Bioassay-Guided Isolation of Antioxidant and Cytoprotective Constituents from a Maqui Berry (Aristotelia chilensis) Dietary Supplement Ingredient As Markers for Qualitative and Quantitative Analysis
Abstract:Bioassay-guided phytochemical investigation of a commercially available maqui berry (Aristotelia chilensis) extract used in botanical dietary supplement products led to the isolation of 16 compounds, including one phenolic molecule, 1, discovered for the first time from a natural source, along with several known compounds, 2–16, including three substances not reported previously in A. chilensis, 2, 14, and 15. Each isolate was characterized by detailed analysis of NMR spectroscopic and HRESIMS data, and tested… Show more
“…5 ) and 15 known compounds, were isolated, structurally characterized, and evaluated in the above two bioassays. 105 These isolates included 13 phenolic compounds, two furan derivatives and one organic acid. Interestingly, the new compound, 2- O - β - d -glucopyranosyl-4,6-dihydroxybenzaldehyde ( 23 ), although it had not been previously reported as a natural product, has been generated as a synthetic intermediate for the preparation of anthocyanin, at a time when no spectroscopic data were available.…”
Section: Maqui Berrymentioning
confidence: 99%
“…5 )] as chemical markers, a LC-DAD-MS-based chemical profiling procedure for the utilized maqui berry sample was developed and validated, providing a suitable method for quality control of this dietary supplement ingredient. 105 Fig. 5 Structures of representative compounds isolated from Aristotelia chilensis.…”
In view of the continuous growth of the botanical dietary supplement industry and the increased popularity of lesser known or exotic botanicals, recent findings are described on the phytochemical composition and biological activities of five selected fruits consumed in the United States, namely, açaí, noni, mangosteen, black chokeberry, and maqui berry. A review of the ethnomedicinal uses of these plants has revealed some similarities ranging from wound-healing to the treatment of fever and infectious diseases. Laboratory studies on açaí have shown both its antioxidant and anti-inflammatory activities in vitro, and more importantly, its neuroprotective properties in animals. Anthraquinones and iridoid glucosides isolated from noni fruit induce the phase II enzyme quinone reductase (QR), and noni fruit juice exhibited antitumor and antidiabetic activities in certain animal models. Antitumorigenic effects of mangosteen in animal xenograft models of human cancers have been attributed to its xanthone content, and pure α-mangostin was shown to display antineoplastic activity in mice despite a reported low oral bioavailability. Work on the less extensively investigated black chokeberry and maqui berry has focused on recent isolation studies and has resulted in the identification of bioactive secondary metabolites with QR-inducing and hydroxyl-radical scavenging properties. On the basis of the safety studies and toxicity case reports described herein, these fruits may be generally considered as safe. However, cases of adulteration found in a commercialized açaí product and some conflicting results from mangosteen safety studies warrant further investigation on the safety of these marketed botanical dietary supplements.
“…5 ) and 15 known compounds, were isolated, structurally characterized, and evaluated in the above two bioassays. 105 These isolates included 13 phenolic compounds, two furan derivatives and one organic acid. Interestingly, the new compound, 2- O - β - d -glucopyranosyl-4,6-dihydroxybenzaldehyde ( 23 ), although it had not been previously reported as a natural product, has been generated as a synthetic intermediate for the preparation of anthocyanin, at a time when no spectroscopic data were available.…”
Section: Maqui Berrymentioning
confidence: 99%
“…5 )] as chemical markers, a LC-DAD-MS-based chemical profiling procedure for the utilized maqui berry sample was developed and validated, providing a suitable method for quality control of this dietary supplement ingredient. 105 Fig. 5 Structures of representative compounds isolated from Aristotelia chilensis.…”
In view of the continuous growth of the botanical dietary supplement industry and the increased popularity of lesser known or exotic botanicals, recent findings are described on the phytochemical composition and biological activities of five selected fruits consumed in the United States, namely, açaí, noni, mangosteen, black chokeberry, and maqui berry. A review of the ethnomedicinal uses of these plants has revealed some similarities ranging from wound-healing to the treatment of fever and infectious diseases. Laboratory studies on açaí have shown both its antioxidant and anti-inflammatory activities in vitro, and more importantly, its neuroprotective properties in animals. Anthraquinones and iridoid glucosides isolated from noni fruit induce the phase II enzyme quinone reductase (QR), and noni fruit juice exhibited antitumor and antidiabetic activities in certain animal models. Antitumorigenic effects of mangosteen in animal xenograft models of human cancers have been attributed to its xanthone content, and pure α-mangostin was shown to display antineoplastic activity in mice despite a reported low oral bioavailability. Work on the less extensively investigated black chokeberry and maqui berry has focused on recent isolation studies and has resulted in the identification of bioactive secondary metabolites with QR-inducing and hydroxyl-radical scavenging properties. On the basis of the safety studies and toxicity case reports described herein, these fruits may be generally considered as safe. However, cases of adulteration found in a commercialized açaí product and some conflicting results from mangosteen safety studies warrant further investigation on the safety of these marketed botanical dietary supplements.
