메뉴 건너뛰기




Volumn 462, Issue 3, 2014, Pages 539-546

Molecular evolution of the substrate specificity of ent -kaurene synthases to adapt to gibberellin biosynthesis in land plants

Author keywords

Cyclase; Ent kaurene; Gibberellin; Phytoalexin; Selaginella moellendorffii; Substrate specificity

Indexed keywords

4 IODO 2,5 DIMETHOXYAMPHETAMINE; ENT COPALYL DIPHOSPHATE; ENT KAURENE SYNTHASE; GERANYLGERANYL PYROPHOSPHATE; GIBBERELLIN; KAURENE DERIVATIVE; PYROPHOSPHATE; UNCLASSIFIED DRUG;

EID: 84907356645     PISSN: 02646021     EISSN: 14708728     Source Type: Journal    
DOI: 10.1042/BJ20140134     Document Type: Article
Times cited : (23)

References (43)
  • 1
    • 34250785114 scopus 로고    scopus 로고
    • The function of terpene natural products in the natural world
    • Gershenzon, J. and Dudareva, N. (2007) The function of terpene natural products in the natural world. Nat. Chem. Biol. 3, 408-414.
    • (2007) Nat. Chem. Biol. , vol.3 , pp. 408-414
    • Gershenzon, J.1    Dudareva, N.2
  • 2
    • 79955574643 scopus 로고    scopus 로고
    • Convergent evolution in plant specialized metabolism
    • Pichersky, E. and Lewinsohn, E. (2011) Convergent evolution in plant specialized metabolism. Annu. Rev. Plant Biol. 62, 549-566.
    • (2011) Annu. Rev. Plant Biol. , vol.62 , pp. 549-566
    • Pichersky, E.1    Lewinsohn, E.2
  • 3
    • 34447266182 scopus 로고    scopus 로고
    • Step-by-step acquisition of the gibberellin-DELLA growth-regulatory mechanism during land-plant evolution
    • Yasumura, Y., Crumpton-Taylor, M., Fuentes, S. and Harberd, N. P. (2007) Step-by-step acquisition of the gibberellin-DELLA growth-regulatory mechanism during land-plant evolution. Curr. Biol. 17, 1225-1230.
    • (2007) Curr. Biol. , vol.17 , pp. 1225-1230
    • Yasumura, Y.1    Crumpton-Taylor, M.2    Fuentes, S.3    Harberd, N.P.4
  • 4
    • 37249049287 scopus 로고    scopus 로고
    • The GID1-mediated gibberellin perception mechanism is conserved in the lycophyte Selaginella moellendorffii but not in the bryophyte Physcomitrella patens
    • Hirano, K., Nakajima, M., Asano, K., Nishiyama, T., Sakakibara, H., Kojima, M., Katoh, E., Xiang, H., Tanahashi, T., Hasebe, M. et al. (2007) The GID1-mediated gibberellin perception mechanism is conserved in the lycophyte Selaginella moellendorffii but not in the bryophyte Physcomitrella patens. Plant Cell 19, 3058-3079.
    • (2007) Plant Cell , vol.19 , pp. 3058-3079
    • Hirano, K.1    Nakajima, M.2    Asano, K.3    Nishiyama, T.4    Sakakibara, H.5    Kojima, M.6    Katoh, E.7    Xiang, H.8    Tanahashi, T.9    Hasebe, M.10
  • 5
    • 0000502773 scopus 로고    scopus 로고
    • Diterpene biosynthesis
    • (Cane, D. E., ed.), Elsevier Science, Amsterdam
    • MacMillan, J. and Beale, M. H. (1999) Diterpene biosynthesis. In Comprehensive Natural Products Chemistry, vol. 2 (Cane, D. E., ed.), pp. 217-243, Elsevier Science, Amsterdam.
