Hop (Humulus lupulus L.) terroir has large effect on a glycosylated green leaf volatile but not on other aroma glycosides.

Genetics and environment both influence the content of hop (Humulus lupulus L.) aroma compounds. The effects of these two factors on aroma glycosides, which can change the aroma profile of beer over time, were examined in a preliminary study. Twenty-three hop cultivars were grown in the northwestern United States in two locations with distinct terroirs. UPLC-MS/MS analysis of hop cone extracts revealed that growing location had a large effect on hexyl glucoside levels but only a negligible effect on levels of linalyl, raspberry ketone, and 2-phenylethyl glucoside, which were mostly affected by genetic differences. The large terroir effect on hexyl glucoside, which releases a green leaf volatile with a grassy aroma when hydrolyzed, but not on the other aroma glucosides, which have more desirable aromas when hydrolyzed, could have an impact on beer aroma profiles.

A critical review of the composition and history of safe use of guayusa: a stimulant and antioxidant novel food.

Due to rapid international market development, there is a strong and urgent need to assess the safety of the novel food, Ilex guayusa. Guayusa has been consumed for centuries in the western Amazon as an herbal tea, and novel food regulation provide a detailed framework for safety assessment of novel foods with such a history of use. This study reviews guayusa's taxonomy, chemical composition, toxicology, ethnobotany, and history of safe use as key elements of a robust novel food safety assessment. Guayusa is a product of traditional agricultural systems with a continuous history of consumption in Ecuador. Its known chemical composition appears to present no greater risk to human health than existing teas such as green tea or yerba mate, although our understanding of guayusa's chemical profile is still nascent, requiring further investigation. Broad consumption of guayusa is not associated with a history of adverse effects or product safety notifications. Biochemical and phytochemical studies have profiled its nutritional content, metabolite composition, and bioactivity, validating guayusa's antioxidant and stimulant properties. In conclusion, guayusa leaves have a well-documented chemical composition and history of safe use, which are key considerations for authorization as a novel food in the EU.

Cytotoxic Xanthones from Hypericum stellatum, an Ethnomedicine in Southwest China.

Hypericum stellatum, a species endemic to China, is used to treat hepatitis by several ethnic groups in Guizhou Province. This research was inspired by the traditional medicinal usage of H. stellatum, and aims to explore the phytochemistry and bioactivity of H. stellatum to explain why local people in Guizhou widely apply H. stellatum for liver protection. In this study, two new prenylated xanthones, hypxanthones A (8) and B (9), together with seven known compounds, were isolated from the aerial parts of the plant. Spectroscopic data as well as experimental and calculated ECD spectra were used to establish the structures of these compounds. Six xanthones isolated in this study, together with four xanthones previously isolated from H. stellatum, were evaluated for their growth-inhibitory activities against five human liver carcinoma cell lines to analyze the bioactivity and structure-activity relationship of xanthones from H. stellatum. Isojacareubin (6) showed significant cytotoxicity against five human liver carcinoma cell lines, with an IC50 value ranging from 1.41 to 11.83 µM, which was stronger than the positive control cisplatin (IC50 = 4.47-20.62 µM). Hypxanthone B (9) showed moderate cytotoxicity to three of the five cell lines. Finally, structure-activity analysis revealed that the prenyl and pyrano substituent groups of these xanthones contributed to their cytotoxicity.

LC-MS Metabolomics and Chemotaxonomy of Caffeine-Containing Holly ( Ilex) Species and Related Taxa in the Aquifoliaceae.

Ilex species have been consumed traditionally as medicinal teas worldwide. Though the presence of caffeine has been reported in several species, little is known about secondary-metabolite diversity within and among these taxa. Leaf samples of Ilex guayusa, Ilex paraguariensis, and Ilex vomitoria were analyzed by liquid chromatography-mass spectrometry and comparative metabolite profiling with Ilex cassine and other Ilex species to identify chemotaxonomic markers, delimit species, and provide an assessment of chemodiversity. Purine alkaloids were detected and quantified in I. guayusa, I. paraguariensis, and I. vomitoria. Reports of caffeine for I. cassine were not corroborated, suggesting that I. vomitoria was the traditional source of the Native North American tea yaupon. The tetramethyluric acid, theacrine, was detected for the first time in the genus Ilex as a low-level chemotaxonomic marker in I. vomitoria samples. Chemotaxonomy and metabolomics support a close relationship for caffeine-containing Ilex species.

