Scielo RSS <![CDATA[Revista Brasileira de Farmacognosia]]> vol. 28 num. 2 lang. es <![CDATA[SciELO Logo]]> <![CDATA[Anatomy and volatile oil chemistry of <em>Eucalyptus saligna</em> cultivated in South Brazil]]> ABSTRACT Eucalyptus saligna Sm., Myrtaceae, commonly known as Sydney blue gum, is often confused with several other species in the genus. The leaf volatile oils of the species have been reported to have antimicrobial, insecticidal, nematicidal, repellent and cytotoxicity properties. The present work provides anatomy as well as volatile oil chemistry of the species collected from South Brazil. The anatomy and histochemistry of the leaves and stems were investigated by light and scanning electron microscopy, and the leaf and stem volatile oils were analyzed by GC–MS. Amphistomatic leaves, anomocytic stomata, presence of papillae and epicuticular waxes, slightly biconvex midrib with a bicollateral vascular bundle in open arc and two dorsal traces, secretory cavities, calcium oxalate druses and prismatic crystals, rounded petiole with a bicollateral vascular bundle in open arc with invaginated ends and rounded stem with sclerenchyma abutting the internal and external phloem are observed in this species. The main components of the volatile oil were p-cymene (28.90%) and cryptone (17.92%). These characteristics can help in the identification and quality control of E. saligna. <![CDATA[Influence of abiotic environmental factors on the main constituents of the volatile oils of <em>Tithonia diversifolia</em>]]> ABSTRACT Tithonia diversifolia (Hemsl.) A. Gray, Asteraceae, commonly known as Mexican sunflower, is a wide distributed invasive species encountered around the world. We proposed herein to establish the relationship between different abiotic environmental factors and the variation in the production of volatile compounds in T. diversifolia, during a period of one year. Samples of leaf and inflorescence volatile oils obtained from individuals located at two different regions of Brazil were analyzed by GC–MS and the data were submitted to chemometric analysis. Based on the main constituents, the analysis allowed us to classify the volatile oils into two chemotypes, according to their geographical origin. The influence of soil nutrients, mainly Ca and P, was also observed in the composition of the volatile oils. Climate also seems to affect the constituents of the volatile oils, mainly the contents of leaf sesquiterpenes of individuals growing in areas with higher average temperatures and solar radiation levels. We can therefore highlight that the appropriate multivariate statistical analysis allowed us to propose for the first time the existence of chemotypes for the volatile oils of T. diversifolia, as well as reporting the main abiotic environmental factors related to the accumulation of the discriminant compounds in these oils. <![CDATA[Optimization of extraction method and HPLC analysis of six caffeoylquinic acids in <em>Pluchea indica</em> leaves from different provenances in Thailand]]> ABSTRACT Pluchea indica (L.) Less., Asteraceae, is a medicinal plant which contains a high amount of phenolic compounds such as caffeoylquinic acid derivatives. The leaves have been traditionally used as a nerve tonic and extensively as herbal tea. This study aimed to develop and validate an HPLC method to quantitatively analyze six caffeoylquinic acid derivatives, viz. 3-O-caffeoylquinic acid, 4-O-caffeoylquinic acid, 5-O caffeoylquinic acid, 3,4-O-dicaffeoylquinic acid, 3,5-O-dicaffeoylquinic acid, and 4,5-O-dicaffeoylquinic acid in P. indica leaf extract. HPLC was carried out in a Hypersil BDS C18-column eluted with 0.5% acetic acid in water and methanol using gradient elution with a flow rate of 1 ml/min and detection at 326 nm. The method validation was performed to assure its linearity, precision, accuracy and limits of detection and quantitation. Several extraction techniques including maceration, decoction, digestion, Soxhlet extraction, and ultrasound extraction, were used to extract active constituents. The ultrasound extraction with 50% ethanol yielded the highest concentration of these caffeoylquinic acid derivatives in the P. indica leaf extract. Our developed