메뉴 건너뛰기




Volumn 4, Issue 5, 2012, Pages 1315-1325

Application of an integrated LC-UV-MS-NMR platform to the identification of secondary metabolites from cell cultures: Benzophenanthridine alkaloids from elicited Eschscholzia californica (california poppy) cell cultures

Author keywords

[No Author keywords available]

Indexed keywords

CALIFORNIA; ESCHSCHOLZIA CALIFORNICA CELLS; EXPRESSION SYSTEM; HIGH YIELD; HPLC-UV; MICRO DROPLETS; MICRO-SCALES; NATURAL PRODUCTS; OFFLINE; OPTIMAL SENSITIVITY; PLANT CELLS; RAPID ASSAY; SECONDARY METABOLITES; STRUCTURAL IDENTIFICATION; TIME POINTS; WHOLE PLANTS; YEAST EXTRACTS;

EID: 84860766914     PISSN: 17599660     EISSN: 17599679     Source Type: Journal    
DOI: 10.1039/c2ay05803k     Document Type: Article
Times cited : (21)

References (39)
  • 1
    • 0010507986 scopus 로고    scopus 로고
    • Cultivating the pharmacopoeia
    • A. D. Kinghorn E.-K. Seo Cultivating the pharmacopoeia CHEMTECH 1996 26 46 54 (Pubitemid 126495709)
    • (1996) CHEMTECH , vol.26 , Issue.7 , pp. 46-54
    • Kinghorn, A.D.1    Seo, E.-K.2
  • 2
    • 2442572066 scopus 로고    scopus 로고
    • Plant-derived secondary metabolites as defensive chemicals in herbivorous insects: A case study in chemical ecology
    • DOI 10.1007/s00425-004-1249-y
    • T. Hartmann Plant-derived secondary metabolites as defensive chemicals in herbivorous insects: a case study in chemical ecology Planta 2004 219 1 1 4 (Pubitemid 38642128)
    • (2004) Planta , vol.219 , Issue.1 , pp. 1-4
    • Hartmann, T.1
  • 4
    • 65349184006 scopus 로고    scopus 로고
    • Opportunities in metabolic engineering to facilitate scalable alkaloid production
    • E. Leonard W. Runguphan S. O'Connor K. J. Prather Opportunities in metabolic engineering to facilitate scalable alkaloid production Nat. Chem. Biol. 2009 5 5 292 300
    • (2009) Nat. Chem. Biol. , vol.5 , Issue.5 , pp. 292-300
    • Leonard, E.1    Runguphan, W.2    O'Connor, S.3    Prather, K.J.4
  • 5
    • 0000018728 scopus 로고
    • Plant cell culture combined with chemistry: A powerful route to complex natural products
    • (Copyright (C) 2011 American Chemical Society (ACS). All Rights Reserved.)
    • J. P. Kutney Plant cell culture combined with chemistry: a powerful route to complex natural products Acc. Chem. Res. 1993 26 559 566
    • (1993) Acc. Chem. Res. , vol.26 , pp. 559-566
    • Kutney, J.P.1
  • 6
    • 0041960257 scopus 로고    scopus 로고
    • The complexity of pathogen defense in plants
    • (Copyright (C) 2011 American Chemical Society (ACS). All Rights Reserved.)
    • M. Odjakova C. Hadjiivanova The complexity of pathogen defense in plants Bulg. J. Plant Physiol. 2001 27 101 109
    • (2001) Bulg. J. Plant Physiol. , vol.27 , pp. 101-109
    • Odjakova, M.1    Hadjiivanova, C.2
  • 8
    • 33750487887 scopus 로고    scopus 로고
    • Fungal elicitation to plants and its application in natural medicines
    • (Copyright (C) 2011 American Chemical Society (ACS). All Rights Reserved.)
    • P. Hou S. Guo Fungal elicitation to plants and its application in natural medicines Zhongcaoyao 2002 33 855 857
    • (2002) Zhongcaoyao , vol.33 , pp. 855-857
    • Hou, P.1    Guo, S.2
  • 9
    • 84866023340 scopus 로고    scopus 로고
    • Sample preparation of plant material
    • (Copyright (C) 2011 American Chemical Society (ACS). All Rights Reserved.)
