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ABSTRACT In the Amazon region, andiroba (Carapa guianensis) oil is among the most used products by the local population due to its medicinal properties. Previously, our group described the leishmanicidal activity of three limonoid-rich fractions from andiroba oil. This work aimed to evaluate the antioxidant activity and ultrastructural changes in Leishmania amazonensis treated with these limonoid-rich fractions from andiroba oil: 6α,11β-diacetoxygedunin; 11β-hydroxygedunin; and a fraction with both 6α,11β-diacetoxygedunin +11β-hydroxygedunin. The antioxidant activity was evaluated by the DPPH method and ultrastructural changes were evaluated by transmission electron microscopy. The fraction with both 6α,11β-diacetoxygedunin + 11β-hydroxygedunin displayed the best antioxidant activity (IC50 330.35 ± 8.60 µg mL-1; p=0.0022) compared to the 6α,11β-diacetoxygedunin fraction. The three fractions induced structural changes to mitochondria and kinetoplasts of L. amazonensis, in addition to lipid bodies, vacuolization, and vesicles in the flagellar pocket, indicating that the limonoid-rich fractions from andiroba oil can induce structural damage to Leishmania.

The seed oil of Carapa guianensis, known as crabwood oil (CWO), is distinguished for its medicinal and cosmetics applications, attributed to its bioactive components and lipid profile. CWO and its dry and solvent fractionation were studied, with a focus on physicochemical functionality and the partitioning of known bioactive compounds, such as limonoids and sterols. Important bioactive components, including limonoids and sterols, were partitioned depending on the fractionation method; in particular, there is a direct dependence on solvent polarity. There was a very strong solid fraction yield–solvent polarity with a high linear slope of −121.3%. The partitioning of the lipids is significant enough to drive measurable and predictable changes in the physical properties. Palmitic (P: C16:0) and oleic (O: C18:1) fatty acids account for about 60% of the total fatty acid composition of the TAGs of CWO and its fractions. The most abundant limonoid is methyl angolensate (from 28 to 39%), followed by Trichilin A (from 13% to 22%). Gedunin and Andirobin were more abundant in the liquid fractions, whereas Carapanolides (less than 1.3%) were more present in the olein fractions. The crystallization and melting temperatures of the solid fractions were up to 26 °C, compared to 11°C for CWO, and were particularly strongly correlated to the polarity of the solvents. The SFC profile indicated semi-solid fats, with the solid fractions showing up to 19% at 18 °C, twice the SFC in CWO. The fractions demonstrated a wide range of distinguishable microstructures. The shapes include well-organized spherulites and needle-like and rod-like crystals with sizes varying from 5 to 250 µ, suggesting that they are likely to have different flow characteristics and feel to the skin and mouth. There is a potential to make unique compositions with significantly different properties, with antimicrobial and antifungal efficacy due to the bioactive components of CWO through fractionation, using polarity as a predictive tool. [ABSTRACT FROM AUTHOR]

The seed oil of Carapa guianensis Aublet (Andiroba) has been used in folk medicine for its insect-repelling, anti-inflammatory, and anti-malarial activities. This study aimed to examine the triglyceride (TG) reducing effects of C. guianensis-derived limonoids or other commercially available limonoids in human hepatoblastoma HepG2 cells and evaluate the expression of lipid metabolism or autophagy-related proteins by treatment with 7-deacetoxy-7-oxogedunin (DAOG; 1), a principal limonoid of C. guianensis. The gedunin-type limonoids, such as DAOG (% of control at 20 μM: 70.9 ± 0.9%), gedunin (2, 74.0 ± 1.1%), epoxyazadiradione (4, 73.4 ± 2.0%), 17β-hydroxyazadiradione (5, 79.9 ± 0.6%), 7-deacetoxy-7α-hydroxygedunin (6, 61.0 ± 1.2%), andirolide H (7, 87.4 ± 2.2%), and 6α-hydroxygedunin (8, 84.5 ± 1.1%), were observed to reduce the TG content at lower concentrations than berberine chloride (BBR, a positive control, 84.1 ± 0.3% at 30 μM) in HepG2 cells pretreated with high glucose and oleic acid. Andirobin-, obacunol-, nimbin-, and salannin-type limonoids showed no effect on the intracellular TG content in HepG2 cells. The TG-reducing effect of DAOG was attenuated by the concomitant use of compound C (dorsomorphin), an AMPK inhibitor. Further investigation on the detailed mechanism of action of DAOG at non-cytotoxic concentrations revealed that the expressions of autophagy-related proteins, LC3 and p62, were upregulated by treatment with DAOG. These findings suggested that gedunin-type limonoids from Andiroba could ameliorate fatty liver, and that the action of DAOG in particular is mediated by autophagy. [ABSTRACT FROM AUTHOR]

