Skip to main content

Coloring Soybeans with Anthocyanins?

  • Chapter
  • First Online:
Book cover The Biological Activity of Phytochemicals

Part of the book series: Recent Advances in Phytochemistry ((RAPT,volume 41))

Abstract

The seed coats of black soybean (Glycine max (L.) Merr.) accumulate all anthocyanins required for the red (cyanidin-), blue (delphinidin-), purple (petunidin-), and orange (pelargonidin-3-O-glucoside) coloration of plant tissues. Metabolic engineering of anthocyanin biosynthesis in black soybean may potentially be used to generate distinct colors for the visible identification of transgenic seeds. Presently the causal agents of black coloration in soybean seed coats are speculative, and factors such as anthocyanic vacuolar inclusions (AVIs), co-pigmentation, and oxidation are likely involved in generating the black phenotype. This chapter is a perspective on anthocyanin biosynthesis in black soybean, the present understanding of black coloration in plant tissues, and potential strategies for engineering seed colors in light of substantial equivalence.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 89.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 119.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Lemaux PG (2008) Genetically engineered plants and foods: a scientist’s analysis of the issues (Part I). Annu Rev Plant Biol 59:771–812

    Article  CAS  PubMed  Google Scholar 

  2. Doyle A (2008) EMBARGOED – World fails to monitor biotech trade – UN study. Williams R (ed). Thomson Reuters

    Google Scholar 

  3. Meyer P, Heidmann I, Forkmann G et al (1987) A new petunia flower colour generated by transformation of a mutant with a maize gene. Nature 330:677–678

    Article  CAS  PubMed  Google Scholar 

  4. Tanaka Y, Katsumoto Y, Brugliera F et al (2005) Genetic engineering in floriculture. Plant Cell, Tiss and Org Cult 80:1–24

    Article  CAS  Google Scholar 

  5. Katsumoto Y, Fukuchi-Mizutani M, Fukui Y et al (2007) Engineering of the rose flavonoid biosynthetic pathway successfully generated blue-hued flowers accumulating delphinidin. Plant Cell Physiol 48:1589–1600

    Article  CAS  PubMed  Google Scholar 

  6. Holton T, Tanaka Y (1994) Blue roses-a pigment of our imagination? Trends Biotechnol 12:40–42

    Article  Google Scholar 

  7. Choung M, Baek I-Y, Kang S-T et al (2001) Isolation and determination of anthocyanins in seed coats of black soybean (Glycine max (L.) Merr.). J Agric Food Chem 49:5848–5851

    Article  CAS  PubMed  Google Scholar 

  8. Lee JH, Kang NS, Shin S-O et al (2009) Characterization of anthocyanins in the black soybean (Glycine max L.) by HPLC-DAD-ESI/MS analysis. Food Chem 112:226–231

    Article  CAS  Google Scholar 

  9. Springob K, Nakajima J, Yamazaki M et al (2003) Recent advances in the biosynthesis and accumulation of anthocyanins. Nat Prod Rep 20:288–303

    Article  CAS  PubMed  Google Scholar 

  10. Bernard RL, Weiss MG (1973) Qualitative genetics. In: Caldwell BE (ed) Soybeans: improvement, production, and uses, 1st edn. Am Soc Agron, Wisconsin

    Google Scholar 

  11. Palmer RG, Kilen TC (1987) Qualitative genetics and cytogenetics. In: Wilcox JR (ed) Soybeans: improvement, production and uses, 1st edn. Am Soc Agron, Wisconsin

    Google Scholar 

  12. Tuteja JH, Vodkin LO (2008) Structural features of the endogenous CHS silencing and target loci in the soybean genome. Crop Sci 48:S49–S68

    Article  CAS  Google Scholar 

  13. Senda M, Masuta C, Ohnishi S et al (2004) Patterning of virus-infected Glycine max seed coat is associated with suppression of endogenous silencing of chalcone synthase genes. Plant Cell 16:807–818

    Article  CAS  PubMed  Google Scholar 

  14. Tuteja JH, Clough SJ, Chan WC et al (2004) Tissue-specific gene silencing mediated by a naturally occurring chalcone synthase gene cluster in Glycine max. Plant Cell 16:819–835

    Article  CAS  PubMed  Google Scholar 

  15. Kasai A, Ohnishi S, Yamazaki H et al (2009) Molecular mechanism of seed coat discoloration induced by low temperature in yellow soybean. Plant Cell Physiol 50:1090–1098

