Croton zehntineri is an aromatic plant native to the northeast of Brazil which is popularly used in folk medicine as a sedative and for the relief of gastrointestinal disturbances. The present work deals with the chromatographic analysis of the ethanolic extract of roots and stem of C. zehntineri allowed the isolation and characterization for the first time for this species of seven compounds named trans-docosanyl ferulato, acetyl aleuritolic acid, 3-O-methylquercetin, E-anethole, 2-hydroxy-4,6-dimethoxyacetophenone and a mixture of b-sitosterol and stigmasterol. Structural elucidation was done on the basis of spectral data, mainly by high field NMR and EIMS. The antioxidant activity (DPPH radical scavenging activity) was determined, only compound named 3-O-methylquercetin showed antioxidant activity (IC50 2.76.10-3 ± 9.6.10-5 mg/mL).

Abstract The chemical composition of the essential oils obtained from the fresh leaves of Cordia globosa (Jacq.) H.B.K., at different ontogenetic stages, were analyzed by GC and GC/MS. Twenty-three and 26 volatile constituents were identifed for the oils at the fowering and fructifcation stages, respectively. In both oils, the main compounds were bicyclogermacrene (22.7%-13.1%) and β-caryophyllene (11.9%-11.6%).

The oil from aerial parts of Eupatorium pauciflorum H. B. K. obtained by hydrodistillation was analyzed by GC and GC-MS. Twenty-four components, 92.9% of the total, were identified. The compounds α-pinene (16.0%), bicyclogermacrene (14.9%), α-humulene (12.9%) and β-caryophyllene (11.9%) were the most significant. Copyright © 2005 John Wiley & Sons, Ltd.

The essential oil from the fresh leaves of Capraria biflora (Scrophulariaceae), obtained by hydrodistillation process, was analyzed by CC and GC/MS. Nine compounds were characterized representing 91.1% of compounds present in the oil. The major components present were the sesquiterpenes beta-caryophyllene (29.6%) and gamma-muurolene (32.6%).

Capraria biflora L. (Scrophulariaceae) is a perennial shrub widely distributed in several countries of tropical America. The present work verified the cytotoxic and antioxidant potential of biflorin, an o-naphthoquinone isolated from C. biflora collected in the northeast region of Brazil. The cytotoxicity was tested on three different animal cell models: mouse erythrocytes, sea urchin embryos and tumor cells, while the antioxidant activity was assayed by the thiocyanate method. Biflorin lacked activity on mouse erythrocytes as well as on the development of sea urchin eggs, but strongly inhibited the growth of all five tested tumor cell lines, especially the skin, breast and colon cancer cells with IC50 of 0.40, 0.43 and 0.88 μg/ml for B16, MCF-7 and HCT-8, respectively. Biflorin also showed potent antioxidant activity against autoxidation of oleic acid in a water/alcohol system.

The essential oil of fresh leaves of Lippia aff. gracillis was analyzed by GC/MS and evaluated for its antibacterial effects. The results showed a moderate antibacterial activity and confirm the traditional uses of L. aff. gracillis.

A new monodesmoside triterpenoid saponin characterized as 3 beta-O-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-glucopyranosyl pomolic acid, was isolated from Cordia piauhiensis Fresen ( Boraginaceae). Its structure was determined by extensive NMR analysis, including H-1, H-1-COSY, HMQC, HMBC, and NOESY experiments. In addition, four known triterpenoids: quinovic acid, cincholic acid, cincholic 3 beta-O-6-deoxy-beta-D-glucopyranoside acid and quinovic 3 beta-O-beta-D-glucopyranoside acid were also isolated.

The essential oil from the fresh leaves of Lippia microphylla obtained by hydrodistillation was analyzed by GUMS. Twelve compounds were identified representing 99.9 % of the total components detected. The major constituents of the leaf oil were 1,8-cineole (36.0 %), thymol (11.1 %) and alpha-pinene (10.9 %).

