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UPLC-Q-TOF-MS/MS analysis of the guaiane sesquiterpenoids oxytropiols A-J and detection of undescribed analogues from the locoweed endophytic fungus Alternaria oxytropis (Pleosporaceae). | LitMetric

UPLC-Q-TOF-MS/MS analysis of the guaiane sesquiterpenoids oxytropiols A-J and detection of undescribed analogues from the locoweed endophytic fungus Alternaria oxytropis (Pleosporaceae).

Phytochem Anal

Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, P. R. China.

Published: April 2022

AI Article Synopsis

  • The study focuses on the locoweed endophytic fungus Alternaria oxytropis, which produces the mycotoxin swainsonine and unique oxygenated bicyclic guaiane sesquiterpenoids, but limited research exists on their mass fragmentation patterns.
  • The researchers used UPLC-Q-TOF-MS/MS techniques to analyze both known compounds, oxytropiols A-J, and to detect new analogues from the fungus's crude extracts.
  • They identified a new sesquiterpenoid analogue called oxytropiol K, demonstrating that UPLC-Q-TOF-MS/MS is effective for discovering and characterizing compounds from organisms with few existing chemical studies.

Article Abstract

Introduction: In addition to the mycotoxin swainsonine, the locoweed endophytic fungus Alternaria oxytropis (Pleosporaceae) also produces a series of rarely reported, highly oxygenated bicyclic guaiane sesquiterpenoids. Few investigations on the electrospray tandem mass fragmentation pattern of this sesquiterpenoid have been reported.

Objectives: We aimed to analyze and detect new guaiane sesquiterpenoid analogues from crude extracts of the locoweed endophytic fungus A. oxytropis by UPLC-Q-TOF-MS/MS experiments.

Materials And Methods: Oxytropiols A-J (1-10) and the extract of the locoweed endophytic fungus A. oxytropis were analyzed by UPLC-Q-TOF-MS/MS in positive mode.

Results: Typical neutral losses, McLafferty rearrangement, 1,2-rearrangement, and 1,3-rearrangement were considered to be the main fragmentation patterns for the [M + H] /[M + Na] ions of 1-10 by UPLC-Q-TOF-MS/MS experiments, and possible fragmentation pathways of 1-10 were suggested. A unique and undescribed analogue named oxytropiol K (11) was found in the extract based on UPLC-Q-TOF-MS/MS analysis. Compound 11 was isolated and elucidated by NMR spectrometry, and its UPLC-Q-TOF-MS/MS analysis was consistent with the fragmentation pathways of 1-10.

Conclusion: The results further support that UPLC-Q-TOF-MS/MS is a powerful and sensitive tool for the characterization of known compounds (dereplication) and the detection of new analogues from crude extracts and imply that the locoweed endophytic fungus A. oxytropis, with few chemical investigations, is an important resource for undescribed metabolites.

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Source
http://dx.doi.org/10.1002/pca.3092DOI Listing

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