This work describes the isolation of pure bergenin from Peltophorum dubium roots with good yields and its further derivatization through Williamson synthesis. The alkyl derivatives of the bergenin were identified by nuclear magnetic resonance and mass spectrometry data analysis. Among them, three derivatives were reported for the first time herein, 8,10-dihexyl-bergenin, 8,10-didecyl-bergenin, and 8,10-ditetradecyl-bergenin, along with three previously reported ones (8,10-dimethylbergenin, 8-methylbergenin, 8,10-dioctyl-bergenin). Most derivatives of the bergenin displayed moderate cytotoxicity against Artemia salina, except the 8,10-dihexyl-bergenin (lethal concentration doses for 50% (LC50) = 70.55 µg mL-1). The antimicrobial assay showed that all derivatives selectively inhibited the Gram-positive bacteria Staphylococcus aureus, and two of them (8,10-dihexyl-bergenin and 8,10-didecyl-bergenin) had promising activities (minimum inhibitory concentration (MIC) = 5.1-6.2 µmol L-1). In addition, bergenin displayed interesting inhibition on acetylcholinesterase (half maximal inhibitory concentration (IC50) = 141.19 ± 0.41 µmol L-1), while its semi-synthetic derivatives displayed modest activity. Our results revealed that the antibacterial activity of bergenin could be greatly improved through its structural modification.

This work describes the chemical composition of MeOH seeds and flowers extracts of Tapirira guianensis, a known tree that occurs in the Brazilian Atlantic forest. The CH2Cl2 soluble fraction of seeds extract was submitted to chromatographic procedures to obtain a mixture of new alkenyl dihydrobenzofuranoids which were identified as 2-[(10’Z)-dodec-10’-enyl]-dihydro-1-benzofuran-5-ol, 2-[(10’Z)-tridec-10’-enyl]-dihydro-1-benzofuran-5-ol e 2-[(10’Z)-pentadec-10’-enyl]-dihydro-1-benzofuran-5-ol (1 - 3) besides β-sitosterol. From the EtOAc soluble fraction of flowers MeOH extract quercetin, quercitrin and gallic acid were obtained by chromatographic techniques. The fatty acid composition of oils from leaves and seeds were also determinate and the leaves’ oil is composed by 63.94% of saturated and 36.04% of unsaturated fatty acids while in the seeds the oil present 42.13% of saturated and 57.87% of unsaturated. All compounds and derivatives were identified by their spectrometric data analysis. The brine shrimp test of the extracts showed the seed CH2Cl2 and the EtOAc and BuOH soluble fractions of the flowers were actives and, the alkyl phenols are the responsible for this moderate activity. The antioxidant tests of the extracts indicated EtOAc soluble fraction of MeOH extract of flowers showed better results possibly due the presence of flavonoids and gallic acid.

Spondias mombin L. is a Brazilian tree belonging to the family Anacardiaceae and popularly known as “cajá”, the genus is well known by the various exotic fruit species such as “siriguela” (S. purpurea), “umbu” (S. tuberosa) and “umbu-cajá” (S. bahiensis). It presents commercial importance to the locals especially due the small juice fruit industries and the seeds are often discarded as waste after pulping. Despite the regional importance, even today there is little information on the chemical composition of these fruits. Thus, the dichloromethane extract of the waste seeds of S. mombin was subjected to different chromatographic fractionation allowing the isolation of a main triglyceride identified as 1,3-dioleoyl-2-linoleoyl glycerol, two new alkyl phenols named 1-hydroxyl-3-[(Z)-10’-octadecenyl]-benzene and 1-hydroxyl-3-[(Z)-10’-docosenyl] benzene, and a mixture of phytosteroids. The seed’s fatty acid profile and the cytotoxicity of the oils and isolated compounds were also determinated employing BST. The alkenylphenol mixture present some toxicity (CL50 215,4 µg mL-1) in this test.

ABSTRACT The profile of volatile organic compounds, the glandular and non-glandular trichomes of Plectranthus ornatus, obtained by in vitro cultivation, was evaluated in plants grown in Murashide and Skoog medium supplemented with benylaminopurine at 4.5, 9.0, and 18.0 µM + naphthaleneacetic acid at 5.37 µM, kinetin at 4.7, 9.3 and 18.5 µM + naphthaleneacetic acid (5.37 µM) or Murashide and Skoog 0 medium (as a control). Scanning Electron Microscopy was performed on samples of the third leaf node of the 90 days old plants obtained from treatment with 4.5 or 9.0 µM benylaminopurine, and 4.7 or 9.3 µM kinetin. Headspace Solid Phase Micro-Extraction of the 30, 60 and 90 days old in vitro plants permitted to determinate by GC/MS the composition comprised of 62 compounds. The data were analyzed using Principal Component Analysis and Hierarchical Clustering Analysis and, the major constituents of these oils after treatment and aging were monoterpenes and sesquiterpenes. Morphoanatomical analysis of trichomes, by Scanning Electron Microscopy, enabled the identification of non-glandular trichomes and four types of glandular trichomes, which comprised capitate and peltate glandular trichomes that were distributed on both sides of the leaf. We observed that the regulators influenced qualitative and quantitative profiles of the volatile organic compounds and the number and distribution of hairs on the leaf surface.

