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Citrus limettioides (Rutaceae), popularly known as “sweet lime” or “sweet lemon”, is rich in essential oil. Citrus sp. essential oils present a wide spectrum of biological activities, including insecticidal and larvicidal. In this sense, we aimed to investigate the larvicidal potential of Citrus limettioides peel essential oil on the main urban vector of dengue, chikungunya, yellow fever, and Zika viruses Aedes aegypti. The chemical characterization of the material revealed a monoterpene-rich essential oil (mainly limonene – 48.28% – and linalool – 32.17%). The C. limettioides peel essential oil presented a good larvicidal activity on A. aegypti (LC50 = 18.14 µg mL−1). Moreover, the compounds linalyl acetate and isopropyl tiglate, identified in the investigated essential oil, presented a predicted insecticide activity on A. aegypti. Finally, the safety of the C. limettioides peel essential oil was demonstrated on RAW 264.7 murine macrophages. These results support the idea of using the C. limettioides peel essential oil to the development of an economically viable larvicidal product.

Selenium nanoparticles (SeNPs), a potential cancer therapeutic agent, have attracted widespread attention owing to their high bioavailability and remarkable anticancer activity. Nevertheless, the poor water solubility and dispersibility of SeNPs seriously limit their applications. In the present study, we synthesized stable and individual spherical selenium nanoparticles (CL90-Tw-SeNP2) with an average diameter of approximately 79 nm using a polysaccharide extracted from Citrus limon (CL90) and Tween-80 as the decorator and stabilizers. The proportion of selenium in CL90-Tw-SeNP2 was 10.6%. CL90-Tw-SeNP2 possessed high stability and good dispersion in water for more than three months. The subsequent biological assay revealed that CL90-Tw-SeNP2 showed remarkable antitumor effects against HepG2 cells, with an IC50 value of 49.13 μg/mL, by inducing cell apoptosis. Furthermore, an in vivo zebrafish assay to explore possible applications indicated that CL90-Tw-SeNP2 could inhibit the proliferation and migration of tumors and the zebrafish angiogenesis. These results indicated that CL90-Tw-SeNP2 could be a potential agent for cancer treatment, especially against human liver hepatoma cancer.

The aromatic pink-flowered Phebalium complex is comprised by P. nottii Maiden & Betche, P. speciosum I. Telford and the very similar but mostly white-flowered P. woombye (F.M.Bailey) Domin. Phebalium nottii, as currently circumscribed, includes several geographically disjunct populations that have been segregated at the N.C.W. Beadle Herbarium as putatively distinct species, several of high conservation value. To study volatiles sustainably, large-scale hydrodistillation was aborted and only single leaves were removed from herbarium vouchers, extracted into solvent and analysed by GC–MS. Unlike other species of Phebalium, volatiles in pink-flowered Phebalium are mostly dominated by spathulenol and bicyclogermacrene. Multivariate analysis of the chemistry of volatiles clearly demonstrated good agreement between chemotypes and putative taxa in central Queensland populations. Southern taxa, and the true P. nottii sensu stricto from northern Queensland, express high levels of volatile coumarins. Thus, morphological relationships are mostly reflected in morphometric clusters. As with other members of Phebalium, most taxa can be distinguished on chemistry alone, using only GC–MS analysis of herbarium material. These results corroborate several new species and reveal relationships within the heterogeneous species aggregate of P. nottii.

Citrus limon (lemon) is an important fruit crop of Rutaceae family with high nutritive value. The microRNAs (miRNAs) are a class of small RNAs, approximately 22 nucleotides long. They are evolutionary conserved and function at post-transcriptional level to regulate the expressivity of genes in both plants and animals. They have crucial roles in different biological and metabolic processes like growth and development, pathogen defense, abiotic and biotic stress response in plants. Computational analysis of Citrus limon expressed sequence tags (ESTs) resulted in the identification of one conserved microRNA (clm-miR5658). The secondary structure of newly identified microRNA was generated based on minimal folding energy (MFE= −50.60 kcal/mol) and minimal folding energy index (MFEI= 0.81). Phylogenetic analysis of miR5658 family revealed a close association of clm-miR5658 with bra-miR5658. Further, a total of 14 potential target genes of the putative miRNA were identified and functionally annotated. The findings of this study will contribute to understand the role of miRNAs in lemon and expected to lay foundation for further research on lemon miRNAs.

The Manobo tribe in the Philippines is culturally rich in ethnomedicinal practices and known to use popular plants locally named as “Lunas” (meaning “cure”). One of these is “Lunas-bagon tapol” which was previously identified as Lunasia sp. (Rutaceae) based on vegetative morphology. The other species is “Lunas-buyo” which is similar in ethnomedicinal use and morphology. This broadly-based study verifies these two “Lunas”-named specimens and evaluates the phytochemicals present and cytotoxic properties. The sequences of nuclear ITS, and plastid rbcL, and matK were investigated for species identification. Molecular confirmation using BLASTn nucleotide database query revealed that the two confused “Lunas”-named specimens were members of Piperaceae and not Rutaceae. Phylogeny of Asian Piper using ITS sequences revealed “Lunas-bagon tapol” as Piper decumanum L. and “Lunas-buyo” as Piper aduncum L. with strong support (BS = 100 %). Both Piper species similarly showed the presence of alkaloids, flavonoids, steroids, tannins and fatty acids but the absence of cyanogenic glycosides. Also, P. decumanum has moderate amount of saponins while P. aduncum contains moderate amount of anthraquinones. A cytotoxic activity test using trypan blue exclusion method against normal lymphocytes from human blood showed low toxicity (91.9 % viable cells) for P. decumanum and mild toxicity (88.3 % viable cells) for P. aduncum when subjected to 1000 μg/ml of the stem ethanolic extracts. These results support the practical approach of molecular-based taxon identification and provide the biochemical and biological basis as to the constituents present and cytotoxic properties of these medicinal Piper species for future pharmacological research, conservation priorities and ecological management.

Limonoids are a kind of bioactive triterpenoids and mainly exist in the Meliaceae and Rutaceae plants. In this research, two new nimbolinin-type limonoids (1 and 2), one new trichilin-type limonoid (3), and one new havanensin-type limonoid (4), along with 11 known nimbolinin-type limonoids (5–15) were obtained from the fruits of Melia toosendan. Their structures were elucidated by a combination of high-resolution ESI-MS, 1D and 2D NMR spectra. Nimbolinin-type limonoid 11, 13, and 8 showed obvious effects on autophagy, as they significantly induced the accumulation of autophagosome and enhanced the lysosomal activity. A preliminary structure-activity relationship study suggested that substitution at C-12 and C-1 both have an evident influence on the activity. To the best of our knowledge, this is the first report on the autophagic activity of nimbolinin-type limonoids.

