The genus Trichilia, belonging to the Meliaceae family, comprises ca. 102 species, some of which have been the subject of phytochemical studies. Compounds of different classes with cytotoxic, antimicrobial, and antioxidant activities were isolated from Thichilia. Trichilia pseudostipularis, a native species, is distributed along the entire Brazilian coast, from southern Santa Catarina to Bahia. Due to the inexistence of previous chemical studies, their wood and roots were investigated. Compounds 3,4-dihydro-4-isopropyl-6-methylnaphthalen-1(2H)-one (1), 3,4-dihydro-7-hydroxy-4-isopropyl-6-methylnaphthalen-1(2H)-one (2), and pseudostipulariol (3) were isolated from wood, while the lactone derivate rel-(2S,3S,4R)-3-hydroxy-4-methyl-2-(13”-phenyl-l’-n-tridecyl)-butanolide (4) was isolated from the roots. Compounds 3 and 4 are reported for the first time. family ca 10 species studies cytotoxic antimicrobial Thichilia pseudostipularis coast Bahia investigated 3,4dihydro4isopropyl6methylnaphthalen12Hone 34dihydro4isopropyl6methylnaphthalen12Hone dihydroisopropylmethylnaphthalenHone 3,4 dihydro isopropyl 6 methylnaphthalen 1 2H one H 1, , (1) 3,4dihydro7hydroxy4isopropyl6methylnaphthalen12Hone 34dihydro7hydroxy4isopropyl6methylnaphthalen12Hone dihydrohydroxyisopropylmethylnaphthalenHone 7 hydroxy 2, 2 (2) (3 rel2S,3S,4R3hydroxy4methyl213phenyllntridecylbutanolide rel2S3S4R3hydroxy4methyl213phenyllntridecylbutanolide relSSRhydroxymethylphenyllntridecylbutanolide rel 2S,3S,4R methyl 13 phenyl l n tridecyl butanolide 2S 3S 4R S R (4 time 4dihydro4isopropyl6methylnaphthalen12Hone Hone 34 3, (1 4dihydro7hydroxy4isopropyl6methylnaphthalen12Hone (2 ( rel2S 4R3hydroxy4methyl213phenyllntridecylbutanolide phenyllntridecylbutanolide 2S3S4R SSR relS Rhydroxymethylphenyllntridecylbutanolide

The need to increase the product’s shelf life and the growing concern to minimize the use of synthetic products encouraged the researchers to evaluate the antioxidant activity and quantify phenolic compounds as chlorogenic acid, caffeic acid, rutin, quercetin and apigenin through the use of HPLC, in 29 accesses of Capsicum baccatum. Capsicum baccatum var. pendulum is one species of the Capsicum genus widely consumed in Brazil. It is the second largest pepper produced in the world. However, its chemical composition and mainly its extract antioxidant activity have been poorly reported in literature. In order to deepen the study of the access properties relating the antioxidant activity versus content of phenolic compounds. It is suggested that the BRS, 1643a, 1611 and 1613, accession could be used as natural antioxidants in the food industry.

The first Simira sampaioana (Rubiaceae) phytochemical study allowed the isolation and structural determination of a new erythroxylane diterpene named Angelocunhol, 11β,12α-dihydroxy-2,4(18),15-eritroxilatrien-1-one, together with 14 known compounds: simirane B, harman, maxonine, isomalindine, malindine, sitost-4-en-6-ol-3-one, estigmast-4,22-dien-6-ol-3-one, campest-4-en-6-ol-3-one, sitost-4-en-3-one, stigmast-4,22-dien-3-one, campest-4-en-3-one, β-sitosterol, stigmasterol, and stigmast-4,22-dien-3-ol from the wood of a specimen of the species. The structures of these compounds were elucidated on the spectroscopic-data analysis basis, mainly 1H and 13C nuclear magnetic resonance (NMR), including 2D experiments (1H-1H correlation spectroscopy (COSY), nuclear Overhauser spectroscopy (NOESY), heteronuclear multiple-bond correlation-HMBC and heteronuclear single-quantum correlation-HSQC), and high-resolution electrospray mass spectrometry (HRESI-MS).

