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Sesquiterpene compounds are applied as permeation promoters in topical formulations. However, studies exploring their impact on nanostructured systems, changes in permeation profile, and consequently, its biological activity are restricted. This study aimed to investigate the correlation between the skin permeation of the major sesquiterpenes, beta-caryophyllene, and caryophyllene oxide from the oleoresin of Copaifera multijuga, after delivery into topical nanoemulgels, and the in vivo antiedematogenic activity. First, ten nanoemulgels were prepared and characterized, and their in vitro permeation profile and in vivo anti-inflammatory activity were evaluated. In equivalent concentrations, ß-caryophyllene permeation was greater from oleoresin nanoemulgels, resulting in greater in vivo antiedematogenic activity. However, an inverse relationship was observed for caryophyllene oxide, which showed its favored permeation and better in vivo anti-inflammatory effect carried as an isolated compound in the nanoemulgels. These results suggest that the presence of similar compounds may interfere with the permeation profile when comparing the profiles of the compounds alone or when presented in oleoresin. Furthermore, the correlation results between the permeation profile and in vivo antiedematogenic activity corroborate the establishment of beta-caryophyllene as an essential compound for this pharmacological activity of C. multijuga oleoresin.

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Cadmium is a metal that can affect the male reproductive process, possibly leading to infertility. In contrast, beta-caryophyllene (BC) is a sesquiterpene that has shown antigenotoxic, anticancer, and antioxidant properties. Therefore, the aim of the present study was to determine the protective effect of BC against the deleterious effects of cadmium chloride (CC) on various mouse testicular and sperm parameters. We tested three doses of BC (20, 200, and 400 mg/kg) given before and during exposure to 3 mg/kg CC (six days after a single administration). Our results show significant alleviation of the damage induced by CC after the three doses of BC. Regarding the sperm concentration and morphology, the protection with the high dose was complete, and regarding sperm mobility and viability, the protection was more than 74%. In the comet assay, the highest dose showed a reduction of 92.5% in the damage induced by CC, and regarding the number of micronuclei in the spermatids, the reduction was 83.3%. In the oxidative evaluation, regarding sperm lipoperoxidation, the improvement was complete with the high dose, and in the ABTS.+ test, the improvement in the response to the BC high dose was 26.3%. Regarding testicular lipoperoxidation and protein oxidation, the protective effects of the high BC dose were 87.6% and 89.9%, respectively. We also found that BC protected against the histological and morphometric alterations induced by CC. Therefore, our study clearly demonstrates the beneficial, chemopreventive effect of BC against the mouse sperm and testicular alterations induced by CC.

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ß-caryophyllene is a sesquiterpene present in the oil of many plant species, such as Copaifera sp., which has been shown to possesses potent anti-inflammatory action; however, its healing activity remains under study. The objectives of the present study were to produce a nanoemulsion containing ß-caryophyllene followed by a hydrogel containing nanoemulsified ß-caryophyllene, to evaluate the permeation profile in vitro, and to assess the in vivo healing activity, which is so far unexplored in the literature for pure ß-caryophyllene and in pharmaceutical formulation. The nanoemulsion was obtained through high-pressure homogenization and the hydrogel by direct dispersion with hydroxyethylcellulose. Both formulations were characterized according to droplet size, polydispersity index, volume-weighted mean diameters, particle distribution, droplets diameters tracking, zeta potential, viscosity and bioadhesion behavior. ß-caryophyllene content was determined by gas chromatography coupled with mass spectrometry (GC/MS). Both formulations presented a nanometric droplet size, negative zeta potential, high ß-caryophyllene content, and were stable for 60 days. In agreement with the viscosity results, the hydrogel containing the ß-caryophyllene nanoemulsion showed superior bioadhesiveness than the nanoemulsion. The skin permeation study in Franz cells demonstrated that isolated ß-caryophyllene was unable to cross the stratum corneum and that its nanoemulsification promoted its permeation. On the other hand, in the simulated deeply wounded skin (dermis), no significant differences were observed between the formulations and isolated ß-caryophyllene with respect to the amount of marker retention in the dermis, suggesting saturation of this skin layer. For the study of healing activity, the dorsal wound model was performed with an evaluation of the lesion size, anti-inflammatory markers, and antioxidant activity. The initial closure of the wound was achieved sooner in the group treated with the hydrogel containing the ß-caryophyllene nanoemulsion, indicating its anti-inflammatory effect. The histological analysis indicated that on day 12 day of the lesion, the hydrogel presented similar results to those of the positive control group (Dersani® oil), proving effectiveness in cutaneous tissue repair.

