Steroids from the soft coral Dendronephthya sp

Fifteen steroids were isolated from the soft coral Dendronephthya sp., of which five are determined as new compounds, namely (22E)-3-O-beta-formylcholest-5,22-diene (1), (22E)-3-O-beta-formyl-24-methyl-cholest-5,22-diene (2), 2-ethoxycarbonyl-2-beta-hydroxy-A-nor-cholest-5-ene-4-one (3), (22E)-2-ethoxycarbonyl-2-beta-hydroxy-A-nor-cholest-5,22-diene-4-one (4), and (22E)-2-ethoxycarbonyl-2-beta-hydroxy-24-mthyl-A-nor-cholest-5,22-diene-4- one (5). 1 and 2 belonged to 3-O-formylated cholesterol analogues, and 3 to 5 are unique ring A-contracted steroids. Their structures were elucidated by extensive 2D NMR in association with IR, MS analysis.     

New 4-methylated and 19-oxygenated steroids from the Formosan soft coral Nephthea erecta

Two new 4-methylated steroids, erectasteroids A and B (1 and 2), six new 19-oxygenated steroids, erectasteroids C-H (3-8) and two known 19-oxygenated steroids (9 and 10) were isolated from the acetone solubles of the Formosan soft coral Nephthea erecta. The structures were elucidated by extensive NMR spectroscopic analysis and their cytotoxicity against selected cancer cells was measured in vitro.     

New 4alpha-methyl steroids from a Chinese soft coral Nephthea sp

Three new 4alpha-methyl steroids, 4alpha-methyl-ergost-7,24(28)-diene-3beta-ol-23-one (1), 4alpha-methyl-ergost-8(14),24(28)-diene-3beta-ol-23-one (2), 4alpha-methyl-ergost-24(28)-en-3beta,11beta-diol-23-one (3), and two new polyoxygenated steroids, ergost-5,25-diene-3beta,24S,28-triol (4), ergost-5,24(28)-diene-3beta,23S-diol (5), along with one known steroid 24-methylencholesterol (6) were isolated from the soft coral Nephthea sp. Their structures including the relative configurations were elucidated by extensive 1D and 2D NMR spectra analysis. The absolute configurations of (4) and (5) were determined by the Mosher's method.     

Cytotoxic ent-kaurene diterpenoids from Isodon phyllostachys

ent-Kaurene diterpenoids, phyllostachysins D-H (1-5), together with nine known compounds, rabdoloxins A-B (6-7), rabdoinflexin B (8), amethystoidin A (9), rabdokunmin D (10), macrocalyxin E (11), 5,7-dihydroxy-4'-hydroxylflavone (12), oleanolic acid (13) and daucosterol (14), were isolated from aerial parts of Isodon phyllostachys. Structures were elucidated on the basis of spectroscopic methods, especially using 2D-NMR spectroscopic analyses. All ent-kaurenoids were tested for their cytotoxic effects against K562 cells. Compound 9 was the most potent with an IC50 value of 0.69 microg/ml.     

Stereumin A-E, sesquiterpenoids from the fungus Stereum sp. CCTCC AF 207024

Five cadinane sesquiterpenoids, named stereumin A (1), B (2), C (3), D (4) and E (5) were isolated from the CHCl(3) extract of the culture broth of the fungal strain CCTCC AF 207024. Based on the sequences at the internal transcribed spacer (ITS) region and partial 28S rDNA, this fungus was identified as a Stereum sp. The structures of the five compounds were elucidated using spectroscopic data from 1D, 2D NMR and HRESIMS experiments, and the structures of 1 and 2 were further confirmed by single-crystal X-ray diffraction analysis. Compounds 1-5 showed nematicidal activities against the nematode Panagrellus redivivus at 400 mg l(-1). Among these five compounds, compounds 3 and 4 killed 84.4% and 94.9% of P. redivivus, respectively in 48 h.     