HPLC method is simple and reliable for a routine analysis of the six caffeoylquinic acids in P. indica leaves and could potentially be applied to be used in commercial herbal products. <![CDATA[Optimization of baicalin water extraction process from <em>Scutellaria baicalensis</em> (a traditional Chinese medicine) by using orthogonal test and HPLC]]> ABSTRACT In this study, we optimized the baicalin water extraction process from Scutellaria baicalensis Georgi, Lamiaceae (a traditional Chinese medicine). Orthogonal test design L9(3)4 was used to analyze the optimization of water extraction process of baicalin from S. baicalensis. The effect of solid–liquid ratio, extraction time and soaking time on the yield of baicalin were investigated and optimized by orthogonal test. High-performance liquid chromatography was employed for the determination of extraction yield of baicalin. Analysis of variance was carried out to study the effects of the above three factors. The results showed that solid–liquid ratio plays a significant role in attaining maximum extraction yields of baicalin. However, the other two factors had some effect (not statistically significant) on the extraction yield of baicalin. Conclusively, the optimum experimental conditions such as the solid–liquid ratio (1:12), extraction time (30 min) and soaking time (1 h) for the water extraction of baicalin were proposed which can provide the maximum extraction yield of baicalin. In addition, the score based on the content of baicalin and total solid residues yield were used as evaluation indexes for baicalin uterus suppositories evaluation. <![CDATA[Simultaneous determination of six bioactive components of total flavonoids of <em>Scorzonera austriaca</em> in rat tissues by LC-MS/MS: application to a tissue distribution study]]> ABSTRACT A liquid chromatography-tandem mass spectrometry method was developed and validated for simultaneous determination of six bioactive constituents including vitexin, orientin, isoorientin, 2"-O-β-D-xylopyranosyl isoorientin, 2"-O-β-D-xylopyranosyl isovitexin, and 6-C-L-α-arabipyranosyl vitexin in rats’ various tissues using isoquercitrin as the internal standard. Biological samples were pretreated by protein precipitation with acetonitrile. Chromatographic separation was carried out on a C18 column with a gradient mobile phase consisting of acetonitrile and 0.1% aqueous formic acid. All analytes and internal standard were quantitated through electrospray ionization in negative ion selected reaction monitoring mode. The mass transitions were as follows: m/z 431 → 311 for vitexin, m/z 447 → 327 for orientin or isoorientin, m/z 579 → 459 for 2"-O-β-D-xylopyranosyl isoorientin, m/z 563 → 293 for 2"-O-β-D-xylopyranosyl isovitexin, m/z 563 → 353 for 6-C-L-α-arabipyranosyl vitexin, and m/z 463 → 300 for the internal standard, respectively. The lower limits of quantification for the six analytes in different tissue homogenates were 0.8–2.2 ng/ml. The validated assay was successfully applied to a tissue distribution study of the six components in rats after intravenous administration of total flavonoids of Scorzonera austriaca Willd; Asteraceae. The results of the tissue distribution study showed that the high concentrations of six components were mainly in the kidney. <![CDATA[Artichoke edible parts are hepatoprotective as commercial leaf preparation]]> ABSTRACT Chemical profile analyses of artichoke (Cynara scolymus L., Asteraceae) edible parts (fleshy receptacle, inner bracts) as well as roots are compared with the commercially usable leaf extract using HPLC-DAD-ESI-MS via chlorogenicacid as a marker. Overall polyphenolic constituents demonstrated by means of LC/MS profiling. The nutritional values and inulin contents of different assessed parts were investigated. The present study was designed to determine the effect of artichoke: leaves, bracts, receptacles and roots alcoholic extracts against CCl4-induced acute hepatotoxicity and hyperlipidemia in rats by means of histopathological and biochemical parameters. Serum liver enzymes levels of aspartate amino transferase, alanine amino transferase, alkaline phosphatase and lipid peroxidase content (malondialdehyde MDA) were estimated. Blood