cDNA Cloning and expression analysis of farnesyl pyrophosphate synthase from Ornithogalum saundersiae

Zeitschrift fur Naturforschung - Section C Journal of Biosciences

Volumn 69 C, Issue 5-6, 2014, Pages 259-270

  Guo, Lei ^a   Kong, Jian Qiang ^a  

^a BEIJING HOSPITAL   (China)

Author keywords

Farnesyl pyrophosphate synthase; Ornithogalum saundersiae; OSW 1; Sterols

Indexed keywords

COMPLEMENTARY DNA; GERANYLTRANSFERASE; PLANT DNA; PRIMER DNA; RECOMBINANT PROTEIN;

AMINO ACID SEQUENCE; ARTICLE; CHEMISTRY; CLASSIFICATION; ENZYMOLOGY; ESCHERICHIA COLI; GENETICS; MASS FRAGMENTOGRAPHY; MOLECULAR CLONING; MOLECULAR GENETICS; NUCLEOTIDE SEQUENCE; ORNITHOGALUM; PHYLOGENY; POLYACRYLAMIDE GEL ELECTROPHORESIS; POLYMERASE CHAIN REACTION; SEQUENCE HOMOLOGY;

AMINO ACID SEQUENCE; BASE SEQUENCE; CLONING, MOLECULAR; DNA PRIMERS; DNA, COMPLEMENTARY; DNA, PLANT; ELECTROPHORESIS, POLYACRYLAMIDE GEL; ESCHERICHIA COLI; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; GERANYLTRANSTRANSFERASE; MOLECULAR SEQUENCE DATA; ORNITHOGALUM; PHYLOGENY; POLYMERASE CHAIN REACTION; RECOMBINANT PROTEINS; SEQUENCE HOMOLOGY, AMINO ACID;

EID: 84903168917     PISSN: 09395075     EISSN: None     Source Type: Journal    
DOI: 10.5560/ZNC.2013-0130     Document Type: Article

References (50)