Two new compounds, 5 and 8, and an epimeric mixture 4a/4b were isolated from hardwood of Auxemina glazioviana. Their structures and relative configurations were determined by modern spectroscopic analysis to be rel-10 alpha,11 alpha-epoxy-11 beta-ethoxy-8 alpha-hydroxy-2-methoxy-8a beta-methyl-5,6,7,8,8a,9,10,10a beta-octahydro-1,4-anthracenedione (or rel-2R,2aR,5R,5aS,10bS,10cS-2-ethoxy-5-hydroxy-8-methoxy-5a-methyl-2a,3,4,5,5a,6,10b,10c-octaliydi-o-2H-anthra[9,1-bc]furan-7,10-dione, 4a), rel-10 alpha,11 alpha-epoxy-ethoxy-8 alpha -hydroxy-2-methoxy-8a beta-methyl-5,6,7,8,8a,9,10,10a beta-octahydro-1,4-anthracenedione (or rel-2S,2aR,5R,5aS,10bS,10cS-2-ethoxy- 5-hydroxy-8-methoxy-5a-methyl-2a,3,4,5,5a,6,10b10c-octahydro-2H-anthra[9,1-bc]furan-7,10-dione, 4b), rel-10 alpha,11 alpha-epoxy-8 alpha, 11-dihydroxy-2-methoxy-8a beta-methyl-5,6,7,8,8a,9,10,10a beta-octahydro-1,4-anthracenedione (or rel-2S,2aR,5R,5aS, 10bS,10cS-2,5-dihydroxy-8-methoxy-5a-methyl-2a,3,4,5,5a,6,10b,10c-octahydro-2H-anthra[9,1-bc]furan-7,10-dione, 5) and ret-10,11-epoxy-8a beta-methyl-1,4,5 alpha,9 alpha-tetrahydroxy-5,6,7,8,8a,9,10,10a-octahydro-8-anthracenone (or rel-2aS,5aS,6R,10bR,10c5-2a,6,7, 10-tetrahydroxy-5a-methyl-2a,3,4,5,5a,6,10b,10c-octahydro-2H-anthra[9,1-bc]-furan-5-one, 8). In addition, known compounds were also isolated.

Essential oils obtained by hydrodistillation from heartwood and sapwood of Cordia trichotoma Vell. were analyzed by GC/FID and GC/MS. The essential oil compositions were similar and characterized by their higher abundance on sesquiterpenes. The main components were: α-cadinol (26.5%), α-muurolol (25.1%), epi-α-muurolol (20.9%), δ-cadinene (11.9%) and guaia-3, 10(4)-dien-11-ol (10.7%). Copyright © 2004 John Wiley & Sons, Ltd.

(1a S*,1b S*,7a S*,8a S*)-4,5-Dimethoxy-1a,7a-dimethyl-1,1a,1b,2,7, 7a,8,8a-octahydrocyclopropa cyclopenta[1,2-b]naphthalene-3,6-dione (1), a new meroterpenoid benzoquinone, and microphyllaquinone (2), a known naphthoquinone, have been isolated from roots of Cordia globosa. Both structure determinations were performed by conventional spectroscopic methods, including inverse detection NMR techniques, and by comparison with data from the literature for related compounds. Compound 1 displayed considerable cytotoxic activity against several cancer cell lines with IC50 values in the range of 1.2 to 5.0 microg/mL. The cytotoxic activity seemed to be related to DNA synthesis inhibition, as revealed by the reduction of 5-bromo-2'-deoxyuridine incorporation, and apoptosis induction, as indicated by the acridine orange/ethidium bromide assay and morphological changes after 24 h of incubation on leukemic cells.

Helindicine (1), a new pyrrolizidine alkaloid with unusual structural features, together with the known lycopsamine (2), were isolated from the roots of Heliotropium indicum (Boraginaceae). The structures were established by a combination of 1D and 2D NMR methods (COSY, HMQC, HMBC, and NOESY) and HREIMS. This is the first report of a lactone pyrrolizidine alkaloid in the genus Heliotropium. Compounds 1 and 2 were assayed for antioxidant activity and showed moderate activity.

The heartwood of two specimens of Auxemma glazioviana, collected in two localities of the state of Ceara, Brazil, were submitted to hydrodistillation and their essential oils were characterized by GC-MS. The major components found in the essential oils from Cristais were alpha-bisabolol (sample I, 46.3; sample II, 53.9%) and alpha-cadinol (sample I, 21.1%; sample II, 30.6%), while the essential oils from Quixada were dominated by a-cadinol (sample III, 37.8%) and cadalene (sample IV, 17.9%). The oils from Cristais (samples I and II) were examined with respect to their larvicidal properties against the larvae of a mosquito (Aedes aegypti) and showed LD50 2.98 ppm and 2.53 ppm, respectively. Copyright (C) 2004 John Wiley Sons, Ltd.

