Psychotria genus (Rubiaceae) is featured into the angiosperm, being the most speciose genus comprising approximately 1600 species. The available references demonstrate that Psychotria has several uses on traditional medicine including spiritual and cultural purposes, and presents great potential on pharmacological properties, especially the one related to neurodegenerative diseases. Despite its wide biological properties, this genus has shown complex phylogenetic analysis due to lack of chemotaxonomic information. In recent years, the interest in these plants has increased considerably and many active compounds have been isolated. Phytochemical investigations described in the literature confirmed the indole alkaloids as the major compounds and besides that, another particular chemical constituent are cyclic peptides, known as cyclotides. This present review will cover the relevant literature from 1962 until 2015, and outlines the current data on taxonomy, chemotaxonomy, traditional uses, pharmacological properties, chemical composition and ecological approach from Psychotria genus.

A necessidade da introdução de novos agentes quimioterápicos é uma realidade no controle de doenças infecciosas. O Brasil é o país mais rico em biodiversidade, e o Laboratório de Extração da Universidade Paulista tem coletado plantas na Amazônia e Mata Atlântica com a finalidade de identificar extratos vegetais antibacterianos e antitumorais. Estudos prévios demonstraram que a fração etanólica obtida do extrato bruto orgânico do caule de Tabernaemontana angulata Mart. ex Müll. Arg. apresentou atividade antimicrobiana significante contra Staphylococcus aureus ATCC6538, no ensaio de diluição em caldo. Verificou-se por cromatografia em camada delgada que os compostos majoritários presentes na fração ativa eram alcalóides. No presente trabalho, foi obtida a fração de alcalóides totais a partir do extrato bruto, da qual os compostos majoritários foram isolados por sucessivas cromatografias e, posteriormente, identificados por CG-EM e ¹H-RMN como os alcalóides indólicos coronaridina e voacangina. As frações obtidas do isolamento foram testadas no ensaio biológico, porém não demonstraram atividade antimicrobiana.

Introducing new chemotherapeutic agents is a great demand in the control of infectious diseases. Brazil is one of the richest countries in biodiversity and the Laboratório de Extração at UNIP has been collecting plants from the Amazon and Atlantic Rain Forests with the aim of screening for new antibacterial and antitumor plant extracts. Previous studies demonstrated that the ethanol fraction obtained from the crude extract of Tabernaemontana angulata stems showed an antibacterial activity against Staphylococcus aureus (ATCC 6538) in the microdilution broth assay. Two alkaloids were the major compounds in the active fraction, verified by thin layer chromatography analysis. In the present study, the total alkaloids were obtained from the crude extract and were fractionated by preparative thin layer chromatography for the isolation of the main components. The isolated compounds were identified by GC/MS and ¹H-NMR as coronaridine and voacangine. The alkaloid fractions obtained from the isolation procedure were tested for antibacterial activity, but no activity was detected.

Extratos brutos de 17 espécies de plantas coletadas em região de Mata Atlântica no Estado de São Paulo (Brasil) foram avaliadas para as atividades: antifúngica, no reparo do DNA e inibição da acetilcolinesterase. Dos 34 extratos obtidos de folhas e galhos das plantas analisadas para a atividade antifúngica com Cladosporium sphaerospermum e C. cladosporioides, 26,5% foram ativos. Todavia, apenas o extrato das folhas de Cabralea canjerana inibiu fortemente o crescimento dos dois fungos. No ensaio de reparo do DNA com linhagens mutantes de Saccharomyces cerevisiae, 11,7% dos extratos foram ativos, sendo que, 100% destes foram seletivos para o mecanismo de reparo do DNA envolvendo topoisomerase II. Das 17 espécies analisadas, 12 demonstraram atividade anticolinesterásica no ensaio qualitativo sobre cromatografia de camada delgada (CCD). No entanto, apenas os extratos de Tetrastylidium grandifolium (galhos) e Sloanea guianensis (folhas e galhos) apresentaram atividade anticolinesterásica maior que 50% no ensaio quantitativo.

