<p>The phytochemical investigation and evaluation of the phytotoxic effect of the extract and fractions obtained from the leaves of <italic>Annona nutans</italic>(R. E. Fr.) R. E. Fr. were performed. Phytotoxic activity was assessed on radicle and hypocotyl of <italic>Allium cepa</italic> and <italic>Lactuca sativa</italic>, where chloroform and ethyl acetate fractions proved active. Phytochemical investigation of the chloroform fraction was allowed identification of polyketides derivatives: triacontanal, 16-hentriacontane, octacosanol and triacontanol, using the ¹H NMR technique associated with data from GC/MS. Using ethyl acetate fraction, with low activity, flavonoids 3-<italic>O</italic>-β-D-galactopyranosyl-isorhamnetin, 3-<italic>O</italic>-β-D-galactopyranosyl-quercetin and 3-<italic>O</italic>-β-D-apiofuranosyl-(1→2)-galactopyranosyl-quercetin were identified, determined by spectrometric techniques one and two-dimensional NMR, combined with mass spectral data. All substances are being reported for the first time in <italic>Annona nutans</italic>. The phytotoxic activity of chloroform fraction may be related to the presence of triacontanol and similar substances. Triacontanol stimulates growth at very low concentrations, but can have an inhibitory effect at higher concentrations, such as those reported for auxin analogs. The toxicity assay using <italic>Artemia salina</italic> (BST) was also performed, with the chloroform fraction showing a negligible lethal dose, LD₅₀ = 500 mg mL^-1, while the other fractions and extracts showed no activity. Thus, the presence of acetogenins was ruled out.</p>

Cochlospermum regium (Schrank) Pilg., Bixaceae, is a Brazilian plant widely used as a folk medicine in the southwestern of the Brazil to treat inflammation and infection diseases. However, the effects of C. regium hydroethanolic extract on pregnant rats have not been assessed. To evaluate the effects of the C. regium on pregnant rats during the organogenic period, the hydroethanolic extract was administered via gavage at a dose of 11.5 mg/kg/day to rats from 6th to 15th day of pregnancy. No clinical signs of maternal toxicity were observed. The placenta's and fetuses' weight were similar in control and treated animals. The term fetuses dis not present malformations or anomalies although the number of live fetuses and birth rate were significantly decreased. In conclusion, the C. regium hydroethanolic extract is nontoxicant to the pregnant rat although it would be likely to interfere in the progress of the embryofetal development.

This study describes the chemical investigation of the ethyl acetate fraction obtained from the hydroethanolic extract of the xylopodium of Cochlospermum regium (Mart. & Schr.) Pilger, which has been associated with antimicrobial activity. Phytochemical investigation produced seven phenol derivatives: ellagic acid, gallic acid, dihydrokaempferol, dihydrokaempferol-3-O-β-glucopyranoside, dihydrokaempferol-3-O-β-(6"-galloyl)-glucopyranoside, pinoresinol, and excelsin. It also contained two triacylbenzenes, known as cochlospermines A and B. The hydroethanolic extract and its fractions exhibited antimicrobial activity (0.1 mg/mL) against Staphylococcus aureus and Pseudomonas aeruginosa. Gallic acid showed activity against S. aureus. Dihydrokaempferol-3-O-β-(6"-galloyl)-glucopyranoside is reported here for the first time in the literature.

A different methodology was used to isolate and purify oxoaporphine alkaloids, as they are difficult to separate by the usual workup when in mixture. Alkaloid extracts from Annonaceae species were obtained by base/acid extraction. The extracts were concentrated and submitted to partition in solutions of acids of different pKa values, followed by separation by preparative TLC using 1 mm thick silica gel impregnated with oxalic acid (11.2% w/w). Liriodenine, lisycamine, lanuginosine, and O-methylmoschatoline were obtained and tested against tumoral cells (line Hep2, ATCC-CCL 23, larynx carcinoma). Only O-methylmoschatoline (IC50 12.4 µM) was more active than cisplatin (18.0 µM).

