Isolation and characterization of secondary metabolites from Gaultheria tenuifolia berries

Abstract

Gaultheria berries (Ericaceae) are consumed as food or used in folk medicine throughout the world. In the present study, Gaultheria tenuifolia berries were studied to describe their polyphenol and iridoid composition, aroma volatiles, and cytoprotective effects. In total, 14 metabolites were isolated using a combination of countercurrent chromatography and Sephadex LH‐20, namely, cyanidin‐3‐O‐β‐galactoside, cyanidin‐3‐O‐β‐arabinoside, 3‐O‐caffeoylquinic acid, 5‐O‐caffeoylshikimic acid, quercetin, quercetin‐3‐O‐β‐glucuronide, quercetin‐3‐O‐β‐rutinoside, quercetin‐3‐O‐β‐glucoside, quercetin‐3‐O‐β‐arabinoside, quercetin‐3‐O‐β‐rhamnoside, 6α‐hydroxydihydromonotropein‐10‐trans‐cinnamate, monotropein‐10‐trans‐cinnamate, and an (epi)‐catechin dimer and trimer. Other flavan‐3‐ols, proanthocyanidins, and iridoids were tentatively identified by spectroscopic and spectrometric means in the fruit extracts. The tentative volatile organic compound characterization pointed to methyl salicylate as responsible for the aroma of this species. The extracts showed significant cytoprotective effects in an oxidative stress model in human gastric epithelial cells. This is the first report on the isolation, characterization, and potential biological activity of secondary metabolites from G. tenuifolia berries and insights on its possible application as a functional food. Practical Application Berries are desirable fruit species because of their phytochemical composition and pleasant taste. Gaultheria berries are special due to their high content of iridoids and the presence of salicylic acid derivatives. Aroma of native berries is relevant for the development of new products reflecting the local identity and use of fruits. The present work involves cooperation of academia and industry on the constituents of the native products. The results provided in this article could be useful for the introduction of this species in the food and nutraceutical industries.

UHPLC-MS Chemical Fingerprinting and Antioxidant, Antiproliferative, and Enzyme Inhibition Potential of Gaultheria pumila Berries

“…Peak 5a ( m / z = 493.10559) with a daughter ion at m / z = 301.16412, in agreement with peonidin, was identified as peonidin-3- O -galactoside (C 22 H 23 O 11 + ) [ 21 ]. From Chilean Gaultheria compounds, 1a, 2a, 3a, and 4a were previously identified on G. phillyreifolia [ 11 ], G. poeppigii [ 11 ], and G. antartica [ 14 ], and compounds 3a and 4a in G. tenuifolia berries [ 13 ]. To the best of our knowledge, compound 5a is reported for the first time in G. pumila .…”

“…Iridoids are monoterpenoids previously described in Gaultheria species. Coumaroyl iridoids were predominantly derived from G. poeppigii berries and G. phillyreifolia [ 11 , 12 ], and the secoiridoid Swertiamari and methoxygeniposidic acid, among others, were derived from G. tenuifolia [ 13 ]. Three iridoids were tentatively identified in G. pumila .…”

“…The quantitative and qualitative profiles of phenolic compounds from different colored genotypes of G. poeppigii berries and their antioxidants activities have been evaluated [ 12 ]. Anthocyanins, proanthocyanidins, phenylpropanoids, iridoids, and flavonols have been isolated from G. tenuifolia berries [ 13 ]. The anthocyanin profiles, total anthocyanin content, and antioxidant activities from G. mucronata and G. antarctica have also been described [ 14 ], as well as the flavonols and hydroxycinnamic acid profiles [ 15 ].…”

Advances in metabolic engineering of Corynebacterium glutamicum to produce high-value active ingredients for food, feed, human health, and well-being

“…Corynebacterium glutamicum was also engineered for the synthesis of 6-methylsalicylate (6-MSA), the methyl ester of salicylic acid found in many plant species, particularly wintergreens [101]. Despite applications as a fragrance or flavouring agent, 6-MSA can also be used in high concentrations as an analgesic and rubefacient to treat joint and muscular pain [102].…”