New genes in alkaloid metabolism and transport

Current Opinion in Biotechnology

Volumn 14, Issue 2, 2003, Pages 163-168

  Hashimoto, Takashi ^a   Yamada, Yasuyuki ^a  

^a NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

Maltose binding protein; MBP; MDR; Multidrug resistance

Indexed keywords

ACRIDONE DERIVATIVE; ALKALOID; BERBERINE; CAFFEINE; COMPLEMENTARY DNA; ENZYME; INDOLE ALKALOID; ISOQUINOLINE ALKALOID; MORPHINE; NICOTINE; NICOTINE DERIVATIVE; PALMATINE; PURINE DERIVATIVE; PYRROLIZIDINE DERIVATIVE; TERPENE DERIVATIVE; TROPANE ALKALOID; VEGETABLE PROTEIN;

ARABIDOPSIS; BIOSYNTHESIS; CATABOLISM; DRUG SYNTHESIS; DRUG TRANSPORT; ENZYME SPECIFICITY; GENE FUNCTION; GENETIC ENGINEERING; HETEROLOGOUS EXPRESSION; MOLECULAR CLONING; NONHUMAN; PLANT; PLANT GENETICS; PLANT METABOLISM; PRIORITY JOURNAL; REGULATORY MECHANISM; REVIEW; SEQUENCE HOMOLOGY;

ARABIDOPSIS;

EID: 0038742851     PISSN: 09581669     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0958-1669(03)00027-2     Document Type: Review

References (51)

