Regulation of sesquiterpenoid metabolism in recombinant and elicited Valeriana officinalis hairy roots

Phytochemistry

Volumn 125, Issue , 2016, Pages 43-53

  Ricigliano, Vincent ^a   Kumar, Santosh ^b   Kinison, Scott ^b   Brooks, Christopher ^a   Nybo, S Eric ^b   Chappell, Joe ^b   Howarth, Dianella G ^a  

^a ST JOHN'S UNIVERSITY   (United States)

^b UNIVERSITY OF KENTUCKY   (United States)

Author keywords

Agrobacterium; Caprofoliaceae; Secondary metabolism regulation; Sesquiterpenoid; Valerian root; Valeriana officinalis

Indexed keywords

ACETIC ACID DERIVATIVE; ANXIOLYTIC AGENT; CARYOPHYLLENE; COMPLEMENTARY DNA; CYCLOPENTANE DERIVATIVE; FARNESYL DIPHOSPHATE; GERMACRENE C SYNTHASE; INDENE DERIVATIVE; ISOPRENOID PHOSPHATE; JASMONIC ACID METHYL ESTER; OXYLIPIN; SESQUITERPENE; TRANSFERASE; VALERENAL; VALERENIC ACID; VALERIAN;

CHEMICAL STRUCTURE; CHEMISTRY; GENETICS; HUMAN; ISOLATION AND PURIFICATION; PLANT ROOT;

ACETATES; ALKYL AND ARYL TRANSFERASES; ANTI-ANXIETY AGENTS; CYCLOPENTANES; DNA, COMPLEMENTARY; HUMANS; INDENES; MOLECULAR STRUCTURE; OXYLIPINS; PLANT ROOTS; POLYISOPRENYL PHOSPHATES; SESQUITERPENES; VALERIAN;

EID: 84961898803     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2016.02.011     Document Type: Article

References (56)

