Exploring the Fluconazole-Resistance Modifying Activity and Potential Mechanism of Action of Fixed Oil from Caryocar coriaceum Wittm. (Caryocaraceae) against Candida Species.

The fixed oil from the inner mesocarp of Caryocar coriaceum Wittm. is used in the Chapada do Araripe region of Brazil for the treatment of genitourinary candidiasis. This study aimed to evaluate the chemical composition, antifungal activity, reduction of fungal virulence, and the preliminary toxicity of the fixed oil from the inner mesocarp of C. coriaceum tested against three Candida yeasts. The oil was characterized by gas chromatography (GC-MS and GC-FID). Antifungal activity was assessed using the serial microdilution method. Additionally, the potential of the oil as an enhancer of fluconazole action was tested at sub-inhibitory concentrations (MIC/8). The mechanism of action of C. coriaceum fixed oil was determined by evaluating the inhibition of morphological transition in Candida spp. The chemical composition of the fixed oil of C. coriaceum comprised both unsaturated and saturated fatty acids. Oleic (61 %) and palmitic (33 %) acids were the major constituents. Regarding its anti-Candida activity, the oil inhibited the growth of C. albicans (IC50 : 371 µg/mL) and C. tropicalis (IC50 : 830 µg/mL). Furthermore, the oil reversed the antifungal resistance of C. albicans and C. tropicalis, restoring the susceptibility to fluconazole and reducing their IC50 from 12.33 µg/mL and 362 µg/mL to 0.22 µg/mL and 13.93 µg/mL, respectively. The fixed oil of C. coriaceum completely inhibited the morphological transition of C. albicans and C. tropicalis at a concentration of 512 µg/mL, but exhibited limited low antifungal potential against C. krusei. The observed antifungal activity may be attributed to the overproduction of reactive oxygen species. Additionally, the oil showed no toxic effect on the Drosophila melanogaster in vivo model. The fixed oil from the inner mesocarp of C. coriaceum emerge as a strong candidate for the development of new pharmaceutical formulations to treat infections caused by Candida spp.

Five undescribed aryltetralin lignans with cytotoxic activities from the fruits of Cleistanthus eberhardtii.

Five undescribed lignans, cleiseberharnins A-D (1-4), cleiseberharside A (5) were isolated from the fruits of Cleistanthus eberhartii (Phyllanthaceae), together with six known aryltetralin lignans, cleistantoxin (6), picroburseranin (7), neocleistantoxin (8), 7-hydroxypicropolygamain (9), cleisindoside D (10), and cleisindoside A (11). Their structures and relative configurations were established by analysis of HRESIMS and NMR data, and quantum chemical calculations of JH,H coupling constants. The absolute configurations of 1-5 were determined by analysis of their experimental CD spectra and comparison with calculated electronic circular dichroism (ECD) spectra. All compounds (1-11) were evaluated for their cytotoxicity against KB, MCF-7, HepG-2, and Lu-1 human cancer cell lines. Among the tested compounds, compounds 6 and 7 showed strong activity against KB, MCF7, HepG2 and Lu-1 cell lines with IC50 values in the range of 0.02-0.62 µM. Compound 1 showed activity against three cancer cell lines KB, HepG2, and Lu-1 with IC50 values of 6.98, 7.61 and 11.75 µM, respectively. Compound 2 exhibited a selective inhibition with moderate cytotoxicity against Lu-1 with IC50 value of 15.30 µM. Compounds 4, 5 and 9 showed moderate activity against the three cancer cell lines with IC50 values in the range of 8.73-19.70 µM.

Prebiotic Activity of Pequi (Caryocar brasiliense Camb.) Shell on Lactobacillus and Bifidobacterium Strains: A Medicinal Food Ingredient.

