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Volumn 154, Issue 1, 2010, Pages 301-310

A copal-8-ol diphosphate synthase from the angiosperm Cistus creticus subsp. creticus is a putative key enzyme for the formation of pharmacologically active, oxygen-containing labdane-type diterpenes

Author keywords

[No Author keywords available]

Indexed keywords

BURSERA FAGAROIDES; CISTUS; CISTUS CRETICUS; ESCHERICHIA COLI; MAGNOLIOPHYTA;

EID: 77956656821     PISSN: 00320889     EISSN: 15322548     Source Type: Journal    
DOI: 10.1104/pp.110.159566     Document Type: Article
Times cited : (68)

References (43)
  • 2
    • 0032714739 scopus 로고    scopus 로고
    • Analysis of labdane-type diterpenes from Cistus creticus (subsp. creticus and subsp. eriocephalus) by GC and GC-MS
    • Anastasaki T, Demetzos C, Perdetzoglou D, Gazouli M, Loukis A, Harvala C (1999) Analysis of labdane-type diterpenes from Cistus creticus (subsp. creticus and subsp. eriocephalus) by GC and GC-MS. Planta Med 65: 735-739
    • (1999) Planta Med , vol.65 , pp. 735-739
    • Anastasaki, T.1    Demetzos, C.2    Perdetzoglou, D.3    Gazouli, M.4    Loukis, A.5    Harvala, C.6
  • 3
    • 32544449338 scopus 로고    scopus 로고
    • Antimicrobial activities of the leaf extracts of two Moroccan Cistus L. species
    • Bouamama H, Noel T, Villard J, Benharref A, JanaM(2006) Antimicrobial activities of the leaf extracts of two Moroccan Cistus L. species. J Ethnopharmacol 104: 104-107
    • (2006) J Ethnopharmacol , vol.104 , pp. 104-107
    • Bouamama, H.1    Noel, T.2    Villard, J.3    Benharref, A.4    Jana, M.5
  • 6
    • 19044400124 scopus 로고    scopus 로고
    • Labdanes of natural origin: Biological activities (1981- 2004)
    • Chinou I (2005) Labdanes of natural origin: biological activities (1981- 2004). Curr Med Chem 12: 1295-1317
    • (2005) Curr Med Chem , vol.12 , pp. 1295-1317
    • Chinou, I.1
  • 9
    • 0027937907 scopus 로고
    • Natural metabolites of ent-13-epi-manoyl oxide and other cytotoxic diterpenes from the resin "LADANO" of Cistus creticus
    • Demetzos C, Mitaku S, Couladis M, Harvala C, Kokkinopoulos D (1994) Natural metabolites of ent-13-epi-manoyl oxide and other cytotoxic diterpenes from the resin "LADANO" of Cistus creticus. PlantaMed 60: 590-591
    • (1994) PlantaMed , vol.60 , pp. 590-591
    • Demetzos, C.1    Mitaku, S.2    Couladis, M.3    Harvala, C.4    Kokkinopoulos, D.5
  • 10
    • 0035040356 scopus 로고    scopus 로고
    • Labdane type diterpenes down-regulate the expression of c-Myc protein, but not of Bcl-2, in human leukemia T-cells undergoing apoptosis
    • Dimas K, Demetzos C, Vaos V, Ioannidis P, Trangas T (2001) Labdane type diterpenes down-regulate the expression of c-Myc protein, but not of Bcl-2, in human leukemia T-cells undergoing apoptosis. Leuk Res 25: 449-454
    • (2001) Leuk Res , vol.25 , pp. 449-454
    • Dimas, K.1    Demetzos, C.2    Vaos, V.3    Ioannidis, P.4    Trangas, T.5
  • 11
    • 33645417223 scopus 로고    scopus 로고
    • Labd-14-ene-8,13-diol (sclareol) induces cell cycle arrest and apoptosis in human breast cancer cells and enhances the activity of anticancer drugs
    • Dimas K, Papadaki M, Tsimplouli C, Hatziantoniou S, Alevizopoulos K, Pantazis P, Demetzos C (2006) Labd-14-ene-8,13-diol (sclareol) induces cell cycle arrest and apoptosis in human breast cancer cells and enhances the activity of anticancer drugs. Biomed Pharmacother 60: 127-133
