Planta Med 2016; 82(S 01): S1-S381
DOI: 10.1055/s-0036-1596258
Abstracts
Georg Thieme Verlag KG Stuttgart · New York

In silico prediction of UV-Vis spectra for dereplication of natural products extracts

C Audoin
1   Laboratoires Clarins, 5 rue Ampère, 95300 Pontoise, France
,
G Cuvier
1   Laboratoires Clarins, 5 rue Ampère, 95300 Pontoise, France
,
G Genta-Jouve
2   C-TAC, UMR CNRS 8638 COMETE, Université Paris Descartes, 4 avenue de l'observatoire, 75270 Paris, France
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Publikationsdatum:
14. Dezember 2016 (online)

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Identification of known compounds in natural extracts has been empowered in the last decades by the development of several tools such as databases (e.g. the dictionary of natural products [1], mzCloud [2]) and chemoinformatics software (e.g. CSI:FingerID [3], MetFusion [4]). Despite the constant implementation of new compounds in these databases, many compounds are not yet represented. The major drawback of experimental data addition in the current databases is the tremendous cost of standards if existing. Therefore in this study, we present an alternative approach for the creation of an in silico UV-Vis spectra database in order to enhance the dereplication of natural products in plant extracts using both MS and DAD detection. In order to develop the calculation method [5], several (n = 42) compounds belonging to different families (coumarins, flavonoids, polyphenols and alkaloids) were submitted to density functional theory (DFT) using different methods (B3LYP, CAM-B3LYP, B3PW91, MPW1PW91, LSDA) and basis sets (STO-3G, 6 – 31G(d,p), 6 – 31++G(d,p), cc-pVDZ, aug-cc-pVDZ). The best trade off between accuracy and calculation time is then chosen. Correlation between experimental and theoretical spectra was assessed by a linear regression between experimental and predicted λmax for each band for all spectra.

After validation of the method (acquisition, calculation of theoretical spectra and data correction) on available standards, it has been extended to more specific compounds for which experimental data are not available in the lab (e.g. chrysoeriol).

Keywords: UV-Vis spectra, TD-DFT, database, dereplication, natural extracts.

References:

[1] The dictionary of natural products, http://dnp.chemnetbase.com

[2] Advanced Mass Spectral Database, www.mzcloud.org

[3] Dührkop K, Shen H, Meusel M, Rousu J, Böcker S. Searching molecular structure databases with tandem mass spectra using CSI:FingerID. PNAS 2015; 112:12580 – 12585

[4] Gerlich, Neumann S. MetFusion: integration of compound identification strategies. J Mass Spectrom. 2013; 48:291 – 298

[5] Anouar EH, Osman CP, Weber J-FF, Ismail NH. UV/Visible spectra of a series of natural and synthesised anthraquinones: experimental and quantum chemical approaches. Springerplus 2014; 3:233