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Volumn 585, Issue 7, 2011, Pages 1031-1036

Molecular characterization of an oxidosqualene cyclase that yields shionone, a unique tetracyclic triterpene ketone of Aster tataricus

Author keywords

Aster tataricus; Asteraceae; Evolution; Oxidosqualene cyclase; Shionone; Triterpene

Indexed keywords

4 EPISHIONONE; BETA AMYRIN; COMPLEMENTARY DNA; DAMMARA 20,24 DIENOL; FRIEDELIN; LANOSTEROL SYNTHASE; SHIONONE; SHIONONE SYNTHASE; SYNTHETASE; TRITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 79953254244     PISSN: 00145793     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.febslet.2011.02.037     Document Type: Article
Times cited : (29)

References (34)
  • 2
    • 0742307297 scopus 로고    scopus 로고
    • On the origins of triterpenoid skeletal diversity
    • DOI 10.1016/j.phytochem.2003.11.014
    • R. Xu, G.C. Fazio, and S.P. Matsuda On the origins of triterpenoid skeletal diversity Phytochemistry 65 2004 261 291 (Pubitemid 38147342)
    • (2004) Phytochemistry , vol.65 , Issue.3 , pp. 261-291
    • Xu, R.1    Fazio, G.C.2    Matsuda, S.P.T.3
  • 6
    • 79953252021 scopus 로고
    • La shionone. Étude structurale. (IV). le cycle D. Structure de la shionone
    • Y. Moriyama, Y. Tanahashi, T. Takahashi, and G. Ourisson La shionone. Étude structurale. (IV). Le cycle D. Structure de la shionone Bull. Soc. Chim. Fr. 1968 2890 2894
    • (1968) Bull. Soc. Chim. Fr. , pp. 2890-2894
    • Moriyama, Y.1    Tanahashi, Y.2    Takahashi, T.3    Ourisson, G.4
  • 7
    • 0027146637 scopus 로고
    • Isolation of an Arabidopsis thaliana gene encoding cycloartenol synthase by functional expression in a yeast mutant lacking lanosterol synthase by the use of a chromatographic screen
    • DOI 10.1073/pnas.90.24.11628
    • E.J. Corey, S.P. Matsuda, and B. Bartel Isolation of an Arabidopsis thaliana gene encoding cycloartenol synthase by functional expression in a yeast mutant lacking lanosterol synthase by the use of a chromatographic screen Proc. Natl. Acad. Sci. USA 90 1993 11628 11632 (Pubitemid 24008692)
    • (1993) Proceedings of the National Academy of Sciences of the United States of America , vol.90 , Issue.24 , pp. 11628-11632
    • Corey, E.J.1    Matsuda, S.P.T.2    Bartel, B.3
  • 9
    • 33745635730 scopus 로고    scopus 로고
    • Plant lanosterol synthase: Divergence of the sterol and triterpene biosynthetic pathways in eukaryotes
    • DOI 10.1093/pcp/pcj032
    • S. Sawai, T. Akashi, N. Sakurai, H. Suzuki, D. Shibata, S. Ayabe, and T. Aoki Plant lanosterol synthase: divergence of the sterol and triterpene biosynthetic pathways in eukaryotes Plant Cell Physiol. 47 2006 673 677 (Pubitemid 43987613)
    • (2006) Plant and Cell Physiology , vol.47 , Issue.5 , pp. 673-677
    • Sawai, S.1    Akashi, T.2    Sakurai, N.3    Suzuki, H.4    Shibata, D.5    Ayabe, S.-I.6    Aoki, T.7
  • 10
    • 29244486464 scopus 로고    scopus 로고
    • Functional and structural analysis of genes encoding oxidosqualene cyclases of Lotus japonicus
