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Volumn 84, Issue , 2012, Pages 56-67

Key structural features of cis-cinnamic acid as an allelochemical

Author keywords

Allelochemicals; Asteraceae; cis Cinnamic acid; Lactuca sativba L.; Lettuce; Plant growth inhibitors; Rosaceae; Spiraea thunbergii; Thunberg spirea

Indexed keywords

CINNAMIC ACID; CINNAMIC ACID DERIVATIVE; PHEROMONE;

EID: 84868096014     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2012.08.001     Document Type: Article
Times cited : (33)

References (53)
  • 1
    • 33847330157 scopus 로고    scopus 로고
    • Modular polyketide syntheses and cis-double bond formation: Establishment of activated cis-3-cyclohexylpropenoic acid as the diketide intermediate in phoslactomycin biosynthesis
    • M.M. Alhamadsheh, N. Palanjappan, S. DasChouduri, and K.A. Reynolds Modular polyketide syntheses and cis-double bond formation: establishment of activated cis-3-cyclohexylpropenoic acid as the diketide intermediate in phoslactomycin biosynthesis J. Am. Chem. Soc. 129 2007 1910 1911
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 1910-1911
    • Alhamadsheh, M.M.1    Palanjappan, N.2    Daschouduri, S.3    Reynolds, K.A.4
  • 2
    • 0000262852 scopus 로고    scopus 로고
    • High selective synthesis of Z-unsaturated esters by using new Horner-Emmons reagents. ethyl (diarylphosphono)acetates
    • K. Ando High selective synthesis of Z-unsaturated esters by using new Horner-Emmons reagents. ethyl (diarylphosphono)acetates J. Org. Chem. 62 1997 1934 1939
    • (1997) J. Org. Chem. , vol.62 , pp. 1934-1939
    • Ando, K.1
  • 3
    • 0034725908 scopus 로고    scopus 로고
    • Z-Selective Horner-Wadsworth-Emmons reaction of ethyl (diarylphosphono)acetates using sodium iodide and DBU
    • K. Ando, T. Oishi, M. Hirama, H. Ohno, and T. Ibuka Z-Selective Horner-Wadsworth-Emmons reaction of ethyl (diarylphosphono)acetates using sodium iodide and DBU J. Org. Chem. 65 2000 4745 4749
    • (2000) J. Org. Chem. , vol.65 , pp. 4745-4749
    • Ando, K.1    Oishi, T.2    Hirama, M.3    Ohno, H.4    Ibuka, T.5
  • 5
    • 17444407015 scopus 로고    scopus 로고
    • Two-carbon homologation of ketones via silyl ketene acetals: Synthesis of α, β-unsaturated acids and α-trimethylsilyl δ-ketoacids
    • M. Bellassoued, S. Mouelhi, P. Fromentin, and A. Gonzalez Two-carbon homologation of ketones via silyl ketene acetals: synthesis of α, β-unsaturated acids and α-trimethylsilyl δ-ketoacids J. Organomet. Chem. 690 2005 2172 2179
    • (2005) J. Organomet. Chem. , vol.690 , pp. 2172-2179
    • Bellassoued, M.1    Mouelhi, S.2    Fromentin, P.3    Gonzalez, A.4
  • 6
    • 37049214786 scopus 로고
    • The method of probits
    • C.I. Bliss The method of probits Science 79 1934 38 39
    • (1934) Science , vol.79 , pp. 38-39
    • Bliss, C.I.1
  • 8
    • 22744449461 scopus 로고    scopus 로고
    • Cis- and trans-cinnamic acids have different effects on the catalytic properties of arabidopsos phenylalanine ammonia lyases PAL1, PAL2, and PAL4
    • M.J. Chen, V. Vijaykumar, B.W. Lu, B. Xia, and N. Li Cis- And trans-cinnamic acids have different effects on the catalytic properties of arabidopsos phenylalanine ammonia lyases PAL1, PAL2, and PAL4 J. Integrative Plant Biol. 47 2005 67 75