1. Cao X., Yin T., Miao Q., Li C., Ju X., Sun Y., and Jiang J. (2012), Molecular characterization and expression analysis of a gene encoding for farnesyl diphosphate syn-thase from Euphorbia pekinensis Rupr. Mol. Biol. Rep. 39, 1487-1492.
2. Cervantes-Cervantes M., Gallagher C. E., Zhu C., and Wurtzel E. T. (2006), Maize cDNAs expressed in endosperm encode functional farnesyl diphosphate synthase with geranylgeranyl diphosphate synthase activity. Plant Physiol. 141, 220-231.
3. Chen D., Ye H., and Li G. (2000), Expression of a chimeric farnesyl diphosphate synthase gene in Artemisia an-nua L. transgenic plants via Agrobacterium tumefaciens-mediated transformation. Plant Sci. 155, 179-185.
4. Deng S., Yu B., Lou Y., and Hui Y. (1999), First total synthesis of an exceptionally potent antitumor saponin, OSW-1. J. Org. Chem. 64, 202-208.
5. Dhar M. K., Koul A., and Kaul S. (2013), Farnesyl pyrophos-phate synthase: a key enzyme in isoprenoid biosynthetic pathway and potential molecular target for drug development. Nat. Biotechnol. 30, 114-123.
6. Evans D. H., Yao X. D., and Willer D. O. (2007), EP Patent EP1741787.
7. Evans D. H., Willer D. O., and Yao X. D. (2009), US Patent 7,575,860.
8. Finn R. D., Bateman A., Clements J., Coggill P., Eber-hardt R. Y., Eddy S. R., Heger A., Hetherington K., Holm L., Mistry J., Sonnhammer E. L., Tate J., and Punta M. (2014), Pfam: the protein families database. Nucleic Acids Res. 42, D222-D230.
9. Fischer M. J., Meyer S., Claudel P., Bergdoll M., and Karst F. (2011), Identification of a lysine residue important for the catalytic activity of yeast farnesyl diphosphate synthase. Protein J. 30, 334-339.
10. Garcia-Prieto C., Riaz Ahmed K. B., Chen Z., Zhou Y., Hammoudi N., Kang Y., Lou C., Mei Y., Jin Z., and Huang P. (2013), Effective killing of leukemia cells by the natural product OSW-1 through disruption of cellular calcium homeostasis. J. Biol. Chem. 288, 3240-3250.
11. Ginzberg I., Thippeswamy M., Fogelman E., Demirel U., Mweetwa A. M., Tokuhisa J., and Veilleux R. E. (2012), Induction of potato steroidal glycoalkaloid biosynthetic pathway by overexpression of cDNA encoding primary metabolism HMG-CoA reductase and squalene synthase. Planta 235, 1341-1353.
12. Gu W., Wu Q. N., Chao J. G., Xi B. L., Li L., and Shen X. Y. (2011), Molecular cloning of farnesyl pyrophosphate syn-thase from Alisma orientale (Sam.) Juzep. and its distribution pattern and bioinformatics analysis. Yao Xue Xue Bao 46, 605-612.
13. Guan Y., Zheng D., Zhou L., Wang H., Yan Z., Wang N., Chang H., She P., and Lei P. (2011), Synthesis of 5(6)-dihydro-OSW-1 analogs bearing three kinds of disaccha-rides linking at 15-hydroxy and their antitumor activities. Bioorg. Med. Chem. Lett. 21, 2921-2924.
14. Homann V., Mende K., Arntz C., Ilardi V., Macino G., Morelli G., Bose G., and Tudzynski B. (1996), The iso-prenoid pathway: cloning and characterization of fungal FPPS genes. Curr. Genet. 30, 232-239.
15. Jin J. C., Jin X. L., Zhang X., Piao Y. S., and Liu S. P. (2013), Effect of OSW-1 on microRNA expression profiles of hepatoma cells and functions of novel microRNAs. Mol. Med. Rep. 7, 1831-1837.
16. Johnson M., Zaretskaya I., Raytselis Y., Merezhuk Y., McGinnis S., and Madden T. L. (2008), NCBI BLAST: a better web interface. Nucleic Acids Res. 36, W5-W9.
17. Jordao F. M., Gabriel H. B., Alves J. M., Angeli C. B., Bi-fano T. D., Breda A., de Azevedo M. F., Basso L. A., Wunderlich G., Kimura E. A., and Katzin A. M. (2013), Cloning and characterization of bifunctional enzyme far-nesyl diphosphate/geranylgeranyl diphosphate synthase from Plasmodium falciparum. Malaria J. 12, 184.
18. Keim V., Manzano D., Fernandez F. J., Closa M., Andrade P., Caudepon D., Bortolotti C., Vega M. C., Arro M., and Ferrer A. (2012), Characterization of Arabidopsis FPS isozymes and FPS gene expression analysis provide insight into the biosynthesis of isoprenoid precursors in seeds. PLoS One 7, e49109.
