Purification, cloning, functional expression and characterization of perakine reductase: The first example from the AKR enzyme family, extending the alkaloidal network of the plant Rauvolfia

Plant Molecular Biology

Volumn 67, Issue 5, 2008, Pages 455-467

  Sun, Lianli ^a,b   Ruppert, Martin ^b   Sheludko, Yuri ^c   Warzecha, Heribert ^d   Zhao, Yu ^a   Stöckigt, Joachim ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b JOHANNES GUTENBERG UNIVERSITY   (Germany)

^c INSTITUTE OF CELL BIOLOGY AND GENETIC ENGINEERING   (Ukraine)

^d DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Aldo keto reductase; Functional expression; Indole alkaloid metabolic network; Perakine reductase; Rauvolfia serpentina (Apocynaceae)

Indexed keywords

ALCOHOL DEHYDROGENASE; CARBONYL REDUCTASE (NADPH); COMPLEMENTARY DNA; PERAKINE REDUCTASE, RAUVOLFIA SERPENTINA; PRIMER DNA; RAUWOLFIA ALKALOID; VEGETABLE PROTEIN;

AMINO ACID SEQUENCE; ARTICLE; CHEMISTRY; ENZYME SPECIFICITY; ENZYMOLOGY; GENETICS; ISOLATION AND PURIFICATION; METABOLISM; MOLECULAR CLONING; MOLECULAR GENETICS; NUCLEOTIDE SEQUENCE; RAUWOLFIA; SEQUENCE HOMOLOGY;

ALCOHOL OXIDOREDUCTASES; AMINO ACID SEQUENCE; BASE SEQUENCE; CLONING, MOLECULAR; DNA PRIMERS; DNA, COMPLEMENTARY; MOLECULAR SEQUENCE DATA; PLANT PROTEINS; RAUWOLFIA; SECOLOGANIN TRYPTAMINE ALKALOIDS; SEQUENCE HOMOLOGY, AMINO ACID; SUBSTRATE SPECIFICITY;

APOCYNACEAE; ESCHERICHIA COLI; RAUVOLFIA; RAUVOLFIA SERPENTINA;

EID: 45049087049     PISSN: 01674412     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11103-008-9331-7     Document Type: Article

References (32)