Andiroba seed oil (Carapa guianensis Aubl.) is widely used by traditional populations in tropical countries, especially in the Brazilian Amazon, because of its anti-inflammatory, antirheumatic, antiseptic, healing and antipyretic properties, among others, which makes it useful for the treatment, mainly, of skin afflictions and wounds. To describe the modulation of the immune system by andiroba oil (Carapa guianensis Aubl.) in inflammation and wound healing. A scoping review was performed, following the recommendations of the Joanna Briggs Institute (JBI) and PRISMA for Scoping Reviews (PRISMA-ScR). As inclusion criteria, in vitro , in vivo , ex vivo, and clinical studies were selected, in Portuguese, English, or Spanish, in thirteen databases of published studies, gray literature, and references of the included studies, which deal with immune modulation by andiroba oil in the context of the various therapeutic applications that make use of its anti-inflammatory and wound healing properties. The selection of information sources was carried out by two independent reviewers between November 2022 and January 2023. The process of data extraction and evidence analysis was conducted by four pairs of independent reviewers between January and February 2023. 22 sources of evidence were included in this scoping review, mostly scientific articles published between 2005 and 2021 with in vivo sampling. The evidence suggests that andiroba oil reduces inflammation and promotes the healing of wounds of multiple etiologies by reducing leukocyte infiltration, increasing phagocytic activity, enhancing interleukin and inflammatory cytokine activity, promoting fibroblast recovery, increasing growth factors, reducing apoptotic cells, promoting reepithelialization, as well as promoting angiogenesis, reducing edema, and stimulating the production of glucocorticoids that alleviate pain. Additionally, different formulations of the oil (such as nanoemulsions, films and gels) are more effective in modulating inflammation and wound healing compared to in natura oil. Evidence in the literature suggests that andiroba oil (Carapa guianensis Aubl.) has positive effects on immune modulation in inflammation and wound healing, which makes it a biocompound with high therapeutic potential. [Display omitted] • Andiroba oil (Carapa guianensis Aubl.) reduces inflammatory infiltrate in wounds and increases phagocyte activity. • Andiroba oil promotes wound healing and increases traction strength. • Andiroba oil systemically induces the production of glucocorticoids and reduces pain and severity of injuries. • Pure andiroba oil pure and its different presentations increase the effectiveness of inflammation, wound healing therapies. [ABSTRACT FROM AUTHOR]

The seed oil of Carapa guianensis Aublet (Andiroba) has been used in folk medicine for its insect-repelling, anti-inflammatory, and anti-malarial activities. This study aimed to examine the triglyceride (TG) reducing effects of C. guianensis-derived limonoids or other commercially available limonoids in human hepatoblastoma HepG2 cells and evaluate the expression of lipid metabolism or autophagy-related proteins by treatment with 7-deacetoxy-7-oxogedunin (DAOG; 1), a principal limonoid of C. guianensis. The gedunin-type limonoids, such as DAOG (% of control at 20 μM: 70.9 ± 0.9%), gedunin (2, 74.0 ± 1.1%), epoxyazadiradione (4, 73.4 ± 2.0%), 17β-hydroxyazadiradione (5, 79.9 ± 0.6%), 7-deacetoxy-7α-hydroxygedunin (6, 61.0 ± 1.2%), andirolide H (7, 87.4 ± 2.2%), and 6α-hydroxygedunin (8, 84.5 ± 1.1%), were observed to reduce the TG content at lower concentrations than berberine chloride (BBR, a positive control, 84.1 ± 0.3% at 30 μM) in HepG2 cells pretreated with high glucose and oleic acid. Andirobin-, obacunol-, nimbin-, and salannin-type limonoids showed no effect on the intracellular TG content in HepG2 cells. The TG-reducing effect of DAOG was attenuated by the concomitant use of compound C (dorsomorphin), an AMPK inhibitor. Further investigation on the detailed mechanism of action of DAOG at non-cytotoxic concentrations revealed that the expressions of autophagy-related proteins, LC3 and p62, were upregulated by treatment with DAOG. These findings suggested that gedunin-type limonoids from Andiroba could ameliorate fatty liver, and that the action of DAOG in particular is mediated by autophagy.

The increasing technological advances obtained both in the development of new materials and of machine tools increased the demand for the machining processes and in addition, the use of increased cutting fluids. However, it’s necessary to have characteristics that don’t harm the environment and the operator. In machining processes, cutting fluids, when properly chosen and applied, may reflect benefits during the manufacturing process. This work evaluated the performance of a commercial cutting fluid by comparing it with vegetable oil extracted from carapa guianensis in the abnt 1045 steel turning process. The cutting speed (vc), tool feed (f) and depth (ap) and the influence of the use of both of them on the metal was verified with the following variables: chip analysis, surface finish, cutting temperature and tool wear. It was observed that with the use of andiroba oil, better chip was generated for the safety of the operator, higher cutting temperatures in the piece, higher tool wear and better surface finish with a difference of 23% compared to commercial cutting fluid. Thus, the fluid from andiroba based on the conventional application demonstrated a viable alternative in the turning process of abnt 1045 steel, because it’s biodegradable and reduces petroleum-based cutting fluids. [ABSTRACT FROM AUTHOR]

The increasing technological advances obtained both in the development of new materials and of machine tools increased the demand for the machining processes and in addition, the use of increased cutting fluids. However, it’s necessary to have characteristics that don’t harm the environment and the operator. In machining processes, cutting fluids, when properly chosen and applied, may reflect benefits during the manufacturing process. This work evaluated the performance of a commercial cutting fluid by comparing it with vegetable oil extracted from carapa guianensis in the abnt 1045 steel turning process. The cutting speed (vc), tool feed (f) and depth (ap) and the influence of the use of both of them on the metal was verified with the following variables: chip analysis, surface finish, cutting temperature and tool wear. It was observed that with the use of andiroba oil, better chip was generated for the safety of the operator, higher cutting temperatures in the piece, higher tool wear and better surface finish with a difference of 23% compared to commercial cutting fluid. Thus, the fluid from andiroba based on the conventional application demonstrated a viable alternative in the turning process of abnt 1045 steel, because it’s biodegradable and reduces petroleum-based cutting fluids. [ABSTRACT FROM AUTHOR]

