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Planta Med 2019; 85(11/12): 941-946
DOI: 10.1055/a-0927-7041
Biological and Pharmacological Activities
Original Papers
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

Ilias Stefanis
1   Laboratory of Pharmacognosy, School of Pharmacy, Aristotle University of Thessaloniki, Thessaloniki, Greece
,
Dimitra Hadjipavlou-Litina
2   Department of Pharmaceutical Chemistry, School of Pharmacy, Faculty of Health Sciences, Thessaloniki, Greece
,
Anna-Rita Bilia
3   University of Florence, PHYTOLAB, Department of Chemistry Ugo Schiff, Florence, Italy
,
Anastasia Karioti
1   Laboratory of Pharmacognosy, School of Pharmacy, Aristotle University of Thessaloniki, Thessaloniki, Greece
› Author Affiliations
Further Information

Publication History

received 30 January 2019
revised 06 May 2019

accepted 10 May 2019

Publication Date:
04 June 2019 (online)

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Abstract

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).

Key words

Thymus vulgaris Varico 3 - Lamiaceae - p-cymene derivatives - monoterpene dimers - tyrosinase

Supporting Information

    The spectral data of compound 1 and UV-ESI-MS data of compounds present in the chromatogram of T. vulgaris Varico 3 are available as Supporting Information.

  • Supporting Information
 

  • References

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