Three new compounds comprising two coumarins, paramicoumarins A (1) and B (2), and an acridone alkaloid, paramiacridone (3), together with seven known compounds, were isolated from the n-hexane extract of the roots of Paramignya trimera (Rutaceae). Their structures were elucidated using spectroscopic methods, mainly 1D and 2D NMR. α-Glucosidase inhibition and DPPH radical scavenging activity of the compounds and fifteen other compounds previously isolated from the roots of this plant were evaluated. Most of the compounds exhibited stronger α-glucosidase inhibitory activity than acarbose, the positive control (IC50 = 223.0 μM), and the new compounds paramiacridone (3) and paramicoumarin B (2) showed good inhibitory effect (IC50 = 62.5 and 65.5 μM, respectively). In the DPPH test for radical scavenging activity, the acridone alkaloid glycocitrin III (17) exhibited the highest antioxidant activity (IC50 = 84.2 μM) (compared with the positive control, ascorbic acid, IC50 = 152.7 μM).

Compounds derived from natural sources have been major contributors to the area of cancer chemotherapy for decades. As part of an ongoing effort to discover anticancer drug leads from tropical plants, a large-scale collection of Glycosmis ovoidea Pierre (Rutaceae), was made at Nui Chua National Park, Vietnam. Activity-guided fractionation of the chloroform-soluble fractions led to the isolation of nine coumarins, including the new compound, 1-(7-methoxy-2-oxo-2H-chromen-8-yl)-3-methyl-1-oxobut-2-en-2-yl (S)-2-methylbutanoate (1). An close analogue of 1, namely, kincuongin (2), was deemed as non-cytotoxic (IC

Two novel prenylated acetophenones with new carbon skeletons, acronyrones A and B (1 and 2), and a new analogue, acronyrone C (3), together with two known compounds (4 and 5) were isolated from the leaves of Acronychia pedunculata. Their structures with absolute configurations were identified by interpretation of spectroscopic data, single crystal X-ray diffraction, and electronic circular dichroism (ECD) calculations. Compounds 1 and 2 represent the first example of prenylated acetophenones possessed a C

Seven undescribed compounds, including four acridones, two coumarins, and a phenylpropanoid, together with 13 known acridone analogues were isolated from the ethanolic extract of the stems and leaves of Glycosmis ovoidea Pierre. Their structures were elucidated on the basis of comprehensive analysis of 1D and 2D NMR and HRESIMS spectroscopic data, and the absolute configurations were assigned by comparison of the experimental and calculated ECD data. Five compounds showed moderate inhibitory effects on nitric oxide production stimulated by lipopolysaccharide in BV-2 microglial cells with IC

Penicillium digitatum is the major source of postharvest decay in citrus fruits worldwide. This fungus shows a limited host range, being able to infect mainly mature fruit belonging to the Rutaceae family. This highly specific host interaction has attracted the interest of the scientific community. Researchers have investigated the chemical interactions and specialized virulence strategies that facilitate this fungus's fruit colonization, thereby leading to a successful citrus infection. There are several factors that mediate and affect the interaction between P. digitatum and its host citrus, including hydrogen peroxide modulation, secretion of organic acids and consequently pH control, and other strategies described here. The recently achieved sequencing of the complete P. digitatum genome opened up new possibilities for exploration of the virulence factors related to the host-pathogen interaction. Through such techniques as RNAseq, RT-PCR and targeted gene knockout mediated by Agrobacterium tumefaciens, important genes involved in the fungal infection process in citrus have been reported, helping to elucidate the molecular mechanisms, metabolites and genetic components that are involved in the pathogenicity of P. digitatum. Understanding the infection process and fungal strategies represents an important step in developing ways to protect citrus from P. digitatum infection, possibly leading to more productive citriculture.

Chromones are a group of natural substances with a diversity of biological activities. Herein we assessed the pharmacological potential of three chromones (1, 2 and 3) isolated from Dictyoloma vandellianum as anti-inflammatory agents using in vitro and in vivo approaches. During in vitro screening, the production of NO and cytokines by macrophages stimulated with LPS and IFN-γ was inhibited by all chromones at concentrations (5–20 μM) that did not induce cytotoxicity. Analysis of pharmacokinetic parameters (in vitro half-life and intrinsic clearance) using human liver microsomes revealed that 3 has a superior pharmacokinetic profile, compared to 1 and 2. Treatment with 3 (100 mg/kg, ip) did not affect the mice motor performance, while 1 and 2 induced motor deficit. Taking into account the pharmacokinetic profile and absence of motor impairment, 3 was selected for further pharmacological characterization. Corroborating the data from in vitro screening, treatment of cell cultures with 3 (5–20 μM) reduced TNF-α, IL-6 and IL-1β production by stimulated macrophages. In the complete Freund's adjuvant-induced paw inflammation model in mice, 3 (25 and 50 mg/kg, ip) inhibited mechanical hyperalgesia, edema and cytokine production/release (IL-1β, IL-6 and TNF-α). 3 (5–20 μM) also reduced the transcriptional activity of NF-κB in stimulated macrophages. Furthermore, treatment with RU486, a glucocorticoid receptor (GR) antagonist, partially prevented the inhibitory effect of 3 on macrophages, indicating that this chromone exerts its anti-inflammatory effects in part through the activation of GR. The results presented herein demonstrate the pharmacological potential of natural chromones, highlighting 3 as a possible candidate for the drug discovery process targeting new anti-inflammatory drugs.

The evolution of phytochemical diversity and biosynthetic pathways in plants can be evaluated from a phylogenetic and environmental perspective. Pilocarpus Vahl (Rutaceae), an economically important medicinal plant in the family Rutaceae, has a great diversity of imidazole alkaloids and coumarins. In this study, we used phylogenetic comparative methods to determine whether there is a phylogenetic signal for chemical traits across the genus Pilocarpus; this included ancestral reconstructions of continuous and discrete chemical traits. Bioclimatic variables found to be associated with the distribution of this genus were used to perform OLS regressions between chemical traits and bioclimatic variables. Next, these regression models were evaluated to test whether bioclimatic traits could significantly predict compound concentrations. Our study found that in terms of compound concentration, variation is most significantly associated with adaptive environmental convergence rather than phylogenetic relationships. The best predictive model of chemical traits was the OLS regression that modeled the relationship between coumarin and precipitation in the coldest quarter. However, we also found one chemical trait was dependent on phylogenetic history and bioclimatic factors. These findings emphasize that consideration of both environmental and phylogenetic factors is essential to tease out the intricate processes in the evolution of chemical diversity in plants. These methods can benefit fields such as conservation management, ecology, and evolutionary biology.

The ethanolic extract obtained from the stems of Glycosmis pentaphylla was found to suppress antigen-mediated degranulation of rat basophilic leukemia (RBL-2H3) cells. Four new geranylated 2-quinolone alkaloids, named glycopentanolones A–D (1–4), and 12 known metabolites (5–16) were isolated from the ethanolic extract from the stems of G. pentaphylla using bioassay-guided fractionation. Their structures were elucidated by a combination of 1D and 2D NMR, and HRESI-MS. The inhibitory effects of the isolated constituents on β-hexosaminidase release from RBL-2H3 cells were examined, and compounds 1, 5, 8 and 11 exhibited potent inhibitory activity with IC50 values between 0.05 and 4.28 μM.

