Perspectives for Uses of Propolis in Therapy against Infectious Diseases.

Propolis has gained wide popularity over the last decades in several parts of the world. In parallel, the literature about propolis composition and biological properties increased markedly. A great number of papers have demonstrated that propolis from different parts of the world is composed mainly of phenolic substances, frequently flavonoids, derived from plant resins. Propolis has a relevant role in increasing the social immunity of bee hives. Experimental evidence indicates that propolis and its components have activity against bacteria, fungi, and viruses. Mechanisms of action on bacteria, fungi, and viruses are known for several propolis components. Experiments have shown that propolis may act synergistically with antibiotics, antifungals, and antivirus drugs, permitting the administration of lower doses of drugs and higher antimicrobial effects. The current trend of growing resistance of microbial pathogens to the available drugs has encouraged the introduction of propolis in therapy against infectious diseases. Because propolis composition is widely variable, standardized propolis extracts have been produced. Successful clinical trials have included propolis extracts as medicine in dentistry and as an adjuvant in the treatment of patients against COVID-19. Present world health conditions encourage initiatives toward the spread of the niche of propolis, not only as traditional and alternative medicine but also as a relevant protagonist in anti-infectious therapy. Production of propolis and other apiary products is environmentally friendly and may contribute to alleviating the current crisis of the decline of bee populations. Propolis production has had social-economic relevance in Brazil, providing benefits to underprivileged people.

Chemical composition and antimycoplasma activity of a brown propolis from southern Brazil.

Extracts of a sample of brown propolis produced in the district of Itapará (Southern Brazil) were obtained with solvents with increasing polarity. The extracts were analyzed by RPHPLC-DAD-ESI-MS/MS and evaluated toward activity against Mycoplasma bovis, M. gallisepticum, M. genitalium, M. hominis, M. hyorinis, M. penetrans and M. pneumonieae. Typical components of "alecrim-do-campo" propolis (e.g. prenylated phenylpropanoids and caffeoyl-quinic acids) were characterized in the analyzed extraccts, in addition to several flavonols. Less polar extracts showed higher anti-mycoplasma activity (MIC value commonly 3.9 µg/mL) than alcoholic and aqueous extracts (MIC value often 7.8-250 µg/mL). The results indicate that Itapará propolis is a promising source for the development of therapeutic drugs.

New propolis type from north-east Brazil: chemical composition, antioxidant activity and botanical origin.

BACKGROUND: Propolis is a bee product with wide diversity of biological activity. It has a complex composition, which is dependent on its botanical source. The present study aimed to determine the chemical profile, antioxidant activity and botanical origin of two samples of a propolis type from two locations of the state of Rio Grande do Norte (RN, north-east Brazil). RESULTS: The standard chemical characteristics of the RN propolis are similar or superior to the internationally marketed Brazilian green propolis. RN propolis from two locations have high antioxidant activity, corresponding to 10% (municipality of Afonso Bezerra) and 13% (municipality of Alto do Rodrigues) of quercetin activity by the 2,2-diphenyl-1-picrylhydrazyl method and to 15% (both locations) by the ß-carotene discoloration method. High-performance liquid chromatography with diode array detection (HPLC-DAD)-electrospray ionization-tandem mass spectrometry analyses revealed that most constituents of the RN propolis are flavonoids, mainly flavonols and chalcones. HPLC-DAD analysis of ethanol extracts revealed a great similarity between the chemical profile of RN propolis and shoot apices of 'jurema-preta' (Mimosa tenuiflora, Leguminosae, Mimosoideae). CONCLUSION: 'Jurema-preta' shoot apices are likely resin sources of RN propolis. The chemical characteristics and antioxidant property of RN propolis provide promising prospects for the introduction of this type of propolis into the apicultural market. © 2017 Society of Chemical Industry.

Glands on the foliar surfaces of tribe Cercideae (Caesapiniodeae, Leguminosae): distribution and taxonomic significance.