    Article  CAS  PubMed  Google Scholar 

  16. Toda K, Yang D, Yamanaka N et al (2002) A single-base deletion in soybean flavonoid 3ʹ-hydroxylase gene is associated with gray pubescence color. Plant Mol Biol 50:187–196

    Article  CAS  PubMed  Google Scholar 

  17. Zabala G, Vodkin L (2003) Cloning of the pleiotropic T locus in soybean and two recessive alleles that differentially affect structure and expression of the encoded flavonoid 3ʹ hydroxylase. Genetics 163:295–309

    CAS  PubMed  Google Scholar 

  18. Buzzell R, Buttery B, MacTavish D (1987) Biochemical genetics of black pigmentation of soybean seed. The J Hered 78:53–54

    Google Scholar 

  19. Saslowsky D, Winkel-Shirley B (2001) Localization of flavonoid enzymes in Arabidopsis roots. Plant J 27:37–48

    Article  CAS  PubMed  Google Scholar 

  20. Winkel BSJ (2009) Metabolite channeling and multi-enzyme complexes. In: Osbourn AE, Lanzotti V (eds) Plant-derived natural products: synthesis, function, and application. Springer, New York

    Google Scholar 

  21. Zabala G, Vodkin LO (2007) A rearrangement resulting in small tandem repeats in the F35H gene of white flower genotypes is associated with the soybean W1 locus. Plant Genome 47:S113–S124

    Google Scholar 

  22. Iwashina T, Githiri SM, Benitez ER et al (2007) Analysis of flavonoids in flower petals of soybean near-isogenic lines for flower and pubescence color genes. J Hered 98:250–257

    Article  CAS  PubMed  Google Scholar 

  23. Iwashina T, Oyoo ME, Khan NA et al (2008) Analysis of flavonoids in flower petals of soybean flower color variants. Crop Sci 48:1918–1924

    Article  CAS  Google Scholar 

  24. Zabala G, Vodkin LO (2005) The wp mutation of Glycine max carries a gene-fragment-rich transposon of the CACTA superfamily. Plant Cell 17:2619–2632

    Article  CAS  PubMed  Google Scholar 

  25. Todd JJ, Vodkin LO (1993) Pigmented soybean (Glycine max) seed coats accumulate proanthocyanidins during development. Plant Physiol 102:663–670

    CAS  PubMed  Google Scholar 

  26. Kovinich N, Saleem A, Arnason JT, Miki B (2010) Functional characterization of a UDP-glucose:flavonoid 3-O-glucosyltransferase from the seed coat of black soybean (Glycine max (L.) Merr). Phytochemistry 71:1253–1263

    Google Scholar 

  27. Takahashi R, Matsumura H, Oyoo ME et al (2008) Genetic and linkage analysis of purpleblue flower in soybean. J Hered 99:593–597

    Article  CAS  PubMed  Google Scholar 

  28. Ryu SN, Park SZ, Ho C-T (1998) High performance liquid chromatographic determination of anthocyanin pigments in some varieties of black rice. J Food Drug Anal 6:729–736

    CAS  Google Scholar 

  29. Stintzing FC, Stintzing AS, Carle R et al (2002) A novel zwitterionic anthocyanin from evergreen blackberry (Rubus laciniatus Willd). J Agric Food Chem 50:396–399

    Article  CAS  PubMed  Google Scholar 

  30. Wu X, Beecher GR, Holden JM et al (2006) Concentrations of anthocyanins in common foods in the United States and estimation of normal consumption. J Agric Food Chem 54:4069–4075

    Article  CAS  PubMed  Google Scholar 

  31. Markham KR, Bloor SJ, Nicholson R et al (2004) Black flower coloration in wild Lisianthius nigrescens: its chemistry and ecological consequences. Z Naturforsch C 59:625–630

    CAS  Google Scholar 

  32. Shibata M, Ishikura N (1960) Paper chromatographic survey of anthocyanin in tulipflowers. I Jap J Bot 17:230–238

    Google Scholar 

  33. Takeoka GR, Dao LT, Full GH et al (1997) Characterization of black bean (Phaseolus vulgaris L.) anthocyanins. J Agric Food Chem 45:3395–3400

    Article  CAS  Google Scholar 

  34. Stintzing FC, Stintzing AS, Carle R et al (2002) Color and antioxidant properties of cyanidin-based anthocyanin pigments. J Agric Food Chem 50:6172–6181

