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Bursera fagaroides, popularly used in México, possesses bioactive lignans. These compounds are low in the bark, and its extraction endangers the life of the trees. The aim of the present investigation was to search for alternative sources of cytotoxic compounds in B. fagaroides prepared as leaves and in vitro callus cultures. The friable callus of B. fagaroides was established using a combination of plant growth regulators: 4 mgL−1 of 2,4-dichlorophenoxyacetic acid (2,4-D), 1 mgL−1 Naphthaleneacetic Acid (NAA) and 1 mgL−1 Zeatin. The maximum cell growth was at day 28 with a specific growth rate of μ = 0.059 days−1 and duplication time td = 11.8 days. HPLC quantification of the dichloromethane callus biomass extract showed that Scopoletin, with a concentration of 10.7 µg g−1 dry weight, was the main compound inducible as a phytoalexin by the addition of high concentrations of 2,4-D, as well as by the absence of nutrients in the culture medium. In this same extract, the compounds γ-sitosterol and stigmasterol were also identified by GC-MS analysis. Open column chromatography was used to separate and identify yatein, acetyl podophyllotoxin and 7′,8′-dehydropodophyllotoxin in the leaves of the wild plant. Cytotoxic activity on four cancer cell lines was tested, with PC-3 prostate carcinoma (IC50 of 12.6 ± 4.6 µgmL−1) being the most sensitive to the wild-type plant extract and HeLa cervical carcinoma (IC50 of 72 ± 5 µgmL−1) being the most sensitive to the callus culture extract. [ABSTRACT FROM AUTHOR]

Bursera fagaroides, popularly used in México, possesses bioactive lignans. These compounds are low in the bark, and its extraction endangers the life of the trees. The aim of the present investigation was to search for alternative sources of cytotoxic compounds in B. fagaroides prepared as leaves and in vitro callus cultures. The friable callus of B. fagaroides was established using a combination of plant growth regulators: 4 mgL−1 of 2,4-dichlorophenoxyacetic acid (2,4-D), 1 mgL−1 Naphthaleneacetic Acid (NAA) and 1 mgL−1 Zeatin. The maximum cell growth was at day 28 with a specific growth rate of μ = 0.059 days−1 and duplication time td = 11.8 days. HPLC quantification of the dichloromethane callus biomass extract showed that Scopoletin, with a concentration of 10.7 µg g−1 dry weight, was the main compound inducible as a phytoalexin by the addition of high concentrations of 2,4-D, as well as by the absence of nutrients in the culture medium. In this same extract, the compounds γ-sitosterol and stigmasterol were also identified by GC-MS analysis. Open column chromatography was used to separate and identify yatein, acetyl podophyllotoxin and 7′,8′-dehydropodophyllotoxin in the leaves of the wild plant. Cytotoxic activity on four cancer cell lines was tested, with PC-3 prostate carcinoma (IC50 of 12.6 ± 4.6 µgmL−1) being the most sensitive to the wild-type plant extract and HeLa cervical carcinoma (IC50 of 72 ± 5 µgmL−1) being the most sensitive to the callus culture extract.

Biomass accumulation in cuttings of four Bursera species during four seasons of the year, in five substrates under greenhouse conditions was evaluated. Cuttings were established under a completely randomized experimental design with factorial arrangement to apply destructive sampling at the end of each season of the year and to calculate structural biomass. The species factor and growing season showed effects on biomass accumulation. Bursera fagaroides accumulated higher biomass in roots, branches and leaves (2.85, 1.67 and 3.76 g/plant, respectively), along with B. glabrifolia showed higher leaf area (386.34 and 205.65 cm²/plant, respectively), good aboveground biomass/ground biomass ratio and high survival percentages (78 and 58%, respectively). [ABSTRACT FROM AUTHOR]

Se evalúa la acumulación de biomasa en estacas de cuatro especies de Bursera durante cuatro estaciones del año, en cinco sustratos bajo condiciones de invernadero. Se establecieron bajo un diseño experimental completamente aleatorizado con arreglo factorial para aplicarles muestreo destructivo al final de cada estación del año (2013) y calcular biomasa estructural. El factor especie y estación de crecimiento mostraron efectos en la acumulación de biomasa. Bursera fagaroides acumuló mayor biomasa en raíz, ramas y hojas (2.85, 1.67 y 3.76 g/planta respectivamente); junto con B. glabrifolia presentó mayor área foliar (386.34 y 205.65 cm2/planta respectivamente), buena relación biomasa aérea/biomasa subterránea y porcentajes de supervivencia altos (78 y 58% respectivamente).

