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Abstract: Four isoflavones were isolated from the MeOH extract of a sample of Azorella madreporica from the high Andes of northern Chile by selective fractionation using the bleaching of the DPPH radical. The compounds were identified by NMR spectroscopy and mass spectrometry together with 18 additional complex isoflavones present in the plant extract which were detected for the first time using HPLC hyphenated with UV–visible and high resolution mass detectors (HR-PDA-ToF-ESI-MS). The results obtained showed that the methodology developed is appropriate for rapid analysis and identification of isoflavones in extracts from native A. madreporica which can have potential use as an additive for food, or as a nutritional supplement due to the high content on isoflavones (yield of 162.98, 290.18, 44.25 and 31.03mg/kg dry plant for the isolated compounds genistein-8-C-β-d-glucopyranoside (1), alpinum isoflavone (19), angustone C (21) and 4´-acetyl-alpinum isoflavone, 22, respectively). The latter compound 22 is a new isoflavone derivative isolated for the first time from a plant source. The moderate antioxidant properties and content of isoflavonoids found in the aerial parts can explain, at least in part, the traditional use of the native plant and health benefits of the infusions. [Copyright &y& Elsevier]

Plants in the genus Hypericum (Hypericaceae), include more than 500 species worldwide, and many are valued for their medicinal properties, and are used as traditional herbal medicines. However, only H. perforatum is officially recognized as herbal drug in several pharmacopoeias, and used as an antidepressant clinically. Hypericum perforatum had been used as an herbal medicine since the Han Dynasty (206 B.C. -220 A.D.) in China. It taxonomically belongs to the section Hypericum in the genus Hypericum. There are about 42 species in the section Hypericum , with six species occurring in China. All six are recorded as traditional herbal medicines for treating aliments, including hepatitis, malaria, traumatic hemorrhage, irregular menstruation, wounds, and bruises. The study aimed to characterize the chemical profiles of five phylogenetically related Hypericum species, and compare their metabolites with three H. perforatum products. Informed by ethnobotanical use, the extracts prepared from the five species were further investigated into anticancer, anti-inflammatory and antiplasmodial activity. This study tested the hypothesis that systematic metabolomic and bioactivity characterization of species in section Hypericum will help to validate their phytotherapeutic use and reveal potential drug lead compounds. Targeted and non-targeted metabolic analyses coupled with chemometrics were conducted on H. perforatum and four medicinal species, H. attenuatum , H. enshiense , H. erectum , and H. faberi , native to China from section Hypericum. UPLC-QTOF-MS/MS and UPLC-TQD-MS/MS were used for non-targeted and targeted metabolic analyses, respectively. Cytotoxicity bioassays on four cancer cell lines, anti-inflammation tests and anti-plasmodial activity on Plasmodium falciparum 3D7, selected based on traditional medicinal use, were evaluated on extracts from Hypericum species. Progenesis QI and EZinfo were used for chemometrics analysis to link the chemical profile and bioassay activity to aid in the identification of bioactive compounds. In total, 58 compounds were identified from the five species, including compounds with well-characterized bioactivity. Hypericum attenuatum , H. erectum , and H. perforatum , displayed the highest cytotoxicity, and contain the cytotoxic compounds petiolin A, prolificin A, and hypercohin G, respectively. Hypericum faberi and H. perforatum showed the highest anti-inflammatory activity, with pseudohypericin, quercetin and chlorogenic acid being observed at higher concentrations. Hypericum perforatum and H. erectum showed anti-plasmodial activity, with higher hyperforin and xanthones in these species that may account for the anti-plasmodial activity. This study characterized the chemical differences among five Hypericum species using metabolomics. These ethnomedically important species were tested for their biological activities in three distinct in vitro assays. The ethnobotanical data were useful for identifying bioactive Hypericum species. Hypericum attenuatum , H. erectum and H. faberi are promising phytotherapeutic species, although they are much less studied than H. perforatum , St. John's wort. Combining ethnobotanical surveys with chemometric analyses and bioactivity screening can greatly enhance the discovery of promising active constituents. [Display omitted] • Profiled five Hypericum species with non-targeted and targeted chemometrics. • Identified 58 representative compounds from five species that drive chemotaxonomy. • Described Hypericum cytotoxicity, anti-inflammatory, and anti-plasmodial activity. • Employed chemometrics to aid in the identification of bioactive compounds. [ABSTRACT FROM AUTHOR]

[Display omitted] • Correlated Acer truncatum leaf (ATL) metabolites and environmental factors. • Flavonoids (FLAs) and gallic acid-containing products (GANPs) are main metabolites. • Thirty-four compounds were identified for the first time from A. truncatum. • FLAs and GANPs levels are affected by humidity, temperature, and sunshine duration. • Prioritized cultivation sites for harvesting ATL with potential health benefits. Traditionally in Northern China, Acer truncatum leaves (ATL) have been used as herbal tea, now consumed worldwide. Few studies have reported ATL metabolites from different areas and their correlation with the environment. Thus, metabolomic analyses were conducted on ATL collected from twelve locations throughout four environmental zones in Northern China to understand the phytochemical differences with regards to environmental conditions. Sixty-four compounds, mostly flavonoids (FLAs) and gallic acid-containing natural products (GANPs), were characterized, including 34 previously unreported constituents from A. truncatum. Twenty-two markers were useful to differentiate ATL from the four environmental zones. Humidity, temperature, and sunshine duration are the predominant factors affecting FLAs and GANPs levels. Sunshine duration was positively correlated with eriodictyol (r = 0.994, p < 0.01), and humidity negatively with epicatechin gallate (r = −0.960, p < 0.05). These findings provide insights into ATL phytochemistry, aiding cultivation of A. truncatum tea with higher potential health benefits. [ABSTRACT FROM AUTHOR]