Pequi is a native and popular fruit in Cerrado biome. The internal yellow-orange mesocarp is the edible fraction of the fruit, but its shell (peel and external mesocarp), which comprises 80% of the fruit, is not used by the agro-industry during fruit processing. There is a growing interest in the reduction of food loss and waste because of environmental, economic, and social impacts. So this study evaluated the chemical composition, antioxidant capacity, and in vitro prebiotic activity of pequi shell flour. Pequi shell flour was obtained from the lyophilization and milling of pequi shell. The content of dietary fibers, oligosaccharides, sugars, organic acids, total phenolics and tannins, polyphenol profile, and antioxidant capacity was determined in pequi shell flour. In addition, its prebiotic activity was evaluated on growth and metabolism of probiotics Lactobacillus and Bifidobacterium strains. Pequi shell flour has a high content of dietary fibers (47.92 g/100 g), soluble fibers (18.65 g/100 g), raffinose (2.39 g/100 g), and phenolic compounds (14,062.40 mg gallic acid equivalents/100 g). For the first time, the polyphenols epigallocatechin gallate, epicatechin, and procyanidin B2 were identified in this by-product. Pequi shell flour promoted greater growth of Lacticaseibacillus casei L-26 (at 24-48 h) and Bifidobacterium animalis subsp. lactis BB-12, as well as higher prebiotic activity scores than fructooligosaccharides (standard prebiotic). Pequi shell flour is rich in prebiotic compounds and has a high antioxidant and prebiotic potential. The promising results encourage its use as an ingredient with antioxidant and potential prebiotic properties to elaborate new functional foods and nutraceuticals.

Sucking insects and their predators on tree canopies of a monocultural stand of Caryocar brasiliense / Insetos sugadores e seus predadores na copa de Caryocar brasiliense em sistema de monocultura

Abstract Caryocar brasiliense Camb. (Malpighiales: Caryocaraceae) trees are widely distributed throughout the Cerrado ecosystem. The fruits of C. brasiliense trees are used by humans for food and as the main income source in many communities. C. brasiliense conservation is seriously threatened due to habitat loss caused by the land-use change. Sucking insects constitute an important ecological driver that potentially impact C. brasiliense survival in degraded environments. In addition, insects sampling methodologies for application in studies related to the conservation of C. brasiliense are poorly developed. In this study, sucking insects (Hemiptera) and their predators were recorded in three vertical strata of Caryocar brasiliense canopies. The distribution of sucking species showed vertical stratification along the canopy structure of C. brasiliense. The basal part of the canopy had the highest numbers of sucking insects Aphis gossypii (Glover 1877) (Hemiptera: Aphididae) and Bemisia tabaci (Genn. 1889) (Hemiptera: Aleyrodidae), and their predators Chrysoperla sp. (Neuroptera: Chrysopidae), spiders (Araneae), and Zelus armillatus (Lep. & Servi., 1825) (Hemiptera: Reduviidae). Predators' distribution follows the resource availability and preferred C. brasiliense tree parts with a higher abundance of prey.

Resumo Caryocar brasiliense Camb. (Malpighiales: Caryocaraceae) é amplamente distribuído por todo o ecossistema de cerrado. Os frutos de C. brasiliense são utilizados na alimentação humana e constitui uma importante fonte de renda para muitas comunidades. A perda de habitat provocada pelas mudanças de uso da terra coloca em risco a conservação de C. brasiliense. Insetos sugadores constituem um importante fator ecológico que, potencialmente, afeta o fitness de C. brasiliense em ambientes degradados. Além disso, as metodologias de amostragem de insetos para aplicação em estudos relacionados à conservação de C. brasiliense são pouco desenvolvidas. Neste estudo, o número de insetos sugadores (Hemiptera) e seus predadores foram avaliados em três estratos verticais do dossel de C. brasiliense. A distribuição das espécies sugadoras apresentou estratificação vertical ao longo da estrutura do dossel. O estrato basal do dossel apresentou o maior número de insetos sugadores Aphis gossypii (Glover 1877) (Hemiptera: Aphididae) e Bemisia tabaci (Genn. 1889) (Hemiptera: Aleyrodidae), e seus predadores Chrysoperla sp. (Neuroptera: Chrysopidae), aranhas (Araneae) e Zelus armillatus (Lep. & Servi., 1825) (Hemiptera: Reduviidae). Os predadores distribuíram-se de acordo com a disponibilidade de recursos, ocorrendo em maior número nas partes do dossel com maior abundância de suas presas.

Do arthropods and diseases affect the production of fruits on Caryocar brasiliense Camb. (Malpighiales: Caryocaraceae)? / Artrópodes e doenças afetam a produção de frutos em Caryocar brasiliense Camb. (Malpighiales: Caryocaraceae)?