Bursera fagaroides is a medicinal tree endemic to México, it belongs to the Burseraceae family and has proven antitumor activity. Modern research, performed principally with the bark extracts, have indicated that lignans are the main active constituents of B. fagaroides, with a high content of aryltetralin, aryldihydronaphtalene, dibenzylbutirolactone, and dibenzylbutane-type lignans as the constituents of the active extracts. In general, lignans from B. fagaroides exhibited potent anti-cancer activity, although antitumor, anti-bacterial, anti-protozoal, anti-inflammatory, and anti-viral properties have also been described. This review covers literature-reported lignans from B. fagaroides, chemical structures, nomenclature, chromatographic techniques of isolation, characterization strategies, and highlights the anti-cancer molecular mechanisms of lignans. Evaluation of the anticancer function of lignans has been extensively investigated since the cytotoxic in vitro results and in vivo assays in mice and zebrafish models to the tubulin molecular recognition by NMR. Also, we discuss the future direction for studying this important plant species and its lignan metabolites.

Having an aesthetic form is one of the desirable aspects of trees used to create or reforest urban green areas, which is often achieved by procedures that require a great effort. The understanding of factors affecting the architecture of plants in natural conditions may be useful to promote a desirable shape during the growth process. Under the hypothesis that trees in high luminosity conditions have a more aesthetical growth, in this study we explore the relationship between plant shape and photosynthetically active radiation (PAR) in Bursera fagaroides, a characteristic species of the tropical dry forest and xerophytic shrub-lands useful for urban green areas in semiarid environments. To evaluate trees shape we calculate a symmetry index ( I S ) by using two diameters of the crown, perpendicular to each other, and the total height. Measurements were made over three periods (before, during and after the growth period); and PAR was also measured for each tree. Linear regressions were used to analyze the relationship between the symmetry of trees and PAR received during the growth period. The post-growth symmetry of trees showed a positive relationship with the PAR received by trees during the growth period, suggesting that PAR effects can be harnessed to develop post-germination strategies for the production of trees with a more aesthetical growth in the studied species. Effect of PAR on the shape of plants may represent a practical option to promote aesthetical growth of trees and shrubs with importance for creation and restoration of urban green areas. [ABSTRACT FROM AUTHOR]

Antecedentes. Las condiciones ambientales en los bordes de los fragmentos de vegetación afectan las características del ciclo de vida de la biota nativa (efecto de borde). Evaluamos el efecto de borde en dos especies de Bursera, las cuales son representativas de la comunidad madura del bosque tropical caducifolio (BTC) en México. Hipótesis. Esperábamos una estructura poblacional que reflejara la afectación de la reproducción supervivencia y crecimiento en los bordes de los fragmentos de BTC. Especies en estudio. Bursera fagaroides, B. palmeri. Sitio de estudio y fechas. Querétaro (Qro.), Apaseo el Grande (Gto.), México. Trabajo de campo: mayo-septiembre 2012. Métodos. Dentro de cada uno de los nueve fragmentos de BTC, trazamos parcelas en dos condiciones ambientales contrastantes (de borde e interior), entre las que se comparó la densidad, estructura de la población y el éxito reproductivo de las dos especies de Bursera, así como estimadores de la radiación solar y la compactación del suelo. Resultados. La radiación solar y la compactación del suelo no fueron diferentes entre las condiciones ambientales. En ambas especies la densidad de individuos fue mayor en el borde, donde los individuos con tamaños medianos y grandes fueron predominantes. El potencial reproductivo de los individuos, así como la viabilidad y la germinación de sus semillas, fueron similares entre los ambientes de borde e interior. Conclusiones. La densidad y la estructura poblacional mostraron una variación congruente con mayores tasas de reclutamiento, crecimiento y supervivencia en el ambiente de borde, las cuales podrían haberse presentado en las condiciones iniciales de mayor incidencia de la radiación en los bordes. La similitud que se observa actualmente en la radiación solar entre el borde y el interior de los fragmentos, pudo ser el resultado de la recuperación rápida del dosel bajo condiciones de una incidencia de la luz más alta en los bordes.