    • (1999) Comprehensive Natural Products Chemistry , vol.2 , pp. 217-243
    • Macmillan, J.1    Beale, M.H.2
  • 6
    • 33750505476 scopus 로고    scopus 로고
    • Identification and functional analysis of bifunctional ent -kaurene synthase from the moss Physcomitrella patens
    • Hayashi, K., Kawaide, H., Notomi, M., Sakigi, Y., Matsuo, A. and Nozaki, H. (2006) Identification and functional analysis of bifunctional ent -kaurene synthase from the moss Physcomitrella patens. FEBS Lett. 580, 6175-6181.
    • (2006) FEBS Lett. , vol.580 , pp. 6175-6181
    • Hayashi, K.1    Kawaide, H.2    Notomi, M.3    Sakigi, Y.4    Matsuo, A.5    Nozaki, H.6
  • 7
    • 78650444156 scopus 로고    scopus 로고
    • Identification of the single amino acid involved in quenching the ent -kauranyl cation by a water molecule in ent -kaurene synthase of Physcomitrella patens
    • Kawaide, H., Hayashi, K., Kawanabe, R., Sakigi, Y., Matsuo, A., Natsume, M. and Nozaki, H. (2011) Identification of the single amino acid involved in quenching the ent -kauranyl cation by a water molecule in ent -kaurene synthase of Physcomitrella patens. FEBS J. 278, 123-133.
    • (2011) FEBS J. , vol.278 , pp. 123-133
    • Kawaide, H.1    Hayashi, K.2    Kawanabe, R.3    Sakigi, Y.4    Matsuo, A.5    Natsume, M.6    Nozaki, H.7
  • 8
    • 0027932244 scopus 로고
    • Cloning of casbene synthase cDNA: Evidence for conserved structural features among terpenoid cyclases in plants
    • Mau, C. J. D. and West, C. A. (1994) Cloning of casbene synthase cDNA: evidence for conserved structural features among terpenoid cyclases in plants. Proc. Natl. Acad. Sci. U.S.A. 91, 8497-8501.
    • (1994) Proc. Natl. Acad. Sci. U.S.A. , vol.91 , pp. 8497-8501
    • Mau, C.J.D.1    West, C.A.2
  • 9
    • 0029087870 scopus 로고
    • Purification and characterization of taxa-4(5) 11(12)-diene synthase from pacific yew (Taxas brevifolia ) that catalyzes the first committed step of taxol biosynthesis
    • Hezari, M., Lewis, N. G. and Croteau, R. (1995) Purification and characterization of taxa-4(5),11(12)-diene synthase from pacific yew (Taxas brevifolia ) that catalyzes the first committed step of taxol biosynthesis. Arch. Biochem. Biophys. 322, 437-444.
    • (1995) Arch. Biochem. Biophys , vol.322 , pp. 437-444
    • Hezari, M.1    Lewis, N.G.2    Croteau, R.3
  • 10
    • 0029873176 scopus 로고    scopus 로고
    • A cDNA clone for taxadiene synthase, the diterpene cyclase that catalyzes the committed step of taxol biosynthesis
    • Wildung, M. R. and Croteau, R. (1996) A cDNA clone for taxadiene synthase, the diterpene cyclase that catalyzes the committed step of taxol biosynthesis. J. Biol. Chem. 271, 9201-9204.
    • (1996) J. Biol. Chem. , vol.271 , pp. 9201-9204
    • Wildung, M.R.1    Croteau, R.2
  • 11
    • 0000828106 scopus 로고    scopus 로고
    • Abietadiene synthase from grand fir (Abies grandis). CDNA isolation, characterization, and bacterial expression of a bifunctional diterpene cyclase involved in resin acid biosynthesis
    • Vogel, B. S., Wildung, M. R., Vogel, G. and Croteau, R. (1996) Abietadiene synthase from grand fir (Abies grandis). cDNA isolation, characterization, and bacterial expression of a bifunctional diterpene cyclase involved in resin acid biosynthesis. J. Biol. Chem. 271, 23262-23268.
