-Kaurane Diterpenoids from Genus: An Update of Chemical Diversity and Biological Aspects.

Coffee is one of the most important beverages in the world and is produced from spp. beans. Diterpenes with -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.

Anti-Inflammatory, Antinociceptive, and LC-MS Metabolic Profile from (Klatt) Lovo & A. Gil.

(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.

Extraction of Diterpene-Phytochemicals in Raw and Roasted Coffee Beans and Beverage Preparations and Their Relationship.

Cafestol and kahweol are expressive furane-diterpenoids from the lipid fraction of coffee beans with relevant pharmacological properties for human health. Due to their thermolability, they suffer degradation during roasting, whose products are poorly studied regarding their identity and content in the roasted coffee beans and beverages. This article describes the extraction of these diterpenes, from the raw bean to coffee beverages, identifying them and understanding the kinetics of formation and degradation in roasting (light, medium and dark roasts) as the extraction rate for different beverages of coffee (filtered, Moka, French press, Turkish and boiled).

Heteromorphic stamens are differentially attractive in (Fabaceae).

The division of labour hypothesis between stamens has explained the evolution of divergent functions between dimorphic stamens in the same flower. However, little is known about whether the distinct type of stamens differs in attractiveness to pollinators. Therefore, we investigate whether the two types of stamens commonly found in have different visual and olfactory attractants.

Metabolic study of cafestol using in silico approach, zebrafish water tank experiments and liquid chromatography high-resolution mass spectrometry analyses.

Coffee is one of the most consumed beverages worldwide. Cafestol is an endogenous coffee diterpene present in raw coffee beans and also found in hot beverages, with several biological activities. However, there is still little information on this molecule after ingestion of coffee infusion.

Characterization of -Octadecanoyl-5-hydroxytryptamide Anti-Inflammatory Effect.

Background: -octadecanoyl-5-hydroxytryptamide (C-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-5HT.

Methods: A subcutaneous air pouch model (SAP) was used.

TLC-ESI-MS as a QuEChERS approach to detection of capsaicin present in different matrices.

Pepper is one of the most consumed spices in the world. Its main compound is capsaicin, a widely studied biomarker that has pharmacological activities due to its anti-inflammatory and analgesic capacity. Topical formulations such as patches based on capsaicin have been developed as an option in relieving pain and reducing swelling.

Two New -Alkanoyl-5-Hydroxytryptamides with Relevant Antinociceptive Activity.

In this work, we describe a new route for the synthesis and the antinociceptive effects of two new -alkanoyl-5-hydroxytryptamides (named C-5HT and C-5HT). The antinociceptive activities were evaluated using well-known models of thermal-induced (reaction to a heated plate, the hot plate model) or chemical-induced (licking response to paw injection of formalin, capsaicin, or glutamate) nociception. The mechanism of action for C-5HT and C-5HT was evaluated using naloxone (opioid receptor antagonist, 1 mg/kg), atropine (muscarinic receptor antagonist, 1 mg/kg), AM251 (cannabinoid CB1 receptor antagonist, 1 mg/kg), or ondansetron (5-HT3 serotoninergic receptor antagonist, 0.

Comprehensive lipid analysis of green Arabica coffee beans by LC-HRMS/MS.

Lipids play an important role in coffee bean development, coffee brew and in the effects of coffee on human health. They account for around 17% of the dry bean weight and encompass different classes and subclasses, mostly triacylglycerols (TAG) and a minor quantity of phospholipids (PL) and N-alkanoyl-5-hydroxytryptamides (C-5HT). To comprehensive profile these different lipids, it is important to evaluate extraction methods that provide high lipid coverage and to analyze the lipids in high-resolution techniques.

Fast and Highly Selective Continuous-Flow Catalytic Hydrogenation of a Cafestol-Kahweol Mixture Obtained from Green Coffee Beans.