    • (2005) J. Integrative Plant Biol. , vol.47 , pp. 67-75
    • Chen, M.J.1    Vijaykumar, V.2    Lu, B.W.3    Xia, B.4    Li, N.5
  • 9
    • 23944515551 scopus 로고
    • Photochemical isomerization of cinnamic acid in aqueous solutions
    • B.H. Clampitt, and J.W. Callis Photochemical isomerization of cinnamic acid in aqueous solutions J. Phys. Chem. 66 1962 201 204
    • (1962) J. Phys. Chem. , vol.66 , pp. 201-204
    • Clampitt, B.H.1    Callis, J.W.2
  • 10
    • 34547482525 scopus 로고    scopus 로고
    • The first cyclopropanation reaction of unmasked α, β-unsaturated carboxylic acids: Direct and complete stereospecific synthesis of cyclopropanecarboxylic acids promoted by Sm/CHI3
    • J.M. Concellón, H. Rodríguez-Solla, and C. Simal The first cyclopropanation reaction of unmasked α, β-unsaturated carboxylic acids: direct and complete stereospecific synthesis of cyclopropanecarboxylic acids promoted by Sm/CHI3 Org. Lett. 9 2007 2685 2688
    • (2007) Org. Lett. , vol.9 , pp. 2685-2688
    • Concellón, J.M.1    Rodríguez-Solla, H.2    Simal, C.3
  • 11
    • 0028955942 scopus 로고
    • Organoaluminium-promoted cycloaddition of trialkylssilylketene with aldehydes: A new, stereoselective approach to cis-2-oxetanones and 2(Z)-alkenoic acids
    • A.B. Concepcion, K. Maruoka, and H. Yamamoto Organoaluminium-promoted cycloaddition of trialkylssilylketene with aldehydes: a new, stereoselective approach to cis-2-oxetanones and 2(Z)-alkenoic acids Tetrahedron 51 1995 4011 4020
    • (1995) Tetrahedron , vol.51 , pp. 4011-4020
    • Concepcion, A.B.1    Maruoka, K.2    Yamamoto, H.3
  • 12
    • 33751391117 scopus 로고
    • A practical, highly enantioselective synthesis of the taxol side chain via asymmetric catalysis
    • L. Deng, and E.N. Jacobsen A practical, highly enantioselective synthesis of the taxol side chain via asymmetric catalysis J. Org. Chem. 57 1992 4320 4323
    • (1992) J. Org. Chem. , vol.57 , pp. 4320-4323
    • Deng, L.1    Jacobsen, E.N.2
  • 13
    • 0001781416 scopus 로고
    • An efficient, enantioselective synthesis of the taxol side chain
    • J. Denis, A.E. Greene, A.A. Serra, and M. Luche An efficient, enantioselective synthesis of the taxol side chain J. Org. Chem. 51 1986 46 50
    • (1986) J. Org. Chem. , vol.51 , pp. 46-50
    • Denis, J.1    Greene, A.E.2    Serra, A.A.3    Luche, M.4
  • 15
    • 79952041678 scopus 로고    scopus 로고
    • Cis-cinnamic acid-enhanced 1 gene plays a role in regulation of Arabidopsis bolting
    • D. Guo, W.S. Wong, W.Z. Xu, F.F. Sun, D.J.Q. Qing, and N. Li Cis-cinnamic acid-enhanced 1 gene plays a role in regulation of Arabidopsis bolting Plant Mol. Biol. 75 2011 481 495
    • (2011) Plant Mol. Biol. , vol.75 , pp. 481-495
    • Guo, D.1    Wong, W.S.2    Xu, W.Z.3    Sun, F.F.4    Qing, D.J.Q.5    Li, N.6
  • 16
    • 2442736240 scopus 로고
    • A physiological analysis of a growth substance
    • -S.A.J. Haagen, and F.W. Went A physiological analysis of a growth substance Proc. K. Akad. Wet. 38 1935 852 857
    • (1935) Proc. K. Akad. Wet. , vol.38 , pp. 852-857
    • Haagen, S.A.J.1    Went, F.W.2
  • 19
    • 18144397862 scopus 로고    scopus 로고