New cytotoxic steroids from the soft coral Clavularia viridis

Ten new cytotoxic steroids, stoloniferones H-Q (1-10) were isolated from the methylene chloride solubles of the soft coral Clavularia viridis. The structures of the metabolites were elucidated on the basis of spectroscopic (IR, MS, and 1D and 2D NMR) analysis and their cytotoxicity against selected cancer cells was measured in vitro.     

Anti-adipogenic chromone glycosides from Cnidium monnieri fruits in 3T3-L1 cells

Seven new chromone glycosides, monnierisides A (3), B (10), C (11), D (12), E (13), F (15) and G (16) were isolated from Cnidium. monnieri, together with ten known chromone derivatives, undulatoside A (1), cnidimol C (2), saikochromoside A (4), cnidimoside A (5), cnidimoside B (6), 2-methyl-5-hydroxy-6-(2-butenyl-3-hydroxymethyl)-7-(β-d-glucopyranosyloxy)-4H-1-benzopyran-4-one (7), cnidimol D (8), hydroxycnidimoside A (9), umtatin (14) and 6'-hydroxylangelicain (17). The structures of isolated compounds were determined on the basis of spectroscopic analysis including 1D, 2D NMR and HR-MS. Among the compounds isolated, compounds 5, 6, 9 and 10 significantly inhibited adipocyte differentiation as measured by fat accumulation in 3T3-L1 cells using Oil Red O staining.     

Quassinoids from Eurycoma longifolia

Three quassinoids, eurycolactone D (1), eurycolactone E (2) and eurycolactone F (3) were isolated from the roots of Eurycoma longifolia Jack. The structures of 1-3 were elucidated by spectroscopic methods, and that of 3 was further confirmed by X-ray crystallography. The known quassinoids, laurycolactone B (4) and eurycomalactone (5) were also identified.     

细微短足软珊瑚的化学成分研究

本文对采自广西涠洲岛海域细微短足软珊瑚（Cladiellasubtilis）的化学成分进行研究,经理化常数和波谱数据分析,分别鉴定为（20R,24S）-5-烯-21羧基-麦角甾-3β-醇（1）、柳珊瑚甾醇（2）、鲨肝醇（3）及麦角甾-5-烯-3β-醇（4）。对细微短足软珊瑚（Cladiella subtilis）化学成分的研究尚属首次。     

Susceptibility of mice to Trypanosoma evansi treated with human plasma containing different concentrations of apolipoprotein L-1

The aim of this study was to test the susceptibility of mice to Trypanosoma evansi treated with human plasma containing different concentrations of apolipoprotein L-1 (APOL1). For this experiment, a strain of T. evansi and human plasma (plasmas 1, 2, and 3) from 3 adult males clinically healthy were used. In vivo test used 50 mice divided in 5 groups (A to E) with 10 animals in each group. Animals of groups B to E were infected, and then treated with 0.2 ml of human plasma in the following outline: negative control (A), positive control (B), treatment with plasma 1 (C), treatment with plasma 2 (D), and treatment with plasma 3 (E). Mice treated with human plasma showed an increase in longevity of 40.9 ± 0.3 (C), 20 ± 9.0 (D) and 35.6 ± 9.3 (E) days compared to the control group (B) which was 4.3 ± 0.5 days. The number of surviving mice and free of the parasite (blood smear and PCR negative) at the end of the experiment was 90%, 0%, and 60% for groups C, D, and E, respectively. The quantification of APOL1 was performed due to the large difference in the treatments that differed in the source plasma. In plasmas 1, 2, and 3 was detected the concentration of 194, 99, and 115 mg/dl of APOL1, respectively. However, we believe that this difference in the treatment efficiency is related to the level of APOL1 in plasmas.     

