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ABSTRACT: Three new dolastane diterpenes (1-3) and five previously reported perhydroazulenes were isolated from the organic extracts of the brown alga Dilophus spiralis. The structure elucidation and the assignment of the relative configurations of the isolated natural products were based on extensive analyses of their spectroscopic data, whereas the absolute configuration of metabolite 2 was determined through its chemical conversion to a previously isolated compound of known configuration.
Marine Drugs 01/2013; 11(4):1104-12. · 3.85 Impact Factor
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ABSTRACT: The pine scale (Marchalina hellenica) has been introduced to Attica and reached unprecedented population densities. Using a randomised transect-based sampling
design in eight sites, we sampled the insect in random 10cm squares on the trunk and main branches of pine trees. The insect
did not show any clumping other than a micro-site preference for fissures and cracks. Canonical discriminant analysis and
generalised multinomial logit regression modelling were used to determine the most important ecological variables which were
the following: the population density of the insects; crown transparency; mean distance between trees; and the quality of
the habitat. The site and the distance from the line transect were insignificant. The interaction of crown transparency with
the abundance of the insect, the mean distance between trees and the quality of each site were important in configuring the
level of damage sustained by the pine tree.
Keywords
Marchalina hellenica
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Pinus halepensis
-Generalised multinomial logistic regression-Crown transparency-Site index-Stomatal conductance
European Journal of Forest Research 04/2012; 129(6):1047-1056. · 1.98 Impact Factor
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ABSTRACT: Bioactivity-guided separation of the aqueous methanolic extract of Yucca desmettiana leaves, which in a preliminary screening exhibited significant molluscicidal activity, led to the isolation and structure elucidation of two new steroidal saponins (1 and 2). The structures of desmettianosides A and B, identified as bisdesmosidic furostanol glycosides with six and five sugar units, respectively, were established by detailed spectroscopic analyses of their NMR and MS data. Compounds 1 and 2 exhibited high molluscicidal activity against Biomphalaria alexandrina snails with LC100 values of 6 and 11 mg/L, respectively.
Steroids 03/2012; 77(6):686-90. · 2.83 Impact Factor
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ABSTRACT: Neorogioltriol is a tricyclic brominated diterpenoid isolated from the organic extract of the red algae Laurencia glandulifera. In the present study, the anti-inflammatory effects of neorogioltriol were evaluated both in vivo using carrageenan-induced paw edema and in vitro on lipopolysaccharide (LPS)-treated Raw264.7 macrophages. The in vivo study demonstrated that the administration of 1 mg/kg of neorogioltriol resulted in the significant reduction of carregeenan-induced rat edema. In vitro, our results show that neorogioltriol treatment decreased the luciferase activity in LPS-stimulated Raw264.7 cells, stably transfected with the NF-κB-dependent luciferase reporter. This effect on NF-κB activation is not mediated through MAPK pathways. The inhibition of NF-κB activity correlates with decreased levels of LPS-induced tumor necrosis factor-alpha (TNFα) present in neorogioltriol treated supernatant cell culture. Further analyses indicated that this product also significantly inhibited the release of nitric oxide and the expression of cyclooxygenase-2 (COX-2) in LPS-stimulated Raw264.7 cells. These latter effects could only be observed for neorogioltriol concentrations below 62.5 μM. To our knowledge, this is the first report describing a molecule derived from Laurencia glandulifera with anti-inflammatory activity both in vivo and in vitro. The effect demonstrated in vitro may be explained by the inhibition of the LPS-induced NF-κB activation and TNFα production. NO release and COX-2 expression may reinforce this effect.
Marine Drugs 01/2011; 9(7):1293-306. · 3.85 Impact Factor
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ABSTRACT: Seventeen diterpenes featuring the dolabellane skeleton (1-17) were isolated from the organic extracts of the brown alga Dilophus spiralis. Seven compounds are new natural products (1, 3, 5, 6, 11, 14, 15) and eight are structurally revised (2, 4, 7-10, 12, 13), among which three are reported for the first time from a natural source (4, 9, 10). The structure elucidation and the assignment of the relative configurations of the isolated natural products were based on detailed analyses of their spectroscopic data. The structure of metabolite 10 was confirmed by single-crystal X-ray diffraction analysis, whereas the absolute configurations of compounds 2, 4-10, 12, and 13 were determined using the modified Mosher's method on the semisynthetic product 18 and chemical interconversions. The antibacterial activities of compounds 1-18 were evaluated against six strains of Staphylococcus aureus, including multidrug- and methicillin-resistant variants.
