Ent-kaurane diterpenoids and other constituents from the stem of Xylopia laevigata (Annonaceae)

Phytochemical investigation of the hexane extract from the stem of Xylopia laevigata led to the isolation of the ent-kaurane diterpenoids, ent-kaur-16-en-19-oic acid, 4-epi-kaurenic acid, ent-16β-hydroxy-17-acetoxy-kauran-19-al, ent-3β-hydroxy-kaur-16-en-19-oic acid, and ent-16β,17-dihydroxy-kauran-19-oic acid, as well as spathulenol and a mixture of β-sitosterol, stigmasterol and campesterol. The identification of the compounds was performed on the basis of spectrometric methods including GC-MS, IR, and 1D and 2D NMR. Potent larvicidal activity against Aedes aegypti larvae with LC50 of 62.7 µg mL-1 was found for ent-3β-hydroxy-kaur-16-en-19-oic acid. This compound also showed significant antifungal activity against Candida glabrata and Candida dubliniensis with MIC values of 62.5 µg mL-1.

Estudo por espectrometria de massas de soluções de hidróxi(tosilóxi)iodobenzeno: propostas para mecanismos de desproporção

Solutions of [hydroxy(tosyloxy)iodo]benzene (HTIB or Koser's reagent) in acetonitrile were analyzed using high resolution electrospray ionization mass spectrometry (ESI-MS) and electrospray ionization tandem mass spectrometry (ESI-MS/MS) under different conditions. Several species were characterized in these analyses. Based on these data, mechanisms were proposed for the disproportionation of the iodine(III) compounds in iodine(V) and iodine(I) species.

Synthesis and biological evaluation of biaryl analogs of antitubulin compounds

This paper reports the synthesis of methanones and esters bearing different substitution patterns as spacer groups between aromatic rings. This series of compounds can be considered phenstatin analogs. Two of the newly synthesized compounds, 5a and 5c, strongly inhibited tubulin polymerization and the binding of [³H] colchicine to tubulin, suggesting that, akin to phenstatin and combretastatin A-4, they can bind to tubulin at the colchicine site.

Fitoquímica e quimiossistemática de Conchocarpus marginatus e C. inopinatus (Rutaceae)

Phytochemical studies of the leaves and stem have led to the identification of the known acridone alkaloids arborinine, methyl-arborinine, 1-hydroxy-3-methoxy-N-methyl acridone, xanthoxoline, 1,2,3,5-tetramethoxy-N-methylacridone, toddaliopsin C and the new seco acridone alkaloid inopinatin. The known quinoline alkaloids 2-phenyl-1-methyl-quinolin-4(1H)-one, 2-phenyl-1-methyl-7-methoxy-quinolin-4(1H)-one, dictamnine, and the coumarins scopoletin and marmesin were also isolated. The isolated compounds and the distribution of secondary metabolites, which are systematically important, obtained from literature, clearly confirmed that some species formerly described in the genera Angostura and Galipea in fact shall belong to the genus Conchocarpus.

Flavonoides e sesquiterpenos de Croton pedicellatus Kunth

The chemical investigation of the ethanolic extract from leaves of Croton pedicellatus yielded the bis-nor-sesquiterpenes blumenol A and blumenol A glucoside, along with the flavonoids: tiliroside, 6"-O-p-coumaroyl-β-galactopyranosyl- kaempferol, 6"-O-p-coumaroyl-β-glucopyranosyl-3"-methoxy- kaempferol, kaempferol, 3-glucopyranosyl-quercetin and alpinumisoflavone, as well as 4-hydroxy-3,5-dimethoxybenzoic acid. The identification of all isolated compounds was performed by spectrometric methods, including HR-ESI-MS, 1D and 2D NMR experiments, and by comparison with previously-described physical and spectral data.

Other compounds isolated from Simira glaziovii and the ¹H and 13C NMR chemical shift assignments of new 1-epi-castanopsol

A new triterpene, 1-epi-castanopsol, besides eleven known compounds: sitosterol, stigmasterol, campesterol, lupeol, lupenone, simirane B, syringaresinol, scopoletin, isofraxidin, 6,7,8-trimethoxycoumarin and harman, were isolated from the wood of Simira glaziovii. The structures of the known compounds were defined by 1D, 2D ¹H, 13C NMR spectra data analyses and comparison with literature data. The detailed spectral data analyses allowed the definition of the structure of the new 1-epi isomer of castanopsol and performance of ¹H and 13C NMR chemical shift assignments.