Frequencies, magnitudes, and distributions of occurrence can affect the events. The problem can be worse or the solution better if greater frequencies and magnitudes are presented with aggregated distribution in the production system. Indices, hence, are used to assist in decision-making on certain issues. The system formed by Caryocar brasiliense Camb. (Malpighiales: Caryocaraceae), a typical and economically important Brazilian Cerrado tree species, and its several arthropods are adequate to evaluate a new index. This study aimed to test an index to identify the loss and solution sources and their importance in the system's loss or income gain. The index is: Percentage of Importance Indice [...] separated the loss sources [e.g., Edessa rufomarginata De Geer, 1773 (Hemiptera: Pentatomidae) on fruits = 41.90%)] on the percentage of reduction of fruit production (e.g., 0.13%), calculated the attention level (e.g., 0.10/fruit), with a total lost production of 1.35% (≈ 307 total lost fruits). The % I.I. also separated the solution sources [e.g., Zelus armillatus (Lep. and Servi., 1825) (Hemiptera: Reduviidae) = 55.48%), the non-attention level (e.g., Z. armillatus: 0.394 for E. rufomarginata on fruit), with total income gain of 0.56% (≈ 128 total saved fruits) on the natural system (e.g., C. brasiliense trees). This index can calculate losses or the effectiveness of the solutions monetarily. Here I test the % I.I., an index that can detect the key loss and solution sources on the system, which can be applied in some knowledge areas.

Frequências, magnitudes e distribuição de ocorrência pode afetar os eventos. O problema pode ser pior ou a solução melhor se maiores frequências e magnitudes forem apresentadas com distribuição agregada no sistema de produção. Índices, então, são usados para assistir na decisão de certas questões. O sistema formado pelo Caryocar brasiliense Camb. (Malpighiales: Caryocaraceae), uma espécie arbórea típica e economicamente importante do Cerrado brasileiro, e seus diversos artrópodes são adequados para avaliar um novo índice. A motivação deste trabalho foi testar um índice capaz de identificar as fontes de perda e de soluções, e suas importâncias em termos de perdas ou ganhos no sistema. O índice é: percentagem de importância [...] separou as fontes de perda [ex., Edessa rufomarginata De Geer, 1773 (Hemiptera: Pentatomidae) em frutos = 41,90%)] na percentagem de redução na produção de frutos (ex., 0,13%), calculando o nível de atenção (ex., 0,10/fruto), com um total de perda de produção de 1,35% (≈ 307 frutos totais perdidos). O % I.I. também separou as fontes de solução [ex., Zelus armillatus (Lep. and Servi., 1825) (Hemiptera: Reduviidae) = 55,48%)], o nível de não atenção (ex., Z. armillatus: 0,394 para E. rufomarginata em fruto), com total de ganho de 0,56% (≈ 128 total de frutos salvos) no sistema natural (ex., árvores de C. brasiliense). Esse índice pode calcular essas perdas ou a eficácia das soluções monetariamente. Aqui eu testo o % I.I., um índice capaz de detectar fatores chaves de perda e de soluções no sistema, capaz de ser aplicado em algumas áreas do conhecimento.

Isolation and Anticancer Progression Evaluation of the Chemical Constituents from Bridelia balansae Tutcher.

The dichloromethane extract of the roots of Bridelia balansae Tutcher (Phyllanthaceae) was found to show potential anticancer activity against HCT116 colorectal cancer cell. Our bioassay-guided phytochemical investigation of the roots of B. balansae led to the identification of 14 compounds including seven lignans (1-7), three phenylbenzene derivatives (8-10), two flavanone (11-12), and two triterpenoids (13-14). Among them, 4'-demethyl-4-deoxypodophyllotoxin (1) is the first aryltetralin lignan compound identified from this plant species. In addition, the stereochemistry of 1 was validated by X-ray crystallography for the first time, and its distinguished cytotoxic effect on HCT116 cells with an IC50 value at 20 nM was induced via an apoptosis induction mechanism. Compound 1 could also significantly decrease the migration rate of HCT116 cells, indicating its potential application against cancer metastasis. The western blot analysis showed that 1 has the potential to inhibit cell proliferation and metastasis. Treatment of 1 resulted in the downregulation of matrix metalloproteinases 2 (MMP2) and p-Akt, while p21 was upregulated. Collectively, the present study on the phytochemical and biological profile of B. balansae has determined the plant as a useful source to produce promising anticancer lead compounds.

Glochodpurnoid B from Glochidion puberum Induces Endoplasmic Reticulum Stress-Mediated Apoptosis in Colorectal Cancer Cells.

