Two new naphthoquinone derivatives from Sinningia conspicua (Gesneriaceae).

Two new naphthoquinones, 7-hydroxy-2-O-methyldunniol (1) and 7-methoxy-2-O-methyldunniol (2) were isolated from the tubers of Sinningia conspicua (Seem.) G. Nicholson (Gesneriaceae). Nine known compounds were also obtained: 7-methoxydunniol (3), dunniol (4), 7-methoxy-α-dunnione (5), 7-hydroxydunnione (6), 2,4,4',6-tetramethoxychalcone (7), loureirin B (8), allo-calceolarioside A (9), ß-sitosterol (10) and stigmasterol (11). This is the first report of compounds 3 and 5 in Sinningia. n-Hexane, ethyl acetate and ethanol extracts, and compounds 1-5 were tested for cytotoxic activity against PC-3 (prostate) and SKMEL 103 (melanoma) human tumour cell lines and also against the 3T3 (fibroblast) non-cancer cell line. All samples were inactive.

Toxicological evaluation of ethanolic extract of leaves from Doliocarpus dentatus in Swiss mice.

Doliocarpus dentatus (Dilleniaceae) has been used in folk medicine to treat inflammation and pain; however, studies evaluating its toxicity potential, as well as its effects on anxiety and depression, are scarce. This study investigated the toxicological profile of an ethanolic extract from leaves of D. dentatus (EEDd), and its effects on anxiety and depression models in mice. Male and female mice received either a single dose (500, 1000 or 2000 mg/kg) or repeated doses (75, 150 or 300 mg/kg) of EEDd by oral gavage. During the subacute toxicity assay, behavioral tests were performed on days 4, 14, 21 and 28. No evidence of toxicity was observed in the animals in both acute and subacute tests. However, males treated with the highest dose presented a reduction in the absolute weight of the kidney, an elevation in the AST levels, in addition to an alteration in the urea levels. The treatment did not affect other biochemical parameters, and did not induce any depressive-like behavior. EEDd exhibited low toxicity after single and repeated exposures. Since some analyzed parameters were compromised, further toxicity studies should be carried out.

Manufacturing and characterization of craft beers with leaves from Ocimum selloi Benth.

The increase in the manufacture of craft beers follows the boost in the consumption of this beverage. Meanwhile, brewers face a drawback with beer aging, its flavor's change. The addition of compounds that overcome this downside is one alternative used by brewers. Species from the Ocimum genus are known for having antioxidant properties. Therefore, this study aimed to manufacture craft Pilsner beers with increased shelf-life performance. We prepared craft beers adding in natura leaves or aqueous extract from the leaves of Ocimum selloi and determined volatiles, and total phenolic compounds content, pH, color, and antioxidant activity. We can assure that as the fermentation proceeded, there was an increasing at the content of volatile metabolites and the addition of O. selloi improved the shelf-life of the beverages and the antioxidant potential increased when the aqueous extract at 0.1% (m/v) was added after the fermentation step.

Anti-inflammatory activity and chemical composition of aqueous extract and essential oil from leaves of Ocimum selloi Benth.

ETHNOPHARMACOLOGICAL RELEVANCE: The population uses the aqueous extract as tea from leaves of Ocimum selloi Benth. (alfavaca) for pain and inflammation issues. This study is motivated by a lack of data about inflammation properties of O. selloi. AIM OF THE STUDY: This study investigated the chemical composition and anti-inflammatory activity, in mice models, of the aqueous extract (OSAE) and essential oil (OSEO) obtained from leaves of O. selloi. MATERIALS AND METHODS: The antioxidant activity and total phenolic content were evaluated for samples, although chemical composition was obtained by U-HPLC-DAD-ESI-MS for OSAE and GC-MS for OSEO. OSAE and OSEO were tested orally at doses of 30, 100 and 300 mg/kg at the carrageenan-induced pleurisy and paw edema, also mechanical hyperalgesia, in mice. RESULTS: Four glycosylated flavonoids and one organic acid were identified in OSAE, and nine substances in OSEO, the two majoritarian are E-anethole and methyl chavicol. Oral treatments with OSAE and OSEO significantly inhibited the carrageenan-induced pleurisy in female Swiss mice, besides OSAE and OSEO significantly prevented paw edema (after 1, 2, and 4 h), mechanical hyperalgesia (after 3 and 4 h), and cold hyperalgesia 3 h after carrageenan model in male Swiss mice. The dose of 300 mg/kg of OSEO reduced cold hyperalgesia 4 h after carrageenan. CONCLUSION: The results evidenced the anti-inflammatory, anti-edematogenic, anti-hyperalgesic, and anti-nociceptive potentials of both materials obtained from leaves of O. selloi, mainly OSAE, supporting the popular use of this species.