Journal of Natural Products 12/2010; 74(2):213-22. · 3.13 Impact Factor
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ABSTRACT: In this study, we screened eight terpenes isolated from the organic extract of Sphaerococcus coronopifolius for their antifouling activity in order to find possible new sources of non-toxic or less toxic bioactive antifoulants. The anti-settlement activity (EC₅₀) and the degree of toxicity (LC₅₀) of S. coronopifolius metabolites was evaluated using larvae of the cirriped crustacean Amphibalanus (Balanus) amphitrite (cyprids and nauplii) as model organism. For five of eight tested metabolites EC₅₀ was lower than 5 mg/L. The most promising results were observed for bromosphaerol (3), which expressed an EC₅₀ value of 0.23 mg/L, in combination with low toxicity levels (LC₅₀ > 100 mg/L). The therapeutic ratio--an index used to estimate whether settlement inhibition is due to toxicity or other mechanisms--is also calculated and discussed.
Marine Biotechnology 12/2010; 13(4):764-72. · 3.43 Impact Factor
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ABSTRACT: Two naturally occurring diterpenes featuring unprecedented tetracyclic skeletons, ioniols I and II (1 and 2, resp.), along with two previously reported metabolites 3 and 4, were isolated from the organic extract of Sphaerococcus coronopifolius collected from the rocky coasts of Corfu island in the Ionian Sea. The structures of the new natural products, as well as their relative configuration, were elucidated on the basis of extensive spectral analysis, including 2D-NMR experiments. The isolated metabolites were evaluated for their antibacterial activity against a panel of Staphylococcus aureus strains, which included multidrug-resistant (MDR) and methicillin-resistant Staphylococcus aureus (MRSA) strains.
Chemistry & Biodiversity 03/2010; 7(3):666-76. · 1.80 Impact Factor
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ABSTRACT: A novel bromoditerpene methyl ketone (1), two new bromoditerpene alcohols featuring a neodolastane (2), and a bromocorodienol skeleton (3), along with 13 previously reported metabolites (4-16) were isolated from the organic extract of Sphaerococcus coronopifolius collected from the rocky coasts of Corfu island in the Ionian Sea. The structures of the new natural products, as well as their relative stereochemistry, were elaborated on the basis of extensive spectral analysis, including 2D NMR experiments. The absolute stereochemistry of metabolite 3 was determined using the modified Mosher's method. The isolated metabolites were evaluated for their antitumoral activity against four human apoptosis-resistant (U373, A549, SKMEL-28, OE21) and two human apoptosis-sensitive (PC-3, LoVo) cancer cell lines with IC(50) in vitro growth inhibitory concentrations in the range 3-100 microM.
Bioorganic & medicinal chemistry 02/2010; 18(3):1321-30. · 2.82 Impact Factor
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ABSTRACT: Seven new (1-7) and seven previously reported (8-14) halogenated metabolites were isolated from the organic extract of the Brazilian red alga Laurencia catarinensis. The structure elucidation and the assignment of the relative configurations of the new natural products were based on detailed NMR and MS spectroscopic analyses, whereas the structure of metabolite 6 was confirmed by single-crystal X-ray diffraction analysis. The absolute configuration of metabolite 1 was determined using the modified Mosher's method. The in vitro cytotoxicity of compounds 1-14 was evaluated against HT29, MCF7, and A431 cell lines.
Journal of Natural Products 01/2010; 73(1):27-32. · 3.13 Impact Factor
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ABSTRACT: Four new tetracyclic brominated diterpenes, 1-4, were isolated from the organic extract of Sphaerococcus coronopifolius, collected from the rocky coasts of Corfu Island. The structures of the new natural products, as well as their relative configurations, were elucidated on the basis of extensive spectral analyses, including 2D-NMR experiments. The isolated metabolites were evaluated for their antibacterial activity against a panel of bacteria including multidrug-resistant (MDR) and methicillin-resistant Staphylococcus aureus (MRSA) with MIC values in the range of 16-128 microg/ml.