Glochidpurnoids A and B (1 and 2), two new coumaroyl or feruloyl oleananes, along with 17 known triterpenoids (3-19) were obtained from the stems and twigs of Glochidion puberum. Their structures were elucidated by extensive spectroscopic data analyses, chemical methods, and single crystal X-ray diffraction. All compounds were screened for cytotoxicity against the colorectal cancer cell line HCT-116, and 2, 3, 5, 6, 11, and 17 showed remarkable inhibitory activities (IC50: 0.80-2.99 µM), being more active than the positive control 5-fluorouracil (5-FU). The mechanistic study of 2, the most potent compound, showed that it could induce endoplasmic reticulum (ER) stress-mediated apoptosis and improve the sensitivity of HCT-116 cells to 5-FU.

Polyploid Genome Assembly Provides Insights into Morphological Development and Ascorbic Acid Accumulation of Sauropus androgynus.

Sauropus androgynus (S. androgynus) (2n = 4x = 52) is one of the most popular functional leafy vegetables in South and Southeast Asia. With its rich nutritional and pharmaceutical values, it has traditionally had widespread use for dietary and herbal purposes. Here, the genome of S. androgynus was sequenced and assembled, revealing a genome size of 1.55 Gb with 26 pseudo-chromosomes. Phylogenetic analysis traced back the divergence of Sauropus from Phyllanthus to approximately 29.67 million years ago (Mya). Genome analysis revealed that S. androgynus polyploidized around 20.51 Mya and shared a γ event about 132.95 Mya. Gene function analysis suggested that the expansion of pathways related to phloem development, lignin biosynthesis, and photosynthesis tended to result in the morphological differences among species within the Phyllanthaceae family, characterized by varying ploidy levels. The high accumulation of ascorbic acid in S. androgynus was attributed to the high expression of genes associated with the L-galactose pathway and recycling pathway. Moreover, the expanded gene families of S. androgynus exhibited multiple biochemical pathways associated with its comprehensive pharmacological activity, geographic adaptation and distinctive pleasurable flavor. Altogether, our findings represent a crucial genomic asset for S. androgynus, casting light on the intricate ploidy within the Phyllanthaceae family.

LC-MS/MS-Based Metabolomic Profiling of Constituents from Glochidion velutinum and Its Activity against Cancer Cell Lines.

This study aimed to establish the phytochemical profile of Glochidion velutinum and its cytotoxic activity against prostate cancer (PC-3) and breast cancer (MCF-7) cell lines. The phytochemical composition of G. velutinum leaf extract and its fractions was established with the help of total phenolic and flavonoid contents and LC-MS/MS-based metabolomics analysis. The crude methanolic extract and its fractions were studied for pharmacological activity against PC-3 and MCF-7 cell lines using the MTT assay. The total phenolic content of the crude extract and its fractions ranged from 44 to 859 µg GAE/mg of sample whereas total flavonoid contents ranged from 20 to 315 µg QE/mg of sample. A total of forty-eight compounds were tentatively dereplicated in the extract and its fractions. These phytochemicals included benzoic acid derivatives, flavans, flavones, O-methylated flavonoids, flavonoid O- and C-glycosides, pyranocoumarins, hydrolysable tannins, carbohydrate conjugates, fatty acids, coumarin glycosides, monoterpenoids, diterpenoids, and terpene glycosides. The crude extract (IC50 = 89 µg/mL), the chloroform fraction (IC50 = 27 µg/mL), and the water fraction (IC50 = 36 µg/mL) were found to be active against the PC-3 cell line. However, the crude extract (IC50 = 431 µg/mL), the chloroform fraction (IC50 = 222 µg/mL), and the ethyl acetate fraction (IC50 = 226 µg/mL) have shown prominent activity against breast cancer cells. Moreover, G. velutinum extract and its fractions presented negligible toxicity to normal macrophages at the maximum tested dose (600 µg/mL). Among the compounds identified through LC-MS/MS-based metabolomics analysis, epigallocatechin gallate, ellagic acid, isovitexin, and rutin were reported to have anticancer activity against both prostate and breast cancer cell lines and might be responsible for the cytotoxic activities of G. velutinum extract and its bioactive fractions.

Pequi oil (Caryocar brasilense Cambess.) nanoemulsion alters cell proliferation and damages key organelles in triple-negative breast cancer cells in vitro.