Crude extracts from 17 plant species collected from an Atlantic Forest region in the State of São Paulo (Brazil) have been screened for antifungal, DNA-damaging and acetylcholinesterase inhibiting activities. Of the 34 extracts obtained from leaves and stems of plants assayed for antifungal activity with Cladosporium sphaerospermum and C. cladosporioides 26.5% were active. However, only the extract of leaves of Cabralea canjerana showed a strong inhibition of both fungi. The DNA-damaging assay with mutant strains of Saccharomyces cerevisiae resulted in 11.7 % of the extracts being active whereas 100% of them showed selectivity for the DNA-repair mechanism of topoisomerase II. Of the 17 species analysed, 12 showed anticholinesterasic activity in TLC assay. However, only extracts from Tetrastylidium grandifolium (stems) and Sloanea guianensis (leaves and stems) inhibited acetylcholinesterase activity more than 50% in quantitative assay.

Chromatographic fractionation of the EtOH extract from the leaves of Swartzia langsdorffii afforded the pentacyclic triterpenes oleanolic acid and lupeol, and two saponins: oleanolic acid 3-sophoroside and the new ester 3-O-b-D-(6'-methyl)-glucopyranosyl-28-O-b-D-glucopyranosyl-oleanate. Their structures were elucidated from spectral data, including 2D NMR and HRESIMS experiments. Antifungal activity of all isolated compounds was evaluated, using phytopathogens Cladosporium cladosporioides and C. sphaerospermum, and human pathogens Candida albicans, C. krusei, C. parapsilosis and Cryptococcus neoformans.

Chromatographic fractionation of the organic extract from leaves of Ouratea multiflora afforded the flavone dimers heveaflavone, amentoflavone-7<FONT FACE=Symbol>¢¢</FONT>,4<FONT FACE=Symbol>¢¢¢</FONT>-dimethyl eter, podocarpusflavone-A and amentoflavone. Their structures were elucidated from spectral data, including 2D-NMR experiments of the natural substances. Biological activities of all isolates were evaluated, using antimicrobial assay against Gram-positive bacteria Staphylococcus aureus and Bacillus subtilis, cytotoxicity assay against mouse lymphoma (L5178) and KB cell lines, TLC screening for acetylcholinesterase inhibitors and antioxidant activity measured by DPPH test.

O fracionamento cromatográfico do extrato orgânico das folhas de Ouratea multiflora forneceu os flavonóides diméricos, heveaflavona, 7<FONT FACE=Symbol>¢¢</FONT>,4<FONT FACE=Symbol>¢¢¢</FONT>-dimetilamentoflavona, podocarpusflavona-A e amentoflavona. Suas estruturas foram elucidadas com base nos dados espectrais, incluindo experimentos bidimensionais de RMN, das substâncias naturais. A atividade antibiótica de todos os isolados foi avaliada, usando-se as bacterias Gram-positivas Staphylococcus aureus and Bacillus subtilis. Teste de citotoxicidade nas linhagens de linfoma de ratos (L5178) e KB também foram conduzidos para avaliar os extratos e os flavonóides isolados. a triagem biológica para a avaliação de atividade antioxidante e inibidora de acetil colinesterase foram conduzidas pela técnica da bioautografia com DPPH e teste pelo teste de Ellman respectivamente.

Phytochemical studies with leaves of Uncaria guianensis resulted in the isolation of the oxindole alkaloids isomitraphylline (1), 3-isoajmalicine (2) mitraphylline (3), and isomitraphylinic acid (4). Structural assignments of these alkaloids, including relative configurations and conformations, were performed through spectral data and physical properties. 1D and 2D homonuclear and heteronuclear NMR spectroscopy was a valuable tool for the establishment of the relative stereochemistry of those compounds.

The bioactive compound trans-3'-methylsulphonylallyl trans-cinnamate (1) along with the inactives iryelliptin (2) and (7R,8S,1'S)-delta8'-3',5'-dimethoxy-1',4'-dihydro-4'-oxo-7.0.2',8.1'-neolignan (3) were isolated from the leaves of Cinnamomum australe. The structures of these compounds were assigned by analysis of 1D and 2D NMR data and comparison with data registered in the literature for these compounds. The DNA-damaging activity of 1 is being described for the first time.