19. Kim O. T., Kim S. H., Ohyama K., Muranaka T., Choi Y. E., Lee H. Y., Kim M. Y., and Hwang B. (2010), Upregula-tion of phytosterol and triterpene biosynthesis in Cen-tella asiatica hairy roots overexpressed ginseng farne-syl diphosphate synthase. Plant Cell Rep. 29, 403-411.
20. Kong J. Q., Wang W., Wang L. N., Zheng X. D., Cheng K. D., and Zhu P. (2009), The improvement of amorpha-4,11-diene production by a yeast-conform variant. J. Appl. Microbiol. 106, 941-951.
21. Kong J. Q., Lu D., and Wang Z. B. (2014), Molecular cloning and yeast expression of cinnamate 4-hydroxylase from Ornithogalum saundersiae Baker. Molecules 19, 1608-1621.
22. Koyama T., Obata S., Osabe M., Takeshita A., Yokoyama K., Uchida M., Nishino T., and Ogura K. (1993), Thermostable farnesyl diphosphate synthase of Bacillus stearothermophilus: molecular cloning, sequence determination, overproduction, and purification. J. Biochem. 113, 355-363.
23. Koyama T., Tajima M., Sano H., Doi T., Koike-Takeshita A., Obata S., Nishino T., and Ogura K. (1996), Identification of significant residues in the substrate binding site of Bacillus stearothermophilus farnesyl diphosphate syn-thase. Biochemistry 35, 9533-9538.
24. Kubo S., Mimaki Y., Terao M., Sashida Y., Nikaido T., and Ohmoto T. (1992), Acylated cholestane glycosides from the bulbs of Ornithogalum saundersiae. Phytochemistry 31, 3969-3973.
25. Lan J. B., Yu R. C., Yu Y. Y., and Fan Y. P. (2013), Molecular cloning and expression of Hedychium coronar-ium farnesyl pyrophosphate synthase gene and its possible involvement in the biosynthesis of floral and wounding/herbivory induced leaf volatile sesquiter-penoids. Gene 518, 360-367.
26. Lee P. C., Petri R., Mijts B. N., Watts K. T., and Schmidt-Dannert C. (2005), Directed evolution of Escherichia coli farnesyl diphosphate synthase (IspA) reveals novel structural determinants of chain length specificity. Metab. Eng. 7, 18-26.
27. Maj J., Morzycki J. W., Rarova L., Oklest'Kova J., Strnad M., and Wojtkielewicz A. (2011), Synthesis and biological activity of 22-deoxo-23-oxa analogues of saponin OSW-1. J. Med. Chem. 54, 3298-3305.
28. McGinnis S., and Madden T. L. (2004), BLAST: at the core of a powerful and diverse set of sequence analysis tools. Nucleic Acids Res. 32, W20-25.
29. Mimaki Y., Kuroda M., Kameyama A., Sashida Y., Hirano T., Oka K., Maekawa R., Wada T., Sugita K., and Beut-ler J. A. (1997), Cholestane glycosides with potent cyto-static activities on various tumor cells from Ornithogalum saundersiae bulbs. Bioorg. Med. Chem. Lett. 7, 633-636.
30. Moller S., Croning M. D., and Apweiler R. (2001), Evaluation of methods for the prediction of membrane spanning regions. Bioinformatics 17, 646- 653.
31. Nuttall J. M., Hettema E. H., and Watts D. J. (2012), Farnesyl diphosphate synthase, the target for nitrogen-containing bisphosphonate drugs, is a peroxisomal enzyme in the model system Dictyostelium discoideum. Biochem. J. 447, 353-361.
32. Paddon C. J., Westfall P. J., Pitera D. J., Benjamin K., Fisher K., McPhee D., Leavell M. D., Tai A., Main A., Eng D., Polichuk D. R., Teoh K. H., Reed D. W., Treynor T., Lenihan J., Fleck M., Bajad S., Dang G., Dengrove D., Diola D., Dorin G., Ellens K. W., Fickes S., Galazzo J., Gaucher S. P., Geistlinger T., Henry R., Hepp M., Horning T., Iqbal T., Jiang H., Kizer L., Lieu B., Melis D., Moss N., Regentin R., Secrest S., Tsuruta H., Vazquez R., Westblade L. F., Xu L., Yu M., Zhang Y., Zhao L., Lievense J., Covello P. S., Keasling J. D., Reiling K. K., Renninger N. S., and Newman J. D. (2013), High-level semi-synthetic production of the potent antimalarial artemisinin. Nature 496, 528-532.