    • (1996) J. Biol. Chem. , vol.271 , pp. 23262-23268
    • Vogel, B.S.1    Wildung, M.R.2    Vogel, G.3    Croteau, R.4
  • 12
    • 4444324207 scopus 로고    scopus 로고
    • Functional characterization of nine Norway spruce TPS genes and evolution of gymnosperm terpene synthases of the TPS-d subfamily
    • Martin, D. M., Fäldt, J. and Bohlmann, J. (2004) Functional characterization of nine Norway spruce TPS genes and evolution of gymnosperm terpene synthases of the TPS-d subfamily. Plant Physiol. 135, 1908-1927.
    • (2004) Plant Physiol , vol.135 , pp. 1908-1927
    • Martin, D.M.1    Fäldt, J.2    Bohlmann, J.3
  • 13
    • 79952353192 scopus 로고    scopus 로고
    • Transcriptome mining, functional characterization, and phylogeny of a large terpene synthase gene family in spruce (Picea spp.)
    • Keeling, C. I., Weisshaar, S., Ralph, S. G., Jancsik, S., Hamberger, B., Dullat, H. K. and Bohlmann, J. (2011) Transcriptome mining, functional characterization, and phylogeny of a large terpene synthase gene family in spruce (Picea spp.). BMC Plant Biol. 11, 43.
    • (2011) BMC Plant Biol. , vol.11 , pp. 43
    • Keeling, C.I.1    Weisshaar, S.2    Ralph, S.G.3    Jancsik, S.4    Hamberger, B.5    Dullat, H.K.6    Bohlmann, J.7
  • 15
    • 80052157636 scopus 로고    scopus 로고
    • A novel labda-7,13E -dien-15-olproducing bifunctional diterpene synthase from Selaginella moellendorffii
    • Mafu, S., Hillwig, M. L. and Peters, R. J. (2011) A novel labda-7,13E -dien-15-olproducing bifunctional diterpene synthase from Selaginella moellendorffii. ChemBioChem 12, 1984-1987.
    • (2011) ChemBioChem , vol.12 , pp. 1984-1987
    • Mafu, S.1    Hillwig, M.L.2    Peters, R.J.3
  • 16
    • 83355166952 scopus 로고    scopus 로고
    • Enzymatic 13C labeling and multidimensional NMR analysis of miltiradiene synthesized by bifunctional diterpene cyclase in Selaginella moellendorffii
    • Sugai, Y., Ueno, Y., Hayashi, K., Oogami, S., Toyomasu, T., Matsumoto, S., Natsume, M., Nozaki, H. and Kawaide, H. (2011) Enzymatic 13C labeling and multidimensional NMR analysis of miltiradiene synthesized by bifunctional diterpene cyclase in Selaginella moellendorffii. J. Biol. Chem. 286, 42840-42847.
    • (2011) J. Biol. Chem. , vol.286 , pp. 42840-42847
    • Sugai, Y.1    Ueno, Y.2    Hayashi, K.3    Oogami, S.4    Toyomasu, T.5    Matsumoto, S.6    Natsume, M.7    Nozaki, H.8    Kawaide, H.9
  • 18
    • 70749152711 scopus 로고    scopus 로고
    • A functional genomics approach to tanshinone biosynthesis provides stereochemical Insights
    • Gao, W., Hillwig, M. L., Huang, L., Cui, G., Wang, X., Kong, J., Yang, B. and Peters, R. J. (2009) A functional genomics approach to tanshinone biosynthesis provides stereochemical Insights. Org. Lett. 11, 5170-5173.
    • (2009) Org. Lett. , vol.11 , pp. 5170-5173
    • Gao, W.1    Hillwig, M.L.2    Huang, L.3    Cui, G.4    Wang, X.5    Kong, J.6    Yang, B.7    Peters, R.J.8
  • 19
    • 0028520249 scopus 로고
    • The arabidopsis GA1 locus encodes the cyclase ent -kaurene synthetase A of gibberellin biosynthesis
    • Sun, T. and Kamiya, Y. (1994) The arabidopsis GA1 locus encodes the cyclase ent -kaurene synthetase A of gibberellin biosynthesis. Plant Cell 6, 1509-1518.