Metabolic Profiling of Different Parts of Acer truncatum from the Mongolian Plateau Using UPLC-QTOF-MS with Comparative Bioactivity Assays.

Acer truncatum is an important ornamental, edible, and medicinal plant resource in China. Previous phytochemical research has focused on the leaf (AL) due to its long history as a tea for health. Other parts such as the branch (ABr), bark (ABa), fruit (AF), and root (AR) have drawn little attention regarding their metabolites and bioactivities. The strategy of an in-house chemical library combined with Progenesis QI informatics platform was applied to characterize the metabolites. A total of 98 compounds were characterized or tentatively identified, including 63 compounds reported from this species for the first time. Principal component analysis showed the close clustering of ABr, ABa, and AR, indicating that they share similar chemical components, while AL and AF clustered more distantly. By multiple orthogonal partial least-squares discriminant analyses (OPLS-DA), 52 compounds were identified as potential marker compounds differentiating these different plant parts. The variable influence on projection score from OPLS-DA revealed that catechin, procyanidins B2 or B3, and procyanidins C1 or C2 are the significant metabolites in ABa extracts, which likely contribute to its antioxidant and cytotoxic activities.

Jaboticabin and Related Polyphenols from Jaboticaba ( Myrciaria cauliflora) with Anti-inflammatory Activity for Chronic Obstructive Pulmonary Disease.

Myrciaria cauliflora (jaboticaba) is an edible fruit common in Brazil that has been used for treating respiratory diseases, including chronic tonsillitis and asthma. This study explores the distribution of an anti-inflammatory depside, jaboticabin, in different parts of the jaboticaba plant as well as major polyphenols from the wood of jaboticaba, some with biological activity similar to jaboticabin. The peel of the fruit was found to be the major source of jaboticabin. This is the first phytochemical study of the wood of M. cauliflora. The antioxidant-activity-guided fractionation strategy successfully identified 3,3'-dimethylellagic acid-4- O-sulfate from jaboticaba wood. This ellagic acid derivative, in a manner similar to jaboticabin, showed antiradical activity and inhibited the production of the chemokine interleukin-8 after treating the human small airway epithelial cells with cigarette smoke extract. The human intestinal Caco-2 cell studies demonstrated the jaboticabin transport in vitro. The polyphenols, jaboticabin and 3,3'-dimethyellagic acid-4- O-sulfate, from jaboticaba were both found to exhibit anti-inflammatory activities, thus suggesting the potential use of these compounds or even the fruits themselves for chronic obstructive pulmonary disease.

Dextran hydrogels by crosslinking with amino acid diamines and their viscoelastic properties.

Amine functionalized polysaccharide hydrogels such as those based on chitosan are widely examined as biomaterials. Here we set out to develop a facile procedure for developing such hydrogels by crosslinking dextran with amino acid diamines. The dextran-amino acid gels were formed by the addition of the amino acid diamines to a dextran and epichlorohydrin solution once it became homogeneous. This was demonstrated with three amino acid diamines, lysine, lysine methyl ester, and cystine dimethyl ester. Hydrogel networks with albumin entrapped were also demonstrated. These hydrogels were characterized by FTIR, SEM, rotational rheometry, swelling studies and cell biocompatibility analysis. These hydrogels showed the unexpected pH-responsive behavior of greater swelling at more basic pH, similar to that of an anionic hydrogel. This is uncharacteristic for amine functionalized gels as they typically exhibit cationic hydrogel behavior. All hydrogels showed similar biocompatibility to that of dextran crosslinked without amino acids.

Traditional preparation of Phaleria nisidai, a Palauan tea, reduces exposure to toxic daphnane-type diterpene esters while maintaining immunomodulatory activity.

