메뉴 건너뛰기




Volumn 42, Issue 1, 2007, Pages 70-80

Tandem mass spectrometry of kahalalides: Identification of two new cyclic depsipeptides, kahalalide R and S from Elysia grandifolia

Author keywords

Bryopsis plumosa; Collision induced dissociation; Cyclic depsipeptide; Elysia grandifolia; ESI MS MS; Kahalalide and tandem mass spectrometry

Indexed keywords

BRYOPSIS PLUMOSA; COLLISION-INDUCED DISSOCIATION; CYCLIC DEPSIPEPTIDE; ELYSIA GRANDIFOLIA; ESI-MS/MS;

EID: 33846583499     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1140     Document Type: Article
Times cited : (35)

References (39)
  • 2
    • 0027296890 scopus 로고    scopus 로고
    • Hamann MT, Scheuer PJ. Kahalalide F: a bioactive depsipeptide from the sacoglossan mollusk Elysia rufescens and the alga Bryopsis sp. J. Am. Chem. Soc. 1993; 115: 5825.
    • Hamann MT, Scheuer PJ. Kahalalide F: a bioactive depsipeptide from the sacoglossan mollusk Elysia rufescens and the alga Bryopsis sp. J. Am. Chem. Soc. 1993; 115: 5825.
  • 3
    • 0029842550 scopus 로고    scopus 로고
    • Hamann MT, Otto CS, Scheuer PJ, Dunbar DC. Kahalalides: bioactive peptides from a marine mollusk Elysia rufescens and its algal diet Bryopsis sp. J. Org. Chem. 1996; 61: 6594.
    • Hamann MT, Otto CS, Scheuer PJ, Dunbar DC. Kahalalides: bioactive peptides from a marine mollusk Elysia rufescens and its algal diet Bryopsis sp. J. Org. Chem. 1996; 61: 6594.
  • 4
    • 0030982131 scopus 로고    scopus 로고
    • Two acyclic kahalalides from the sacoglossan mollusk Elysia rufescens
    • Goetz G, Nakao Y, Scheuer PJ. Two acyclic kahalalides from the sacoglossan mollusk Elysia rufescens. J. Nat. Prod. 1997; 60: 562.
    • (1997) J. Nat. Prod , vol.60 , pp. 562
    • Goetz, G.1    Nakao, Y.2    Scheuer, P.J.3
  • 6
    • 0033580898 scopus 로고    scopus 로고
    • The absolute stereochemistry of kahalalide F
    • Goetz G, Yoshida WY, Scheuer PJ. The absolute stereochemistry of kahalalide F. Tetrahedron 1999; 55: 7739.
    • (1999) Tetrahedron , vol.55 , pp. 7739
    • Goetz, G.1    Yoshida, W.Y.2    Scheuer, P.J.3
  • 8
    • 0032822307 scopus 로고    scopus 로고
    • A new cyclic depsipeptide from the hawaiian green alga Bryopsis species
    • Kan Y, Fujita T, Sakiamoto B, Hokama Y, Nagai H. A new cyclic depsipeptide from the hawaiian green alga Bryopsis species. J. Nat. Prod. 1999; 62: 1169.
    • (1999) J. Nat. Prod , vol.62 , pp. 1169
    • Kan, Y.1    Fujita, T.2    Sakiamoto, B.3    Hokama, Y.4    Nagai, H.5
  • 12
    • 33846564151 scopus 로고    scopus 로고
    • Kahalalide F formulation
    • Patent Number US 2004067895
    • Nuyen B, Weitman S, Faircloth GT. Kahalalide F formulation. Patent Number US 2004067895, 2004.
    • (2004)
    • Nuyen, B.1    Weitman, S.2    Faircloth, G.T.3
  • 13
    • 0030053875 scopus 로고    scopus 로고
    • The antitumor compound kahalalide F acts on cell lysosomes
    • Garcia-Rocha M, Bonay P, Avila J. The antitumor compound kahalalide F acts on cell lysosomes. Cancer Lett. 1996; 99: 43.
    • (1996) Cancer Lett , vol.99 , pp. 43
    • Garcia-Rocha, M.1    Bonay, P.2    Avila, J.3
  • 14
    • 0042458241 scopus 로고    scopus 로고
    • A phase I clinical and pharmacokinetic (PK) study with Kahalalide F (KF) in patients (pts) with advanced solid tumours (AST) with a continuous weekly (W) 1-hour iv infusion schedule
    • Ciruelos E, Trigo JM, Pardo B, Paz-Ares L, Estaun N, Cuadra C, Domínguez MJ, Marin A, Ruiz A, Jimeno J, Izquierdo MA. A phase I clinical and pharmacokinetic (PK) study with Kahalalide F (KF) in patients (pts) with advanced solid tumours (AST) with a continuous weekly (W) 1-hour iv infusion schedule. Eur. J. Cancer 2002; 38: S33.
    • (2002) Eur. J. Cancer , vol.38
    • Ciruelos, E.1    Trigo, J.M.2    Pardo, B.3    Paz-Ares, L.4    Estaun, N.5    Cuadra, C.6    Domínguez, M.J.7    Marin, A.8    Ruiz, A.9    Jimeno, J.10    Izquierdo, M.A.11