Giardiasis, a diarrheal disease, is highly prevalent in developing countries. Several drugs are available for the treatment of this parasitosis; unfortunately, all of them have variable efficacies and adverse effects. Bursera fagaroides has been known for its anti-inflammatory and antidiarrheal properties in Mexican traditional medicine. We investigated the in vitro anti-giardial activities of four podophyllotoxin-type lignans from Bursera fagaroides var. fagaroides, namely, 5′-desmethoxy-β-peltatin-A-methylether (5-DES), acetylpodophyllotoxin (APOD), burseranin (BUR), and podophyllotoxin (POD). All lignans affected the Giardia adhesion and electron microscopy images revealed morphological alterations in the caudal region, ventral disk, membrane, and flagella, to different extents. Only 5-DES, APOD, and POD caused growth inhibition. Using the Caco-2 human cell line as a model of the intestinal epithelium, we demonstrated that APOD displayed direct antigiardial killing activity and low toxicity on Caco-2 cells. This finding makes it an attractive potential starting point for new antigiardial drugs. [ABSTRACT FROM AUTHOR]

By using a zebrafish embryo model to guide the chromatographic fractionation of antimitotic secondary metabolites, seven podophyllotoxin-type lignans were isolated from a hydroalcoholic extract obtained from the steam bark of Bursera fagaroides. The compounds were identified as podophyllotoxin (1), β-peltatin-A-methylether (2), 5′-desmethoxy-β-peltatin-A-methylether (3), desmethoxy-yatein (4), desoxypodophyllotoxin (5), burseranin (6), and acetyl podophyllotoxin (7). The biological effects on mitosis, cell migration, and microtubule cytoskeleton remodeling of lignans 1⁻7 were further evaluated in zebrafish embryos by whole-mount immunolocalization of the mitotic marker phospho-histone H3 and by a tubulin antibody. We found that lignans 1, 2, 4, and 7 induced mitotic arrest, delayed cell migration, and disrupted the microtubule cytoskeleton in zebrafish embryos. Furthermore, microtubule cytoskeleton destabilization was observed also in PC3 cells, except for 7. Therefore, these results demonstrate that the cytotoxic activity of 1, 2, and 4 is mediated by their microtubule-destabilizing activity. In general, the in vivo and in vitro models here used displayed equivalent mitotic effects, which allows us to conclude that the zebrafish model can be a fast and cheap in vivo model that can be used to identify antimitotic natural products through bioassay-guided fractionation.

Despite prevention and treatment options, breast cancer (BC) has become one of the most important issues in the present day. Therefore, the need for more specific and efficient compounds remains paramount. We evaluated four previously isolated aryltetralin lignans: 5'-demethoxy-β- peltatin-A-methylether (1), acetylpodophyllotoxin (2), 5'-demethoxydeoxypodophyllotoxin (3), and 7',8'-dehydroacetylpodophyllotoxin (4) for cytotoxicity, clonogenicity, and selectivity against three BC cell lines: MCF-7, MDA-MB-231, and BT-549, as well as the non-tumorigenic mammary epithelial cell line MCF-10A. Cytotoxicity was evaluated after 72 h of treatment, and clonogenicity was determined at 72 h post-treatment; experiments were performed using the sulforhodamine B staining assay. Selective-index (SI) was calculated by comparing pure compound IC50 values in MCF-10A cell line against the IC50 of the same compound in cancer cell lines. Structural similarities among lignans and controls (podophyllotoxin and etoposide) were analyzed using the Tanimoto coefficient (Tc). Lignans were cytotoxic against all tested cell lines (0.011-7.22 μM) and clonogenicity testing showed a dose-dependent cytocidality for all lignans (⩾0.08 μg/mL); compounds 2 and 3 were more potent (14.1 and 7.6 respectively) than etoposide in BT-549 cell line, while compound 2 displayed selectivity (SI = 28.17) in BT-549 cell line. Tc values of lignans suggested a greater similarity with podophyllotoxin structure. [ABSTRACT FROM AUTHOR]

