General Introduction to Glucosinolates

Advances in Botanical Research

Volumn 80, Issue , 2016, Pages 1-14

  Halkier, B A ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Biosynthetic pathway; Engineering; Localization; Storage; Transport

Indexed keywords

EID: 84997525170     PISSN: 00652296     EISSN: None     Source Type: Book Series    
DOI: 10.1016/bs.abr.2016.07.001     Document Type: Article

References (48)

1. Agerbirk, N., Olsen, C.E., Glucosinolate structures in evolution. Phytochemistry 77 (2012), 16–45.
2. Agerbirk, N., Olsen, C.E., Glucosinolate hydrolysis products in the crucifer Barbarea vulgaris include a thiazolidine-2-one from a specific phenolic isomer as well as oxazolidine-2-thiones. Phytochemistry 115 (2015), 143–151.
3. Andersen, T.G., Nour-Eldin, H.H., Fuller, V.L., Olsen, C.E., Burow, M., Halkier, B.A., Integration of biosynthesis and long-distance transport establish organ-specific glucosinolate profiles in vegetative Arabidopsis. The Plant Cell 25:8 (2013), 3133–3145.
4. Bennett, R.N., Kiddle, G., Wallsgrove, R.M., Biosynthesis of benzylglucosinolate, cyanogenic glucosides and phenylpropanoids in Carica papaya. Phytochemistry 45:1 (1997), 59–66.
5. Cartea, M.E., Velasco, P., Glucosinolates in Brassica foods: bioavailability in food and significance for human health. Phytochemistry Reviews 7:2 (2008), 213–229.
6. Chen, S., Glawischnig, E., Jørgensen, K., Naur, P., Jørgensen, B., Olsen, C.E., Halkier, B.A., CYP79F1 and CYP79F2 have distinct functions in the biosynthesis of aliphatic glucosinolates in Arabidopsis. The Plant Journal 33:5 (2003), 923–937.
7. Chen, S., Halkier, B.A., Characterization of glucosinolate uptake by leaf protoplasts of Brassica napus. Journal of Biological Chemistry 275:30 (2000), 22955–22960.
8. Douglas Grubb, C., Zipp, B.J., Ludwig-Müller, J., Masuno, M.N., Molinski, T.F., Abel, S., Arabidopsis glucosyltransferase UGT74B1 functions in glucosinolate biosynthesis and auxin homeostasis. The Plant Journal 40:6 (2004), 893–908.
9. Du, L., Lykkesfeldt, J., Olsen, C.E., Halkier, B.A., Involvement of cytochrome P450 in oxime production in glucosinolate biosynthesis as demonstrated by an in vitro microsomal enzyme system isolated from jasmonic acid-induced seedlings of Sinapis alba L. Proceedings of the National Academy of Sciences of the United States of America 92:26 (1995), 12505–12509.
10. Ettlinger, M., Kjaer, A., Sulfur compounds in plants. Recent Advances in Phytochemistry, 1(59), 1968, 144.
11. Ettlinger, M.G., Lundeen, A.J., The structures of sinigrin and sinalbin; an enzymatic rearrangement. Journal of the American Chemical Society 78:16 (1956), 4172–4173.
12. Fahey, J.W., Zalcmann, A.T., Talalay, P., The chemical diversity and distribution of glucosinolates and isothiocyanates among plants. Phytochemistry 56:1 (2001), 5–51.
13. Fahey, J.W., Zhang, Y., Talalay, P., Broccoli sprouts: an exceptionally rich source of inducers of enzymes that protect against chemical carcinogens. Proceedings of the National Academy of Sciences 94:19 (1997), 10367–10372.
14. Geu-Flores, F., Nielsen, M.T., Nafisi, M., Møldrup, M.E., Olsen, C.E., Motawia, M.S., Halkier, B.A., Glucosinolate engineering identifies a γ-glutamyl peptidase. Nature Chemical Biology 5:8 (2009), 575–577.