    • Plant growth inhibition by cis-cinnamoyl glucoside and cis-cinnamic acid
    • S. Hiradate, S. Morita, A. Furubayashi, Y. Fujii, and J. Harada Plant growth inhibition by cis-cinnamoyl glucoside and cis-cinnamic acid J. Chem. Ecol. 31 2005 591 601
    • (2005) J. Chem. Ecol. , vol.31 , pp. 591-601
    • Hiradate, S.1    Morita, S.2    Furubayashi, A.3    Fujii, Y.4    Harada, J.5
  • 20
    • 0000747069 scopus 로고
    • Photochemical and thermal isomerizations of cis- and trans-cinnamic acids, and their photostationary state
    • M.B. Hocking Photochemical and thermal isomerizations of cis- and trans-cinnamic acids, and their photostationary state Can. J. Chem. 47 1969 4567 4576
    • (1969) Can. J. Chem. , vol.47 , pp. 4567-4576
    • Hocking, M.B.1
  • 21
    • 84891744205 scopus 로고
    • Extension-growth activities of some cyclopropnae derivatives, a new class of antiauxin
    • N.P. Kefford Extension-growth activities of some cyclopropnae derivatives, a new class of antiauxin Aust. J. Biol. Sci. 12 1959 257 262
    • (1959) Aust. J. Biol. Sci. , vol.12 , pp. 257-262
    • Kefford, N.P.1
  • 22
    • 0041736591 scopus 로고    scopus 로고
    • Coupling reactions of α-bromoalkenyl phosphonates with aryl boronic acids and alkenyl borates
    • Y. Kobayashi, and A.D. William Coupling reactions of α-bromoalkenyl phosphonates with aryl boronic acids and alkenyl borates Org. Lett. 4 2002 4241 4244
    • (2002) Org. Lett. , vol.4 , pp. 4241-4244
    • Kobayashi, Y.1    William, A.D.2
  • 23
    • 12444319270 scopus 로고    scopus 로고
    • Palladium- and nickel-catalyzed coupling reactions of α-bromoalkenylphosphonates with arylboronic acids and lithium alkenylborates
    • Y. Kobayashi, and A.D. William Palladium- and nickel-catalyzed coupling reactions of α-bromoalkenylphosphonates with arylboronic acids and lithium alkenylborates Adv. Synth. Catal. 346 2004 1749 1757
    • (2004) Adv. Synth. Catal. , vol.346 , pp. 1749-1757
    • Kobayashi, Y.1    William, A.D.2
  • 24
    • 2442722118 scopus 로고
    • Phytohormones: Structure and physiological activity
    • J.B. Koepfli, K.V. Thimann, and F.W. Went Phytohormones: structure and physiological activity I. J. Biol. Chem. 122 1938 763 780
    • (1938) I. J. Biol. Chem. , vol.122 , pp. 763-780
    • Koepfli, J.B.1    Thimann, K.V.2    Went, F.W.3
  • 25
    • 8744273848 scopus 로고    scopus 로고
    • Highly (Z)-selective synthesis of β-monosubstituted α, β-unsaturated cyanides using the Peterson reaction
    • S. Kojima, T. Fukuzaki, A. Yamakawa, and Y. Murai Highly (Z)-selective synthesis of β-monosubstituted α, β-unsaturated cyanides using the Peterson reaction Org. Lett. 6 2004 3917 3920
    • (2004) Org. Lett. , vol.6 , pp. 3917-3920
    • Kojima, S.1    Fukuzaki, T.2    Yamakawa, A.3    Murai, Y.4
  • 26
    • 0006095573 scopus 로고
    • Photochemical cis-trans isomerization of p-dimethylaminocinnamic acid nitrile
    • E. Lippert, and W. Lüder Photochemical cis-trans isomerization of p-dimethylaminocinnamic acid nitrile J. Phys. Chem. 66 1962 2430 2434
    • (1962) J. Phys. Chem. , vol.66 , pp. 2430-2434
    • Lippert, E.1    Lüder, W.2
  • 27
    • 0345871990 scopus 로고    scopus 로고