Duguetia furfuracea is a shrub of the Annonaceae family that occurs in several regions in Brazil. In the state of Mato Grosso do Sul this species often becomes an invading plant when the cerrado is turned into pastures. In the local folk medicine, its powdered seeds are mixed with water and used against pediculosis, and the infusion of twigs and leaves is used to treat rheumatism.. The present work led to the isolation and characterization from the aerial parts of the plant (leaves and twigs), of twelve isoquinoline alkaloids of aporphine oxoaporphine, bisbenzyltetrahydro-isoquinoline, benzyltetrahydro-isoquinoline and tetrahydroprotoberberine skeletons. In addition b-sytosterol and the flavonoid isorhamnethin were obtained. The activity of these different patterns of isoquinoline skeleton and the flavonoid was tested against Trypanosoma cruzi, and only aporphinoid skeleton with (R)-configuration, (-)-asimilobine, was really effective against trypomastigotes (strain Y), killing approximately 72% of the parasites at a maximal concentration of 128.0 mM (IC50 57.2 mM). The trypanocidal activity of the alkaloids and the flavonoid have been investigated

Memora peregrina (local name: 'ciganinha' - Bignoniaceae) is a weed that often invades pastures in the Brazilian state of Mato Grosso do Sul. From its leaves and subterranean parts, the following compounds were isolated: allantoin (20.7 w/w in subterranean parts), the iridoid 6beta-hydroxyipolamiide, hyperin, 3'-O-methylhyperin, 4-hydroxy-N-methylproline, beta-sitosterol, alpha-amirin and beta-amirin, and lupeol. Allantoin exhibited an activity of inducing germination in seeds of Lactuca sativa used as a biological model, and the iridoid showed moderate activity in the larval development of Anagasta kuehniella. These results, associated with this plant's behavior, are suggestive of the occurrence of adaptive and competitive strategies in relation to other plant species.

Five novel santalane-type sesquiterpenes were isolated from the stem bark of Duguetia glabriuscula - Annonaceae. Their structures have been established on the basis of spectral data and chemical evidences (¹H and 13C NMR, HMQC, HMBC) as (+)-alpha-santal-10-en-9-ol (1), (+)-alpha-santalan-10,11-epoxy-9-ol (2), alpha-santal-11-en-9,10-diol (3), (+)-alpha-santalan-9,10,11-triol (4), and (+)-alpha-santalan-9,11-epoxy-10-ol (5). Polycarpol, a triterpenoid, was also obtained.

The extract obtained from stem bark of Duguetia glabriuscula - Annonaceae was evaluated by Brine Shrimp Lethality test (BSL). The bioactive compounds, oxobufoline and lanuginosine, two oxoaporphine alkaloids were isolated by activity-guided fractionation. In addition, the compounds asaraldehyde, (+)-allo-aromadendrane-10beta, 14-diol, and two aporphine alkaloids, polyalthine and oliveridine were also obtained.

Extracts obtained from leaves, seeds and bark of Unonopsis lindmanii were evaluated by means of Brine Shrimp Lethality test (BSL). Through bioassay-guided chromatographic fractionation, liriodenine, an oxoaporphine alkaloid, was isolated from the bark extracts as the bioactive compound. Two additional inactive known alkaloids, unonopsine and lysicamine were also isolated from the bark extracts.

The sesquiterpene (+)-allo-aromadendrane-10b-14-diol 1 was the lead compound to the preparation of several derivatives in order to test their biological activity against A. salina, C. sphaerospermum, E. coli and S. aureus. In this way the monoalcohols (+)-viridiflorol 4, 9 and 11 were synthesized from 1 together with the acetal 6, the ketal 7, and the ketone 8. The oxirane 3 and nitrile 5 were also prepared using as an intermediate the tosylate derivative 2.