1. Kutchan T: Alkaloids. In Biochemistry & Molecular Biology of Plants. Edited by Buchanan BB, Gruissem W, Jones RL. Rockville: American Society of Plant Physiologists; 2000:1268-1286.
2. Raskin I., Ribnicky D.M., Komarnytsky S., Ilic N., Poulev A., Borisjuk N., Brinker A., Moreno D.A., Ripoll C., Yakoby N.et al. Plants and human health in the twenty-first century. Trends Biotechnol. 20:2002;522-531 An interesting review of botanical therapeutics, including plant-derived pharmaceuticals. Extensive coverage of market and regulatory issues makes this short review unique among related articles.
3. De Luca V., Laflamme P. The expanding universe of alkaloid biosynthesis. Curr. Opin. Plant Biol. 4:2001;225-233 An excellent review on the progress of alkaloid biosynthesis research from 1999 to mid-2001. Biosynthesis of monoterpenoid, isoquinoline, and other alkaloids is covered, as are compartmentation and regulation. Our current review avoids overlaps with this review as much as possible.
4. Facchini P.J. Alkaloid biosynthesis in plants: biochemistry, cell biology, molecular regulation, and metabolic engineering application. Annu. Rev. Plant Physiol. Plant Mol. Biol. 52:2001;29-66 A comprehensive review of alkaloid biosynthesis, including enzymes, intracellular and intercellular metabolite flow, gene regulation, and application to metabolic engineering. For findings up to the end of 2000, interested readers should refer to this article.
5. Choi K., Morishige T., Shitan N., Yazaki K., Sato F. Molecular cloning and characterization of coclaurine N-methyltransferase from cultured cells of Coptis japonica. J. Biol. Chem. 277:2002;830-835.
6. Morishige T., Dubouzet E., Choi K., Yazaki K., Sato F. Molecular cloning of columbamine O-methyltransferase from cultured Coptis japonica cells. Eur. J. Biochem. 269:2002;5659-5667.
7. Grothe T., Lenz R., Kutchan T. Molecular characterization of the salutaridinol 7-O-acetyltransferase involved in morphine biosynthesis in opium poppy Papaver somniferum. J. Biol. Chem. 276:2001;30717-30723.
8. Ogawa M., Herai Y., Koizumi N., Kusano T., Sano H. 7-Methylxanthine methyltransferase of coffee plants. J. Biol. Chem. 276:2001;8213-8218.
9. Mizuno K., Okuda A., Kato M., Yoneyama N., Tanaka H., Ashihara H., Fujimura T. Isolation of a new dual-functional caffeine synthase gene encoding an enzyme for the conversion of 7-methylxanthine to caffeine from coffee (Coffea arabica L.). FEBS Lett. 534:2003;75-81.
10. Uefuji H, Ogita S, Yamaguchi Y, Koizumi N, Sano H: Molecular cloning and functional characterization of three distinct N-methyltransferases involved in the caffeine biosynthetic pathway in coffee plants. Plant Physiol 2003, in press.
11. Walker K., Long R., Croteau R. The final step in Taxol biosynthesis: cloning of the taxoid C13-side-chain N-benzoyltransferase from Taxus. Proc. Natl. Acad Sci. USA. 99:2002;9166-9171.
12. Hibi N., Higashiguchi S., Hashimoto T., Yamada Y. Gene expression in tobacco low-nicotine mutants. Plant Cell. 6:1994;723-735.
13. van der Fits L., Memelink J. ORCA3, a jasmonate-responsive transcriptional regulator of plant primary and secondary metabolism. Science. 289:2000;295-297.
14. Naumann C., Hartmann T., Ober D. Evolutionary recruitment of a flavin-dependent monooxygenase for the detoxification of host plant-acquired pyrrolizidine alkaloids in the alkaloid-defended arctiid moth Tyria jacobaeae. Proc. Natl. Acad Sci. USA. 99:2002;6085-6090 Larvae of a herbivorous insect feed on pyrrolizidine alkaloid-containing Senecio plants and detoxify the ingested alkaloids by N-oxidation. Molecular cloning of the N-oxygenase revealed its evolutionary origin to be the pre-existing flavin-dependent monooxygenase family. This is another side of the co-evolutionary story between alkaloid-producing plants and feeding insects.
15. Delaney T., Uknes S., Vernooij B., Friedrich L., Weymann K., Negrotto D., Gaffney T., Gut-Rella M., Kessmann H., Ward E.et al. A central role of salicylic acid in plant disease resistance. Science. 266:1994;1247-1250.
16. Bresler M., Rosser S., Basran A., Bruce N. Gene cloning and nucleotide sequencing and properties of a cocaine esterase from Rhodococcus sp. strain MB1. Appl. Env. Microbiol. 66:2000;904-908.