Pequi oil is extracted from the fruit of a Brazilian native plant (Caryocar brasiliense Camb) that contains some molecules with anticancer potential. Due to its hydrophobic property, the administration of pequi oil associated with nanoemulsion systems represents a successful strategy to improve oil bioavailability. Breast cancer is the most frequent type of cancer among women and conventional therapies used are frequently associated with several side effects. Thus, the aim of this study was to investigate the effects of pequi oil-based nanoemulsion (PeNE) on triple-negative breast cancer cells (4T1), in vitro. PeNE presented a dose- and time-dependent cytotoxic effect with lower IC50 than free pequi oil after 48 h of exposure (p < 0.001). At 180 µg/mL, PeNE demonstrated numerous cell alterations, when compared to free pequi oil, such as morphological alterations, reduction in cell proliferation and total cell number, damage to plasmatic membrane, induction of lysosomal membrane permeability and depolarization of mitochondrial membrane, alteration of intracellular ROS production and calcium level, and increase in phosphatidylserine exposure. Taken together, the results suggest an interesting induction of cell death mechanisms involving a combined action of factors that impair nucleus, mitochondria, lysosome, and ER function. In addition, more pronounced effects were observed in cells treated by PeNE at 180 µg/mL when compared to free pequi oil, thereby reinforcing the advantages of using nanometric platforms. These promising results highlight the use of PeNE as a potential complementary therapeutic approach to be employed along with conventional treatments against breast cancer in the future.

Composição de fenólicos, flavonoides, antocianinas, determinação da atividade antioxidante e comparação de métodos extrativos da folha e da casca de Caryocar brasiliense / Composition of Phenolic, Flavonoids, Anthocyanins, Determination of Antioxidant Activity and Comparison of Extractive Methods of Leaf and Bark of Caryocar brasiliense

Introdução: Caryocar brasiliense é conhecida popularmente como Pequi ou Pequizeiro, sendo uma planta com propriedades medicinais para tratamento de doenças respiratórias, úlceras gástricas e dores musculares. Objetivo: comparar a extração de biocompostos por meio de dois métodos extrativos, agitação magnética e banho ultrassônico. Além disso, avaliar a atividade antioxidante, o teor de compostos fenólicos, flavonoides e antocianinas em extratos das folhas e da casca de Pequi (C. brasiliense), com vistas a agregar valor quanto às suas propriedades funcionais. Metodologia: o conteúdo de compostos fenólicos foi determinado pelo método de Folin-Ciocalteu, flavonoides e antocianinas pelo método de Lima e Melo. A atividade antioxidante foi medida pelo método 2,2-difenil-1-picrilhidrazil (DPPH). Resultados: o extrato das folhas de Pequi exibiu maior teor de fenólicos em relação à casca, independente do método de extração. O extrato das folhas obtido em banho ultrassônico apresentou forte atividade antioxidante com valor de 72,2%. Conclusão: os extratos de Pequi demonstraram um perfil fitoquímico promissor que deve ser investigado no futuro para aplicação farmacológica como adjuvante ou precursor na síntese de novos cosméticos ou medicamentos com propriedades antioxidante.

Introduction: Caryocar brasiliense is a medicinal plant used in the treatment of respiratory diseases, gastric ulcers and muscle pain. Objective: to compare the extraction of natural compounds using two extractive methods, magnetic stirring and ultrasonic bath. In addition, to evaluate the antioxidant activity, the content of phenolic compounds, flavonoids and anthocyanins in the leaves and bark of Pequi (C. brasiliense), with a view to adding value through its functional properties. Methodology: the phenolic content was determined by the Folin-Ciocalteu method, flavonoids and anthocyanins by the Lima and Melo method. Antioxidant activity was measured using the 2.2-diphenyl-1-picrilhhydrazyl (DPPH) method. Results: the extract of the Pequi leaves exhibited a higher phenolic content in relation to the bark for both extraction methods. The Pequi leaf in an ultrasonic bath showed strong antioxidant activity with a value of 72.2%. Conclusion: Pequi extracts demonstrated a promising phytochemical profile that should be investigated in the future for pharmacological application as an adjuvant or precursor in the synthesis of a new cosmetic or medicine with antioxidant function.

Enhancement of the functionality of women with knee osteoarthritis by a gel formulation with Caryocar coriaceum Wittm ("Pequi") nanoencapsulated pulp fixed oil.

