메뉴 건너뛰기




Volumn 83, Issue 2, 2015, Pages 252-262

Molecular identification of tuliposide B-converting enzyme: A lactone-forming carboxylesterase from the pollen of tulip

Author keywords

lactone forming carboxylesterase; pollen; tulip; Tulipa gesneriana; tulipalin; tuliposide; tuliposide converting enzyme

Indexed keywords

ENZYMES; ESTERS; METABOLITES; POLYMERASE CHAIN REACTION;

EID: 84936750183     PISSN: 09607412     EISSN: 1365313X     Source Type: Journal    
DOI: 10.1111/tpj.12883     Document Type: Article
Times cited : (18)

References (41)
  • 1
    • 18144363888 scopus 로고    scopus 로고
    • Molecular and biochemical characterization of 2-hydroxyisoflavanone dehydratase. Involvement of carboxylesterase-like proteins in leguminous isoflavone biosynthesis
    • Akashi, T., Aoki, T., and, Ayabe, S., (2005) Molecular and biochemical characterization of 2-hydroxyisoflavanone dehydratase. Involvement of carboxylesterase-like proteins in leguminous isoflavone biosynthesis. Plant Physiol. 137, 882-891.
    • (2005) Plant Physiol. , vol.137 , pp. 882-891
    • Akashi, T.1    Aoki, T.2    Ayabe, S.3
  • 3
    • 0013597157 scopus 로고
    • Enzymic and non-enzymic liberation of tulipalin A (α-methylene butyrolactone) in extracts of tulip
    • Beijersbergen, J.C.M., and, Lemmers, C.B.G., (1972) Enzymic and non-enzymic liberation of tulipalin A (α-methylene butyrolactone) in extracts of tulip. Physiol. Plant Pathol. 2, 265-270.
    • (1972) Physiol. Plant Pathol. , vol.2 , pp. 265-270
    • Beijersbergen, J.C.M.1    Lemmers, C.B.G.2
  • 4
    • 0344057535 scopus 로고
    • A fungitoxic substance extracted from tulips and its possible role as a protectant against disease
    • Bergman, B.H.H., and, Beijersbergen, J.C.M., (1968) A fungitoxic substance extracted from tulips and its possible role as a protectant against disease. Neth. J. Plant Pathol. 74, 157-162.
    • (1968) Neth. J. Plant Pathol. , vol.74 , pp. 157-162
    • Bergman, B.H.H.1    Beijersbergen, J.C.M.2
  • 6
    • 0001835056 scopus 로고    scopus 로고
    • Pollen-pistil interactions during pollen-tube growth
    • Cheung, A.Y., (1996) Pollen-pistil interactions during pollen-tube growth. Trends Plant Sci. 1, 45-51.
    • (1996) Trends Plant Sci. , vol.1 , pp. 45-51
    • Cheung, A.Y.1
  • 7
    • 0032976703 scopus 로고    scopus 로고
    • Isolation and quantification of tuliposides and tulipalins in tulips (Tulipa) by high-performance liquid chromatography
    • Christensen, L.P., and, Kristiansen, K., (1999) Isolation and quantification of tuliposides and tulipalins in tulips (Tulipa) by high-performance liquid chromatography. Contact Dermat. 40, 300-309.
    • (1999) Contact Dermat. , vol.40 , pp. 300-309
    • Christensen, L.P.1    Kristiansen, K.2
  • 8
    • 13444263252 scopus 로고    scopus 로고
    • Structural and biochemical studies identify tobacco SABP2 as a methyl salicylate esterase and implicate it in plant innate immunity
    • Forouhar, F., Yang, Y., Kumar, D., et al. (2005) Structural and biochemical studies identify tobacco SABP2 as a methyl salicylate esterase and implicate it in plant innate immunity. Proc. Natl Acad. Sci. USA, 102, 1773-1778.
    • (2005) Proc. Natl Acad. Sci. USA , vol.102 , pp. 1773-1778
    • Forouhar, F.1    Yang, Y.2    Kumar, D.3
  • 9
    • 35248888056 scopus 로고    scopus 로고
    • Regulating biological activity in plants with carboxylesterases
    • Gershater, M.C., and, Edwards, R., (2007) Regulating biological activity in plants with carboxylesterases. Plant Sci. 173, 579-588.
    • (2007) Plant Sci. , vol.173 , pp. 579-588
