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The identification of flavonoids and the expression of genes of anthocyanin biosynthesis in the chrysanthemum flowers

  • Published:
Biologia Plantarum

Abstract

In order to provide additional information on the coloration of chrysanthemum flowers, the flavonoid composition and the expression of six structural genes involved in anthocyanin pathway in the ray florets of a pink flowering (cv. H5) and two white flowering (cvs. Keikai and Jinba) Chrysanthemum grandiflorum cultivars were examined. HPLCDAD/ESI-MSn analysis showed that cyanidin 3-O-(6″-O-malonylglucoside) and cyanidin 3-O-(3″,6″-O-dimalonylglucoside) were the two major flavonoids presented in H5, while white flowering cultivars contained flavones instead of anthocyanins. Nine flavone derivatives were detected in the three cultivars, the amount of each flavone varied upon cultivars, and seven of these were identified as luteolin 7-O-arabinosylglucuronide, apigenin 7-O-glucoside, luteolin 7-O-malonylglucoside, apigenin 7-O-malonylglucoside, chrysoeriol 7-O-malonylglucoside, acacetin 7-O-rutinoside and acacetin 7-O-malonylglucoside. The two white flowering cultivars showed similar total flavonoid content, which was about two fold higher than that in H5. A high expression of the genes encoding dihydroflavonol 4-reductase and 3-O-glucosyltransferase was detected only in H5 but not in Keikai or Jinba. Chalcone synthase, chalcone isomerase, flavanone 3-hydroxylase, and flavonoid 3′-hydroxylase were expressed in all flowers, suggesting that the lack of anthocyanin in white flowering cultivars cannot be due to any blockage of their expression.

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Abbreviations

Ac-7-MalGlc:

acacetin 7-O-malonylglucoside

Ac-7-Rut:

acacetin 7-O-rutinoside

ANS:

anthocyanidin synthase

ANR:

anthocyanidin reductase

Ap-7-G:

apigenin 7-O-glucoside

Ap-7-MalGlc:

apigenin 7-O-malonylglucoside

Ch-7-MalGlc:

chrysoeriol 7-O-malonylglucoside

CHI:

chalcone isomerase

CHS:

chalcone synthase

Cy-3-MalGlc:

cyanidin 3-O-(6″-Omalonylglucoside)

Cy-3-MalMalGlc:

cyanidin 3-O-(3″, 6″-O-dimalonylglucoside)

DFR :

dihydroflavonol 4-reductase

F3H:

flavanone 3-hydroxylase

F3′H:

flavonoid 3′-hydroxylase

FNS:

flavone synthase

3GT :

3-O-glucosyltransferase

Lu-7-AraGluc:

luteolin 7-O-arabinosylglucuronide

Lu-7-MalGlc:

luteolin 7-O-malonylglucoside

OMT:

O-methyltransferase

References

  • Ahmed, N., Maekawa, M., Noda, K.: Anthocyanin accumulation and expression pattern of anthocyanin biosynthesis genes in developing wheat coleoptiles. — Biol. Plant. 53: 223–228, 2009.

    Article  CAS  Google Scholar 

  • Castañeda-Ovando, A., Pacheco-Hernández, M.L., Páez-Hernández, M.A., Rodríguez J.A., Galán-Vidal, CA.: Chemical studies of anthocyanins: a review. — Food Chem. 113: 859–871, 2009.

    Article  Google Scholar 

  • Feyissa, D.N., Løvdal, T., Olsen, K.M., Slimestad, R., Lillo, C.: The endogenous GL3, but not EGL3, gene is necessary for anthocyanin accumulation as induced by nitrogen depletion in Arabidopsis rosette stage leaves. — Planta 230: 747–754, 2009.

    Article  PubMed  CAS  Google Scholar 

  • Forkmann, G., Stefan, M.: Metabolic engineering and applications of flavonoids. — Curr. Opin. Biotechnol. 12: 155–160, 2001.

    Article  PubMed  CAS  Google Scholar 

  • Fossen, T., Andersen, ø.M.: Cyanidin 3-O-(6″-succinyl-β- glucopyranoside) and other anthocyanins from Phragmites australis. — Phytochemistry 49: 1065–1068, 1998.

    Article  CAS  Google Scholar 

  • Honda, C., Nobuhiro, K., Masato, W., Satoru, K., Shozo, K., Junichi, S., Zhang, Z.L., Tomomi, T., Takaya, M.: Anthocyanin biosynthetic genes are coordinately expressed during red coloration in apple skin. — Plant Physiol. Biochem. 40: 955–962, 2002.

