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      Caryophyllene Sesquiterpenes from Pulicaria vulgaris Gaertn.: Isolation, Structure Determination, Bioactivity and Structure-Activity Relationship.

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          Abstract

          A new caryophyllene, named pulicaryenne A (1), along with four other known caryophyllene derivatives (2, 3, 4 and 5) were isolated from the ethyl acetate extract of aerial parts of Pulicaria vulgaris Gaertn. (Asteraceae). All compounds were isolated for the first time from this species. Compound 2 was identified as a new epimer of a known caryophyllene derivative isolated previously from P. dysenterica. Their structures were established by spectroscopic means including NMR analysis (1D- and 2D-NMR) and ESI-TOF-MS. All compounds were evaluated for their anticholinesterase, antityrosinase and cytotoxic activities against two human cell lines (A549 and HeLa). Results showed that compound 5 exhibited the highest cytotoxic effect against A549 and anticholinesterase activity with IC50 values of 8.50±0.75 and 6.45±0.09 μg/mL, respectively. Furthermore, compound 5 showed also an interesting antityrosinase activity with percent inhibition value of 79.0±2.5 % at 50 μg/mL. The bioactivity and drug likeness scores of the isolated compounds 1-5 were calculated using Molinspiration software and discussed. These results may suggest that the five caryophyllene derivatives endowed with good biological properties, which could be used as bioactive alternatives in pharmaceutical preparations.

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          Author and article information

          Journal
          Chem Biodivers
          Chemistry & biodiversity
          Wiley
          1612-1880
          1612-1872
          Feb 2019
          : 16
          : 2
          Affiliations
          [1 ] Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity (LR11ES39), Team: Medicinal Chemistry and Natural Products, Faculty of Science of Monastir, University of Monastir, Avenue of Environment, 5019, Monastir, Tunisia.
          [2 ] Laboratory of Genetics Biodiversity and Valorization of Bioresources (LR11ES41), Higher Institute of Biotechnology of Monastir, University of Monastir, Monastir, Rue Tahar Haddad, 5000, Monastir, Tunisia.
          Article
          10.1002/cbdv.201800483
          30673162
          3d7e0d9c-ae1d-40bb-b42b-6647e50d46aa
          © 2019 Wiley-VHCA AG, Zurich, Switzerland.
          History

          Pulicaria vulgaris,biological activity,caryophyllene derivatives,cytotoxicity

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