This work investigates batch and continuous-flow heterogeneous catalytic hydrogenation of a mixture of cafestol and kahweol (C&K) to obtain pure cafestol. These diterpenes were extracted from green coffee beans, and hydrogenation was performed using well-established palladium catalysts (Pd/C, Pd/CaCO, Pd/BaSO, and Pd/AlO) and a carbon black-supported Pd catalyst coated by a covalently tethered SiO shell with mesoporous texture (Pd/CB@SiO), all partially deactivated with quinoline. Pd/C 10% poisoned with 1 wt % quinoline gave the best result for batch reaction, producing cafestol from kahweol with high selectivity (>99%) after 10 min.

Dynamics of volatile compounds in TSH 565 cocoa clone fermentation and their role on chocolate flavor in Southeast Brazil.

The effects of indigenous fermentation on volatile compound profiles in a L, TSH565 clone, resistant to and spp. were evaluated in Southern Brazil. Sixty-three volatile flavor compounds in pulp and 36 in grains were identified by SPME-HS/GC-MS and classified as terpenes, alcohols, esters, ketones and aldehydes, among others.

New approaches to monitor semi-volatile organic compounds released during coffee roasting using flow-through/active sampling and comprehensive two-dimensional gas chromatography.

A novel dynamic approach is described to profile volatile organic compound (VOC) and semi-VOC (SVOC) emission during coffee roasting aimed at analysing components present in the roasting plume, and to monitor their evolution during the process. Two sorbents - coconut shell charcoal (CSC) and styrene-divinylbenzene resin (XAD-2) - were evaluated while collecting substances in four sequential time intervals (0-3, 3-6, 6-9 and 9-12 min). Extracted VOCs (<200 Da) and SVOCs were analysed by gas chromatography (GC), and comprehensive two-dimensional gas chromatography (GC × GC) with flame ionisation (FID) and time-of-flight mass spectrometry (TOFMS) detection.

Gas chromatography-mass spectrometry of sapucainha oil (Carpotroche brasiliensis) triacylglycerols comprising straight chain and cyclic fatty acids.

Sapucainha oil, which may be used to treat leprosy, comprises straight chain and cyclic fatty acids (FA), and triacylglycerols (TAG). The FA and TAG content of the oil sample was analysed using gas chromatography-electron ionisation mass spectrometry (GC-EIMS). FA analysis was performed after derivatisation to fatty acid methyl esters (FAME).

Reduction of N-alkanoyl-5-hydroxytryptamides and diterpenes by yeast supplementation to green coffee during wet processing.

Coffee is one of the most consumed non-alcoholic beverages in the world. It is well known that some compounds present in coffee beans have important biological activities. In this study, evidence was turned to N-alkanoyl-5-hydroxytryptamides (C-5HTs) and to the furokaurane diterpenes cafestol and kahweol, associated with gastric irritation and increasing of blood cholesterol, respectively.

New N-octadecanoyl-5-hydroxytryptamide: antinociceptive effect and possible mechanism of action in mice.

The present study examined the potential antinociceptive activity of C18 5-HT (N-octadecanoyl-5-hydroxytryptamide) using chemical and thermal nociception models in mice. Orally administered C18 5-HT (0.1, 1 and 10 mg/kg) produced significant dose-dependent antinociceptive effects in formalin-, capsaicin- and glutamate-induced licking models.

Lipase-catalysed esters synthesis of cafestol and kahweol.

Cafestol and kahweol (C&K), two coffee diterpene alcohols with structural similarity which exhibit anticarcinogenic effects, were isolated from green coffee Arabica beans, followed by their lipase-catalysed esterification and purification by preparative high-performance liquid chromatography (HPLC). The isolation and enzymatic synthesis parameters of C&K esters were studied, with the latter optimised by a Central Composite Design; both procedures were monitored by gas chromatography. Scale up and improved isolation conditions resulted in 1.

Ionic liquid capillary columns for analysis of multi-component volatiles by gas chromatography-mass spectrometry: performance, selectivity, activity and retention indices.

This study investigates applications and performance evaluation of SLB-IL60, SLB-IL76 and SLB-IL111 columns, in relation to a DB-Wax column, for the analysis of coffee volatile compounds. Both standards and an authentic coffee sample were analysed, with solid-phase microextraction (SPME) sampling of the latter. A cryofocusing method was applied to improve resolution of the earliest eluting peaks using splitless injection SPME sample analysis.