1. Bashir K, Inoue H, Nagasaka S, Takahashi M, Nakanishi H, Mori S, Nishizawa NK (2006) Cloning and characterization of deoxymugineic acid synthase genes from graminaceous plants. J Biol Chem 281:32395-32402
2. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248-254
3. Croteau R, Ketchum REB, Long RM, Kaspera R, Wildung MR (2006) Taxol biosynthesis and molecular genetics. Phytochem Rev 5:75-97
4. De-Eknamkul W, Ounaroon A, Tanahashi T, Kutchan TM, Zenk MH (1997) Enzymatic condensation of dopamine and secologanin by cell-free extracts of Alangium lamarckii. Phytochemistry 45:477-484
5. De-Eknamkul W, Suttipanta N, Kutchan TM (2000) Purification and characterization of deacetylipecoside synthase from Alangium lamarckii Thw. Phytochemistry 55:177-181
6. Di Luccio E, Elling RA, Wilson DK (2006) Identification of a novel NADH-specific aldo-keto reductase using sequence and structural homologies. Biochem J 400:105-114
7. Dogru E, Warzecha H, Seibel F, Haebel S, Lottspeich F, Stöckigt J (2000) The gene encoding polyneuridine aldehyde esterase of monoterpenoid indole alkaloid biosynthesis in plants is an ortholog of the α/β hydrolase super family. Eur J Biochem 267:1397-1406
8. Falkenhagen H, Polz L, Takayama H, Kitajima M, Sakai S-I, Aimi N, Stöckigt J (1995) Substrate specificity of vinorine hydroxylase, a novel membrane-bound key enzyme of Rauvolfia indole alkaloid biosynthesis. Heterocycles 41:2683-2690
9. Gavidia I, Perez-Bermudez P, Seitz HU (2002) Cloning and expression of two novel aldo-keto reductases from Digitalis purpurea leaves. Eur J Biochem 269:2842-2850
10. Gavidia I, Tarrio R, Rodriguez-Trelles F, Perez-Bermudez P, Seitz HU (2007) Plant progesterone 5β-reductase is not homologous to the animal enzyme. Molecular evolutionary characterization of P5βR from Digitalis purpurea. Phytochemistry 68:853-864
11. Hyndman D, Bauman DR, Heredia VV, Penning TM (2003) The aldo-keto superfamily homepage. Chem Biol Int 143-144:621-631
12. InterPro database (2007) ( http://www.ebi.ac.uk/interpro/ DisplayIproEntry?ac=IPR001395 )
13. Jez JM, Penning TM (2001) The aldo-keto reductase (AKR) superfamily: an update. Chem Biol Int 130-132:499-525
14. Jez JM, Bennett MJ, Schlegel BP, Lewis M, Penning TM (1997) Comparative anatomy of the aldo-keto reductase superfamily. Biochem J 326:625-636
15. Jin Y, Penning TM (2007) Aldo-keto reductases and Bioactivation/ detoxication. Ann Rev Phamacol Toxicol 47:263-292
16. Kahn MA, Siddiqui S (1972) Isolation and Structure of Raucaffrinoline, A New Alkaloid from Rauwolfia caffra Sonder. Experientia 28:127-128
17. Kaspera R, Croteau R (2006) Cytochrome P450 oxygenases of taxol biosynthesis. Phytochem Rev 5:433-444
18. Kim S-J, Kim M-R, Bedgar DL, Moinuddin SGA, Cardenas CL, Davin LB, Kang CH, Lewis NG (2004) Functional reclassification of the putative cinnamyl alcohol dehydrogenase multigene family in Arabidopsis. PNAS 101:1455-1460
19. Kutchan TM (1998) Molecular genetics of plant alkaloid biosynthesis. In: Cordell GA (ed) The alkaloids, vol 50. Academic Press, San Diego, pp 257-316
20. Morita T, Huruta T, Ashiuchi M, Yagi T (2002) Characterization of recombinant YakC of Schizosaccharomyces pombe showing YakC defines a new family of aldo-keto reductases. J Biochem 132:635-641
21. Ornstein I (1964) Disc electrophoresis I-background and theory. Ann NY Acad Sci 121:321-349
22. Rosenthal C, Mueller U, Panjikar S, Sun L, Ruppert M, Zhao Y, Stöckigt J (2006) Expression, purification, crystallization and preliminary X-ray analysis of perakine reductase, a new member of the AKR enzyme superfamily from higher plants. Acta Cryst F62:1286-1289
23. Ruppert M, Ma X, Stöckigt J (2005a) Alkaloid biosynthesis in Rauvolfia-cDNA cloning of major enzymes of the ajmaline pathway. Curr Org Chem 9:1431-1444
24. Ruppert M, Woll J, Giritch A, Genady E, Ma X, Stöckigt J (2005b) Functional expression of an ajmaline pathway-specific esterase from Rauvolfia in a novel plant-virus expression system. Planta 222:888-898
25. Sabino JR, Kato L, Braga RM, Vencato I (2006) Raucaffrinoline. Acta Cryst E62:o3181-o3183
26. Sheludko Y, Gerasimenko I, Kolshorn H, Stöckigt J (2002) New alkaloids of the sarpagine group from Rauvolfia serpentina hairy root cultures. J Nat Prod 65:1006-1010
27. Stöckigt J (1995) Biosynthesis in Rauvolfia serpentina, modern aspects of an old medicinal plant. In: Cordell GA (ed) The alkaloids, vol 47. Academic Press, San Diego, pp 115-172
28. Subhadhirasakul S, Takayama H, Aimi N, Ponglux D, Sakai SI (1994) Novel indole alkaloids from the leaves of Rauwolfia sumatrana JACK in Thailand. Chem Pharm Bull 42:1427-1431
29. Unterlinner B, Lenz R, Kutchan TM (1999) Molecular cloning and functional expression of codeinone reductase: the penultimate enzyme in morphine biosynthesis in the opium poppy Papaver somniferum. Plant J 18:465-475
30. Warzecha H, Obitz P, Stöckigt J (1999) Purification, partial amino acid sequence and structure of the product of raucaffrine-O-ß-d- glucosidase from plant cell cultures of Rauwolfia serpentina. Phytochemistry 50:1099-1109
31. Zenk MH (1995) Chasing the enzymes of alkaloid biosynthesis. In: Golding BT, Griffin RJ, Maskill H (eds) Organic reactivity: physical and biological aspects. The Royal Society of Chemistry, Newcastle upon Thyne, pp 89-109
32. Zhang K, Qian Q, Huang Z, Wang Y, Li M, Hong L, Zeng D, Gu M, Chu C, Cheng Z (2006) Gold hull and internode2 encodes a primarily multifunctional cinnamyl-alcohol dehydrogenase in rice. Plant Physiol 140:972-983