LC-MS and NMR guided isolation of monoterpene dimers from cultivated Thymus vulgaris Varico 3 hybrid and their antityrosinase activity
| Autor: | Anna Rita Bilia, Ilias Stefanis, Dimitra Hadjipavlou-Litina, Anastasia Karioti |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
Magnetic Resonance Spectroscopy
Stereochemistry Monoterpene Tyrosinase Thymus vulgaris Pharmaceutical Science 01 natural sciences Gas Chromatography-Mass Spectrometry Analytical Chemistry Thymus Plant chemistry.chemical_compound Ursolic acid Drug Discovery Oleanolic Acid Oleanolic acid Thymol Pharmacology biology Monophenol Monooxygenase Plant Extracts 010405 organic chemistry Organic Chemistry Flavones biology.organism_classification Triterpenes 0104 chemical sciences 010404 medicinal & biomolecular chemistry Complementary and alternative medicine chemistry Monoterpenes Molecular Medicine Kojic acid Two-dimensional nuclear magnetic resonance spectroscopy |
| Zdroj: | 67th International Congress and Annual Meeting of the Society for Medicinal Plant and Natural Product Research (GA) in cooperation with the French Society of Pharmacognosy AFERP. |
| ISSN: | 1439-0221 |
| DOI: | 10.1055/s-0039-3399902 |
| Popis: | Targeted isolation based on a combination of NMR and HPLC-PDA-MS of a dichloromethane extract of Thymus vulgaris Varico 3 aerial parts afforded one new p-cymene dimer, 6,3′,4′-trihydroxy-5,5′-diisopropyl-2,2′-dimethylbiphenyl (1), together with two known p-cymene derivatives (2 and 3), as well as five known compounds, namely, thymol (4), oleanolic acid (5), ursolic acid (6), cirsimaritin (7), and xanthomicrol (8). The structural elucidation of all compounds was performed by spectroscopic analyses, including 1D and 2D NMR, and HRESIMS experiments. The biphenyls were assayed for their inhibitory activity on tyrosinase. Compounds 2 and 3 showed negligible activity on tyrosinase, while compound 1 effectively inhibited the enzyme with 35% (± 0.3) inhibitory activity, higher than the inhibition of the reference compound kojic acid (18.6 ± 0.02). |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|