Analysis of underivatised low volatility compounds by comprehensive two-dimensional gas chromatography with a short primary column.

Comprehensive two-dimensional gas chromatography (GC×GC) approaches with cryogenic modulation were developed for the qualitative analysis of selected low volatility compounds in raw coffee bean extracts, without derivatisation. The approaches employed short first (D) and second (D) dimension columns, specifically a D 65% phenyl methyl siloxane column (11m) and a D 5% phenyl methyl siloxane column (1m), which allowed elution of high molar mass compounds (e.g.

Qualitative analysis of Copaifera oleoresin using comprehensive two-dimensional gas chromatography and gas chromatography with classical and cold electron ionisation mass spectrometry.

Improved separation of both sesquiterpenes and diterpenic acids in Copaifera multijuga Hayne oleoresin, is demonstrated by using comprehensive two-dimensional gas chromatography (GC×GC) coupled to accurate mass time-of-flight mass spectrometry (accTOFMS). GC×GC separation employs polar phases (including ionic liquid phases) as the first dimension (D) column, combined with a lower polarity D phase. Elution temperatures (Te) of diterpenic acids (in methyl ester form, DAME) increased as the D McReynolds' polarity value of the column phase decreased.

Studies on the volatile fraction composition of three native Amazonian-Brazilian fruits: Murici (Byrsonima crassifolia L., Malpighiaceae), bacuri (Platonia insignis M., Clusiaceae), and sapodilla (Manilkara sapota L., Sapotaceae).

The volatile fraction of murici, bacuri and sapodilla are here studied because of their increasing interest for consumers, abundance of production in Brazil, and the general demand for new flavors and aromas. Their volatile profiles were studied by two High Concentration Capacity Headspace techniques (HCC-HS), Headspace Solid Phase Microextraction (HS-SPME) and Headspace Sorptive Extraction (HSSE), in combination with GC-MS. Murici volatile fraction mainly contains esters (38%), carboxylic acids (19%), aldehydes (11%), alcohols (14%), others (13%) and sulfur compounds; bacuri is characterized by terpenes (41%), non-terpenic alcohols (24%), esters (15%), aldehydes (6%), and others (12%); sapodilla consists of esters (33%), alcohols (27%), terpenes (18%) and others (21%).

Structure Elucidation, Antimicrobial and Cytotoxic Activities of a Halimane Isolated from Vellozia kolbekii Alves (Velloziaceae).

A new halimane diterpene was isolated from Vellozia kolbekii Alves (Velloziaceae) and identified as (5R,8R,9S,13R)-halim-1,10-ene-15,16-diol (1). It showed cytotoxicity against three human cancer cell lines, SF-295 (glioblastoma), MDA-MB-435 (melanoma), and HCT-8 (colon adenocarcinoma). In the mechanism of cytotoxic action, halimane 1 interferes in two major phases of the cell cycle: in S phase, in which DNA synthesis occurs and where it is very sensitive to damage, and G2M phase which is the phase of preparation for mitosis and mitosis itself, showing apoptosis-inducing properties.

Electrospray ionization tandem mass spectrometry analysis of isopimarane diterpenes from Velloziaceae.

Rationale: The study of natural products by electrospray ionization tandem mass spectrometry (ESI-MS/MS) is an important strategy for the characterization of the major fragmentation reactions which can then help to determine the composition of complex mixtures. Application of ESI-MS/MS to a series of isopimarane diterpenes from Velloziaceae allowed the rationalization of their fragmentation mechanisms.

Methods: Velloziaceae diterpenes were isolated by silica gel column chromatography and investigated by ESI-MS/MS analysis.

New approaches on the analyses of thermolabile coffee diterpenes by gas chromatography and its relationship with cup quality.

A new gas chromatography method using pulsed split injector (PS-GC) was validated to quantify thermolabile diterpenes cafestol, kahweol and isokahweol in methanolysed Arabica coffee oils. Linearity was 0.99 from 8 to 69mgmL(-1), recovery ranged from 99% to 101% and precision of less than 4% was obtained.

New natural diterpene-type abietane from Tetradenia riparia essential oil with cytotoxic and antioxidant activities.

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.