Abstract Two novel chukrasone-type limonoids, named Guianofruits C and D (1 and 2), a guianolide derivative named Guianofruit E (3), and four novel phragmalin–type limonoids named Guianofruits F–I (4 – 7), were isolated from the fruit oil of Carapa guianensis AUBLET (Meliaceae), a traditional medicine in Brazil and Latin American countries. Their structures were mainly elucidated based on spectroscopic analyses using 1D and 2D NMR techniques. The effects of compounds 1 – 6 on the production of NO by LPS-activated mouse peritoneal macrophages were investigated. Two new chukrasone-type limonoids, Guianofruits C (1) and D (2), exhibited moderate inhibitory activities. Graphical abstract Image 1 [ABSTRACT FROM AUTHOR]

In machining, the proper selection of cutting fluids result in benefits that vary from superior quality of the machined component to manufacturing cost. In addition, the must have characteristics that do not harm the user and the environment. In this sense, this work evaluates the effects of the vegetable base oil extracted from Carapa Guianensis in the external cylindrical turning process of the ABNT 1020 and 1045 steel grades. Highspeed steel tools were tested under roughing and finishing conditions. In addition to the physico-chemical characterization (dynamic viscosity at 40 °C and pH) of fluid, the chip form, surface finish, tool wear and workpiece temperature were evaluated. After characterization of oil, there were recorded in the dynamic viscosity at 40 °C of 0.11 Pa.s and pH of 2.3. The average roughness recorded were very close to those usually reported in the literature for finishing turning for ABNT 1020 and 1045 steels. It was also observed that the workpiece temperatures were higher when machining the ABNT 1020 steel grade under finishing condition than for other steel and conditions tested. Based on these findings, the andiroba oil delivered the conventional coolant technique demonstrated to be a technically viable alternative to conventional coolants in the turning process of ABNT 1020 and 1045 steels, because of it biodegradability characteristics and to reduce petroleumbased cutting fluids in the machining processes. [ABSTRACT FROM AUTHOR]

This work reports the preparation of nanoparticles of silk fibroin with esters obtained from the oils of two Amazonian plant species (Carapa guianensis Aublet and Bertholletia excelsa) with excellent physicochemical properties and activity against the larvae of the vector Aedes aegypti. The temporal stability of the nanoparticles was evaluated for 50 days at temperatures of 4 ºC and 32 ºC. The size of the nanoparticle was satisfactory, with sizes ranging from 207 ± 2.3 nm to 540.8 ± 23.8 nm, and PdI values ranging from 0.294 to 0.560, and zeta potential from − 37.9 ± 0.3 mV to − 62.9 ± 0.7 mV. Study of the morphology of nanoparticles, by transmission electron microscopy analysis, clearly showed spherical shapes. The nanoparticles presented slow and controlled release that induced a high mortality rate in the 3rd larval instar of Ae. aegypti , with LC 50 of 27.45 μg. mL−1 for FABE-Cg-SF-NPs and LC 50 of 21.14 μg.mL−1 for FABE-Be-SF-NPs, after 48 h of exposure. In addition, they were able to inhibit oviposition by Ae. aegypti. However, the nanoparticles did not present significant teratogenic effects on zebrafish embryos up to 72 h post-fertilization. Thus, the formation of nanoparticles by butyl esters in silk fibroin may become an (eco)alternative and effective in the control of Ae. aegypti larvae. [Display omitted] • Nanoparticle from Carapa guianensis (CgSFNp) and Bertholletia excelsa (BeSFNp) and silk fibroin. • Study oxidative stability and in vitro release of BeSFNp and CgSFNp. • Excellent larvicidal activity and oviposition-deterrence against the vector A. aegypti. • Nanoparticles did not present teratogenic effects on zebrafish embryos up to 72 h. [ABSTRACT FROM AUTHOR]

Abstract Andirobeira is an Amazonian tree, the seeds of which produce a commercially valuable oil that is used in folk medicine and in the cosmetic industry. Andiroba oil contains components with anti-inflammatory, cicatrizing and insect-repellant actions. However, virtually nothing is known of the safety of this oil for humans. The aim of this work was therefore to investigate the hematotoxicity, genotoxicity and mutagenicity of andiroba oil using the comet and micronucleus assays, and to assess its antioxidant properties and lipidome as a means of addressing safety issues. For the experiments, andiroba oil was administered by gavage for 14 consecutive days in nulliparous female Swiss mice randomly distributed in four groups: negative control and three doses of oil (500, 1000 and 2000 mg/kg/day). These doses were chosen based on recommendations of the OECD guideline no. 474 (1997). GC/MS was used to investigate the free fatty acid, cholesterol and triterpene content of andiroba oil in a lipidomic analysis. No clinical or behavioral alterations were observed throughout the period of treatment, and exposure to andiroba oil at the doses and conditions used here did not result in hematotoxic, genotoxic or mutagenic effects. Tests in vitro showed that oil sample 3 from southwestern of Brazilian Amazon had a high antioxidant capacity that may protect biological systems from oxidative stress, although this activity remains to be demonstrated in vivo.