  • 15
    • 0142227045 scopus 로고    scopus 로고
    • In vitro toxicity of three new antitumoral drugs (Trabectedin, Aplidin and Kahalalide F) on hemotopoietic progenitors and stem cells
    • Gomez SG, Bueren JA, Faireloth GT, Jimeno J, Albella B. In vitro toxicity of three new antitumoral drugs (Trabectedin, Aplidin and Kahalalide F) on hemotopoietic progenitors and stem cells. Exp. Hematol. 2003; 31: 1104.
    • (2003) Exp. Hematol , vol.31 , pp. 1104
    • Gomez, S.G.1    Bueren, J.A.2    Faireloth, G.T.3    Jimeno, J.4    Albella, B.5
  • 17
    • 0024997675 scopus 로고
    • Interactions of lithium ions and dipeptides
    • Grese RP, Gross ML. Interactions of lithium ions and dipeptides. J. Am. Chem. Soc. 1990; 112: 5098.
    • (1990) J. Am. Chem. Soc , vol.112 , pp. 5098
    • Grese, R.P.1    Gross, M.L.2
  • 18
    • 0013619903 scopus 로고
    • Metal ion-peptide interactions in the gas phase: A tandem mass spectrometry study of alkali metal cationized peptides
    • Grese RP, Cerny RL, Gross ML. Metal ion-peptide interactions in the gas phase: a tandem mass spectrometry study of alkali metal cationized peptides. J. Am. Chem. Soc. 1989; 111: 2835.
    • (1989) J. Am. Chem. Soc , vol.111 , pp. 2835
    • Grese, R.P.1    Cerny, R.L.2    Gross, M.L.3
  • 19
    • 0000945360 scopus 로고
    • Location of the alkali metal atom in gas phase peptide complexes
    • Teesch LM, Orlando RC, Adams J. Location of the alkali metal atom in gas phase peptide complexes. J. Am. Chem. Soc. 1991; 113: 3668.
    • (1991) J. Am. Chem. Soc , vol.113 , pp. 3668
    • Teesch, L.M.1    Orlando, R.C.2    Adams, J.3
  • 20
    • 0001642590 scopus 로고
    • Fragmentations of gas-phase complexes between alkali metal atoms and peptides: Metal ion binding to carbonyl oxygens and other neutral functional groups
    • Teesch LM, Adams J. Fragmentations of gas-phase complexes between alkali metal atoms and peptides: metal ion binding to carbonyl oxygens and other neutral functional groups. J. Am. Chem. Soc. 1991; 113: 812.
    • (1991) J. Am. Chem. Soc , vol.113 , pp. 812
    • Teesch, L.M.1    Adams, J.2
  • 21
    • 0022716446 scopus 로고
    • Fast atom bombardment-tandem mass spectrometry studies of alkali-metal ions of small peptides
    • Mallis LM, Russell DH. Fast atom bombardment-tandem mass spectrometry studies of alkali-metal ions of small peptides. Anal. Chem. 1986; 58: 1076.
    • (1986) Anal. Chem , vol.58 , pp. 1076
    • Mallis, L.M.1    Russell, D.H.2
  • 22
    • 0024081973 scopus 로고
    • Fast atom bombardment-tandem mass spectrometry studies of organo-alkali-metal ions of small peptides. Competitive interaction of sodium with basic amino acid substituents
    • Russell DH, McGlohon ES, Mallis LM. Fast atom bombardment-tandem mass spectrometry studies of organo-alkali-metal ions of small peptides. Competitive interaction of sodium with basic amino acid substituents. Anal. Chem. 1988; 60: 1818.
    • (1988) Anal. Chem , vol.60 , pp. 1818
    • Russell, D.H.1    McGlohon, E.S.2    Mallis, L.M.3
  • 23
    • 0024083279 scopus 로고
    • Daughter ion mass spectra from cationized molecules of small oligopeptides in a reflecting time-of-flight mass spectrometer
    • Tang X, Ens W, Standing KG, Westmore JB. Daughter ion mass spectra from cationized molecules of small oligopeptides in a reflecting time-of-flight mass spectrometer. Anal. Chem. 1988; 60: 1791.
    • (1988) Anal. Chem , vol.60 , pp. 1791
    • Tang, X.1    Ens, W.2    Standing, K.G.3    Westmore, J.B.4
  • 24
    • 0034940113 scopus 로고    scopus 로고
    • Sequencing cyclic peptide inhibitors of mammalian ribonucleotide reductase by electospray ionization mass spectrometry
    • Lin S, Liehr S, Cooperman BS, Colter RJ. Sequencing cyclic peptide inhibitors of mammalian ribonucleotide reductase by electospray ionization mass spectrometry. J. Mass Spectrom. 2001; 36: 658.
