Abstract
The phytochemical profile and anti-inflammatory activity of Gaultheria procumbens dry lipophilic leaf extracts were evaluated. Forty compounds were identified by GC-MS, representing 86.36% and 81.97% of the petroleum ether (PE) and chloroform (CHE) extracts, respectively, with ursolic acid (28.82%), oleanolic acid (10.11%), methyl benzoate (10.03%), and methyl salicylate (6.88%) dominating in CHE, and methyl benzoate (21.59%), docosane (18.86%), and octacosane (11.72%) prevailing in PE. Three components of CHE were fully identified after flash chromatography isolation and spectroscopic studies as (6S,9R)-vomifoliol (4.35%), 8-demethyl-latifolin (1.13%), and 8-demethylsideroxylin (2.25%). Hyaluronidase and lipoxygenase inhibitory activity was tested for CHE (IC50 = 282.15 ± 10.38 μg/mL and 899.97 ± 31.17 μg/mL, respectively), PE (IC50 = 401.82 ± 16.12 μg/mL and 738.49 ± 15.92 μg/mL), and nine of the main constituents versus heparin (IC50 = 366.24 ± 14.72 μg/mL) and indomethacin (IC50 = 92.60 ± 3.71 μg/mL) as positive controls. With the best activity/concentration relationships, ursolic and oleanolic acids were recommended as analytical markers for the extracts and plant material. Seasonal variation of both markers following foliar development was investigated by UHPLC-PDA. The highest levels of ursolic (5.36–5.87 mg/g DW of the leaves) and oleanolic (1.14–1.26 mg/g DW) acids were observed between August and October, indicating the optimal season for harvesting.
Highlights
Gaultheria procumbens L. is a small, low-growing, evergreen shrub native to northeastern North America and widely cultivated all through the Northern Hemisphere due to its ornamental and medicinal value
Our previous studies [7] demonstrated that the anti-inflammatory activity of wintergreen leaves is largely influenced by other polar compounds, among which thirty-five representatives of flavonoids, proanthocyanidins, and caffeoylquinic acids were identified by UHPLC-photodiode array detector (PDA)-ESI-MS3 profiling
The qualitative characteristics of the wintergreen leaf lipophilic compounds were evaluated by GC-MS analysis of the dry petroleum ether (PE) and chloroform (CHE) extracts after trimethylsilyl derivatization
Summary
Gaultheria procumbens L. (eastern teaberry, checkerberry, American wintergreen, Ericaceae) is a small, low-growing, evergreen shrub native to northeastern North America and widely cultivated all through the Northern Hemisphere due to its ornamental and medicinal value. 95% of the essential oil [2], and its glycosidic precursor—gaultherin [3]—are the main representatives of salicylates, so far considered as the primary active constituents of Gaultheria plants [4,5,6]. Our previous studies [7] demonstrated that the anti-inflammatory activity of wintergreen leaves is largely influenced by other polar compounds, among which thirty-five representatives of flavonoids, proanthocyanidins, and caffeoylquinic acids were identified by UHPLC-PDA-ESI-MS3 profiling. The concept of metabolite profiling evolved recently in the most preferable characterization procedure of bioactive plant fractions, but it is generally confined to hydrophilic compounds alone [8], while lipophilic components are often studied only fragmentarily, either by classic techniques such as isolation, or after separation of less complex, specific sub-fractions, e.g., essential oils. More selective methods (GC-MS) have so far been used only for identification of long-chain aliphatic alkanes
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