1. K. Akiyama, K.-I. Matsuzaki, and H. Hayashi Plant sesquiterpenes induce hyphal branching in arbuscular mycorrhizal fungi Nature 435 2005 824 827 10.1038/nature03608
2. S. Al-Babili, and H.J. Bouwmeester Strigolactones, a novel carotenoid-derived plant hormone Ann. Rev. Plant Biol. 2015 10.1146/annurev-arplant-043014-114759
3. W. Banyai, C. Kirdmanee, M. Mii, and K. Supaibulwatana Overexpression of farnesyl pyrophosphate synthase (FPS) gene affected artemisinin content and growth of Artemisia annua L Plant Cell Tiss. Organ Cult. 103 2010 255 265 10.1007/s11240-010-9775-8
4. J. Bohlmann Terpenoid synthases-from chemical ecology and forest fires to biofuels and bioproducts Struct. Fold. Design 19 2011 1730 1731 10.1016/j.str.2011.11.009
5. R. Bos, H.J. Woerdenbag, and N. Pras Determination of valepotriates J. Chromatogr. A 967 2002 131 146 10.1016/S0021-9673(02)00036-5
6. C. Chambon, V. Ladeveze, A. Oulmouden, M. Servouse, and F. Karst Isolation and properties of yeast mutants affected in farnesyl diphosphate synthetase Curr. Genet. 18 1990 41 46
7. S. Chandra, and R. Chandra Engineering secondary metabolite production in hairy roots Phytochem. Rev. 10 2011 371 395 10.1007/s11101-011-9210-8
8. Chappell, J., Coates, R.M., 2010. In Comprehensive Natural Products II: Chemistry and Biology; Mander, L.; Liu, H.-W., Eds.
9. J. Degenhardt, T.G. Köllner, and J. Gershenzon Monoterpene and sesquiterpene synthases and the origin of terpene skeletal diversity in plants Phytochemistry 70 2009 1621 1637 10.1016/j.phytochem.2009.07.030
10. M.I. Georgiev, A.I. Pavlov, and T. Bley Hairy root type plant in vitro systems as sources of bioactive substances Appl. Microbiol. Biotechnol. 74 2007 1175 1185 10.1007/s00253-007-0856-5
11. G. Giuliano, R. Tavazza, G. Diretto, P. Beyer, and M.A. Taylor Metabolic engineering of carotenoid biosynthesis in plants Trends Biotechnol. 26 2008 139 145 10.1016/j.tibtech.2007.12.003
12. F. Gränicher, P. Christen, and I. Kapetanidis High-yield production of valepotriates by hairy root cultures of Valeriana officinalis L. var. sambucifolia Mikan Plant Cell Rep. 11 1992 339 342 10.1007/BF00233361
13. S. Guillon, J. Trémouillaux-Guiller, P.K. Pati, M. Rideau, and P. Gantet Hairy root research: recent scenario and exciting prospects Curr. Opin. Plant Biol. 9 2006 341 346 10.1016/j.pbi.2006.03.008
14. M.M. Heinrich, M.M. Robles, J.E.J. West, B.R.B.O. de Montellano, and E.E. Rodriguez Ethnopharmacology of Mexican Asteraceae (Compositae) Annu. Rev. Pharmacol. Toxicol. 38 1998 539 565 10.1146/annurev.pharmtox.38.1.539
15. P.J. Houghton The scientific basis for the reputed activity of Valerian J. Pharm. Pharmacol. 51 1999 505 512 10.1211/0022357991772772
16. G.A. Howe, and G. Jander Plant immunity to insect herbivores Plant Biol. 59 2008 41 66 10.1146/annurev.arplant.59.032607.092825
17. N.J.N. Jacobo-Herrera, N.N. Vartiainen, P.P. Bremner, S.S. Gibbons, J.J. Koistinaho, and M.M. Heinrich NF-kappaB modulators from Valeriana officinalis Phytother. Res. 20 2006 917 919 10.1002/ptr.1972
18. R.A.R. Jefferson, T.A.T. Kavanagh, and M.W.M. Bevan GUS fusions: beta-glucuronidase as a sensitive and versatile gene fusion marker in higher plants EMBO J. 6 1987 3901 3907
19. S. Khom, I. Baburin, E. Timin, A. Hohaus, G. Trauner, B. Kopp, and S. Hering Valerenic acid potentiates and inhibits GABAA receptors: molecular mechanism and subunit specificity Neuropharmacology 53 2007 178 187 10.1016/j.neuropharm.2007.04.018
20. S. Khom, B. Strommer, J. Ramharter, T. Schwarz, C. Schwarzer, T. Erker, G.F. Ecker, J. Mulzer, and S. Hering Valerenic acid derivatives as novel subunit-selective GABAA receptor ligands - in vitro and in vivo characterization Br. J. Pharmacol. 161 2010 65 78 10.1111/j.1476-5381.2010.00865.x
