) (H. annuus L. ) 50 ( Seiler, 2002), 1976 (USDA2ARS), : 2008-03 - 03; : 2008-05 - 15 : (30571305) 3 Author for correspondence ( E2mail: wanglsh@ ibcas1ac1cn; liugs@ ibcas1ac1cn) :

864 35 2 163 (Dec. 29, 2004, ARS: the U. S. Department of Agricultureπs Chief Scientific Re2 search Agency) 1 264 ( http: / / seed. agron. ntu. edu. tw /germp lasm /chinagerm. htm l. ), (, 1994),, ( Schneiter, 1997),, (, 2006;, 2006),, (Charles & Sando, 1925),,, 1 111, 2006 6 7,, OLYMPUS C730UZ,,,, 172, - 40 112 (Royal Horticultural Society Colour Chart, RHSCC) RHSCC (1 2 80 81 82), 4 (A B C D ), RHSCC, RHSCC (Voss, 1992; W ang et al., 2004) ( Spectrophotometer, NF333,, C /2 ) ( International Comm ission on Illum ination, C IE) C IE L 3 a 3 b 3 L 3 a 3 b 3, L 3 a 3 b 3 L 3 0 100, ; a 3, ; b 3, C 3 h : C 3 = ( a 3 2 + b 3 2 ) 1 /2, h = arctan ( b 3 /a 3 ) C 3 L 3,, (Voss, 1992; W ang et al., 2004), L 3 a 3 b 3 5, (, 2006) ( high performance liquid chromatography, HPLC) ( Tian et al., 2005) D IONEX P680, D IONEX PDA2100; D IONEX TCC2100; TOSOH TSK2GEL ODS280TS ( < 416 mm 150 mm ) : 012 014 g, ( = 1 70 2 27) 24 h, 0145 m, - 20 A 115% ; B = 25 20 115 5315 0145 m 10 L, 40, 018 ml m in - 1 : 0 m in, 40% B; 40 m in, 85% B; 50 m in, 40% B, 530

6 : 865 nm, (, 2006) (HPLC - ESI - MS/MS n ), Agilent 1100 LC /MSD Trap VL : ; 35, 018 ml m in - 1, 10 L A : 011% ; B : : 0 m in, 40% B; 40 m in, 85% B; 50 m in, 40% B, 520 nm ( ESI),,,, (m /z) : 100 1 000; ( SIM ) MS n 3 500 V, 214 10 5 Pa, 12014 V, 350, (N 2 ) 810 L m in - 1, C ID 30% LC /MSD Trap 512 ( Cuyckens & Claeys, 2004; Eichhorn & W interhalter, 2005; Tian et al., 2005; Montoro et al., 2006) M icrosoft Office Excel 2003, SPSS 1115 2 211 21111,,,, ( 1, a b) ( 1, c d) ( 1, l) ( 1, k), ( 1, e f g) ( 1, h) ; ( 1, b) ( 1, a c d e f g h i j k l) F ig. 1 1 The ornam en ta l sunflowers of d ifferen t flora l colors

866 35 21112 RHSCC,, RHSCC 3B 15A,, (Lemon) (O range) ; RHSCC 46A 59A, (Red) (NF333), C IE L 3 a 3 b 3 : a 3-15198 28133, RH2 SCC ; b 3 4143 101185, RHSCC ; L 3 11105 76188, RHSCC ;,, ( 1) 1 Table 1 The sam ple of the sunflowers and the C IE L 3 a 3 b 3 coord ina te Samp le classes RHSCC L 3 a 3 b 3 C h / The group of red 46A 59A 24122 9147 21163 3168 19136 10156 30106 8115 39116 14128 The group of orange 7A 15A 68193 6195-1150 6141 91183 8191 92107 8179 90166 3198 The group of lemon 3B 9B 67100 6131-6138 5142 47163 12174 48122 13125 96192 5103 :, n = 5 Note: Data showed mean standard deviation, n = 5. (NF333) a 3, b 3, 172 a 3 b 3, 172 36 ( 2), 22 ( 2, 2a), 14, 6 ( 2, 2b21) 8 ( 2, 2b22), 2, ( 2, 2a), a 3, 10 30, ( 2, 2b), b 3 30 110, 1 a ( 2, 2b21) 1 c ( 2, 2b22) 212 F ig. 2 C IE L 3 a 3 b 3 2 The C IE L 3 a 3 b 3 d istr ibuting of the d ifferen t colors of the sunflower 21211 HPLC HPLC 36 9 (A B C D E F G H I), 2,,, G 100%, ; G ( 97% ) C (3% ) ;,, G ( 75% ), C (17% ), (H 3%, E 2%, D F I 1% ), 2 Table 2 The rela tive con ten t of an thocyan in s in The kinds of flower color d ifferen t flora l color groups /% A B C D E F G H I O range 0 0 0 0 0 0 100 0 0 Lemon 0 0 3 0 0 0 97 0 0 Red 0 0 17 1 2 1 75 3 1