ABSTRACT This work describes the establishment of procedures to induce in vitro callogenesis from Poincianella pyramidalis (Tul.) L. P. Queiroz, Fabaceae, explants. Nodal, internodal and leaf segments were isolated from in vitro germinated seedlings and cultured in MS medium with 0, 2.5, 5 and 10 mg l-1 of 2,4-dichlorophenoxyacetic acid. After 30 days, the explants with induced callus showed a quadratic response for the segments nodal, internodal and leaf, with increasing the callus formation in 2,4-dichlorophenoxyacetic acid concentrations of 6.28, 6.49 and 4.91 mg l-1, respectively. In 30 days there was a linear oxidation rise with the increase to the 2,4-dichlorophenoxyacetic acid. After 60 days, oxidation values were minimum, at 2,4-dichlorophenoxyacetic acid concentrations of 5.13 mg l-1 (internodal) and 3.98 mg l-1 (leaf). The highest callus production was observed after 30 days in the presence of 6.09 mg l-1, 5.82 mg l-1 and 4.91 mg l-1 of 2,4-dichlorophenoxyacetic acid in nodal, internodal and leaf segments, respectively. After 60 days these segments showed peaks of production at 7.0 mg l-1 (nodal), 6.15 mg l-1 (internodal) and 5.08 mg l-1 (leaf) of 2,4-dichlorophenoxyacetic acid. For callus induction the intake of 2,4-dichlorophenoxyacetic acid was essential. The greater intensity in callus formation was observed in 4.91 mg l-1 in leaf segments after 30 days.

This work describes the tissue culture of Plectranthus ornatus Codd. (Lamiaceae) on Murashige and Skoog (MS) medium with naphthalene acetic acid (NAA) (1.0, 2.0 and 4.0 mg L-1) and 6-benzylaminopurine (BAP) (1.0, 2.0 and 4.0 mg L-1) as growth regulators to obtain the overproduction of rosmarinic acid. The content of rosmarinic acid and its biosynthetic precursors were determined by high performance liquid chromatography (HPLC). The antioxidant activities (AA) of the extracts were also evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. The best growing condition was observed with the addition of 1.0 mg L-1 of both NAA and BAP in the culture medium yielded an increase of 94 times of rosmarinic acid comparing with the wild plant. All extracts diplayed antioxidant activity, as evidenced by the DPPH free radical scavenging assay. However, those with 2.0 mg L-1 NAA and, 1.0 mg L-1 NAA and BAP in culture medium showed the lowest EC50 (26.0 and 29.8 µg mL-1, respectively). At concentration higher than 10 µg mL-1 of rosmarinic acid it was not observed the correlation with AA, suggesting some other anti-oxidant mechanism acting.

This work describes a method for the determination of gallic, caffeic and p-coumaric acids, as well as quercetin, in Brazilian red wines by employing reverse phase high performance liquid chromatography (RP HPLC) coupled to diode array and mass detectors. The method was performed using a sample volume of 10 µL. The limits of detections were 0.36, 0.27, 0.33 and 0.59 mg L-1 for gallic acid, caffeic acid, p-coumaric acid and quercetin, respectively. The precision, as estimated by the relative standard deviation, was between 1.0 and 2.0% for different concentrations of gallic acid, caffeic acid, p-coumaric acid and quercetin. The accuracy was evaluated by addition and recovery experiments, and the obtained values were between approximately 92 and 117% recovery. The method was then applied to the analysis of red wine samples that were collected from the São Francisco region, Bahia State, Brazil. The concentrations of analytes were determined in ten Brazilian wines and varied from 5.26 to 10.22 mg L-1 for quercetin, 6.65 to 43.92 mg L-1 for gallic acid, 3.58 to 7.83 mg L-1 for p-coumaric acid, and 3.59 to 10.5 mg L-1 for caffeic acid.

Chemical investigation of the MeOH extract of root barks of P. pyramidallis (Tul.) L. P. Queiroz resulted in the isolation of 3,3'-dimethylellagic acid and 3,3'-dimethylellagic acid-4'-O-β-D-xyloside. Lupeol, β-sitosterol/stigmasterol and the mixture of fatty acid methyl ester derivatives were also obtained. Chromatographic procedures of the MeOH extract of the flowers of this species led to obtain an unusual mixture of fatty alcohols, β-sitosterol/stigmasterol, α-amyrin, β-amyrin and methyl gallate. The structures of the isolates were established by spectral data analysis. This is the first occurrence of 3,3'-dimethylellagic acid, 3,3'-dimethylellagic acid-4'- O-β-D-xyloside and free fatty alcohols in the Fabaceae family.

