Abstract Trembleya parviflora (D. Don) Cogn., Melastomataceae, also known as "quaresmeira-branca", is a subshrub that is commonly used to treat verminosis, scabies, dermatoses, rheumatism, vaginal infections, ulcerations and wounds. The aim of this work was to perform a morphological study of T. parviflora, evaluate the composition and chemical variability of the volatile oils from the leaves, perform phytochemical screening of the powder from the leaves and to define parameters for quality control of the plant material. Macroscopic characterization of T. parviflora was carried out by naked eye in Serra dos Pireneus, Pirenópolis, Goiás for 12 months. Volatile oils were subjected to hydrodistillation with Clevenger apparatus and analyzed by gas chromatography-mass spectrometry. Phytochemical screening and ash and volatile compound content determination were performed by conventional techniques. T. parviflora has simple, oppositely crossed and petiolate leaves. The inflorescence of this plant is a cyme. The presence of coumarins, steroids, triterpenes, flavonoids and tannins was observed. The total ash content was 4.05 ± 0.02%; the insoluble ash content was 0.10 ± 0.03%; and the volatile compound content was 9.53 ± 0.02%. The major compounds present in the volatile oils were α-terpineol (2.7–16.5%), α-pinene (0.6–25.4%), β-pinene (2.7–23.1%), sabinene (1.2–14.1%), acetoxyeudesman-4-α-ol (0.6–6.3%) and 2,4a-8,8-tetramethyldecahydrocyclopropanaphtalene (2.4–24.4). Two clusters were identified: Cluster I represented the period with low levels of rainfall, and Cluster II represented the period with high levels of rainfall. This study provides data that can be applied for the quality control of powdered leaves and is the first description of the chemical composition and variability of the volatile oils from the leaves of T. parviflora.

ABSTRACT Trembleya phlogiformis DC., Melastomataceae, is a shrub whose leaves are used as a dye for dyeing wool and cotton. The present article aimed to carry out the morphological description of the species, to study the chemical composition of volatile oils from the leaves and flowers and the seasonal variability from the leaves during a year. Macroscopic characterization was carried out with the naked eye and with a stereoscopic microscope. Volatile oils were isolated by hydrodistillation in Clevenger apparatus and analyzed by gas chromatography/mass spectrometry. The major components of the volatile oil of T. phlogiformis flowers were: n-heneicosane (33.5%), phytol (12.3%), n-tricosane (8.4%) and linoleic acid (6.1%). It was verified the existence of a large chemical variability of the volatile oils from the leaves of T. phlogiformis over the months, with the majority compound (oleic alcohol, ranging from 5.7 to 26.8%) present in all samples. A combination of Cluster Analysis and Principal Component Analysis showed the existence of three main clusters, probably related to the seasons. The results suggested that the volatile oils of T. phlogiformis leaves possess high chemical variability, probably related to variation associated with rainfall and the variation in the behavior of specimens throughout the year. This research provides insights for future studies on the volatile oils obtained from the T. phlogiformis leaves and flowers, mainly related to biological markers of applications monitored in the leaves and flowers of this species.

ABSTRACT Hyptis carpinifolia Benth., Lamiaceae, is a species known popularly as "rosmaninho" and "mata-pasto", and leaves are employed in Brazilian folk medicine to treat colds, flu, and rheumatism. The aim of this study was to perform a morphological description of H. carpinifolia and to evaluate the seasonal chemical variability of the leaf essential oils during 12 months. Macroscopic characterization of H. carpinifolia was carried out with the naked eye and with a stereoscopic microscope. Essential oils were isolated from leaves by hydrodistillation in Clevenger apparatus and analyzed by gas chromatography/mass spectrometry. Major compounds were found to be 1,8-cineole (39.6-61.8%), trans-cadina-1(6),4-diene (2.8-17.5%), β-caryophyllene (4.4-10.0%), prenopsan-8-ol (4.2-9.6%) and β-pinene (2.9-5.3%). Results of essential oils compositions were processed by cluster analysis and principal component analysis. Data showed high variability in the concentration of the components. Besides, there was a seasonal variability of chemical composition, probably related mainly to the rainfall regime.

Abstract Hortia oreadica Groppo, Kallunki & Pirani, Rutaceae, known as “para-tudo”, “quina”, and “quina-do-campo”, is used in traditional medicine locally to treat stomach pain and fevers. The aims of this study were: analyze the chemical composition of essential oils from leaves, flowers and fruits of H. oreadica and verify the seasonal variation of the chemical components of essential oils from leaves. The essential oils were obtained by hydrodistillation using a Clevenger type apparatus and analyzed by GC/MS. The major components found in the samples of the essential oils were the amorpha-4,7(11)-diene (29.27% – flowers, 20.26% – fruits, 27.66–37.89% – leaves), bicyclogermacrene (23.28% – flowers, 20.64% – fruits, 14.71% to 31.37% – leaves). This work represents the first study of the chemical composition of essential oils from leaves, flowers and fruits and seasonal variation in the essential oils from leaves of H. oreadica.