21. A. Kirakosyan, P.B. Kaufman, and I. Levin Recent Advances in Plant Biotechnology 2009 Springer US Boston, MA 10.1007/978-1-4419-0194-1-12
22. W. Li, C.-H. Cai, W.-H. Dong, Z.-K. Guo, H. Wang, W.-L. Mei, and H.-F. Dai 2-(2-Phenylethyl)chromone derivatives from Chinese agarwood induced by artificial holing Fitoterapia 98 2014 117 123 10.1016/j.fitote.2014.07.011
23. K.J. Livak, and T.D. Schmittgen Analysis of relative gene expression data using real-time quantitative PCR and the 2-ΔΔCT method Methods 25 2001 402 408 10.1006/meth.2001.1262
24. Y.B. Mao, S. Lu, L.J. Wang, and X.Y. Chen Plant terpenoids: biosynthesis and ecological functions J. Integr. Plant Biol. 2007 10.1111/j.1672-9072.2006.00395.x
25. Y. Matsushita, W. Kang, and B.V. Charlwood Cloning and analysis of a cDNA encoding farnesyl diphosphate synthase from Artemisia annua Gene 172 1996 207 209 10.1016/0378-1119(96)00054-6
26. W.C. McClatchey, G.B. Mahady, B.C. Bennett, L. Shiels, and V. Savo Ethnobotany as a pharmacological research tool and recent developments in CNS-active natural products from ethnobotanical sources Pharmacol. Ther. 123 2009 239 254 10.1016/j.pharmthera.2009.04.002
27. I.I. Merfort Perspectives on sesquiterpene lactones in inflammation and cancer Curr. Drug Targets 12 2011 1560 1573
28. N. Misawa Pathway engineering for functional isoprenoids Curr. Opin. Biotechnol. 22 2011 627 633 10.1016/j.copbio.2011.01.002
29. H. Möhler GABA(A) receptor diversity and pharmacology Cell Tissue Res. 326 2006 505 516 10.1007/s00441-006-0284-3
30. T. Murashige, and F. Skoog A revised medium for rapid growth and bioassays with tobacco tissue cultures Physiol. Plant. 15 1962 473 497 10.1111/j.1399-3054.1962.tb08052.x
31. K. Murphy, Z.J. Kubin, J.N. Shepherd, and R.H. Ettinger Valeriana officinalis root extracts have potent anxiolytic effects in laboratory rats Eur. J. Integr. Med. 17 2010 674 678 10.1016/j.phymed.2009.10.020
32. M. Nell, C. Wawrosch, S. Steinkellner, H. Vierheilig, B. Kopp, A. Lössl, C. Franz, J. Novak, and K. Zitterl-Eglseer Root colonization by symbiotic arbuscular mycorrhizal fungi increases sesquiterpenic acid concentrations in Valeriana officinalis L Planta Med. 76 2009 393 398 10.1055/s-0029-1186180
33. D.R. Nelson The cytochrome p450 homepage Hum. Genomics 4 2009 59 65 10.1146/annurev-arplant-043014-114759
34. K. Nemoto, M. Hara, S. Goto, K. Kasai, H. Seki, M. Suzuki, A. Oka, T. Muranaka, and Y. Mano The aux1 gene of the Ri plasmid is sufficient to confer auxin autotrophy in tobacco BY-2 cells J. Plant Physiol. 166 2009 729 738 10.1016/j.jplph.2008.09.006
35. J.D. Newman, and J. Chappell Isoprenoid biosynthesis in plants: carbon partitioning within the cytoplasmic pathway Crit. Rev. Biochem. Mol. Biol. 34 1999 95 106 10.1080/10409239991209228
36. O. Nilsson, and O. Olsson Getting to the root: the role of the Agrobacterium rhizogenes rol genes in the formation of hairy roots Physiol. Plant. 100 1997 463 473 10.1111/j.1399-3054.1997.tb03050.x
37. J. Patočka, and J. Jakl Biomedically relevant chemical constituents of Valeriana officinalis. 2010 10.2478/v10136-009-0002-z
38. B.W. Pyle, H.T. Tran, B. Pickel, T.M. Haslam, Z. Gao, G. MacNevin, J.C. Vederas, S.-U. Kim, and D.-K. Ro Enzymatic synthesis of valerena-4,7(11)-diene by a unique sesquiterpene synthase from the valerian plant (Valeriana officinalis) FEBS J. 279 2012 3136 3146 10.1111/j.1742-4658.2012.08692.x
39. Ain Raal Variation in the composition of the essential oil of commercial Valeriana officinalis L. roots from different countries J. Essential Oil Res. 20 6 2008 524 529
40. D.-K. Ro, E.M. Paradise, M. Ouellet, K.J. Fisher, K.L. Newman, J.M. Ndungu, K.A. Ho, R.A. Eachus, T.S. Ham, J. Kirby, M.C.Y. Chang, S.T. Withers, Y. Shiba, R. Sarpong, and J.D. Keasling Production of the antimalarial drug precursor artemisinic acid in engineered yeast Nature 440 2006 940 943 10.1038/nature04640