    • Gershater, M.C.1    Edwards, R.2
  • 10
    • 84877857613 scopus 로고    scopus 로고
    • Smoke-derived karrikin perception by the α/β-hydrolase KAI2 from Arabidopsis
    • Guo, Y., Zheng, Z., La Clair, J.J., Chory, J., and, Noel, J.P., (2013) Smoke-derived karrikin perception by the α/β-hydrolase KAI2 from Arabidopsis. Proc. Natl Acad. Sci. USA, 110, 8284-8289.
    • (2013) Proc. Natl Acad. Sci. USA , vol.110 , pp. 8284-8289
    • Guo, Y.1    Zheng, Z.2    La Clair, J.J.3    Chory, J.4    Noel, J.P.5
  • 11
    • 84868514386 scopus 로고    scopus 로고
    • DAD2 is an α/β hydrolase likely to be involved in the perception of the plant branching hormone, strigolactone
    • Hamiaux, C., Drummond, R.S.M., Janssen, B.J., Ledger, S.E., Cooney, J.M., Newcomb, R.D., and, Snowden, K.C., (2012) DAD2 is an α/β hydrolase likely to be involved in the perception of the plant branching hormone, strigolactone. Curr. Biol. 22, 2032-2036.
    • (2012) Curr. Biol. , vol.22 , pp. 2032-2036
    • Hamiaux, C.1    Drummond, R.S.M.2    Janssen, B.J.3    Ledger, S.E.4    Cooney, J.M.5    Newcomb, R.D.6    Snowden, K.C.7
  • 12
    • 34250677996 scopus 로고    scopus 로고
    • Tapetosomes in Brassica tapetum accumulate endoplasmic reticulum-derived flavonoids and alkanes for delivery to the pollen surface
    • Hsieh, K., and, Huang, A.H.C., (2007) Tapetosomes in Brassica tapetum accumulate endoplasmic reticulum-derived flavonoids and alkanes for delivery to the pollen surface. Plant Cell, 19, 582-596.
    • (2007) Plant Cell , vol.19 , pp. 582-596
    • Hsieh, K.1    Huang, A.H.C.2
  • 13
    • 33847059230 scopus 로고    scopus 로고
    • High-resolution crystal structure of plant carboxylesterase AeCXE1, from Actinidia eriantha, and its complex with a high-affinity inhibitor paraoxon
    • Ileperuma, N.R., Marchall, S.D.G., Squire, C.J., Baker, H.M., Oakeshott, J.G., Russell, R.J., Plummer, K.M., Newcomb, R.D., and, Baker, E.N., (2007) High-resolution crystal structure of plant carboxylesterase AeCXE1, from Actinidia eriantha, and its complex with a high-affinity inhibitor paraoxon. Biochemistry, 46, 1851-1859.
    • (2007) Biochemistry , vol.46 , pp. 1851-1859
    • Ileperuma, N.R.1    Marchall, S.D.G.2    Squire, C.J.3    Baker, H.M.4    Oakeshott, J.G.5    Russell, R.J.6    Plummer, K.M.7    Newcomb, R.D.8    Baker, E.N.9
  • 14
    • 84861633609 scopus 로고    scopus 로고
    • Natural and synthetic α-methylenelactones and α-methylenelactams with anticancer potential
    • Jenecka, A., Wyrębska, A., Gach, K., Fichna, J., and, Janecki, T., (2012) Natural and synthetic α-methylenelactones and α-methylenelactams with anticancer potential. Drug Discov. Today, 17, 561-572.
    • (2012) Drug Discov. Today , vol.17 , pp. 561-572
    • Jenecka, A.1    Wyrębska, A.2    Gach, K.3    Fichna, J.4    Janecki, T.5
  • 15
    • 84879689826 scopus 로고    scopus 로고
    • New antifungal scaffold derived from a natural pharmacophore: Synthesis of α-methylene-γ-butyrolactone derivatives and their antifungal activity against Colletotrichum lagenarium
    • Jun-Tao, F., De-Long, W., Yong-Ling, W., He, Y., and, Xing, Z., (2013) New antifungal scaffold derived from a natural pharmacophore: synthesis of α-methylene-γ-butyrolactone derivatives and their antifungal activity against Colletotrichum lagenarium. Bioorg. Med. Chem. Lett. 23, 4393-4397.
    • (2013) Bioorg. Med. Chem. Lett. , vol.23 , pp. 4393-4397
    • Jun-Tao, F.1    De-Long, W.2    Yong-Ling, W.3    He, Y.4    Xing, Z.5
  • 16
    • 69949156923 scopus 로고    scopus 로고