    • (1994) Plant Cell , vol.6 , pp. 1509-1518
    • Sun, T.1    Kamiya, Y.2
  • 20
    • 4644292611 scopus 로고    scopus 로고
    • Biological functions of ent- and syn-copalyl diphosphate synthases in rice: Key enzymes for the branch point of gibberellin and phytoalexin biosynthesis
    • Otomo, K., Kenmoku, H., Oikawa, H., König, W. A., Toshima, H., Mitsuhashi, W., Yamane, H., Sassa, T. and Toyomasu, T. (2004) Biological functions of ent- and syn-copalyl diphosphate synthases in rice: key enzymes for the branch point of gibberellin and phytoalexin biosynthesis. Plant J. 39, 886-893.
    • (2004) Plant J. , vol.39 , pp. 886-893
    • Otomo, K.1    Kenmoku, H.2    Oikawa, H.3    König, W.A.4    Toshima, H.5    Mitsuhashi, W.6    Yamane, H.7    Sassa, T.8    Toyomasu, T.9
  • 22
    • 51749113162 scopus 로고    scopus 로고
    • Germination of photoblastic lettuce seeds is regulated via the control of endogenous physiologically active gibberellin content, rather than of gibberellin responsiveness
    • Sawada, Y., Katsumata, K., Kitamura, J., Kawaide, H., Nakajima, M., Asami, T., Nakaminami, K., Kurahashi, T., Mitsuhashi, W., Inoue, Y. and Toyomasu, T. (2008) Germination of photoblastic lettuce seeds is regulated via the control of endogenous physiologically active gibberellin content, rather than of gibberellin responsiveness. J. Exp. Bot. 59, 3383-3393.
    • (2008) J. Exp. Bot. , vol.59 , pp. 3383-3393
    • Sawada, Y.1    Katsumata, K.2    Kitamura, J.3    Kawaide, H.4    Nakajima, M.5    Asami, T.6    Nakaminami, K.7    Kurahashi, T.8    Mitsuhashi, W.9    Inoue, Y.10    Toyomasu, T.11
  • 24
    • 0015240447 scopus 로고
    • Purification and properties of kaurene synthetase from Fusarium moniziforme
    • Fall, R. R. and West, C. A. (1971) Purification and properties of kaurene synthetase from Fusarium moniziforme. J. Biol. Chem. 246, 6913-6928.
    • (1971) J. Biol. Chem. , vol.246 , pp. 6913-6928
    • Fall, R.R.1    West, C.A.2
  • 26
    • 79953251042 scopus 로고    scopus 로고
    • The family of terpene synthases in plants: A mid-size family of genes for specialized metabolism that is highly diversified throughout the kingdom
    • Chen, F., Tholl, D., Bohlmann, J. and Pichersky, E. (2011) The family of terpene synthases in plants: a mid-size family of genes for specialized metabolism that is highly diversified throughout the kingdom. Plant J. 66, 212-229.
    • (2011) Plant J. , vol.66 , pp. 212-229
    • Chen, F.1    Tholl, D.2    Bohlmann, J.3    Pichersky, E.4
  • 29
    • 84855950170 scopus 로고    scopus 로고
    • Mutational analysis of white spruce (Picea glauca ) ent -kaurene synthase (PgKS) reveals common and distinct mechanisms of conifer diterpene synthases of general and specialized metabolism
    • Zerbe, P., Chiang, A. and Bohlmann, J. (2012) Mutational analysis of white spruce (Picea glauca ) ent -kaurene synthase (PgKS) reveals common and distinct mechanisms of conifer diterpene synthases of general and specialized metabolism. Phytochemistry 74, 30-39.
    • (2012) Phytochemistry , vol.74 , pp. 30-39
    • Zerbe, P.1    Chiang, A.2    Bohlmann, J.3
  • 31
    • 82555196593 scopus 로고    scopus 로고
    • The gibberellin perception system evolved to regulate a pre-existing GAMYB-mediated system during land plant evolution
    • Aya, K., Hiwatashi, Y., Kojima, M., Sakakibara, H., Ueguchi-Tanaka, M., Hasebe, M. and Matsuoka, M. (2011) The gibberellin perception system evolved to regulate a pre-existing GAMYB-mediated system during land plant evolution. Nat. Commun. 2, 544.