Large elongated glands occur on Cercideae leaf surfaces. Leaves of Bauhinia (55 taxa, 53 species), Cercis (1 species), Phanera (1 species), Piliostigma (2 species), Schnella (19 species) and Tylosema (1 species) were observed to determine location and relative number of glands. They were only observed on the abaxial leaf surface of 42 Bauhinia taxa. The glands were analyzed by light stereomicroscope and scanning electron microscopy. They are large (up to 270 µm long and 115 µm wide) and multicellular, containing lipophilic substances, probably volatile oils. Presence or absence and density of the glands in species of Bauhinia may be useful to determine species delimitation or distinction among infraspecific taxa. Higher density of glands is more common in species from "cerrado" (a savanna ecosystem) and "caatinga" (a semiarid ecosystem from northeast Brazil) areas. Bauhinia species devoid of foliar glands are frequently from humid forests.

Composition of the volatile fraction of a sample of Brazilian green propolic and its phytotoxic activity.

BACKGROUND: Propolis is a resinous material produced by honeybees, containing mainly beeswax and plant material. Despite the wide spectrum of biological activity of propolis, to our knowledge no studies have been carried out about phytotoxic properties of Brazilian propolis and its constituents. The aims of this study were to analyze the chemical composition and to evaluate the phytotoxic activity of the volatile fraction of a sample of Brazilian green propolis. RESULTS: Main constituents are the phenylpropanoid 3-prenylcinnamic acid allyl ester (26.3%) and the sesquiterpene spathulenol (23.4%). Several other sesquiterpenes and phenylpropanoids, in addition to linalool and α-terpineol (monoterpenes), were also detected. The activity of solutions of the volatile fraction at 1.0, 0.5 and 0.1% was tested on lettuce seeds and seedlings. The solution at 1% inhibited completely the seed germination and solutions at 0.1 and 0.5% reduced the germination rate index. The solution at 0.5% reduced the growth of the hypocotyl-radicle axis and the development of the cotyledon leaf. CONCLUSIONS: The chemical composition of the volatile fraction of this Brazilian green propolis is different from those previously described, and these results may contribute to a better understanding about the chemical variations in propolis. The volatile fraction of Brazilian green propolis influences both germination of seed lettuce and the growth of its seedlings, showing an phytotoxic potential.

Aqueous extract of brazilian green propolis: primary components, evaluation of inflammation and wound healing by using subcutaneous implanted sponges.

Propolis is a chemically complex resinous bee product which has gained worldwide popularity as a means to improve health condition and prevent diseases. The main constituents of an aqueous extract of a sample of green propolis from Southeast Brazil were shown by high performance liquid chromatography/mass spectroscopy/mass spectroscopy to be mono- and di-O-caffeoylquinic acids; phenylpropanoids known as important constituents of alcohol extracts of green propolis, such as artepillin C and drupanin were also detected in low amounts in the aqueous extract. The anti-inflammatory activity of this extract was evaluated by determination of wound healing parameters. Female Swiss mice were implanted subcutaneously with polyesther-polyurethane sponge discs to induce wound healing responses, and administered orally with green propolis (500 mg kg(-1)). At 4, 7 and 14 days post-implantation, the fibrovascular stroma and deposition of extracellular matrix were evaluated by histopathologic and morphometric analyses. In the propolis-treated group at Days 4 and 7 the inflammatory process in the sponge was reduced in comparison with control. A progressive increase in cell influx and collagen deposition was observed in control and propolis-treated groups during the whole period. However, these effects were attenuated in the propolis-treated group at Days 4 and 7, indicating that key factors of the wound healing process are modulated by propolis constituents.

Nutritional reserves of Vochysiaceae seeds: chemical diversity and potential economic uses.

