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. 2017 Jan 22;22(1):174.
doi: 10.3390/molecules22010174.

A Method for LC-MS/MS Profiling of Coumarins in Zanthoxylum zanthoxyloides (Lam.) B. Zepernich and Timler Extracts and Essential Oils

Affiliations

A Method for LC-MS/MS Profiling of Coumarins in Zanthoxylum zanthoxyloides (Lam.) B. Zepernich and Timler Extracts and Essential Oils

Yoro Tine et al. Molecules. .

Abstract

The metabolites from the coumarin class, present in tissues of plants belonging mainly to the Rutaceae and Apiaceae families, included compounds with high chemical diversity such as simple coumarins and furocoumarins. These health-promoting components are recognized for their valuable biological activities in herbal preparations but also for their phototoxic effects. In this work, a targeted liquid chromatography (LC) coupled with tandem mass spectrometry (MS²) was developed for the screening of 39 reference standards of coumarins and furocoumarins in essential oils and plant extracts. Chromatographic separation was accomplished on reversed phase column using water/acetonitrile as the mobile phase and detection was performed on a hybrid QqQ/linear ion trap spectrometer fitted with an atmospheric pressure chemical ionization (APCI) source operating in positive ion mode. This analytical approach was applied to investigate the coumarin compositions of fruit essential oils and methanolic extracts obtained from separated parts (fruit, leaf, stem, trunk, and root) of Zanthoxylum zanthoxyloides. Ten coumarins and six furanocoumarins were reported in this species and data analyses were used to assess the suitability of these compounds to the metabolomics-based differentiation of plant organs. The quantification criteria of the metabolites in extract samples included linearity, limit of quantification, limit of detection, and matrix effect were validated. As reported for other species of the Rutaceae family, the concentration of coumarins was drastically higher in Z. zanthoxyloides fruits than in other plant organs.

Keywords: LC-APCI-MS/MS; Zanthoxylum zanthoxyloides; coumarins; essential oil.

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Conflict of interest statement

These authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Enhanced product ion (EPI) mass spectrum of xanthotoxin with the atmospheric pressure chemical ionization (APCI) source in positive ion mode.
Figure 2
Figure 2
Chemical structures of coumarins (110) and furocoumarins (1116) of Z. zanthoxyloides samples.
Figure 3
Figure 3
(a) Scores plot of principal component analysis and discriminant analysis (PCA-DA) of the Z. zanthoxyloides extracts (fruit, leaf, stem, root, trunk) and fruit essential oils analyzed using LC-MS/MS in the MRM mode; (b) Scores plot of PCA-DA of coumarins and furocoumarins detected in Z. zanthoxyloides samples using LC-MS/MS in the MRM mode.
Figure 3
Figure 3
(a) Scores plot of principal component analysis and discriminant analysis (PCA-DA) of the Z. zanthoxyloides extracts (fruit, leaf, stem, root, trunk) and fruit essential oils analyzed using LC-MS/MS in the MRM mode; (b) Scores plot of PCA-DA of coumarins and furocoumarins detected in Z. zanthoxyloides samples using LC-MS/MS in the MRM mode.

References

    1. Miyake Y., Murakami A., Sugiyama Y., Isobe M., Koshimizu K., Ohigashi H. Identification of coumarins from lemon fruit (Citrus limon) as inhibitors of in vitro tumor promotion and superoxide and nitric oxide generation. J. Agric. Food Chem. 1999;47:3151–3157. doi: 10.1021/jf980999y. - DOI - PubMed
    1. Dugrand A., Olry A., Duval T., Hehn A., Froelicher Y., Bourgaud F. Coumarin and Furanocoumarin Quantitation in Citrus Peel via Ultraperformance Liquid Chromatography Coupled with Mass Spectrometry (UPLC-MS) J. Agric. Food Chem. 2013;61:10677–10684. doi: 10.1021/jf402763t. - DOI - PubMed
    1. Frérot E., Decorzant E. Quantification of Total Furocoumarins in Citrus Oils by HPLC Coupled with UV, Fluorescence, and Mass Detection. J. Agric. Food Chem. 2004;52:6879–6886. doi: 10.1021/jf040164p. - DOI - PubMed
    1. Peroutka R., Schulzová V., Botek P., Hajšlová J. Analysis of furanocoumarins in vegetables (Apiaceae) and Citrus fruits (Rutaceae) J. Sci. Food Agric. 2007;87:2152–2163. doi: 10.1002/jsfa.2979. - DOI
    1. Rios M.Y. Terpenes, Coumarins, and Flavones from Acacia pennatula. Chem. Nat. Compd. 2005;41:297–298. doi: 10.1007/s10600-005-0133-8. - DOI

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