17. Baitsch D., Sandu C., Brandsch R., Igloi G. Gene cluster on pAO1 of Arthrobacter nicotinovorans involved in degradation of the plant alkaloid nicotine: cloning, purification, and characterization of 2,6-dihydroxypyridine 3-hydroxylase. J. Bacteriol. 183:2001;5262-5267.
18. Holt P., Bruce N., Lowe C. Bioluminescent assay for heroin and its metabolites. Anal. Chem. 68:1996;1877-1882.
19. Shoji T., Yamada Y., Hashimoto T. Jasmonate induction of putrescine N-methyltransferase genes in the root of Nicotiana sylvestris. Plant Cell Physiol. 41:2000;831-839.
20. Shoji T., Winz R., Iwase T., Nakajima K., Yamada Y., Hashimoto T. Expression patterns of two tobacco isoflavone reductase-like genes and their possible roles in secondary metabolism in tobacco. Plant Mol. Biol. 50:2002;427-440.
21. Wink M, Roberts M: Compartmentation of alkaloid synthesis, transport, and storage. In Alkaloids. Edited by Roberts M, Wink M. New York: Plenum Press; 1998:301-307.
22. Sakai K., Shitan N., Sato F., Ueda K., Yazaki K. Characterization of berberine transport into Coptis japonica cells and the involvement of ABC protein. J. Exp. Bot. 53:2002;1879-1886.
23. Hsieh P., Siegel S., Rogers B., Davis D., Lewis K. Bacteria lacking a multidrug pump: a sensitive tool for drug discovery. Proc. Natl. Acad. Sci. USA. 95:1998;6602-6606.
24. Li L., He Z., Pandey G., Tsuchiya T., Luan S. Functional cloning and characterization of a plant efflux carrier for multidrug and heavy metal detoxification. J. Biol. Chem. 277:2002;5360-5368.
25. Morita Y., Kodama K., Shiota S., Mine T., Kataoka A., Mizushima T., Tsuchiya T. MorM, a putative multidrug efflux protein, of Vibrio parahaemolyticus and its homolog in Esherichia coli. Antimicrob. Agents Chemother. 42:1998;1778-1782.
26. Stermitz F., Lorenz P., Tawara J., Zenewicz L., Lewis K. Synergy in a medicinal plant: antimicrobial action of berberine potentiated by 5′-methoxyhydnocarpin, a multidrug pump inhibitor. Proc. Natl. Acad Sci. USA. 97:2000;1433-1437.
27. Shitan N., Bazin I., Dan K., Obata K., Kigawa K., Ueda K., Sato F., Forestier C., Yazaki K. Involvement of CjMDR1, a plant multidrug-resistance-type ATP-binding cassette protein, in alkaloid transport in Coptis japonica. Proc. Natl. Acad Sci. USA. 100:2003;751-756 MDR pumps are likely candidates for alkaloid transport within or between berberine-producing Coptis cells. This detailed functional characterization of one such pump indicates that the transporter pumps berberine into xylem cells for root-to-rhizome translocation.
28. Fehr M., Frommer W., Lalonde S. Visualization of maltose uptake in living yeast cells by fluorescent nanosensors. Proc. Natl. Acad Sci. USA. 99:2002;9846-9851 In vivo metabolite imaging at the cellular or subcellular level is an exciting but undeveloped technique for non-destructive and real-time monitoring of metabolite distribution. Promising fluorescent nanosensors were engineered to visualize maltose uptake in living yeast cells. This study will stimulate similar and further developments of such nanosensors for other metabolites.
29. Sato F., Hashimoto T., Hachiya A., Tamura K., Choi K., Morishige T., Fujimoro H., Yamada Y. Metabolic engineering of plant alkaloid biosynthesis. Proc. Natl. Acad Sci. USA. 98:2001;367-372 This paper reports typical outcomes of pathway engineering by overexpressing or downregulating select genes for enzymes involved in the biosynthesis of scopolamine, nicotine, and berberine. The resulting metabolic changes were modest, and in one case the accumulating pathway intermediates channeled into a related branch pathway, thereby causing abnormal plant morphologies.
30. Nakajima K., Hashimoto T., Yamada Y. Two tropinone reductases with different stereospecificities are short-chain dehydrogenases evolved from a common ancestor. Proc. Natl. Acad Sci. USA. 90:1993;9591-9595.
31. Keiner R., Kaiser H., Nakajima K., Hashimoto T., Dräger B. Molecular cloning, expression and characterization of tropinone reductase II, an enzyme of the SDR family in Solanum tuberosum (L.). Plant Mol. Biol. 48:2002;299-308.
32. Matsuda J., Okabe S., Hashimoto T., Yamada Y. Molecular cloning of hyoscyamine 6β-hydroxylase, a 2-oxoglutarate-dependent dioxygenase, from cultured roots of Hyoscyamus niger. J. Biol. Chem. 266:1991;9460-9464.