33. Petersen T. N., Brunak S., von Heijne G., and Nielsen H. (2011), SignalP 4.0: discriminating signal peptides from transmembrane regions. Nat. Methods 8, 785-786.
34. Punta M., Coggill P. C., Eberhardt R. Y., Mistry J., Tate J., Boursnell C., Pang N., Forslund K., Ceric G., Clements J., Heger A., Holm L., Sonnhammer E. L., Eddy S. R., Bate-man A., and Finn R. D. (2012), The Pfam protein families database. Nucleic Acids Res. 40, D290-D301.
35. Reilly J. F., Martinez S. D., Mickey G., and Maher P. A. (2002), A novel role for farnesyl pyrophosphate synthase in fibroblast growth factor-mediated signal transduction. Biochem. J. 366, 501-510.
36. Ro D. K., Paradise E. M., Ouellet M., Fisher K. J., Newman K. L., Ndungu J. M., Ho K. A., Eachus R. A., Ham T. S., Kirby J., Chang M. C., Withers S. T., Shiba Y., Sar-pong R., and Keasling J. D. (2006), Production of the an-timalarial drug precursor artemisinic acid in engineered yeast. Nature 440, 940-943.
37. Sanmiya K., Iwasaki T., Matsuoka M., Miyao M., and Ya-mamoto N. (1997), Cloning of a cDNA that encodes far-nesyl diphosphate synthase and the blue-light-induced expression of the corresponding gene in the leaves of rice plants. Biochim. Biophys. Acta 1350, 240-246.
38. Sato Y., Takaya A., and Yamamoto T. (2011), Meta-analytic approach to the accurate prediction of secreted virulence effectors in Gram-negative bacteria. BMC Bioinf. 12, 442.
39. Sun Y., Zhao Y., Wang L., Lou H. X., and Cheng A. X. (2012), Cloning and expression analysis of squalene syn-thase, a key enzyme involved in antifungal steroidal gly-coalkaloids biosynthesis from Solanum nigrum. Drug Discov. Ther. 6, 242-248.
40. Szkopinska A. and Plochocka D. (2005), Farnesyl diphos-phate synthase; regulation of product specificity. Acta Biochim. Pol. 52, 45-55.
41. Thabet I., Guirimand G., Courdavault V., Papon N., Godet S., Dutilleul C., Bouzid S., Giglioli-Guivarc'H N., Clastre M., and Simkin A. J. (2011), The subcellular localization of periwinkle farnesyl diphosphate synthase provides insight into the role of peroxisome in isoprenoid biosynthesis. J. Plant Physiol. 168, 2110-2116.
42. Veliky I. A. and Martin S. M. (1970), A fermenter for plant cell suspension cultures. Can. J. Microbiol. 16, 223-226.
43. Wheeler D. L., Church D. M., Federhen S., Lash A. E., Madden T. L., Pontius J. U., Schuler G. D., Schriml L. M., Se-queira E., Tatusova T. A., and Wagner L. (2003), Database resources of the National Center for Biotechnology. Nucleic Acids Res. 31, 28-33.
44. Xiang L., Zhao K., and Chen L. (2010), Molecular cloning and expression of Chimonanthus praecox farnesyl py-rophosphate synthase gene and its possible involvement in the biosynthesis of floral volatile sesquiterpenoids. Plant Physiol. Biochem. 48, 845-850.
45. Xue J., Liu P., Pan Y., and Guo Z. (2008), A total synthesis of OSW-1. J. Org. Chem. 73, 157-161.
46. Ye J., McGinnis S., and Madden T. L. (2006), BLAST: improvements for better sequence analysis. Nucleic Acids Res. 34, W6-W9.
47. Ying W., Wu Y. L., Feng X. C., Lian L. H., Jiang Y. Z., and Nan J. X. (2010), The protective effects of total saponins from Ornithogalum saundersiae (Liliaceae) on acute hepatic failure induced by lipopolysaccharide and D-galactosamine in mice. J. Ethnopharmacol. 132, 450-455.
48. Yu W. and Jin Z. (2002), Total synthesis of the anticancer natural product OSW-1. J. Am. Chem. Soc. 124, 6576-6583.
49. Zheng D., Guan Y., Chen X., Xu Y., Chen X., and Lei P. (2011), Synthesis of cholestane saponins as mimics of OSW-1 and their cytotoxic activities. Bioorg. Med. Chem. Lett. 21, 3257-3260.
50. Zhou Y., Garcia-Prieto C., Carney D. A., Xu R. H., Peli-cano H., Kang Y., Yu W., Lou C., Kondo S., Liu J., Harris D. M., Estrov Z., Keating M. J., Jin Z., and Huang P. (2005), OSW-1: a natural compound with potent anti-cancer activity and a novel mechanism of action. J. Natl. Cancer Inst. 97, 1781-1785.