Contents of proteins, carbohydrates and oil of seeds of 57 individuals of Vochysiaceae, involving one species of Callisthene, six of Qualea, one of Salvertia and eight of Vochysia were determined. The main nutritional reserves of Vochysiaceae seeds are proteins (20% in average) and oils (21. 6%). Mean of carbohydrate contents was 5. 8%. Callisthene showed the lowest protein content (16. 9%), while Q. cordata was the species with the highest content (30% in average). The contents of ethanol soluble carbohydrates were much higher than those of water soluble carbohydrates. Oil contents lay above 20% for most species (30. 4% in V. pygmaea and V. pyramidalis seeds). The predominant fatty acids are lauric (Q. grandiflora), oleic (Qualea and Salvertia) or acids with longer carbon chains (Salvertia and a group of Vochysia species). The distribution of Vochysiaceae fatty acids suggests for seeds of some species an exploitation as food sources (predominance of oleic acid), for other species an alternative to cocoa butter (high contents or predominance of stearic acid) or the production of lubricants, surfactants, detergents, cosmetics and plastic (predominance of acids with C(20) or C(22) chains) or biodiesel (predominance of monounsaturated acids). The possibility of exploitation of Vochysiaceae products in a cultivation regimen and in extractive reserves is discussed.

Brazilian red propolis: unreported substances, antioxidant and antimicrobial activities.

BACKGROUND: Chloroform, ethyl acetate and methanol extracts of a sample of red propolis from the state of Alagoas (northeast Brazil) were analyzed by gas chromatography-mass spectrometry and high-performance liquid chromatography-diode array detection-electrospray ionization-mass spectrometry. Antimicrobial and antioxidant activities were also obtained. RESULTS: The propolis sample contained low content of narigenin-8-C-hexoside, this being the first report of a C-glycoside in propolis. The main constituent found was characterized as 3,4,2',3'-tetrahydroxychalcone. Other important constituents were the chalcone isoliquiritigenin, the isoflavans (3S)-vestitol, (3S)-7-O-methylvestitol, the pterocarpan medicarpin, the phenylpropenes trans-anethol, methyl eugenol, elimicin, methoxyeugenol and cis-asarone, and the triterpenic alcohols lupeol and α- and ß- amyrins. The methanol extract exhibited high antioxidant activities by 2,2-diphenyl-1-picrylhydrazyl and ß-carotene/linoleic acid assay methods, and antimicrobial activity toward Gram-positive and Gram-negative bacteria. CONCLUSION: Structures are suggested for new substances never before seen in any kind of propolis. This is the first report of 3,4,2',3'-tetrahydroxychalcone and a flavone C-glycoside in a propolis sample.

How diverse is the chemistry and plant origin of Brazilian propolis?

Propolis is a honey bee product containing chiefly beeswax and resins originated from plant buds or exudates. Propolis resin exerts a diversity of biological activities, such as antitumoral, anti-inflammatory, antimicrobial, and defense of the hive against pathogens. Chemical standardization and identification of botanical sources is crucial for characterization of propolis. Types of Brazilian propolis are characteristic of geographical regions and respective biomes, such as savannas (Cerrado), mangroves, dry forest (Caatinga), rain forests (Amazon, Atlantic, and Interior forests), altitudinal fields ("Campos Rupestres"), Pantanal, and Araucaria forests. Despite the wide diversity of Brazilian biomes and flora, relatively few types of Brazilian propolis and corresponding resin plant sources have been reported. Factors accounting for the restricted number of known types of Brazilian propolis and plant sources are tentatively pointed out. Among them, the paper discusses constraints that honey bees must overcome to collect plant exudates, including the characteristics of the lapping-chewing mouthpart of honey bee, which limit their possibilities to cut and chew plant tissues, as well as chemical requirements that plant resins must fulfil, involving antimicrobial activity of its constituents and innocuity to the insects. Although much still needs to be done toward a more comprehensive picture of Brazilian propolis types and corresponding plant origins, the prospects indicate that the actual diversity of plant sources of honey bee propolis will remain relatively low.

Contents of tannins of cultivars of sorghum cultivated in Brazil, as determined by four quantification methods.