    Article  CAS  PubMed  Google Scholar 

  35. Goto T, Takase S, Kondo T (1978) PMR spectra of natural acylated anthocyanins. Determination of the stereostructure of awobanin, shisonin and violanin. Tetrahedron Lett 27:2413–2416

    Article  Google Scholar 

  36. Butelli E, Titta L, Giorgio M et al (2008) Enrichment of tomato fruit with health-promoting anthocyanins by expression of select transcription factors. Nat Biotechnol 26:1301–1308

    Article  CAS  PubMed  Google Scholar 

  37. Gonnet JF (2003) Origin of the color of Cv. rhapsody in blue rose and some other so-called “blue” roses. J Agric Food Chem 51:4990–4994

    Article  CAS  PubMed  Google Scholar 

  38. Markham KR, Gould KS, Winefield CS et al (2000) Anthocyanic vacuolar inclusions – their nature and significance in flower colouration. Phytochem 55:327–336

    Article  CAS  Google Scholar 

  39. Pourcel L, Irani NG, Lu Y et al (2010) The formation of anthocyanic vacuolar inclusions in arabidopsis thaliana and implications for the sequestration of anthocyanin pigments. Molec Plant 3(1):78–90

    Article  CAS  Google Scholar 

  40. Zhang H, Wang L, Deroles S et al (2006) New insight into the structures and formation of anthocyanic vacuolar inclusions in flower petals. BMC Plant Biol 6:29

    Article  PubMed  Google Scholar 

  41. Brouillard R, Dangles O (1994) Flavonoids and flower colour. In: Harborne JB (ed) The flavonoids-advances in research since 1986. CRC Press, Boca Raton, FL

    Google Scholar 

  42. Lepiniec L, Debeaujon I, Routaboul JM et al (2006) Genetics and biochemistry of seed flavonoids. Annu Rev Plant Biol 57:405–430

    Article  CAS  PubMed  Google Scholar 

  43. Dixon RA, Xie DY, Sharma SB (2005) Proanthocyanidins – a final frontier in flavonoid research? New Phytol 165:9–28

    Article  CAS  PubMed  Google Scholar 

  44. Pourcel L, Routaboul JM, Cheynier V et al (2007) Flavonoid oxidation in plants: from biochemical properties to physiological functions. Trends Plant Sci 12:29–36

    Article  CAS  PubMed  Google Scholar 

  45. Pourcel L, Routaboul JM, Kerhoas L et al (2005) TRANSPARENT TESTA10 encodes a laccase-like enzyme involved in oxidative polymerization of flavonoids in Arabidopsis seed coat. Plant Cell 17:2966–2980

    Article  CAS  PubMed  Google Scholar 

  46. Takahata Y, Ohnishi-Kameyama M, Furuta S et al (2001) Highly polymerized procyanidins in brown soybean seed coat with a high radical-scavenging activity. J Agric Food Chem 49:5843–5847

    Article  CAS  PubMed  Google Scholar 

  47. OECD (1993) Safety evaluation of foods derived by modern biotechnology, concepts and principles. Org Econ Coop Dev, Paris

    Google Scholar 

  48. Richards HA, Han CT, Hopkins RG et al (2003) Safety assessment of recombinant green fluorescent protein orally administered to weaned rats. J Nutr 133:1909–1912

    CAS  PubMed  Google Scholar 

Download references

Acknowledgments

The authors thank Dr. Ammar Saleem (University of Ottawa) for his assistance with HPLC, Dr. Shea Miller for performing the microscopy, and Drs. Malcolm Morrison and Elroy Cober (Agriculture and Agri-Food Canada) for providing seeds and for their helpful discussions. We would also like to thank the reviewers for their helpful suggestions. The research was supported by an NSERC Discovery Grant and AAFC project (RBPI 126) to BM.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Nikola Kovinich .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2011 Springer Science+Business Media, LLC

About this chapter

Cite this chapter

Kovinich, N., Arnason, J.T., De Luca, V., Miki, B. (2011). Coloring Soybeans with Anthocyanins?. In: Gang, D. (eds) The Biological Activity of Phytochemicals. Recent Advances in Phytochemistry, vol 41. Springer, New York, NY. https://doi.org/10.1007/978-1-4419-7299-6_4

Download citation

Publish with us

Policies and ethics