Suites of Terpene Synthases Explain Differential Terpenoid Production in Ginger and Turmeric Tissues

PLoS ONE

Volumn 7, Issue 12, 2012, Pages

  Koo, Hyun Jo ^a,b   Gang, David R ^a,c  

^a UNIVERSITY OF ARIZONA   (United States)

^b SALK INSTITUTE FOR BIOLOGICAL STUDIES   (United States)

^c WASHINGTON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA PHELLANDRENE; BETA SESQUIPHELLANDRENE; CARYOPHYLLENE; HUMULENE; SESQUITERPENE; TERPENE; TERPENOID; TRITERPENOID; UNCLASSIFIED DRUG; ZINGIBERENE;

AMINO ACID SEQUENCE; ARTICLE; CONTROLLED STUDY; CURCUMA LONGA; ENZYME ANALYSIS; ENZYME STRUCTURE; ENZYME SYNTHESIS; EXPRESSED SEQUENCE TAG; GENE; GENE CLUSTER; GINGER; MTPS GENE; NONHUMAN; PLANT LEAF; PROTEIN EXPRESSION; PROTEIN FUNCTION; STPS GENE; TPS GENE;

ALKYL AND ARYL TRANSFERASES; CELL LINE; CELL LINE, TUMOR; CLONING, MOLECULAR; CODON; CURCUMA; DNA PRIMERS; DNA, COMPLEMENTARY; ESCHERICHIA COLI; EXPRESSED SEQUENCE TAGS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; GINGER; HUMANS; MODELS, CHEMICAL; MOLECULAR CONFORMATION; PHYLOGENY; PLANT EXTRACTS; RHIZOME; TEMPERATURE; TERPENES; YEASTS;

CURCUMA LONGA; ZINGIBER OFFICINALE; ZINGIBER ZERUMBET; ZINGIBERACEAE;

EID: 84871281193     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0051481     Document Type: Article

References (44)