Chemical composition and antiproliferative, antioxidant and trypanocidal activities of the fruits from Campomanesia xanthocarpa (Mart.) O. Berg (Myrtaceae).

Chemical investigation of the extracts of the fruits from Campomanesia xanthocarpa resulted in the isolation of six known compounds identified by NMR and comparison with literature data (2',4'-dihydroxy-5'-methyl-6'-methoxychalcone (1), 2',4'-dihydroxy-3',5'-dimethyl-6'-methoxychalcone (2), 2'-hydroxy-3'-methyl-4',6'-dimethoxychalcone (3), 2',6'-dihydroxy-3'-methyl-4'-methoxychalcone (4), 5-hydroxy-7-methoxy-8-methylflavanone (5) and 7-hydroxy-5-methoxy-6-methylflavanone (6)). The considerable antioxidant capacity of the extracts was demonstrated by ORAC-FL and DPPH tests. The antiproliferative assay of the extracts and 5 was done in vitro, against many different cancer cell lines besides a healthy one. The extracts presented low cytotoxicity and the substance demonstrated promising results against all the cancer cell lines tested, with IC50 values ranging from 4.75 to 45.81 µmol L-1. The in vitro trypanocidal activity was evaluated against the epimastigote form of the Y strain of Trypanosoma cruzi and an improvement in the activity of the substances 2 (221.81 µmol L-1) and 5 (61.87 µmol L-1) was observed regarding the values obtained for the extracts.

Aqueous extract from leaves of Doliocarpus dentatus (Aubl.) Standl. relieves pain without genotoxicity activity.

ETHNOPHARMACOLOGICAL RELEVANCE: In the State of Mato Grosso do Sul, the watery sap of Doliocarpus dentatus is used to alleviate thirst, and the leaves of this species are used to relieve pain and swelling associated with inflammatory processes. AIM OF THE STUDY: This study aimed to analyze the compounds of the leaves from the aqueous extract of D. dentatus (EADd) and evaluate its toxicogenetic and pain relief effects in animal models. MATERIALS AND METHODS: Compounds were identified in EADd by UHPLC-HRMS (Ultra high-performance liquid chromatography coupled to high resolution mass spectrometry). The oral dose of 17 mg/kg EADd, calculated according to ethnopharmacological uses, and doses between 30 and 300 mg/kg were used to test Swiss mice in formalin- and acetic acid-induced models of pain and behavior. EADd (100-2000 mg/kg) was assayed in mice by comet, micronucleus, and phagocytosis tests and by peripheral leukocyte counts. RESULTS: Phenolic compounds and flavonoids as well as trigonelline and isoquercetin were identified in EADd. All oral doses of EADd exhibited antinociceptive activity, as indicated by a decrease in pain in both phases, a decrease in cold hypersensitivity induced by formalin, and a decrease in abdominal contortions induced by acetic acid. EADd did not alter the exploratory, motor or motivational activities of the animals. The comet and micronucleus tests indicated that EADd was not genotoxic and did not change the phagocytic activity or peripheral leukocyte count. CONCLUSIONS: These results demonstrate that EADd could act as an antinociceptive agent that does not present genotoxicity. This study should contribute to justifying, in part, the popular use of D. dentatus in pain management, ensuring its safe use.

Inulin-type fructan and infusion of Artemisia vulgaris protect the liver against carbon tetrachloride-induced liver injury.

BACKGROUND: Infusions of aerial parts of Artemisia vulgaris L. (Asteraceae) are used in herbal medicine to treat several disorders, including hepatosis. PURPOSE: Evaluation of in vivo hepatoprotective effects of A. vulgaris infusion (VI) and inulin (VPI; i.e., the major polysaccharide of VI). STUDY DESIGN: The hepatoprotective effect of A. vulgaris extracts on carbon tetrachloride (CCl4)-induced hepatotoxicity and the probable mechanism involved in this protection were investigated in mice. METHODS: A. vulgaris infusion (VI) was prepared according to folk medicine using the aerial parts of the plant. Carbohydrate, protein, and total phenolic content was determined in VI, and its phenolic profile was determined by high-performance liquid chromatography (HPLC). Male Swiss mice were orally pretreated for 7 days with VI or VPI (once per day). On days 6 and 7 of treatment, the mice were intraperitoneally challenged with CCl4. Liver and blood were collected and markers of hepatic damage in plasma and oxidative stress in the liver were analyzed. Hepatic histology and inflammatory parameters were also studied in the liver. The scavenging activity of VI and VPI were evaluated in vitro using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. RESULTS: VI contained 40% carbohydrates, 2.9% proteins and 9.8% phenolic compounds. The HPLC fingerprint analysis of VI revealed chlorogenic, caffeic and dicaffeoylquinic acids as major low-molar-mass constituents. Oral pretreatment with VI and VPI significantly attenuated CCl4-induced liver damage, reduced the activity of alanine transaminase (ALT), aspartate transaminase (AST), and alkaline phosphatase (ALP) in plasma, and prevented reactive oxygen species accumulation and lipid peroxidation in the liver. Comparisons with the CCl4-treated group showed that VI and VPI completely prevented necrosis, increased the levels of reduced glutathione (GSH), and reduced tumor necrosis factor alpha (TNF-α) level in the liver. VI and VPI also exhibited high radical scavenging activity in vitro. CONCLUSION: VI and VPI had remarkable hepatoprotective effects in vivo, which were likely attributable to antioxidant and immunomodulatory properties. The present findings support the traditional use of A. vulgaris infusion for the treatment of hepatic disorders.