A rotameric tryptamide alkaloid (1a-1b) was isolated from the methanolic extract of the roots of Vepris lecomteana together with the known compounds anhydroevoxine (2), lecomtequinoline C (3), evoxine (4), N-methylflindersine (5), evoxanthine (6), hesperidin, lupeol, beta-sitosterol and stigmasterol. The previously not reported 7-(3-anilino-2-hydroxyprenyloxy)-8-methoxydictamine (2a) was obtained by opening the epoxide of anhydroevoxine (2). The structures of above compounds were determined by comprehensive spectroscopic analyses of 1D and 2D NMR, EI-/ESI-MS, X-ray crystallography and comparison with the reported data. At room temperature, H-1 and C-13 NMR spectra show two rotamers (1a and 1b) with integrated intensities of 2/3, whereas at around 60 degrees C, only the 1b conformer was observed. Furthermore, the crystal structure of 1 was determined by the direct method of single crystal X-ray diffraction. The suggested biosynthesis for the formation of the new rotameric tryptamide alkaloid 1 is presented. Some of the isolated compounds (1, 2 and 2a) were tested in vitro against bacteria, resulting in weak for (1 and 2) to moderate activity for (2a) against Micrococcus Mulls and Escherichia coli with MIC values of 15.3 and 15.3 mu g/mL, respectively.

Diaporhte species are plant pathogens rarely involved in human diseases, especially eye diseases. We report our findings in two undescribed Diaporhte species. Both were identified by their morphological characteristics and by DNA sequence analyses. In Case 1, an 81-year-old male farmer who had pterygium surgery 7 years earlier developed keratitis and the causal fungus was identified as a new species of Diaporthe, D. oculi. This species can be distinguished from the closely related D. limonicola on Citrus limon (Rutaceae) by the ITS, tef1, and TUB (515/520 = 99.0% in ITS, 315/324 = 97.2% in tef1, and 601/614 = 97.9% in TUB). The isolate from Case 2, a 68-year-old man with a rose thorn injury, was also identified as a new Diaporthe species, D. pseudooculi. Phylogenetically, D. pseudooculi is different from the closely related D. podocarpi-macrophylli by the ITS, tef1, and TUB (525/531 = 98.9% in ITS, 314/333 = 94.3% in tef1, and 436/442 = 98.6% in TUB). We report on the identification, drug sensitivity, and treatment outcomes for these two new species of Diaporthe, D. oculi and D. pseudooculi.

Made available in DSpace on 2019-10-06T16:10:27Z (GMT). No. of bitstreams: 0 Previous issue date: 2019-02-01 Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Although the outer bark is important for protecting the inner tissues of stems of woody plants, especially from fire, the variation of outer bark in environments with different water availability, wind intensities, and solar radiation is little understood. Here, we examined the outer bark structure of Moquiniastrum polymorphum (Asteraceae) and Zanthoxylum rhoifolium (Rutaceae), co-occurring species in cerrado sensu stricto, cerradão, semi-deciduous seasonal forest and rainforest. Cerrado sensu stricto is a savanna with relatively intense solar radiation and winds. Cerradão, semi-deciduous seasonal forest and rainforest are progressively more closed and humid. We tested if trees in cerrado sensu stricto have relatively thicker outer and total bark than trees in the other three environments. For individuals of each species from each habitat, we described the morphological and anatomical features of the outer bark, including the origin of the first periderm. We compared the relative thickness of outer and total bark among habitats by means of ANOVA. In both species, we observed no qualitative differences in the morphological and anatomical features of the outer bark; therefore, these features are diagnostic for each species. For all habitats, the deep-seated origin of the first periderm and formation of a rhytidome in M. polymorphum produce a grooved bark with a loose appearance, whereas the subepidermal origin and formation of a single periderm in Z. rhoifolium produce a more uniform and smooth-appearing bark. Zanthoxylum rhoifolium trees in cerrado sensu stricto and cerradão have a thinner periderm, whereas M. polymorphum trees do not vary in rhytidome thickness among the habitats. In summary, trees from cerrado sensu stricto did not have relatively thicker outer bark and total bark than trees in cerradão, semi-deciduous seasonal forest and rainforest, suggesting that seasonal drought, intense solar radiation and winds do not seem to affect the total thickness of the outer bark. UNESP - São Paulo State University Faculdade de Ciências Agronômicas Departamento de Ciência Florestal Laboratório de Anatomia da Madeira, Avenida Universitária, 3780 UNESP - São Paulo State University Instituto de Biociências de Botucatu Departamento de Botânica, Distrito de Rubião Junior UNESP - São Paulo State University Faculdade de Ciências Agronômicas Departamento de Ciência Florestal Laboratório de Anatomia da Madeira, Avenida Universitária, 3780 UNESP - São Paulo State University Instituto de Biociências de Botucatu Departamento de Botânica, Distrito de Rubião Junior FAPESP: 2015/14954-1 CNPq: 304396/2015-0

The application of preparative thin layer chromatography-2,2-diphenyl-1-picrylhydrazyl (PTLC-DPPH) bioautography technique successfully isolated a lignan sesamin (1), two prenylated coumarins (2 and 3) and a marmesin glycosides (4) from Micromelum minutum methanol bark extract. Compounds 2 and 3 were identified as new compounds whereas 1 and 4 were first isolated from Micromelum genus. Structural identification of all compounds were done by detailed spectroscopic analyses and comparison with literature data. Antioxidant capacities of extract, active fraction and compounds were measured based on DPPH free radical savenging activity, oxygen radical absorbance capacity (ORAC) and β-carotene bleaching. The DPPH activity of methanol extract and its fraction present the IC50 values of 54.3 and 168.9 µg/mL meanwhile the β-carotene bleaching results were 55.19% and 5.75% respectively. The ORAC measurements of M. minutum extract, compounds 2 and 4 showed potent antioxidant activity with the values of 5123, 5539 and 4031 µmol TE/g respectively.

Five new prenylated acetophenones, melicoptelins A-E (1–5), along with one known congener (6) were isolated from the roots of Melicope ptelefolia. Among them, compounds 2a/2b, 3a/3b, and 4a/4b were obtained as inseparable interconverting mixtures of keto and enol tautomers. Their structures were elucidated on the basis of extensive spectroscopic methods, including 1D, 2D NMR and HRESIMS. Compouds 2a/2b, 4a/4b and 5 exhibit protein tyrosine phosphatase 1B (PTP1B) inhibitory activity with IC50 values of 34.4, 55.2 and 66.6 μM, respectively.