1. Kundu JK, Na HK, Surh YJ, (2009) Ginger-derived phenolic substances with cancer preventive and therapeutic potential. Forum Nutr 61: 182-192.
2. Lopez P, Sanchez C, Batlle R, Nerin C, (2005) Solid- and vapor-phase antimicrobial activities of six essential oils: susceptibility of selected foodborne bacterial and fungal strains. J Agric Food Chem 53: 6939-6946.
3. Ficker CE, Arnason JT, Vindas PS, Alvarez LP, Akpagana K, et al. (2003) Inhibition of human pathogenic fungi by ethnobotanically selected plant extracts. Mycoses 46: 29-37.
4. Habib SH, Makpol S, Abdul Hamid NA, Das S, Ngah WZ, et al. (2008) Ginger extract (Zingiber officinale) has anti-cancer and anti-inflammatory effects on ethionine-induced hepatoma rats. Clinics (Sao Paulo) 63: 807-813.
5. Nigam N, George J, Srivastava S, Roy P, Bhui K, et al. (2009) Induction of apoptosis by [6]-gingerol associated with the modulation of p53 and involvement of mitochondrial signaling pathway in B[a]P-induced mouse skin tumorigenesis. Cancer Chemother Pharmacol 24: 24.
6. Jeong CH, Bode AM, Pugliese A, Cho YY, Kim HG, et al. (2009) [6]-Gingerol suppresses colon cancer growth by targeting leukotriene A4 hydrolase. Cancer Res 69: 5584-5591.
7. Shukla Y, Singh M, (2007) Cancer preventive properties of ginger: a brief review. Food Chem Toxicol 45: 683-690.
8. Wang G, Li X, Huang F, Zhao J, Ding H, et al. (2005) Antitumor effect of beta-elemene in non-small-cell lung cancer cells is mediated via induction of cell cycle arrest and apoptotic cell death. Cell Mol Life Sci 62: 881-893.
9. Jianjun Q, Song Z, Yin L, Jia Z, Donglei L, (2008) Treatment of chylothorax with elemene. Thorac Cardiovasc Surg 56: 103-105.
10. Yamahara J, Mochizuki M, Rong HQ, Matsuda H, Fujimura H, (1988) The anti-ulcer effect in rats of ginger constituents. J Ethnopharmacol 23: 299-304.
11. Yamahara J, Hatakeyama S, Taniguchi K, Kawamura M, Yoshikawa M, (1992) Stomachic principles in ginger. II. Pungent and anti-ulcer effects of low polar constituents isolated from ginger, the dried rhizoma of Zingiber officinale Roscoe cultivated in Taiwan. The absolute stereostructure of a new diarylheptanoid. Yakugaku Zasshi 112: 645-655.
12. Jurenka JS, (2009) Anti-inflammatory properties of curcumin, a major constituent of Curcuma longa: a review of preclinical and clinical research. Altern Med Rev 14: 141-153.
13. Ravindran J, Prasad S, Aggarwal BB, (2009) Curcumin and cancer cells: how many ways can curry kill tumor cells selectively? Aaps J 11: 495-510.
14. Jayaprakasha GK, Jena BS, Negi PS, Sakariah KK, (2002) Evaluation of antioxidant activities and antimutagenicity of turmeric oil: a byproduct from curcumin production. Z Naturforsch [C] 57: 828-835.
15. Negi PS, Jayaprakasha GK, Jagan Mohan Rao L, Sakariah KK, (1999) Antibacterial activity of turmeric oil: a byproduct from curcumin manufacture. J Agric Food Chem 47: 4297-4300.
16. Nishiyama T, Mae T, Kishida H, Tsukagawa M, Mimaki Y, et al. (2005) Curcuminoids and sesquiterpenoids in turmeric (Curcuma longa L.) suppress an increase in blood glucose level in type 2 diabetic KK-Ay mice. J Agric Food Chem 53: 959-963.
17. Lee Y, (2009) Activation of apoptotic protein in U937 cells by a component of turmeric oil. BMB Rep 42: 96-100.
18. Lee HS, (2006) Antiplatelet property of Curcuma longa L. rhizome-derived ar-turmerone. Bioresource Technology 97: 1372-1376.
19. Picaud S, Olsson ME, Brodelius M, Brodelius PE, (2006) Cloning, expression, purification and characterization of recombinant (+)-germacrene D synthase from Zingiber officinale. Arch Biochem Biophys 452: 17-28.
20. Fujisawa M, Harada H, Kenmoku H, Mizutani S, Misawa N, (2010) Cloning and characterization of a novel gene that encodes (S)-beta-bisabolene synthase from ginger, Zingiber officinale. Planta 232: 121-130.
21. Yu F, Okamto S, Nakasone K, Adachi K, Matsuda S, et al. (2008) Molecular cloning and functional characterization of alpha-humulene synthase, a possible key enzyme of zerumbone biosynthesis in shampoo ginger (Zingiber zerumbet Smith). Planta 227: 1291-1299.