15. Gijzen, M., McGregor, I., Séguin-Swartz, G., Glucosinolate uptake by developing rapeseed embryos. Plant Physiology 89:1 (1989), 260–263.
16. Gimsing, A.L., Kirkegaard, J.A., Glucosinolates and biofumigation: fate of glucosinolates and their hydrolysis products in soil. Phytochemistry Reviews 8:1 (2009), 299–310.
17. Halkier, B.A., Du, L., The biosynthesis of glucosinolates. Trends in Plant Science 2:11 (1997), 425–431.
18. Halkier, B.A., Gershenzon, J., Biology and biochemistry of glucosinolates. Annual Review of Plant Biology 57 (2006), 303–333.
19. Hansen, C.H., Du, L., Naur, P., Olsen, C.E., Axelsen, K.B., Hick, A.J., Halkier, B.A., CYP83B1 is the oxime-metabolizing enzyme in the glucosinolate pathway in Arabidopsis. Journal of Biological Chemistry 276:27 (2001), 24790–24796.
20. Johnson, S.D., Griffiths, M.E., Peter, C.I., Lawes, M.J., Pollinators, “mustard oil” volatiles, and fruit production in flowers of the dioecious tree Drypetes natalensis (Putranjivaceae). American Journal of Botany 96:11 (2009), 2080–2086.
21. Jørgensen, M.E., Nour-Eldin, H.H., Halkier, B.A., Transport of defense compounds from source to sink: lessons learned from glucosinolates. Trends in Plant Science 20:8 (2015), 508–514.
22. Kaul, S., Koo, H.L., Jenkins, J., Rizzo, M., Rooney, T., Tallon, L.J., Lin, X., Analysis of the genome sequence of the flowering plant Arabidopsis thaliana. Nature 408:6814 (2000), 796–815.
23. Kliebenstein, D.J., Lambrix, V.M., Reichelt, M., Gershenzon, J., Mitchell-Olds, T., Gene duplication in the diversification of secondary metabolism: tandem 2-oxoglutarate–dependent dioxygenases control glucosinolate biosynthesis in Arabidopsis. The Plant Cell 13:3 (2001), 681–693.
24. Koroleva, O.A., Gibson, T.M., Cramer, R., Stain, C., Glucosinolate-accumulating S-cells in Arabidopsis leaves and flower stalks undergo programmed cell death at early stages of differentiation. The Plant Journal 64:3 (2010), 456–469.
25. Kroymann, J., Textor, S., Tokuhisa, J.G., Falk, K.L., Bartram, S., Gershenzon, J., Mitchell-Olds, T., A gene controlling variation in Arabidopsis glucosinolate composition is part of the methionine chain elongation pathway. Plant Physiology 127:3 (2001), 1077–1088.
26. Madsen, S.R., Olsen, C.E., Nour-Eldin, H.H., Halkier, B.A., Elucidating the role of transport processes in leaf glucosinolate distribution. Plant Physiology 166:3 (2014), 1450–1462.
27. Magrath, R., Bano, F., Morgner, M., Parkin, I., Sharpe, A., Lister, C., Mithen, A., Genetics of aliphatic glucosinolates. I. Side chain elongation in Brassica napus and Arabidopsis thaliana. Heredity 72 (1994), 290–299.
28. Magrath, R., Mithen, R., Maternal effects on the expression of individual aliphatic glucosinolates in seeds and seedlings of Brassica napus. Plant Breeding 111:3 (1993), 249–252.
29. Mailer, R.J., McFadden, A., Ayton, J., Redden, B., Anti-nutritional components, fibre, sinapine and glucosinolate content, in Australian canola (Brassica napus L.) meal. Journal of the American Oil Chemists’ Society 85:10 (2008), 937–944.
30. Meyerowitz, E.M., Prehistory and history of Arabidopsis research. Plant Physiology 125:1 (2001), 15–19.
31. Mikkelsen, M.D., Buron, L.D., Salomonsen, B., Olsen, C.E., Hansen, B.G., Mortensen, U.H., Halkier, B.A., Microbial production of indolylglucosinolate through engineering of a multi-gene pathway in a versatile yeast expression platform. Metabolic Engineering 14:2 (2012), 104–111.