    • (2006) Biomed Pharmacother , vol.60 , pp. 127-133
    • Dimas, K.1    Papadaki, M.2    Tsimplouli, C.3    Hatziantoniou, S.4    Alevizopoulos, K.5    Pantazis, P.6    Demetzos, C.7
  • 12
    • 0037877924 scopus 로고    scopus 로고
    • (E)-Beta-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
    • Dudareva N, Martin D, Kish CM, Kolosova N, Gorenstein N, Faldt J, Miller B, Bohlmann J (2003) (E)-Beta-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: 1227-1241
    • (2003) Plant Cell , vol.15 , pp. 1227-1241
    • Dudareva, N.1    Martin, D.2    Kish, C.M.3    Kolosova, N.4    Gorenstein, N.5    Faldt, J.6    Miller, B.7    Bohlmann, J.8
  • 13
    • 0034697980 scopus 로고    scopus 로고
    • Predicting subcellular localization of proteins based on their N-terminal amino acid sequence
    • Emanuelsson O, Nielsen H, Brunak S, von Heijne G (2000) Predicting subcellular localization of proteins based on their N-terminal amino acid sequence. J Mol Biol 300: 1005-1016
    • (2000) J Mol Biol , vol.300 , pp. 1005-1016
    • Emanuelsson, O.1    Nielsen, H.2    Brunak, S.3    von Heijne, G.4
  • 15
    • 74249109488 scopus 로고    scopus 로고
    • Differential accumulation of volatile terpene and terpene synthase mRNAs during lavender (Lavandula angustifolia and L. x intermedia) inflorescence development
    • Guitton Y, Nicole F, Moja S, Valot N, Legrand S, Jullien F, Legendre L (2010) Differential accumulation of volatile terpene and terpene synthase mRNAs during lavender (Lavandula angustifolia and L. x intermedia) inflorescence development. Physiol Plant 138: 150-163
    • (2010) Physiol Plant , vol.138 , pp. 150-163
    • Guitton, Y.1    Nicole, F.2    Moja, S.3    Valot, N.4    Legrand, S.5    Jullien, F.6    Legendre, L.7
  • 16
    • 0028279649 scopus 로고
    • Biosynthesis of the diterpene cisabienol in cell-free extracts of tobacco trichomes
    • Guo Z, Severson RF, Wagner GJ (1994) Biosynthesis of the diterpene cisabienol in cell-free extracts of tobacco trichomes. Arch Biochem Biophys 103: 103-108
    • (1994) Arch Biochem Biophys , vol.103 , pp. 103-108
    • Guo, Z.1    Severson, R.F.2    Wagner, G.J.3
  • 17
    • 0029197180 scopus 로고
    • Biosynthesis of labdenediol and sclareol in cellfree extracts from trichomes of Nicotiana glutinosa
    • Guo Z, Wagner G (1995) Biosynthesis of labdenediol and sclareol in cellfree extracts from trichomes of Nicotiana glutinosa. Planta 197: 627-632
    • (1995) Planta , vol.197 , pp. 627-632
    • Guo, Z.1    Wagner, G.2
  • 18
    • 34248631420 scopus 로고    scopus 로고
    • Cytochrome P450 mono-oxygenases in conifer genomes: Discovery of members of the terpenoid oxygenase superfamily in spruce and pine
    • Hamberger B, Bohlmann J (2006) Cytochrome P450 mono-oxygenases in conifer genomes: discovery of members of the terpenoid oxygenase superfamily in spruce and pine. Biochem Soc Trans 34: 1209-1214
    • (2006) Biochem Soc Trans , vol.34 , pp. 1209-1214
    • Hamberger, B.1    Bohlmann, J.2
  • 19
    • 27744591084 scopus 로고    scopus 로고
    • Cytotoxic and antitumor activity of liposome-incorporated sclareol against cancer cell lines and human colon cancer xenografts
    • Hatziantoniou S, Dimas K, Georgopoulos A, Sotiriadou N, Demetzos C (2006) Cytotoxic and antitumor activity of liposome-incorporated sclareol against cancer cell lines and human colon cancer xenografts. Pharmacol Res 53: 80-87
