Detection and Quantification of Engineered Proanthocyanidins in Transgenic Plants

Natural Product Communications

Volumn 2, Issue 10, 2007, Pages

  Peel, Gregory J ^a   Dixon, Richard A ^a  

^a PLANT BIOLOGY DIVISION   (United States)

Author keywords

Condensed tannins; metabolic engineering; normal phase high performance liquid chromatography

Indexed keywords

EID: 36249009236     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578X0700201008     Document Type: Article

References (27)

1. Bagchi D, Garg A, Krohn RL, Bagchi M, Bagchi DJ, Balmoori J, Stohs SJ. (1998) Protective effects of grape seed proanthocyanidins and selected antioxidants against TPA-induced hepatic and brain lipid peroxidation and DNA fragmentation, and peritoneal macrophage activation in mice. General Pharmacology, 30, 771–776.
2. Belitz HD, Wieser H. (1985) Bitter compounds: occurrence and structure-activity relationships. Food Reviews International, 1, 271–354.
3. McMahon LR, McAllister TA, Berg BP, Majak W, Acharya SN, Popp JD, Coulman BE, Wang Y, Cheng KJ. (2000) A review of the effects of forage condensed tannins on ruminal fermentation and bloat in grazing cattle. Canadian Journal of Plant Science, 80, 469–485.
4. Xie D, Sharma SB, Paiva NL, Ferreira D, Dixon RA. (2003) Role of anthocyanidin reductase, encoded by BANYULS in plant flavonoid biosynthesis. Science, 299, 396–399.
5. Xie D, Dixon RA. (2005) Proanthocyanidin biosynthesis - still more questions than answers? Phytochemistry, 66, 2127–2144.
6. Porter LJ, Hrstich LN, Chan BG. (1985) The conversion of procyanidins and prodelphinidins to cyanidin and delphinidin. Phytochemistry, 25, 223–230.
7. Foo LY. (1984) Condensed tannins: co-occurrence of procyanidins, prodelphinidins and profisetinidins in the heartwood of Acacia baileyana. Phytochemistry, 23, 2915–2918.
8. Routaboul J-M, Kerhoas L, Debeaujon I, Pourcel L, Caboche M, Einhorn J, Lepiniec L. (2006) Flavonoid diversity and biosynthesis in seed of Arabidopsis thaliana. Planta, 224, 96–107.
9. Dixon RA, Xie D, Sharma SB. (2005) Proanthocyanidins - a final frontier in flavonoid research? New Phytologist, 165, 9–28.
10. Xie D, Sharma SB, Wright E, Wang Z, Dixon RA. (2006) Metabolic engineering of proanthocyanidins through co-expression of anthocyanidin reductase and the PAP1 MYB transcription factor. Plant Journal, 45, 895–907.
11. Sharma SB, Dixon RA. (2006) Metabolic engineering of proanthocyanidins by ectopic expression of transcription factors in Arabidopsis thaliana. Plant Journal, 44, 62–75.
12. Treutter D. (1989) Chemical reaction detection of catechins and proanthocyanidins with 4-dimethylaminocinnamaldehyde. Journal of Chromatography, 467, 185–193.
13. Treutter D, Feucht W, Santos-Buelga C. (1994) Determination of catechins and procyanidins in plant extracts - a comparison of methods. Acta Horticulturae, 381, 789–796.
14. de Pascual-Teresa S, Treutter D, Rivas-Gonzalo JC, Santos-Buelga C. (1998) Analysis of flavanols in beverages by high-performance liquid chromatography with chemical reaction detection. Journal of Agricultural and Food Chemistry, 46, 4209–4213.
15. Gu LW, Kelm M, Hammerstone JF, Beecher G, Cunningham D, Vannozzi S, Prior RL. (2002) Fractionation of polymeric procyanidins from lowbush blueberry and quantification of procyanidins in selected foods with an optimized normal-phase HPLC-MS fluorescent detection method. Journal of Agricultural and Food Chemistry, 50, 4852–4860.
16. Monagas M, Gomez CC, Bartolome B, Laureano O, da Ricardo SJM. (2003) Monomeric, oligomeric, and polymeric flavan-3-ol composition of wines and grapes from Vitis vinifera L. cv. Graciano, Tempranillo, and Cabernet Sauvignon. Journal of Agricultural and Food Chemistry, 51, 6475–6481.
17. Lazarus SA, Adamson GE, Hammerstone JF, Schmitz HH. (1999) High-performance liquid chromatography/mass spectrometry analysis of proanthocyanidins in foods and beverages. Journal of Agricultural and Food Chemistry, 47, 3693–3701.
18. Kelm MA, Johnson JC, Robbins RJ, Hammerstone JF, Schmitz HH. (2006) High-performance liquid chromatography separation and purification of cacao (Theobroma cacao L.) procyanidins according to degree of polymerization using a diol stationary phase. Journal of Agricultural and Food Chemistry, 54, 1571–1576.
19. Kennedy JA, Hayasaka Y, Vidal S, Waters EJ, Jones GP. (2001) Composition of grape skin proanthocyanidins at different stages of berry development. Journal of Agricultural and Food Chemistry, 49, 5348–5355.
20. Awika JM, Dykes L, Gu LW, Rooney LW, Prior RL. (2003) Processing of sorghum (Sorghum bicolor) and sorghum products alters procyanidin oligomer and polymer distribution and content. Journal of Agricultural and Food Chemistry, 51, 5516–5521.
21. Borevitz J, Xia Y, Blount JW, Dixon RA, Lamb C. (2000) Activation tagging identifies a conserved MYB regulator of phenylpropanoid biosynthesis. Plant Cell, 12, 2383–2393.
22. Nesi N, Jond C, Debeaujon I, Caboche M, Lepiniec L. (2001) 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.
23. Baudry A, Heim MA, Dubreucq B, Caboche M, Weisshaar B, Lepiniec L. (2004) TT2, TT8, and TTG1 synergistically specify the expression of BANYULS and proanthocyanidin biosynthesis in Arabidopsis thaliana. Plant Journal, 39, 366–380.
24. Abrahams S, Tanner GJ, Larkin PJ, Ashton AR. (2002) Identification and biochemical characterization of mutants in the proanthocyanidin pathway in Arabidopsis. Plant Physiology, 130, 561–576.
25. Gu LW, Kelm MA, Hammerstone JF, Beecher G, Holden J, Haytowitz D, Prior RL. (2003) Screening of foods containing proanthocyanidins and their structural characterization using LC-MS/MS and thiolytic degradation. Journal of Agricultural and Food Chemistry, 51, 7513–7521.
26. Modolo LV, Dixon RA, Blount JW, Achine L, Naoumkina MA. (2007) A functional genomics approach to (iso)flavonoid glycosylation in the model legume Medicago truncatula. Plant Molecular Biology, 64, 499–518.
27. Thomas MR, Johnson LB, White FF (1990) Selection of interspecific somatic hybrids of Medicago by using Agrobacterium -transformed tissue. Plant Science, 69, 189–198.