메뉴 건너뛰기




Volumn 68, Issue 6, 2011, Pages 1033-1040

Zingiber zerumbet CYP71BA1 catalyzes the conversion of α-humulene to 8-hydroxy-α-humulene in zerumbone biosynthesis

Author keywords

8 hydroxy humulene; CYP71BA1; Metabolic engineering; Mevalonate pathway; P450; Zingiber zerumbet Smith

Indexed keywords

8 HYDROXY ALPHA HUMULENE; CELL PROTEIN; CYTOCHROME P450; CYTOCHROME P450 71BA1; HUMULENE; MEVALONIC ACID; PROTEIN ZSS1; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG; ZERUMBONE;

EID: 79953698422     PISSN: 1420682X     EISSN: 14209071     Source Type: Journal    
DOI: 10.1007/s00018-010-0506-4     Document Type: Article
Times cited : (46)

References (27)
  • 1
    • 0030812283 scopus 로고    scopus 로고
    • Zerumbone, an HIV-inhibitory and cytotoxic sesquiterpene of Zingiber aromaticum and Z. zerumbet
    • JR Dai JH Cardellina JB McMahon MR Boyd 1997 Zerumbone, an HIV-inhibitory and cytotoxic sesquiterpene of Zingiber aromaticum and Z. zerumbet Nat Prod Lett 10 115 118 1:CAS:528:DyaK2sXkt12ht7o%3D (Pubitemid 27292336)
    • (1997) Natural Product Letters , vol.10 , Issue.2 , pp. 115-118
    • Dai, J.-R.1    Cardellina II, J.H.2    McMahon, J.B.3    Boyd, M.R.4
  • 2
    • 0025992016 scopus 로고
    • Anti-inflammatory effect of Zingiber cassumunar Roxb. and its active principles
    • 1:CAS:528:DyaK38XhsFGgtw%3D%3D 1804548
    • Y Ozaki N Kawahara M Harada 1991 Anti-inflammatory effect of Zingiber cassumunar Roxb. and its active principles Chem Pharm Bull 39 2353 2356 1:CAS:528:DyaK38XhsFGgtw%3D%3D 1804548
    • (1991) Chem Pharm Bull , vol.39 , pp. 2353-2356
    • Ozaki, Y.1    Kawahara, N.2    Harada, M.3
  • 3
    • 0036258778 scopus 로고    scopus 로고
    • 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
    • A Murakami D Takahashi T Kinoshita K Koshimizu HW Kim A Yoshihiro Y Nakamura S Jiwajinda J Terao H Ohigashi 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 1:CAS:528:DC%2BD38XktFyqsLg%3D 10.1093/carcin/23.5.795 12016152 (Pubitemid 34567518)
    • (2002) Carcinogenesis , vol.23 , Issue.5 , pp. 795-802
    • Murakami, A.1    Takahashi, D.2    Kinoshita, T.3    Koshimizu, K.4    Kim, H.W.5    Yoshihiro, A.6    Nakamura, Y.7    Jiwajinda, S.8    Terao, J.9    Ohigashi, H.10
  • 4
    • 0041510434 scopus 로고    scopus 로고
    • Antitumor activity of extract of Zingiber aromaticum and its bioactive sesquiterpenoid zerumbone
    • C Kirana GH McIntosh IR Record GP Jones 2003 Antitumor activity of extract of Zingiber aromaticum and its bioactive sesquiterpenoid zerumbone Nutr Cancer 45 218 225 1:CAS:528:DC%2BD3sXnsVequ7w%3D 10.1207/S15327914NC4502-12 12881017 (Pubitemid 37022796)
    • (2003) Nutrition and Cancer , vol.45 , Issue.2 , pp. 218-225
    • Kirana, C.1    McIntosh, G.H.2    Record, I.R.3    Jones, G.P.4
  • 5
    • 34247218059 scopus 로고    scopus 로고
    • Zerumbone induced apoptosis in liver cancer cells via modulation of Bax/ Bcl-2 ratio
    • DOI 10.1186/1475-2867-7-4
    • SA Sharifah-Sakinah S Tri-Handayani LP Azimahtol-Hawariah 2007 Zerumbone induced apoptosis in liver cancer cells via modulation of Bax/Bcl-2 ratio Cancer Cell Int 7 4 15 10.1186/1475-2867-7-4 (Pubitemid 46605896)
    • (2007) Cancer Cell International , vol.7 , pp. 4
    • Sakinah, S.A.S.1    Tri Handayani, S.2    Hawariah, L.P.A.3
  • 6
    • 33751332527 scopus 로고    scopus 로고