    • A. Oniszczuk A. Hawryl Sample preparation of plant material Chromatogr. Sci. Ser. 2011 102 107 149
    • (2011) Chromatogr. Sci. Ser. , vol.102 , pp. 107-149
    • Oniszczuk, A.1    Hawryl, A.2
  • 10
    • 84860748550 scopus 로고    scopus 로고
    • Photodiode array (PDA) and other detection methods in HPLC of plant metabolites
    • (Copyright (C) 2011 American Chemical Society (ACS). All Rights Reserved.)
    • W. Markowski M. Waksmundzka-Hajnos Photodiode array (PDA) and other detection methods in HPLC of plant metabolites Chromatogr. Sci. Ser. 2011 102 331 350
    • (2011) Chromatogr. Sci. Ser. , vol.102 , pp. 331-350
    • Markowski, W.1    Waksmundzka-Hajnos, M.2
  • 11
    • 58249127818 scopus 로고    scopus 로고
    • Determination of paclitaxel and other six taxoids in Taxus species by high-performance liquid chromatography-tandem mass spectrometry
    • S. Li Y. Fu Y. Zu R. Sun Y. Wang L. Zhang H. Luo C. Gu T. Efferth Determination of paclitaxel and other six taxoids in Taxus species by high-performance liquid chromatography-tandem mass spectrometry J. Pharm. Biomed. Anal. 2009 49 1 81 89
    • (2009) J. Pharm. Biomed. Anal. , vol.49 , Issue.1 , pp. 81-89
    • Li, S.1    Fu, Y.2    Zu, Y.3    Sun, R.4    Wang, Y.5    Zhang, L.6    Luo, H.7    Gu, C.8    Efferth, T.9
  • 12
    • 5644269154 scopus 로고    scopus 로고
    • Improved liquid chromatography-mass spectrometry performance in quantitative analysis using a nanosplitter interface
    • DOI 10.1016/j.chroma.2004.08.076, PII S002196730401430X
    • C. L. Andrews C. P. Yu E. Yang P. Vouros Improved liquid chromatography-mass spectrometry performance in quantitative analysis using a nanosplitter interface J. Chromatogr., A 2004 1053 1-2 151 159 (Pubitemid 39369769)
    • (2004) Journal of Chromatography A , vol.1053 , Issue.SPEC. ISS.1-2 , pp. 151-159
    • Andrews, C.L.1    Yu, C.-P.2    Yang, E.3    Vouros, P.4
  • 13
    • 31544444688 scopus 로고    scopus 로고
    • Incorporation of a nanosplitter interface into an LC-MS-RD system to facilitate drug metabolism studies
    • DOI 10.1002/jms.944
    • C. L. Andrews F. Li E. Yang C. P. Yu P. Vouros Incorporation of a nanosplitter interface into an LC-MS-RD system to facilitate drug metabolism studies J. Mass Spectrom. 2006 41 1 43 49 (Pubitemid 43164833)
    • (2006) Journal of Mass Spectrometry , vol.41 , Issue.1 , pp. 43-49
    • Andrews, C.L.1    Li, F.2    Yang, E.3    Yu, C.-P.4    Vouros, P.5
  • 16
    • 40149094940 scopus 로고    scopus 로고
    • Quantitative 1H NMR metabolomics reveals extensive metabolic reprogramming of primary and secondary metabolism in elicitor-treated opium poppy cell cultures
    • K. G. Zulak A. M. Weljie H. J. Vogel P. J. Facchini Quantitative 1H NMR metabolomics reveals extensive metabolic reprogramming of primary and secondary metabolism in elicitor-treated opium poppy cell cultures BMC Plant Biol. 2008 8 5
    • (2008) BMC Plant Biol. , vol.8 , pp. 5
    • Zulak, K.G.1    Weljie, A.M.2    Vogel, H.J.3    Facchini, P.J.4
  • 17
    • 53749090789 scopus 로고    scopus 로고
    • 1H nuclear magnetic resonance metabolite profiling as a functional genomics platform to investigate alkaloid biosynthesis in opium poppy
    • DOI 10.1104/pp.108.120493
    • J. M. Hagel A. M. Weljie H. J. Vogel P. J. Facchini Quantitative 1H nuclear magnetic resonance metabolite profiling as a functional genomics platform to investigate alkaloid biosynthesis in opium poppy Plant Physiol. 2008 147 4 1805 1821 (Pubitemid 352844223)
    • (2008) Plant Physiology , vol.147 , Issue.4 , pp. 1805-1821
    • Hagel, J.M.1    Weljie, A.M.2    Vogel, H.J.3    Facchini, P.J.4
  • 20
    • 55549089989 scopus 로고    scopus 로고
    • Microscale LC-MS-NMR platform applied to the identification of active cyanobacterial metabolites
    • Y. Lin S. Schiavo J. Orjala P. Vouros R. Kautz Microscale LC-MS-NMR platform applied to the identification of active cyanobacterial metabolites Anal. Chem. 2008 80 21 8045 8054
    • (2008) Anal. Chem. , vol.80 , Issue.21 , pp. 8045-8054
    • Lin, Y.1    Schiavo, S.2    Orjala, J.3    Vouros, P.4    Kautz, R.5
  • 22
    • 0031989836 scopus 로고    scopus 로고
    • High-resolution microcoil NMR for analysis of mass-limited, nanoliter samples
    • (Copyright (C) 2011 American Chemical Society (ACS). All Rights Reserved.)