33. Facchini P., De Luca V. Differential and tissue-specific expression of a gene family for tyrosine/dopa decarboxylase in opium poppy. J. Biol. Chem. 269:1994;26684-26690.
34. Dittrich H., Kutchan T. Molecular cloning, expression, and induction of berberine bridge enzyme, an enzyme essential to the formation of benzophenanthridine alkaloids in the response of plants to pathogen attack. Proc. Natl. Acad Sci. USA. 88:1991;9969-9973.
35. Morishige T., Tsujita T., Yamada Y., Sato F. Molecular characterization of the S-adenosyl-L-methionine: 3′-hydroxy-N-methylcoclaurine 4′-O-methyltransferase of isoquinoline alkaloid biosynthesis in Coptis japonica. J. Biol. Chem. 275:2000;23398-23405.
36. Takeshita N., Fujiwara H., Mimura H., Fitchen J., Yamada Y., Sato F. Molecular cloning and characterization of S-adenosyl-L-methionine: scoulerine 9-O-methyltransferase from cultured cells of Coptis japonica. Plant Cell Physiol. 36:1995;29-36.
37. Frick S., Kutchan T. Molecular cloning and functional expression of O-methyltransferases common to isoquinoline alkaloid and phenylpropanoid biosynthesis. Plant J. 17:1999;329-339.
38. Pauli H., Kutchan T. Molecular cloning and functional heterologous expression of two alleles encoding (S)-N-methylcoclaurine 3′-hydroxylase (CYP80B1), a new methyl jasmonate-inducible cytochrome P450-dependent mono-oxygenase of benzylisoquinoline alkaloid biosynthesis. Plant J. 13:1998;793-801.
39. Kraus P., Kutchan T. Molecular cloning and heterologous expression of a cDNA encoding berbamunine synthase, a C-O phenol-coupling cytochrome P450 from the higher plant Berberis stolonifera. Proc. Natl. Acad Sci. USA. 92:1995;2071-2075.
40. Unterlinner B., Lenz R., Kutchan T. Molecular cloning and functional expression of codeinone reductase: the penultimate enzyme in morphine biosynthesis in the opium poppy Papaver somniferum. Plant. J. 18:1999;465-475.
41. De Luca V., Marineau C., Brisson N. Molecular cloning and analysis of a cDNA encoding a plant tryptophan decarboxylase: comparison with animal dopa decarboxylase. Proc. Natl. Acad Sci. USA. 86:1989;2582-2586.
42. Irmler S., Schröder G., St-Pierre B., Crouch N., Hotze M., Schmidt J., Strack D., Matern U., Schröder J. Indole alkaloid biosynthesis in Catharanthus roseus: new enzyme activities and identification of cytochrome P450 CYP72A1 as secologanin synthase. Plant J. 24:2000;797-804.
43. Kutchan T., Hampp N., Lottspeich F., Beyreuther K., Zenk M. The cDNA clone for strictosidine synthase from Rauvolfia serpentian. FEBS Lett. 237:1988;40-44.
44. Geerlings A., Ibanez M., Memelink J., van der Heijden R., Verpoorte R. Molecular cloning and analysis of strictosidine β-D-glucosidase, an enzyme in terpenoid indole alkaloid biosynthesis in Catharanthus roseus. J. Biol. Chem. 275:2000;3051-3056.
45. Dogru E., Warzecha H., Seibel F., Haebel S., Lottspeich F., Stöckigt J. The gene encoding polyneuridine aldehyde esterase of monoterpenoid indole biosynthesis in plants is an ortholog of the α/β hydrolase super family. Eur. J. Biochem. 267:2000;1397-1406.
46. Schröder G., Unterbusch E., Kaltenbach M., Schmidt J., Strack D., De Luca V., Schröder J. Light-induced cytochrome P450-dependent enzyme in indole alkaloid biosynthesis: tabersonine 16-hydroxylase. FEBS Lett. 458:1999;97-102.
47. Vázquez-Flota F., De Carolis E., Alarco A., De Luca V. Molecular cloning and characterization of deacetoxyvindoline 4-hydroxylase, a 2-oxoglutarate-dependent dioxygenase involved in the biosynthesis of vindoline in Catharanthus roseus (L.) G. Don. Plant Mol. Biol. 34:1997;935-948.
48. St-Pierre B., Laflamme P., Alarco A., De Luca V. The terminal O-acetyltransferase involved in vindoline biosynthesis defines a new class of proteins responsible for coenzyme A-dependent acyl transfer. Plant J. 14:1998;703-713.
49. Kato M., Mizuno K., Crozier A., Fujimura T., Ashihara H. Caffeine synthase gene from tea leaves. Nature. 406:2000;956-957.
50. Ober D., Hartmann T. Homospermidine synthase, the first pathway-specific enzyme of pyrrolizidine alkaloid biosynthesis, evolved from deoxyhypusine synthase. Proc. Natl. Acad Sci. USA. 96:1999;14777-14782.
51. Lukacin R., Springob K., Urbanke C., Ernwein C., Schröder G., Schröder J., Matern U. Native acridone synthases I and II from Ruta graveolens L. form homodimers. FEBS Lett. 448:1999;135-140.