    • A novel class of tunable zinc reagents (RXZnCHY) for efficient cyclopropanation of olefins
    • J.C. Lorenz, J. Long, Z. Yang, S. Xue, Y. Xie, and Y. Shi A novel class of tunable zinc reagents (RXZnCHY) for efficient cyclopropanation of olefins J. Org. Chem. 69 2004 327 334
    • (2004) J. Org. Chem. , vol.69 , pp. 327-334
    • Lorenz, J.C.1    Long, J.2    Yang, Z.3    Xue, S.4    Xie, Y.5    Shi, Y.6
  • 29
    • 78651509932 scopus 로고    scopus 로고
    • Visible-light photoredox catalysis: Dehalogenation of vicinal dibromo-, α-halo-, and α, α-dibromocarbonyl compounds
    • T. Maji, A. Karmakar, and O. Reiser Visible-light photoredox catalysis: dehalogenation of vicinal dibromo-, α-halo-, and α, α-dibromocarbonyl compounds J. Org. Chem. 76 2010 736 739
    • (2010) J. Org. Chem. , vol.76 , pp. 736-739
    • Maji, T.1    Karmakar, A.2    Reiser, O.3
  • 30
    • 80053199959 scopus 로고    scopus 로고
    • Stereoselective synthesis of β-glycosyl esters of cis-cinnamic acid and its derivatives using unprotected glycosyl donors
    • K. Matsuo, K. Nishikawa, and M. Shindo Stereoselective synthesis of β-glycosyl esters of cis-cinnamic acid and its derivatives using unprotected glycosyl donors Tetrahedron Lett. 52 2011 5688 5692
    • (2011) Tetrahedron Lett. , vol.52 , pp. 5688-5692
    • Matsuo, K.1    Nishikawa, K.2    Shindo, M.3
  • 31
    • 77953121861 scopus 로고    scopus 로고
    • Efficient alkenation of aldehydes and ketones to α, β-unsaturated esters using α, α-bis(dimethylsilyl)-substituted esters
    • K. Miura, M. Ebine, K. Ootsuka, J. Ichikawa, and A. Hosomi Efficient alkenation of aldehydes and ketones to α, β-unsaturated esters using α, α-bis(dimethylsilyl)-substituted esters Chem. Lett. 38 2009 832 833
    • (2009) Chem. Lett. , vol.38 , pp. 832-833
    • Miura, K.1    Ebine, M.2    Ootsuka, K.3    Ichikawa, J.4    Hosomi, A.5
  • 32
    • 51549113575 scopus 로고    scopus 로고
    • Highly stereoselective synthesis of cis-alkenyl pinacolboronates and potassium cis-alkenyltrifluoroborates via a hydroboration/ protodeboronation approach
    • G.A. Molander, and N.M. Ellis Highly stereoselective synthesis of cis-alkenyl pinacolboronates and potassium cis-alkenyltrifluoroborates via a hydroboration/ protodeboronation approach J. Org. Chem. 73 2008 6841 6844
    • (2008) J. Org. Chem. , vol.73 , pp. 6841-6844
    • Molander, G.A.1    Ellis, N.M.2
  • 33
    • 1542323728 scopus 로고    scopus 로고
    • Plant growth inhibiting effect in arbor plants
    • (in Japanese)
    • S. Morita, M. Ito, Y. Fujii, and J. Harada Plant growth inhibiting effect in arbor plants J. Weed Sci. Tecg. 46 Suppl. 2001 134 135 (in Japanese)
    • (2001) J. Weed Sci. Tecg. , vol.46 , Issue.SUPPL. , pp. 134-135
    • Morita, S.1    Ito, M.2    Fujii, Y.3    Harada, J.4
  • 34
    • 15944367446 scopus 로고    scopus 로고
    • Screening of an allelopahtic potential in arbor species
    • S. Morita, M. Ito, and J. Harada Screening of an allelopahtic potential in arbor species Weed Biol. Manage. 5 2005 26 30
    • (2005) Weed Biol. Manage. , vol.5 , pp. 26-30
    • Morita, S.1    Ito, M.2    Harada, J.3
  • 35
    • 23944521821 scopus 로고    scopus 로고
    • Cis-cinnamoyl glucoside as a major plant growth inhibitor contained in Spiraea prunifolia