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The peel components and juice quality of three mandarin hybrids were investigated in this study. Peel components were extracted using the cold-press method and analyzed using GC-FID and GC-MS. Total soluble solids, total acid, pH value, ascorbic acid as well as density were determined in juice obtained from mandarin hybrids. Twenty-six, thirty-five and nineteen peel components were identified in Fortune, Robinson and Osceola respectively including: aldehydes, alcohols, esters, monoterpenes, sesquiterpenes and other components. The major components were limonene, γ-terpinene, (E)-ß-ocimene, ß-myrcene, sabinene, linalool and α-Pinene. Among the three scions examined, Fortune showed the highest content of aldehydes and Robinson showed the highest content of TSS. This study shows that scion has a profound influence on aldehyd and TSS that are important to quality improvement.

Los componentes de la cáscara y la calidad del jugo de tres híbridos de mandarina fueron investigados en este estudio. Los componentes de la cáscara fueron extraídos por el método de prensado en frío y se analizaron mediante GC-FID y GC-MS. el total de sólidos solubles, acidez total, pH, ácido ascórbico, así como la densidad se determinaron en el jugo obtenido a partir de híbridos de mandarina. Veintiséis, treinta y cinco y diecinueve componentes de la cáscara de Fortuna, Robinson y Osceola respectivamente fueron identificados, incluyendo: aldehídos, alcoholes, ésteres, monoterpenos, sesquiterpenos y otros componentes. Los componentes principales eran limoneno, γ-terpineno, (E) -ß-ocimeno, ß-mirceno, sabineno, linalool y α-pineno. Entre los tres vástagos examinados, Fortune mostró el mayor contenido de aldehídos y Robinson mostró el mayor contenido de SST. Este estudio muestra que el vástago tiene una profunda influencia en aldehído y SST que son importantes para mejorar la calidad.

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Beta-caryophyllene (BCP) is a phytocannabinoid whose neuroprotective activity has been mainly associated with selective activation of cannabinoid-type-2 (CB2) receptors, inhibition of microglial activation and decrease of inflammation. Here, we addressed the potential of BCP to induce neuritogenesis in PC12 cells, a model system for primary neuronal cells that express trkA receptors, respond to NGF and do not express CB2 receptors. We demonstrated that BCP increases the survival and activates the NGF-specific receptor trkA in NGF-deprived PC12 cells, without increasing the expression of NGF itself. The neuritogenic effect of BCP in PC12 cells was abolished by k252a, an inhibitor of the NGF-specific receptor trkA. Accordingly, BCP did not induce neuritogenesis in SH-SY5Y neuroblastoma cells, a neuronal model that does not express trkA receptors and do not respond to NGF. Additionally, we demonstrated that BCP increases the expression of axonal-plasticity-associated proteins (GAP-43, synapsin and synaptophysin) in PC12 cells. It is known that these proteins are up-regulated by NGF in neurons and neuron-like cells, such as PC12 cells. Altogether, these findings suggest that BCP activates trka receptors and induces neuritogenesis by a mechanism independent of NGF or cannabinoid receptors. This is the first study to show such effects of BCP and their beneficial role in neurodegenerative processes should be further investigated.

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Aloysia polystachya and Lippia turbinata are medicinal and aromatic plants. Nevertheless, there are few reports in literature concerning the biological properties of species that grow in northeastern Argentina. The antibacterial activity and the chemical composition of both essential oils were evaluated in this work. The extraction was performed by steam distillation and their volatile compounds were determined by gas chromatography/mass spectrometry. The antibacterial activity was evaluated by disc diffusion and broth microdilution assay. The main compounds were carvone (78.9 percent) and limonene (14.2 percent) in A. polystachya and carvone (80.77 percent), limonene (8.73 percent), beta- caryophyllene (2.13 percent) and 1,8-cineole (1.70 percent) in L. turbinata. Both essential oils were bactericide against Escherichia coli ATCC 35218 and clinical isolates of Enterobacter cloacae and Klebsiella pneumoniae. Essential oil of A. polystachya was also bactericide against Staphylococcus aureus ATCC 29212, S. aureus ATCC 25923 and clinical strain of S. aureus methicillin susceptible.

Aloysia polystachya y Lippia turbinata son plantas medicinales y aromáticas. Hay pocos informes en la literatura sobre las propiedades biológicas de especies que crecen en el nordeste de Argentina. La actividad antibacteriana y la composición química de ambas especies se evaluaron en este trabajo. La extracción se realizó por destilación con vapor y sus compuestos se determinaron por cromatografía gaseosa/espectrometría de masa. La actividad antibacteriana fue evaluada por difusión en discos y microdilución en caldo. Los principales compuestos fueron carvona (78.9 por ciento) y limoneno (14.2 por ciento) en A. polystachya y carvona (80.77 por ciento), limoneno (8.73 por ciento), beta-cariofileno (2.13 por ciento) y 1,8-cineol (1.70 por ciento) en L. turbinata. Ambos aceites esenciales fueron activos contra Escherichia coli ATCC 35218 y aislamientos clínicos de Enterobacter cloacae y Klebsiella pneumoniae. El aceite esencial de A. polystachya fue bactericida contra Staphylococcus aureus ATCC 29212, S. aureus ATCC 25923 y aislamientos clínicos de S. aureus sensible a meticilina.