Green synthesized silver nanoparticles (AgNPs) are becoming an important candidate for bioremediation and biomedical applications. But in recent trends, more focus is given towards degradation of dyes and application against food pathogens. The synthesis of efficient AgNPs depends on the selection of potential biological material for synthesis. Therefore, in the present study, AgNPs were synthesized using Chloroxylon swietenia. The synthesis AgNPs was confirmed by the formation of dark brown precipitate. Further physicochemical characterization performed using XRD, FTIR, SEM and DLS showed the formation of crystalline structure, presence of functional group from the C. swietenia, dispersed spherical and rod-shaped nanoparticles (6.9 nm) and possess good stability due to the negative partial charges. The dye degrading efficacy of Chloroxylon swietenia mediated synthesized AgNPs (C-AgNPs) was95%, 90% and90% tested against Congo red (CR), Coomassie blue (CB) and crystal violet (CV) dye, respectively withing 24 h of treatment under optimum conditions. The antibacterial activity of C-AgNPs (10 mg/mL) was analysed against Staphylococcus nepalensis (3.03 ± 0.35 cm), Staphylococcus gallinarum (2.96 ± 0.15 cm), Bacillus subtilis (2.86 ± 0.23 cm), Enterococcous faecalis (2.8 ± 0.30 cm) and Pseudomonas stuteria (2.06 ± 0.25 cm) using Disc diffusion method, Minimum inhibitory concentration (MIC) and Minimum bactericidal activity (MBC). Therefore, the present study is the first and foremost report on C-AgNPs application as dye degrading and antibacterial agents against food dyes and pathogens. This will provide a major strategy to unveil the complications in food and packaging industries worldwide.

Toddalia asiatica L., a significant medicinal plant in the family Rutaceae, has been applied to treat rheumatoid diseases for decades. Its pharmacological activities are mainly attributed to the existence of generous coumarins and alkaloids; however, the pharmacokinetics of Toddalia asiatica L. remain unclear. A high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) method was established for the simultaneous determination of four coumarins, three alkaloids and one flavonoid (hesperidin, nitidine chloride, chelerythrine, toddalolactone, isopimpinellin, pimpinellin, bergapten and dictamnine) in rat feces as well as four coumarins and one alkaloid (toddalolactone, isopimpinellin, pimpinellin, bergapten and dictamnine) in rat plasma and urine. Chromatographic separation was accomplished on an Agilent ZORBAX SB-C18 column (2.1 × 150 mm, 5 μm) with acetonitrile (containing 0.1% formic acid) and 5 mmol/L aqueous ammonium formate for gradient elution. A correlation coefficient greater than 0.9925 reflected the excellent linearity of the analytical response. The lower limits of quantification were 30.0, 10.0, 10.0, 30.0, 5.0, 10.0, 2.5 and 2.5 ng/mL for hesperidin, nitidine chloride, chelerythrine, toddalolactone, isopimpinellin, pimpinellin, bergapten and dictamnine, respectively. The intra- and inter-day precision were less than 12.7%, and the accuracy was between -11.8% and 12.9%. In summary, this study is the first to study the pharmacokinetics and excretion of T. asiatica extract after oral administration, which may provide a scientific basis for its clinical applications.

Objective: Oxidative stress causes multidirectional damage including different types of cancers in our body by affecting the normal physiological functions of the cells and tissues. The objective is to study the cytotoxic and antioxidant potential of natural compounds isolated from fruits of Z. armatum DC. Methods: This study was designed to investigate the chemical nature as well as biological effects of natural compounds. The isolated compounds were tested for antioxidant effect in various ways e.g. DPPH free radical inhibition, ferric reducing effect, superoxide dismutase, and catalase evaluation. The cytotoxic effect of isolated compounds was evaluated using HepG2 cancer cells. Results: Chemical investigations on the fruits of Z. armatum DC, led to the isolation of two new compounds characterized as (cis)-2, 8-dimethyl-non-5-en-8-ol-2-olyl benzoate (1), (cis)-2, 10-dimethyl-undec-7-en-10-ol-2-olyl benzoate (2) along with five known compounds such as n-dodecanyl linoleniate (3), n-octacos-10, 20-dienoic acid (4), (cis, cis)-dotriacont-6, 12-dienoic acid (5), lignoceric acid (6), and (cis, cis)-dotriacont-6, 8-dienoic acid (7). Compound 1 shows potent activity against HepG2 cancer cells in comparison 2 and significantly affected the viability of cells till 48 hrs. The highest antioxidant potential among compounds and extracts with respect to DPPH free radical inhibition and the ferric reducing effect was shown by compound 1 followed by 2 and 7 with an EC50 value of 19.44, 20.44 and, 22.46 respectively. Conclusions: The present study indicates that compound (1) showed a significant effect against HepG2 cancer cells as well as antioxidant potential through DPPH and FRAP methods. Compounds 2 and 7 also proved to be useful up to some extent for antioxidant potential.

Anti-inflammatory activity guided isolation from Citrus garrawayi (Rutaceae) led to the discovery of five new garracoumarins A – E (1 - 5), and five known (6 – 10) isoprenylated furanocoumarins and the known sterol bourjotinolone A (11). Discussed herein is the anti-inflammatory structure activity relationship of the ten furanocoumarins and a detailed spectroscopic analysis leading to the structure elucidation of the new and known isoprenylated furanocoumarins.

Clausena lansium (Lour.) Skeels is an attractive shrub or small tree, a member of the Rutaceae family. The seeds, leaves and roots of this plant have been used as herbal medicines for a long time. In this study, seven amides were isolated from the seeds of Clausena lansium. The antifungal assay indicated that lansiumamide B (4) and lansiumamide C (2) displayed the highest antifungal activity against Sclerotinia sclerotiorum with EC50 values of 4.95 and 13.24 μg/mL, which were both lower than that of carbendazim (EC50 = 0.64 μg/mL). The structure-activity relationships of these amides were investigated using assays to measure their in vitro antifungal activities against Sclerotinia sclerotiorum. The effect of the most potent compound lansiumamide B on morphology and physiology of S. sclerotiorum were also evaluated. Lansiumamide B caused cell rupture and mycelial abnormalities of S. sclerotiorum, and its curative efficacy (75.17%) against S. sclerotiorum infection was better than that of carbendazim (56.57%). This study demonstrated that amides isolated from C. lansium possessed the potential to be exploited as botanical fungicides for commercial application or can be used as templates for designing new fungicides with novel action modes.

Methanolic crude extracts obtained from leaves, stem bark and root bark of 57 accessions of Clausena excavata, C. harmandiana, of both varieties of C. wallichii, as well as of three unidentified Clausena samples, were analysed for the presence of coumarins and carbazoles. All accessions were collected from different locations all over Thailand. HPLC coupled with UV-DAD was applied for phytochemical profiling. Structures of known pyrano-coumarins 1–4 and of coumarins 5–8 bearing an O-geranyl moiety, as well as of carbazoles 9–12 were confirmed by NMR and MS spectroscopy, respectively. Observed chemical diversification in the studied samples is discussed in relation to geographic distribution and with respect to organ-specific accumulation. Chemotaxonomic significance is briefly addressed.

