Enzymatic synthesis of valerena-4,7(11)-diene by a unique sesquiterpene synthase from the valerian plant (Valeriana officinalis)

FEBS Journal

Volumn 279, Issue 17, 2012, Pages 3136-3146

  Pyle, Bryan W ^a   Tran, Hue T ^a   Pickel, Benjamin ^a   Haslam, Tegan M ^a   Gao, Zhizeng ^b   MacNevin, Gillian ^a   Vederas, John C ^b   Kim, Soo Un ^c   Ro, Dae Kyun ^a  

^a UNIVERSITY OF CALGARY   (Canada)

^b UNIVERSITY OF ALBERTA   (Canada)

^c Seoul National University   (South Korea)

Author keywords

sesquiterpene synthase; terpenoid; valerena 4,7(11) diene; valerenic acid; Valeriana officinalis

Indexed keywords

GERMACRENE C; GERMACRENE D; PROTEIN VOTPS1; PROTEIN VOTPS2; SYNTHETASE; TERPENE DERIVATIVE; UNCLASSIFIED DRUG; VALERENA 4,7(11)DIENE;

ARTICLE; BIOSYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME KINETICS; GENE EXPRESSION; GENETIC TRANSCRIPTION; IN VITRO STUDY; MASS FRAGMENTOGRAPHY; NONHUMAN; NUCLEOTIDE SEQUENCE; PLANT ROOT; PRIORITY JOURNAL; VALERIANA OFFICINALIS;

BASE SEQUENCE; CYCLIZATION; DNA PRIMERS; DNA, COMPLEMENTARY; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR SEQUENCE DATA; POLYMERASE CHAIN REACTION; SESQUITERPENES; VALERIAN;

VALERIANA; VALERIANA OFFICINALIS;

EID: 84865241938     PISSN: 1742464X     EISSN: 17424658     Source Type: Journal    
DOI: 10.1111/j.1742-4658.2012.08692.x     Document Type: Article

References (33)