Osteoarthritis (OA) is a degenerative joint disease that occurs when there is a change in the mechanical and biological properties of the articular cartilage and the subchondral bone; The condition is more prevalent in women than in men. Pequi oil (PO), which is extracted from the fruits of the pequi tree (Caryocar coriaceum Wittm), is widely used in traditional medicine in the Brazilian northeast for the management of inflammation and joint pain. The aim of this study was to develop a pharmaceutical formulation containing Carbopol® hydrogel nanoencapsulated with pequi pulp fixed oil (PeONC) and evaluate its therapeutic effect on functionality and pain in women with knee osteoarthritis. The study was divided into two stages: Stage 1 - preparation and physico-chemical characterization of the pharmaceutical formulation containing PeONC, cell viability assays and skin irritability testing. Step 2 - A double-blind randomized clinical trial evaluating knee symptoms, quality of life, pressure pain, function, muscle strength and range of motion. The nanoformulation was in a gel form, with a particle size of 209.5 ± 1.06 nm, a pH of 6.23 ± 0.45, a zeta potential of - 23.1 ± 0.4 mV, a polydispersity index of 0.137 ± 0.52, and containing nanocapsules with a spherical shape a polymeric wall and an oily nucleus. The gel showed no cytotoxicity and was not irritating to human skin. The treatment with PeONC increased the strength of the knee flexor and extensor muscles and the total motion range of the knee. In addition, the treatment reduced knee instability, pain, swelling, and locking; There was also an improvement in some items of the SF-36 quality of life questionnaire such as in respect of functional capacity and social aspects. In conclusion, PeONC was found to be a stable, safe formulation with no toxicity in respect of topical use in humans. Additionally, the treatment produced an increase in muscle strength and functionality that was associated with reduced knee symptoms and improved quality of life. Our findings showed that in a group of women treated with PeONC mitigated the symptoms of knee osteoarthritis.

Nonlinear molecular dynamics of quercetin in Gynocardia odorata and Diospyros malabarica fruits: Its mechanistic role in hepatoprotection.

Liver performs number of critical physiological functions in human system. Intoxication of liver leads to accumulation of free radicals that eventually cause damage, fibrosis, cirrhosis and cancer. Carbon tetrachloride (CCl4) belongs to hepatotoxin is converted to a highly reactive free radical by cytochrome P450 enzymes that causes liver damage. Plant extracts derived quercetin has substantial role in hepatoprotection. This study highlights the possible mechanism by which quercetin plays significant role in hepatoprotection. HPLC analysis revealed the abundance of quercetin in the fruit extracts of Gynocardia odorata and Diospyros malabarica, were isolated, purified and subjected to liver function analysis on Wistar rats. Post quercetin treatment improved liver function parameters in the hepatotoxic Wistar rats by augmenting bilirubin content, SGOT and SGPT activity. Gene expression profile of quercetin treated rats revealed down regulation of HGF, TIMP1 and MMP2 expressed during CCl4 induction. In silico molecular mechanism prediction suggested that quercetin has a high affinity for cell signaling pathway proteins BCL-2, JAK2 and Cytochrome P450 Cyp2E1, which all play a significant role in CCl4 induced hepatotoxicity. In silico molecular docking and molecular dynamics simulation have shown that quercetin has a plausible affinity for major signaling proteins in liver. MMGBSA studies have revealed high binding of quercetin (ΔG) -41.48±11.02, -43.53±6.55 and -39.89±5.78 kcal/mol, with BCL-2, JAK2 and Cyp2E1, respectively which led to better stability of the quercetin bound protein complexes. Therefore, quercetin can act as potent inhibitor against CCl4 induced hepatic injury by regulating BCL-2, JAK2 and Cyp2E1.

Seed size and presence of thorns in Caryocar brasiliense on seedling emergence

Commercial propagation of pequizeiro, which stands out among the main native fruits of the Cerrado region for its high economic potential, has been done by seeds, despite their erratic germination. The objective of this study was to evaluate the effect of seed size and presence of thorns on the endocarp on seedling emergence of pequizeiro in the field. Seeds were collected in a pequizeiro commercial area in Canarana-MT, Brazil. Due to availability, 2,353 thorny seeds (3 sizes) and 106 seeds without thorns (medium sized) were tested. Thorny seeds were classified as large ­ longer than 50 mm; medium ­ between 40 and 50 mm; small ­ less than 40 mm. Seedling emergence started after 50 days in all seed categories, extending up to 100 days in the large seeds and to about 1 year after sowing in the small and medium sized ones. Small seeds showed a lower rate and speed of emergence compared to the others. Large seeds showed higher emergence speed compared to the medium ones. The presence of thorns did not affect seedling emergence. These results indicate the advantages of pequizeiro seed classification for sowing purposes.

