A new phytoecdysteroid from the stem bark of Vitex cienkowskii
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ORIGINAL PAPER
A new phytoecdysteroid from the stem bark of Vitex cienkowskii Timo D. Stark1 · Julius Rami1 · Sonja Fröhlich1 · Patrick Weiss1 · Wolfgang Vierling2 · Alain B. Dongmo3 · Thomas Hofmann1 Received: 30 April 2020 / Revised: 12 August 2020 / Accepted: 16 August 2020 © The Author(s) 2020
Abstract To investigate differences in the metabolome of the stem bark of Vitex cienkowskii harvested at three different locations and three different seasons, their extracts were analyzed by means of UPLC–ESI–IMS–TOF MSe. One marker metabolite was isolated and chemically characterized, which was identified as the new compound 20,24-dihydroxy,24-hydroxymethylecdysone (1). IMS showed two drift time species for 1 which could be used as new and additional characteristic compound parameters in compound identification to reduce dereplication and false positives. Keywords Non-targeted UPLC–ESI–IMS–TOF–MS profiling · 20,24-Dihydroxy,24-hydroxymethylecdysone · Ion mobility · CCS · Conformers
Introduction About 250 known species of tropical and subtropical trees and shrubs of the genus Vitex are known which belongs to the family of Verbenaceae [1]. Vitex species has been reported to be applied in the traditional medicine to treat a wide range of diseases, such as malaria, asthma, wounds, allergy, depression, venereal and skin diseases, snake bite, and body pain [2]. Cameroonian traditional healers describe Vitex cienkowskii Kotschy and Peyritsch as one of the most popular plants widely used in many disorders. Previous phytochemical studies revealed the identification of diterpenoids [3–6], iridoid glycosides [7, 8], oils [9], flavonoids [6, 10, 11], ceramide [12], and ecdysteroids [7, 13, 14]. Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00217-020-03591-z) contains supplementary material, which is available to authorized users. * Timo D. Stark [email protected] 1
Lehrstuhl für Lebensmittelchemie und Molekulare Sensorik, Technische Universität München, Lise‑Meitner‑Str. 34, 85354 Freising, Germany
2
Institut für Pharmakologie und Toxikologie, Technische Universität München, Biedersteiner Str. 29, 80802 Munich, Germany
3
Department of Animal Biology, Faculty of Science, University of Douala, P.O. Box 24157, Douala, Cameroon
Ultra performance liquid chromatography (UPLC) in combination with Time-of-Flight (TOF) mass spectrometry (MS) is one of the methods of choice for unbiased, fast and sensitive compound screening, fulfills high-throughput demand, and enables the qualification of bioactives and dietary biomarkers with high accuracy [15–18]. MS combined with ion mobility spectrometry (IMS) could resolve ions that may be indistinguishable by MS alone, or to determine structural information like rotationally averaged collision cross-sectional area (CCS). Very recently, we highlighted for several compounds more than one CCS, which we proposed to be hydrogen-bond stabilized rotational isomers in the gas phase. We concluded to use all CCS values of one compound,
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