    • D. L. Olson M. E. Lacey J. V. Sweedler High-resolution microcoil NMR for analysis of mass-limited, nanoliter samples Anal. Chem. 1998 70 645 650
    • (1998) Anal. Chem. , vol.70 , pp. 645-650
    • Olson, D.L.1    Lacey, M.E.2    Sweedler, J.V.3
  • 23
    • 13544250706 scopus 로고    scopus 로고
    • High-throughput microcoil NMR of compound libraries using zero-dispersion segmented flow analysis
    • DOI 10.1021/cc0498940
    • R. A. Kautz W. K. Goetzinger B. L. Karger High-throughput microcoil NMR of compound libraries using zero-dispersion segmented flow analysis J. Comb. Chem. 2005 7 1 14 20 (Pubitemid 40221561)
    • (2005) Journal of Combinatorial Chemistry , vol.7 , Issue.1 , pp. 14-20
    • Kautz, R.A.1    Goetzinger, W.K.2    Karger, B.L.3
  • 24
    • 0000486769 scopus 로고
    • Dynamics of benzophenanthridine alkaloid production in suspension cultures of Eschscholtzia californica after treatment with a yeast elicitor
    • (Copyright (C) 2011 American Chemical Society (ACS). All Rights Reserved.)
    • M. A. Collinge P. E. Brodelius Dynamics of benzophenanthridine alkaloid production in suspension cultures of Eschscholtzia californica after treatment with a yeast elicitor Phytochemistry 1989 28 1101 1104
    • (1989) Phytochemistry , vol.28 , pp. 1101-1104
    • Collinge, M.A.1    Brodelius, P.E.2
  • 25
    • 0000504253 scopus 로고
    • The formation of benzophenanthridine alkaloids
    • (Copyright (C) 2011 American Chemical Society (ACS). All Rights Reserved.)
    • M. H. Zenk The formation of benzophenanthridine alkaloids Pure Appl. Chem. 1994 66 2023 2028
    • (1994) Pure Appl. Chem. , vol.66 , pp. 2023-2028
    • Zenk, M.H.1
  • 26
    • 46449132433 scopus 로고    scopus 로고
    • Differential induction of protein expression and benzophenanthridine alkaloid accumulation in Eschscholtzia californica suspension cultures by methyl jasmonate and yeast extract
    • H. Y. Cho H. S. Rhee S. Y. Yoon J. M. Park Differential induction of protein expression and benzophenanthridine alkaloid accumulation in Eschscholtzia californica suspension cultures by methyl jasmonate and yeast extract J. Microbiol. Biotechnol. 2008 18 2 255 262
    • (2008) J. Microbiol. Biotechnol. , vol.18 , Issue.2 , pp. 255-262
    • Cho, H.Y.1    Rhee, H.S.2    Yoon, S.Y.3    Park, J.M.4
  • 27
    • 43049130724 scopus 로고    scopus 로고
    • Synergistic effects of sequential treatment with methyl jasmonate, salicylic acid and yeast extract on benzophenanthridine alkaloid accumulation and protein expression in Eschscholtzia californica suspension cultures
    • (Copyright (C) 2011 U.S. National Library of Medicine.)