glutathione, total cholesterol, triacylglycerides and high density lipid level were estimated in plasma. The ethanol extract of roots, leaves, bracts and receptacles were standardized to (0.82 ± 0.02, 1.6 ± 0.06, 2.02 ± 0.16 and 2.4 ± 0.27 mg chlorogenic acid/100 mg extract), respectively. The receptacle showed the highest content of polyphenols and exhibits the highest antioxidant activity. HPLC analysis of inulin in the receptacles of globe artichoke revealed high content of inulin (41.47 mg/g) dry extract. All artichoke parts contain comparable vitamins and minerals. Artichokes receptacles extract when taken in dose of (500 mg/kg/day) reduce the lesion caused by CCl4 alone more than groups receiving silymarin. Bracts and leaves extract exert nearly the same effect. <![CDATA[Comparison of bioactive compounds content in leaf extracts of <em>Passiflora incarnata, P. caerulea</em> and <em>P. alata</em> and <em>in vitro</em> cytotoxic potential on leukemia cell lines]]> ABSTRACT Passiflora caerulea L., P. alata Curtis and P. incarnata L. (synonym for P. edulis Sims), are the most popular representatives of the Passiflora genus in South America. In recent years, a growing attention is paid to the biological activity and phytochemical profiles of crude extracts from various species of Passiflora in worldwide. The aim of this study was to evaluate and to compare of anti-leukemic activity of the dry crude extracts from leaves of three Passiflora species from greenhouse of Poland in two human acute lymphoblastic leukemia cell lines: CCRF-CEM and its multidrug resistant variant. Two systems of liquid chromatography in order to assessment of phytochemical composition of extracts were applied. Extracts of P. alata and P. incarnata showed the potent inhibitory activity against human acute lymphoblastic leukemia CCRF-CEM, while P. caerulea not showed activity (or activity was poor). Despite similarities in quality phytochemical profile of extracts from P. caerulea and P. incarnata, differences in quantity of chemical compounds may determine their various pharmacological potency. For the activity of P. alata extract the highest content of terpenoids and a lack of flavones C-glycosides are believed to be crucial. Summarizing, the crude extract from P. alata leaves may be considered as a substance for complementary therapy for cancer patients. <![CDATA[Zornioside, a dihydrochalcone <em>C</em>-glycoside, and other compounds from <em>Zornia brasiliensis</em>]]> ABSTRACT The secondary metabolites of the aerial parts of Zornia brasiliensis Vogel, Fabaceae, and the biological activity of one of these secondary metabolites were characterized in this study. A phytochemical investigation was performed using chromatographic techniques including analytical and preparative reverse-phase HPLC column sequences, which resulted in the isolation of fourteen compounds: one previously undescribed C-glycosylated dihydrochalcone (zornioside), one cyclitol (D-pinitol), one glycosylated megastigmane (roseoside) and eleven phenolic compounds: 7-methoxyflavanone, 7,4'-dimethoxyisoflavone, medicarpin, 2'-4'-dihydroxychalcone, onionin, isoorientin-3'-O-methyl ether, isovitexin, glycosylated (Z)-O-coumaric acid, glycosylated (E)-O-coumaric acid, dihydromelilotoside, and isoorientin. The structures of the isolated compounds were determined based on 1D and 2D-NMR, HRESIMS, IR and CD spectroscopic analyses. The cytotoxic activity of zornoside was assessed against tumor cell lines (MCF-7, HCC1954, T-47D, 4T1, HL60), and a non-tumor cell line (RAW264.7) using MTT assay. The compound zornioside was selectively cytotoxic for HL60 leukemia cells (IC50: 37.26 µM). <![CDATA[In vivo anti-arthritic and antioxidant effects from the standardized ethanolic extract of Moussonia deppeana]]> ABSTRACT Moussonia deppeana (Schltdl. &amp; Cham.) Klotzsch ex Hanst., Gesneriaceae, known as tlachichinole, is a Mexican medicinal plant used for treatment of chronic inflammation-related diseases such as arthritis. In this paper, the main metabolite verbascoside was quantified in ethanolic extract; anti-arthritic and antioxidant activities were also evaluated in Complete Freund's Adjuvant induced arthritis in mice, with complete