    • DOI 10.1016/j.plantsci.2005.08.027, PII S0168945205003018
    • S. Sawai, T. Shindo, S. Sato, T. Kaneko, S. Tabata, S. Ayabe, and T. Aoki Functional and structural analysis of genes encoding oxidosqualene cyclases of Lotus japonicus Plant Sci. 170 2006 247 257 (Pubitemid 41831183)
    • (2006) Plant Science , vol.170 , Issue.2 , pp. 247-257
    • Sawai, S.1    Shindo, T.2    Sato, S.3    Kaneko, T.4    Tabata, S.5    Ayabe, S.-I.6    Aoki, T.7
  • 11
    • 34548757971 scopus 로고    scopus 로고
    • An oxidosqualene cyclase makes numerous products by diverse mechanisms: A challenge to prevailing concepts of triterpene biosynthesis
    • DOI 10.1021/ja073133u
    • S. Lodeiro, Q. Xiong, W.K. Wilson, M.D. Kolesnikova, C.S. Onak, and S.P. Matsuda An oxidosqualene cyclase makes numerous products by diverse mechanisms: a challenge to prevailing concepts of triterpene biosynthesis J. Am. Chem. Soc. 129 2007 11213 11222 (Pubitemid 47435724)
    • (2007) Journal of the American Chemical Society , vol.129 , Issue.36 , pp. 11213-11222
    • Lodeiro, S.1    Xiong, Q.2    Wilson, W.K.3    Kolesnikova, M.D.4    Onak, C.S.5    Matsuda, S.P.T.6
  • 12
    • 1642340664 scopus 로고    scopus 로고
    • Enzymatic Cyclization of 22,23-Dihydro-2,3-oxidosqualene into Euph-7-en-3β-ol and Bacchar-12-en-3β-ol by Recombinant β-Amyrin Synthase
    • DOI 10.1021/ja031955v
    • I. Abe, Y. Sakano, H. Tanaka, W. Lou, H. Noguchi, M. Shibuya, and Y. Ebizuka Enzymatic cyclization of 22, 23-dihydro-2,3-oxidosqualene into euph-7-en-3β-ol and bacchar-12-en-3β-ol by recombinant β-amyrin synthase J. Am. Chem. Soc. 126 2004 3426 3427 (Pubitemid 38366725)
    • (2004) Journal of the American Chemical Society , vol.126 , Issue.11 , pp. 3426-3427
    • Abe, I.1    Sakano, Y.2    Tanaka, H.3    Lou, W.4    Noguchi, H.5    Shibuya, M.6    Ebizuka, Y.7
  • 13
    • 58149149531 scopus 로고    scopus 로고
    • Biosynthesis of baccharis oxide, a triterpene with a 3, 10-oxide bridge in the A-ring
    • M. Shibuya, A. Sagara, A. Saitoh, T. Kushiro, and Y. Ebizuka Biosynthesis of baccharis oxide, a triterpene with a 3, 10-oxide bridge in the A-ring Org. Lett. 10 2008 5071 5074
    • (2008) Org. Lett. , vol.10 , pp. 5071-5074
    • Shibuya, M.1    Sagara, A.2    Saitoh, A.3    Kushiro, T.4    Ebizuka, Y.5
  • 14
    • 77956918452 scopus 로고    scopus 로고
    • Cloning and characterization of oxidosqualene cyclases from Kalanchoe daigremontiana: Enzymes catalyzing up to 10 rearrangement steps yielding friedelin and other triterpenoids
    • Z. Wang, T. Yeats, H. Han, and R. Jetter Cloning and characterization of oxidosqualene cyclases from Kalanchoe daigremontiana: enzymes catalyzing up to 10 rearrangement steps yielding friedelin and other triterpenoids J. Biol. Chem. 285 2010 29703 29712
    • (2010) J. Biol. Chem. , vol.285 , pp. 29703-29712
    • Wang, Z.1    Yeats, T.2    Han, H.3    Jetter, R.4
  • 15
    • 0032529028 scopus 로고    scopus 로고
    • β-Amyrin synthase. Cloning of oxidosqualene cyclase that catalyzes the formation of the most popular triterpene among higher plants