High tannin content in sorghum grains is an undesirable characteristic for poultry and pig feeding and represents a challenge for breeding programs. On the other hand, moderate content of tannins in sorghum may be beneficial in human diets because they exert anti-cancer, anti-inflammatory and reduced carbohydrate uptake effects, among others. The aim of this study was to compare tannin contents of twenty sorghum cultivars available in Brazil, as well as to compare results obtained with four methods of tannin quantification: butanol/HCl, vanillin/HCl, BSA/FeCl3 and PVPP/Folin-Ciocalteu. The results obtained with butanol/HCl and vanillin/HCl were higher than with BSA/FeCl3 and PVPP/Folin-Ciocalteu. A known amount of purified quebracho tannin was used to test the validation of methods of tannin quantification and vanillin/HCl stood out for its high accuracy degree. The sampling used reveals wide genetic diversity regarding tannin contents. The expectation of predicting tannin contents on basis of grain color seems unfeasible.

Seasonal variation, chemical composition and antioxidant activity of Brazilian propolis samples.

Total phenolic contents, antioxidant activity and chemical composition of propolis samples from three localities of Minas Gerais state (southeast Brazil) were determined. Total phenolic contents were determined by the Folin-Ciocalteau method, antioxidant activity was evaluated by DPPH, using BHT as reference, and chemical composition was analyzed by GC/MS. Propolis from Itapecerica and Paula Cândido municipalities were found to have high phenolic contents and pronounced antioxidant activity. From these extracts, 40 substances were identified, among them were simple phenylpropanoids, prenylated phenylpropanoids, sesqui- and diterpenoids. Quantitatively, the main constituent of both samples was allyl-3-prenylcinnamic acid. A sample from Virginópolis municipality had no detectable phenolic substances and contained mainly triterpenoids, the main constituents being α- and ß-amyrins. Methanolic extracts from Itapecerica and Paula Cândido exhibited pronounced scavenging activity towards DPPH, indistinguishable from BHT activity. However, extracts from Virginópolis sample exhibited no antioxidant activity. Total phenolic substances, GC/MS analyses and antioxidant activity of samples from Itapecerica collected monthly over a period of 1 year revealed considerable variation. No correlation was observed between antioxidant activity and either total phenolic contents or contents of artepillin C and other phenolic substances, as assayed by CG/MS analysis.

Evaluation of DNA markers for molecular identification of three Piper species from Brazilian Atlantic Rainforest.

Piper is one of two large genera in the Piperaceae, and with ca. 2600 species, is one of the largest plant genera in the world. Species delimitation and evaluation of genetic diversity among populations are important requisites for conservation and adequate exploitation of economically important species. DNA barcoding has been used as a powerful tool and a practical method for species characterization and delimitation. The present work aims to evaluate molecular markers for barcoding three Piper species native to Brazil: P. gaudichaudianum ("jaborandi" or "pariparoba"), P. malacophyllum ("pariparoba-murta") and P. regnellii ("caapeba" or "pariparoba"). A reference DNA barcode library was developed using sequences of three candidate regions: ITS2, trnH-psbA and rbcL. Transferability of the microsatellite (SSR) primers Psol 3, Psol 6 and Psol 10, designed originally for Piper solmsianum, to the three Piper species was also evaluated. The discriminatory power of the markers was based on the determination of inter- and intraspecific distances, phylogenetic reconstruction, and clustering analysis, as well as BLASTn comparison. Sequences of ITS2 enabled efficient species identification by means of the BLASTn procedure. Based on these sequences, intraspecific divergence was lower than interspecific variation. Maximum Parsimony analyses based on ITS2 sequences provided three resolved clades, each corresponding to one of the three analysed species. Sequences of trnH-psbA and rbcL had lower discriminatory value. Analyses combining sequences of these regions were less effective toward the attainment of resolved and strongly supported clades of all species. In summary, robustly supported clades of P. regnellii were obtained in most of the analyses, based either on isolated or combined sequences. The SSRs primers Psol 3, Psol 6 and Psol 10 were shown to be transferable to P. gaudichaudianum and P. regnellii, but not to P. malacophyllum. Preliminary cluster analyses based on the polymorphism of the amplified products suggested that Psol 3 has lower potential than Psol 6 and Psol 10 for discrimination of Piper species.