    • (2011) Nat. Commun. , pp. 544
    • Aya, K.1    Hiwatashi, Y.2    Kojima, M.3    Sakakibara, H.4    Ueguchi-Tanaka, M.5    Hasebe, M.6    Matsuoka, M.7
  • 32
    • 0032253618 scopus 로고    scopus 로고
    • The first step of gibberellin biosynthesis in pumpkin is catalyzed by at least two copalyl diphosphate synthases encoded by differentially regulated genes
    • Smith, M. W., Yamaguchi, S., Ait-Ali, T. and Kamiya, Y. (1998) The first step of gibberellin biosynthesis in pumpkin is catalyzed by at least two copalyl diphosphate synthases encoded by differentially regulated genes. Plant Physiol. 118, 1411-1419.
    • (1998) Plant Physiol , vol.118 , pp. 1411-1419
    • Smith, M.W.1    Yamaguchi, S.2    Ait-Ali, T.3    Kamiya, Y.4
  • 33
    • 0037782414 scopus 로고    scopus 로고
    • Overexpression of AtCPS and AtKS in Arabidopsis confers increased ent -kaurene production but no increase in bioactive gibberellins
    • Fleet, C. M., Yamaguchi, S., Hanada, A., Kawaide, H., David, C. J., Kamiya, Y. and Sun, T. (2003) Overexpression of AtCPS and AtKS in Arabidopsis confers increased ent -kaurene production but no increase in bioactive gibberellins. Plant Physiol. 132, 830-839.
    • (2003) Plant Physiol , vol.132 , pp. 830-839
    • Fleet, C.M.1    Yamaguchi, S.2    Hanada, A.3    Kawaide, H.4    David, C.J.5    Kamiya, Y.6    Sun, T.7
  • 34
    • 0034723356 scopus 로고    scopus 로고
    • Functional analysis of the two interacting cyclase domains in ent -kaurene synthase from the fungus Phaeosphaeria sp. L487 and a comparison with cyclases from higher plants
    • Kawaide, H., Sassa, T. and Kamiya, Y. (2000) Functional analysis of the two interacting cyclase domains in ent -kaurene synthase from the fungus Phaeosphaeria sp. L487 and a comparison with cyclases from higher plants. J. Biol. Chem. 275, 2276-2280.
    • (2000) J. Biol. Chem. , vol.275 , pp. 2276-2280
    • Kawaide, H.1    Sassa, T.2    Kamiya, Y.3
  • 35
    • 79954546857 scopus 로고    scopus 로고
    • Evident and latent plasticity across the rice diterpene synthase family with potential implications for the evolution of diterpenoid metabolism in the cereals
    • Morrone, D., Hillwig, M. L., Mead, M. E., Lowry, L., Fulton, D. B. and Peters, R. J. (2011) Evident and latent plasticity across the rice diterpene synthase family with potential implications for the evolution of diterpenoid metabolism in the cereals. Biochem. J. 435, 589-595.
    • (2011) Biochem. J. , vol.435 , pp. 589-595
    • Morrone, D.1    Hillwig, M.L.2    Mead, M.E.3    Lowry, L.4    Fulton, D.B.5    Peters, R.J.6
  • 36
    • 84868122432 scopus 로고    scopus 로고
    • Functional characterization of wheat ent -kaurene(-like) synthases indicates continuing evolution of labdane-related diterpenoid metabolism in the cereals
    • Zhou, K., Xu, M., Tiernan, M., Xie, Q., Toyomasu, T., Sugawara, C., Oku, M., Usui, M., Mitsuhashi, W., Chono, M., Chandler, P. M. and Peters, R. J. (2012) Functional characterization of wheat ent -kaurene(-like) synthases indicates continuing evolution of labdane-related diterpenoid metabolism in the cereals. Phytochemistry 84, 47-55.