O objetivo deste trabalho foi avaliar a variação anual da produção de frutos da andirobeira em floresta nativa e as suas implicações para o manejo florestal de uso múltiplo. Os dados foram coletados em floresta nativa, no sul do Estado de Roraima em parcela permanente de 9 ha (300 m x 300 m) onde a produção de sementes de 115 árvores foi monitorada durante quatro anos. Observou-se que a produção de sementes da população variou entre os anos de observação, sendo maio a julho o período de maior produção. Poucos indivíduos (22,6%) concentraram a maior parte da produção de sementes (80,7%) e as árvores mais produtivas apresentaram diâmetro a 1,30 m do solo entre 40 a 70 cm. Recomenda-se a adoção de um diâmetro mínimo de corte de 70 cm em planos de manejo madeireiros na região em estudo. Para o controle na coleta das sementes recomenda-se restringir a coleta aos indivíduos mais produtivos e somente no período de máxima frutificação.

Two new mexicanolide-type limonoids, carapanolides T–U (1–2), and three new phragmalin-type limonoids, carapanolides V–X (3–5), were isolated from the seeds of Carapa guianensis (andiroba). Their structures were determined on the basis of 1D- and 2D-NMR spectroscopy.

The seed oil of andiroba (Carapa guianensis, Meliaceae) was found to promote collagen synthesis in normal human dermal fibroblasts. To characterize the active constituents of this oil, the collagen synthesis-promoting activities of 10 principal limonoid constituents, gedunin (1), 6α-acetoxygedunin (2), 7-deacetoxy-7-oxogedunin (3), 7-deacetoxy-7α-hydroxygedunin (4), andirolide H (5), 6α-hydroxygedunin (6), methyl angolensate (7), 17β-hydroxyazadiradione (8), and carapanosides C (9) and R (10), were examined. Among them, 1-4, 6, 7, and 9 were found to significantly promote collagen synthesis without cytotoxicity at the effective concentrations. [ABSTRACT FROM AUTHOR]

Two novel rearranged limonoids, guianolactones A ( 1) and B ( 2), were isolated from Carapa guianensis Aubl. (Meliaceae) seeds. The structures of 1 and 2 with their absolute configurations were elucidated in detailed examinations using single-crystal X-ray diffraction analyses and 2D NMR spectra. Guianolactone A ( 1) has a novel 5/6/6/6/6 pentacyclic core including two δ-lactone and a tetrahydropyran ring, while guianolactone B ( 2) is a novel limonoid with a 6/6/5/6/6 pentacyclic core featuring a δ-lactone and a tetrahydrofuran ring. [ABSTRACT FROM AUTHOR]

The aim of this study was to evaluate clinical and histopathological aspects of topical application of pure and ozonized andiroba oil (Carapa guianensis Aublet.) on the healing process of wounds of healthy horses. Eight 6.25-cm2 wounds were surgically produced on each horse, cranial to the sacrum, being four wounds on each side of the lumbar region. In three animals, left side was used for macroscopic observations and area measurement and right side was used for histopathological analysis. For the other two animals, evaluations were inverted. Beginning of the topical treatment occurred 12 hours after surgical induction of the injuries and was maintained daily until complete healing of the wounds, using sequentially and bilaterally in the craniocaudal direction saline solution (GC), ozonized saline solution (GO), pure andiroba oil (GAP) and ozonized andiroba oil (GAO). Randomly, sequence of the treatments was modified. Macroscopic and histopathological analyses were performed at 3, 7, 14, and 21 days after surgery. Completed healing time for all wounds were recorded. A wound contraction of 67.75% for GC, 65.26% for GO, 67.91% for GAP, and 69.84% for GAO were recorded. Histopathologic evaluation revealed that wounds from the GAO and GAP had an advanced epithelialization, fibroblast proliferation and collagen deposition, moderate vascular proliferation, and presence of PMN infiltrate and discrete viewing of MN. It was possible to conclude that all treatments had benefits when comparing to control group and both pure and ozonized andiroba oil can be good options for wound treatment in horses.

A novel gedunin and two novel phragmalin-type limonoids, named carapanolides J–L (compounds 1–3) as well as a known gedunin-type limonoid 4 were isolated from the seeds of Carapa guianensis (andiroba). Their structures were determined on the basis of 1D and 2D NMR spectroscopy and HRFABMS. Compounds 1–4 were evaluated for their effects on the production of NO in LPS-activated mouse peritoneal macrophages.

A capacidade de utilização da luz varia entre as espécies, e o sucesso de cada indivíduo depende de suas respostas morfoanatômicas. Este estudo avaliou a influência de diferentes intensidades luminosas sobre a anatomia foliar de mudas de Carapa guianensis Aubl. Folhas sadias do segundo e terceiro nós foram coletadas de plantas jovens desenvolvidas em quatro níveis de sombreamento: 30%, 50%, 70% e 0% (pleno sol), durante oito meses de experimento. Análises anatômicas foram feitas sob Microscopia Óptica (MO), a partir de lâminas temporárias e permanentes e sob Microscopia Eletrônica de Varredura (MEV). A densidade estomática não apresentou diferenças significativas. As dimensões estomáticas e a espessura dos tecidos da lâmina foliar foram maiores com o aumento da intensidade luminosa. C. guianensis apresenta plasticidade anatômica, possibilitando a sobrevivência na floresta sob distintas condições luminosas.