(Triagem de plantas nativas do Brasil para atividades antimicrobiana e de Danos no DNA I. Mata Atlântica . Estação Ecológica Juréia-Itatins). Oitenta e oito espécies nativas do estado de São Paulo foram coletadas numa região de Mata Atlântica e ensaiadas quanto a sua atividade antimicrobiana e capacidade de causar danos no DNA. Dos 114 extratos submetidos aos ensaios para atividade antibacteriana, apenas os extratos de folhas e galhos de Aspidosperma ramiflorum (Apocynaceae) apresentaram uma atividade fraca contra Escherichia coli. No ensaio antifúngico com Candida albicans, não foram observados extratos ativos. Por outro lado, no ensaio de bioautografia com Cladosporium sphaerospermum e C. cladosporioides 12% dos extratos apresentaram atividade. Contudo, nesse ensaio, somente o extrato dos ramos de Psychotria mapoureoides (Rubiaceae) inibiu fortemente o crescimento de ambas espécies do fungo. O ensaio para danos no DNA com cepas mutantes de Saccharomyces cerevisiae apresentou 17.5 % de extratos ativos. A maioria dos extratos ativos (55 %) apresentou resultados seletivos para danos dependentes da topoisomerase II como mecanismo de reparo do DNA e somente 20 % foram seletivos para o mecanismo da topoisomerase I.

I. Atlantic Rain Forest . Ecological Station Juréia-Itatins) Crude extracts from 88 plant species occurring in São Paulo State (Brazil), collected in an Atlantic Forest region, have been screened for antimicrobial and DNA-damaging activities. Of the 114 extracts assayed for antibacterial activity, only the extracts from leaves and stems of Aspidosperma ramiflorum (Apocynaceae) showed a slight activity against Escherichia coli. In the antifungal assay with Candida albicans, no active extract was observed, while in the bioautography assay with Cladosporium sphaerospermum and C. cladosporioides 12% were active. However, only the extract of Psychotria mapoureoides (Rubiaceae) stems showed a strong inhibition of both fungi. The DNA-damaging assay with mutant strains of Saccharomyces cerevisiae resulted in 17.5 % of active extracts. The majority (55 %) of the active extracts showed selectivity for the DNA-repair mechanism of topoisomerase II and only 20 % showed a selective response for the mechanism of topoisomerase I.

Chemical investigation of Arrabidaea samydoides resulted in the isolation of the flavone chrysin; five triterpenes: lupeol, ursolic acid, 3b,16a-dihydroxy-urs-12-ene, uvaol, and erythrodiol; and two sterols: sitosterol and stigmasterol. The structures of these compounds were established by spectroscopic analysis. This paper deal with the first phytochemical study of Arrabidaea samydoides.

The bioassay-guided fractionation of stems from Kielmeyera variabilis, traditionally used in Brazilian folk medicine, yielded assiguxanthone-B (1), kielcorin (4), 2,5-dihydroxybenzoic acid (3), and a mixture of xanthones containing assiguxanthone-B (1) and 1,3,5,6-tetrahydroxy-2-prenylxanthone (2) (1:1 w/w). The xanthone mixture inhibited Staphylococcus aureus and Bacillus subtilis at a concentration of 6.25 µg/ml. When tested alone, the minimal inhibitory concentration of assiguxanthone-B was 25 µg/ml against B. subtilis. Kielcorin and 2,5-dihydroxybenzoic acid were inactive against both strains. None of the fractions was active against Escherichia coli or Pseudomonas aeruginosa. Viable cells of S. aureus were reduced by a 1-3 log CFU/ml within 12 h after exposure of one to eight times the MIC of the xanthone mixture. It is not known whether the tetrahydroxy-2-prenylxanthone or other components of the xanthone mixture are responsible for the main antibacterial activity or whether additive or synergistic action is involved

Chemical investigation of the leaves of Styrax camporum (Styracaceae) resulted in the isolation of the lignan lariciresinol and six triterpenes: ursolic acid, 2alpha,3alpha-dihydroxy-urs-12-en-28-oic acid and mixtures of uvaol and erythrodiol, as well as 3beta-O-trans-p-coumaroyl-2alpha-hydroxy-urs-12-en-28-oic acid and 3b-O-trans-p-coumaroylmaslinic acid. The structures of these compounds were established by spectroscopic analysis. This paper deals with the first report of these compounds in S. camporum.