The Volatile Phytochemistry of Seven Native American Aromatic Medicinal Plants

As part of our evaluation of essential oils derived from Native American medicinal plants, we have obtained the essential oils of Agastache foeniculum (Pursch) Kuntze (Lamiaceae), Gaultheria procumbens L. (Ericaceae), Heliopsis helianthoides (L.) Sweet (Asteraceae), Liatris spicata (L.) Willd. (Asteraceae), Pycnanthemum incanum (L.) Michx. (Lamiaceae), Smallanthus uvedalia (L.) Mack. ex Mack. (Asteraceae), and Verbena hastata L. (Verbenaceae) by hydrodistillation. The essential oils were analyzed by gas chromatographic techniques. The essential oil of A. foeniculum was dominated by estragole (88–93%), while methyl salicylate (91%) dominated the G. procumbens essential oil. Germacrene D was the major component in H. helianthoides (42%) and L. spicata (24%). 1,8-Cineole (31%) and α-terpineol (17%) were the main compounds in P. incanum essential oil. The essential oil of S. uvedalia showed α-pinene (24%), perillene (15%), and β-caryophyllene (17%) as major components. Verbena hastata essential oil was rich in 1-octen-3-ol (up to 29%) and palmitic acid (up to 22%). Four of these essential oils, H. helianthoides, L. spicata, P. incanum, and V. hastata, are reported for the first time. Additionally, the enantiomeric distributions of several terpenoid components have been determined.

Floristic Changes in the Understory Vegetation of Mixed Temperate New England Freshwater Island Forests over a Period of 33 Years

During a 33-year sampling period, we observed species richness and calculated species evenness and Shannon Diversity for understory woody seedlings and herbaceous species on three small islands in Lake Winnipesaukee, New Hampshire, and noted consistency of dominant plant species over time. Seedlings and herbaceous species were recorded and measured in 25 permanent plots that were created on the three islands in 1978. The understory species data were compiled by frequency and dominance of woody seedlings and herbaceous species. Data from 250 individual quadrats show that species richness more than doubled from 41 in 1978 to 83 species on all three islands in 2011. Species evenness on all the islands remained relatively constant in each of the four samplings. The combined Shannon’s Diversity for the three islands rose from 2.76 in 1978 to 3.37 in 2011. Dominant species in the study were Aralia nudicaulis, Gaultheria procumbens, Gaylussacia baccata, Maianthemum canadense, and Tsuga canadensis seedlings.

Biological and chemical insight into Gaultheria procumbens fruits: a rich source of anti-inflammatory and antioxidant salicylate glycosides and procyanidins for food and functional application

The fruits of Gaultheria procumbens are the richest known dietary source of salicylates with confirmed anti-inflammatory potential.

Methyl Salicylate Glycosides in Some Italian Varietal Wines

Glycosides are ubiquitous plant secondary metabolites consisting of a non-sugar component called an aglycone, attached to one or more sugars. One of the most interesting aglycones in grapes and wine is methyl salicylate (MeSA), an organic ester naturally produced by many plants, particularly wintergreens. To date, nine different MeSA glycosides from plants have been reported, mainly spread over the genera Gaultheria, Camellia, Polygala, Filipendula, and Passiflora. From a sensorial point of view, MeSA has a balsamic-sweet odor, known as Wintergreen. MeSA was found in Vitis riparia grapes, in Vitis vinifera sp. and in the Frontenac interspecific hybrid. We found that the MeSA glycosides content in Verdicchio wines and in some genetically related varieties (Trebbiano di Soave and Trebbiano di Lugana) was very high. In order to understand which glycosides were present in wine, the methanolic extract of Verdicchio wine was injected into a UPLC-Q-TOF-HDMS and compared to the extracts of different plants rich in such glycosides. Using pure standards, we confirmed the existence of two glycosides in wine: MeSA 2-O--d-glucoside and MeSA 2-O--d-xylopyranosyl (1-6) -d-glucopyranoside (gaultherin). For the first time, we also tentatively identified other diglycosides in wine: MeSA 2-O--l-arabinopyranosyl (1-6)--d-glucopyranoside (violutoside) and MeSA 2-O--d-apiofuranosyl (1-6)--d-glucopyranoside (canthoside A), MeSA 2-O--d-glucopyranosyl (1-6)-O--d-glucopyranoside (gentiobioside) and MeSA 2-O--l-rhamnopyranosyl (1-6)--d-glucopyranoside (rutinoside). Some of these glycosides have been isolated from Gaultheria procumbens leaves by preparative liquid chromatography and structurally annotated by 1H- and 13C-NMR analysis. Two of the peaks isolated from Gaultheria procumbens leaves, namely MeSA sambubioside and MeSA sophoroside, were herein observed for the first time. Six MeSA glycosides were quantified in 64 Italian white wines, highlighting the peculiar content and pattern in Verdicchio wines and related cultivars. The total concentration in bound and free MeSA in Verdicchio wines varied in the range of 456–9796 g/L and 5.5–143 g/L, respectively, while in the other wines the bound and free MeSA was below 363 g/L and 12 g/L, respectively. As this compound’s olfactory threshold is between 50 and 100 g/L, our data support the hypothesis that methyl salicylate can contribute to the balsamic scent, especially in old Verdicchio wines.