    • Purification and characterization of a tuliposide-converting enzyme from bulbs of Tulipa gesneriana
    • Kato, Y., Shoji, K., Ubukata, M., Shigetomi, K., Sato, Y., Nakajima, N., and, Ogita, S., (2009a) Purification and characterization of a tuliposide-converting enzyme from bulbs of Tulipa gesneriana. Biosci. Biotechnol. Biochem. 73, 1895-1897.
    • (2009) Biosci. Biotechnol. Biochem. , vol.73 , pp. 1895-1897
    • Kato, Y.1    Shoji, K.2    Ubukata, M.3    Shigetomi, K.4    Sato, Y.5    Nakajima, N.6    Ogita, S.7
  • 17
    • 67649338449 scopus 로고    scopus 로고
    • A facile method for the preparation of α-methylene-γ-butyrolactones from tulip tissues by enzyme-mediated conversion
    • Kato, Y., Yoshida, H., Shoji, K., Sato, Y., Nakajima, N., and, Ogita, S., (2009b) A facile method for the preparation of α-methylene-γ-butyrolactones from tulip tissues by enzyme-mediated conversion. Tetrahedron Lett. 50, 4751-4753.
    • (2009) Tetrahedron Lett. , vol.50 , pp. 4751-4753
    • Kato, Y.1    Yoshida, H.2    Shoji, K.3    Sato, Y.4    Nakajima, N.5    Ogita, S.6
  • 18
    • 70949096336 scopus 로고    scopus 로고
    • The rice α-amylase glycoprotein is targeted from the Golgi apparatus through the secretory pathway to the plastids
    • Kitajima, A., Asatsuma, S., Okada, H., et al. (2009) The rice α-amylase glycoprotein is targeted from the Golgi apparatus through the secretory pathway to the plastids. Plant Cell, 21, 2844-2858.
    • (2009) Plant Cell , vol.21 , pp. 2844-2858
    • Kitajima, A.1    Asatsuma, S.2    Okada, H.3
  • 19
    • 84878440984 scopus 로고    scopus 로고
    • Sporopollenin biosynthetic enzymes interact and constitute a metabolon localized to the endoplasmic reticulum of tapetum cells
    • Lallemand, B., Erhardt, M., Heitz, T., and, Legrand, M., (2013) Sporopollenin biosynthetic enzymes interact and constitute a metabolon localized to the endoplasmic reticulum of tapetum cells. Plant Physiol. 162, 616-625.
    • (2013) Plant Physiol. , vol.162 , pp. 616-625
    • Lallemand, B.1    Erhardt, M.2    Heitz, T.3    Legrand, M.4
  • 20
    • 84884501069 scopus 로고    scopus 로고
    • Tapetum: Regulation and role in sporopollenin biosynthesis in Arabidopsis
    • Liu, L., and, Fan, X., (2013) Tapetum: regulation and role in sporopollenin biosynthesis in Arabidopsis. Plant Mol. Biol. 83, 165-175.
    • (2013) Plant Mol. Biol. , vol.83 , pp. 165-175
    • Liu, L.1    Fan, X.2
  • 21
    • 77957579305 scopus 로고    scopus 로고
    • Structure-activity relationships of tulipalins, tuliposides, and related compounds as inhibitors of MurA
    • Mendgen, T., Scholz, T., and, Klein, C.D., (2010) Structure-activity relationships of tulipalins, tuliposides, and related compounds as inhibitors of MurA. Bioorg. Med. Chem. Lett. 20, 5757-5762.
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 5757-5762
    • Mendgen, T.1    Scholz, T.2    Klein, C.D.3
  • 22
    • 77951498554 scopus 로고    scopus 로고
    • Mechanisms for independent cytoplasmic inheritance of mitochondria and plastids in angiosperms
    • Nagata, N., (2010) Mechanisms for independent cytoplasmic inheritance of mitochondria and plastids in angiosperms. J. Plant Res. 123, 193-199.
    • (2010) J. Plant Res. , vol.123 , pp. 193-199
    • Nagata, N.1
  • 23
    • 15944386046 scopus 로고    scopus 로고
    • Stromules: A characteristic cell-specific feature of plastid morphology
    • Natesan, S.K.A., Sullivan, J.A., and, Gray, J.C., (2005) Stromules: a characteristic cell-specific feature of plastid morphology. J. Exp. Bot. 56, 787-797.
    • (2005) J. Exp. Bot. , vol.56 , pp. 787-797