Os óleos essenciais de quatro espécies de Marsypianthes (Lamiaceae) foram investigados por meio de cromatografia gasosa e análise multivariada. Cada espécie foi representada por duas a sete populações, totalizando dezessete populações. β-Elemeno, (E)-cariofileno, α-humuleno, germacreno D, biciclogermacreno, δ-cadineno, espatulenol, óxido de cariofileno e globulol ocorreram em todas as amostras. As análises de componentes principais e de agrupamento hierárquico evidenciaram a presença de duas seções, uma contendo M. chamaedrys/M. montana (seção A) e a outra contendo M. burchellii (seção B). M. foliolosa apresentou maior complexidade, dividindo-se nas duas seções. Resultados similares foram obtidos de acordo com os esqueletos carbônicos biosssintéticos. Germacranos e biciclogermacranos preponderaram na seção A, enquanto aromadendranos e guaianos caracterizaram a seção B. A análise de redundância canônica mostrou que os agrupamentos não foram influenciados por variáveis edáficas dos locais de amostragem.

Essential oils of four species of Marsypianthes (Lamiaceae) were investigated via gas chromatography and multivariate analysis. Each species was represented by two to seven populations, totaling seventeen populations. β-Elemene, (E)-caryophyllene, α-humulene, germacrene D, bicyclogermacrene, δ-cadinene, spathulenol, caryophyllene oxide, and globulol were found in all samples. Principal component and hierarchical cluster analyses revealed the presence of two sections, one containing M. chamaedrys/M. montana (section A) and the other M. burchellii (section B). M. foliolosa showed higher complexity, being divided in both sections. Similar results were obtained according to biosynthetic carbon skeletons. Germacranes and bicyclogermacranes predominated in section A, whereas aromadendranes, bourbonanes and guaianes characterized section B. Canonical redundancy analysis revealed that clusters were not influenced by edaphic factors in sampling sites.

O Cerrado Central brasileiro é considerado o centro de origem e dispersão de Hypenia (Lamiaceae: subtribo Hyptidineae) na América do Sul. O gênero tem sido mantido sem divisão, ou subdividido em duas ou cinco seções taxonômicas, baseadas quase exclusivamente a partir de um conjunto limitado de características florais. Neste trabalho, uma delimitação química interespecífica é descrita a fim de complementar as análises das características botânicas. Análise multivariada dos óleos essenciais de dez espécies na fase vegetativa suporta a divisão taxonômica do gênero em duas seções. Grupo I incluiu quatro espécies da seção Laxiflorae em adição à H. irregularis, os quais foram caracterizados pelos mais altos percentuais de espatulenol e óxido de cariofileno. Grupo II conteve cinco espécies da seção Densiflorae com α-cadinol, a-muuroleno e a-muurolol como constituintes principais. Cadinanos e germacranos/aromadendranos parecem ser as classes marcadoras quimiotaxonômicas nas seções Densiflorae e Laxiflorae, respectivamente.Além disso, análise de redundância canônica não indicou correlação significante entre fatores edáficos com quimiovariação nos óleos essenciais, sugerindo que em Hypenia os óleos são constituídos por substâncias constitutivas e não induzidas pelo ambiente.

Central Brazilian Cerrado is regarded as the center of origin and dispersion of Hypenia (Lamiaceae: subtribe Hyptidineae) in South America. The genus has either remained undivided or been divided into two or seven taxonomic sections, based almost exclusively on a limited range of floral features. Interspecific chemical delimitation to complement analyses of botanical traits is described. Multivariate analysis of essential oils of ten species in the vegetative stage supports the taxonomic division in two sections. Cluster I included four species belonging to section Laxiflorae in addition to H. irregularis, which were characterized by the highest percentages of spathulenol and caryophyllene oxide. Cluster II contained five species belonging to section Densiflorae with α-cadinol, α-muurolene and a-muurolol as major constituents. Cadinanes and germacranes/ aromadendranes seem to be chemotaxonomic markers of sections Densiflorae and Laxiflorae, respectively. Furthermore, redundancy analysis revealed no significant correlation between edaphic factors and oil chemovariations, suggesting that Hypenia oils consist of constitutive rather than induced compounds.