A new naphthoquinone from Sinningia leucotricha (Gesneriaceae).

A new naphthoquinone, 7,8-dimethoxydunnione (1), was isolated from Sinningia leucotricha (Hoehne) Moore tubers, together with four known compounds: 7- hydroxy-t-dunnione (2), 6-methoxy-7-hydroxy-a-dunnione (3), presilphiperfolan-9-ol (4), and betulinic acid (5). All compounds were identified by spectroscopic and mass spectrometric techniques and comparison with literature data. Compounds 2-5 are being reported for the first time in S. leucotricha.

Two new hydronaphthoquinones from Sinningia aggregata (Gesneriaceae) and cytotoxic activity of aggregatin D.

Two new hydronaphthoquinones, aggregatins E and F (1 and 2, resp.) were isolated from the tubers of Sinningia aggregata (Ker-Gawl.) Wiehler (Gesneriaceae), along with twelve known compounds aggregatin D (3), tectoquinone (4), 1-hydroxy-2-methylanthraquinone (5), icosyl ferulate (6), pustuline (7), 1,6-dihydroxy-2-methylanthranquinone (8), 6-hydroxy-2-methylanthraquinone (9), 7-hydroxy-2-methylanthraquinone (10), tyrosol (11), halleridone (12), calceolarioside B (13), and cornoside (14). All compounds were identified by analysis of spectroscopic and spectrometric data. Compounds 3, 4, and 10 had already been reported in this species. Compounds 2 and 3 were evaluated against several tumor cell lines, but only 3 exhibited activities against UACC-62, 786-0 and OVCAR-3 cell lines, with IC50 values of 12.3, 12.8 and 0.3 µg/ml, respectively, without toxic effects on non-cancer cell line HaCat (human keratinocyte).

Chemical Constituents from Sinningia canescens and S. warmingii.

A new naphthoquinone, 6-methoxy-7-hydroxy-a-dunnione (1), along with four known compounds (2, 4, 10, and 11) were isolated from Sinningia canescens (Mart.) Wiehler tubers, while S. warmingii (Hiern.) Chautems furnished eight known compounds (3-10). The known compounds were identified as 7-hydroxy- α-dunnione (2), lapachenole (3), tectoquinone (4), 7-methoxytectoquinone (5), 1-hydroxytectoquinone (6), 7-hydroxytectoquinone (7), aggregatin C (8), aggregatin D (9), halleridone (10), and cedrol (11). In addition, S. canescens yielded a volatile fraction, which was analyzed by GC/FID and GC/MS. This fraction was constituted mainly by sesquiterpene hydrocarbons (82.6%). The major components were ß-santalene (14.6%), ß-cedrene (10.4%), and trans-cadina-1(6)-4-diene (10.0%).

Secondary metabolites and biological properties of Gesneriaceae species.

The family Gesneriaceae comprises ca. 150 genera and 3000 species, distributed in the tropics around the world. It is constituted of herbs, lianas, or shrubs, frequently with ornamental potential, due to the beauty of their flowers. Some species have been used in traditional medicine, mainly against fever, cough, colds, snakebite, pains, and infectious and inflammatory diseases. Although Gesneriaceae are a large family, only few species were chemically investigated, and this took place mainly in the last decade. In the present work, chemical and pharmacological studies on Gesneriaceae are reviewed based on original articles published. Altogether 300 compounds have been reported in Gesneriaceae species, including flavonoids, terpenes and steroids, phenolic glucosides, simple phenolics, quinones, lignans, xanthones, and compounds with unusual skeletons. Several species had been used in folk medicine, and some constituents have shown biological activities, such as antimicrobial, anti-inflamatory, antioxidant, and antitumor properties.

Lactones and quinones from the tubers of Sinningia aggregata.

Three new aromatic epsilon-lactones, aggregatins A (1), B (2), and C (3), a new naphthoquinone derivative, aggregatin D (4), and three known anthraquinones, 2-methylanthraquinone, 7-methoxy-2-methylanthraquinone, and 7-hydroxy-2-methylanthraquinone, were isolated from the tubers of Sinningia aggregata (Gesneriaceae). Compounds 1 and 4 and the anthraquinones showed marginal antimicrobial activity.