Chemistry & Biodiversity 01/2010; 7(1):186-95. · 1.80 Impact Factor
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ABSTRACT: A ligand-based pharmacophore approach for the prediction of antiestrogenic activity to be used as an in silico screening tool for bioactive compounds including natural products was developed using Catalyst HypoGen. The generated pharmacophore hypothesis (HYPO-7) consisted of five features, namely, one hydrophobic (HY1), two hydrophobic aromatic (HY2), one hydrogen-bond acceptor (HBA), and one hydrogen-bond donor (HBD). HYPO-7 successfully predicted the lack of cytotoxicity of a number of new metabolites isolated from the red alga Laurencia glandulifera. Furthermore, a screening of the Asinex Gold Collection database was performed by coupling HYPO-7 with a docking filtration, which resulted in a restricted set of 12 new scaffolds to be investigated as potential SERMs. The inhibitory activity of these compounds was evaluated in vitro using MCF7 human breast adenocarcinoma cell line. Ten out of the twelve compounds exhibited inhibitory activity with IC(50) values between 26 and 188 microM. This result shows that application of HYPO-7 could assist in the selection of potentially active compounds, thus expediting the hit discovery process.
Journal of Chemical Information and Modeling 10/2009; 49(11):2489-97. · 4.68 Impact Factor
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ABSTRACT: Examination of the digestive and hermaphroditic glands' organic extract of the sea hare Aplysia fasciata yielded 16 metabolites, including eight sesquiterpenes, three diterpenes, and five C(15)-acetogenins. Among them, three sesquiterpenes, 6-hydroxy-1-brasilene (1), epibrasilenol acetate (2), and 6-epi-beta-snyderol (3), one acetogenin, (3Z,9Z)-7-chloro-6-hydroxy-12-oxo-pentadeca-3,9-dien-1-yne (4), and one diterpene, 16-acetoxy-15-bromo-7-hydroxy-9(11)-parguerene (5), are new natural products. The structure elucidation and the assignment of the relative configurations of the isolated natural products were established on the basis of extensive analyses of their spectroscopic data (NMR, MS, IR).
Journal of Natural Products 09/2009; 72(9):1716-9. · 3.13 Impact Factor
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ABSTRACT: Four new 9,11-secosterols (2, 4-6), along with two previously reported ones (1, 3) were isolated from the organic extract of the gorgonian Eunicella cavolini. The structures and relative configurations of the isolated natural products were established on the basis of detailed NMR spectroscopic analysis. Metabolites 1 and 2 were found to strongly inhibit the growth of LNCaP human prostate adenocarcinoma cells and the estrogen-dependent growth of MCF-7 human breast adenocarcinoma cells.
Bioorganic & medicinal chemistry 08/2009; 17(13):4537-41. · 2.82 Impact Factor
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ABSTRACT: The purification of the chloroform extract from the brown invasive macroalga Sargassum muticum, through a series of chromatographic separations, yielded 12 fractions that were tested against strains of bacteria, microalgae, and fungi involved in marine biofilm formation. The chemical composition of four (a, c, g, and k) out of the six fractions that exhibited anti-microfouling activity was investigated. Fraction a contained saturated and unsaturated linear hydrocarbons (C12-C27). Arachidonic acid was identified as the major metabolite in fraction c whereas fraction g contained mainly palmitic, linolenic, and palmitoleic acids. Fraction k was submitted to further purification yielding the fraction kAcaF1e that was composed of galactoglycerolipids, active against the growth of two of the four bacterial strains (Shewanella putrefaciens and Polaribacter irgensii) and all tested fungi. These promising results, in particular the isolation and the activity of galactoglycerolipids, attest the potential of the huge biomass of S. muticum as a source of new environmentally friendly antifouling compounds.
Marine Biotechnology 06/2009; 12(1):52-61. · 3.43 Impact Factor
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ABSTRACT: Acacia mellifera (Vahl) Benth (Leguminosae) is a subtropical medicinal plant that is widely used in traditional African medicines against various diseases such as pneumonia and malaria.
The present study was performed to evaluate the antimicrobial effects of extracts from the stem bark of Acacia mellifera.
The extracts were examined for antibacterial and antifungal activity using the disc-diffusion method against bacterial strains: Streptococcus pneumoniae (ATCC 25923), Pseudomonas aeruginosa (ATCC 27853), Escherichia coli (ATCC 35218), Escherichia coli (ATCC 25922) and Staphylococcus aureus (ATCC 25923) and fungal strains Candida albicans (ATCC 90028), Candida krusei (ATCC 6255), Cryptococcus neoformans (ATCC 6603) and clinical isolates of Microsporum gypseum and Trichophyton mentagrophytes.
