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MTQ ,2-DHTI UA OA Ebrahim Azadniya and Gertrud Morlock

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Presentation on theme: "MTQ ,2-DHTI UA OA Ebrahim Azadniya and Gertrud Morlock"— Presentation transcript:

1 HPTLC-EDA-HRMS and PLC-NMR to reveal co-eluting isomers of bioactive zones
MTQ ,2-DHTI UA OA Ebrahim Azadniya and Gertrud Morlock Justus Liebig University Giessen

2 1) Unknown bioactive zone in Danshen extract
HPTLC-EDA P-68 Standards Extract

3 Separation of tanshinones by RP-HPLC
5 UN 6 MTQ 7 Danshenxinkun m/z 303 [M+Na]+ 8 TIIA J. Chromatogr. A 925 (2001) 109–114 J. Chromatogr. A 945 (2002) 281–285 J. Agric. Food Chem. 56 (2008) 1164–1171 5 TI 6 Sugiol 7 1,2-DHTI 8 MTQ 9 TIIA Neo-przewaquinone A (C36H28O6) = MTQ (C18H14O3) + 1,2-DHTI (C18H14O3) 4 TI 5 Neo-przewaquinone A 6 TIIA J. Chromatogr. B 879 (2011) 1899–1904

4 HPTLC-HRMS for unknown bioactive zone x
TIIA TI CT 15, 17 DHTI R2C=CHR, R2C=CH2 Vinylic proton 4.6 – 5.7 1,2-dihydrotanshinone (1,2-DHTI) Methylenetanshinquinone (MTQ) Isodihydrotanshinone I Isodihydrotanshinone II

5 PLC-NMR spectroscopy workflow
2 mL of 200 mg/mL sample TIIA TI DHTI CT

6 2) Bioactive zone in Lamiaceae & apple peel extracts
UA OA A B C D

7 HPTLC-ESI-HRMS of UA and OA
[M+Na]+ [M-H+2Na]+ [M-H]- UA OA Positive mode Negative mode

8 Quantification of UA and OA with qNMR
Maleic acid PLC-1HNMR spectra of Oregano H18 UA H18 OA 1 mL oregano extract (10 mg/mL) and 50 µL maleic acid (2 mg/mL) 1HNMR spectra of mix UA:OA (1:1) Maleic acid PLC-1HNMR spectra of Oregano 1HNMR spectra of Oregano extract

9 qHPTLC after pre- and post-derivatization
Pre-derivatization: iodine solution Post-derivatization: anisaldehyde sulfuric acid reagent Sample names Standards Content (mg/g, dried extract) Content (g/100 g, dried sample ) Salvia officinalis UA 193.7 1.8 OA 95.5 0.9 Origanum vulgare 32.3 0.2 10.1 0.1 Thymus vulgaris 173.8 1.0 67.8 0.4 Red apple peel 238.5 1.9 58.0 0.5 Green apple peel 205.6 1.3 50.2 0.3 Sample name Standards q-HPTLC q-NMR Origanum vulgare UA 32.3 32.6 OA 10.1 11.1

10 Wrap up PLC-NMR spectroscopy more appropriate procedure than isolation of active compound by a TLC-MS interface PLC-NMR as tool for quantification of compounds, which are hardly possible to be quantified by qNMR Instead of column chromatography and bioactivity-guided fractionation → HPTLC-EDA-HRMS and PLC-NMR 2 mL of 200 mg/mL sample TIIA TI DHTI CT ˃˃˃ Maleic acid PLC-1HNMR spectra of Oregano 1HNMR spectra of Oregano extract

11 Thank you


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