    • Zerumbone, a bioactive sesquiterpene, induces G2/M cell cycle arrest and apoptosis in leukemia cells via a Fas- and mitochondria-mediated pathway
    • DOI 10.1111/j.1349-7006.2006.00362.x
    • MJ Xian K Ito T Nakazato T Shimizu CK Chen K Yamato A Murakami H Ohigashi Y Ikeda M Kizaki 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 1:CAS:528:DC%2BD2sXht1Gitrs%3D 10.1111/j.1349-7006.2006.00362.x 17129359 (Pubitemid 44803930)
    • (2007) Cancer Science , vol.98 , Issue.1 , pp. 118-126
    • Xian, M.1    Ito, K.2    Nakazato, T.3    Shimizu, T.4    Chen, C.-K.5    Yamato, K.6    Murakami, A.7    Ohigashi, H.8    Ikeda, Y.9    Kizaki, M.10
  • 7
    • 2442654176 scopus 로고    scopus 로고
    • Zerumbone, a sesquiterpene in subtropical ginger, suppresses skin tumor initiation and promotion stages in ICR mice
    • DOI 10.1002/ijc.20175
    • A Murakami T Tanaka JY Lee YJ Surh HW Kim K Kawabata Y Nakamura S Jiwajinda H Ohigashi 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 1:CAS:528:DC%2BD2cXktlKktLs%3D 10.1002/ijc.20175 15122579 (Pubitemid 38658012)
    • (2004) International Journal of Cancer , vol.110 , Issue.4 , pp. 481-490
    • Murakami, A.1    Tanaka, T.2    Lee, J.-Y.3    Surh, Y.-J.4    Kim, H.W.5    Kawabata, K.6    Nakamura, Y.7    Jiwajinda, S.8    Ohigashi, H.9
  • 8
    • 0038391517 scopus 로고    scopus 로고
    • Engineering a mevalonate pathway in Escherichia coli for production of terpenoids
    • DOI 10.1038/nbt833
    • VJJ Martin DJ Pitera ST Withers JD Newman JD Keasling 2003 Engineering a mevalonate pathway in Escherichia coli for production of terpenoids Nat Biotechnol 21 796 802 1:CAS:528:DC%2BD3sXkvFertb4%3D 10.1038/nbt833 12778056 (Pubitemid 36791399)
    • (2003) Nature Biotechnology , vol.21 , Issue.7 , pp. 796-802
    • Martin, V.J.J.1    Piteral, D.J.2    Withers, S.T.3    Newman, J.D.4    Keasling, J.D.5
  • 9
    • 33847309176 scopus 로고    scopus 로고
    • Balancing a heterologous mevalonate pathway for improved isoprenoid production in Escherichia coli
    • DOI 10.1016/j.ymben.2006.11.002, PII S1096717606001108
    • DJ Pitera CJ Paddon JD Newman JD Keasling 2007 Balancing a heterologous mevalonate pathway for improved isoprenoid production in Escherichia coli Metab Eng 9 193 207 1:CAS:528:DC%2BD2sXhvVyktbg%3D 10.1016/j.ymben.2006.11.002 17239639 (Pubitemid 46329511)
    • (2007) Metabolic Engineering , vol.9 , Issue.2 , pp. 193-207
    • Pitera, D.J.1    Paddon, C.J.2    Newman, J.D.3    Keasling, J.D.4
  • 10
    • 33750557880 scopus 로고    scopus 로고
    • High-level production of amorpha-4,11-diene in a two-phase partitioning bioreactor of metabolically engineered Escherichia coli
    • DOI 10.1002/bit.21017
    • JD Newman J Marshal M Chang F Nowroozi E Paradise D Pitera KL Newman JD Keasling 2006 High-level production of amorpha-4,11-diene in a two-phase partitioning bioreactor of metabolically engineering Escherichia coli Biotechnol Bioeng 95 684 691 1:CAS:528:DC%2BD28XhtFarsbvF 10.1002/bit.21017 16878333 (Pubitemid 44671470)
    • (2006) Biotechnology and Bioengineering , vol.95 , Issue.4 , pp. 684-691
    • Newman, J.D.1    Marshall, J.2    Chang, M.3    Nowroozi, F.4    Paradise, E.5    Pitera, D.6    Newman, K.L.7    Keasling, J.D.8
  • 11
    • 70349668766 scopus 로고    scopus 로고
    • Novel approaches and achievements in biosynthesis of functional isoprenoids in Escherichia coli