The factors that determine the existence of tropical forests dominated by a single species (monodominated forests) have been the subject of debate for a long time. It has been hypothesized that the low frequency of disturbances in monodominated forests and the tolerance to shade of the monodominant species are two important factors explaining the prolonged dominance of a single species. We determined the role of these two factors by examining the effects of logging activities on the floristic composition and seedling dynamics in a Prioria copaifera dominated forest in Southeastern Costa Rica. We determined the floristic composition for trees ≥2.5cm DBH and the associated recruitment, survival and mortality of tree canopy seedlings in two sites logged two (L-02) and 12 years (L-12) prior to sampling and an unlogged forest (ULF). Our results showed that L-02 stands had lower species richness (25 species) than the L-12 and ULF stands (49 and 46 species, respectively). As expected, we found significant logging effects on the canopy structure of the altered forests, particularly when comparing the L-02 and the ULF stands. Seedling density was higher in ULF (0.96 seedlings/m²) than in the L-02and L-12 stands (0.322 and 0.466 seedlings/m², respectively). However, seedling mortality was higher in the ULF stands (54%) than in the L-02 (26%) and L-12 (15%) stands. P. macroloba in L-02 was the only species with abundant regeneration under P. copaifera in L-02 stand, where it accounted for 35% of the seedlings. Despite the reduction in seedling abundance observed after logging, P. copaifera seems to maintain large seedling populations in these forests, suggesting that this species maintains its dominance after logging disturbances. Our findings challenge the hypothesis that the regeneration of monodominant species is not likely to occur under heavily disturbed canopy conditions. Rev. Biol. Trop. 62 (1): 347-357. Epub 2014 March 01.

The transport of seeds by water, i.e. hydrochory, is a key mechanism of long-distance dispersal constrained by the attributes of the seed and hydrodynamics. In the freshwater Amazon estuary, river hydrodynamics are influenced by seasonal changes in precipitation and tidal cycles. It is not known to what extent a hydrodynamic model may be able to predict seed dispersal., Here we parameterised a simulation model (SisBaHia) to estimate maximum seed dispersal distances per tidal cycle, which were then compared with data from in situ seed dispersal experiments. The study was conducted along a 27-km stretch of a tributary of the Amazon estuary, using the seeds of a widely distributed riparian tree- Carapa guianensis (Meliaceae)., Based on the simulation model, maximum potential seed dispersal distance was higher in the rainy season ( c. 8.7 km) when compared with the dry season (5.6 km), for one tidal cycle (12 hr). The seeds of C. guianensis were dispersed further during the ebb than flood tide during the rainy season, the period of seed dispersal. Average dispersal distances observed in seed dispersal experiments conducted during the rainy season, and those predicted by SisBaHia for the same period were within the same order of magnitude., The results of this study confirm that the period of higher precipitation provides favourable hydrological conditions for hydrochory in the Amazon river-estuary complex. The fact that the time taken for the tide to fall is longer in relation to the time taken for it to rise also favours the arrival of the seeds in the main channel of the Amazon, thereby increasing the probability of long-distance dispersal events. [ABSTRACT FROM AUTHOR]

The objective of this study was to evaluate the annual variation in seed yield of crabwood, and discuss implications for multiple use management of the species. Data were collected in a forest area in the southern of Roraima State in a permanent plot of 9 ha (300 m x 300 m) with a natural population of crabwood. Seed production was monitored of 115 trees during four years. Seed yield varied among years. May to July was the period of bigger yield. Few trees (22.6%) concentrated the bigger part of seeds yield (80.7%) and the most productive trees had diameter at 1.30 m above ground level between 40 cm - 70 cm. Therefore we recommend 70 cm as minimum cutting diameter for wood exploitation. For sustainable crabwood seed management we recommend to restrict seed collection from the most productive trees and only during the period of maximum seed dispersal. [ABSTRACT FROM AUTHOR]

Two new phragmalin-type limonoids, Carapanosins A and B (1 and 2), and a new gedunin-type limonoid, Carapansin C (3), together with five known limonoids (4-8) were isolated fromthe oil of Carapa guianensis AUBLET (Meliaceae) seeds, a traditional medicine in Brazil and LatinAmerican countries. Their structures were elucidated on the basis of spectroscopic analyses using 1D and 2D NMR techniques and HRFABMS. Compounds 1-8 were evaluated for their effects on the production of NO in LPS-activated mouse peritoneal macrophages. The NO inhibitory assay suggested that Compounds 3, 6, and 8 may be valuable as potential inhibitors of macrophage activation. [ABSTRACT FROM AUTHOR]

The objective of this work was to estimate the mating system parameters of a andiroba (Carapa guianensis) population using microsatellite markers and the mixed and correlated mating models. Twelve open‑pollinated progeny arrays of 15 individuals were sampled in an area with C. guianensis estimated density of 25.7 trees per hectare. Overall, the species has a mixed reproductive system, with a predominance of outcrossing. The multilocus outcrossing rate (t m = 0.862) was significantly lower than the unity, indicating that self‑pollination occurred. The rate of biparental inbreeding was substantial (t m ‑ t s = 0.134) and significantly different from zero. The correlation of selfing within progenies was high (r s = 0.635), indicating variation in the individual outcrossing rate. Consistent with this result, the estimate of the individual outcrossing rate ranged from 0.598 to 0.978. The multilocus correlation of paternity was low (r p(m) = 0.081), but significantly different from zero, suggesting that the progenies contain full‑sibs. The coancestry within progenies (Θ = 0.185) was higher and the variance effective size (Ne(v) = 2.7) was lower than expected for true half‑sib progenies (Θ = 0.125; Ne(v) = 4). These results suggest that, in order to maintain a minimum effective size of 150 individuals for breeding, genetic conservation, and environmental reforestation programs, seeds from at least 56 trees must be collected.