    • DOI 10.1046/j.1432-1327.1998.2560238.x
    • T. Kushiro, M. Shibuya, and Y. Ebizuka β-Amyrin synthase - cloning of oxidosqualene cyclase that catalyzes the formation of the most popular triterpene among higher plants Eur. J. Biochem. 256 1998 238 244 (Pubitemid 28399118)
    • (1998) European Journal of Biochemistry , vol.256 , Issue.1 , pp. 238-244
    • Kushiro, T.1    Shibuya, M.2    Ebizuka, Y.3
  • 16
    • 34547781750 scopus 로고    scopus 로고
    • MEGA4: Molecular Evolutionary Genetics Analysis (MEGA) software version 4.0
    • DOI 10.1093/molbev/msm092
    • K. Tamura, J. Dudley, M. Nei, and S. Kumar MEGA4: molecular evolutionary genetics analysis (MEGA) software version 4.0 Mol. Biol. Evol. 24 2007 1596 1599 (Pubitemid 47236692)
    • (2007) Molecular Biology and Evolution , vol.24 , Issue.8 , pp. 1596-1599
    • Tamura, K.1    Dudley, J.2    Nei, M.3    Kumar, S.4
  • 17
    • 3042666256 scopus 로고    scopus 로고
    • MUSCLE: Multiple sequence alignment with high accuracy and high throughput
    • DOI 10.1093/nar/gkh340
    • R.C. Edgar MUSCLE: multiple sequence alignment with high accuracy and high throughput Nucleic Acids Res. 32 2004 1792 1797 (Pubitemid 38832724)
    • (2004) Nucleic Acids Research , vol.32 , Issue.5 , pp. 1792-1797
    • Edgar, R.C.1
  • 18
    • 0027979831 scopus 로고
    • Active site mapping of affinity-labeled rat oxidosqualene cyclase
    • I. Abe, and G.D. Prestwich Active site mapping of affinity-labeled rat oxidosqualene cyclase J. Biol. Chem. 269 1994 802 804 (Pubitemid 24032444)
    • (1994) Journal of Biological Chemistry , vol.269 , Issue.2 , pp. 802-804
    • Abe, I.1    Prestwich, G.D.2
  • 20
    • 0034718068 scopus 로고    scopus 로고
    • Mutational studies on triterpene synthases: Engineering lupeol synthase into β-amyrin synthase
    • DOI 10.1021/ja0010709
    • T. Kushiro, M. Shibuya, K. Masuda, and Y. Ebizuka Mutational studies on triterpene syntheses: engineering lupeol synthase into β-amyrin synthase J. Am. Chem. Soc. 122 2000 6816 6824 (Pubitemid 30639854)
    • (2000) Journal of the American Chemical Society , vol.122 , Issue.29 , pp. 6816-6824
    • Kushiro, T.1    Shibuya, M.2    Masuda, K.3    Ebizuka, Y.4
  • 21
    • 0032977239 scopus 로고    scopus 로고
    • (20R, 23E)-Eupha-8, 23-diene-3β, 25-diol from Tripetalum cymosum
    • Y.W. Leong, and L.J. Harrison (20R, 23E)-Eupha-8, 23-diene-3β, 25-diol from Tripetalum cymosum Phytochemistry 50 1999 849 857
    • (1999) Phytochemistry , vol.50 , pp. 849-857
    • Leong, Y.W.1    Harrison, L.J.2
  • 24
    • 41549107616 scopus 로고    scopus 로고
    • Engineering triterpene production in Saccharomyces cerevisiae-β- amyrin synthase from Artemisia annua
    • DOI 10.1111/j.1742-4658.2008.06343.x
    • J. Kirby, D.W. Romanini, E.M. Paradise, and J.D. Keasling Engineering triterpene production in Saccharomyces cerevisiae - β-amyrin synthase from Artemisia annua FEBS J. 275 2008 1852 1859 (Pubitemid 351464004)
