Molecular cloning and functional characterization of α-humulene synthase, a possible key enzyme of zerumbone biosynthesis in shampoo ginger (Zingiber zerumbet Smith)

Planta

Volumn 227, Issue 6, 2008, Pages 1291-1299

  Yu, Fengnian ^a   Okamto, Sho ^a   Nakasone, Kaoru ^a   Adachi, Kyoko ^b   Matsuda, Satoru ^b   Harada, Hisashi ^b   Misawa, Norihiko ^b   Utsumi, Ryutaro ^a  

^a KINKI UNIVERSITY   (Japan)

^b MARINE BIOTECHNOLOGY INSTITUTE   (Japan)

Author keywords

Humulene; Caryophyllene; Sesquiterpene synthase; Zerumbone biosynthesis (in vivo production); Zingiber

Indexed keywords

ALPHA HUMULENE SYNTHASE, ZINGIBER ZERUMBET; ALPHA-HUMULENE SYNTHASE, ZINGIBER ZERUMBET; COMPLEMENTARY DNA; HUMULENE; LYASE; PLANT DNA; PRIMER DNA; SESQUITERPENE; UNCLASSIFIED DRUG; VEGETABLE PROTEIN; ZERUMBONE;

AMINO ACID SEQUENCE; ARTICLE; CHEMISTRY; ENZYMOLOGY; GENETICS; GINGER; METABOLISM; MOLECULAR GENETICS; NUCLEOTIDE SEQUENCE; OPEN READING FRAME; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; SEQUENCE HOMOLOGY;

AMINO ACID SEQUENCE; CARBON-OXYGEN LYASES; CONSERVED SEQUENCE; DNA PRIMERS; DNA, COMPLEMENTARY; DNA, PLANT; GINGER; MOLECULAR SEQUENCE DATA; OPEN READING FRAMES; PLANT PROTEINS; REVERSE TRANSCRIPTASE POLYMERASE CHAIN REACTION; SEQUENCE HOMOLOGY, AMINO ACID; SESQUITERPENES;

ESCHERICHIA COLI; MAGNOLIOPHYTA; ZINGIBER; ZINGIBER OFFICINALE; ZINGIBER ZERUMBET;

EID: 42149123319     PISSN: 00320935     EISSN: 14322048     Source Type: Journal    
DOI: 10.1007/s00425-008-0700-x     Document Type: Article

References (35)