1. Houghton PJ, (1988) The biological activity of Valerian and related plants. J Ethnopharmacol 22, 121-142.
2. Houghton PJ, (1999) The scientific basis for the reputed activity of Valerian. J Pharm Pharmacol 51, 505-512.
3. Barnes PM, Powell-Griner E, McFann K, &, Nahin RL, (2004) Complementary and alternative medicine use among adults: United States, 2002. Adv Data, 1-19.
4. Letchamo W, Ward W, Heard B, &, Heard D, (2004) Essential oil of Valeriana officinalis L. cultivars and their antimicrobial activity as influenced by harvesting time under commercial organic cultivation. J Agric Food Chem 52, 3915-3919.
5. Wang Y, Jin L, Yu S, Shi Q, Gu Y, &, Kiyota H, (2010) Chemical constituents of plants from the genus Valeriana. Mini Rev Org Chem 7, 161-172.
6. Bos R, Woerdenbag HJ, Hendriks H, &, Scheffer JJC, (1997) Composition of the essential oils from underground parts of Valeriana officinalis L. and several closely related taxa. Flavour Fragr J 12, 359-370.
7. Bent S, Padula A, Moore D, Patterson M, &, Mehling W, (2006) Valerian for sleep: a systematic review and meta-analysis. Am J Med 119, 1005-1012.
8. Hendriks H, Bos R, Woerdenbag HJ, &, Koster AS, (1985) Central nervous depressant activity of valerenic acid in the mouse. Planta Med 51, 28-31.
9. (A) receptors: molecular mechanism and subunit specificity. Neuropharmacology 53, 178-187.
10. A receptors as in vivo substrate for the anxiolytic action of valerenic acid, a major constituent of valerian root extracts. Neuropharmacology 56, 174-181.
11. A receptor ligands-in vitro and in vivo characterization. Br J Pharmacol 161, 65-78.
12. Takemoto H, Yagura T, &, Ito M, (2009) Evaluation of volatile components from spikenard: valerena-4,7(11)-diene is a highly active sedative compound. J Nat Med 63, 380-385.
13. (A) receptor diversity and pharmacology. Cell Tissue Res 326, 505-516.
14. A receptor subtypes. Adv Pharmacol 54, 231-263.
15. Chang YJ, Song SH, Park SH, &, Kim SU, (2000) Amorpha-4,11-diene synthase of Artemisia annua: cDNA isolation and bacterial expression of a terpene synthase involved in artemisinin biosynthesis. Arch Biochem Biophys 383, 178-184.
16. Jones CG, Moniodis J, Zulak KG, Scaffidi A, Plummer JA, Ghisalberti EL, Barbour EL, &, Bohlmann J, (2011) Sandalwood fragrance biosynthesis involves sesquiterpene synthases of both the terpene synthase (TPS)-a and TPS-b subfamilies, including santalene synthases. J Biol Chem 286, 17445-17454.
17. Wallaart TE, Bouwmeester HJ, Hille J, Poppinga L, &, Maijers NC, (2001) Amorpha-4,11-diene synthase: cloning and functional expression of a key enzyme in the biosynthetic pathway of the novel antimalarial drug artemisinin. Planta 212, 460-465.
18. Sharon-Asa L, Shalit M, Frydman A, Bar E, Holland D, Or E, Lavi U, Lewinsohn E, &, Eyal Y, (2003) Citrus fruit flavor and aroma biosynthesis: isolation, functional characterization, and developmental regulation of Cstps1, a key gene in the production of the sesquiterpene aroma compound valencene. Plant J 36, 664-674.
19. Farhi M, Marhevka E, Masci T, Marcos E, Eyal Y, Ovadis M, Abeliovich H, &, Vainstein A, (2011) Harnessing yeast subcellular compartments for the production of plant terpenoids. Metab Eng 13, 474-481.
20. Ro DK, Paradise EM, Ouellet M, Fisher KJ, Newman KL, Ndungu JM, Ho KA, Eachus RA, Ham TS, Kirby J, et al. (2006) Production of the antimalarial drug precursor artemisinic acid in engineered yeast. Nature 440, 940-943.
21. Takahashi S, Yeo Y, Greenhagen BT, McMullin T, Song L, Maurina-Brunker J, Rosson R, Noel JP, &, Chappell J, (2007) Metabolic engineering of sesquiterpene metabolism in yeast. Biotechnol Bioeng 97, 170-181.
22. Chevreux B, Pfisterer T, Drescher B, Driesel AJ, Muller WE, Wetter T, &, Suhai S, (2004) Using the miraEST assembler for reliable and automated mRNA transcript assembly and SNP detection in sequenced ESTs. Genome Res 14, 1147-1159.
23. Back K, Yin S, &, Chappell J, (1994) Expression of a plant sesquiterpene cyclase gene in Escherichia coli. Arch Biochem Biophys 315, 527-532.
24. Bouwmeester HJ, Kodde J, Verstappen FW, Altug IG, de Kraker JW, &, Wallaart TE, (2002) Isolation and characterization of two germacrene A synthase cDNA clones from chicory. Plant Physiol 129, 134-144.
25. Göpfert JC, Macnevin G, Ro DK, &, Spring O, (2009) Identification, functional characterization and developmental regulation of sesquiterpene synthases from sunflower capitate glandular trichomes. BMC Plant Biol 9, 86, doi:10.1186/1471-2229-9-86.
26. Ro DK, Ouellet M, Paradise EM, Burd H, Eng D, Paddon CJ, Newman JD, &, Keasling JD, (2008) Induction of multiple pleiotropic drug resistance genes in yeast engineered to produce an increased level of anti-malarial drug precursor, artemisinic acid. BMC Biotechnol 8, 83, doi:10.1186/1472-6750-8-83.
27. Colby SM, Crock J, Dowdle-Rizzo B, Lemaux PG, &, Croteau R, (1998) Germacrene C synthase from Lycopersicon esculentum cv. VFNT cherry tomato: cDNA isolation, characterization, and bacterial expression of the multiple product sesquiterpene cyclase. Proc Natl Acad Sci USA 95, 2216-2221.
28. Kitayama T, Kawabata G, &, Ito M, (2010) Concise synthesis of valerena-4,7(11)-diene, a highly active sedative, from valerenic acid. Biosci Biotechnol Biochem 74, 1963-1964.
29. Paul C, Konig WA, &, Muhle H, (2001) Pacifigorgianes and tamariscene as constituents of Frullania tamarisci and Valeriana officinalis. Phytochemistry 57, 307-313.
30. Kumeta Y, &, Ito M, (2010) Characterization of delta-guaiene synthases from cultured cells of Aquilaria, responsible for the formation of the sesquiterpenes in agarwood. Plant Phsiol 154, 1998-2007.
31. Lee S, &, Chappell J, (2008) Biochemical and genomic characterization of terpene synthases in Magnolia grandiflora. Plant Physiol 147, 1017-1033.
32. Meisel L, Fonseca B, Gonzalez S, Baeza-Yates R, Cambiazo V, Campos R, Gonzalez M, Orellana A, Retamales J, &, Silva H, (2005) A rapid and efficient method for purifying high quality total RNA from peaches (Prunus persica) for functional genomics analyses. Biol Res 38, 83-88.
33. Gietz RD, &, Schiestl RH, (2007) High-efficiency yeast transformation using the LiAc/SS carrier DNA/PEG method. Nat Protoc 2, 31-34.