A análise multivariada da composição química dos óleos essenciais de treze espécies de Hypenia indicou a presença de dois grupos de óleos em relação às seções botânicas das amostras. O primeiro grupo (grupo I) incluiu as três espécies da seção Densiflorae em adição a H. subrosea e H. aristulata, o qual foi caracterizado pelo maior percentual de α-muurolol (5,85 ± 3,08%). No grupo II, com oito espécies da seção Laxiflorae, os principais constituintes discriminantes foram o (E)-cariofileno (7,09 ± 4,88%), germacreno D (18,1 ± 11,4%) e o biciclogermacreno (6,65 ± 1,19%). Todos os óleos essenciais apresentaram predominantemente sesquiterpenos, tais como espatulenol (4,5-31,6%), óxido de cariofileno (2,2-14,4%) e selin-11-en-4α-ol (0-34,8%). Os agrupamentos foram idênticos quando utilizada a análise multivariada baseada nos esqueletos carbônicos dos constituintes químicos ou de 18 caracteres morfológicos das folhas das espécies

Multivariate analysis of essential oil compositions of thirteen Hypenia species revealed the presence of two taxonomic clusters. Cluster I included three species belonging to section Densiflorae in addition to H. subrosea and H. aristulata, and showed the highest percentages of α-muurolol (5.85 ± 3.08%). In Cluster II, which contained eight species belonging to section Laxiflorae, the major discriminant constituents were (E)-caryophyllene (7.09 ± 4.88%), germacrene D (18.1 ± 11.4%), and bicyclogermacrene (6.65 ± 1.19%). All essential oils showed a predominance of sesquiterpenes, such as spathulenol (4.5-31.6%), caryophyllene oxide (2.2-14.4%) and selin-11-en-4α-ol (0-34.8%). Furthermore, identical clusters were revealed by multivariate analysis of chemical constituents based on carbon skeletons, as well as on 18 morphological leaf characters of the species studied

Memora nodosa (Silva Manso) Miers, Bignoniaceae, é uma planta do Cerrado utilizada popularmente como cicatrizante de úlceras e feridas externas (folhas e caules). O objetivo deste trabalho foi caracterizar morfologicamente essa espécie e fazer o estudo anatômico de suas folhas. O estudo morfológico foi realizado à vista desarmada e com o auxílio de microscópio estereoscópico. Para o estudo anatômico as folhas foram seccionadas e as lâminas histológicas confeccionadas de acordo com as técnicas convencionais. Memora nodosa é um arbusto com folhas opostas cruzadas, recompostas, bipinadas, imparipinadas, com foliólulos pequenos, lanceolados, verde-escuros e brilhantes. A inflorescência é racemosa com flores infundibuliformes e corola amarelo-ouro; glândulas nectaríferas são observadas no terço superior do cálice; androceu com quatro estames férteis, didínamos e um estaminódio reduzido; gineceu com estilete terminal, ovário súpero, assentado sobre um disco nectarífero. O fruto é do tipo cápsula septífraga achatada, com sementes aladas. Anatomicamente a lâmina do foliólulo é hipoestomática com estômatos predominantemente paracíticos. O parênquima paliçádico é pluriestratificado, ocupando cerca de dois terços do mesofilo dorsiventral. Tricomas glandulares e tectores são observados, em maior número, nas folhas jovens.

Memora nodosa (Silva Manso) Miers, Bignoniaceae, is a Brazilian Savannah plant, popularly used as external wound and ulcer healing (leaves and stems). The goal of this research was to perform the morphological study of M. nodosa species and the anatomical study of its leaves. The morphological study was done to the naked eye and with the aid of a stereoscopic microscope. For the anatomical study leaves were sectioned and histological slides made in accordance with conventional techniques. Memora nodosa is a shrub with decussate leaves recomposed, bipinnate, imparipinnate with small leaflets, lanceolate, dark green and shining. The inflorescence is racemose with infundibuliform flowers and gold yellow corolla; nectar glands are observed in the upper third calyx; androecium with four fertile stamens, didynamus and one staminode; gynoecium with terminal style, superior ovary, seated on a nectary disc. The fruit is flattened septifragal capsule with winged seeds. Anatomically, the blade leaflet is hypostomatic with predominantly paracytic stomata. The palisade parenchyma is pluriseriate, occupying about two thirds of the dorsiventral mesophyll. Glandular and non-glandular trichomes are observed in greater numbers in the young leaves.

