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Electrospray ionization tandem mass spectrometry of chaetoglobosins.
Rapid Commun Mass Spectrom. 2012 Sep 30; 26(18):2115-22.RC

Abstract

RATIONALE

Chaetoglobosins are a family of macrocyclic polyketide alkaloids. They possess many similar isomers and exhibit a wide range of biological activities. Thus, there is a need for reliable, fast, and low-cost analysis of this class of compounds.

METHODS

A series of seven chaetoglobosins from Chaetomium globosum, including two types of isomers, were investigated using electrospray ionization quadrupole time-of-flight tandem mass spectrometry (ESI-QTOF-MS/MS) in both positive- and negative-ion mode. The identity of major product ions was supported by deuterium-labeling experiments.

RESULTS

In positive-ion mode, the product ion at m/z 130 is the characteristic ion of the indolyl group. A McLafferty rearrangement might play a significant role in the fragmentation of the macrocycle moiety for most chaetoglobosins and produces two series of characteristic product ions, accompanied by neutral losses. The characteristic product ion at m/z 309 in the MS/MS spectrum of chaetoglobosins E indicates the structure of the cyclic olefinic bond in ring B and can be used to distinguish it from the isomers, chaetoglobosins F(ex) , which has an exocyclic double bond on ring B. In negative-ion mode, the McLafferty rearrangement has an important role in the fragmentation pattern of the macrocycle. Some high-abundance radical ions were detected. The radical product ion at m/z 138 might differentiate chaetoglobosins F and penochalasin F, isomers which have very similar structures.

CONCLUSIONS

In summary, complementary information obtained from fragmentation experiments of [M+H](+) and [M-H](-) precursor ions is especially valuable for rapid identification of chaetoglobosins. The high-abundance radical ions in negative-ion mode are also of scientific interest.

Authors+Show Affiliations

Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, P.R. China.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

22886807

Citation

Xu, Guo-Bo, et al. "Electrospray Ionization Tandem Mass Spectrometry of Chaetoglobosins." Rapid Communications in Mass Spectrometry : RCM, vol. 26, no. 18, 2012, pp. 2115-22.
Xu GB, Li LM, Fang DM, et al. Electrospray ionization tandem mass spectrometry of chaetoglobosins. Rapid Commun Mass Spectrom. 2012;26(18):2115-22.
Xu, G. B., Li, L. M., Fang, D. M., Li, G. Y., Zhang, G. L., & Wu, Z. J. (2012). Electrospray ionization tandem mass spectrometry of chaetoglobosins. Rapid Communications in Mass Spectrometry : RCM, 26(18), 2115-22. https://doi.org/10.1002/rcm.6329
Xu GB, et al. Electrospray Ionization Tandem Mass Spectrometry of Chaetoglobosins. Rapid Commun Mass Spectrom. 2012 Sep 30;26(18):2115-22. PubMed PMID: 22886807.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Electrospray ionization tandem mass spectrometry of chaetoglobosins. AU - Xu,Guo-Bo, AU - Li,Li-Mei, AU - Fang,Dong-Mei, AU - Li,Guo-You, AU - Zhang,Guo-Lin, AU - Wu,Zhi-Jun, PY - 2012/8/14/entrez PY - 2012/8/14/pubmed PY - 2012/10/24/medline SP - 2115 EP - 22 JF - Rapid communications in mass spectrometry : RCM JO - Rapid Commun Mass Spectrom VL - 26 IS - 18 N2 - RATIONALE: Chaetoglobosins are a family of macrocyclic polyketide alkaloids. They possess many similar isomers and exhibit a wide range of biological activities. Thus, there is a need for reliable, fast, and low-cost analysis of this class of compounds. METHODS: A series of seven chaetoglobosins from Chaetomium globosum, including two types of isomers, were investigated using electrospray ionization quadrupole time-of-flight tandem mass spectrometry (ESI-QTOF-MS/MS) in both positive- and negative-ion mode. The identity of major product ions was supported by deuterium-labeling experiments. RESULTS: In positive-ion mode, the product ion at m/z 130 is the characteristic ion of the indolyl group. A McLafferty rearrangement might play a significant role in the fragmentation of the macrocycle moiety for most chaetoglobosins and produces two series of characteristic product ions, accompanied by neutral losses. The characteristic product ion at m/z 309 in the MS/MS spectrum of chaetoglobosins E indicates the structure of the cyclic olefinic bond in ring B and can be used to distinguish it from the isomers, chaetoglobosins F(ex) , which has an exocyclic double bond on ring B. In negative-ion mode, the McLafferty rearrangement has an important role in the fragmentation pattern of the macrocycle. Some high-abundance radical ions were detected. The radical product ion at m/z 138 might differentiate chaetoglobosins F and penochalasin F, isomers which have very similar structures. CONCLUSIONS: In summary, complementary information obtained from fragmentation experiments of [M+H](+) and [M-H](-) precursor ions is especially valuable for rapid identification of chaetoglobosins. The high-abundance radical ions in negative-ion mode are also of scientific interest. SN - 1097-0231 UR - https://www.unboundmedicine.com/medline/citation/22886807/Electrospray_ionization_tandem_mass_spectrometry_of_chaetoglobosins_ L2 - https://doi.org/10.1002/rcm.6329 DB - PRIME DP - Unbound Medicine ER -