<p>Phytochemical investigation of the MeOH extract of Schinopsis brasiliensis Engl. stems led to the isolation of the new biflavanone (2R*,3R*,2''R*,3''R*)-7-hydroxy-4'-methoxy-flavanone- (3→3'')-3''',7''-dihydroxy-4'''-methoxy-flavanone and 4,2',4'-trihydroxychalcone-(3→O→4'')- 2''',4'''-dihydroxychalcone, whereas methyl gallate, gallic acid, (6R,9R)-megastigma-4-en-3-one- 9-O-β-glucopyranoside, quercetin-3-O-β-D-xylopyranoside and tricetin-3'-O-β-D-glucopyranoside were isolated from the MeOH extract of leaves. Their chemical structures were elucidated using spectroscopic methods and comparison with the literature data. Both biflavonoids showed weak inhibition activities of acetyl and butyrylcholinesterase enzymes when compared with eserine.</p>

Podophyllotoxin is the most studied lignan because of its use as an antimitotic agent and because it is a precursor of pharmacologically active derivatives. This review describes the anticancer activities of podophyllotoxin and the different processes that have been developed for its extraction and purification from Podophyllum spp. In addition, the synthesis routes of this compound and the development of three semi-synthetic procedures to obtain etoposide, teniposide, and Etopophos are detailed.

This study describes the isolation and identification of apigenin-7-O-ghicopyranoside, a flavonoid isolated from the flowers of Bellis perennis L., Asteraceae, an species with a broad spectrum of biological activities. The in vitro antioxidant activity and the inhibition of the enzyme acetylcholinesterase were evaluated. The flavonoid showed strong in vitro antioxidant potential, because of the capacity of removal of hydroxyl radicals and nitric oxide, and also prevented the formation of thiobarbituric acid-reactive substances. These parameters were inhibited at the highest concentration of ApG at rates of 77.7%, 72% and 73.4%, respectively, in addition to inhibiting acetylcholinesterase, suggesting potential use in the treatment of neurodegenerative diseases.

Approximately 600-700 species of Ipomoea, Convolvulaceae, are found throughout tropical and subtropical regions of the world. Several of those species have been used as ornamental plants, food, medicines or in religious ritual. The present work reviews the traditional uses, chemistry and biological activities of Ipomoea species and illustrates the potential of the genus as a source of therapeutic agents. These species are used in different parts of the world for the treatment of several diseases, such as, diabetes, hypertension, dysentery, constipation, fatigue, arthritis, rheumatism, hydrocephaly, meningitis, kidney ailments and inflammations. Some of these species showed antimicrobial, analgesic, spasmolitic, spasmogenic, hypoglycemic, hypotensive, anticoagulant, anti-inflammatory, psychotomimetic and anticancer activities. Alkaloids, phenolics compounds and glycolipids are the most common biologically active constituents from these plant extracts.

This manuscript describes an update review with up to 285 references concerning the occurrence of amides from a variety of species of the genus Piper (Piperaceae). Besides addressing occurrence, this review also describes the biological activities attributed to extracts and pure compounds, a compiled 13C NMR data set, the main correlations between structural and NMR spectroscopic data of these compounds, and employment of hyphened techniques such as LC-MS, GC-MS and NMR for analysis of amides from biological samples and crude Piper extracts.

Polygalaceae is represented in Brazil by ten genera and 191 species, of which the Polygala is the most representative, characterized by the occurrence of methyl salicylate. Seventeen species of Polygalaceae have been analyzed by HPLC-DAD and the technique proved to be selective, precise, accurate, and with low limits of quantification and detection. The analysis of plant material confirmed the presence of methyl salicylate, with concentration values ranging from 14.1 a 126.9 µg/g.

This work describes the phytochemical study of stem bark and leaves of Cenostigma macrophyllum Tul. (Leguminosae). Through usual chromatographic techniques were isolated bergenin as the primary compound of the stem bark of and from the leaves gallic acid, methyl gallate, ellagic acid, quercetin, quercetin-3-O-β-D-glucopyranoside, quercetin-3-O-(6"-O-galloyl)-β-D-glucopyranoside (tellimoside), quercetin-3-O-(6"-O-E-p-coumaroyl)-β-D-glucopyranoside (helichrysroside), agathisflavone and vitexin were obtained. The isolates were identified by spectroscopic data analysis, and bergenin showed dose-related antinociception when assessed in acetic acid-induced writhing in mice.