A atividade antioxidante, avaliada pelo método DPPH (1,1-difenil-2-picrilidrazila), e o teor em compostos fenólicos totais do extrato bruto metanólico e frações das folhas da espécie Palicourea rigida Kunth, Rubiaceae, foram quantificadas neste trabalho. Apesar da baixa atividade apresentada pelo extrato bruto (500 ppm), a fração acetato de etila apresentou atividade moderada (192 ppm) e o maior teor de fenólicos totais dentre as frações ensaiadas. Assim, a fração acetato de etila foi submetida a procedimentos cromatográficos o que resultou no isolamento dos flavonoides quercetina 3-O-β-D-glicosídeo, quercetina 3-O-soforosídeo e isoraminetina 3-glicosídeo, cujas estruturas foram elucidadas por análise espectroscópica, incluindo RMN (1D e 2D) e comparação com os dados da literatura.

The antioxidant activity, evaluated by DPPH (1,1-difenil-2-picrilidrazila) method, and the determination of the total phenolic compounds of the crude methanolic extract and fractions of the Palicourea rigida Kunth, Rubiaceae, leaves were quantified in this work. Despite weak activity exhibited by crude extract (500 ppm), the fraction ethyl acetate showed moderate activity (192 ppm), and the largest value for the phenolic compounds among all the assayed fractions. Then, the ethyl acetate fraction was submitted to the chromatography procedures which led to the isolation of the flavonoid quercetin 3-O-D-glicoside, quercetin 3-O-sophoroside and isorhamnetin 3-glicoside, which had the structures elucidated by spectroscopy analysis, including RMN (1D and 2D) and comparison with literature data.

Hyptidendron canum (Pohl ex Benth.) Harley, Lamiaceae, é utilizada popularmente como antimalárica, antiinflamatória, antiulcerativa, anti-hepatotóxica e anticancerígena. O objetivo deste trabalho foi realizar o estudo morfo-anatômico das folhas e caules e identificar as principais classes de metabólitos secundários presentes nas folhas de H. canum, dados ainda não descritos na literatura. As folhas e caules jovens coletados em Goiânia (GO) foram seccionados à mão livre e preparados para análise microscópica. Foram realizadas reações de identificação de metabólitos secundários do material dessecado e pulverizado. Preparou-se o extrato etanólico bruto, que posteriormente foi fracionado por partição líquido-líquido com hexano, clorofórmio e acetato de etila. As frações foram submetidas à análise cromatográfica em camada delgada (CCD). As lâminas foliares apresentam epiderme adaxial constituída por células poligonais com parede reta. Na epiderme abaxial observam-se células com parede reta a ondulada e estômatos diacíticos e anisocíticos. Tricomas tectores e glandulares estão presente em ambas as faces da lâmina foliar. O pecíolo apresenta aspecto canaletado, epiderme adaxial e abaxial unisseriada. O caule, em secção transversal possui contorno em geral quadrangular, com presença de tricomas tectores e glandulares. As reações e a CCD das folhas evidenciaram a presença de flavonóides, saponinas, terpenos e lignanas. Este trabalho contribuiu para um maior conhecimento da morfo-anatomia e das classes químicas presentes em H. canum.

Hyptidendron canum(Pohl ex Benth.) Harley, Lamiaceae, is popularly used as an antimalarial, anti-inflammatory, antiulcerative, antihepatotoxic and anticancer agent. The goal of this research was to perform the morphoanatomy study of H. canumleaves and stem and identify the main classes of secondary metabolites present in the of H. canumleaves. Such data have not been reported in the literature. The young leaves and stems were collected in Goiânia (GO), hand sectioned and prepared for microscope analysis. Reactions were performed for the identification of secondary metabolites of the dried and pulverized material. The crude ethanol extract was prepared and then fractioned by liquid-liquid partition with hexane, chloroform and ethyl acetate. Thin layer chromatography (TLC) analysis was performed on the fractions. The leaf blades presented adaxial epidermis constituted of polygonal cells with straight walls. On the abaxial epidermis cells with straight to wavy walls and diacytic and anisocytic stomates were noted. Non-glandular and glandular trichomes are present on both faces of the leaf blade. The petiole is grooved, and it presents single layered adaxial and abaxial epidermis. The cross section of the stem presents a generally quadrangular contour with the presence of non-glandular and glandular trichomes. The leaf reactions and TLC evidenced the presence of flavonoids, saponins, terpenes and lignanes. This works helps to increase knowledge of the morphoanatomy and the chemical classes present in H. canum.