Generic relationships and dating of lineages in Winteraceae based on nuclear (ITS) and plastid (rpS16 and psbA-trnH) sequence data.

Phylogenetic analyses of representative species from the five genera of Winteraceae (Drimys, Pseudowintera, Takhtajania, Tasmannia, and Zygogynum s.l.) were performed using ITS nuclear sequences and a combined data-set of ITS+psbA-trnH+rpS16 sequences (sampling of 30 and 15 species, respectively). Indel informativity using simple gap coding or gaps as a fifth character was examined in both data-sets. Parsimony and Bayesian analyses support the monophyly of Drimys, Tasmannia, and Zygogynum s.l., but do not support the monophyly of Belliolum, Zygogynum s.s., and Bubbia. Within Drimys, the combined data-set recovers two subclades. Divergence time estimates suggest that the splitting between Drimys and its sister clade (Pseudowintera+Zygogynum s.l.) occurred around the end of the Cretaceous; in contrast, the divergence between the two subclades within Drimys is more recent (15.5-18.5MY) and coincides in time with the Andean uplift. Estimates suggest that the earliest divergences within Winteraceae could have predated the first events of Gondwana fragmentation.

Tibouchina pulchra (Cham.) Cogn., a native Atlantic Forest species, as a bio-indicator of ozone: visible injury.

Tibouchina pulchra saplings were exposed to carbon filtered air (CF), ambient non-filtered air (NF) and ambient non-filtered air+40 ppb ozone (NF+O3) 8 h per day during two months. The AOT40 values at the end of the experiment were 48, 910 and 12,895 ppb h(-1), respectively, for the three treatments. After 25 days of exposure (AOT40=3871 ppb h(-1)), interveinal red stippling appeared in plants in the NF+O3 chamber. In the NF chamber, symptoms were observed only after 60 days of exposure (AOT40=910 ppb h(-1)). After 60 days, injured leaves per plant corresponded to 19% in NF+O3 and 1% in the NF treatment; and the average leaf area injured was 7% within the NF+O3 and 0.2% within the NF treatment. The extent of leaf area injured (leaf injury index) was mostly explained by the accumulated exposure of ozone (r2=0.89; p<0.05).

Corrigendum to "Antioxidant Activity of a Geopropolis from Northeast Brazil: Chemical Characterization and Likely Botanical Origin".

[This corrects the article DOI: 10.1155/2017/4024721.].

Antiproliferative and antioxidant activities of a tricin acylated glycoside from sugarcane (Saccharum officinarum) juice.

From sugarcane juice, a flavone, identified by spectroscopic methods as tricin-7-O-beta-(6''-methoxycinnamic)-glucoside, was isolated, in addition to orientin. The tricin derivative was shown to have antioxidant activity higher than Trolox by means of the DPPH assay and lower by the beta-carotene/linoleic acid system. It showed in vitro antiproliferative activity against several human cancer cell lines, with higher selectivity toward cells of the breast resistant NIC/ADR line.

Effects of initial climatic conditions on growth and accumulation of fluoride and nitrogen in leaves of two tropical tree species exposed to industrial air pollution.

Saplings of Tibouchina pulchra and Psidium guajava, cultivated under standardized soil conditions, were placed in two sites at Cubatão (state of São Paulo, southeast Brazil) to study the effects of air pollution on growth, biomass allocation and foliar nitrogen and fluoride concentrations. Thirty-six potted plants were maintained over two periods of one year (Jul/00 to Jun/01; Dec/00 to Nov/01) at each of two experimental sites with distinct levels of air pollution: Pilões River Valley (PV) with vegetation virtually unaffected by air pollution; and Mogi River Valley (MV) severely affected by pollutants released mainly by chemical, fertilizer, iron and steel industries. For both species, saplings growing at MV showed alterations of growth and biomass allocation, as well as increased leaf concentrations of nitrogen and fluoride. Comparing both experimental periods, the one starting in winter (the driest season in Southeastern Brazil) seemed to affect the saplings more severely, the differences of the measured parameters between MV and PV being higher than in the second period. Multivariate analysis revealed two groups of data: one representing the MV and the other the PV saplings. For both species, saplings growing at MV showed differences in chemical composition, growth and biomass allocation, compared with the PV saplings. The results suggested that seasonal conditions of the first months of sapling exposure (summer or winter) modulate the intensity of responses to pollution stress.