Despite prevention and treatment options, breast cancer (BC) has become one of the most important issues in the present day. Therefore, the need for more specific and efficient compounds remains paramount. We evaluated four previously isolated aryltetralin lignans: 5′-demethoxy-β-peltatin-A-methylether (1), acetylpodophyllotoxin (2), 5′-demethoxydeoxypodophyllotoxin (3), and 7′,8′-dehydroacetylpodophyllotoxin (4) for cytotoxicity, clonogenicity, and selectivity against three BC cell lines: MCF-7, MDA-MB-231, and BT-549, as well as the non-tumorigenic mammary epithelial cell line MCF-10A. Cytotoxicity was evaluated after 72 h of treatment, and clonogenicity was determined at 72 h post-treatment; experiments were performed using the sulforhodamine B staining assay. Selective-index (SI) was calculated by comparing pure compound IC50 values in MCF-10A cell line against the IC50 of the same compound in cancer cell lines. Structural similarities among lignans and controls (podophyllotoxin and etoposide) were analyzed using the Tanimoto coefficient (Tc). Lignans were cytotoxic against all tested cell lines (0.011–7.22 µM) and clonogenicity testing showed a dose-dependent cytocidality for all lignans (≥0.08 µg/mL); compounds 2 and 3 were more potent (14.1 and 7.6 respectively) than etoposide in BT-549 cell line, while compound 2 displayed selectivity (SI = 28.17) in BT-549 cell line. Tc values of lignans suggested a greater similarity with podophyllotoxin structure.

Three new diarylbutane lignans, named 9-acetyl-9′-pentadecanoil-dihydroclusin (1), 2,3-demethoxy-secoisolintetralin monoacetate (4) and dihydroclusin monoacetate (5), have been isolated from the resin of Bursera fagaroides, together with two known ones, 2,3-demethoxy-secoisolintetralin diacetate (2) and dihydroclusin diacetate (3). The complete structure assignments were obtained by means of 1H and 13C NMR spectra. [ABSTRACT FROM AUTHOR]

Abstract: The ethanol extract from the dried exudate of Bursera fagaroides (Burseraceae) showed significant cytotoxic activity in the HT-29 (human colon adenocarcinoma) test system. The extract provided four podophyllotoxin related lignans, identified as (7′R,8R,8′R)-(−)-deoxypodophyllotoxin (3), (7′R,8R,8′R)-(−)-morelensin (4), (8R,8′R)-(−)-yatein (5), and (8R,8′R)-(−)-5′-desmethoxyyatein (6), whose spectroscopic and chiroptical properties were compared with those of (7R,7′R,8R,8′R)-(−)-podophyllotoxin (1) and its acetyl derivative (2). Their absolute configurations were assigned by comparison of the vibrational circular dichroism spectra of 1 and 3 with those obtained by density functional theory calculations. [Copyright &y& Elsevier]

It has been hypothesized that environmental variability can influence the sex ratio of a plant population, and it has been observed that in stressful environments, male plants are more abundant than females. However, it is unknown whether this is due to differential mortality rates between males and females. In this study, we analyzed sex ratio, mortality, and size distribution in a population of the neotropical tree/bush Bursera fagaroides in two different environments (east- and west-oriented slopes) over a 10-year period. We determined that the sex ratio favored males in the more stressful environment (east-facing slope) and that females were significantly larger in the less stressful environment (west-facing slope). Despite a significant difference in size between sexes by slope aspect, the difference in sex ratio cannot be explained by slope or by mortality during the 10 years of observation. [ABSTRACT FROM AUTHOR]