Saurobacciosides A - C: three new glycosides from Sauropus bacciformis with their cytotoxic activity.

Three new glycosides, named as saurobaccioside A (1), saurobaccioside B (2), saurobaccioside C (3), together with five known magastigmanes, canangaionoside (4), (6S,9S)-roseoside (5), cucumegastigmane I (6), icariside B5 (7), linarionoside A (8) were isolated from the whole plant of Sauropus bacciformis (L.) Airy Shaw. Their structures were established by extensive spectroscopic analysis (UV, IR, HR-ESI-MS and NMR) and by comparison of the spectral data with those reported in the literature. The absolute configurations of compounds 2 and 3 were elucidated by experimental CD spectra. Compounds 1-8 were screened their cytotoxic activities towards CAL27 and MDAMB231 cancer cell lines. Compound 1 exhibited significant cytotoxic activity towards CAL27 and MDAMB231 cell lines with IC50 values of 3.21 ± 0.23 and 4.75 ± 0.17 µM, respectively, which were smaller than those of positive control capecitabine (IC50: 8.20 ± 0.75 and 5.20 ± 0.89 µM). Other compounds (2-8) were inactive.

Distribution of galling insects and their parasitoids on Caryocar brasiliense tree crowns / Distribuição de insetos galhadores e seus parasitoides em copas de pequizeiros (Caryocar brasiliense)

Caryocar brasiliense Camb. (Malpighiales: Caryocaraceae) is widely distributed in the Brazilian savanna and its fruits are used by humans for food, production of cosmetics, lubricants, and in the pharmaceutical industry. This plant is damaged by galling insects. Number of these galling insects and their parasitoids was recorded, in the field (galls) and in the laboratory (adults emerged from the galls), from three C. brasiliense crown heights, during three years. Numbers of adults of Eurytoma sp. (Hymenoptera: Eurytomidae), galling insect (younger attack) and Sycophila sp. (Hymenoptera: Eurytomidae) (a parasitoid of Eurytoma sp.), were greater on the apical parts of C. brasiliense tree crowns. Numbers and groups of Eurytoma sp. globoid galls (older attack) were higher in the median and basal crown parts. The numbers of Eurytoma sp. galls were higher on apical part of C. brasiliense tree crown and also of their parasitoids.

Caryocar brasiliense Camb. (Malpighiales: Caryocaraceae) é, amplamente, distribuída no cerrado brasileiro e seus frutos são utilizados para alimentação humana, produção de cosméticos, lubrificantes e na indústria farmacêutica, no entanto, é danificada por insetos galhadores. O número de insetos galhadores e seus parasitoides foram avaliados, em campo (galhas) e em laboratório (emergência de adultos das galhas), em três alturas do dossel de C. brasiliense, durante três anos. Os números de adultos Eurytoma sp. (Hymenoptera: Eurytomidae), inseto galhador (galhas novas) e de Sycophila sp. (Hymenoptera: Eurytomidae), parasitoide de Eurytoma sp., foram maiores na parte apical do dossel da copa de árvores de C. brasiliense. A quantidade de galhas globoides de Eurytoma sp., isoladas ou em grupo (galhas velhas), foi maior na parte mediana e basal da copa. Os números de adultos do galhador Eurytoma sp. e de seus parasitoides, que os seguem, foram maiores na parte apical da copa de árvores de C. brasiliense.

Seasonal mite population distribution on Caryocar brasiliense trees in the Cerrado domain / Distribuição sazonal da população de ácaros em árvores de Caryocar brasiliense no domínio do Cerrado

Caryocar brasiliense Camb. (Malpighiales: Caryocaraceae) trees have a wide distribution in the Cerrado, and it is protected by federal laws. The need to monitor and understand pest damage to crops and forests is a major motivation for the study of population distribution. The mites (Acari) population distributions on C. brasiliense are unknown. We studied seasonal mite population distribution and their ecological indices on C. brasiliense trees in Cerrado areas during three years. Greatest number of Agistemus sp. (Stigmaeidae), Histiostoma sp. (Histiostomidae), Proctolaelaps sp. (Ascidae), and diversity and species richness on leaves of C. brasiliense occurred in the autumn; Tetranychus sp.1 (Tetranychidae) on leaves in the autumn and winter; Histiostoma sp., and Proctolaelaps sp. in fruits in the summer. No significant effect of season was observed in the abundance of Eutetranychus sp., Tetranychus sp.2 (Tetranychidae) and Acaridae. The populations of Acaridae, Eutetranychus sp., Proctolaelaps sp. and Tetranychus sp.1 negatively correlated with temperature. Proctolaelaps sp. and Tetranychus sp.1 correlated negatively with rainfall and Eutetranychus sp. and Proctolaelaps sp. positively with sunlight. The period with low rainfall and relative humidity increases the phytophagous mites and their predators, especially Agistemus sp.. The Tetranychus sp. And Histiostoma sp. species may become pests in C. brasiliense in the Cerrado domain.