“…In some cases, LC/HRMS and NMR dereplication allow identify the bioactive components at this stage, but in most cases, regrowth on a large scale (1-3 L) is needed to have enough quantity of the bioactive compounds, whose structure elucidation is eventually performed using LC-HRMS and nuclear magnetic resonance (NMR) [21]. In the case of NPs from plants or invertebrates, similar bioassay-guided fractionation, dereplication, elucidation and chromatographic purification steps are followed [22,23].…”
Section: Natural Products In Drug Discoverymentioning
Since ancient times, natural products (NPs) have been used as anti-infectives, anti-inflammatories, antioxidants, analgesics and antitumorals and many compounds derived from NPs are in clinical use. The use of plants in traditional medicine for multiple purposes is well known, and throughout recent history, metabolites of microbial origin have had an extraordinary impact on the welfare of humanity. There is an outstanding diversity of chemical structures that nature, and especially microorganisms, are able to produce, due to millenniums of evolution. Since only a small amount of the world's biodiversity has been evaluated for potential biological activity, many more useful natural lead compounds await discovery, the challenge being how to access this natural chemical diversity. However, the validation and selection of primary screening assays, both phenotypic and target-based, are vital to guaranteeing a selection of extracts or molecules with relevant pharmacological action. The screening of antitumor agents against pancreatic cancer (PC) involves the use of established cell lines, cancer stem cells and spheroids that mimic the patient's tumor. Improvements in the discovery of natural products along with the emergence of new technologies in cancer screening assays, promise the discovery of new and valuable drugs to tackle pancreatic cancer in the coming years.
“…Indeed, there is a growing body of scientific literature describing curative effects of fruits against a broad spectrum of diseases including diabetes, obesity, neurodegenerative, gastric and cardiovascular disorders, and certain types of cancers [3][4][5][6]. Different types of secondary metabolites have been reported in fruits [4,[7][8][9]. These compounds are in part responsible for their biological properties.…”
Greigia sphacelata (Ruiz and Pav.) Regel (Bromeliaceae) is a Chilean endemic plant popularly known as “quiscal” and produces an edible fruit consumed by the local Mapuche communities named as “chupón”. In this study, several metabolites including phenolic acids, organic acids, sugar derivatives, catechins, proanthocyanidins, fatty acids, iridoids, coumarins, benzophenone, flavonoids, and terpenes were identified in G. sphacelata fruits using ultrahigh performance liquid chromatography-photodiode array detection coupled with a Orbitrap mass spectrometry (UHPLC-PDA-Orbitrap-MS) analysis for the first time. The fruits showed moderate antioxidant capacities (i.e., 487.11 ± 26.22 μmol TE/g dry weight) in the stable radical DPPH assay, 169.08 ± 9.81 TE/g dry weight in the ferric reducing power assay, 190.32 ± 6.23 TE/g dry weight in the ABTS assay, and 76.46 ± 3.18% inhibition in the superoxide anion scavenging assay. The cholinesterase inhibitory potential was evaluated against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). From the findings, promising results were observed for pulp and seeds. Our findings suggest that G. sphacelata fruits are a rich source of diverse secondary metabolites with antioxidant capacities. In addition, the inhibitory effects against AChE and BChE suggest that natural products or food supplements derived from G. sphacelata fruits are of interest for their neuroprotective potential.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