Antioxidant Activity of a Geopropolis from Northeast Brazil: Chemical Characterization and Likely Botanical Origin.

Geopropolis is a product containing wax, plant resin, and soil particles. It is elaborated by stingless bees of tribe Meliponini. Methanol extracts of sample of geopropolis produced by Scaptotrigona aff. depillis [corrected] ("mandaguari") in the state of Rio Grande do Norte (RN, northeast Brazil) were analyzed for the determination of standard parameters (total phenols, total flavonoids, and radical scavenging activity) and chemical characterization by HPLC-DAD-MS/MS analysis. The sample analyzed has high contents of total phenols and flavonoids, as well as high antioxidant activity. The constituents characterized were mainly flavonols, such as quercetin methyl ethers, and methoxychalcones. Such chemical profile is similar to the composition of a green propolis from the same area of RN, which is produced by Africanized Apis mellifera, using shoot apices of Mimosa tenuiflora, popularly known as "jurema-preta." This finding provides evidence that "mandaguari" geopropolis and honeybee propolis have the same botanical origin in RN. The sharing of a plant resin source by phylogenetically distant bees (Apinae and Meliponinae) suggests that bee genetic factors play little role in the choice of plants for resin collection and that the availability of potential botanical sources plays a decisive role.

A highly complex stingless bee propolis: composition and influence of the period of collection

BACKGROUND Stingless bees or meliponines (family Apidae, subfamily Meliponinae, tribe Meliponini) are eusocial bees from tropical and subtropical regions. Propolis of Scaptotrigona aff. Postica (Latreille, 1807) is used in the state of Maranhão (Northeast Brazil) in ointments to treat tumors and wounds. Samples of propolis of Scaptotrigona aff. Postica (Apidae, Meliponini) were collected monthly from an apiary located in Barra do Corda (state of Maranhão, northeast Brazil). Extracts of the twelve samples were obtained with 80% ethanol. Constituents of the samples were characterized by HPLC-PAD-ESI-MS/MS analysis, amounting to 100 substances. RESULTS Representatives of several classes of secondary metabolites were characterized, including benzoic and cinnamic acids, flavonoids (chalcones, flavone-C-glycosides, flavonol aglycones and glycosides), alkyl and alkenyl resorcinols, xanthones, diterpenes, cycloartane-type triterpenoids, pentacyclic triterpenoids, pyrrolizidine alkaloids and hydroxycinnamic acid amides (HCAAs). Considerable qualitative differences in chemical composition among samples were observed, depending on the year period of collection. Principal Coordinate Analysis recognized three distinct year periods (Jan-Mar, April-Sep, Oct-Dec) according to the corresponding chemical profiles. CONCLUSION Comparing with previous studies, the present work indicates that considerable differences in chemical composition occur also from year to year. Contrary to most propolis types reported so far, which derives exclusively or mostly from a single botanical source, the propolis from Barra do Corda seemingly depends on several resin sources. It is suggested that chalcones and flavonols stem from Mimosa tenuiflora (Mimosoideae); resorcinols, xanthones and cycloartane-type triterpenoids, from fruits of Mangifera indica (Anacardiaceae); pyrrolizidine alkaloids, possibly from some Crotalaria species (Faboideae); HCAAs probably originate from pollen contaminating the propolis samples. The propolis of S. aff. Postica poses challenges and possibilities of study for apicultural researchers, chemists and pharmacologists.