Planta Med 2015; 81 - PW_177
DOI: 10.1055/s-0035-1565801

UHPLC-QTOF-MS as a valuable tool for the identification of novel faradiol fatty acid diesters of Calendula officinalis flowers

C Nicolaus 1, A Sievers-Engler 2, R Murillo 3, M Lämmerhofer 2, I Merfort 1
  • 1Institute of Pharmaceutical Sciences, Department of Pharmaceutical Biology and Biotechnology, University of Freiburg, Freiburg, Germany
  • 2Institute of Pharmaceutical Sciences, Department of Pharmaceutical Chemistry, University of Tübingen, Tübingen, Germany
  • 3Escuela de Quimica and CIPRONA, Universidad de Costa Rica, San Jose, Costa Rica

Calendula officinalis L. (marigold) flower extracts are recommended for the treatment of minor inflammation of the skin and wounds [1]. Triterpenes from the 20-taraxastene type, especially faradiol seem to be crucial for the anti-inflammatory potential [2, 3]. Besides monols triterpene diols and triols are present in the form of their C3 lauric, myristic and palmitic acid monoesters. Here we report on the isolation of a mixture of novel faradiol fatty acid diesters (20-taraxastene 3β,16β-diester). 1D and 2D NMR analysis revealed the triterpene skeleton and the esterification position. However, only after UHPLC-QTOF-MS analysis the fatty acids could be identified and assigned to the respective triterpene. This method allowed identification of intact [M+H+]+ molecular ion peaks of faradioldimyristate (863.7354 m/z), faradioldipalmitate (919.8302 m/z) and faradiolmyristate, palmitate (891.7633 m/z). Moreover, this technique is also suitable for the separation and identification of the arnitriol A 3- and the lupane-3β,16β,20-triol 3-fatty acid monoesters which is here reported for Calendula officinalis L. flowers for the first time.

Acknowledgements: We are grateful to S. Ferlaino, Department for Pharmaceutical and Medical Chemistry, University of Freiburg, Germany for measuring the NMR spectra and to Dr. Junghanns for providing us with Calendula flowers.

References:

[1] HMPC. Assesment report for the development of community herbal monographs and for inclusion of herbal substance(s), preparation(s) or combination thereof in the community list-Calendula officinalis L., flos. EMEA 2008

[2] Della Loggia R et al. The role of triterpenoids in the topical anti-inflammatory activity of Calendula officinalis flowers. Planta Med 1994; 60: 516 – 520

[3] Neukirch H et al. Improved anti-Inflammatory activity of three new terpenoids derived, by systematic chemical modifications, from the abundant triterpenes of the flowery plant Calendula officinalis. Chem Biodivers 2005; 2: 657 – 671