    • H.-Y. Cho S. Y. Son H. S. Rhee S.-Y. H. Yoon C. W. T. Lee-Parsons J. M. Park Synergistic effects of sequential treatment with methyl jasmonate, salicylic acid and yeast extract on benzophenanthridine alkaloid accumulation and protein expression in Eschscholtzia californica suspension cultures J. Biotechnol. 2008 135 117 122
    • (2008) J. Biotechnol. , vol.135 , pp. 117-122
    • Cho, H.-Y.1    Son, S.Y.2    Rhee, H.S.3    Yoon, S.-Y.H.4    Lee-Parsons, C.W.T.5    Park, J.M.6
  • 28
    • 0033608561 scopus 로고    scopus 로고
    • Antibacterial agents in the control of supragingival plaque - A review
    • B. M. Eley Antibacterial agents in the control of supragingival plaque - a review Br. Dent. J. 1999 186 6 286 296
    • (1999) Br. Dent. J. , vol.186 , Issue.6 , pp. 286-296
    • Eley, B.M.1
  • 29
    • 33749326967 scopus 로고    scopus 로고
    • The effect of chelerythrine on cell growth, apoptosis, and cell cycle in human normal and cancer cells in comparison with sanguinarine
    • DOI 10.1007/s10565-006-0109-x
    • J. Malikova A. Zdarilova A. Hlobilkova J. Ulrichova The effect of chelerythrine on cell growth, apoptosis, and cell cycle in human normal and cancer cells in comparison with sanguinarine Cell Biol. Toxicol. 2006 22 6 439 453 (Pubitemid 44488532)
    • (2006) Cell Biology and Toxicology , vol.22 , Issue.6 , pp. 439-453
    • Malikova, J.1    Zdarilova, A.2    Hlobilkova, A.3    Ulrichova, J.4
  • 31
    • 4444220152 scopus 로고    scopus 로고
    • Sanguinarine causes cell cyle blockade and apoptosis of human prostate carcinoma cells via modulation of cylin kinase inhibitor-cyclin-cyclin-dependent kinase machinery
    • V. M. Adhami M. H. Aziz S. R. Reagan-Shaw M. Nihal H. Mukhtar N. Ahmad Sanguinarine causes cell cycle blockade and apoptosis of human prostate carcinoma cells via modulation of cyclin kinase inhibitor-cyclin-cyclin- dependent kinase machinery Mol. Cancer Ther. 2004 3 8 933 940 (Pubitemid 39199588)
    • (2004) Molecular Cancer Therapeutics , vol.3 , Issue.8 , pp. 933-940
    • Adhami, V.M.1    Aziz, M.H.2    Reagan-Shaw, S.R.3    Nihal, M.4    Mukhtar, H.5    Ahmad, N.6
  • 32
    • 0025090928 scopus 로고
    • New hydroxylated benzo{c}phenanthridine alkaloids from Eschscholtzia californica cell suspension cultures
    • T. Tanahashi M. H. Zenk New hydroxylated benzo[c]phenanthridine alkaloids from Eschscholtzia californica cell suspension cultures J. Nat. Prod. 1990 53 579 586 (Pubitemid 20311253)
    • (1990) Journal of Natural Products (Lloydia) , vol.53 , Issue.3 , pp. 579-586
    • Tanahashi, T.1    Zenk, M.H.2
  • 33
    • 33746443779 scopus 로고    scopus 로고
    • Analysis of secondary metabolites from Eschscholtzia californica by high-performance liquid chromatography
    • DOI 10.1002/pca.913
    • M. Klvana J. Chen F. Lepine R. Legros M. Jolicoeur Analysis of secondary metabolites from Eschscholtzia californica by high-performance liquid chromatography Phytochem. Anal. 2006 17 4 236 242 (Pubitemid 44122083)
    • (2006) Phytochemical Analysis , vol.17 , Issue.4 , pp. 236-242
    • Klvana, M.1    Chen, J.2    Lepine, F.3    Legros, R.4    Jolicoeur, M.5
  • 34
    • 0035986494 scopus 로고    scopus 로고
    • Identification of Benzophenanthridine alkaloids from Bocconia arborea by gas chromatography-mass spectrometry
    • DOI 10.1002/pca.612