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The leaves of Myrcia tomentosa were collected from five sites and four different months in the Brazilian Cerrado and their essential oils were obtained by hidrodistillation and analyzed by GC/MS. The aim of this work was to evaluate the influence of environmental factors on essential oils composition in the leaves of M. tomentosa. The results were submitted to stepwise Multiple Regression and Canonical Correlation Analysis that indicated a relationship between compounds in essential oils and some environmental factors (foliar nutrients, soil nutrients and climatic data). Cluster Analysis indicated a high chemovariability in the essential oils from different sites, also showed that the collection time had a minor effect on oil composition.

Las hojas de Myrcia tomentosa se obtuvieron de cinco sitios diferentes y cuatro meses en el Cerrado brasileño y sus aceites esenciales fueron obtenidos por hidrodistillation y analizados por GC/MS. El objetivo de este trabajo fue evaluar la influencia de los factores ambientales sobre la composición de los aceites esenciales en las hojas de M. tomentosa. Los resultados fueron sometidos a múltiples etapas de regresión y análisis de correlación canónica indicó que la relación entre los compuestos en los aceites esenciales y algunos factores ambientales (nutrientes foliares, fertilizantes y datos climáticos). El análisis de agrupamiento indicó chemovariability un alto en los aceites esenciales de diferentes sitios, también mostró que el equipo de recolección tuvo un efecto menor sobre la composición del aceite.

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Essential oils obtained from the aerial parts of Dicypellium manausense, Mezilaurus duckei, Mezilaurus itauba and Pleurothyrium vasquezii collected at the Ducke Forest Reserve (Manaus, Brazil) were obtained by hydrodistillation and analyzed by CG-FID and GC-MS. Essential oil yields ranged from 0.1 to 0.2 percent (w/w of dry material). The major components were beta-caryophyllene in the leaves of D. manausense (39.5 percent), leaves and branches of M. duckei (32.6 and 18.4 percent, respectively) and branches of M. itauba (51.8 percent); and germacrene D in the leaves of D. manausense (6.7 percent), branches of M. itauba (9.1 percent) and leaves and branches of P. vasquezii (15.6 and 8.0 percent, respectively). This paper describes for the first time the composition of these essential oils.

Os óleos essenciais obtidos das partes aéreas de Dicypellium manausense, Mezilaurus duckei, Mezilaurus itauba e Pleurothyrium vasquezii coletadas na Reserva Florestal Ducke (Manaus, Brasil) foram obtidos por hidrodestilação e analisados por CG-DIC e CG-EM. Os rendimentos dos óleos variaram de 0,1 a 0,2 por cento (m/m de material seco). Os principais componentes foram beta-cariofileno nas folhas de D. manausense (39,5 por cento), folhas e galhos de M. duckei (32,6 e 18,4 por cento, respectivamente) e galhos de M. itauba (51,8 por cento) e germacreno D na folhas de D. manausense (6,7 por cento), galhos de M. itauba (9,1 por cento) e folhas e galhos de P. vasquezii (15,6 e 8,0 por cento, respectivamente). Este trabalho descreve pela primeira vez a composição desses óleos.

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O óleo essencial obtido por hidrodestilação das folhas de Eugenia punicifolia, coletados a partir de duas regiões de Matas Serranas do Estado de Pernambuco (Serra Negra e Brejo da Madre de Deus), foi analisado por CG/EM. O monoterpeno oxigenado, linalol (SN: 44,0 por cento, BMD: 61,2 por cento), foi o componente principal do óleo de ambas amostras. Cerca de 66,2 por cento da constituição dos voláteis da amostra proveniente de SN e 74,2 por cento de BMD referem-se aos monoterpenos oxigenados, enquanto 33,6 por cento da amostra de SN e 20,5 por cento de BMD são sesquiterpenos oxigenados, sendo o b-cariofileno o mais abundante (SN: 22,7 por cento, BMD: 16,2 por cento). Com exceção do a-cadinol, presente apenas no óleo proveniente do Brejo da Madre de Deus, a constituição química de ambas as amostras foi à mesma, variando apenas o percentual relativo de seus constituintes.

The essential oils obtained from the leaves of Eugenia punicifolia by hydrodistillation, which were collected from two different locations of Pernambuco (Serra Negra and Brejo da Madre de Deus), have been investigated by GC/MS. Linalol was found to be the main component of this oil from SN (44,0 percent) and BMD (61,2 percent). About 66,2 percent of the oil constituents from SN and 74,2 percent from BMD are oxygenated monoterpenes, with predominance of beta-cariofileno (SN: 22,7 and BMD: 16,2 percent). With exception of a-cadinol, present only in the oils from plants colleted in Brejo da Madre de Deus, the chemical composition of both samples was quite similar, the only difference was the relative content among their components.