Phaeophytins from Thyrsacanthus ramosissimus Moric. with inhibitory activity on human dna topoisomerase II-α

Our study reports the extraction and isolation of a new phaeophytin derivative 15¹-hydroxy-(15¹-S)-porphyrinolactone, designated anamariaine (1) herein, isolated from the chloroform fraction of aerial parts of Thyrsacanthus ramosissimus Moric. along with the known 15¹-ethoxy-(15¹-S)-porphyrinolactone (2). These compounds were identified by usual spectroscopic methods. Both compounds were subjected to in vitro (inhibitory activity) tests by means of supercoiled DNA relaxation techniques and were shown to display inhibitory activity against human DNA topoisomerase II-α at 50 µM. Interconversion of these two pigments under the mild conditions of the isolation techniques should be highly unlikely but cannot be entirely ruled out.

Estudo fitoquímico e avaliação da atividade anti-inflamatória de Aeschynomene fluminensis vell. (Fabaceae)

Phytochemical investigation of Aeschynomene fluminensis leaves and branches led to isolation of the flavonoid glycosides kaempferol 3,7-di-O-α-L-rhamnopyranoside, kaempferol 7-O-α-L-rhamnopyranoside, kaempferol 3-O-apiofuranosil-7-O- rhamnopyranoside, quercitin 3-O-α-L-rhamnopyranoside, quercitin 3-O-arabinofuranoside, 8-β-D-glucopyranosyl 4',5,7-trihydroxyflavanone, the isoflavonoid 4',7-di-hydroxy-isoflavone, the dimer epicatechin-(2β→7, 4β→8)- epicatechin, the polyol 3-O-methyl-chiro-inositol and two steroids in sitosterol and stigmasterol mixture. These compounds were identified by NMR ¹H and 13C and compared with literature data. Anti-inflammatory activity of the crude methanolic extract and its fractions was evaluated.

Volatile and non-volatile compounds and antimicrobial activity of Mansoa difficilis (Cham.) Bureau & K. Schum: (Bignoniaceae)

Essential oil from the leaves of Mansoa difficilis was analyzed by GC/MS. Oct-1-en-3-ol (49.65%) was the major compound, but diallyl di- and trisulfide were also present (0.85 and 0.37%, respectively), justifying the garlic-like odor of the crushed leaves. The hexane and methanol extracts of the leaves and stems afforded as main constituents a mixture of linear hydrocarbons, spinasterol, stigmasterol, ursolic and oleanolic acids, two apigenin derivatives and verbascoside. The hexane and methanol extracts of leaves were tested for antimicrobial activity against ten microorganisms. The hexane extract was active against both Psedomonas aeruginosa and Staphylococcus aureus.

Synthesis and biological activity of sulfur compounds showing structural analogy with combretastatin A-4

We extended our previous exploration of sulfur bridges as bioisosteric replacements for atoms forming the bridge between the aromatic rings of combretastatin A-4. Employing coupling reactions between 5-iodo-1,2,3-trimethoxybenzene and substituted thiols, followed by oxidation to sulfones with m-CPBA, different locations for attaching the sulfur atom to ring A through the synthesis of nine compounds were examined. Antitubulin activity was performed with electrophoretically homogenous bovine brain tubulin, and activity occurred with the 1,2,3-trimethoxy-4-[(4-methoxyphenyl)thio]benzene (12), while the other compounds were inactive. The compounds were also tested for leishmanicidal activity using promastigote forms of Leishmania braziliensis (MHOM/BR175/M2904), and the greatest activity was observed with 1,2,3-trimethoxy-4-(phenylthio)benzene (10) and 1,2,3-trimethoxy-4-[(4-methoxyphenyl) sulfinyl]benzene (15).