    • (2001) J. Mass Spectrom , vol.36 , pp. 658
    • Lin, S.1    Liehr, S.2    Cooperman, B.S.3    Colter, R.J.4
  • 25
    • 0000459823 scopus 로고    scopus 로고
    • Sodium-directed selective cleavage of lactones: A method for structure determination of cyclodepsipeptides
    • Ngoka LCM, Gross ML, Peter LT. Sodium-directed selective cleavage of lactones: a method for structure determination of cyclodepsipeptides. Int. J. Mass Spectrom. 1999; 182/183: 289.
    • (1999) Int. J. Mass Spectrom , vol.182-183 , pp. 289
    • Ngoka, L.C.M.1    Gross, M.L.2    Peter, L.T.3
  • 26
    • 0034614305 scopus 로고    scopus 로고
    • Multiple collisionally activated decomposition in an ion trap for the determination of the amino acid sequence and gas phase ion chemistry of lithium-coordinated valinomycin
    • Ngoka LCM, Gross ML, Peter LT. Multiple collisionally activated decomposition in an ion trap for the determination of the amino acid sequence and gas phase ion chemistry of lithium-coordinated valinomycin. Int. J. Mass Spectrom. 2000; 194: 247.
    • (2000) Int. J. Mass Spectrom , vol.194 , pp. 247
    • Ngoka, L.C.M.1    Gross, M.L.2    Peter, L.T.3
  • 27
    • 0036010938 scopus 로고    scopus 로고
    • Mass spectrometric fragmentation of cyclic peptides belonging to the polymyxin and colistin antibiotics studied by ion trap and quadrupole/orthogonal- acceleration time-of-flight technology
    • Govaerts C, Rozenski J, Orwa J, Roets E, Schepdael AV, Hoogmartens J. Mass spectrometric fragmentation of cyclic peptides belonging to the polymyxin and colistin antibiotics studied by ion trap and quadrupole/orthogonal- acceleration time-of-flight technology. Rapid Commun. Mass Spectrom. 2002; 16: 823.
    • (2002) Rapid Commun. Mass Spectrom , vol.16 , pp. 823
    • Govaerts, C.1    Rozenski, J.2    Orwa, J.3    Roets, E.4    Schepdael, A.V.5    Hoogmartens, J.6
  • 28
    • 1542473169 scopus 로고    scopus 로고
    • Hypenation of liquid chromatography to ion trap mass spectrometry to identify minor components in polypeptide antibiotics
    • Govaerts C, Adams E, Schepdael AV. Hypenation of liquid chromatography to ion trap mass spectrometry to identify minor components in polypeptide antibiotics. Anal. Bioanal. Chem. 2003; 377: 909.
    • (2003) Anal. Bioanal. Chem , vol.377 , pp. 909
    • Govaerts, C.1    Adams, E.2    Schepdael, A.V.3
  • 29
    • 0018631894 scopus 로고
    • The identification of depsipeptides by chemical ionisation mass spectroscopy
    • Das BC, Varenne P, Taylor A. The identification of depsipeptides by chemical ionisation mass spectroscopy. J. Antibiot. 1979; 32: 569.
    • (1979) J. Antibiot , vol.32 , pp. 569
    • Das, B.C.1    Varenne, P.2    Taylor, A.3
  • 30
    • 3242699876 scopus 로고    scopus 로고
    • n characterization of protonated cyclic peptides and metal complexes
    • n characterization of protonated cyclic peptides and metal complexes. J. Am. Soc. Mass Spectrom. 2004; 15: 1039.
    • (2004) J. Am. Soc. Mass Spectrom , vol.15 , pp. 1039
    • Williams, S.M.1    Brodbelt, J.S.2
  • 31
    • 0034758877 scopus 로고    scopus 로고
    • Sequencing of new beauverolides by high performance liquid chromatography and mass spectrometry
    • Kuzma M, Jegorov A, Kacer P, Havlicek V. Sequencing of new beauverolides by high performance liquid chromatography and mass spectrometry. J. Mass Spectrom. 2001; 36: 1108.
    • (2001) J. Mass Spectrom , vol.36 , pp. 1108
    • Kuzma, M.1    Jegorov, A.2    Kacer, P.3    Havlicek, V.4
  • 33
    • 0038142335 scopus 로고    scopus 로고
    • Profiling of cyclic hexadepsipeptides roseotoxins synthesized in vitro and in vivo: A combined tandem mass spectrometry and quantum chemical study