    • 1:CAS:528:DC%2BD1MXht1Sqs7jK 10.1007/s00253-009-2166-6 19672590
    • H Harada N Misawa 2009 Novel approaches and achievements in biosynthesis of functional isoprenoids in Escherichia coli Appl Microbiol Biotechnol 84 1021 1031 1:CAS:528:DC%2BD1MXht1Sqs7jK 10.1007/s00253-009-2166-6 19672590
    • (2009) Appl Microbiol Biotechnol , vol.84 , pp. 1021-1031
    • Harada, H.1    Misawa, N.2
  • 12
    • 42149123319 scopus 로고    scopus 로고
    • Molecular cloning and functional characterization of α-humulene synthase, a possible key enzyme of zermbone biosynthesis in shampoo ginger (Zingiber zerumbet Smith)
    • 1:CAS:528:DC%2BD1cXks1Ght74%3D 10.1007/s00425-008-0700-x 18273640
    • FN Yu S Okamoto K Nakasone K Adachi S Matsuda H Harada N Misawa R Utsumi 2008 Molecular cloning and functional characterization of α-humulene synthase, a possible key enzyme of zermbone biosynthesis in shampoo ginger (Zingiber zerumbet Smith) Planta 227 1291 1299 1:CAS:528:DC%2BD1cXks1Ght74%3D 10.1007/s00425-008-0700-x 18273640
    • (2008) Planta , vol.227 , pp. 1291-1299
    • Yu, F.N.1    Okamoto, S.2    Nakasone, K.3    Adachi, K.4    Matsuda, S.5    Harada, H.6    Misawa, N.7    Utsumi, R.8
  • 13
    • 2642547256 scopus 로고    scopus 로고
    • Molecular cloning and characterization of a cytochrome P450 taxoid 2α-hydroxylase involved in Taxol biosynthesis
    • DOI 10.1016/j.abb.2004.04.016, PII S0003986104002334
    • M Chau R Croteau 2004 Molecular cloning and characterization of a cytochrome P450 taxoid 2α-hydroxylase involved in Taxol biosynthesis Arch Biochem Biophys 27 48 57 10.1016/j.abb.2004.04.016 (Pubitemid 38725913)
    • (2004) Archives of Biochemistry and Biophysics , vol.427 , Issue.1 , pp. 48-57
    • Chau, M.1    Croteau, R.2
  • 14
    • 0035883986 scopus 로고    scopus 로고
    • Cloning, heterologous expression, and functional characterization of 5-epi-Aristolochene-1,3-Dihydroxylase from tobacco (Nicotiana tabacum)
    • DOI 10.1006/abbi.2001.2483
    • L Ralston ST Kwon M Schoenbeck J Ralston DJ Schenk RM Coates J Chappell 2001 Cloning, heterologous expression, and functional characterization of 5-epi-aristolochene-1, 3-dihydroxylase from tobacco (Nicotiana tabacum) Arch Biochem Biophys 393 222 235 1:CAS:528:DC%2BD3MXmslGhtL8%3D 10.1006/abbi.2001. 2483 11556809 (Pubitemid 32907179)
    • (2001) Archives of Biochemistry and Biophysics , vol.393 , Issue.2 , pp. 222-235
    • Ralston, L.1    Kwon, S.-T.2    Schoenbeck, M.3    Ralston, J.4    Schenk, D.J.5    Coates, R.M.6    Chappell, J.7
  • 15
    • 0034771751 scopus 로고    scopus 로고
    • Molecular cloning and functional identification of (+)-δ-cadinene- 8-hydroxylase, a cytochrome p450 mono-oxygenase (cyp706b1) of cotton sesquiterpene biosynthesis
    • DOI 10.1046/j.1365-313X.2001.01133.x
    • P Luo YH Wang GD Wang M Essenberg XY Chen 2001 Molecular cloning and functional identification of (+)-delta-cadinene-8-hydroxylase, a cytochrome P450 mono-oxygenase (CYP706B1) of cotton sesquiterpene biosynthesis Plant J 28 95 104 1:CAS:528:DC%2BD3MXosVWqs70%3D 10.1046/j.1365-313X.2001.01133.x 11696190 (Pubitemid 33011512)
    • (2001) Plant Journal , vol.28 , Issue.1 , pp. 95-104
    • Luo, P.1    Wang, Y.-H.2    Wang, G.-D.3    Essenberg, M.4    Chen, X.-Y.5
  • 16
    • 32344437343 scopus 로고    scopus 로고