Some of these extracts were found to be active against some bacterial and fungal strains and were further fractionated to give 12 pure compounds. The methanolic and methanol:dichloromethane (1:1) extracts exhibited antibacterial and antifungal activity. The two were active against Staphylococcus aureus (ATCC 25923), Microsporum gypseum, and Trichophyton mentagrophytes. Activity guided fractionation led to isolation of two active compounds: 3-(Z)-cis coumaroylbetulin and 30-hydroxylup-20 (29)-en-3beta-ol which were against Staphylococcus aureus (ATCC 25923), Microsporum gypseum, Trichophyton mentagrophytes and Pseudomonas aeruginosa (ATCC 27853).
These results may partly explain and support the use of Acacia mellifera stem barks for the treatment of infectious diseases in traditional Kenya medicine.
Journal of ethnopharmacology 06/2009; 123(1):143-8. · 2.32 Impact Factor
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ABSTRACT: Investigation of minor metabolites in the extracts of the red alga Sphaerococcus coronopifolius collected from the rocky coasts of Corfu Island in the Ionian Sea yielded two new diterpene alcohols, sphaerollanes I, and II (1, 2) featuring neodolabellane skeletons, and the new sphaeroane diterpene alcohol 16-hydroxy-9S*-acetoxy-8-epi-isosphaerodiene-2 (3), along with two previously reported metabolites 4, 5. The structures of the new natural products, as well as their relative stereochemistry, were elucidated on the basis of extensive spectral analysis, including 2D-NMR experiments.
Marine Drugs 02/2009; 7(2):184-95. · 3.85 Impact Factor
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ABSTRACT: Five new C(15) acetogenin en-ynes (1-5) with a rare tetrahydrofuran moiety and a linear biosynthetic precursor (6) were isolated from an organic extract of Laurencia glandulifera, collected from the island of Crete in the south Aegean Sea. The structures of the new natural products, as well as their relative configuration, were established by means of spectroscopic data analysis. The cytotoxicity of the isolated natural products was evaluated against five human tumor cell lines.
Journal of Natural Products 02/2009; 72(2):190-3. · 3.13 Impact Factor
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ABSTRACT: Three new (1, 4, 9) and nine previously reported (2, 3, 5-8, 10-12) 5alpha,8alpha-epidioxysterols were isolated from the organic extracts of the gorgonian Eunicella cavolini and the ascidian Trididemnum inarmatum. The structures and relative configurations of 1-12 were established on the basis of detailed NMR spectroscopic analyses and comparison with the literature. The growth inhibitory effects of 1-12 were evaluated against MCF-7 human breast cancer cells. Compound 1, bearing a cyclopropyl moiety in the side chain, exhibited the highest antiproliferative activity.
Steroids 10/2008; 74(1):73-80. · 2.83 Impact Factor
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ABSTRACT: Four new brominated diterpenes (1, 2, 4, 5), along with two previously reported metabolites (3, 6), were isolated from the organic extract of Sphaerococcus coronopifolius, collected in Palaiokastritsa Bay at the west coast of Corfu Island. The structures of the new products, as well as their relative configuration, were established by means of spectroscopic data analyses, including 2D NMR experiments. The isolated metabolites were evaluated for their antibacterial activity against a panel of multidrug-resistant (MDR) and methicillin-resistant Staphylococcus aureus (MRSA) with MICs in the range 0.5-128 microg/mL.
Journal of Natural Products 08/2008; 71(8):1386-92. · 3.13 Impact Factor
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ABSTRACT: Parnapimarol (1), a new pimarane diterpene, along with nepetaparnone (2) and nepetanudone (3), one new and one previously reported nepetalactone dimer, respectively, were isolated from the dichloromethane extract of the aerial parts of Nepeta parnassica, collected on Mt. Parnassos, Greece. The structures and relative configurations of 1-3 were determined on the basis of their spectroscopic characteristics (1D and 2D NMR, IR, MS). The structure of 2 was confirmed by single-crystal X-ray diffraction analysis. The insecticidal activity of 1-3 against ants and mosquito larvae was also evaluated.
Journal of Natural Products 06/2008; 71(5):926-8. · 3.13 Impact Factor
