Natural sesquiterpenoids

This review covers the isolation, structural determination, synthesis and chemical and microbiological transformations of natural sesquiterpenoids. The literature from January to December 2005 is reviewed,and 386 references are cited.     

Natural sesquiterpenoids

This review covers the isolation, structural determination, synthesis and chemical and microbiological transformations of natural sesquiterpenoids. The literature from January to December 2001 is reviewed, and 404 references are cited.     

Natural sesquiterpenoids

This review covers the isolation, structural determination, synthesis and chemical and microbiological transformations of natural sesquiterpenoids. The literature from January to December 2003 is reviewed, and 389 references are cited.     

Natural sesquiterpenoids

This review covers the isolation, structural determination, synthesis and chemical and microbiological transformations of natural sesquiterpenoids. 421 references are cited.     

Natural sesquiterpenoids

This review covers the isolation, structural determination, synthesis and chemical and microbiological transformations of natural sesquiterpenoids. The literature from January to December 2002 is reviewed, and 388 references are cited.     

The dihydro-beta-agarofuran sesquiterpenoids

Dihydro-Beta-agarofuran sesquiterpenoids are a structurally diverse class of natural products based on tricyclic 5,11-epoxy-5Beta,10alpha-eudesman-4-(14)-ene skeleton. Between January 1990 and June 2006, 462 new dihydro-Beta-agarofuran sesquiterpenoids of 74 structural types have been isolated from about 64 species of Celastraceae, 3 species of Hippocrateaceae and one species of Lamiaceae. The present review covers the chemical and biological activity research of dihydro-Beta-agarofuran sesquiterpenoids in the past 16 years. The chemical research includes structural classification into sesquiterpene polyesters and macrolide sesquiterpene pyridine alkaloids, synthesis of dihydro-Beta-agarofuran as well as extraction, isolation and purification methods. The biological activity research includes activities such as multidrug resistance (MDR) reversal activity, HIV inhibition, cytotoxicity, antitumor activity, antifeedant activity and insecticidal activity with some insights to their modes of actions.     

Brasilane-type sesquiterpenoids from Laurencia obtusa

[structure: see text] Three novel halogenated rearranged sesquiterpenes (1-3) have been isolated along with brasilenol (4) and epibrasilenol (5) from the organic extract of the red alga Laurencia obtusa, collected at Symi island in the Aegean Sea, Greece. The new metabolites possess the unusual skeleton of brasilane and contain the unprecedented 1,6-epoxy moiety. The structures of the new natural products, as well as their relative stereochemistry, were established by means of spectral data analyses, including two-dimensional NMR experiments along with molecular calculations.     

Antimicrobial sesquiterpenoids from Laurus nobilis L

Activity-guided fractionations of leaf extracts from Laurus nobilis L. led to the isolation of a known sesquiterpene lactone, deacetyl laurenobiolide (1). Compound 1 showed antimicrobial activity against periopathic pathogens (Actinomyces viscosus, Porphyromonas gingivalis, Prevotella intermedia and Actinobacillus actinomycetemcomitans), opportunistic Gram-positive bacteria (Staphylococcus aureus and Streptococcus pyogenes) and fungi (Candida albicans, Cryptococcus neoformans and Aspergillus fumigatus). Furthermore, acetylation and cyclisation of deacetyl laurenobiolide (1) yielded laurenobiolide (2) and a new compound, (5S,6R,7S,8S,10R)-6,8-dihydroxyeudesma-4(15),11(13)-dien-12-oic acid 12,8-lactone (3), respectively. Compounds 2 and 3 also showed antimicrobial activities. All compounds 1-3 demonstrated growth inhibitory effects with minimum inhibitory concentrations ranging from 31 to 1000?μg?mL(-1). This is the first report of compounds 1-3 showing antimicrobial activities.     

New cadinane sesquiterpenoids from Mikania micrantha

Abstract

Chemical investigation of the aerial parts of Mikania micrantha led to the isolation of eight sesquiterpenoids and ten diterpenoids, including five cadinane sesquiterpenoids (1?5), three bisabolene sesquiterpenoids (6???8), nine ent-kaurane diterpenoids (9–17), and an abietane diterpenoid (18). Among them, 1???3 are new and feature a rare lactone or furan ring derived from C-6 isopropyl group side chain. Compound 18 was isolated from genus Mikania for the first time, and was also the first example of abietane-type diterpenoids from this plant. Their structures were elucidated on the basis of extensive spectroscopic analyses (1D and 2D NMR, HRESIMS, and ECD). All compounds were examined for their inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW 264.7 macrophage cells, and compound 18 exhibited pronounced inhibition on NO production (IC₅₀ = 11.04?µM), being comparable to the positive control, quercetin (IC₅₀ = 11.15?µM).     

Cytotoxic oplopane sesquiterpenoids from Arnoglossum atriplicifolium

Pale Indian plantain (Arnoglossum atriplicifolium (L.) H. Rob.) is a plant with traditional medicinal usage among the Cherokee Native American tribe for treating cancer. Two oplopane sesquiterpenoids were isolated from an extract of A. atriplicifolium from Western North Carolina. The compounds were isolated by bioassay-guided fractionation using an MCF-7 breast tumour cell line assay. The known compound (1S,6R,7R,8R)-1-acetoxy-6,7-diangeloxy-8,10-epoxy-2-oxo-oplopa-3,14Z,11,12-dien-13-al (1) had an EC₅₀ value of 9.0 μM against MCF-7 cells, while the new compound (1S,3R,6R,7R,8R,11S)-1-acetoxy-6,7-diangeloxy-8,10,11,13-bisepoxyoplopan-2-one (2) had an EC₅₀ value of 96 μM. The compounds were characterised by 1D and 2D NMR spectroscopy and by comparison with literature values in the case for 1. Based on NOESY analysis, a correction of the relative configuration for 1 is presented. The presence of these compounds may help to explain the folk remedy usage of this plant as an anticancer agent.