Background Pamburus missionis (Wight) Swingle (Rutaceae) is traditionally used in the treatment of swellings, chronic rheumatism, paralysis and puerperal diseases. In a previous study the authors demonstrated apoptotic activity of Pamburus missionis essential oil (EO) on A431 and HaCaT cells. The major components of EO were β-caryophyllene (25.40%), 4(14),11- eudesmadiene (7.17%), aromadendrene oxide 2 (14.01%) (AO-(2) and phytol (6.88%). Purpose of study To investigate the role as well as the interactions among EO components inducing apoptosis in A431 and HaCaT cells. Methods Isobolographic analysis and combination index methods were used to detect the type of interactions among the essential oil (EO) components. Cell viability was used to detect cytotoxic activity. Mechanism of cell death was studied using Annexin V-FITC/PI binding assay, cell cycle analysis, measurement of MMP and ROS generation by flow cytometry. Expression of apoptosis associated proteins was investigated by western blot. Results Combination of P. missionis EO components: β-caryophyllene/ aromadendrene oxide 2 (β-C/AO-(2)), β-caryophyllene/phytol (β-C/P) and aromadendrene oxide 2 /phytol (AO-(2)/P) inhibited growth and colony formation ability of skin epidermoid A431 and precancerous HaCaT cells. Synergistic interaction was observed between β-C/AO-(2) and β-C/P combination while AO-(2)/P exhibited an additive effect. Combination of components induced chromatin condensation, phosphatidylserine externalisation, increase in sub-G1 DNA content, cell cycle arrest at G0/G1 phase and intracellular ROS accumulation. Inhibition of intracellular ROS by N-acetyl cysteine treatment blocked apoptosis induced by the combinations. The combinations induced apoptosis in A431 and HaCaT cells mediated by loss of mitochondrial membrane potential (ΔΨm), increase in Bax/Bcl-2 ratio, release of cytosolic cytochrome c and activation of caspases (cleaved form of caspase-3, caspase-8, caspase-9) and by PARP cleavage. Conclusion The present study demonstrates interactions among β-C, AO-(2) and P in the induction of apoptosis on A431 and HaCaT cells. These data suggest the combination of β-caryophyllene with aromadendrene oxide 2 and phytol could be potential therapeutics for the treatment of skin epidermoid cancer and precancerous cells.

In this research, we investigated the profile and bioactivities of quinazoline alkaloids, a class of natural products boasting multiple bioactivities, from the unripe fruit of Evodia rutaecarpa (Juss.) Benth. Three new quinazoline alkaloids, evodiamide A (1), evodiamide B (2), and evodiamide C (3), as well as eight known quinazolines, were isolated from the MeOH extract of E. rutaecarpa. The new compounds are rare quinazolinedione derivatives with linked heterocyclic nuclei. Among these quinazolines, rhetsinine (8) showed potential as a pesticide and exhibited excellent inhibition against Xanthomonas oryzae pv. oryzae, Xanthomonas oryzae pv. oryzicola, and Xanthomonas campestris pv. campestris, with respective EC50 values of 3.13, 14.32, and 32.72 nmol.

Skin maladies affect populations worldwide and can have a vast range of clinical manifestations, signs, and complications, including infection, pain, or even stigma for sufferers due to their visibility. Both modern health infrastructure and indigenous systems offer solutions for patients. This contribution provides an overview of the dermatologic uses for Thanatka, a plant that is used topically in Myanmar to treat a myriad of skin diseases. Indigenous to Myanmar, the trees used to produce Thanatka are also present in India, Sri Lanka, Java, and Pakistan.

From the stems of Paramignya trimera (Rutaceae), two new prenylated phenolic compounds, paratrimerins G (1) and H (2), together with 24 known compounds, as well as their α-glucosidase inhibitory activity was examined. Paratrimerins G (1) and H (2) showed moderate inhibitory effect, with the IC50 values of 89.2 and 58.8 μM, respectively. The plausible biosynthetic pathways of two new compounds was proposed.

Bamboo-Leaf Prickly Ash, Zanthoxylum armatum (Rutaceae) is a versatile and widely distributed plant species in nature. It is an edible plant species, commonly used in daily life for condiments and therapeutic remedies. Besides its bioactive and medicinal properties, different plant parts of the Z. armatum also have insecticidal potential. However, this potential has not been yet determined against many agricultural pests, including leaf worm, Spodoptera litura (Lepidoptera: Noctuidae). In this study, we demonstrated for the first time the contact and oral toxicity and sub-lethal effects (including antifeedent and ovicidal action) of various fractions of pericarp, leaf and seeds of Z. armatum against S. litura. Overall findings revealed that the n-hexane pericarp extract of Z. armatum has strong antifeedent, ovicidal and larvicidal properties against S. litura . Sub-lethal doses of pericarp extract can negatively alter the biology of S. litura . Since n-hexane extract of leaves also has better larvicidal properties, it could also be utilized for the S. litura management during period of unavailability of fruits (or pericarp). Accordingly, the Z. armatum pericarp and leaf extract has tremendous commercial utilization potential for the management of polyphagus pests like S. litura and other related species, which are quite difficult to manage even by chemical pesticides.

Green chemistry is a novel method for the synthesis of silver and zinc oxide nanoparticles. The present investigation focused on synthesis of biogenic silver and zinc oxide nanoparticles. They were assayed for their antibacterial activities against test bacterial species. The results revealed that the silver nanoparticles showed the maximum zone of inhibition 15.16, 15.5 and 13.33 mm at 400 μg/mL to S. aureus, S. typhi and P. aeruginosa respectively, when compared to the Erythromycin. While zinc oxide nanoparticles showed less activity in comparison to silver nanoparticles owing to the agglomeration of nanoparticles. It is evident from our investigation that silver nanoparticles could be used as an antimicrobial due to their intrinsic properties in biomedical application and food packing industries.

A new compound, nitomentosin (1), along with sixteen known compounds (2–17), were isolated from Zanthoxylum nitidum var. tomentosum (Rutaceae). The structure of compound 1 including absolute configurations was determined by detailed spectroscopic information (HRESIMS and NMR) and from the electronic circular dichroism (ECD) spectra. From the present investigation, compound 3 is a new natural compound although it has been reported previously as a synthetic substance, and compound 15 is found for the first time in a plant. All these compounds except 2, 5–10 and 12 were isolated from Z. nitidum for the first time. Furthermore, the chemotaxonomic significance of the isolated compounds is discussed.

The phytochemical study of the fruits of Zanthoxylum bungeanum Maxim led to the isolation of sixteen compounds, including a new compound zantharin (1) and fifteen other known compounds, which consist of ten coumarins (2–11), three alkaloids (12–14), and two phenols (15–16). Their structures were elucidated based on extensive spectroscopic methods (1D and 2D NMR, HRESIMS, UV, and IR experiments) and by comparison with literature data. In this work, all the compounds were isolated from Z. bungeanum for the first time, in which, compounds 5 and 13–16 were reported for the first time from the genus Zanthoxylum and the Rutaceae family, respectively. Moreover, the chemotaxonomic significance of isolated compounds is discussed.