O intuito deste trabalho de pesquisa foi obter parâmetros de controle de qualidade para a identificação da matéria-prima vegetal (folha) de Pimenta pseudocaryophyllus (Gomes) L. R. Landrum - Myrtaceae que ocorre no cerrado brasileiro. Para tanto foram coletadas amostras em Minas Gerais - Brasil e no Distrito Federal - Brasil e as exsicatas foram depositadas no Herbário da UFG n. UFG-27.159 e no Herbário Ezechias Paulo Heringer n. 21.745-0, respectivamente. Parte desse material botânico foi preparada para análises macro e microscópicas. Outra parte foi seca, triturada e usada para a triagem fitoquímica. O estudo mostrou que as folhas de P. pseudocaryophyllus são hipoestomáticas, têm grande quantidade de tricomas unicelulares na superfície abaxial, têm cavidades secretoras contendo compostos lipídicos e as células epidérmicas possuem paredes celulares espessas. Na triagem fitoquímica foram detectados compostos fenólicos, taninos e flavonóides. Os taninos foram dosados por diferentes métodos envolvendo reações colorimétricas e de precipitação com proteínas. Os diferentes resultados verificados chamam a atenção para a necessidade de se especificar o método utilizado juntamente com o limite mínimo de taninos totais estabelecido. Os resultados obtidos configuram-se como importantes parâmetros para o controle de qualidade da matéria-prima vegetal e denotam que a espécie em estudo possui um importante potencial fitoterápico que merece ser investigado em estudos farmacológicos e toxicológicos.

The goal of this research was to obtain quality control parameters for the identification of the plant drug of Pimenta pseudocaryophyllus (Gomes) L. R. Landrum that occurs in Brazilian savannah. So, two samples were collected, one in Minas Gerais state - Brazil, and the other one in Brasilia city - DF - Brazil, and the vouchers were deposited in the UFG Herbarium code number UFG-27159 and Ezechias Paulo Heringer Herbarium code number 21745-0, respectively. Part of the botanical material in both samples was prepared for microscopic analysis. The other one was air-dried, crushed to powder and used for phytochemical screening. The study has shown that P. pseudocaryophyllus leaves are hypostomatic, there are abundant unicellular trichomes in abaxial surface, there are secretory cavities with oily content and epidermal cells have thick wall. Tannins, phenolic compounds and flavonoids were detected in the phytochemical screening. The tannins had been quantified by different methods involving colorimetric and protein precipitation reactions, getting different results. This fact calls the attention for the necessity of specifying the method used together with the minimum tannins limit established. The results configure as important parameters for the quality control of the plant material and denote that the species in study take an important potential as herbal medicine that it deserves to be investigated in pharmacologic and toxicologic studies.

A composição de taninos em cascas de espécies de barbatimão, Stryphnodendron adstringens (Mart.) Cov. and S. polyphyllum (Mart.), foi analisada mensalmente durante um ano. Os resultados foram correlacionados com as condições climáticas do período de coleta (precipitação, umidade e temperatura média) através de métodos quimiométricos. Análise de componentes principais dos dados mostrou uma tendência de maior produção de taninos na estação quente e chuvosa, sugerindo que os fatores ambientais podem afetar os teores de taninos nestas espécies.

The contents of tannins in the barks of barbatimão species, Stryphnodendron adstringens (Mart.) Cov. and S. polyphyllum (Mart.), were analysed monthly during one year. Results were correlated with climate conditions (rainfall, humidity and mean temperature) by chemometric methods. Principal component analysis of the data showed a tendency for higher production of tannins in the warm and wet season, suggesting that environmental factors can affect the levels of tannins in those plants.

As folhas de Hyptis ovalifolia Benth. (Lamiaceae) foram submetidas à hidrodestilação e a fração volátil foi investigada por CG/EM. O componente principal, (R)-6-[(Z)-1-heptenila]-5,6-diidro-2H-piranona (1), representando 60% do óleo essencial, foi isolado por cromatografia em coluna e identificado por métodos espectroscópicos. O composto mostrou atividade in vitro contra 4 espécies (60 isolados clínicos) dos dermatófitos: Microsporum canis, Microsporum gypseum, Tricophyton mentagrophytes e Tricophyton rubrum com concentração inibitória mínima variando de 125-7,8 µg mL-1.

The leaves of Hyptis ovalifolia Benth. (Lamiaceae) were subjected to hydrodistillation and the resulting volatiles were investigated by GC/MS. The main constituent representing 60% of the essential oil was isolated by column chromatography and identified by spectroscopic methods as (R)-6-[(Z)-1-heptenyl]-5,6-dihydro-2H-pyran-2-one (1). This compound showed strong in vitro activity against four dermatophyte fungi Microsporum canis, Microsporum gypseum, Tricophyton mentagrophytes, and Tricophyton rubrum (a total of 60 strains) with a minimal inhibitory concentration observed in the range of 125-7.8 mg µL-1.