This study aims to describe the morphometry of Andiroba (Carapa guianensis Aubl), Brasil nut tree (Bertholletia excelsa HBK), Copaíba (Copaifera langsdorffii Desf.) Mogno (Swietenia macrophylla King.) and simulate the vital space for it to grow without competition in agroforestry plantations. Data were collected in 20 agroforestry (SAF’s) considered productive age (16.5 years) of Project RECA (Economic Reforestation Consortium and Compacted), the municipality of Porto Velho, Rondônia. The deployment of the SAF’s occurred through the removal of vegetation through the process of clearing and burningof native forests. Morphometric data were collected randomly from individuals with DBH > 10 cm of four tree species in onehectare of each farm, for a total sample area of 20 ha (20 properties). The sample was composed by 25 individuals of Andiroba,40 of Brasil nut tree, 23 of Copaíba and 46 of Mogno. Andiroba was very similar to Mogno in relation to Cup Percentage (PC),Coverage Index (AI) and Cup Form (FC), both showed potential for higher density plantations with timber purposes. The Brasilnut tree and Copaíba had the highest values of the FC (1.66, 1.79) and Crown Area (92.60, 57.51), respectively, showing frondscrowns, silvicultural interesting features for the extraction of seeds. Was simulated living space for the four species developwithout competition between cups. It was concluded that the four species have potential for planting for extraction of timberand non-timber forest in areas subject to degradation and deforestation in the Amazon.ResumoO presente estudo visa descrever a morfometria das espécies Andiroba (Carapa guianensis Aubl), Castanheira-do-Brasil (Bertholletia excelsa H.B.K.), Copaíba (Copaifera langsdorffii Desf.) e Mogno (Swietenia macrophylla King.) e simular o espaço vital para que as mesmas cresçam sem concorrência em plantios agroflorestais. Os dados foram coletadosem vinte sistemas agroflorestais (SAF’s) em idade considerada produtiva (16,5 anos) do Projeto RECA (Reflorestamento Econômico Consorciado e Adensado) no município de Porto Velho, Rondônia. A implantação dos SAF´s ocorreu mediante a supressão da vegetação por meio do processo de derrubada e queima da floresta nativa. Foram coletados aleatoriamente dados morfométricos de indivíduos com DAP > 10 cm das quatro espécies florestais em 1 ha de cada propriedade rural , totalizando uma área amostral de 20 ha (20 propriedades). A amostragem foi composta por 25 indivíduos de Andiroba, 40 de Castanheira-do-Brasil, 23 de Copaíba e 46 de Mogno. A Andiroba foi bastante semelhante ao Mogno em relação à Porcentagem de Copa(PC), Índice de Abrangência (IA) e Forma de Copa (FC) e ambas demonstraram potencialidade para plantios adensados com fins madeireiros. A Castanheira-do-Brasil e a Copaíba obtiveram os maiores valores de FC (1,66; 1,79) e Área de Copa (92,60;57,51), respectivamente, indicando copas frondosas, características silviculturais interessantes para o extrativismo de sementes. Foi simulado o espaço vital para que às quatro espécies desenvolvessem sem competição entre copas. Concluiu-se que, ambas as espécies apresentaram potencial para plantio visando à extração de produtos madeireiros e não madeireiros em áreas florestais submetidas ao desmatamento e degradação na Amazônia.

Low coverage MiSeq genome sequencing and restriction associated DNA sequencing (RADseq) were used to identify nuclear and plastid SNP and INDEL genetic markers in Carapa guianensis. 261 genetic markers including 237 nuclear SNPs, 22 plastid SNPs, and 2 plastid INDELs are described based on 96 genotyped individuals from French Guiana, Brazil, Peru, and Bolivia. The best 117 SNPs for identifying population structure and performing individual assignment are assembled into four multiplexes for MassARRAY genotyping. [ABSTRACT FROM AUTHOR]

Six limonoids were isolated in hexane extract obtained from the seeds and pericarps of Carapa guianensis. The structures of the limonoids were determined based on the analysis of High Resolution Mass Spectroscopy and Nuclear Magnetic Resonance (uni-and bi-dimensional experiments) data. This is the first report of isolation of the limonoid 6α-acetoxy-7-deacetilgedunin from the seeds of the C. guianensis species. The limonoid 6-hydroxy-methyl angolensate was also described for the first time in this species.

A novel nor-phragmalin-type limonoid, named carapanosin D (1), and two novel mexicanolide-type limonoids, carapanosins E (2) and F (3), were isolated from the seed oil of andiroba (Carapa guianensis Aublet), a traditional medicine in Brazil and Latin American countries. Their structures were unambiguously determined on the basis of spectroscopic analyses using one-dimensional (1D) and two-dimensional (2D) NMR techniques and High resolution Fast Atom Bombardment Mass Spectrometry (HRFABMS). Compounds 1–3 were evaluated for their effects on the production of nitric oxide (NO) in Lipopolysaccharide (LPS)-activated mouse peritoneal macrophages. The NO inhibitory assay suggested that compounds 2 and 3 have high potency as inhibitors of macrophage activation.