    • Natesan, S.K.A.1    Sullivan, J.A.2    Gray, J.C.3
  • 24
    • 34548487513 scopus 로고    scopus 로고
    • A multicolored set of in vivo organelle markers for co-localization studies in Arabidopsis and other plants
    • Nelson, B.K., Cai, X., and, Nebenführ, A., (2007) A multicolored set of in vivo organelle markers for co-localization studies in Arabidopsis and other plants. Plant J. 51, 1126-1136.
    • (2007) Plant J. , vol.51 , pp. 1126-1136
    • Nelson, B.K.1    Cai, X.2    Nebenführ, A.3
  • 25
    • 16444371574 scopus 로고    scopus 로고
    • A synthetic green fluorescent protein gene for plant biotechnology
    • Niwa, Y., (2003) A synthetic green fluorescent protein gene for plant biotechnology. Plant Biotechnol. 20, 1-11.
    • (2003) Plant Biotechnol. , vol.20 , pp. 1-11
    • Niwa, Y.1
  • 26
    • 84861887576 scopus 로고    scopus 로고
    • A novel lactone-forming carboxylesterase: Molecular identification of a tuliposide A-converting enzyme in tulip
    • Nomura, T., Ogita, S., and, Kato, Y., (2012) A novel lactone-forming carboxylesterase: molecular identification of a tuliposide A-converting enzyme in tulip. Plant Physiol. 159, 565-578.
    • (2012) Plant Physiol. , vol.159 , pp. 565-578
    • Nomura, T.1    Ogita, S.2    Kato, Y.3
  • 27
    • 84878724496 scopus 로고    scopus 로고
    • Molecular diversity of tuliposide A-converting enzyme in the tulip
    • Nomura, T., Tsuchigami, A., Ogita, S., and, Kato, Y., (2013) Molecular diversity of tuliposide A-converting enzyme in the tulip. Biosci. Biotechnol. Biochem. 77, 1042-1048.
    • (2013) Biosci. Biotechnol. Biochem. , vol.77 , pp. 1042-1048
    • Nomura, T.1    Tsuchigami, A.2    Ogita, S.3    Kato, Y.4
  • 28
    • 84924569639 scopus 로고    scopus 로고
    • Environmentally benign process for the preparation of antimicrobial α-methylene-β-hydroxy-γ-butyrolactone (tulipalin B) from tulip biomass
    • Nomura, T., Hayashi, E., Kawakami, S., Ogita, S., and, Kato, Y., (2015) Environmentally benign process for the preparation of antimicrobial α-methylene-β-hydroxy-γ-butyrolactone (tulipalin B) from tulip biomass. Biosci. Biotechnol. Biochem. 79, 25-35.
    • (2015) Biosci. Biotechnol. Biochem. , vol.79 , pp. 25-35
    • Nomura, T.1    Hayashi, E.2    Kawakami, S.3    Ogita, S.4    Kato, Y.5
  • 29
    • 79960733211 scopus 로고    scopus 로고
    • Pollen vacuoles and their significance
    • Pacini, E., Jacquard, C., and, Clément, C., (2011) Pollen vacuoles and their significance. Planta, 234, 217-227.
    • (2011) Planta , vol.234 , pp. 217-227
    • Pacini, E.1    Jacquard, C.2    Clément, C.3
  • 30
    • 0032189784 scopus 로고    scopus 로고
    • Tulipaline and tuliposide in cultured explants of tulip bulb scales
    • van Rossum, M.W.P.C., Alberda, M., and, van der Plas, L.H.W., (1998) Tulipaline and tuliposide in cultured explants of tulip bulb scales. Phytochemistry, 49, 723-729.
    • (1998) Phytochemistry , vol.49 , pp. 723-729
    • Van Rossum, M.W.P.C.1    Alberda, M.2    Van Der Plas, L.H.W.3
  • 31
    • 0002127718 scopus 로고
    • Role of antimicrobial substances (tuliposides) in tulips attacked by Botrytis spp
    • Schönbeck, F., and, Schroeder, C., (1972) Role of antimicrobial substances (tuliposides) in tulips attacked by Botrytis spp. Physiol. Plant Pathol. 2, 91-99.
    • (1972) Physiol. Plant Pathol. , vol.2 , pp. 91-99
    • Schönbeck, F.1    Schroeder, C.2
  • 32
    • 73649107917 scopus 로고    scopus 로고
    • The antibacterial properties of 6-tuliposide B. Synthesis of 6-tuliposide B analogues and structure-activity relationship