Pregnanos e outros constituintes das raízes de Macrosiphonia petraea (A. St.-Hil.) Kuntze (Apocynaceae)

Macrosiphonia petraea (A. St.-Hil.) Kuntze is a plant popularly known as "velame". Its root infusion is used in the folk medicine of Mato Grosso do Sul, Brazil, for the treatment of inflammatory diseases. Phytochemical investigation of the roots of this species led to the identification of 17 compounds belonging to four different classes: two pregnanes, 12β-hydroxypregna-4,6,16-triene-3,20-dione, neridienone A, and 12β-hydroxypregna-4,6-diene-3,20-dione, cybisterol, one hydroxylated fatty acid, 5-hydroxy-octadeca-6(E)-8(Z)dienoic acid, two lignoids, pinoresinol and 8a-hydroxypinoresinol, ten pentacyclic triterpenoids, and two steroids.

Constituintes químicos de Vernonia scorpioides (Lam) Pers. (Asteraceae)

The chemical investigation of hexane and ethanol extracts from the aerial parts of Vernonia scorpioides resulted in the isolation and characterization of a new polyacetylene lactone, rel-4-dihydro-4β-hydroxy-5a-octa-2,4,6-triynyl-furan-2-(5H)-one, along with the new ethyl 3,4-dihydroxy-6,8,10-triynyl-dodecanoate, and seven known compounds: taraxasteryl acetate, lupeyl acetate, lupeol, lupenone, β-sitosterol, stigmasterol and luteolin. The structure of all compounds was determined by spectrometric techniques (HR-ESI-MS, ¹H and 13C NMR and IV) and comparison with published spectral data.

Flavonoides e terpenoides de Croton muscicarpa (Euphorbiaceae)

A new sesquiterpene and twelve known compounds comprising eight flavonoids and four terpenoids, were isolated from the leaves, stems, roots and exudate of Croton muscicarpa Müll. Arg.. Their structures were identified as the terpenoids 6α-methoxy-cyperene, dammaradienol, squalene, acetyl aleuritolic acid and spathulenol, and as the flavonoids retusin, 3,7,4'-trimethoxy kaempferol, ombuine, pachipodol, kaempferol, casticin, 5-hydroxy-3,6,7,4'-tetramethoxyflavone and artemetin. All isolated compounds were characterized based on IR, MS, ¹H and 13C NMR, including 2D analyses (COSY, HSQC, HMBC, NOESY) and comparison with data from the literature.

Trachylobane and kaurane diterpenes from Croton floribundus spreng

A new trachylobane diterpene ent-trachyloban-18,19-diol (1) was isolated from root bark of Croton floribundus, along with known diterpenes ent-trachyloban-19-oic acid (2), 15b-hydroxy-ent-trachyloban-19-oic acid (3), ent-trachyloban-19-ol (4), ent-kaur-16-en-19-oic acid (5), ent-kaur-16-ene-6a,19-diol (6) and ent-16a-hydroxykaur-11-en-19-oic acid (7). ent-trachyloban-18,19-diol (1) was submitted to derivatization reactions affording four new compounds (8-11). Cytotoxic activity of diterpenes 1, 3, 4, 7-11 against three human cancer cell lines was evaluated. No compounds showed cytotoxic potential with IC50 values greater than 25 mg/mL. Compound 6 was evaluated against five human cancer cell lines, showing moderate effect against three cancer cell lines, MDA-MB-435, HCT-8 and HCT-116, with IC50 values of 14.32, 13.47 and 12.1 mg/mL, respectively.

Isolation and antitrichomonal activity of the chemical constituents of the leaves of Maytenus phyllanthoides Benth. (Celastraceae)

Cyclolignan (+)-lyoniresinol (1), veratric acid (2), vanillic acid (3), lupeol, oleanolic acid, 3β-hydroxy-urs-11-en-28,13β-lactone (4), the mixture of α- and β-amyrin, trans-polyisoprene, and β-sitosterol were isolated from the leaves of Maytenus phyllanthoides. The structures of the isolated compounds were established based on spectroscopic data, mainly ¹H and 13C nuclear magnetic resonance (NMR). Compound 1, its acetate analog 1a, and compounds 2, 3, and 4 were tested against Trichomonas vaginalis. (+)-Lyoniresinol showed activity corresponding to IC50 17.57 µM. This is the first report on the occurrence of 3β-hydroxy-urs-11-en-28,13β-lactone (4) in the Celastraceous family and lyoniresinol in the Maytenus genus, and on the antitrichomonal activity of lyoniresinol.