Clausena lansium (Lour.) Skeels (Rutaceae) is a natural bioactive plant. Its roots, stems, leaves, and seeds are widely used in Chinese traditional and folk medicine. Although the characterization and functional analysis of bioactive components in Clausena lansium (Lour.) Skeels has been widely reported, the spatial distribution of these compounds within the main plant tissues remains undefined. Here, we adopted matrix-assisted laser desorption/ionization-mass spectrometry imaging (MALDI-MSI) to reveal the spatial distribution of active alkaloids, coumarins, sugars and organic acids in C. lansium. Using a combined wet and dry matrix covering method to enhance sensitivity, we detected alkaloids throughout the fruit including 3-methylcarbazole and murrastinine which were especially rich in the kernel tissues but were restricted to the stem xylem and medulla and in the leaf epidermal region. Interestingly, murrayanine and heptaphylline were mainly found in pulp tissues with very low content in the stems and leaves while girinimbine was only distributed within the outer kernel skin. Coumarins were mainly distributed in the fruit pericarp and leaf vein tissues but with no clear spatial specificity in stems. Lastly, hexoses were mainly evident in the fruit pulp, although sucrose was also found in the pericarp, pulp, and pulp fibers with citric acid being distributed throughout the fruit. The accurate spatial and chemical information obtained provides new insights into the specific accumulation of metabolites in individual tissues.

The antimicrobial effects of essential oils are commonly cited within aromatherapeutic texts for use in respiratory tract infections. These essential oils are inhaled or applied to the skin to treat infections and manage symptoms associated with these conditions. A limited number of these essential oils have been scientifically studied to support these claims, specifically, against respiratory pathogens. This study reports on the minimum inhibitory concentration (MIC) of 49 commercial essential oils recommended for respiratory tract infections, and identifies putative biomarkers responsible for the determined antimicrobial effect following a biochemometric workflow. Essential oils were investigated against nine pathogens. Three essential oils, Amyris balsamifera (amyris), Coriandrum sativum (coriander) and Santalum austrocaledonicum (sandalwood) were identified as having greater activity (MIC value = 0.03–0.13 mg/ml) compared to the other essential oils investigated. The essential oil composition of all 49 oils were determined using Gas Chromatography coupled to Mass Spectroscopy (GC-MS) analysis and the GC-MS data analysed together with the antimicrobial data using chemometric tools. Eugenol was identified as the main biomarker responsible for antimicrobial activity in the majority of the essential oils. The ability of a chemometric model to accurately predict the active and inactive biomarkers of the investigated essential oils against pathogens of the respiratory tract was 80.33%.

Background and aim There is currently a significant taxonomic confusion in the genus Zanthoxylum which has a wide application in Kenyan herbal medicine. The significance of proper identification/classification of medicinal plants is key in connecting the ethnobotanical uses with the existing chemical and biological knowledge. This study aims at solving the challenges encountered in the classification of Zanthoxylum species in Kenya using metabolomics as a tool for chemosystematics. Methods Five Zanthoxylum species (Z. chalybeum, Z. gilletii, Z. holtzianum, Z. paracanthum and Z. usambarense) were analyzed using metabolomics approach where LC-MS analysis was used to establish the chemical profiles of each species. Hierarchical cluster analysis was used to show the relationship among the Zanthoxylum spp studied. Results Based on phytochemical production, the five Zanthoxylum species segregated into two clusters; cluster one composed of Z. gilletii Z. usambarense and Z. paracanthum while Z. chalybeum and Z. holtzianum constituted cluster two. The chemical markers (discriminants) were identified as; laudanine, kalambroside A, kalambroside B, gamma-sanshool, ochotensine, cis-N-methylcanadine, 18-hydroxylinoleic acid, dihydrochelerythrine, N-feruloylglycine, p-coumaric acid ethyl ester, dihydroberberine and one unknown compound. Conclusions Chemometric analysis of relatedness of Zanthoxylum group of plants conformed to the current classical taxonomy of Zanthoxylum species in Kenya.

β-Cryptoxanthin (BCX) possesses potential therapeutic and health benefits. However, BCX absorption is low because of its poor aqueous solubility. In this study, a complex between BCX and casein (Cas) was prepared to improve the water dispersibility and bioavailability of BCX. BCX was recovered quantitatively from freeze-dried kumquat powder through solid–liquid extraction and saponification. The complexation significantly improved the apparent solubility of BCX under acidic and neutral conditions. A cell membrane permeation test using a Caco-2 cell monolayer was performed to evaluate the bioavailability of the BCX–Cas complex. This complex and a blank sample were digested in vitro and added to the apical side of the Caco-2 cell membrane. The quantity of BCX that permeated using the BCX–Cas complex after 24 h was 22.7 times greater than that of the blank. Thus, complexation of BCX with Cas improved dramatically the bioavailability of BCX from a kumquat extract.

Three novel lignans (1, 5 and 6) and two novel quinic acids (16 and 17) along with 15 known phenylpropanoids were obtained from the ethanol extract of Zanthoxylum nitidum var. tomentosum (Rutaceae). Their structures were confirmed by comprehensive spectroscopic data (NMR and HRESIMS), and the absolute configurations of all novel compounds were elucidated based on electronic circular dichroism (ECD) spectroscopic data. The production of nitric oxide (NO) in BV-2 microglial cells induced through lipopolysaccharide (LPS) was used to evaluate in vitro anti-neuroinflammatory activity of compounds 1–20. Compound 2, 3, 7 and 16 showed excellent inhibition of LPS-induced NO production. The structure-activity relationships of the isolates were investigated. In addition, the mechanism of action of 2 was elucidated by RT-PCR and Western blotting analysis, which indicated that it reduced neuroinflammatory mainly through NLRP3/caspase1 signaling pathways in LPS-induced BV2 microglial cells.

Choisya ternata Kunth variety Sundance (CTS) is a plant used in traditional medicine in North America, especially in Mexico. The present study evaluated the antinociceptive activity of the crude ethanolic extract of CTS leaves and tested its isolated compounds puberulin (Pu) and choisyine (Ch). An antinociceptive effect was observed after treatment with CTS extract and the isolated compounds Pu and Ch. Mice orally pre-treated with CTS extract (10, 30 or 100 mg/kg), Pu or Ch (0.3, 1 or 3 mg/kg) were less sensitive to chemical and thermal algesic agents in different animal models (formalin-, glutamate- and capsaicin-induced licking response tests and hot plate test). In addition, an antagonist of the opioid receptor was able to reverse the antinociceptive effect observed for the CTS extract and the isolated substance Ch, but it did not inhibit the effect of Pu. The cholinergic pathway was found to be involved in this antinociceptive effect for the CTS extract and Ch but has no participation in the Pu antinociceptive activity.