    • Shigetomi, K., Shoji, K., Mitsuhashi, S., and, Ubukata, M., (2010) The antibacterial properties of 6-tuliposide B. Synthesis of 6-tuliposide B analogues and structure-activity relationship. Phytochemistry, 71, 312-324.
    • (2010) Phytochemistry , vol.71 , pp. 312-324
    • Shigetomi, K.1    Shoji, K.2    Mitsuhashi, S.3    Ubukata, M.4
  • 33
    • 79955855743 scopus 로고    scopus 로고
    • Asymmetric total synthesis of 6-tuliposide B and its biological activities against tulip pathogenic fungi
    • Shigetomi, K., Omoto, S., Kato, Y., and, Ubukata, M., (2011) Asymmetric total synthesis of 6-tuliposide B and its biological activities against tulip pathogenic fungi. Biosci. Biotechnol. Biochem. 75, 718-722.
    • (2011) Biosci. Biotechnol. Biochem. , vol.75 , pp. 718-722
    • Shigetomi, K.1    Omoto, S.2    Kato, Y.3    Ubukata, M.4
  • 36
    • 3242805974 scopus 로고    scopus 로고
    • Cloning and expression of a tomato cDNA encoding a methyl jasmonate cleaving esterase
    • Stuhlfelder, C., Mueller, M.J., and, Warzecha, H., (2004) Cloning and expression of a tomato cDNA encoding a methyl jasmonate cleaving esterase. Eur. J. Biochem. 271, 2976-2983.
    • (2004) Eur. J. Biochem. , vol.271 , pp. 2976-2983
    • Stuhlfelder, C.1    Mueller, M.J.2    Warzecha, H.3
  • 37
    • 0014248201 scopus 로고
    • Über die antibiotisch wirksamen substanzen der tulpe (Tulipa gesneriana)
    • Tschesche, R., Kämmerer, F.-J., Wulff, G., and, Schönbeck, F., (1968) Über die antibiotisch wirksamen substanzen der tulpe (Tulipa gesneriana). Tetrahedron Lett. 9, 701-706.
    • (1968) Tetrahedron Lett. , vol.9 , pp. 701-706
    • Tschesche, R.1    Kämmerer, F.-J.2    Wulff, G.3    Schönbeck, F.4
  • 38
    • 0001347256 scopus 로고
    • Über die struktur der antibiotisch aktiven substanzen der tulpe (Tulipa gesneriana L.)
    • Tschesche, R., Kämmerer, F.-J., and, Wulff, G., (1969) Über die struktur der antibiotisch aktiven substanzen der tulpe (Tulipa gesneriana L.). Chem. Ber. 102, 2057-2071.
    • (1969) Chem. Ber. , vol.102 , pp. 2057-2071
    • Tschesche, R.1    Kämmerer, F.-J.2    Wulff, G.3
  • 39
    • 26944450130 scopus 로고    scopus 로고
    • GIBBERELLIN INSENSITIVE DWARF1 encodes a soluble receptor for gibberellins
    • Ueguchi-Tanaka, M., Ashikari, M., Nakajima, M., et al. (2005) GIBBERELLIN INSENSITIVE DWARF1 encodes a soluble receptor for gibberellins. Nature, 437, 693-698.
    • (2005) Nature , vol.437 , pp. 693-698
    • Ueguchi-Tanaka, M.1    Ashikari, M.2    Nakajima, M.3
  • 40
    • 0001057790 scopus 로고
    • Outer pollen wall, an important accumulation site for flavonoids
    • Wiermann, R., and, Vieth, K., (1983) Outer pollen wall, an important accumulation site for flavonoids. Protoplasma, 118, 230-233.
    • (1983) Protoplasma , vol.118 , pp. 230-233
    • Wiermann, R.1    Vieth, K.2
  • 41
    • 84906779269 scopus 로고    scopus 로고
    • A flavonoid 3-O-glucoside:2′′-O-glucosyltransferase responsible for terminal modification of pollen-specific flavonols in Arabidopsis thaliana
    • Yonekura-Sakakibara, K., Nakabayashi, R., Sugawara, S., Tohge, T., Ito, T., Koyanagi, M., Kitajima, M., Takayama, H., and, Saito, K., (2014) A flavonoid 3-O-glucoside:2′′-O-glucosyltransferase responsible for terminal modification of pollen-specific flavonols in Arabidopsis thaliana. Plant J. 79, 769-782.
    • (2014) Plant J. , vol.79 , pp. 769-782
    • Yonekura-Sakakibara, K.1    Nakabayashi, R.2    Sugawara, S.3    Tohge, T.4    Ito, T.5    Koyanagi, M.6    Kitajima, M.7    Takayama, H.8    Saito, K.9


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.