    • (2006) Pharmacol Res , vol.53 , pp. 80-87
    • Hatziantoniou, S.1    Dimas, K.2    Georgopoulos, A.3    Sotiriadou, N.4    Demetzos, C.5
  • 20
    • 0542420973 scopus 로고    scopus 로고
    • Ovipositional response of tobacco budworm moths (Lepidoptera: Noctuidae) to cuticular labdanes and sucrose esters from the green leaves of Nicotiana glutinosa L. (Solanaceae)
    • JacksonM, Severson RF, Sisson VA, Stephenson MG (1999) Ovipositional response of tobacco budworm moths (Lepidoptera: Noctuidae) to cuticular labdanes and sucrose esters from the green leaves of Nicotiana glutinosa L. (Solanaceae). J Chem Ecol 17: 2489-2506
    • (1999) J Chem Ecol , vol.17 , pp. 2489-2506
    • Jackson, M.1    Severson, R.F.2    Sisson, V.A.3    Stephenson, M.G.4
  • 22
    • 77949506768 scopus 로고    scopus 로고
    • Identification and functional characterization of monofunctional entcopalyl diphosphate and ent-kaurene synthases in white spruce reveal different patterns for diterpene synthase evolution for primary and secondary metabolism in gymnosperms
    • Keeling CI, Dullat HK, Yuen M, Ralph SG, Jancsik S, Bohlmann J (2010) Identification and functional characterization of monofunctional entcopalyl diphosphate and ent-kaurene synthases in white spruce reveal different patterns for diterpene synthase evolution for primary and secondary metabolism in gymnosperms. Plant Physiol 152: 1197-1208
    • (2010) Plant Physiol , vol.152 , pp. 1197-1208
    • Keeling, C.I.1    Dullat, H.K.2    Yuen, M.3    Ralph, S.G.4    Jancsik, S.5    Bohlmann, J.6
  • 23
    • 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 DM, Faldt J, 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    Faldt, J.2    Bohlmann, J.3
  • 24
    • 33745060142 scopus 로고    scopus 로고
    • Design and development of liposomes incorporating a bioactive labdane-type diterpene: In vitro growth inhibiting and cytotoxic activity against human cancer cell lines
    • Matsingou C, Dimas K, Demetzos C (2006) Design and development of liposomes incorporating a bioactive labdane-type diterpene: in vitro growth inhibiting and cytotoxic activity against human cancer cell lines. Biomed Pharmacother 60: 191-199
    • (2006) Biomed Pharmacother , vol.60 , pp. 191-199
    • Matsingou, C.1    Dimas, K.2    Demetzos, C.3
  • 25
    • 27644434682 scopus 로고    scopus 로고
    • Labdane-type diterpenes: Thermal effects on phospholipid bilayers, incorporation into liposomes and biological activity
    • Matsingou C, Hatziantoniou S, Georgopoulos A, Dimas K, Terzis A, Demetzos C (2005) Labdane-type diterpenes: thermal effects on phospholipid bilayers, incorporation into liposomes and biological activity. Chem Phys Lipids 138: 1-11
    • (2005) Chem Phys Lipids , vol.138 , pp. 1-11
    • Matsingou, C.1    Hatziantoniou, S.2    Georgopoulos, A.3    Dimas, K.4    Terzis, A.5    Demetzos, C.6
  • 26
    • 0033759392 scopus 로고    scopus 로고
    • Developmental regulation of monoterpene biosynthesis in the glandular trichomes of peppermint
    • McConkey ME, Gershenzon J, Croteau RB (2000) Developmental regulation of monoterpene biosynthesis in the glandular trichomes of peppermint. Plant Physiol 122: 215-224
    • (2000) Plant Physiol , vol.122 , pp. 215-224
    • McConkey, M.E.1    Gershenzon, J.2    Croteau, R.B.3
  • 28
    • 0030614959 scopus 로고    scopus 로고
