Antinociceptive and anti-inflammatory activity of extracts and α-pyrones isolated from Cantinoa stricta.

This study evaluated the composition and the antinociceptive and anti-inflammatory activity of the crude extracts and two isolated compounds, anamarine (ANA) and 10-epi-olguine (eOL), obtained from the leaves of Cantinoa stricta (Lamiaceae). Crude ethanolic extract (EEt) and dichloromethane extract (DCM), selected based on NMR data, were submitted to pharmacological tests in male Swiss mice. The oral administration of EEt and DCM significantly reduced the second phase of formalin-induced nociception (60%), lipopolysaccharide (LPS)-induced mechanical hyperalgesia (90%), and carrageenan (Cg)-induced edema (25%). ANA and eOL, the major compounds in EEt and DCM extracts, administered orally or locally (in the paw), also reduced the LPS-induced mechanical hyperalgesia (Oral ID50 1.9 and 3.9 mg/kg; Local ID50 93.4 and 677.3 ng, respectively) without changing the thermal acute nociception or the motor performance of the animals. Local administration of ANA and eOL also reduced Cg-induced edema (40 and 23%, respectively). These isolated compounds did not change the mechanical hyperalgesia induced by tumor necrosis factor-α, interleukin-1ß, prostaglandin E2, dibutyryl cyclic AMP, or forskolin but reversed the hyperalgesia induced by dopamine, epinephrine, and phorbol 12-myristate 13-acetate. The hyperalgesia induced by epinephrine was reversed in male but not in female mice, in which this response is not dependent on protein kinase C (PKC). These results suggest that C. stricta extracts possess antinociceptive and anti-inflammatory activity which is related to the presence of ANA and eOL. Differently from the known analgesics, these substances seem to exert their action mainly interfering with the sympathetic component of pain, possibly with PKC.

Chemical Constituents from Sinningia canescens and S. warmingii.

A new naphthoquinone, 6-methoxy-7-hydroxy-a-dunnione (1), along with four known compounds (2, 4, 10, and 11) were isolated from Sinningia canescens (Mart.) Wiehler tubers, while S. warmingii (Hiern.) Chautems furnished eight known compounds (3-10). The known compounds were identified as 7-hydroxy- α-dunnione (2), lapachenole (3), tectoquinone (4), 7-methoxytectoquinone (5), 1-hydroxytectoquinone (6), 7-hydroxytectoquinone (7), aggregatin C (8), aggregatin D (9), halleridone (10), and cedrol (11). In addition, S. canescens yielded a volatile fraction, which was analyzed by GC/FID and GC/MS. This fraction was constituted mainly by sesquiterpene hydrocarbons (82.6%). The major components were ß-santalene (14.6%), ß-cedrene (10.4%), and trans-cadina-1(6)-4-diene (10.0%).

Antiproliferative activity and induction of apoptosis in PC-3 cells by the chalcone cardamonin from Campomanesia adamantium (Myrtaceae) in a bioactivity-guided study.

The Myrtaceae family is a common source of medicines used in the treatment of numerous diseases in South America. In Brazil, fruits of the Campomanesia species are widely used to make liqueurs, juices and sweets, whereas leaves are traditionally employed as a medicine for dysentery, stomach problems, diarrhea, cystitis and urethritis. Ethanol extracts of Campomanesia adamantium (Myrtaceae) leaves and fruits were evaluated against prostate cancer cells (PC-3). The compound (2E)-1-(2,4-dihydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one, cardamonin) was isolated from ethanol extracts of C. adamantium leaves in a bioactivity-guided study and quantified by UPLC-MS/MS. In vitro studies showed that the isolated chalcone cardamonin inhibited prostate cancer cell proliferation and decreased the expression of NFkB1. Moreover, analysis by flow cytometry showed that this compound induced DNA fragmentation, suggesting an effect on apoptosis induction in the PC-3 cell line.

Essential oil and other constituents from Magnolia ovata fruit.