O presente trabalho descreve o isolamento e a identificação de nove alcaloides indólicos monoterpênicos das cascas das raízes e folhas de Tabernaemontana salzmannii (Apocynaceae). As estruturas dos alcaloides foram identificadas através de métodos espectroscópicos uni (RMN ¹H, 13C, APT) e bidimensionais (¹H-¹H-COSY, ¹H-¹H-NOESY, HMQC e HMBC) e espectrometria de massas (EM), além da comparação com dados de literatura. Um screening in vitro da atividade antileucêmica foi feito com os alcaloides majoritários isolados. Dentre os nove alcaloides isolados, a isovoacangina e voacangina mostraram-se capazes de induzir morte celular por apoptose em células leucêmicas humanas THP-1.

This work describes the isolation and structural determination of nine monoterpenic indole alkaloids from the roots bark and leaves of Tabernaemontana salzmannii. The alkaloids were identified by spectroscopic methods uni (NMR ¹H, 13C, APT) and two-dimensional (¹H-¹H-COSY, ¹H-¹H-NOESY, HMQC and HMBC) and mass spectra besides comparison with literature data. An in vitro screening was done with the isolated major alkaloids. Among the nine alkaloids isolated, isovoacangine and voacangine alkaloids were able to induce apoptosis cell death in human leukemic cells line THP-1.

O presente trabalho descreve o isolamento e a identificação de nove alcaloides indólicos monoterpênicos das cascas das raízes e folhas de Tabernaemontana salzmannii (Apocynaceae). As estruturas dos alcaloides foram identificadas através de métodos espectroscópicos uni (RMN ¹H, 13C, APT) e bidimensionais (¹H-¹H-COSY, ¹H-¹H-NOESY, HMQC e HMBC) e espectrometria de massas (EM), além da comparação com dados de literatura. Um screening in vitro da atividade antileucêmica foi feito com os alcaloides majoritários isolados. Dentre os nove alcaloides isolados, a isovoacangina e voacangina mostraram-se capazes de induzir morte celular por apoptose em células leucêmicas humanas THP-1.

This work describes the isolation and structural determination of nine monoterpenic indole alkaloids from the root barks and leaves of Tabernaemontana salzmannii. The alkaloids were identified by spectroscopic methods uni (NMR ¹H, 13C, APT) and two-dimensional (¹H-¹H-COSY, ¹H-¹H-NOESY, HMQC and HMBC) and mass spectra besides comparison with literature data. An in vitro screening was done with the isolated major alkaloids. Among the nine alkaloids isolated, isovoacangine and voacangine alkaloids were able to induce apoptosis cell death in human leukemic cells line THP-1.

The aroma and fragrance industry is a billion-dollar world market which grows annually. Essential oils comprise the majority of compounds used by these industries. These sets of metabolites are formed mainly by monoterpenes, which are products of the plants' secondary metabolism. Biosynthesized from mevalonate and methylerythitol phosphate, the essential oil production depends not only on genetic factors and the developmental stage of plants, but also on environmental factors which could result in biochemical and physiological alterations in plants modifying the quantity and quality of the essential oil. These modifications impair aromatic plant production aimed at essential oil by reducing their quality. It is desirable to develop techniques of agronomical management to improve essential oil products and their specific compounds. Among other factors influencing essential oil production are plant growth regulators or plant hormones. Endogenous levels as well exogenous application could affect essential oil production and chemical composition. In this review we will present research in which plant growth regulators or their synthetic analogs were used and their effects on essential oil production.

Os extratos obtidos de folhas e caule de Paullinia weinmmaniaefolia foram testados contra larvas de Artemia salina e mostraram significante letalidade. Os extratos das folhas em diclorometano e do caule em metanol e metanol-água (8:2) apresentaram atividade com valores de CL50 366,87; 375,38 e 620,30 ppm, respectivamente. Sete triterpenos, dois esteróides e um ciclitol foram identificados através de técnicas espectrométricas como principais constituintes destes extratos.

The extracts obtained from leaves and steam of Paullinia weinmmaniaefolia were tested against Artemia salina larvae and showed significant lethality. The extracts in dichloromethane of the leaves, in methanol and methanol-water (8:2) of the steam showed activity with LC50 values of 366.87, 375.38 and 620.30 ppm, respectively. Seven triterpenes, two steroids and one cyclitol were characterized by spectrometric methods with majoritary constituents of these extracts.