ETHNOPHARMACOLOGICAL RELEVANCE: The leaves of Phaleria nisidai Kaneh. (Thymelaeaceae) are brewed into a tea commonly used as a tonic, strengthening beverage and immune enhancer in Palau, Micronesia. Recently, the leaves of P. nisidai have been shown to contain toxic daphnane diterpene esters which may pose a public health threat to Palauans. AIMS OF THE STUDY: This project documents the use frequency, preparation and side effects of P. nisidai. The content of daphnane diterpene esters in aqueous and methanol extracts and infusions prepared by healers in Palau is compared to assess the risk of daphnane ingestion associated with traditional consumption. Quantitative results are correlated with an in vitro assessment of the immunomodulating activity of the extracts. MATERIALS AND METHODS: Research participants, comprising traditional healers and laypeople, were interviewed concerning use patterns and side effects of P. nisidai. Several traditional healers prepared and provided boiled tea samples for chemical analysis. Leaves were collected and methanolic and aqueous extractions were prepared in the laboratory. Peripheral blood mononuclear cells (PBMCs) were cultured with various concentrations of methanol and aqueous leaf extracts and their output of IFNγ was measured using ELISA. Cell proliferation was also assessed using the MTT assay. The concentration of selected daphnane diterpene esters in healer-prepared infusions, lab methanol and lab aqueous extracts was quantified using ultraperformance liquid chromatography-mass spectrometry-triple quadrupole detection (UPLC-MS-TQD). RESULTS: Through structured interviews it was determined that P. nisidai tea was used frequently, with many participants drinking it daily. The reported side effects were mild, and with the exception of diarrhea (n=2), no side effect was mentioned more than once. Methanol extracts contained 4.0µg simplexin, 17.6µg acetoxyhuratoxin and 2.3µg huratoxin per g dry leaf material. In traditional water infusions provided by healers and in standardized lab-prepared aqueous extracts all three compounds were below the limit of detection (16.3ng/mL) using our UPLC-MS-TQD method. Methanol and aqueous extracts increased the release of IFNγ by PBMCs (p<0.05); however, methanol extracts were significantly more active than aqueous extracts (p<0.05). Methanol and aqueous extracts significantly increased proliferation of PBMCs, causing at least 60% more cell proliferation than negative control (p<0.05). CONCLUSIONS: The presence of daphnane diterpene esters in a frequently consumed traditional beverage was initially viewed as a public health concern, though interview data reveal that Palauans do not observe toxicity or side effects associated with their use of P. nisidai tea. Concurrently, daphnanes are present in methanolic extracts but not detected in aqueous preparations indicating that the traditional method of preparation avoids the extraction of these potentially toxic compounds, while still maintaining immunostimulant activity.

Chemical composition and antioxidant activity of seven cultivars of guava (Psidium guajava) fruits.

The antioxidant activity and identification of phenolic compounds of seven edible guava (Psidium guajava) cultivars that varied in colour from white to pink were examined. In the DPPH assay all four pink-pulp guavas (Barbie Pink, Homestead, Sardina 1, Sardina 2) included in the study showed higher activity than the white pulp cultivars (Yen 2 and Sayla) and less than the red pulp guava cultivar (Thai Maroon). In the ABTS(+) assay this trend was the same up to 20 min, but from 20 to 40 min Barbie Pink showed lower activity than the white guavas. Twenty-one compounds were characterised in the cultivars, and ten of them are reported for the first time in this fruit. Principle component analysis was performed to identify differences in chemistry among these cultivars. Our results suggest that the antioxidant activity and phytochemical composition of P. guajava vary significantly according to the cultivar and pulp colour.

In vitro antiplasmodial activity of benzophenones and xanthones from edible fruits of Garcinia species.

Species of Garcinia have been used to combat malaria in traditional African and Asian medicines, including Ayurveda. In the current study, we have identified antiplasmodial benzophenone and xanthone compounds from edible Garcinia species by testing for in vitro inhibitory activity against Plasmodium falciparum. Whole fruits of Garcinia xanthochymus, G. mangostana, G. spicata, and G. livingstonei were extracted and tested for antiplasmodial activity. Garcinia xanthochymus was subjected to bioactivity-guided fractionation to identify active partitions. Purified benzophenones (1-9) and xanthones (10-18) were then screened in the plasmodial lactate dehydrogenase assay and tested for cytotoxicity against mammalian (Vero) cells. The benzophenones guttiferone E (4), isoxanthochymol (5), and guttiferone H (6), isolated from G. xanthochymus, and the xanthones α-mangostin (15), ß-mangostin (16), and 3-isomangostin (17), known from G. mangostana, showed antiplasmodial activity with IC50 values in the range of 4.71-11.40 µM. Artemisinin and chloroquine were used as positive controls and exhibited IC50 values in the range of 0.01-0.24 µM. The identification of antiplasmodial benzophenone and xanthone compounds from G. xanthochymus and G. mangostana provides evidence for the antiplasmodial activity of Garcinia species and warrants further investigation of these fruits as dietary sources of chemopreventive compounds.