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Coffee is one of the most important beverages in the world and is produced from Coffea spp. beans. Diterpenes with ent -kaurane backbones have been described in this genus, and substances such as cafestol and kahweol have been widely investigated, along with their derivatives and biological properties. Other coffee ent -kaurane diterpenoids have been reported with new perspectives on their biological activities. The aim of this review is to update the chemical diversity of ent -kaurane diterpenoids in green and roasted coffee, detailing each new compound and reporting its biological potential. A systematic review was performed using the bibliographic databases (SciFinder, Web of Science, ScienceDirect) and specific keywords such as "coffea diterpenes", "coffee diterpenes", "coffee ent-kaurane diterpenes" and "coffee diterpenoids". Only articles related to the isolation of coffee ent -kaurane compounds were considered. A total of 146 compounds were related to Coffea spp. since the first report in 1932. Different chemical skeletons were observed, and these compounds were grouped as furan-type, oxidation-type, rearrangement-type, lacton-type, and lactam-type, among others. In general, the new coffee diterpenoids showed potential as antidiabetic, antidiapogenic, α-glucosidade inhibition, antiplatelet activity, and Cav.3 inhibitors agents, revealing the possibilities for the design, discovery, and development of new drugs.

Pseudotrimezia juncifolia (Klatt) Lovo & A. Gil (Iridaceae) is a popularly known species with primarily ornamental economic interest. It has traditional uses as purgative, in conditions related to the menstrual cycle, for blood purification, as wound healing, and as anti-inflammatory. The anti-inflammatory and antinociceptive activities of the decoction from its aerial stems, corms, and stamens are described here with dereplication studies on LC-MS/MS supported by the GNPS platform, where phenolic compounds were annotated and correlated with its biological activity. The decoction was evaluated in chemical (formalin and capsaicin) and thermal (hot plate) induced nociception or carrageenan-induced inflammation in mice. Decoction (at 10, 30, or 100 mg/kg doses) significantly reduced formalin- or capsaicin-induced nociception. All doses also demonstrated an antinociceptive effect in the hot plate model increasing the time the animal spent in responding to thermal signal. Naloxone partially reversed the antinociceptive effect. An anti-inflammatory effect was observed since a reduction in cell migration, protein extravasation interleukin-1, and tumor necrosis factor production induced by carrageenan in the subcutaneous air pouch was quantified. Metabolomic analyses showed a predominance of phenolic substances, mainly flavonoids and chlorogenic acids. The literature showed that these two groups have significant anti-inflammatory and analgesic activity, and chemical data corroborate the pharmacological results observed.

Background: N -octadecanoyl-5-hydroxytryptamide (C 18 -5HT) is an amide that can be obtained by the coupling of serotonin and octadecanoic acid. This study aims to characterize the in vivo and in vitro anti-inflammatory activity of C 18 -5HT., Methods: A subcutaneous air pouch model (SAP) was used. The exudates were collected from SAP after carrageenan injection to assess cell migration and inflammatory mediators production. RAW 264.7 cells were used for in vitro assays., Results: C 18 -5HT significantly inhibited leukocyte migration into the SAP as well as nitric oxide (NO) and cytokines production and protein extravasation. We also observed an reduction in some cytokines and an increase in IL-10 production. Assays conducted with RAW 264.7 cells indicated that C 18 -5HT inhibited NO and cytokine produced., Conclusions: Taken together, our data suggest that C 18 -5HT presents a significant effect in different cell types (leukocytes collected from exudate, mainly polumorphonuclear leukocytes and cell culture macrophages) and is a promising compound for further studies for the development of a new anti-inflammatory drug.

Tetradenia riparia (Hochstetter) Codd belongs to the Lamiaceae family and it was introduced in Brazil as an exotic ornamental plant. A previous study showed its antimicrobial, acaricidal and analgesic activities. Two compounds were isolated from essential oil of T. riparia leaves and identified as 9β,13β-epoxy-7-abietene (1), a new one, and 6,7-dehydroroyleanone (2), already reported for another plant. The structure of these compounds was determined by spectroscopic analysis and by comparison with literature data. The cytotoxic activities of the essential oil and compounds 1 and 2 were determined by a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay, and by tumor cells MDA-MB-435 (human breast carcinoma), HCT-8 (human colon), SF-295 (human nervous system) and HL-60 (human promyelocytic leukemia). The essential oil and compound 1 showed high cytotoxic potential of the cell lines SF-295 (78.06% and 94.80%, respectively), HCT-8 (85.00% and 86.54%, respectively) and MDA-MB-435 (59.48% and 45.43%, respectively). Compound 2 had no cytotoxic activity. The antioxidant activity was determined by 2,2-diphenyl-1-picryl-hydrazyl (DPPH), β-carotene-linoleic acid system and 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assays. The inhibitory concentration (IC50 in µg mL-1) for essential oil and compound 2 was, respectively 15.63 and 0.01 for DPPH; 130.1 and 109.6 for β-carotene-linoleic acid and 1524 and 1024 for ABTS. Compound 1 had no antioxidant activity. By fractioning the oil, it was possible to identify two unpublished compounds: 1 with high cytotoxic potential and 2 with high antioxidant potential.

The seasonal variation of the chemical composition of the essential oil from fresh leaves of Tetradenia riparia (Hochst.) Codd grown in southern Brazil was analyzed by GC-MS, and the analgesic and antimicrobial activities of this oil were assayed. The yield of essential oil ranged from 0.17% to 0.26%, with the maximum amount in winter and the minimum in spring. The results obtained from principal components analysis (PCA) revealed the existence of high chemical variability in the different seasons. The samples were clearly discriminated into three groups: winter, autumn, and spring-summer. Samples collected during winter contained the highest percentages of calyculone (24.70%), abietadiene (13.54%), and viridiflorol (4.20%). In autumn, the major constituents were ledol (8.74%) and cis-muurolol-5-en-4-alpha-ol (13.78%). Samples collected in spring-summer contained the highest percentages of fenchone (12.67%), 14-hydroxy-9-epi-caryophyllene (24.36%), and alpha-cadinol (8.33%). Oxygenated sesquiterpenes were predominant in all the samples analyzed. The observed chemovariation might be environmentally determined by a seasonal influence. The essential oil, when given orally at a dose of 200 mg/kg, exhibited good analgesic activity on acetic acid-induced writhing in mice, inhibiting the constrictions by 38.94% to 46.13%, and this effect was not affected by seasonal variation. The antimicrobial activity of the essential oil against the bacterial strains: Staphylococcus aureus, Bacillus subtilis, Enterococcus faecalis, Escherichia coli, Salmonella enterica, Pseudomonas aeruginosa, Klebsiella pneumonia, Proteus mirabilis, Morganella morganii, and Enterobacter cloacae, and the pathogenic fungus Candida albicans was assessed by the disc diffusion method and determination of the minimum inhibitory concentration. The results obtained, followed by measurement of the minimum inhibitory concentration (MIC), indicated that S. aureus, B. subtilis, and Candida albicans were the most sensitive microorganisms, showing largest inhibition, and the lowest MIC values varied from 15.6 to 31.2 microg/mL, 7.8 to 15.6 microg/mL, and 31.2 to 62.5 microg/mL, respectively.