    • Identification of prokaryotic and eukaryotic signal peptides and prediction of their cleavage sites
    • Nielsen H, Engelbrecht J, Brunak S, von Heijne G (1997) Identification of prokaryotic and eukaryotic signal peptides and prediction of their cleavage sites. Protein Eng 10: 1-6
    • (1997) Protein Eng , vol.10 , pp. 1-6
    • Nielsen, H.1    Engelbrecht, J.2    Brunak, S.3    von Heijne, G.4
  • 30
    • 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, KonigWA, Toshima H,MitsuhashiW, Yamane H, Sassa T, Toyomasu T (2004b) 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    Konig, W.A.4    Toshima, H.5    Mitsuhashi, W.6    Yamane, H.7    Sassa, T.8    Toyomasu, T.9
  • 31
    • 1842736492 scopus 로고    scopus 로고
    • Isolation of high-quality nucleic acids fromCistus creticus ssp. creticus and other medicinal plants
    • Pateraki I, Kanellis AK (2004) Isolation of high-quality nucleic acids fromCistus creticus ssp. creticus and other medicinal plants. Anal Biochem 328: 90-92
    • (2004) Anal Biochem , vol.328 , pp. 90-92
    • Pateraki, I.1    Kanellis, A.K.2
  • 32
    • 16644374383 scopus 로고    scopus 로고
    • Rice contains two disparate ent-copalyl diphosphate synthases with distinct metabolic functions
    • Prisic S, Xu M, Wilderman PR, Peters RJ (2004) Rice contains two disparate ent-copalyl diphosphate synthases with distinct metabolic functions. Plant Physiol 136: 4228-4236
    • (2004) Plant Physiol , vol.136 , pp. 4228-4236
    • Prisic, S.1    Xu, M.2    Wilderman, P.R.3    Peters, R.J.4
  • 33
    • 0034624597 scopus 로고    scopus 로고
    • Stereochemistry of the cyclization-rearrangement of (+)-copalyl diphosphate to (2)-abietadiene catalyzed by recombinant abietadiene synthase from Abies grandis
    • Ravn MM, Coates RM, Flory JE, Peters RJ, Croteau R (2000) Stereochemistry of the cyclization-rearrangement of (+)-copalyl diphosphate to (2)-abietadiene catalyzed by recombinant abietadiene synthase from Abies grandis. Org Lett 2: 573-576
    • (2000) Org Lett , vol.2 , pp. 573-576
    • Ravn, M.M.1    Coates, R.M.2    Flory, J.E.3    Peters, R.J.4    Croteau, R.5
  • 34
    • 20344404474 scopus 로고    scopus 로고
    • Loblolly pine abietadienol/abietadienal oxidase PtAO (CYP720B1) is a multifunctional, multisubstrate cytochrome P450monooxygenase
    • Ro DK, Arimura G, Lau SY, Piers E, Bohlmann J (2005) Loblolly pine abietadienol/abietadienal oxidase PtAO (CYP720B1) is a multifunctional, multisubstrate cytochrome P450monooxygenase. Proc Natl Acad Sci USA 102: 8060-8065
    • (2005) Proc Natl Acad Sci USA , vol.102 , pp. 8060-8065
    • Ro, D.K.1    Arimura, G.2    Lau, S.Y.3    Piers, E.4    Bohlmann, J.5
  • 35
    • 33646686232 scopus 로고    scopus 로고
    • Diterpene resin acid biosynthesis in loblolly pine (Pinus taeda): Functional characterization of abietadiene/levopimaradiene synthase (PtTPS-LAS) cDNA and subcellular targeting of PtTPS-LAS and abietadienol/abietadienal oxidase (PtAO, CYP720B1)
    • Ro DK, Bohlmann J (2006) Diterpene resin acid biosynthesis in loblolly pine (Pinus taeda): functional characterization of abietadiene/levopimaradiene synthase (PtTPS-LAS) cDNA and subcellular targeting of PtTPS-LAS and abietadienol/abietadienal oxidase (PtAO, CYP720B1). Phytochemistry 67: 1572-1578
    • (2006) Phytochemistry , vol.67 , pp. 1572-1578
    • Ro, D.K.1    Bohlmann, J.2
  • 37