1. Aharoni A, Giri AP, Deuerlein S, Griepink F, de Kogel WJ, Verstappen FW, Verhoeven HA, Jongsma MA, Schwab W, Bouwmeester HJ (2003) Terpenoid metabolism in wild-type and transgenic Arabidopsis plants. Plant Cell 15:2866-2884
2. Bohlmann J, Meyer-Gauen G, Croteau R (1998) Plant terpenoid synthases: molecular biology and phylogenetic analysis. Proc Natl Acad Sci USA 95:4126-4133
3. Cane DE (1990) Enzymatic Formation of Sesquiterpenes. Chem Rev 90:1089-1103
4. Cane DE (1999) Sesquiterpene biosynthesis: cyclization mechanisms. In: Cane DE (ed) Comprehensive natural products chemistry. Isoprenoids including carotenoids and steroids, Vol 2. Pergamon Press, Oxford, pp 155-200
5. Cha TS, Shah FH (2000) A mesocarp-and species-specific cDNA clone from oil palm encodes for sesquiterpene synthase. Plant Sci 154:153-160
6. Cai Y, Jia JW, Crock J, Lin ZX, Chen XY, Croteau R (2002) A cDNA clone for β-caryophyllene synthase from Artemisia annua. Phytochemistry 61:523-529
7. Chane MJ, Vera R, Chalchat JC (2003) Chemical composition of the essential oil from rhizomes, leaves and flowers of Zingiber zerumbet Smith from Reunion Island. J Essent Oil Res 15:202-205
8. Chen F, Tholl D, Auria JCD, Farooq A, Pichersky E, Gershenzon J (2003) Biosynthesis and emission of terpenoid volatiles from Arabidopsis flowers. Plant Cell 15:481-494
9. Dai JR, Cardellina JH, McMahon JB, Boyd MR (1997) Zerumbone, an HIV-Inhibitory and cytotoxic sesquiterpene of zingiber aromaticum and Z. zerumbet. Nat Prod Lett 10:115-118
10. Dudareva N, Martin D, Kish CM, Kolosova N, Gorenstein N, Fäldt J, Miller B, Bohlmann J (2003) (E)-β-Ocimene and myrcene synthase genes of floral scent biosynthesis in snapdragon: function and expression of three terpene synthase genes of a new terpene synthase subfamily. Plant Cell 15:1227-1243
11. Kakinuma K, Dekishima Y, Matsushima Y, Eguchi T, Misawa N, Takagi M, Kuzuyama T, Seto H (2001) New approach to multiply deuterated isoprenoids using triply engineered Escherichia coli and its potential as a tool for mechanistic enzymology. J Am Chem Soc 123:1238-1239
12. Kirana C, McIntosh GH, Record IR, Jones GP (2003) Antitumor activity of extract of Zingiber aromaticum and its bioactive sesquiterpenoid zerumbone. Nutr Cancer 45:218-225
13. Lichtenthaler HK (1999) The 1-deoxy-D-xylulose-5-phosphate pathway of isoprenoid biosynthesis in plants. Annu Rev Plant Physiol Plant Mol Biol 50:47-65
14. Livak KJ (1997) Comparative Ct method. ABI Prism 7700 Sequence Detection System. User Bulletin no. 2. PE Applied Biosystems
15. Martin VJJ, Pitera DJ, Withers ST, Newman JD, Keasling JD (2003a) Engineering a mevalonate pathway in Escherichia coli for production of terpenoids. Nat Biotechnol 21:796-802
16. Martin DM, Tholl D, Gershenzon J, Bohlmann J (2002) Methyl jasmonate induces traumatic resin ducts, terpenoid resin biosynthesis, and terpenoid accumulation in developing xylem of Norway spruce stems. Plant Physiol 129:1003-1018
17. Martin DM, Gershenzon J, Bohlmann J (2003b) Induction of volatile terpene biosynthesis and diurnal emission by methyl jasmonate in foliage of Norway spruce. Plant Physiol 132:1586-1599
18. Miller B, Madilao LL, Ralph S, Bohlmann J (2005) Insect-induced conifer defense. White pine weevil and methyl jasmonate induce traumatic resinosis, de novo formed volatile emissions, and accumulation of terpenoid synthase and putative octadecanoid pathway transcripts in Sitka spruce. Plant Physiol 137:369-382
19. Mattiacci L, Rocca BA, Scascighini N, D'Alessandro M, Hern A, Dorn S (2001) Systemically induced plant volatiles emitted at the time of danger. J Chem Ecol 27:2233-2252
20. Mau CJ, West CA (1994) Cloning of casbene synthase cDNA: evidence for conserved structural features among terpenoid cyclases in plants. Proc Natl Acad Sci USA 91:8497-8501
21. Murakami A, Tanaka T, Lee JY, Surh YJ, Kim HW, Kawabata K, Nakamura Y, Jiwajinda S, Ohigashi H (2004) Zerumbone suppresses skin tumor initiation and promotion stages in mice: involvement of induction of anti-oxidative and phase II drug metabolizing enzymes and inhibition of NF-kB-mediated cyclooxygenase-2 expression. Int J Cancer 110:481-490
22. Murakami A, Takahashi D, Kinoshita T, Koshimizu K, Kim HW, Yoshihiro A, Nakamura Y, Jiwajinda S, Terao J, Ohigashi H (2002) Zerumbone, a Southeast Asian ginger sesquiterpene, markedly suppresses free radical generation, proinflammatory protein production and cancer cell proliferation accompanied by apoptosis: the α, β-unsaturated carbonyl group is a prerequisite. Carcinogenesis 23:795-802
23. Ozaki Y, Kawahara N, Harada M (1991) Anti-inflammatory effect of Zingiber cassumunar Roxb. and its active principles. Chem Pharm Bull 39:2353-2356
24. Rodriguez-Saona C, Crafts-Brandner SJ, Canas LA (2003) Volatile emissions triggered by multiple herbivore damage: beet armyworm and whitefly feeding on cotton plants. J Chem Ecol 29:2521-2532
25. 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
26. Sharifah-Sakinah SA, Tri-Handayani S, Azimahtol-Hawariah LP (2007) Zerumbone induced apoptosis in liver cancer cells via modulation of Bax/Bcl-2 ratio. Cancer Cell Int 7:4-15
27. Schnee C, Köllner TG, Gershenzon J, Degenhardt J (2002) The Maize Gene terpene synthase 1 encodes a sesquiterpene synthase catalyzing the formation of (E)-β- farnesene, (E)-nerolidol, and (E,E)-farnesol after herbivore damage. Plant Physiol 130:2049-2060
28. Steele CL, Katoh S, Bohlmann J, Croteau R (1998) Regulation of oleoresinosis in grand fir (Abies grandis): differential transcriptional control of monoterpene, sesquiterpene, and diterpene synthase genes in response to wounding. Plant Physiol 116:1497-1504
29. Suga T, Ohta S, Munesada K, Ide N, Kurokawa M, Shimizu M, Ohta E (1993) Endogenous pine wood nematicidal substance inpines, Pinus massioniana, P. strobus and P. palustris. Phytochemistry 33:1395-1401
30. Takayuki S (1994) Pest control chemicals against pine wood nematodes. United States Patent: 5314693
31. Takagi M, Kuzuyama T, Takahashi S, Seto H (2000) A gene cluster for the mevalonate pathway from Streptomyces sp. strain CL190. J Bacteriol 182:4153-4157
32. Trapp S, Croteau R (2001) Genomic organization of plant terpene synthases and molecular evolutionary implications. Genetics 158:811-832
33. Xian MJ, Ito K, Nakazato T, Shimizu T, Chen CK, Yamato K, Murakami A, Ohigashi H, Ikeda Y, Kizaki M (2007) Zerumbone, a bioactive sesquiterpene, induces G2/M cell cycle arrest and apoptosis in leukemia cells via a Fas- and mitochondria -mediated pathway. Cancer Sci 98:118-126
34. Yin S, Mei L, Newman J, Back K, Chappell J (1997) Regulation of sesquiterpene cyclase gene expression. Plant Physiol 115:437-451
35. Yoon SH, Lee YM, Kim JE, Lee SH, Lee JH, Kim JY, Jung KH, Shin YC, Keasling JD, Kim SW (2006) Enhanced lycopene production in Escherichia coli engineered to synthesize isopentenyl diphosphate and dimethylallyl diphosphate from mevalonate. Biotechnol Bioeng 94:1025-1032