    • S. Morita, S. Hiradate, Y. Fujii, and J. Harada Cis-cinnamoyl glucoside as a major plant growth inhibitor contained in Spiraea prunifolia Plant Growth Reg. 46 2005 125 131
    • (2005) Plant Growth Reg. , vol.46 , pp. 125-131
    • Morita, S.1    Hiradate, S.2    Fujii, Y.3    Harada, J.4
  • 37
    • 0033941957 scopus 로고    scopus 로고
    • Tandem Michael-Wittig-Horner reaction: One-pot synthesis of δ-substituted α, β-unsaturated carboxylic acid derivatives - Application to a concise synthesis of (Z)- and (E)-ochtoden-1-al
    • O. Piva, and S. Comesse Tandem Michael-Wittig-Horner reaction: one-pot synthesis of δ-substituted α, β-unsaturated carboxylic acid derivatives - application to a concise synthesis of (Z)- and (E)-ochtoden-1-al Eur. J. Org. Chem. 2000 2417 2424
    • (2000) Eur. J. Org. Chem. , pp. 2417-2424
    • Piva, O.1    Comesse, S.2
  • 38
    • 0037549290 scopus 로고
    • Influence of nucleophiles on the high temperature aqueous isomerization of cis- to trans-cinnamic acid
    • G.A. Reed, D.R. Dimmel, and E.W. Malcolm Influence of nucleophiles on the high temperature aqueous isomerization of cis- to trans-cinnamic acid J. Org. Chem. 58 1993 6364 6371
    • (1993) J. Org. Chem. , vol.58 , pp. 6364-6371
    • Reed, G.A.1    Dimmel, D.R.2    Malcolm, E.W.3
  • 40
    • 0024190582 scopus 로고
    • Effects of sunlight irradiation on the assimilation of hydrocinnamic and trans-cinnamic acids by marine bacteria
    • J.-F. Rontani, P. Bonin, and G. Giusti Effects of sunlight irradiation on the assimilation of hydrocinnamic and trans-cinnamic acids by marine bacteria Mar. Chem. 23 1988 41 50
    • (1988) Mar. Chem. , vol.23 , pp. 41-50
    • Rontani, J.-F.1    Bonin, P.2    Giusti, G.3
  • 41
    • 0346609922 scopus 로고    scopus 로고
    • Tungsten(0) alkylidene complexes stabilized as pyridinium ylides: New aspects of their synthesis and reactivity
    • H. Rudler, and T. Durand-Réville Tungsten(0) alkylidene complexes stabilized as pyridinium ylides: new aspects of their synthesis and reactivity J. Organomet. Chem. 617-618 2001 571 587
    • (2001) J. Organomet. Chem. , vol.617-618 , pp. 571-587
    • Rudler, H.1    Durand-Réville, T.2
  • 42
    • 78049512042 scopus 로고    scopus 로고
    • Photoisomerization of ionic liquid ammonium cinnamates: One-pot synthesis-isolation of Z-cinnamic acids
    • M.L. Salum, C.J. Robles, and R. Erra-Balsells Photoisomerization of ionic liquid ammonium cinnamates: one-pot synthesis-isolation of Z-cinnamic acids Org. Lett. 12 2011 4808 4811
    • (2011) Org. Lett. , vol.12 , pp. 4808-4811
    • Salum, M.L.1    Robles, C.J.2    Erra-Balsells, R.3
  • 43
    • 2442671604 scopus 로고    scopus 로고
    • Stereoselective olefination of unfunctionalized ketones via ynolates
    • M. Shindo, Y. Sato, T. Yoshikawa, R. Koretsune, and K. Shishido Stereoselective olefination of unfunctionalized ketones via ynolates J. Org. Chem. 69 2004 3912 3916
    • (2004) J. Org. Chem. , vol.69 , pp. 3912-3916
    • Shindo, M.1    Sato, Y.2    Yoshikawa, T.3    Koretsune, R.4    Shishido, K.5
  • 45
    • 0000740782 scopus 로고    scopus 로고
    • Nickel-promoted alkylative or arylative carboxylation of alkynes