41. S.C. Roberts Production and engineering of terpenoids in plant cell culture Nat. Chem. Biol. 3 2007 387 395 10.1038/nchembio.2007.8
42. T. Røstelien, A.K. Borg-Karlson, J. Fäldt, U. Jacobsson, and H. Mustaparta The plant sesquiterpene germacrene D specifically activates a major type of antennal receptor neuron of the tobacco budworm moth Heliothis virescens Chem. Senses 25 2000 141 148
43. F. Sherman Getting started with yeast Method Enzymol. 350 2002 3 41
44. S. Srivastava, and A.K. Srivastava Hairy root culture for mass-production of high-value secondary metabolites Crit. Rev. Biotechnol. 27 2007 29 43 10.1080/07388550601173918
45. S. Takahashi, Y.S. Yeo, Y. Zhao, P.E. O'Maille, B.T. Greenhagen, J.P. Noel, R.M. Coates, and J. Chappell Functional characterization of premnaspirodiene oxygenase, a cytochrome P450 catalyzing regio- and stereo-specific hydroxylations of diverse sesquiterpene substrates J. Biol. Chem. 282 2007 31744 31754 10.1074/jbc.M703378200
46. M. Torkamani, N. Abbaspour, M. Jafari, and A. Samadi Elicitation of valerenic acid in the hairy root cultures of Valeriana officinalis L (Valerianaceae) Trop. J. Pharm. Res. 13 2014 943 947 10.4314/tjpr.v13i6.17
47. M. Torkamani, M. Jafari, N. Abbaspour, and R. Heidary Enhanced production of valerenic acid in hairy root culture of Valeriana officinalis by elicitation Central Eur. J. Biol. 2014 10.2478/s11535-014-0320-3
48. B.A. Triplett, S.C. Moss, J.M. Bland, M.K. Dowd, and G.C. Phillips Induction of hairy root cultures from Gossypium hirsutum and Gossypium barbadense to produce gossypol and related compounds In Vitro Cell Dev. Biol. Plant 44 2008 508 517 10.1007/s11627-008-9141-2
49. J. Wang, J. Zhao, H. Liu, L. Zhou, Z. Liu, J. Wang, J. Han, Z. Yu, and F. Yang Chemical analysis and biological activity of the essential oils of two Valerianaceous Species from China: Nardostachys chinensis and Valeriana officinalis Molecules 15 2010 6411 6422 10.3390/molecules15096411
50. P.-C. Wang, J.-M. Hu, X.-H. Ran, Z.-Q. Chen, H.-Z. Jiang, Y.-Q. Liu, J. Zhou, and Y.-X. Zhao Iridoids and sesquiterpenoids from the roots of Valeriana officinalis J. Nat. Prod. 72 2009 1682 1685 10.1021/np9003382
51. C. Weitzel, and H.T. Simonsen Cytochrome P450-enzymes involved in the biosynthesis of mono- and sesquiterpenes Phytochem. Rev. 2013 10.1007/s11101-013-9280-x
52. U. Werneke, T. Turner, and S. Priebe Complementary medicines in psychiatry: review of effectiveness and safety Br. J. Psychiatry 188 2006 109 121 10.1192/bjp.188.2.109
53. D. Wheatley Medicinal plants for insomnia: a review of their pharmacology, efficacy and tolerability J. Psychopharmacol. (Oxford) 19 2005 414 421 10.1177/0269881105053309
54. C.-Q. Yang, X. Fang, X.-M. Wu, Y.-B. Mao, L.-J. Wang, and X.-Y. Chen Transcriptional regulation of plant secondary metabolism J. Integr. Plant Biol. 54 2012 703 712 10.1111/j.1744-7909.2012.01161.x
55. Y.-S. Yeo, S.E. Nybo, A.G. Chittiboyina, A.D. Weerasooriya, Y.-H. Wang, E. Gongora-Castillo, B. Vaillancourt, C.R. Buell, D. Dellapenna, M.D. Celiz, A.D. Jones, E.S. Wurtele, N. Ransom, N. Dudareva, K.A. Shaaban, N. Tibrewal, S. Chandra, T. Smillie, I.A. Khan, R.M. Coates, D.S. Watt, and J. Chappell Functional identification of valerena-1,10-diene synthase, a terpene synthase catalyzing a unique chemical cascade in the biosynthesis of biologically active sesquiterpenes in Valeriana officinalis J. Biol. Chem. 2012 10.1074/jbc.M112.415836
56. S. Zhang, Y.-K. Won, C.-N. Ong, and H.-M. Shen Anti-cancer potential of sesquiterpene lactones: bioactivity and molecular mechanisms Curr. Med. Chem. Anticancer Agents 5 2005 239 249 10.1016/j.febslet.2006.01.065