hematological evaluation, and oxidative stress measure in edema and ganglionic tissues on day 28. In popliteal ganglion, CD4+ lymphocytes and tumor necrosis factor alpha concentration were measured in addition to histological analysis. Ethanolic extract contained 79.2 mg of verbascoside/g extract, and this extract at 450 mg/kg generated an inhibition of 24% over paw edema development and increased body weight gain on final day. For hematological parameters, same dose decreased total leukocytes and lymphocytes, as well as decreased oxidation rate over biomolecules in edema and ganglionic tissues, and increased antioxidant enzyme activity. In ganglionic tissue, CD4+ lymphocytes and tumor necrosis factor alpha level showed no differences at any tested dose compared to complete Freund's adjuvant untreated group. Histological analysis of popliteal ganglion revealed moderate reduction of follicular hyperplasia, leukocyte infiltration and lipid inclusions at 450 mg/kg dose. Ethanolic extract of M. deppeana possesses anti-edematous activity associated to a moderate reduction in follicular hyperplasia, with immune-modulatory and antioxidant effects during experimental arthritis in mice. <![CDATA[<em>In vivo</em> study of a homeopathic medicine against <em>Rhipicephalus</em> (<em>Boophilus</em>) <em>microplus</em> in dairy cow]]> ABSTRACT The tick Rhipicephalus (Boophilus) microplus (Canestrini, 1887) (Acari: Ixodidae) causes large economic losses to cattle breeders and its control is hampered by problems of resistance to the main commercial synthetic acaricides and the risk of residues in animal products. Alternative controls are important for the sustainability of cattle breeding in tropical regions, principally for organic milk production. This study evaluated the efficacy of a homeopathic preparation to control natural tick infestations. The evaluations were conducted with 24 taurine dairy cows during 12 months. The homeopathic medicine (30 CH + Sulfur 30 CH) was administered in a proportion of 1:100 (v/w) in a formulation with sugar, added to 30 kg of mineral salt. This preparation was supplied along with concentrated feed (2 kg/animal/day). The control group received the same feed mixture without the medicine. The groups were kept in separate paddocks. Data were collected on body weight, packed cell volume and number of engorged female ticks on each animal. Temperature, relative humidity and rainfall were recorded. Engorged females were collected from each group for in vitro comparison of reproductive parameters, and semi-engorged ticks for morpho-histological analysis. The mean results of body weight, packed cell volume and tick number were not statistically different between the control and treated groups: 616.5 kg and 618.6 kg; 27.9% and 27.3%; and 12.19 and 13.58 ticks, respectively. In the in vitro analyses, the average weights of the ticks (0.18 and 0.17 g) and eggs (0.07 and 0.06 g), larval hatching rate (70.1 and 76.6%) and reproductive efficiency index (54.3 and 60.6%) of the control and treated groups, respectively, also were not statistically different. Furthermore, no alteration in the ovaries was detected by microscopic analysis. Therefore, the homeopathic medicine was ineffective to control R. (B.) microplus, although the inclusion of agro-ecological practices might enhance its effect of homeopathy in controlling tick infestations. <![CDATA[Development and clinical efficacy evaluation of anti-greasy green tea tonner on facial skin]]> ABSTRACT Green tea (Camellia sinensis (L.) Kuntze, Theaceae) polyphenols have activities against skin disorders; however, anti-sebum efficacy of green tea cosmetic has sparely been reported. The facial tonner containing green tea was therefore developed and clinical evaluated. The base formulas which stabled following accelerated tests were sensorial assessed in ten volunteers. The base with hydroxyethyl cellulose, glycerin and panthenol (totally 3.6%) with the significant (p &lt; 0.05) preference (82.3 ± 0.55%) over the others was further developed to green tea preparations. All of the products were stable and caused none of skin irritation as closed patch tested in twenty volunteers. Thereafter, they were clinical