6 : 867 3 35, G, G, 65%, A 1% 21212 LC /MS,, ( 3) HPLC 287, ( 3, A ) ( 3, F) ( 3, C) 3 F ig. 3 HPLC chroma togram s of an thocyan in s in sunflowers 3 Table 3 HPLC - ES I - M S /M S n ana lysis and ten ta tive iden tif ica tion of flower p igm en ts in sunflower Anthocya2 Peak Molecular mass Tentative identification nins No. No. A 1 28617 (Cy), 44818 [M + H ] +, 47018 [M +Na ] + - Cyandin2glucoside B 2 28618 (Cy), 53418 [M + H ] +, 55618 [M +Na ] + - - Cyandin2malonyl2glucoside C 3 28618 (Cy), 41818 [M + H ] +, 44018 [M +Na ] + - Cyandin2arabinoside D 4 28617 (Cy), 54818 [M + H ] +, 57018 [M +Na ] + - Cyandin2malonyl2glucuronic2acid E 5 28617 (Cy), 46218 [M + H ] + - Cyandin2glucuronic acid F 6 28616 (Cy), 51818 [M + H ] +, 54018 [M +Na ] +, G Maybe the isomeric compound of G 45419 [ Cy2Rham2Na ] + G 7 28616 (Cy), 51818 [M + H ] +, 54018 [M +Na ] + - - Cyandin2malonyl2rhamnoside H 8 Not available I 9 Not available 3,,,, (Hashimoto et al., 2000),, RHSCC,,, Charles Sando (1925) Schneiter (1997) LC /MS,, ( 3), (L 3 ) ( 1),,

868 35 ( 2), G, G, C,,,, (B rouillard & Dangles, 1994; Grotewold, 2006) A l Fe Mg Cd Zn Co N i ph (Marrs et al., 1995; Mol et al., 1998),, References Bai Xin2xiang, Hu Ke, Dai Si2lan, W ang L iang2sheng. 2006. Components of flower p igments in the petals of different color Chrysanthem um m orifolium Ramat. cultivars. Journal of Beijing Forestry University, 28 (5) : 84-89. ( in Chinese),,,. 2006.., 28 (5) : 84-89. B rouillard R, Dangles O. 1993. Flavonoids and flower colour/ /Harborne J B. The flavonoids: Advances in research since 1986. London: Chap2 man & Hall: 565-588. Charles E, Sando. 1925. Anthocyanin formation in Helianthus annuus from the office of p lant physiological investigations, bureau of p lant indus2 try, united states department of agriculture, W ashington. Cuyckens F, ClaeysM. 2004. Mass spectrometry in the structural analysis of flavonoids. J Mass Spectrom, 39: 1-15. Eichhorn S, W interhalter P. 2005. Anthocyanins from p igmented potato ( Solanum tuberosum L. ) varieties. Food Research International, 38: 943-948. Grotewold E. 2006. The genetics and biochem istry of floral p igments. Annu Rev Plant B iol, 57: 761-780. Hashimoto F, Tanaka M, Maeda H, Shim izu K, Sakata Y. 2000. Characterization of cyanic flower colour of delphinium cultivars. Jpn Soc Hortic Sci, 69 (4) : 428-434. L iu Gong2she, A lain Bonjean, Peng Ke2jing. 1994. The research and exp loitation of sunflower. Beijing: China Science and Technology Publishing House. ( in Chinese),,. 1994.. :. L iu Gong2she, Xu Su2xia, L iu Xiao2li. 2006. Characteristics of NEW FREE CMS line and utilization in ornamental sunflower. Acta Agronom ica Sinica, 32 (11) : 1752-1755. ( in Chinese),,. 2006. NEW FREE., 32 (11) : 1752-1755. Marrs K A, A lfenlto M R, L loyd A M, Rhodes C A. 1995. A glutathione2transferase involved in vacuolar transfer encoded b the maize gene B ronze22. Nature, 375: 397-400. Mol J, Grotewold E, Koes R. 1998. How genes paint flowers and seeds. Trends in Plant Science, 3: 212-217. Montoro P, Carlo I G Tuberoso, Perrone A, Piacente S, Cabras P, Pizza C. 2006. Characterisation by liquid chromatography2electrosp ray tandem mass spectrometry of anthocyanins in extracts ofm yrtus comm unis L. berries used for the p reparation of myrtle liqueur. Journal of Chromatogra2 phy A, 1112: 232-240. Schneiter A A. 1997. Sunflower technology and p roduction. Agronomy Vol. 35. Madison, W isconsin. USA. Seiler G J. 2002. W ild sunflower germplasm: A perspective on characteristics of use to sunflower breeders in develop ing countries. International Symposium on Sunflower in Developing Countries. Tian Q ing2guo, Monica Giustia M, Gary D Stoner, Steven J Schwartz. 2005. Screening for anthocyanins using high2performance liquid chromatog2 raphy coup led to electrospray ionization tandem mass spectrometry with p recursor2ion analysis, product2ion analysis, common2neutral2loss anal2 ysis, and selected reaction monitoring. Journal of Chromatography A, 1091: 72-82. Voss D H. 1992. Relating colourimeter nleasurement of p lant colour to the Royal Horticultural Society Colour Chart. HortScience, 27 ( 12) : 1256-1260. W ang L S, Hashimoto F, ShiraishiA, AokiN, L i J J, Sakata Y. 2004. Chem ical taxonomy of the Xibei tree peony from China by floral p igmenta2 tion. Journal of Plant Research, 117 (1) : 47-55. Xu Su2xia, L iu Gong2she. 2006. Mechanism and application of cytoplasm ic male2sterility in sunflower (Helianthus annuus L. ). Acta Agronom ica Sinica, 32 (10) : 1574-1578. ( in Chinese),. 2006.., 32 (10) : 1574-1578.