O objetivo deste trabalho foi investigar o desempenho fotossintético de plantas jovens de andiroba (Carapa guianensis), submetidas à deficiência hídrica e à reidratação. As plantas foram irrigadas diariamente, em casa de vegetação, durante 15 dias. Após aclimatação, as plantas foram separadas em dois tratamentos: plantas irrigadas e não irrigadas. Quando a resposta fotossintética das plantas não irrigadas alcançou valores próximos a zero, as plantas foram reidratadas. A cada sete dias, durante 21 dias, foram realizadas as determinações das trocas gasosas e da fluorescência da clorofila a. O potencial hídrico foliar foi determinado no início e no fim do experimento. As taxas de fotossíntese líquida, condutância estomática e transpiração se reduziram em 88, 89 e 89%, respectivamente, após 21 dias de supressão da irrigação. Quanto às variáveis da fluorescência da clorofila a, observaram-se reduções de 27 a 58%. O potencial hídrico foliar das plantas foi reduzido em mais de quatro vezes, após 21 dias de deficiência hídrica. De quatro a oito dias após a reidratação, as plantas recuperaram as características fotossintéticas e o potencial hídrico foliar, o que indica que plantas jovens de andiroba apresentaram alta plasticidade fisiológica em relação ao estresse hídrico.The objective of this work was to investigate the photosynthetic performance of young andiroba plants (Carapa guianensis) submitted to water stress and rewetting. The plants were irrigated daily in greenhouse conditions for 15 days. After acclimatization, the plants were separated randomly in two treatments, irrigated and non-irrigated plants. When the photosynthesis of the non-irrigated plants reached values close to zero, the plants were rewetted. Measurements of gas exchanges and chlorophyll a fluorescence were recorded on seven-day intervals, during 21 days. Plant water potentials were determined at the beginning and at the end of the experiment. Net photosynthesis, stomatal conductance, and transpiration rates were reduced by 88, 89, and 89%, respectively, after 21 days of water stress. In relation to chlorophyll a, fluorescence variables were reduced 27 to 58%. The plant water potential was reduced more than four times by 21 days of stress. With rewetting, seedlings recovered their photosynthetic characteristics in four to eight days as well as their water potential, indicating that young andiroba plants exhibited high physiological plasticity to water stress.

Plants react to changes in light and hydrological conditions in terms of quantity and composition of chloroplastidic pigments, which affects the photosynthetic properties and consequently the accumulation of plant biomass. Thus, the chloroplastidic pigment concentration and chlorophyll a fluorescence of three Amazonian species (Bertholletia excelsa, Carapa guianensis e Dipteryx odorata) were investigated in sun and shade leaves form the tree crown collected during two distinct periods of precipitation (dry and rainy seasons). Pigment contents were determined by spectrophotometry and fluorescence variables were determined using a portable fluorometer. The results demonstrated that the species showed high concentrations of Chl a, Chl b e Chl total during the wet season in relation to the dry season, especially in shade leaves. A higher concentration of carotenoids was found in B. excelsa, when compared with leaves of C. guianensis and D. odorata. In leaves of B. excelsa and D. odorata no significant difference was found in relation to the photochemistry of photosystem II (Fv/Fm) between the wet and dry seasons. In conclusion, the three species react differently to variations in the light and precipitation conditions regarding light capture, aspects that might be considered in the management of forest plantations.As plantas respondem a mudanças nas condições de luz e na disponibilidade hídrica em termos da quantidade e composição dos pigmentos cloroplastídicos, o que afeta as propriedades fotossintéticas e, conseqüentemente, o acúmulo de biomassa das espécies. Assim, a concentração de pigmentos cloroplastídicos e a fluorescência da clorofila a de três espécies arbóreas (Bertholletia excelsa, Carapa guianensis e Dipteryx odorata) da Amazônia foi investigada em folhas sombreadas e não-sombreadas da copa das árvores e em dois períodos distintos de precipitação (chuvoso e seco). As concentrações de pigmentos foram determinadas por espectrofotometria e as variáveis de fluorescência, por meio de um fluorômetro portátil. Os resultados indicaram que as espécies estudadas exibiram maiores concentrações de Chl a, Chl b e Chl total no período chuvoso, em comparação com o período seco, em especial em folhas de sombra. As maiores concentrações de carotenóides foram observadas em B. excelsa, em comparação com as folhas de C. guianensis e D. odorata. Nas folhas de B. excelsa e D. odorata, não foram encontradas diferenças significativas em relação à fotoquímica do fotossistema II (Fv/Fm), entre os períodos chuvoso e seco. Conclui-se que as três espécies respondem de modo diferente à variação da luz e às condições distintas de precipitação quanto à captura de luz, aspecto que deveria ser considerado no manejo de plantios florestais.