Salicylate and Procyanidin-Rich Stem Extracts of Gaultheria procumbens L. Inhibit Pro-Inflammatory Enzymes and Suppress Pro-Inflammatory and Pro-Oxidant Functions of Human Neutrophils Ex Vivo

Salicylate-rich plants are an attractive alternative to synthetic anti-inflammatory drugs due to a better safety profile and the advantage of complementary anti-inflammatory and antioxidant effects of the co-occurring non-salicylate phytochemicals. Here, the phytochemical value and biological effects in vitro and ex vivo of the stems of one of such plants, Gaultheria procumbens L., were evaluated. The best extrahent for effective recovery of the active stem molecules was established in comparative studies of five extracts. The UHPLC-PDA-ESI-MS3, HPLC-PDA, and UV-photometric assays revealed that the selected acetone extract (AE) accumulates a rich polyphenolic fraction (35 identified constituents; total content 427.2 mg/g dw), mainly flavanols (catechins and proanthocyanidins; 201.3 mg/g dw) and methyl salicylate glycosides (199.9 mg/g dw). The extract and its model components were effective cyclooxygenase-2, lipoxygenase, and hyaluronidase inhibitors; exhibited strong antioxidant capacity in six non-cellular in vitro models (AE and procyanidins); and also significantly and dose-dependently reduced the levels of reactive oxygen species (ROS), and the release of cytokines (IL-1β, IL-8, TNF-α) and proteinases (elastase-2, metalloproteinase-9) in human neutrophils stimulated ex vivo by lipopolysaccharide (LPS) and N-formyl-L-methionyl-L-leucyl-L-phenylalanine (fMLP). The cellular safety of AE was demonstrated by flow cytometry. The results support the application of the plant in traditional medicine and encourage the use of AE for development of new therapeutic agents.

A RAPID QUANTITATIVE DYE-BINDING METHOD OF SCREENING GLYCOSAMINOGLYCANS PRESENCE IN MEDICINAL PLANTS

Objectives: The aims of this paper are to extract glycosaminoglycan (GAG) from four local medicinal plants and to characterize the crude extract with highest total sulfated GAG to reduce the dependency of using animals as major sources.Methods: Crude GAG was extracted from four plants (Gaultheria procumbens, Strobilanthes crispus, Orthosiphon stamineus, and Ficus deltoidea) using hot water extraction with some modifications. Ultraviolet (UV) spectrophotometry was conducted for purity test. Total sulfated GAG was determined using Blyscan assay kit. By comparing results between the extract yields and total sulfated GAG, the plant consisting of high total sulfated GAG was chosen for further characterization. The selected plant sample was examined by microscopy and further analyzed by nuclear magnetic resonance (NMR) and Fourier-transform infrared (FTIR) spectroscopy.Results: All four plants showed absorbance peaks between 214 and 232 nm in UV scan that represented negatively charged sugar. O. stamineus was found to contain the highest amount of sulfated GAG, 62.63±0.01 μg/mg by Blyscan assay. Microscopical examination confirmed the identity of O. stamineus sample by comparing to the reference. Both NMR and FTIR analysis of O. stamineus crude yield showed the presence of hydroxyl, sulfates, carboxylate, and amine groups, suggesting close resemblances to GAG structure.Conclusion: The results suggested that all four plants contained GAG compound. O. stamineus was found to exhibit the most abundant total sulfated GAG and has the potential to become a new plant-based source for GAG.