22. Yu F, Harada H, Yamasaki K, Okamoto S, Hirase S, et al. (2008) Isolation and functional characterization of a beta-eudesmol synthase, a new sesquiterpene synthase from Zingiber zerumbet Smith. FEBS Lett 582: 565-572.
23. Hiserodt R, Hartman TG, Ho CT, Rosen RT, (1996) Characterization of powdered turmeric by liquid chromatography mass spectrometry and gas chromatography mass spectrometry. Journal of Chromatography A 740: 51-63.
24. Martin VJ, Pitera DJ, Withers ST, Newman JD, Keasling JD, (2003) Engineering a mevalonate pathway in Escherichia coli for production of terpenoids. Nat Biotechnol 21: 796-802.
25. Ro DK, Paradise EM, Ouellet M, Fisher KJ, Newman KL, et al. (2006) Production of the antimalarial drug precursor artemisinic acid in engineered yeast. Nature 440: 940-943.
26. Jiang H, Xie Z, Koo HJ, McLaughlin SP, Timmermann BN, et al. (2006) Metabolic profiling and phylogenetic analysis of medicinal Zingiber species: Tools for authentication of ginger (Zingiber officinale Rosc). Phytochemistry 67: 1673-1685.
27. Adams RP (1995) Identification of Essential Oil Components by Gas Chromatography/Mass Spectroscopy. Illinois, USA: Allured Publishing Co.
28. Arnold K, Bordoli L, Kopp J, Schwede T, (2006) The SWISS-MODEL workspace: a web-based environment for protein structure homology modelling. Bioinformatics 22: 195-201.
29. Leong-Skornickova J, Sida O, Jarolimova V, Sabu M, Fer T, et al. (2007) Chromosome numbers and genome size variation in Indian species of Curcuma (Zingiberaceae). Annals of Botany 100: 505-526.
30. Garms S, Chen F, Boland W, Gershenzon J, Köllner TG, (2012) A single amino acid determines the site of deprotonation in the active center of sesquiterpene synthases SbTPS1 and SbTPS2 from Sorghum bicolor. Phytochemistry 75: 6-13.
31. Zhuang X, Köllner TG, Zhao N, Li G, Jiang Y, et al. (2012) Dynamic evolution of herbivore-induced sesquiterpene biosynthesis in sorghum and related grass crops. Plant J 69: 70-80.
32. Martin DM, Aubourg S, Schouwey MB, Daviet L, Schalk M, et al. (2010) Functional annotation, genome organization and phylogeny of the grapevine (Vitis vinifera) terpene synthase gene family based on genome assembly, FLcDNA cloning, and enzyme assays. BMC Plant Biol 10: 226.
33. Oswald M, Fischer M, Dirninger N, Karst F, (2007) Monoterpenoid biosynthesis in Saccharomyces cerevisiae. FEMS Yeast Res 7: 413-421.
34. Fischer MJ, Meyer S, Claudel P, Bergdoll M, Karst F, (2011) Metabolic engineering of monoterpene synthesis in yeast. Biotechnol Bioeng 108: 1883-1892.
35. de Kraker JW, Franssen MC, de Groot A, Konig WA, Bouwmeester HJ, (1998) (+)-Germacrene A biosynthesis. The committed step in the biosynthesis of bitter sesquiterpene lactones in chicory. Plant Physiol 117: 1381-1392.
36. Gopfert 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.
37. Wang G, Tian L, Aziz N, Broun P, Dai X, et al. (2008) Terpene biosynthesis in glandular trichomes of hop. Plant Physiol 148: 1254-1266.
38. Nakano C, Horinouchi S, Ohnishi Y, (2011) Characterization of a novel sesquiterpene cyclase involved in (+)-caryolan-1-ol biosynthesis in Streptomyces griseus. J Biol Chem 2011: 21.
39. Ponnamperuma K, Croteau R, (1996) Purification and characterization of an NADPH-cytochrome P450 (cytochrome c) reductase from spearmint (Mentha spicata) glandular trichomes. Arch Biochem Biophys 329: 9-16.
40. Hyatt DC, Youn B, Zhao Y, Santhamma B, Coates RM, et al. (2007) Structure of limonene synthase, a simple model for terpenoid cyclase catalysis. Proc Natl Acad Sci U S A 104: 5360-5365.
41. Gennadios HA, Gonzalez V, Di Costanzo L, Li A, Yu F, et al. (2009) Crystal structure of (+)-delta-cadinene synthase from Gossypium arboreum and evolutionary divergence of metal binding motifs for catalysis. Biochemistry 48: 6175-6183.
42. Kiso Y, Suzuki Y, Watanabe N, Oshima Y, Hikino H, (1983) Stereostructure of curlone, a sesquiterpenoid of Curcuma longa rhizomes. Phytochemistry 22: 596-597.
43. Golding BT, Pombo-Villar E, (1992) Structures of α- and β-turmerone. Journal of the Chemical Society, Perkin Transactions 1: 1519-1524.
44. Kreiser W, Korner F, (1999) Stereospecific synthesis of (+)-beta-sesquiphellandrene. Helvetica Chimica Acta 82: 1427-1433.