evaluated in the same group of the volunteers and monitored with Sebumeter® by means of a split-face, randomized single-blind, placebo-controlled study. Anti-greasy efficacy of 2, 4.5 and 7% green tea tonners were 3.47 ± 0.10, 8.18 ± 0.44 and 17.87 ± 0.46% following 14 days of facial treatment. The efficiency was pronounced at the end of the study; day 28 (8.48 ± 0.13, 20.26 ± 1.03 and 31.57 ± 1.22%). Anti-sebum efficacy of the 4.5 and 7% green tea tonners were significantly better than the base formula (day 14; p &lt; 0.05, day 28; p &lt; 0.01). The efficacy of 28 days treatment was significantly better than 14 days (p &lt; 0.05). The safe and efficient green tea tonner for oily face treatment was therefore approved in this context. <![CDATA[Randomized controlled trial of <em>Panax ginseng</em> in patients with irritable bowel syndrome]]> ABSTRACT The irritable bowel syndrome is defined as the presence of continuing or recurrent abdominal pain and it is associated with altered bowel habit. Experimental studies with Panax ginseng C.A. Mey., Araliaceae, have demonstrated the antinociceptive action on calcium and sodium channels, as well as on primary sensory neurons. A clinical double-blind, randomized, prospective and experimental trial was conducted for sixty days, comparing the action of dry extract of P. ginseng (300 mg/day) with trimebutine (600 mg/day). Patients were assessed at four visits for abdominal pain, using the Likert scale, and adverse events. Twenty-four patients completed the study, being 87.5% female and mean age of 47.41 years. There was improvement in abdominal pain, through Likert scale values, in patients who used P. ginseng. This group started from a median basal of −5 to 2.5, 3 and 5 in the 1st, 4th and 8th weeks of treatment, respectively, with a statistically significant difference. Similar results were achieved in those patients who used trimebutine. The only adverse effect observed was the occurrence of headache in two patients (16.66%) in the group that used the herbal. The research suggests that P. ginseng was effective in the control of abdominal pain in irritable bowel syndrome patients, analogous to trimebutin, and may be used in future studies for a better evaluation of the obtained results. <![CDATA[Morpho-anatomy of native species used as substitute of quina (<em>Cinchona</em> spp.) in Brazilian traditional medicine: <em>Esenbeckia febrifuga</em>]]> ABSTRACT Esenbeckia febrifuga (A.St.-Hil.) A. Juss. ex Mart., Rutaceae, is known by several popular names including quina-do-mato. This name is a reference to the use of its bark as febrifuge and in the past was employed as a substitute of Cinchona sp. for treatment of malaria symptoms. This confusion may have been reinforced by the fact that the bark of these plants are similar in appearance and have a bitter taste. In view thereof this study presents the description morphological and anatomical and the histochemistry of the stem bark and contributes to the pharmacobotanical study of plant drugs identified as Brazilian quinas, in sequence to two others studies. Compared with the Cinchona species, the prismatic shape of calcium oxalate crystals and the fibers with adornate end walls proved to be the main characteristics for differentiation. <![CDATA[Phenylacylated-flavonoids from <em>Peucedanum chryseum</em>]]> ABSTRACT Phytochemical investigation of the methanol extract of the aerial parts of Peucedanum chryseum (Boiss. &amp; Heldr.) D.F.Chamb., Apiaceae, led to the isolation of a dihydrofuranochromone, cimifugin (1); a phloroacetophenone glucoside, myrciaphenone A (2); and a flavonoid glycoside, afzelin (3) along with two phenylacylated-flavonoid glycosides: rugosaflavonoid C (4), and isoquercitrin 6"-O-p-hydroxybenzoate (5). The structures of compounds 1–5 were elucidated by extensive 1D- and 2D-NMR spectroscopic analysis in combination with MS experiments and comparison with the relevant literature. All compounds are reported for the first time from this species and compounds 2, 4, and 5 from the genus Peucedanum and from Apiaceae. <![CDATA[Nitric oxide inhibitory and anti-<em>Bacillus</em> activity of phenolic compounds and plant extracts from <em>Mesua</em> species]]> ABSTRACT