As árvores Caryocar brasiliense Camb. (Malpighiales: Caryocaraceae) têm ampla distribuição no Cerrado e são protegidas por leis federais. A necessidade de monitorar e entender os danos causados pelas pragas às culturas e florestas é uma das motivações para o estudo da distribuição populacional que para ácaros (Acari) em C. brasiliense é desconhecida. A distribuição sazonal de populações de ácaros e seus índices ecológicos em C. brasiliense em áreas de Cerrado foram estudados durante três anos. Maior número de Agistemus sp. (Stigmaeidae), Histiostoma sp. (Histiostomidae), Proctolaelaps sp. (Ascidae) e diversidade e riqueza de espécies nas folhas de C. brasiliense ocorreram no outono; Tetranychus sp.1 (Tetranychidae) no outono e inverno; Histiostoma sp. e Proctolaelaps sp. em frutos ocorreram no verão. Não foram observados efeitos das estações na abundância de Eutetranychus sp., Tetranychus sp.2 (Tetranychidae) e Acaridae. As populações de Acaridae, Eutetranychus sp., Proctolaelaps sp. E Tetranychus sp.1 correlacionaram-se negativamente com a temperatura. Correlações negativas foram observadas entre chuva e Proctolaelaps sp. e Tetranychus sp.1 e positivas entre luz solar e Eutetranychus sp. e Proctolaelaps sp..Baixa pluviosidade e umidade relativa do ar aumentaram os ácaros fitófagos e seus predadores, principalmente Agistemus sp.. As espécies Tetranychus sp. e Histiostoma sp. podem se tornar pragas em C. brasiliense no domínio do Cerrado.

Phenylpropanoid-conjugated pentacyclic triterpenoids from the whole plants of Leptopus lolonum induced cell apoptosis via MAPK and Akt pathways in human hepatocellular carcinoma cells.

Our present and previous phytochemical investigations on Leptopus lolonum have resulted in the isolation of almost 30 phenylpropanoid-conjugated pentacyclic triterpenoids (PCPTs). During the continuous study on PCPTs, this kind of triterpenoid ester is considered as a natural product with low toxicity because of it's widely distribution in natural plants and edible fruits including kiwi fruit, durian, jujube, pawpaw, apple and pear. In the present work, we report the isolation, structural elucidation and cytotoxic evaluation of four new PCPTs (1-4) which obtained from L. lolonum. In addition, the possible biosynthesis pathway for 28-norlupane triterpenoid and potent effect of phenylpropanoid moiety for increasing the cytotxic effect of triterpenoids were also discussed. Among these compounds, compound 1 exhibited the highest cytotoxic effect on HepG2 cells with IC50 value of 11.87 µM. Further flow cytometry and western blot analysis demonstrated that 1 caused G1 cell cycle arrest by up-regulated the expression of phosphorylated p53 protein in HepG2 cells and induced cell apoptosis via MAPK and Akt pathways. These results emphasized the potential of PCPTs as lead compounds for developing anti-cancer drugs.

Prenylated 4-phenylcoumarins and 4-alkylcoumarins from Kielmeyera argentea and their cytotoxic activity.

Two new prenylated 4-phenylcoumarins, named kielcoumarin A (1) and kielcoumarin B (2) together with three known compounds, mammea B/BA (3), mammea B/BA cyclo F (4) and ferruol A (5), were obtained from stems and roots of Kielmeyera argentea (Calophyllaceae). Their structures were elucidated based on spectroscopic data. Cytotoxic activity of the 4-alkylcoumarins 3-5 was evaluated in vitro against human U251 glioblastoma cell line. Compound 3 showed significative activity with EC50 value of 6.6 µM while compounds 4 and 5 showed respective EC50 values of 52.0 and 37.0 µM.