    • Jegorov A, Paizs B, Zabka M, Kuzma M, Havlicek V, Giannakopulos AE, Derrick PJ. Profiling of cyclic hexadepsipeptides roseotoxins synthesized in vitro and in vivo: a combined tandem mass spectrometry and quantum chemical study. Eur. J. Mass Spectrom. 2003; 9: 105.
    • (2003) Eur. J. Mass Spectrom , vol.9 , pp. 105
    • Jegorov, A.1    Paizs, B.2    Zabka, M.3    Kuzma, M.4    Havlicek, V.5    Giannakopulos, A.E.6    Derrick, P.J.7
  • 34
    • 84987419408 scopus 로고
    • Proposal for a common nomenclature for sequence ions in mass spectra of peptides
    • Roepstorff P, Fohlman J. Proposal for a common nomenclature for sequence ions in mass spectra of peptides. Biomed. Mass Spectrom. 1984; 11: 601.
    • (1984) Biomed. Mass Spectrom , vol.11 , pp. 601
    • Roepstorff, P.1    Fohlman, J.2
  • 35
    • 0023449998 scopus 로고
    • Novel fragmentation process of peptides by collision-induced decomposition in a tandem mass spectrometer: Differentiation of leucine and isoleucine
    • Johnson RS, Martin SA, Biemann K, Stults JT, Watson JT. Novel fragmentation process of peptides by collision-induced decomposition in a tandem mass spectrometer: differentiation of leucine and isoleucine. Anal. Chem. 1987; 59: 2621.
    • (1987) Anal. Chem , vol.59 , pp. 2621
    • Johnson, R.S.1    Martin, S.A.2    Biemann, K.3    Stults, J.T.4    Watson, J.T.5
  • 36
    • 0029824087 scopus 로고    scopus 로고
    • Effect of alkyl substitution at the amide nitrogen on amide bond cleavage: ESI/SID fragmentation of substance R and two alkylated analogs
    • Nair H, Somogyi A, Wysocki VH. Effect of alkyl substitution at the amide nitrogen on amide bond cleavage: ESI/SID fragmentation of substance R and two alkylated analogs. J. Mass Spectrom. 1996; 31: 1141.
    • (1996) J. Mass Spectrom , vol.31 , pp. 1141
    • Nair, H.1    Somogyi, A.2    Wysocki, V.H.3
  • 37
    • 0036745607 scopus 로고    scopus 로고
    • Quantitative analysis of the novel depsipeptide anticancer drug kahalalide F in human plasma by high-performance liquid chromatography under basic conditions coupled to electrospray ionization tandem mass spectrometry
    • Stokis E, Rosing H, Lopez-Lazaro LL, Rodriguez I, Jimeno JM, Supko JG, Schellens JHM, Beijnen JH. Quantitative analysis of the novel depsipeptide anticancer drug kahalalide F in human plasma by high-performance liquid chromatography under basic conditions coupled to electrospray ionization tandem mass spectrometry. J. Mass Spectrom. 2002; 37: 992.
    • (2002) J. Mass Spectrom , vol.37 , pp. 992
    • Stokis, E.1    Rosing, H.2    Lopez-Lazaro, L.L.3    Rodriguez, I.4    Jimeno, J.M.5    Supko, J.G.6    Schellens, J.H.M.7    Beijnen, J.H.8
  • 38
    • 0034909215 scopus 로고    scopus 로고
    • Quadrupole time-of-flight versus triple-quadrupole mass spectrometry for the determination of phosphopeptides by precursor ion scanning
    • Hanno S, Bernhard K, Matthias M. Quadrupole time-of-flight versus triple-quadrupole mass spectrometry for the determination of phosphopeptides by precursor ion scanning. J. Mass Spectrom. 2001; 36: 782.
    • (2001) J. Mass Spectrom , vol.36 , pp. 782
    • Hanno, S.1    Bernhard, K.2    Matthias, M.3
  • 39
    • 0037697848 scopus 로고    scopus 로고
    • Quadrupole time-of-flight versus triple-quadrupole mass spectrometry for the determination of non-steroidal anti-inflammatory drugs in surface water by liquid chromatography/tandem mass spectrometry
    • Marchese S, Gentill A, Perret D, D'Ascenzo G, Pastori F. Quadrupole time-of-flight versus triple-quadrupole mass spectrometry for the determination of non-steroidal anti-inflammatory drugs in surface water by liquid chromatography/tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2003; 17: 879.
    • (2003) Rapid Commun. Mass Spectrom , vol.17 , pp. 879
    • Marchese, S.1    Gentill, A.2    Perret, D.3    D'Ascenzo, G.4    Pastori, F.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.