    • R. M. Perez Gutierrez R. Vargas Solis G. Diaz Gutierrez F. J. Martinez-Martinez Identification of benzophenanthridine alkaloids from Bocconia arborea by gas chromatography-mass spectrometry Phytochem. Anal. 2002 13 3 177 180 (Pubitemid 34567858)
    • (2002) Phytochemical Analysis , vol.13 , Issue.3 , pp. 177-180
    • Perez Gutierrez, R.M.1    Vargas Solis, R.2    Diaz Gutierrez, G.3    Martinez-Martinez, F.J.4
  • 35
    • 77956331179 scopus 로고    scopus 로고
    • Shotgun proteomic analysis of yeast-elicited California poppy (Eschscholzia californica) suspension cultures producing enhanced levels of benzophenanthridine alkaloids
    • J. T. Oldham M. Hincapie T. Rejtar P. K. Wall J. E. Carlson C. W. Lee-Parsons Shotgun proteomic analysis of yeast-elicited California poppy (Eschscholzia californica) suspension cultures producing enhanced levels of benzophenanthridine alkaloids J. Proteome Res. 2010 9 9 4337 4345
    • (2010) J. Proteome Res. , vol.9 , Issue.9 , pp. 4337-4345
    • Oldham, J.T.1    Hincapie, M.2    Rejtar, T.3    Wall, P.K.4    Carlson, J.E.5    Lee-Parsons, C.W.6
  • 36
    • 0009714401 scopus 로고    scopus 로고
    • Structural studies of benzophenanthridine alkaloid free bases by NMR spectroscopy
    • DOI 10.1002/mrc.979
    • P. Seckarova R. Marek J. Dostal R. Dommisse E. L. Esmans Structural studies of benzophenanthridine alkaloid free bases by NMR spectroscopy Magn. Reson. Chem. 2002 40 147 152 (Pubitemid 37282063)
    • (2002) Magnetic Resonance in Chemistry , vol.40 , Issue.2 , pp. 147-152
    • Seckarova, P.1    Marek, R.2    Dostal, J.3    Dommisse, R.4    Esmans, E.L.5
  • 37
    • 33847064204 scopus 로고    scopus 로고
    • Isolation and structure elucidation by LC-MS-SPE/NMR: PR toxin- and cuspidatol-related eremophilane sesquiterpenes from Penicillium roqueforti
    • D. Sørensen A. Raditsis L. A. Trimble B. A. Blackwell M. W. Sumarah J. D. Miller Isolation and structure elucidation By LC-MS-SPE/NMR: PR toxin- and cuspidatol-related eremophilane sesquiterpenes from Penicillium roqueforti J. Nat. Prod. 2006 70 1 121 123
    • (2006) J. Nat. Prod. , vol.70 , Issue.1 , pp. 121-123
    • Sørensen, D.1    Raditsis, A.2    Trimble, L.A.3    Blackwell, B.A.4    Sumarah, M.W.5    Miller, J.D.6
  • 38
    • 13244284708 scopus 로고    scopus 로고
    • LC-DAD-MS/SPE-NMR hyphenation. A tool for the analysis of pharmaceutically used plant extracts: Identification of isobaric iridoid glycoside regioisomers from Harpagophytum procumbens
    • DOI 10.1021/ac048772r
    • C. Seger M. Godejohann L.-H. Tseng M. Spraul A. Girtler S. Sturm H. Stuppner LC-DAD-MS/SPE-NMR hyphenation. a tool for the analysis of pharmaceutically used plant extracts: identification of isobaric iridoid glycoside regioisomers from Harpagophytum procumbens Anal. Chem. 2004 77 3 878 885 (Pubitemid 40194152)
    • (2005) Analytical Chemistry , vol.77 , Issue.3 , pp. 878-885
    • Seger, C.1    Godejohann, M.2    Tseng, L.-H.3    Spraul, M.4    Girtler, A.5    Sturm, S.6    Stuppner, H.7
  • 39
    • 77957230553 scopus 로고    scopus 로고
    • Investigation of the experimental limits of small-sample heteronuclear 2D NMR
    • B. D. Hilton G. E. Martin Investigation of the experimental limits of small-sample heteronuclear 2D NMR J. Nat. Prod. 2010 73 9 1465 1469
    • (2010) J. Nat. Prod. , vol.73 , Issue.9 , pp. 1465-1469
    • Hilton, B.D.1    Martin, G.E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.