    Article  CAS  Google Scholar 

  • Ismail, G.S.M., Mohamed, H.E.: Alteration in growth and thylakoid membrane lipid composition of Azolla caroliniana under phosphate deficiency. — Biol. Plant. 54: 671–676, 2010.

    Article  CAS  Google Scholar 

  • Kereamy, A.E., Chervin, C., Souquet, J.M., Moutounet, M., Monje, M.C., Nepveu, F., Mondies, H., Ford, C.M., Van Heeswijk, R., Roustan, J.P.: Ethanol triggers grape gene expression leading to anthocyanin accumulation during berry ripening. — Plant Sci. 163: 449–454, 2002.

    Article  Google Scholar 

  • Lai, J.P., Lim, Y.H., Su, J., Shen, H.M., Ong, C.N.: Identification and characterization of major flavonoids and caffeoylquinic acids in three Compositae plants by LC/DAD-APCI/MS. — J. Chromatogr. 848: 215–225, 2007.

    Article  CAS  Google Scholar 

  • Lee, G.J., Chung, S.J., Park, I.J., Lee, J.S., Kim, J.B., Kim, D.S., Kang, S.Y.: Variation in the phenotypic features and transcripts of color mutants of chrysanthemum (Dendranthema grandiflorum) derived from gamma ray mutagenesis. — J. Plant Biol. 51: 418–423, 2008.

    Article  CAS  Google Scholar 

  • Li, C.H., Du, H., Wang, L.S., Shu, Q.Y., Zheng, Y.R., Xu, Y.J., Zhang, J.J., Zhang, J., Yang, R.Z., Ge, Y.X.: Flavonoid composition and antioxidant activity of tree peony (Paeonia, section Moutan) yellow flowers. — J. Agr. Food Chem. 57: 8496–8503, 2009.

    Article  CAS  Google Scholar 

  • Lin, L.Z., Harnly, J.M.: A screening method for the identification of glycosylated flavonoids and other phenolic compounds using a standard analytical approach for all plant materials. — J. Agr. Food Chem. 55: 1084–1096, 2007.

    Article  CAS  Google Scholar 

  • Lu, X., Zhou, W., Gao F.: Chromosomal location of 45S rDNA and dfr gene in Citrus sinensis. — Biol. Plant. 54: 798–800, 2010.

    Article  CAS  Google Scholar 

  • Mato, M., Onozaki, T., Ozeki, Y., Higeta, D., Itoh, Y., Yoshimoto, Y., Ikeda, H., Yoshida, H., Shibata, M.: Flavonoid biosynthesis in white-flowering Sim carnations (Dianthus caryophyllus). — Sci. Hort. 84: 333–347, 2000.

    Article  CAS  Google Scholar 

  • Nakatsuka, A., Mizuta, D., Kii, Y., Miyajima, I., Kobayashi, N.: Isolation and expression analysis of flavonoid biosynthesis genes in evergreen azalea. — Sci Hort. 118: 314–20, 2008.

    Article  CAS  Google Scholar 

  • Nakayama, M., Koshioka, M., Shibata, M., Hiradate, S., Sugie, H., Yamaguchi, M.: Identification of cyanidin 3-O-(3″,6″- O-dimalonyl-beta-glucopyranoside) as a flower pigment of chrysanthemum (Dendranthema grandiflora). — Biosci. Biotechnol. Biochem. 6: 1607–1608, 1997.

    Article  Google Scholar 

  • Nesi, N., Jond, C., Debeaujo, I., Caboche, M., Lepineic, L.: The Arabidopsis TT2 gene encodes an R2R3 MYB domain protein that acts as a key determinant for proanthocyanidin accumulation in developing seed. — Plant Cell 13: 2099–2114, 2001.

    Article  PubMed  CAS  Google Scholar 

  • Prasain, J.K., Wang, C.C., Barnes, S.: Mass spectrometric methods for the determination of flavonoids in biological samples. — Free Radical Biol. Med. 37: 1324–1350, 2004.

    Article  CAS  Google Scholar 

  • Rusak, G., Cerni, S., Stupin Polancec, D., Ludwig-Müller J.: The responsiveness of the IAA2 promoter to IAA and IBA is differentially affected in Arabidopsis roots and shoots by flavonoids. — Biol. Plant. 54: 403–414, 2010.