The volatile and non-volatile constituents of the unripe fruits of Magnolia ovata (A. St.-Hil.) Spreng. (Magnoliaceae) were studied. The essential oils were obtained by hydrodistillation of the fruit of two plant populations (A and B) and analyzed by GC/FID and GC/MS. The oil of sample A was rich in sesquiterpenes, mainly spathulenol (19.3%), while the oil of sample B showed a predominance of aliphatic compounds, mainly hexadecanoic acid (52.0%). Extracts of the dried fruit contained fourteen known compounds including nine lignoids (magnovatin A, magnovatin B, acuminatin, licarin A, oleiferin A, oleiferin C, kadsurenin M, 4-O-demethylkadsurenim M and 7-epi-virolin), two sesquiterpene lactones (parthenolide and michelenolide) and three alkaloids (lysicamine, lanuginosine and O-methylmoschatoline). Michelenolide, 7-epi-virolin and lisycamine are reported for the first time in the species, while the remaining compounds have already been reported in the leaves and/or trunk bark o f Magnolia ovata. Acetylation o f oleiferin A yielded a ne wcompound, acetyl oleiferin A, whose NMR data and that of michelenolide are furnished.

Morphoanatomical and phytochemical studies of Salvia lachnostachys (Lamiaceae).

Salvia lachnostachys Benth., Lamiaceae, is a endemic species from southern Brazil. The essential oil of its leaves and flowers is mainly constituted by aliphatic compounds, such as dodecanoic acid, with sesquiterpenes as minor constituents. This work evaluated the morphology, anatomy, microchemistry, and phytochemistry of S. lachnostachys to provide advanced knowledge of Brazilian plants with medicinal potential. Light and scanning electron microscopy techniques were used in the anatomical and microchemical studies. Compounds were isolated by chromatographic techniques, identified by analysis of their NMR spectra and compared with published data. S. lachnostachys can be distinguished from other related species mainly by its petiolate leaves, terminal inflorescence, persistent bracts, and villous-glandular corolla. The stem and leaves of S. lachnostachys display anatomical characteristics common to the family Lamiaceae. However, this species can be distinguished from other family members by the morphology and the presence of eglandular and glandular trichomes, as well as the organization of the vascular bundles of the petiole. The phytochemical results revealed that S. lacnostachys produces oleanolic and ursolic acids in addition to the diterpene fruticuline A, which is a rare compound, previously found only in Salvia fruticulosa Benth. and S. corrugata Vahl. Ursolic and oleanolic acids are bioactive triterpenes that exhibit antiatherosclerotic, anticancer, antihypertensive, antinflammatory, antileukemic, antimutagenic, antioxidant, antiproliferative, and antiviral activities, and fruticuline A has antibacterial activity.

Free radical scavenging activity, determination of phenolic compounds and HPLC-DAD/ESI-MS profile of Campomanesia adamantium leaves.

Numerous diseases are induced by free radicals via lipid peroxidation, protein peroxidation and DNA damage. It has been known that a variety of plant extracts have antioxidant activity to scavenge free radicals. Campomanesia adamantium (Myrtaceae) is a small tree with edible fruit, commonly known as "guavira" or "guabiroba-branca" that has been used in popular medicine as depurative anti-diarrhoeic, antiinflammatory, anti-rheumatic and to liver diseases. In this study, the antiradical activities of ethanol crude extract of the leaves from C. adamantium and the ethyl acetate and butanol fractions obtained by partition, were determined using DPPH (2,2-Diphenyl-1-picrylhydrazyl radical) and ORAC-FL (Oxygen Radical Absorbance Capacity) assays. The total phenol content in the samples was estimated by Folin Ciocalteau method (FCR). In an initial evaluation the ethanolic extract and the fractions ethyl acetate and butanol have shown levels of phenolic compounds between 15- 74 mg GAE/g in FCR assay, showed DPPH free-radical scavenging activity with SC50 in the range of 7.77-13.35 microg/mL and demonstrated antioxidant capacity between 2648-3502 micromol TE/g of extract and fractions in the ORAC-FL assay. HPLC-DAD and ESI-MS analysis revealed were that the extract of the leaves of C. adamantium studied appears to contain flavonoids as major constituents, including isoquercetrin and quercetin that exhibit proven antioxidant activity.