    • (2008) FEBS Journal , vol.275 , Issue.8 , pp. 1852-1859
    • Kirby, J.1    Romanini, D.W.2    Paradise, E.M.3    Keasling, J.D.4
  • 25
    • 43749115788 scopus 로고
    • Labdane derivatives and flavones from Gutierrezia dracunculoides
    • F. Bohlmann, M. Grenz, A.K. Dahr, and M. Goodman Labdane derivatives and flavones from Gutierrezia dracunculoides Phytochemistry 20 1981 105 107
    • (1981) Phytochemistry , vol.20 , pp. 105-107
    • Bohlmann, F.1    Grenz, M.2    Dahr, A.K.3    Goodman, M.4
  • 27
    • 49649146804 scopus 로고
    • Triterpenoid and steroid constituents of Aster baccharoides
    • W.H. Hui, W.K. Lam, and S.M. Tye Triterpenoid and steroid constituents of Aster baccharoides Phytochemistry 10 1971 903 904
    • (1971) Phytochemistry , vol.10 , pp. 903-904
    • Hui, W.H.1    Lam, W.K.2    Tye, S.M.3
  • 29
    • 0032332888 scopus 로고    scopus 로고
    • Total NMR chemical shift assignments of baccharis oxide via 2D-INADEQUATE
    • V. Nurnberg, F.Y. Fujiwara, and A.J. Marsaioli Total NMR chemical shift assignments of baccharis oxide via 2D-INADEQUATE Magn. Reson. Chem. 36 1998 766 768
    • (1998) Magn. Reson. Chem. , vol.36 , pp. 766-768
    • Nurnberg, V.1    Fujiwara, F.Y.2    Marsaioli, A.J.3
  • 30
    • 33645794320 scopus 로고
    • Gutierrezial and further diterpenes from Gutierrezia sarothrae
    • F. Bohlmann, C. Zdero, R.M. King, and H. Robinson Gutierrezial and further diterpenes from Gutierrezia sarothrae Phytochemistry 23 1984 2007 2012
    • (1984) Phytochemistry , vol.23 , pp. 2007-2012
    • Bohlmann, F.1    Zdero, C.2    King, R.M.3    Robinson, H.4
  • 31
    • 0000566909 scopus 로고
    • Friedelin and associated triterpenoids
    • R.F. Chandler, and S.N. Hooper Friedelin and associated triterpenoids Phytochemistry 18 1979 711 724
    • (1979) Phytochemistry , vol.18 , pp. 711-724
    • Chandler, R.F.1    Hooper, S.N.2
  • 33
    • 0037560988 scopus 로고    scopus 로고
    • Mutagenesis approaches to deduce structure-function relationships in terpene synthases
    • DOI 10.1039/b008338k
    • M.J.R. Segura, B.E. Jackson, and S.P.T. Matsuda Mutagenesis approaches to deduce structure-function relationships in terpene synthases Nat. Prod. Rep. 20 2003 304 317 (Pubitemid 36761614)
    • (2003) Natural Product Reports , vol.20 , Issue.3 , pp. 304-317
    • Segura, M.J.R.1    Jackson, B.E.2    Matsuda, S.P.T.3
  • 34
    • 8544273685 scopus 로고    scopus 로고
    • Insight into steroid scaffold formation from the structure of human oxidosqualene cyclase
    • DOI 10.1038/nature02993
    • R. Thoma, T. Schulz-Gasch, B. D'Arcy, J. Benz, J. Aebi, H. Dehmlow, M. Hennig, M. Stihle, and A. Ruf Insight into steroid scaffold formation from the structure of human oxidosqualene cyclase Nature 432 2004 118 122 (Pubitemid 39490838)
    • (2004) Nature , vol.432 , Issue.7013 , pp. 118-122
    • Thoma, R.1    Schulz-Gasen, T.2    D'Arcy, B.3    Benz, J.4    Aebi, J.5    Dehmlow, H.6    Hennig, M.7    Stihle, M.8    Ruf, A.9


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