Species from the genus Mesua, Calophyllaceae, are rich source for phenolic compounds such as coumarin xanthone, and benzophenone derivatives. An investigation on the potential biologically active phenolic compounds 1–5 and crude extracts from the stem bark of Mesua hexapetala (Hook. f.) P.S. Ashton and Mesua beccariana (Baill.) Kosterm. for nitric oxide inhibitory activity on RAW 264.7 macrophage as well as anti-Bacillus activity on selected Bacillus were carried out. Hexapetarin (1), which we reported as a new compound isolated from M. hexapetala showed very good nitric oxide inhibitory activity with an IC50 value of 30.79 ± 2.68 µM. This compound also gave very significant activities towards Bacillus subtilis ATCC 6633, Bacillus cereus ATCC 33019, Bacillus megaterium ATCC 14581 and Bacillus pumilus ATCC 14884 in disc diffusion and minimum inhibitory concentrations assay. Moreover, 1,3,7-trihydroxy-2,4-di (3-methyl-2-butenyl)xanthone (2) isolated from M. hexapetala showed very significant nitric oxide inhibitory activity with an IC50 value of 12.41 ± 0.89 µM and does not exhibit anti-Bacillus activity on four types of Bacillus. Meanwhile, compounds 3–5 were inactive in the nitric oxide activity test and anti-Bacillus assay. <![CDATA[Chemical constituents from ethanol extract of <em>Polyalthia rumphii</em> branches and their cytotoxicity evaluation]]> ABSTRACT Twelve known compounds, including eight alkaloids, three lignans and one gossypol derivative, were isolated from the branches of Polyalthia rumphii (Blume ex Hensch.) Merr., Annonaceae. The chemical structures were determined by spectroscopic methods and comparison with literature data. All the isolates were evaluated the cytotoxicity against three human cancer cell lines: Hela, MCF-7 and A549, the results showed that partial of isolates displayed weak cytotoxicities with the IC50 values ranging from 25 to 40 µg/ml. <![CDATA[Antitussive and expectorant properties of growing and fallen leaves of loquat (<em>Eriobotrya japonica</em>)]]> ABSTRACT Folium Eriobotryae, the dried leaves of loquat (Eriobotrya japonica, (Thunb.) Lindl., Rosaceae), is a traditional Chinese medicine used to treat cough with phlegm in China. Fallen and growing loquat leaves were tested for their effect on coughing and expectoration in mice. HPLC-ELSD and HPLC-MS analyses of aqueous and ethanol extracts of fallen or growing leaves were used to identify the chemical components responsible for this effect. Both the aqueous and ethanol extracts of growing and fallen leaves of loquat contained antitussive and expectorant activities. Moreover, an aqueous extract of growing loquat leaves with a higher flavonoid content displayed a stronger expectorant activity while the ethanol extract of fallen loquat leaves that contained a higher content of triterpenoid acids induced a stronger antitussive activity. <![CDATA[An overview of odoriferous marine seaweeds of the <em>Dictyopteris</em> genus: insights into their chemical diversity, biological potential and ecological roles]]> ABSTRACT Since the middle of the twentieth century the marine algae have attracted attention as a source of new drugs. Dictyopteris is an important group of marine seaweeds and is widely distributed in tropical, subtropical and temperate regions. This genus is known by its characteristic “ocean smell”. Some species show a distinct phytochemistry, with specific secondary metabolites, including C11-hydrocarbons, sulfur compounds and quinone derivatives, not usually found in marine seaweeds and described for the first time in the literature. Furthermore, several terpenes, steroids and halogenated compounds have been described. This chemical diversity gives it interesting biological properties, including cytotoxic, antimicrobial, antioxidant, anti-inflammatory and anti-herbivory activities. These findings highlight the importance to continue investigations on this genus and the need to compile the data available so far, since the species are quite heterogeneous, notably in relation to the chemical constitution. This paper reviews the literature on the Dictyopteris genus, focusing on its secondary metabolites and biological activities, in order to build the base for further studies.