    • Artemisia annua L. (Asteraceae) trichome-specific cDNAs reveal CYP71AV1, a cytochrome P450 with a key role in the biosynthesis of the antimalarial sesquiterpene lactone artemisinin
    • DOI 10.1016/j.febslet.2006.01.065, PII S0014579306001207
    • KH Teoh DR Polichuk DW Reed G Nowak PS Covello 2006 Artemisia annua L. (Asteraceae) trichome-specific cDNAs reveal CYP71AV1, a cytochrome P450 with a key role in the biosynthesis of the antimalarial sesquiterpene lactone artemisinin FEBS Lett 580 1411 1416 1:CAS:528:DC%2BD28Xhs1Snt7g%3D 10.1016/j.febslet.2006.01.065 16458889 (Pubitemid 43222008)
    • (2006) FEBS Letters , vol.580 , Issue.5 , pp. 1411-1416
    • Teoh, K.H.1    Polichuk, D.R.2    Reed, D.W.3    Nowak, G.4    Covello, P.S.5
  • 17
    • 0029776005 scopus 로고    scopus 로고
    • Yeast expression of animal and plant P450s in optimized redox environments
    • D Pompon B Louerat A Bronine P Urban 1996 Yeast expression of animal and plant P450s in optimized redox environments Methods Enzymol 272 51 64 1:CAS:528:DyaK28XmvFKltLo%3D 10.1016/S0076-6879(96)72008-6 8791762 (Pubitemid 26299867)
    • (1996) Methods in Enzymology , vol.272 , pp. 51-64
    • Pompon, D.1    Louerat, B.2    Bronine, A.3    Urban, P.4
  • 18
    • 0030852872 scopus 로고    scopus 로고
    • Cloning, yeast expression, and characterization of the coupling of two distantly related Arabidopsis thaliana NADPH-cytochrome P450 reductases with P450 CYP73A5
    • DOI 10.1074/jbc.272.31.19176
    • P Urban C Mignotte M Kazmaier F Delorme D Pompon 1997 Cloning, yeast expression, and characterization of the coupling of two distantly related Arabidopsis thaliana NADPH-Cytochrome P450 reductases with P450 CYP73A5 J Biol Chem 272 19176 19186 1:CAS:528:DyaK2sXltFSmtbk%3D 10.1074/jbc.272.31.19176 9235908 (Pubitemid 27337705)
    • (1997) Journal of Biological Chemistry , vol.272 , Issue.31 , pp. 19176-19186
    • Urban, P.1    Mignotte, C.2    Kazmaier, M.3    Delorme, F.4    Pompon, D.5
  • 19
    • 58149151350 scopus 로고    scopus 로고
    • Efficient synthesis of functional isoprenoids from acetoacetate through metabolic pathway-engineered Escherichia coli
    • 1:CAS:528:DC%2BD1cXhsFartrfL 10.1007/s00253-008-1724-7
    • H Harada FN Yu S Okamoto N Misawa R Utsumi 2009 Efficient synthesis of functional isoprenoids from acetoacetate through metabolic pathway-engineered Escherichia coli Appl Micro Biotech 81 915 925 1:CAS:528:DC%2BD1cXhsFartrfL 10.1007/s00253-008-1724-7
    • (2009) Appl Micro Biotech , vol.81 , pp. 915-925
    • Harada, H.1    Yu, F.N.2    Okamoto, S.3    Misawa, N.4    Utsumi, R.5
  • 20
    • 0023918714 scopus 로고
    • On the membrane topology of vertebrate cytochrome P-450 proteins
    • 1:CAS:528:DyaL1cXitFOqtLc%3D 2834360
    • DR Nelson HW Strobel 1988 On the membrane topology of vertebrate cytochrome P-450 proteins J Biol Chem 263 6038 6050 1:CAS:528:DyaL1cXitFOqtLc%3D 2834360
    • (1988) J Biol Chem , vol.263 , pp. 6038-6050
    • Nelson, D.R.1    Strobel, H.W.2
  • 21
    • 0029621245 scopus 로고
    • Diversity and evolution of plant P450 and P450-reductases
    • F Durst DR Nelson 1995 Diversity and evolution of plant P450 and P450-reductases Drug Metab Drug Interact 12 189 206 1:CAS:528: DyaK28XlsFCgsA%3D%3D (Pubitemid 26032204)
    • (1995) Drug Metabolism and Drug Interactions , vol.12 , Issue.3-4 , pp. 189-206