Mast cells play a central role in the pathogenesis of allergic reaction. Activation of mast cells by antigens is strictly dependent on the influx of extracellular calcium that involves a complex interaction between signalling molecules located within the cells. We have previously reported that tHGA, an active compound originally isolated from a local shrub known as Melicope ptelefolia , prevented IgE-mediated mast cell activation and passive systemic anaphylaxis by suppressing the release of interleukin-4 (IL-4) and tumour necrosis factor (TNF)-α from activated rat basophilic leukaemia (RBL)-2H3 cells. However, the mechanism of action (MOA) as well as the molecular target underlying the mast cell stabilising effect of tHGA has not been previously investigated. In this study, DNP-IgE-sensitised RBL-2H3 cells were pre-treated with tHGA before challenged with DNP-BSA. To dissect the MOA of tHGA in IgE-mediated mast cell activation, the effect of tHGA on the transcription of IL-4 and TNF-α mRNA was determined using Real Time-Polymerase Chain Reaction (qPCR) followed by Calcium Influx Assay to confirm the involvement of calcium in the activation of mast cells. The protein lysates were analysed by using Western Blot to determine the effect of tHGA on various important signalling molecules in the LAT-PLCγ-MAPK and PI3K-NFκB pathways. In order to identify the molecular target of tHGA in IgE-mediated mast cell activation, the LAT and LAT2 genes in RBL-2H3 cells were knocked-down by using RNA interference to establish a LAT/LAT2 competition model. The results showed that tHGA inhibited the transcription of IL-4 and TNF-α as a result of the suppression of calcium influx in activated RBL-2H3 cells. The results from Western Blot revealed that tHGA primarily inhibited the LAT-PLCγ-MAPK pathway with partial inhibition on the PI3K-p65 pathway without affecting Syk. The results from RNAi further demonstrated that tHGA failed to inhibit the release of mediators associated with mast cell degranulation under the LAT/LAT2 competition model in the absence of LAT. Collectively, this study concluded that the molecular target of tHGA could be LAT and may provide a basis for the development of a mast cell stabiliser which targets LAT.

Syncarpamide 1 , a norepinephrine alkaloid isolated from the leaves of Zanthoxylum syncarpum (Rutaceae) exhibited promising antiplasmodial activities against Plasmodium falciparum with reported IC 50 values of 2.04 μM (D6 clone), 3.06 μM (W2 clone) and observed by us 3.90 μM (3D7 clone) and 2.56 μM (K1 clone). In continuation of our work on naturally occurring antimalarial compounds, synthesis of syncarpamide 1 and its enantiomer, ( R )- 2 using Sharpless asymmetric dihydroxylation as a key step has been accomplished. In order to study structure-activity-relationship (SAR) in detail, a library of 55 compounds ( 3 – 57 ), which are analogues/homologues of syncarpamide 1 were synthesized by varying the substituents on the aromatic ring, by changing the stereocentre at the C-7 and/or by varying the acid groups in the ester and/or amide side chain based on the natural product lead molecule and further assayed in vitro against 3D7 and K1 strains of P. falciparum to evaluate their antiplasmodial activities. In order to study the effect of position of functional groups on antiplasmodial activity profile, a regioisomer ( S )- 58 of syncarpamide 1 was synthesized however, it turned out to be inactive against both the strains. Two compounds, ( S )- 41 and its enantiomer, ( R )- 42 having 3,4,5-trimethoxy cinnamoyl groups as side chains showed better antiplasmodial activity with IC 50 values of 3.16, 2.28 μM (3D7) and 1.78, 2.07 μM (K1), respectively than the natural product, syncarpamide 1 . Three compounds ( S )- 13 , ( S )- 17 , ( S )- 21 exhibited antiplasmodial activities with IC 50 values of 6.39, 6.82, 6.41 μM against 3D7 strain, 4.27, 7.26, 2.71 μM against K1 strain and with CC 50 values of 147.72, 153.0, >200 μM respectively. The in vitro antiplasmodial activity data of synthesized library suggests that the electron density and possibility of resonance in both the ester and amide side chains increases the antiplasmodial activity as compared to the parent natural product 1 . The natural product syncarpamide 1 and four analogues/homologues out of the synthesized library of 55, ( S )- 41 , ( R )- 42 , ( S )- 55 and ( S )- 57 were assayed in vivo assay against chloroquine-resistant P. yoelii (N-67) strain of Plasmodium . However, none of the five molecules, 1 , ( S )- 41 , ( R )- 42 , ( S )- 55 and ( S )- 57 exhibited any promising in vivo antimalarial activity against P. yoelii (N-67) strain. Compounds 4 , 6 , 7 and 11 showed high cytotoxicities with CC 50 values of 5.87, 5.08, 6.44 and 14.04 μM, respectively. Compound 6 was found to be the most cytotoxic as compared to the standard drug, podophyllotoxin whereas compounds 4 and 7 showed comparable cytotoxicities to podophyllotoxin.

Extraction and characterization of natural products from the bark of the trunk of Helietta apiculata Benth (Rutaceae) afforded nine alkaloids, eight furoquinoline and one quinolone, limonine, three cinnamic acid derivatives, three neolignans, tetracosanoic acid, six coumarins, of which apiculin A and apiculin B (neolignans), and tanizin (coumarin) are previously undescribed compounds. The structures of all compounds were determined by spectroscopic methods, and the crystal structures of two of the newly undescribed compounds, apiculin A and apiculin B, were determined by X-ray analysis. Extracts and pure compounds isolated from Helietta apiculata showed promising antimicrobial activities.

Two new flavonoid glycosides, excavaside A ( 1 ) and B ( 2 ), together with 14 known compounds, myricetin 3- O -β- d -rutinoside ( 3 ), myricetin 3,3′-di-α- l -rhamnopyranoside ( 4 ), myricetin 3′-α- l -rhamnopyranoside ( 5 ), myricitrin ( 6 ), myricetin ( 7 ), quercitrin ( 8 ), clauslactone B ( 9 ), clauslactone A ( 10 ), murrayacoumarin C ( 11 ), clauslactone E ( 12 ), triphasiol ( 13 ), clauslactone P ( 14 ), seseline ( 15 ), and 5-geranyloxy-7-hydroxycoumarin ( 16 ) have been isolated from the ethanol extract of the leaves and twigs of Clausena excavata . Among them, compounds 3 – 5 and 13 were isolated and identified from this plant for the first time. The structures of the new compounds were established by spectroscopic data interpretation, particularly HRESIMS, 1D and 2D NMR data including HSQC and HMBC. Also, those of the known compounds were identified by spectral comparison with those of the reported values.

A study of the chemical constituents obtained from twigs of Melicope lunu-ankenda (Gaertn.) T.G. Hartley (Rutaceae) led to the isolation and structure elucidation of two new coumarins, 7-(4-hydroxy-3-methylbutanoxy) coumarin and 7-(3-methyl-4-carboxybutanoxy) coumarin methyl ester, named melilunumarin A ( 1 ) and melilunumarin B ( 2 ), respectively. A new benzaldehyde derivative, 3,4-dihydro-3,4-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-carboxaldehyde, named melilunumane ( 6 ), was also isolated and characterized, as well as five previously reported compounds, 6-deoxyhaplopinol ( 3 ), marmesin ( 4 ), umbelliferone ( 5 ), kokusaginine ( 7 ) and evolitrin ( 8 ). Among the five isolated coumarins, melilunumarin A ( 1 ), 6-deoxyhaplopinol ( 3 ) and marmesin ( 4 ) exhibited significant inhibitory activity towards Epstein-Barr virus early antigen activation induced by 12-O-tetradecanoylphorbol 13-acetate in Raji cells.

Two acridones, paratrimerins C ( 1 ) and D ( 2 ), and two coumarins, paratrimerins E ( 3 ) and F ( 4 ), were isolated from the CHCl 3 and EtOAc extracts of Paramignya trimera (Rutaceae), together with twelve known compounds ( 5 – 16 ). Their structures were elucidated on the basis of spectroscopic data. All isolated compounds possessed significant α -glucosidase inhibitory activity in a concentration-dependent manner, and showed more potent inhibitory activity, with IC 50 values ranging from 14.6 to 112.2 μM, than the positive control acarbose (IC 50 , 214.5 μM). The biosynthesis of the isolated coumarins and acridones was proposed.

