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Analysis of epipolythiodioxopiperazines in fungus Chaetomium cochliodes using HPLC-ESI-MS/MS/MS.
Anal Chem. 2008 Jan 01; 80(1):217-26.AC

Abstract

A series of epipolythiodioxopiperazines in the fungus Chaetomium cochliodes was investigated using reversed-phase liquid chromatography with diode array detection and electrospray quadrupole time-of-flight-type tandem mass spectrometry in the positive ion mode. The fragmentation of protonated molecular ions including low-abundance parent ions, [M+H]+ for five known epipolythiodioxopiperazines, dethiotetra(methylthio)chetomin, chaetocochins A-C, and chetomin, was carried out using low-energy collision-induced electrospray ionization tandem spectrometry. It was found that McLafferty rearrangements occurred in the CID processes and produced a complementary pair of characteristic fragment ions containing piperazine rings (fused and unfused), especially to determine the number of S atoms on each ring. The fragmentation differential between [M+H]+ and [M+Na]+ was uncovered. Complementary fragmentation information obtained from [M+H]+ and [M+Na]+ precursor ions is especially valuable for rapid identification of epipolythiodioxopiperazines. A likely known compound, possibly related to chetoseminudin A, and three new species of epipolythiodioxopiperazines from the fungus C. cochliodes were identified or tentatively characterized based on tandem mass spectra of known ones.

Authors+Show Affiliations

Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, People's Republic of China.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

18052340

Citation

Wu, Zhi-Jun, et al. "Analysis of Epipolythiodioxopiperazines in Fungus Chaetomium Cochliodes Using HPLC-ESI-MS/MS/MS." Analytical Chemistry, vol. 80, no. 1, 2008, pp. 217-26.
Wu ZJ, Li GY, Fang DM, et al. Analysis of epipolythiodioxopiperazines in fungus Chaetomium cochliodes using HPLC-ESI-MS/MS/MS. Anal Chem. 2008;80(1):217-26.
Wu, Z. J., Li, G. Y., Fang, D. M., Qi, H. Y., Ren, W. J., & Zhang, G. L. (2008). Analysis of epipolythiodioxopiperazines in fungus Chaetomium cochliodes using HPLC-ESI-MS/MS/MS. Analytical Chemistry, 80(1), 217-26.
Wu ZJ, et al. Analysis of Epipolythiodioxopiperazines in Fungus Chaetomium Cochliodes Using HPLC-ESI-MS/MS/MS. Anal Chem. 2008 Jan 1;80(1):217-26. PubMed PMID: 18052340.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Analysis of epipolythiodioxopiperazines in fungus Chaetomium cochliodes using HPLC-ESI-MS/MS/MS. AU - Wu,Zhi-Jun, AU - Li,Guo-You, AU - Fang,Dong-Mei, AU - Qi,Hua-Yi, AU - Ren,Wei-Jian, AU - Zhang,Guo-Lin, Y1 - 2007/12/06/ PY - 2007/12/7/pubmed PY - 2008/3/28/medline PY - 2007/12/7/entrez SP - 217 EP - 26 JF - Analytical chemistry JO - Anal Chem VL - 80 IS - 1 N2 - A series of epipolythiodioxopiperazines in the fungus Chaetomium cochliodes was investigated using reversed-phase liquid chromatography with diode array detection and electrospray quadrupole time-of-flight-type tandem mass spectrometry in the positive ion mode. The fragmentation of protonated molecular ions including low-abundance parent ions, [M+H]+ for five known epipolythiodioxopiperazines, dethiotetra(methylthio)chetomin, chaetocochins A-C, and chetomin, was carried out using low-energy collision-induced electrospray ionization tandem spectrometry. It was found that McLafferty rearrangements occurred in the CID processes and produced a complementary pair of characteristic fragment ions containing piperazine rings (fused and unfused), especially to determine the number of S atoms on each ring. The fragmentation differential between [M+H]+ and [M+Na]+ was uncovered. Complementary fragmentation information obtained from [M+H]+ and [M+Na]+ precursor ions is especially valuable for rapid identification of epipolythiodioxopiperazines. A likely known compound, possibly related to chetoseminudin A, and three new species of epipolythiodioxopiperazines from the fungus C. cochliodes were identified or tentatively characterized based on tandem mass spectra of known ones. SN - 0003-2700 UR - https://www.unboundmedicine.com/medline/citation/18052340/Analysis_of_epipolythiodioxopiperazines_in_fungus_Chaetomium_cochliodes_using_HPLC_ESI_MS/MS/MS_ L2 - https://doi.org/10.1021/ac071447u DB - PRIME DP - Unbound Medicine ER -