    • Durst, F.1    Nelson, D.R.2
  • 22
    • 0031766440 scopus 로고    scopus 로고
    • Molecular-genetic analysis of plant cytochrome P450-dependent monooxygenases
    • DOI 10.1146/annurev.arplant.49.1.311
    • C Chapple 1998 Molecular genetic analysis of plant cytochrome P450-dependent monooxygenases Annu Rev Plant Physiol Plant Mol Biol 49 311 343 1:CAS:528:DyaK1cXjvVShtbg%3D 10.1146/annurev.arplant.49.1.311 15012237 (Pubitemid 28514495)
    • (1998) Annual Review of Plant Physiology and Plant Molecular Biology , vol.49 , pp. 311-343
    • Chapple, C.1
  • 23
    • 35748931196 scopus 로고    scopus 로고
    • Functional Characterization of Premnaspirodiene Oxygenase, a Cytochrome P450 Catalyzing Regio- And Stereo-specific Hydroxylations of Diverse Sesquiterpene Substrates
    • DOI 10.1074/jbc.M703378200
    • S Takahashi YS Yeo Y Zhao PE O'Maille BT Greenhagen JP Noel RM Coates J Chappell 2007 Functional characterization of premnaspirodiene oxygenase, a cytochrome P450 catalyzing regio- and stereo-specific hydroxylations of diverse sesquiterpene substrates J Biol Chem 282 31744 31754 1:CAS:528: DC%2BD2sXhtFyku77I 10.1074/jbc.M703378200 17715131 (Pubitemid 350044865)
    • (2007) Journal of Biological Chemistry , vol.282 , Issue.43 , pp. 31744-31754
    • Takahashi, S.1    Yeo, Y.-S.2    Zhao, Y.3    O'Maille, P.E.4    Greenhagen, B.T.5    Noel, J.P.6    Coates, R.M.7    Chappell, J.8
  • 24
    • 77952783256 scopus 로고    scopus 로고
    • Biochemical conservation and evolution of germacrene A oxidase in Asteraceae
    • 1:CAS:528:DC%2BC3cXmtlygsLw%3D 10.1074/jbc.M110.111757 20351109
    • DT Nguyen JC Gopfert N Ikezawa G MacNevin M Kathiresan J Conrad O Spring DK Ro 2010 Biochemical conservation and evolution of germacrene A oxidase in Asteraceae J Biol Chem 285 16588 16598 1:CAS:528:DC%2BC3cXmtlygsLw%3D 10.1074/jbc.M110.111757 20351109
    • (2010) J Biol Chem , vol.285 , pp. 16588-16598
    • Nguyen, D.T.1    Gopfert, J.C.2    Ikezawa, N.3    MacNevin, G.4    Kathiresan, M.5    Conrad, J.6    Spring, O.7    Ro, D.K.8
  • 25
    • 34247182988 scopus 로고    scopus 로고
    • Engineering Escherichia coli for production of functionalized terpenoids using plant P450s
    • DOI 10.1038/nchembio875, PII NCHEMBIO875
    • MC Chang RA Eachus W Trieu DK Ro JD Keasling 2007 Engineering Escherichia coli for production of functionalized terpenoids using plant P450s Nat Chem Biol 3 274 277 1:CAS:528:DC%2BD2sXkt1Kjsrc%3D 10.1038/nchembio875 17438551 (Pubitemid 46625834)
    • (2007) Nature Chemical Biology , vol.3 , Issue.5 , pp. 274-277
    • Chang, M.C.Y.1    Eachus, R.A.2    Trieu, W.3    Ro, D.-K.4    Keasling, J.D.5
  • 27
    • 39749180988 scopus 로고    scopus 로고
    • Isolation and functional characterization of a β-eudesmol synthase, a new sesquiterpene synthase from Zingiber zerumbet Smith
    • 10.1016/j.febslet.2008.01.020
    • FN Yu H Harada K Yamasaki S Okamoto S Hirase Y Tanaka N Misawa R Utsumi 2008 Isolation and functional characterization of a β-eudesmol synthase, a new sesquiterpene synthase from Zingiber zerumbet Smith FEBS Lett 582 537 542 10.1016/j.febslet.2008.01.020
    • (2008) FEBS Lett , vol.582 , pp. 537-542
    • Yu, F.N.1    Harada, H.2    Yamasaki, K.3    Okamoto, S.4    Hirase, S.5    Tanaka, Y.6    Misawa, N.7    Utsumi, R.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.