Two unnatural α-amino acid esters were prepared in good yields via phase transfer catalyzed Michael addition of ethyl N-acetylaminocyanoacetate to chalcone and benzalketone. For both α- enones, a progressive increase in product diastereomeric excess (d.e.) was observed during the course of reaction, even in the absence of quaternary ammonium salt. However, for a fixed reaction time, higher d.e. values were obtained under phase transfer catalytic condition. Analogous reactions were performed using S-aryl thiocinnamates as Michael acceptors, affording a 2-pyrrolidinone in good yield but low d.e. These results were interpreted on the basis of the reversibility of the Michael reaction

The essential oil from the aerial parts of Baccharis trinervis (Lam.) Pers., obtained by hydrodistillation, was analyzed by GC-MS, as well as by H-1 and C-13 NMR. alpha-Thujene, alpha-pinene, sabinene, beta-pinene, beta-phellandrene, (E)-lachnophyllum acid methylester and (Z)-lachnophyllum acid methyl ester were found to be the major components among the identified constituents. Evaluation of the in vitro antimicrobial activity of the essential oil against four bacteria and one fungus is also reported.

Two new secondary metabolites, the phenylpropanoid 3-(2′,4′,5′-trimethoxyphenyl)propanoic acid (1) and the sesquiterpene (+)-1β,4β,6α-trihydroxyeudesmane (2) were isolated from the heartwood of Cordia trichotoma Vell., along with the known sesquiterpenes (D)-1β,4β,7α- trihydroxyeudesmane (3) and (+)-1β,4β,11-trihydroxyoppositane (4). Their structures were elucidated by means of spectroscopic data interpretation, mainly 1D and 2D NMR and mass spectrometry.

Oncocalyxone A (1) (rel-8α-hydroxy-5-hydroxymethyl-2-methoxy-8aβ-methyl-7,8,8a,9- tetrahydro-1,4-anthracenedione) is a 1,4-anthracenedione that has been shown to be cytotoxic to human tumor cells and to be DNA reactive. Three derivatives of 1 obtained by chlorination (6- chloro-oncocalyxone A, 2) and acetylation (11-O-acetyloncocalyxone A, 3; 8,11-O- diacetyloncocalyxone A, 4) were found to be less cytotoxic and less DNA reactive in human leukemia cells. These derivatives were less polar compounds with modifications that may have hindered binding of the compound to DNA.

Bis-biflorin, a new o-naphthoquinone dimer, and biflorin, 6,9-dimethyl-3-(4-methyl-3-pentenyl)naphtho[1,8-bc]-pyran-7,8-dione, were isolated from roots of Capraria biflora, a medicinal plant from northeast Brazil. Structural elucidation was made on the basis of spectral data, mainly by high-field NMR and high-resolution mass spectrometry. Copyright (C) 2003 John Wiley Sons, Ltd.

Extensive 1D (H-1 NMR, HBBD-C-13 NMR, DEPT-C-13 NMR) and 2D (COSY, TOCSY, NOESY, HMQC and HMBC) NMR analysis was used to characterize the structure of a new bisdesmoside saponin isolated from the methanol extract of stems of Cordia piauhiensis Fresen as 3beta-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl]ursolic acid 28-O-[beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester. Copyright (C) 2003 John Wiley Sons, Ltd.

Abstract A new prenylated naphthoquinone dimer named microphyllaquinone (1), a mixture of 6-methoxy- and 7-methoxy-naphtho[2,3-b]-furan-4,9-quinones (2a/2b) and tecomaquinone I (3), were isolated from roots of Lippia microphylla. The structures were elucidated by spectroscopic methods, including detailed 1D and 2D (COSY, NOESY, HMQC, HMBC) NMR data. Unpublished 13C NMR data of 2a and 2b are reported. The in vitro cytotoxic activity of the isolated compounds was tested against five types of tumor cells.