Garcinia oblongifolia Champ. ex Benth. (Clusiaceae) is a well-known medicinal plant from southern China, with edible fruits. However, the phytochemistry and bioactivity of the different plant parts of G. oblongifolia have not been studied extensively. Comparative metabolic profiling and bioactivities of the leaf, branch, and fruit of G. oblongifolia were investigated. A total of 40 compounds such as biflavonoids, xanthones, and benzophenones were identified using UPLC-QTOF-MS and MS E , including 15 compounds reported for the first time from this species. Heatmap analyses found that benzophenones, xanthones, and biflavonoids were predominately found in branches, with benzophenones present in relatively high concentrations in all three plant parts. Xanthones were found to have limited distribution in fruit while biflavonoids were present at only low levels in leaves. In addition, the cytotoxic (MCF-7 breast cancer cell line) and antioxidant (ABTS and DPPH chemical tests) activities of the crude extracts of G. oblongifolia indicate that the branch extract exhibits greater bioactivity than either the leaf or the fruit extracts. Orthogonal partial least squares discriminate analysis was used to find 12 marker compounds, mainly xanthones, from the branches, including well-known antioxidants and cytotoxic agents. These G. oblongifolia results revealed that the variation in metabolite profiles can be correlated to the differences in bioactivity of the three plant parts investigated. This UPLC-QTOF-MS strategy can be useful to identify bioactive constituents expressed differentially in the various plant parts of a single species. [ABSTRACT FROM AUTHOR]

The endemic Chilean tree Gomortega keule (Molina) Baillon (Gomortegaceae) was highly appreciated for its edible fruits. Due to substitution of the native forest by tree monocultures, this species in now endangered. Antioxidant assay-guided fractionation of the methanolic extract led to the isolation of eight antioxidant compounds, including rare highly oxygenated coumarins, besides the more common antioxidant compounds chlorogenic acid (compound 6) and rutin (compound 16). The isolation of the compounds was achieved by preparative reverse phase HPLC and the structural elucidation was performed using 1H and 13C NMR techniques. A metabolomic fingerprint was generated and 32 compounds were detected and analyzed on the basis of HPLC-PDA and HR-ESI-ToF-MS. The total phenolic and flavonoid contents of the fruits were determined by spectroscopic means. The content of the major compounds chlorogenic acid (6) and dimethylfraxetin (22) was 51.80±1.49mg/100g dry weight and 9.57±0.11mg/100g dry weight, respectively, while compounds 6 and 16 showed the highest antioxidant capacity (42.37±3.72?g/ml and 23.91±1.50?g/ml in the DPPH scavenging assay, respectively). This is the first report of antioxidant capacity and polyphenolic content of the edible queule fruits. [ABSTRACT FROM AUTHOR]

[Display omitted] • Chemical profiles were established using UPLC-QTof-MS metabolomics. • Over 100 marker compounds contributing to the chemotaxonomy were characterized. • All extracts inhibited NO production in LPS-induced RAW264.7 cells at 100 μ g/mL. • H. japonicum showed cytotoxicity to SMMC-7721 cells (IC 50 = 59.8 μ g/mL). • Potential antiproliferative markers were identified using a chemometrics approach. Many Hypericum species have been used as medicinal plants, herbal teas, and dietary supplements around the world. A previous ethnobotanical survey found that seven Hypericum species in southern China (H. daliense , H. hengshanense , H. himalaicum , H. japonicum , H. petiolulatum subsp. yunnanense , H. seniawinii , and H. wightianum) have been used traditionally to treat inflammation and infectious diseases, but studies on the chemical compositions and bioactivities of these folk medicines are limited. The current study aimed to characterize bioactive marker compounds correlated with two in vitro bioassays for cytotoxicity and anti-inflammation. Methanolic extracts of these species were chemically profiled using UPLC-QTof-MS metabolomics, characterizing the 52 major components from these Hypericum species. To chemically differentiate these seven species, 112 chemical features were characterized as potential chemotaxonomic markers, out of which 89 were tentatively identified. Using a chemometric approach, antiproliferative activity was tracked with chemical markers. H. japonicum showed antiproliferative effects on SMMC-7721 human hepatocarcinoma cell line with an IC 50 value of 59.8 μ g/mL. Comparison of H. japonicum to six other Hypericum species revealed that betulinic acid, isojacareubin, and taxifolin are potential antiproliferative compounds. In addition, a primary in vitro anti-inflammatory assay revealed that all the seven extracts inhibited NO production in lipopolysaccharide-induced RAW 264.7 murine macrophage cells at 100 μ g/mL, indicating that anti-inflammatory compounds may exist in all the seven species. Out of the 52 major components identified from these species, 11 have been previously reported to possess anti-inflammatory properties. These findings provide a scientific rationale for traditional uses of the seven Hypericum species in China and merit further study for the development of new medicinal products. [ABSTRACT FROM AUTHOR]