O objetivo deste trabalho foi avaliar a diversidade genética em duas populações de Carapa guianensis Aubl. (andiroba), no Estado do Acre, e comparar os parâmetros de diversidade com os observados em outras populações da espécie (no Brasil: Flona Tapajós, PA, Porto Acre, AC; e na Costa Rica). Foram avaliados 77 indivíduos adultos com sete locos polimórficos de microssatélites. Observaram-se 51 alelos nas duas populações, em que o número efetivo de alelos por loco (Âe = 3,2) foi inferior ao número médio de alelos por loco (Â = 7,3), o que indica elevado número de alelos com baixa freqüência. Os valores estimados de f não diferiram de zero, o que mostra que não ocorre endogamia nas populações. A taxa de cruzamento aparente foi alta (t a = 1,11 na população Porto Acre, e t a= 0,88 na de Rio Branco), resultado indicador de que a espécie se reproduz por alogamia. Foi observado, por meio das estimativas de Â, He (diversidade gênica) e Ne (número efetivo populacional) que as populações de andiroba, comparadas neste trabalho, tiveram padrões de diversidade semelhantes, porém, proporções de alelos raros diferentes.The objective of this work was to evaluate the genetic diversity of two Carapa guianensis Aubl. (crabwood) populations, in the State of Acre, Brazil, and to compare the diversity estimations with those obtained in other populations of the species (in Brazil: Flona Tapajós, PA, Porto Acre, AC; and in Costa Rica). Seventy-seven individuals were assessed using seven polymorphic microsatellite loci. Fifty-one alleles were observed in the two populations, in which the effective number of alleles per locus (Âe = 3.2) was lower than the average number of alleles per locus (Â = 7.3), which indicates a high number of low frequency alleles. The estimated f values did not differ from zero, showing that inbreeding does not occur in these populations. The apparent outcrossing rate was high for both populations (t a = 1.11 in Porto Acre population, and t a = 0.88 in Rio Branco), indicating that this species reproduces by outcrossing. Comparing the estimates of Âe, He (gene diversity) and Ne (effective population number), it was observed that the general patterns of genetic diversity were similar. However, the number of rare alleles differ between populations.

Big-leaf mahogany is the world's most valuable widely traded tropical timber species and Near Infrared Spectroscopy (NIRS) has been applied as a tool for discriminating its wood from similar species using multivariate analysis. In this study four look-alike timbers of Swietenia macrophylla (mahogany or big-leaf mahogany), Carapa guianensis (crabwood), Cedrela odorata (cedar or cedro) and Micropholis melinoniana (curupixá) have been successfully discriminated using NIRS and Partial Least Squares for Discriminant Analysis using solid block and milled samples. Species identification models identified 155 samples of S. macrophylla from 27 countries with a correct classification rate higher than 96.8%. For these specimens, the NIRS spectrum variation was more powerful for species identification than for determining provenance of S. macrophylla at the country level. [ABSTRACT FROM AUTHOR]

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Three gedunin-type limonoids, gedunin (1), 6α-acetoxygedunin (2), and 7-deacetoxy-7-oxogedunin (3), which were isolated from the seed and flower oils of andiroba (Carapa guianensis Aublet, Meliaceae), exhibited hepatoprotective effects at doses of 25 mg/kg, p.o. against D-galactosamine (D-GalN)/lipopolysaccharide (LPS)-induced liver injury in mice. To characterize the mechanisms of action of 1-3 and clarify the structural requirements for their hepatoprotective effects, 17 related limonoids (1-17) isolated from the seed and/or flower oils of C. guianensis were examined in in vitro studies assessing their effects on (i) D-GalN-induced cytotoxicity in primary cultured mouse hepatocytes, (ii) LPS-induced nitric oxide (NO) production in mouse peritoneal macrophages, and (iii) tumor necrosis factor-α (TNF-α)-induced cytotoxicity in L929 cells. The mechanisms of action of 1-3 are likely to involve the inhibition of LPS-induced macrophage activation and reduced sensitivity of hepatocytes to TNF-α; however, these compounds did not decrease the cytotoxicity caused by D-GalN. In addition, the structural requirements of limonoids (1-17) for inhibition of LPS-induced NO production in mouse peritoneal macrophages and TNF-α-induced cytotoxicity in L929 cells were evaluated. [ABSTRACT FROM AUTHOR]

Nine limonoids were isolated from Carapa guianensis and Cedrela fissilis. Among them, 1,2-dihydro-3beta-hydroxy-7-deacetoxy-7-oxogedunin is a new compound. Moreover, the assignments of some chemical shifts of xyloccensin k have been corrected and ¹H NMR data of 7-deacetylgedunin have been assigned for the first time. These isolated limonoids were assayed on Atta sexdens rubropilosa workers showing moderate insecticidal activities.

In this work, andiroba oil extraction ( Carapa guianensis ) was investigated using pressurized n -butane as solvent at 25, 35 and 45 °C and pressures of 7, 10 and 13 bar. Andiroba oil yield as high as 18 wt% was obtained at the lowest temperature and pressure (25 °C and 7 bar) for an extraction period of 45 min. Regarding chemical composition, the major components observed in the extracts were palmitic and oleic acids, while for the phenolic compounds values between 11.2 and 35.7 (mg EAG/100 g) were experimentally observed. For the antioxidant activity, DPPH radical scavenging method employed for the extraction conditions of 25 °C and 13 bar and 45 °C/7 bar provided inhibition percentages of 22.2% and 17.4%, respectively. Extraction with n -butane thus showed to be a promising alternative technique to conventional extraction methods, as very mild operating conditions and eco-friendly solvent can be used to provide good results without any residues in the final product. [ABSTRACT FROM AUTHOR]