    Article  CAS  Google Scholar 

  • Saito, N., Toki, K., Honda, T., Kawase, K.: Cyanidin 3- malonylglucuronylglucoside in Bellis and cyanidin 3- malonylglucoside in Dendranthema. — Phytochemistry 27: 2963–2966, 1988.

    Article  CAS  Google Scholar 

  • Schwinn, K.E., Davies, K.M.: Flavonoids. -In: Davies, K.M. (ed.): Plant Pigments and their Manipulation. Pp. 92–149. Blackwell Press, Oxford 2004.

    Google Scholar 

  • Schwinn, K.E., Kenneth, R.M., Nigel, K.G.: Floral flavonoids and the potential for pelargonidin biosynthesis in commercial chrysanthemum cultivars. — Phytochemistry 35: 145–150, 1993.

    Article  Google Scholar 

  • Stich, K., Eidenberger, T., Wurst, F., Forkmann, G.: Enzymatic conversion of dihydrofavonols to flavan-3,4-diols using flower extracts of Dianthus caryophyllus L. (carnation). — Planta 187: 103–108, 1992.

    Article  CAS  Google Scholar 

  • Yang, D.H., Yun, P.Y., Park, S.Y., Plaha, P., Lee, D.S., Hwang, Y.S., Kim, Y.A., Lee, J.S., Han, B.H., Lee, S.Y., Suh, E.J., Lim, Y.P.: Cloning, characterization and expression of a lateral suppressor-like gene from chrysanthemum (Dendranthema grandiflorum Kitamura). — Plant Physiol. Biochem. 43: 1044–1052, 2005.

    Article  PubMed  CAS  Google Scholar 

  • Yang, R.Z., Wei, X.L., Gao, F.F., Wang, L.S., Zhang, H.J., Xu, Y.J., Li, C.H., Ge, Y.X., Zhang, J.J., Zhang, J.: Simultaneous analysis of anthocyanins and flavonols in petals of Lotus nelumbo cultivars by high-performance liquid chromatography-photodiode array detection/electrospray ionization mass spectrometry. — J. Chromatogr. 1216: 106–112, 2009.

    Article  CAS  Google Scholar 

  • Zhang, J.J., Wang, L.S., Shu, Z., Li, C., Zhang, J., Wei, X.L., Tian, D.K.: Comparison of anthocyanins in non-blotches and blotches of the petals of Xibei tree peony. — Sci. Hort. 114: 104–111, 2007.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. College of Horticulture, Nanjing Agricultural University, Nanjing, 210095, China

    S. -M. Chen, X. -R. Zhu, Y. -M. Deng, F. -D. Chen & Z. Zhang

  2. Beijing Botanical Garden, Institute of Botany, the Chinese Academy of Sciences, Beijing, 100093, China

    C. -H. Li & L. -S. Wang

  3. Graduate University of Chinese Academy of Sciences, Beijing, 100049, China

    C. -H. Li

  4. College of Landscape Architecture, Beijing Forestry University, Beijing, 100083, China

    W. Sun

  5. Urumqi Botanical Garden, Urumqi, 830011, China

    W. Sun

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  1. S. -M. Chen
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  2. C. -H. Li
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  4. Y. -M. Deng
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  7. F. -D. Chen
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Correspondence to F. -D. Chen.

Additional information

Acknowledgments: This work was supported by the National Natural Science Foundation of China (Grant No. 30872064, 31071820, 31071825), Non-profit Industry Financial Program of the Ministry of Science and Technology of the P.R. China (200903020), 863 project of MST of China (2011AA10020801), China Postdoctoral Science Foundation Funded Project (Grant No. 20070411058), Project-sponsored by SRF for ROCS, SEM (Grant No. [2008]890), Science and Technology Innovation Fund for the Youth of Nanjing Agricultural University (Grant No. KJ07009), and Project-sponsored by Qing Lan Project of Jiangsu Province (Grant No. 2008[30]).

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Chen, S.M., Li, C.H., Zhu, X.R. et al. The identification of flavonoids and the expression of genes of anthocyanin biosynthesis in the chrysanthemum flowers. Biol Plant 56, 458–464 (2012). https://doi.org/10.1007/s10535-012-0069-3

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  • DOI: https://doi.org/10.1007/s10535-012-0069-3

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