32. Mikkelsen, M.D., Hansen, C.H., Wittstock, U., Halkier, B.A., Cytochrome P450 CYP79B2 from Arabidopsis catalyzes the conversion of tryptophan to indole-3-acetaldoxime, a precursor of indole glucosinolates and indole-3-acetic acid. Journal of Biological Chemistry 275:43 (2000), 33712–33717.
33. Mikkelsen, M.D., Olsen, C.E., Halkier, B.A., Production of the cancer-preventive glucoraphanin in tobacco. Molecular Plant 3:4 (2010), 751–759.
34. Mirza, N., Crocoll, C., Olsen, C.E., Halkier, B.A., Engineering of methionine chain elongation part of glucoraphanin pathway in E. coli. Metabolic Engineering, 35, 2015.
35. Mithen, R., Development and commercialisation of ‘Beneforte’ broccoli and potential health benefits. Paper presented at the VI International Symposium on Brassicas and XVIII Crucifer Genetics Workshop 1005, 2012.
36. Møller, B.L., Functional diversifications of cyanogenic glucosides. Current Opinion in Plant Biology 13:3 (2010), 337–346.
37. Nafisi, M., Sønderby, I.E., Hansen, B.G., Geu-Flores, F., Nour-Eldin, H.H., Nørholm, M.H.H., Halkier, B.A., Cytochromes P450 in the biosynthesis of glucosinolates and indole alkaloids. Phytochemistry Reviews 5:2 (2006), 331–346.
38. Nour-Eldin, H.H., Andersen, T.G., Burow, M., Madsen, S.R., Jørgensen, M.E., Olsen, C.E., Halkier, B.A., NRT/PTR transporters are essential for translocation of glucosinolate defence compounds to seeds. Nature 488:7412 (2012), 531–534.
39. Pfalz, M., Mikkelsen, M.D., Bednarek, P., Olsen, C.E., Halkier, B.A., Kroymann, J., Metabolic engineering in Nicotiana benthamiana reveals key enzyme functions in Arabidopsis indole glucosinolate modification. The Plant Cell 23:2 (2011), 716–729.
40. Reintanz, B., Lehnen, M., Reichelt, M., Gershenzon, J., Kowalczyk, M., Sandberg, G., Palme, K., Bus, a bushy Arabidopsis CYP79F1 knockout mutant with abolished synthesis of short-chain aliphatic glucosinolates. The Plant Cell 13:2 (2001), 351–367.
41. Rodman, J., Soltis, P., Soltis, D., Sytsma, K., Karol, K., Parallel evolution of glucosinolate biosynthesis inferred from congruent nuclear and plastid gene phylogenies. American Journal of Botany, 85(7), 1998, 997.
42. Sivapalan, T., Melchini, A., Traka, M., Saha, S., Mithen, R., Investigating the bioavailability of phytochemicals and minerals from broccoli soups. Proceedings of the Nutrition Society, 74(OCE3), 2015, E191.
43. Sønderby, I.E., Geu-Flores, F., Halkier, B.A., Biosynthesis of glucosinolates – gene discovery and beyond. Trends in Plant Science 15:5 (2010), 283–290.
44. Tantikanjana, T., Mikkelsen, M.D., Hussain, M., Halkier, B.A., Sundaresan, V., Functional analysis of the tandem-duplicated P450 genes SPS/BUS/CYP79F1 and CYP79F2 in glucosinolate biosynthesis and plant development by Ds transposition-generated double mutants. Plant Physiology 135:2 (2004), 840–848.
45. Traka, M., Mithen, R., Glucosinolates, isothiocyanates and human health. Phytochemistry Reviews 8:1 (2009), 269–282.
46. ® broccoli. New Phytologist 198:4 (2013), 1085–1095.
47. Underhill, E.W., Wetter, L.R., Chisholm, M.D., Biosynthesis of glucosinolates. Biochemical Society Symposium 38 (1973), 303–326.
48. Wittstock, U., Halkier, B.A., Glucosinolate research in the Arabidopsis era. Trends in Plant Science 7:6 (2002), 263–270.