    • M. Takimoto, K. Shimizu, and M. Mori Nickel-promoted alkylative or arylative carboxylation of alkynes Org. Lett. 3 2001 3345 3347
    • (2001) Org. Lett. , vol.3 , pp. 3345-3347
    • Takimoto, M.1    Shimizu, K.2    Mori, M.3
  • 46
    • 51749085800 scopus 로고    scopus 로고
    • An atom-economic and selective ruthenium-catalyzed redox isomerization of propargylic alcohols. An efficient strategy for the synthesis of leukotrienes
    • B.M. Trost, and R.C. Livingston An atom-economic and selective ruthenium-catalyzed redox isomerization of propargylic alcohols. An efficient strategy for the synthesis of leukotrienes J. Am. Chem. Soc. 130 2008 11970 11978
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 11970-11978
    • Trost, B.M.1    Livingston, R.C.2
  • 47
    • 0000559920 scopus 로고
    • Light-induced isomerization and dimerization of cinnamic acid derivatives in cell walls
    • L.B. Turner, I. Mueller-Harvey, and A.B. Mcallan Light-induced isomerization and dimerization of cinnamic acid derivatives in cell walls Phytochemistry 33 1993 791 796
    • (1993) Phytochemistry , vol.33 , pp. 791-796
    • Turner, L.B.1    Mueller-Harvey, I.2    McAllan, A.B.3
  • 48
    • 37349038497 scopus 로고    scopus 로고
    • Influence of the double-bond geometry of the Michael accepter on copper-catalyzed asymmetric conjugate addition
    • A.M. Vuagonoux-d', and A. Alexakis Influence of the double-bond geometry of the Michael accepter on copper-catalyzed asymmetric conjugate addition Eur. J. Org. Chem. 2007 5852 5860
    • (2007) Eur. J. Org. Chem. , pp. 5852-5860
    • Vuagonoux-d, A.M.1    Alexakis, A.2
  • 49
    • 0037169964 scopus 로고    scopus 로고
    • Allelochemicals as leads for new herbicides and agrochemicals
    • J.R. Vyvyan Allelochemicals as leads for new herbicides and agrochemicals Tetrahedron 58 2002 1631 1646
    • (2002) Tetrahedron , vol.58 , pp. 1631-1646
    • Vyvyan, J.R.1
  • 50
    • 0345391556 scopus 로고
    • The utility of phosphonate carbanions in olefin synthesis
    • W.S. Wadsworth Jr., and W.D. Emmons The utility of phosphonate carbanions in olefin synthesis J. Am. Chem. Soc. 83 1961 1733 1738
    • (1961) J. Am. Chem. Soc. , vol.83 , pp. 1733-1738
    • Wadsworth, Jr.W.S.1    Emmons, W.D.2
  • 52
    • 2442724481 scopus 로고    scopus 로고
    • A UV-light activated cinnamic acid isomer regulates plant growth and gravitropism via an ethylene receptor-independent pathway
    • X.X. Yang, H.W. Choi, S.F. Yang, and N. Li A UV-light activated cinnamic acid isomer regulates plant growth and gravitropism via an ethylene receptor-independent pathway Aust. J. Plant Physiol. 26 1999 325 335
    • (1999) Aust. J. Plant Physiol. , vol.26 , pp. 325-335
    • Yang, X.X.1    Choi, H.W.2    Yang, S.F.3    Li, N.4
  • 53
    • 0028929021 scopus 로고
    • Synthesis of 5-aryl and vinyl tetrazoles by the palladium-catalyzed cross-coupling reaction
    • K.Y. Yi, and S. Yoo Synthesis of 5-aryl and vinyl tetrazoles by the palladium-catalyzed cross-coupling reaction Tetrahedron Lett. 36 1995 1679 1682
    • (1995) Tetrahedron Lett. , vol.36 , pp. 1679-1682
    • Yi, K.Y.1    Yoo, S.2


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