Two new acridone alkaloids, verdoocridone A (1) and B (4), together with fifteen known compounds were isolated from methanol extracts of the roots and leaves of Vepris verdoorniana. The structures of all compounds were determined by comprehensive spectroscopic analyses (1D and 2D NMR, EI-and ESIMS). The C-13 NMR values of 1,2,3,5-tetramethoxy-N-methylacridone (2) and 5-methoxyaborinine (3) are also reported. The crude extracts and compounds (1-6) were tested for their antimicrobial activity. The test delivered moderate activities for crude extracts and compounds 1, 5 and 6 against the bacterium Staphylococcus aureus and the fungi Mucor meihei and Candida albicans with MIC values between 115 and 180 mu g/mL for extracts and between 21.3 and 29.4 mu M for compounds, compared to gentamycin with 0.2 mu M and nystatin with 5.2 mu M against both fungi. The determination of the radical scanvenging activity using 1,1-dephenyl-2-picrylhydrazyl (DPPH) assay gave moderate antioxidant values for all tested compounds, with IC50 between 0.29 and 0.41 mu M, compared to the standard 3-t-butyl-4hydroxyanisole (BHA) displaying 0.03 mu M. (C) 2017 Phytochemical Society of Europe. Published by Elsevier Ltd. All rights reserved.

The first occurrences and dissemination of resistant microorganisms led to the inefficacy of many antibiotics, available in the market nowadays, therefore, the search for new substances with antimicrobial activity from natural sources has gained a great importance. The purpose of this work is to evaluate the antibacterial activity and modulation of drug resistance in Staphylococcus aureus by coumarins such as bergapten, xantotoxin, isopimpinellin and imperatorin obtained from two Rutaceae species (Metrodorea mollis and Pilocarpus spicatus). The antimicrobial activity was assessed based on the minimum inhibitory concentration (MIC), using the microdilution method. The MIC was >256 g/mL for all coumarins tested. Regarding the modulation of drug resistance assay, the isopimpinellin reducted the MIC of erytromicin by 4 times, whereas imperatorin exhibited the best result, reducing the MIC of tetracycline (2 times), erytomicin (4 times) and norfloxacin (4 times). By reducing the MIC of ethidium bromide, the imperatorin is consider in fact, as a putative efflux pump inhibitor of bacteria.

Background We previously described the gastroprotective effect of 2-phenylquinoline (2-PQ), the main alkaloid isolated from the bark of Galipea longiflora (Rutaceae). However, despite the significant and promising results, the pharmacological mechanisms of the gastroprotection induced by 2-PQ have not been investigated. Purpose To evaluate the mechanisms underlying the gastroprotective effects of 2-PQ. Study design We used an in vivo mouse ulcer model and in vitro methodologies involving H⁺/K⁺-ATPase and L929 murine fibroblasts. Methods The gastroprotective activity of 2-PQ (10–100 mg/kg, orally, p.o) was assessed against gastric ulcer induced by 60% ethanol/0.03 M hydrochloric acid (HCl) in mice or that induced by indomethacin (80 mg/kg, p.o) in rats. The cytotoxicity was assessed in L929 murine fibroblasts. Ulcerated tissues were analyzed histologically, histochemically, and biochemically. The antisecretory activity of 2-PQ was evaluated in vivo and in vitro. Results 2-PQ showed no cytotoxicity, reduced the lesion area induced by ethanol/HCl (log half-maximal effective dose, ED50 = 1.507), and the histological evaluation supported these results. Furthermore, 2-PQ reduced indomethacin-induced gastric ulceration. The gastroprotection was accompanied by normalization of superoxide dismutase (SOD) and glutathione-S-transferase (GST) activity, an intense increase in reduced glutathione (GSH) levels, and reduction in lipid peroxide (LPO) and tumor necrosis factor (TNF)-α levels in the gastric mucosa. The antisecretory properties of 2-PQ were confirmed by the decreased volume and total acidity of the gastric juice, and it reduced histamine- or pentagastrin-stimulated gastric acid secretion. However, 2-PQ did not change the in vitro H⁺/K⁺-ATPase activity or the content of gastric-adhered mucous in mice. In addition, pretreatment with N-ethylmaleimide, NG-nitro- l -arginine methyl esters, yohimbine, or indomethacin reversed the gastroprotective effect of 2-PQ, suggesting nitric oxide, nonprotein sulfhydryl compounds, α-2-receptors, and prostaglandin were involved. Conclusion 2-PQ provides gastroprotection by reducing oxidative damage and inhibiting acid secretion mediated by histaminergic and gastrinergic regulatory pathways.

Made available in DSpace on 2018-12-11T16:45:07Z (GMT). No. of bitstreams: 0 Previous issue date: 2017-01-01 Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) (−)-Cubebin (CUB), isolated from seeds of Piper cubeba, was used as starting material to obtain the derivatives (−)-hinokinin (HK) and (−)-O-benzyl cubebin (OBZ). Using paw edema as the experimental model and different chemical mediators (prostaglandin and dextran), it was observed that both derivatives were active in comparison with both negative (5% Tween� 80 in saline) and positive (indomethacin) controls. The highest reduction in the prostaglandin-induced edema was achieved by OBZ (66.0%), while HK caused a 59.2% reduction. Nonetheless, the dextran-induced paw edema was not significantly reduced by either of the derivatives (HK or OBZ), which inhibited edema formation by 18.3% and 3.5%, respectively, in contrast with the positive control, cyproheptadine, which reduced the edema by 56.0%. The docking analysis showed that OBZ presented the most stable ligand-receptor (COX-2 – cyclooxygenase-2) interaction in comparison with CUB and HK. N�cleo de Pesquisas em Ci�ncias Exatas e Tecnol�gicas Universidade de Franca, Av. Dr. Armando Salles Oliveira 201 School of Pharmaceutical Sciences of Ribeir�o Preto University of S�o Paulo, Av. do Caf� S/N Faculdade de Engenharia de Ilha Solteira Universidade Estadual Paulista J�lio de Mesquita Filho (UNESP), Av Brasil 56 Programa de P�s-Gradua��o em Ci�ncia Animal Universidade de Franca, Av. Dr. Armando Salles Oliveira 201 Departamento de Quı́mica Universidade Federal de Santa Catarina, Campus Universit�rio Trindade, CP 476 Faculdade de Engenharia de Ilha Solteira Universidade Estadual Paulista J�lio de Mesquita Filho (UNESP), Av Brasil 56 FAPESP: 2005/00494-7 FAPESP: 2011/07623-8 CNPq: 303349/2013-1 CNPq: 88881.068346/2014-01

Three new furanopyridine alkaloids, namely glypenfurans A–C (1–3), were isolated from the leaves of Glycosmis pentaphylla together with six known furoquinoline alkaloids. Their structures were determined by extensive spectral analysis (UV, IR, MS, 1D and 2D NMR).