New antimicrobial cyclolignan and others constituents from the leaves of Scyphocephalium mannii (Benth. & Hook.f.) Warb.

Chemical investigation of the MeOH extract of the leaves of Scyphocephalium mannii (Benth. & Hook.f.) Warb. (Myristicaceae) led to the isolation and characterization of one new metabolite (+)-(7'S, 8S, 8'S)-4,4'-dihydroxy-3,3',5,5'-tetramethoxy-2,7'-cyclolignan (1) along with five known compounds. Their structures were elucidated by spectroscopic means, including 1 D and 2 D NMR, HRESI-MS and by comparison with published data. The absolute configuration of compound 1 was determined by single-crystal X-RAY diffraction. Compound 1 showed moderate antifungal activity against Cryptococcus neoformans with respective MIC and MMC values of 64 and 256 µg/mL.

Bioguided identification of pentacyclic triterpenoids as anti-inflammatory bioactive constituents of Ocimum gratissimum extract.

ETHNOPHARMACOLOGICAL RELEVANCE: Ocimum gratissimum is a plant spice widely used in African traditional medicine to treat pain-related conditions. However, the anti-inflammatory mechanisms underlying this activity and the main active ingredients in O. gratissimum have not yet been fully characterized. AIM OF THE STUDY: To isolate and identify the main anti-inflammatory active constituents of Ocimum gratissimum extract and their underlying mechanisms in murine macrophages. MATERIAL AND METHODS: Chromatographic techniques and spectroscopic data were used for compounds isolation and identification. Inflammatory conditions were produced in cultured RAW 264.7 macrophage cells by the application of lipopolysaccharide (LPS). The WST-1 assay was used to evaluate the cell viability, and the nitric oxide production was quantified by the Griess reagent method. The fluorometric cyclooxygenase (COX) activity assay kit was used to assess the activity of COX-1 and COX-2 enzymes. The levels of IFN-γ, TNF-α, IL-2, IL-4, IL-6, and IL-10 cytokines and the apoptosis-inducing effect were measured by flow cytometer using the cytometric Bead Array (CBA) Human Th1/Th2 Cytokine Kit II and FITC Annexin V Apoptosis Detection kit, respectively. RESULTS: The results showed that the extract and fractions of Ocimum gratissimum inhibit nitric oxide production and the proliferation of Raw 264.7 macrophage cells. The bioguided fractionation led to the identification of pentacyclic triterpenes as anti-inflammatory bioactive compounds. Pomolic and tormentic acids being the most active, inhibiting the secretion of IFN-γ cytokine, COX enzyme, and inducing apoptosis in activated Raw 264.7 macrophage cells. CONCLUSIONS: This study revealed that pomolic and tormentic acids are the main active principles responsible at least in part for the anti-inflammatory effect of the extract of Ocimum gratissimum. Besides of providing more evidence for the traditional use of Ocimum gratissimum against inflammatory disorders, this study reveals the multitarget potential of pomolic and tormentic acids as promising future drugs against inflammatory diseases.

Bioactive chemical constituents of Duboscia macrocarpa Bocq., and X-ray diffraction study of 11ß, 12ß-epoxyfriedours-14-en-3α-ol.

A new γ-lactone triterpenoid, Evodoulolide (1) and a new triterpenoid Duboscic acid B (2), along with five known compounds, maslinic acid (3), arboreic acid (4), (E)-3-(4-hydroxyphenyl)-N-[2-(4-hydroxyphenyl) ethyl] prop-2-enamide (5), (E)-heptacos-19-enoic acid (6) and 11ß,12ß-epoxyfriedours-14-en-3α-ol (7) were isolated from the trunk wood of Duboscia macrocarpa. Their structures were elucidated from extensive 1D- and 2D-NMR and MS and by comparison of their spectra with published data. Compounds 1, 3, 5 and 6 exhibited significant α-glucosidase inhibitory activity. Compound 5 was found to be a potent inhibitor (IC50=5.1±0.1µM) of α-glucosidase as compared to acarbose (IC50=625.0±1µM) used as standard drug. These compounds did not show anti-glycation activity using the BSA-MG glycation model or inhibition against the α-chymotrypsin enzyme. The chemotaxonomic connotation of the isolated secondary metabolites is also herein described. The single-crystal X-ray and absolute configuration diffraction analysis of 11α, 12α-epoxyfriedours-14-en-3-ol (7) is also described here for the first time.

Neomacrodione: a new degraded diterpenoid from the roots of Neoboutonia macrocalyx Beng (Euphorbiaceae).

One new degraded diterpenoid 3,6-dihydroxy-1,7-dimethyl-9,10-phenantroquinone (neomacrodione) (1) together seven known compounds were isolated from the roots of Neoboutonia macrocalyx (Euphorbiaceae). The structures of the compounds were established based on their NMR and mass spectrometric data in conjunction with those previously reported in the literature. Compound (1) displayed moderate antibacterial activities.