Planta Med 2019; 85(18): 1491
DOI: 10.1055/s-0039-3399902
Main Congress Poster
Poster Session 1
© Georg Thieme Verlag KG Stuttgart · New York

LC-MS and NMR guided isolation of monoterpene dimers from cultivated Thymus vulgaris Varico 3 hybrid and their antityrosinase activity

I Stefanis
1   Laboratory of Pharmacognosy, School of Pharmacy, Aristotle University of Thessaloniki, University Campus,, 54124, Thessaloniki, Greece
,
D Hadjipavlou-Litina
2   Department of Pharmaceutical Chemistry, School of Pharmacy, Faculty of Health Sciences,, Thessaloniki, Greece
,
AR Bilia
3   Università degli Studi di Firenze, PHYTOLAB, Departimento di Chimica,, Sesto Fiorentino (Firenze), Italy
,
A Karioti
1   Laboratory of Pharmacognosy, School of Pharmacy, Aristotle University of Thessaloniki, University Campus,, 54124, Thessaloniki, Greece
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Publikationsdatum:
20. Dezember 2019 (online)

 

Thymus vulgaris (Lamiaceae), is an important culinary herb and medicinal plant used for the treatment of productive cough and upper respiratory congestion [1],[2]. Thymus vulgaris L. Varico 3 is a novel hybrid with high yield in essential oil and at least 60% in thymol. As a part of our research program for quality control studies and pharmacological activities on Greek cultivated medicinal plants the chemical investigations on the non volatile constituents of Thymus vulgaris Varico 3 were undertaken. Preliminary analyzes of the leaves revealed the presence of biphenyl constituents, which are known to possess deodorant, antioxidant and antiplatelet activities [3],[4]. These compounds, which are thymol variants, possessing ortho-hydroxyl groups are structurally similar to tyrosinase substrates. Aims of this work were (i) to investigate the biphenyl content of previously unexplored hybrid “Varico 3” and (ii) to test the monoterpene dimers for their antityrosinase activity. Targeted isolation based on a combination of NMR and HPLC-PDA-MS of the dichloromethane extract afforded one new p-cymene dimer (1) together with two known p-cymene derivatives (2, 3), as well as thymol, oleanolic acid, ursolic acid, cirsimaritin and xanthomicrol. The structural elucidation of all compounds was performed by NMR spectroscopic analyses and HRESIMS experiments. The biphenyls were assayed for their inhibitory activity on tyrosinase. Compounds 2 and 3 showed negligible activity, 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).

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Fig. 1
 
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