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.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Lemaux PG (2008) Genetically engineered plants and foods: a scientist’s analysis of the issues (Part I). Annu Rev Plant Biol 59:771–812
Doyle A (2008) EMBARGOED – World fails to monitor biotech trade – UN study. Williams R (ed). Thomson Reuters
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
Tanaka Y, Katsumoto Y, Brugliera F et al (2005) Genetic engineering in floriculture. Plant Cell, Tiss and Org Cult 80:1–24
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
Holton T, Tanaka Y (1994) Blue roses-a pigment of our imagination? Trends Biotechnol 12:40–42
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
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
Springob K, Nakajima J, Yamazaki M et al (2003) Recent advances in the biosynthesis and accumulation of anthocyanins. Nat Prod Rep 20:288–303
Bernard RL, Weiss MG (1973) Qualitative genetics. In: Caldwell BE (ed) Soybeans: improvement, production, and uses, 1st edn. Am Soc Agron, Wisconsin
Palmer RG, Kilen TC (1987) Qualitative genetics and cytogenetics. In: Wilcox JR (ed) Soybeans: improvement, production and uses, 1st edn. Am Soc Agron, Wisconsin
Tuteja JH, Vodkin LO (2008) Structural features of the endogenous CHS silencing and target loci in the soybean genome. Crop Sci 48:S49–S68
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
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
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
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
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
Buzzell R, Buttery B, MacTavish D (1987) Biochemical genetics of black pigmentation of soybean seed. The J Hered 78:53–54
Saslowsky D, Winkel-Shirley B (2001) Localization of flavonoid enzymes in Arabidopsis roots. Plant J 27:37–48
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
Zabala G, Vodkin LO (2007) A rearrangement resulting in small tandem repeats in the F3′5′H gene of white flower genotypes is associated with the soybean W1 locus. Plant Genome 47:S113–S124
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
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
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
Todd JJ, Vodkin LO (1993) Pigmented soybean (Glycine max) seed coats accumulate proanthocyanidins during development. Plant Physiol 102:663–670
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
Takahashi R, Matsumura H, Oyoo ME et al (2008) Genetic and linkage analysis of purpleblue flower in soybean. J Hered 99:593–597
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
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
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
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
Shibata M, Ishikura N (1960) Paper chromatographic survey of anthocyanin in tulipflowers. I Jap J Bot 17:230–238
Takeoka GR, Dao LT, Full GH et al (1997) Characterization of black bean (Phaseolus vulgaris L.) anthocyanins. J Agric Food Chem 45:3395–3400
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
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
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
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
Markham KR, Gould KS, Winefield CS et al (2000) Anthocyanic vacuolar inclusions – their nature and significance in flower colouration. Phytochem 55:327–336
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
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
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
Lepiniec L, Debeaujon I, Routaboul JM et al (2006) Genetics and biochemistry of seed flavonoids. Annu Rev Plant Biol 57:405–430
Dixon RA, Xie DY, Sharma SB (2005) Proanthocyanidins – a final frontier in flavonoid research? New Phytol 165:9–28
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
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
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
OECD (1993) Safety evaluation of foods derived by modern biotechnology, concepts and principles. Org Econ Coop Dev, Paris
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
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
Corresponding author
Editor information
Editors and Affiliations
Rights 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
DOI: https://doi.org/10.1007/978-1-4419-7299-6_4
Published:
Publisher Name: Springer, New York, NY
Print ISBN: 978-1-4419-6961-3
Online ISBN: 978-1-4419-7299-6
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)