A investigação fitoquímica do extrato metanólico das folhas de Annona dioica (Annonaceae) resultou na identificação dos flavonóides kaempferol (1), 3-O-[3",6"-di-O-p-hidroxicinamoil] -beta-galactopiranosil-kaempferol (2), 6"-O-p-hidroxicinamoil-beta-galactopiranosil-kaempferol (3) e 3-O-beta-galactopiranosil-kaempferol (4). As estruturas foram caracterizadas inequivocamente através de análises espectroscópicas utilizando-se RMN de ¹H e 13C uni e bi-dimensional. Os efeitos citotóxicos dos flavonóides e da fração flavonoídica (FF) foram avaliados frente a células do carcinoma de Ehrlich, utilizando-se o ensaio do MTT (brometo de 3-(4,5-dimetiltiazol-2-il)-2,5-difeniltetrazolium). Os resultados indicaram que 1, 2, 3 e FF apresentam ação anti-proliferativa importante quando comparados com a quercetina. A ação inibitória dos flavonóides sobre as DNA-topoisomerases I e II foi avaliada utilizando-se o ensaio de relaxação sobre o plasmídeo pBR322. Os resultados indicaram ação não seletiva dos flavonóides sobre as DNA-topoisomerases I e II.

Chemical investigation of methanol extract leaves from Annona dioica (Annonaceae) resulted in the identification of flavonoids kaempferol (1), 3-O-[3",6"-di-O-p-hydroxycinnamoyl]-beta-galactopyranosyl-kaempferol (2), 6"-O-p-hydroxycinnamoyl-beta-galactopyranosyl-kaempferol (3) and 3-O-beta-galactopyranosyl-kaempferol (4). The structures were unequivocally characterized by ¹H and 13C NMR spectroscopic analyses using 1D and 2D experiments. The cytotoxic effects of the flavonoids and flavonoid fraction (FF) were evaluated by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay against Ehrlich carcinoma cells. The results indicated that 1, 2, 3 and FF exhibit significant antiproliferative action when compared to quercetin. The inhibitory action on DNA-topoisomerase I and II of all the flavonoids was evaluated by relaxation assays on pBR322 plasmid DNA. The results indicated the inhibitory and non-selective effects of the flavonoids on DNA-topoisomerase I and II.

Três novos derivados naturais dos ácidos cinâmico e diidrocinâmico foram isolados das raízes de Brosimum gaudichaudii, além de mais quatorze substâncias naturais conhecidas (dez cumarinas, uma chalcona, os dois esteróides beta-sitosterol e 3beta-O-beta-D-glicopiranosil-beta-sitosterol e o triterpeno beta-amirina). As estruturas destas substâncias foram estabelecidas com base na análise de dados espectrais, inclusive experiências de RMN 2D e espectros de massas. O ácido 4-hidroxi-3-prenilcinâmico pode ser postulado como precursor para todas substancias aromáticas. As novas substâncias naturais são derivadas do precursor das cumarinas que perdeu a possibilidade de formar o anel lactônico devido a O-metilação.

Three new natural cinnamic acid and dihydrocinnamic acid derivatives were isolated from the roots of Brosimum gaudichaudii, in addition to fourteen known substances (ten coumarins, one chalcone, beta-sitosterol, 3beta-O-beta-D-glucopyranosylsitosterol and beta-amyrin). The structures were established by spectral data, including analysis of 2D-NMR experiments and mass spectra. All aromatic compounds have 4-hydroxy-3-prenylcinnamic acid as a common precursor. The new substances are derived from a precursor of the coumarins, which through an O-methylation lost its ability to form the lactone ring.

Um novo triterpeno pentacíclico, o 11alfa-metoxi-beta-amirina (1) foi isolado de Myroxylon balsamum (L.) Harms (sin. Myroxylon peruiferum L.f.). A estrutura desta substância foi elucidada pela análise de seus dados de IV, EM, RMN ¹H e 13C. RMN bidimensional foi também utilizada para definir a estrutura e atribuir os deslocamentos químicos dos átomos de hidrogênio e carbono do novo triterpeno.

The new pentacyclic triterpene, 11alpha-methoxy-beta-amyrin (1), was isolated from Myroxylon balsamum (L.) Harms (syn. Myroxylon peruiferum L.f.). Its structure was established on the basis of IR, MS, ¹H NMR, 13C NMR. 2D NMR experiments were also used to establish the structure and the hydrogen and carbon chemical shift assignments of the new triterpene.