    • (2012) Phytochemistry , vol.84 , pp. 47-55
    • Zhou, K.1    Xu, M.2    Tiernan, M.3    Xie, Q.4    Toyomasu, T.5    Sugawara, C.6    Oku, M.7    Usui, M.8    Mitsuhashi, W.9    Chono, M.10    Chandler, P.M.11    Peters, R.J.12
  • 37
    • 33749512596 scopus 로고    scopus 로고
    • Uncovering the complex metabolic network underlying diterpenoid phytoalexin biosynthesis in rice and other cereal crop plants
    • Peters, R. J. (2006) Uncovering the complex metabolic network underlying diterpenoid phytoalexin biosynthesis in rice and other cereal crop plants. Phytochemistry 67, 2307-2317.
    • (2006) Phytochemistry , vol.67 , pp. 2307-2317
    • Peters, R.J.1
  • 38
    • 45849132076 scopus 로고    scopus 로고
    • Recent advances regarding diterpene cyclase genes in higher plants and fungi
    • Toyomasu, T. (2008) Recent advances regarding diterpene cyclase genes in higher plants and fungi. Biosci. Biotechnol. Biochem. 72, 1168-1175.
    • (2008) Biosci. Biotechnol. Biochem. , vol.72 , pp. 1168-1175
    • Toyomasu, T.1
  • 39
    • 79960807863 scopus 로고    scopus 로고
    • The biosynthesis of isoprenoids and the mechanism regulating it in plants
    • Okada, K. (2011) The biosynthesis of isoprenoids and the mechanism regulating it in plants. Biosci. Biotechnol. Biochem. 75, 1219-1225.
    • (2011) Biosci. Biotechnol. Biochem. , vol.75 , pp. 1219-1225
    • Okada, K.1
  • 40
    • 84880175153 scopus 로고    scopus 로고
    • Biosynthesis of phytoalexins and regulatory mechanisms of it in rice
    • Yamane, H. (2013) Biosynthesis of phytoalexins and regulatory mechanisms of it in rice. Biosci. Biotechnol. Biochem. 77, 1141-1148.
    • (2013) Biosci. Biotechnol. Biochem. , vol.77 , pp. 1141-1148
    • Yamane, H.1
  • 41
    • 34250688380 scopus 로고    scopus 로고
    • Following evolution's lead to a single residue switch for diterpene synthase product outcome
    • Xu, M., Wilderman, P. R. and Peters, R. J. (2007) Following evolution's lead to a single residue switch for diterpene synthase product outcome. Proc. Natl. Acad. Sci. U.S.A. 104, 7397-7401.
    • (2007) Proc. Natl. Acad. Sci. U.S.A. , vol.104 , pp. 7397-7401
    • Xu, M.1    Wilderman, P.R.2    Peters, R.J.3
  • 42
    • 33750505476 scopus 로고    scopus 로고
    • Identification and functional analysis of bifunctional ent -kaurene synthase from the moss Physcomitrella patens
    • Hayashi, K., Kawaide, H., Notomi, M., Sakigi, Y., Matsuo, A. and Nozaki, H. (2006) Identification and functional analysis of bifunctional ent -kaurene synthase from the moss Physcomitrella patens. FEBS Lett. 580, 6175-6181.
    • (2006) FEBS Lett , vol.580 , pp. 6175-6181
    • Hayashi, K.1    Kawaide, H.2    Notomi, M.3    Sakigi, Y.4    Matsuo, A.5    Nozaki, H.6
  • 43
    • 78650444156 scopus 로고    scopus 로고
    • Identification of the single amino acid involved in quenching the ent -kauranyl cation by a water molecule in ent -kaurene synthase of Physcomitrella patens
    • Kawaide, H., Hayashi, K., Kawanabe, R., Sakigi, Y., Matsuo, A., Natsume, M. and Nozaki, H. (2011) Identification of the single amino acid involved in quenching the ent -kauranyl cation by a water molecule in ent -kaurene synthase of Physcomitrella patens. FEBS J. 278, 123-133.
    • (2011) FEBS J. , vol.278 , pp. 123-133
    • Kawaide, H.1    Hayashi, K.2    Kawanabe, R.3    Sakigi, Y.4    Matsuo, A.5    Natsume, M.6    Nozaki, H.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.