    • 0035881523 scopus 로고    scopus 로고
    • Cloning and characterization of Ginkgo biloba levopimaradiene synthase which catalyzes the first committed step in ginkgolide biosynthesis
    • Schepmann HG, Pang J, Matsuda SP (2001) Cloning and characterization of Ginkgo biloba levopimaradiene synthase which catalyzes the first committed step in ginkgolide biosynthesis. Arch Biochem Biophys 392: 263-269
    • (2001) Arch Biochem Biophys , vol.392 , pp. 263-269
    • Schepmann, H.G.1    Pang, J.2    Matsuda, S.P.3
  • 38
    • 0042322332 scopus 로고    scopus 로고
    • Activation and inhibition of rubber transferases by metal cofactors and pyrophosphate substrates
    • Scott DJ, da Costa BM, Espy SC, Keasling JD, Cornish K (2003) Activation and inhibition of rubber transferases by metal cofactors and pyrophosphate substrates. Phytochemistry 64: 123-134
    • (2003) Phytochemistry , vol.64 , pp. 123-134
    • Scott, D.J.1    da Costa, B.M.2    Espy, S.C.3    Keasling, J.D.4    Cornish, K.5
  • 39
    • 0242416568 scopus 로고    scopus 로고
    • A diterpene as an endogenous signal for the activation of defense responses to infection with tobacco mosaic virus and wounding in tobacco
    • Seo S, Seto H, Koshino H, Yoshida S, Ohashi Y (2003) A diterpene as an endogenous signal for the activation of defense responses to infection with tobacco mosaic virus and wounding in tobacco. Plant Cell 15: 863-873
    • (2003) Plant Cell , vol.15 , pp. 863-873
    • Seo, S.1    Seto, H.2    Koshino, H.3    Yoshida, S.4    Ohashi, Y.5
  • 40
    • 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
    • Stofer Vogel B, Wildung MR, Vogel G, 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
    • Stofer Vogel, B.1    Wildung, M.R.2    Vogel, G.3    Croteau, R.4
  • 41
    • 34547781750 scopus 로고    scopus 로고
    • MEGA4: Molecular Evolutionary Genetics Analysis (MEGA) software version 4.0
    • Tamura K, Dudley J, Nei M, Kumar S (2007) MEGA4: Molecular Evolutionary Genetics Analysis (MEGA) software version 4.0. Mol Biol Evol 24: 1596-1599
    • (2007) Mol Biol Evol , vol.24 , pp. 1596-1599
    • Tamura, K.1    Dudley, J.2    Nei, M.3    Kumar, S.4
  • 42
    • 4444335616 scopus 로고    scopus 로고
    • Identification of syn-pimara-7,15-diene synthase reveals functional clustering of terpene synthases involved in rice phytoalexin/allelochemical biosynthesis
    • Wilderman PR, Xu M, Jin Y, Coates RM, Peters RJ (2004) Identification of syn-pimara-7,15-diene synthase reveals functional clustering of terpene synthases involved in rice phytoalexin/allelochemical biosynthesis. Plant Physiol 135: 2098-2105
    • (2004) Plant Physiol , vol.135 , pp. 2098-2105
    • Wilderman, P.R.1    Xu, M.2    Jin, Y.3    Coates, R.M.4    Peters, R.J.5
  • 43
    • 3843081731 scopus 로고    scopus 로고
    • Functional identification of rice syn-copalyl diphosphate synthase and its role in initiating biosynthesis of diterpenoid phytoalexin/allelopathic natural products
    • Xu M, Hillwig ML, Prisic S, Coates RM, Peters RJ (2004) Functional identification of rice syn-copalyl diphosphate synthase and its role in initiating biosynthesis of diterpenoid phytoalexin/allelopathic natural products. Plant J 39: 309-318
    • (2004) Plant J , vol.39 , pp. 309-318
    • Xu, M.1    Hillwig, M.L.2    Prisic, S.3    Coates, R.M.4    Peters, R.J.5


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