Abstract: The effect of an ethanolic extract from the stem bark of Bursera fagaroides on ornithine decarboxylase (ODC) activity in vitro and on the growth of Entamoeba histolytica was evaluated. For this purpose, increasing concentrations of the extract, up to 8.0mg/mL, were added to amoeba cultures or ODC reaction mixtures, which were incubated at 37°C. Metronidazole and G418 were added as controls. After 1.5 and 72h, the ODC activity in vitro and growth, respectively, were determined. Results revealed a strong inhibition of growth with IC50 values on the order of 0.05mg/mL. ODC activity, on the other hand, was inhibited by 12% and 50% at concentrations of 4.0 and 8.0mg/mL, respectively. [Copyright &y& Elsevier]

The aim of present work was to study Bursera fagaroides watery extract effect and Difluoromethylornithine (DFMO), applied individually or combined on healthy tissues and specifically on Polyamines (PAs) Putrecsine (Pu), Spermidine (Spd) and Spermine (Spm) metabolism in murine lymphoma L5178Y model. By means of ionic exchange chromatography, Pu levels in urine were determined as tumor evolution indicators, while renal ODC activity was quantified using radioimmunoassay. The results obtained suggest that the aqueous extract from Bursera fagaroides is a tumor stimulator, showing the opposite effect of the hidroalcoholic extract. [ABSTRACT FROM AUTHOR]

Bursera fagaroides is a medicinal tree endemic to México, it belongs to the Burseraceae family and has proven antitumor activity. Modern research, performed principally with the bark extracts, have indicated that lignans are the main active constituents of B. fagaroides, with a high content of aryltetralin, aryldihydronaphtalene, dibenzylbutirolactone, and dibenzylbutane-type lignans as the constituents of the active extracts. In general, lignans from B. fagaroides exhibited potent anti-cancer activity, although antitumor, anti-bacterial, anti-protozoal, anti-inflammatory, and anti-viral properties have also been described. This review covers literature-reported lignans from B. fagaroides, chemical structures, nomenclature, chromatographic techniques of isolation, characterization strategies, and highlights the anti-cancer molecular mechanisms of lignans. Evaluation of the anticancer function of lignans has been extensively investigated since the cytotoxic in vitro results and in vivo assays in mice and zebrafish models to the tubulin molecular recognition by NMR. Also, we discuss the future direction for studying this important plant species and its lignan metabolites. [ABSTRACT FROM AUTHOR]

By using a zebrafish embryo model to guide the chromatographic fractionation of antimitotic secondary metabolites, seven podophyllotoxin-type lignans were isolated from a hydroalcoholic extract obtained from the steam bark of Bursera fagaroides. The compounds were identified as podophyllotoxin (1), β-peltatin-A-methylether (2), 5′-desmethoxy-β-peltatin-A-methylether (3), desmethoxy-yatein (4), desoxypodophyllotoxin (5), burseranin (6), and acetyl podophyllotoxin (7). The biological effects on mitosis, cell migration, and microtubule cytoskeleton remodeling of lignans 1–7 were further evaluated in zebrafish embryos by whole-mount immunolocalization of the mitotic marker phospho-histone H3 and by a tubulin antibody. We found that lignans 1, 2, 4, and 7 induced mitotic arrest, delayed cell migration, and disrupted the microtubule cytoskeleton in zebrafish embryos. Furthermore, microtubule cytoskeleton destabilization was observed also in PC3 cells, except for 7. Therefore, these results demonstrate that the cytotoxic activity of 1, 2, and 4 is mediated by their microtubule-destabilizing activity. In general, the in vivo and in vitro models here used displayed equivalent mitotic effects, which allows us to conclude that the zebrafish model can be a fast and cheap in vivo model that can be used to identify antimitotic natural products through bioassay-guided fractionation. [ABSTRACT FROM AUTHOR]