Functional Gene-Guided Discovery of Type II Polyketides from Culturable Actinomycetes Associated with Soft Coral Scleronephthya sp

Compared with the actinomycetes in stone corals, the phylogenetic diversity of soft coral-associated culturable actinomycetes is essentially unexplored. Meanwhile, the knowledge of the natural products from coral-associated actinomycetes is very limited. In this study, thirty-two strains were isolated from the tissue of the soft coral Scleronephthya sp. in the East China Sea, which were grouped into eight genera by 16S rDNA phylogenetic analysis: Micromonospora, Gordonia, Mycobacterium, Nocardioides, Streptomyces, Cellulomonas, Dietzia and Rhodococcus. 6 Micromonospora strains and 4 Streptomyces strains were found to be with the potential for producing aromatic polyketides based on the analysis of KS(α) (ketoacyl-synthase) gene in the PKS II (type II polyketides synthase) gene cluster. Among the 6 Micromonospora strains, angucycline cyclase gene was amplified in 2 strains (A5-1 and A6-2), suggesting their potential in synthesizing angucyclines e.g. jadomycin. Under the guidance of functional gene prediction, one jadomycin B analogue (7b, 13-dihydro-7-O-methyl jadomycin B) was detected in the fermentation broth of Micromonospora sp. strain A5-1. This study highlights the phylogenetically diverse culturable actinomycetes associated with the tissue of soft coral Scleronephthya sp. and the potential of coral-derived actinomycetes especially Micromonospora in producing aromatic polyketides.     

Polyhydroxylated steroids from the soft coral Sinularia dissecta

A repeated silica gel column chromatography followed by HPLC purification on the methanol extract of marine soft coral Sinularia dissecta, resulted in the isolation of fifteen polyhydroxylated steroids (1-15), involving six new C-18 functionalized steroids, 3beta-acetoxy-1alpha,11alpha-dihydroxygorgost-5-en-18-oic acid (1), gorgost-5-en-1alpha,3beta,11alpha,18-tetrol (2), 18-acetoxy-1alpha,3beta,11alpha-trihydroxygorgost-5-ene (3), 24(S)-3beta-acetoxy-1alpha, 11alpha-dihydroxyergost-5-en-18-oic acid (4), 24(S)-ergost-5-en-1alpha,3beta,11alpha,18-tetrol (5), and dissectolide (6). The structures of the new compounds were determined on the basis of extensive spectroscopic data (IR, MS, (1)H and (13)C NMR, HMQC, HMBC, and NOESY) analysis. Compound 6 was found as an unusual sterol bearing a lactone functionality.     

Thelephantins D-H: five p-terphenyl derivatives from the inedible mushroom Thelephora aurantiotincta

Five p-terphenyl derivatives named thelephantins D-H (1-5) together with nine known compounds, thelephantins A-C (6-8), ganbajunin E (9), p-hydroxylbenzoic acid (10), ganbajunin C (11), thelephorin A (12), 2-O-methylatromentin (13) and atromentin (14), were isolated from the methanolic extract of fruit bodies of the Thelephoraceous Basidiomycete Thelephora aurantiotincta. Their structures were elucidated by high-resolution MS, 2D NMR, IR and UV spectroscopic analysis.     

Phenylpropanoid glucosides from leaves of Coussarea hydrangeifolia (Rubiaceae)

Phenylpropanoid glycosides, 1'-O-benzyl-alpha-L-rhamnopyranosyl-(1'-->6')-beta-D-glucopyranoside (1) and alpha-L-xylopyranosyl-(4'-->2')-(3-O-beta-D-glucopyranosyl)-1'-O-E-caffeoyl-beta-D-glucopyranoside (2), together with the known derivatives, 1,6-di-O-caffeoyl-beta-D-glucopyranoside (3), 1-O-(E)-caffeoyl-beta-D-glucopyranoside (4) and 1-O-(E)-feruloyl-beta-D-glucopyranoside (5), were isolated from leaves of Coussarea hydrangeifolia. Their structures were determined by IR, HRESIMS, and 1D and 2D NMR experiments, and their antioxidant activities, evaluated by assaying the free radical scavenging capacity using the DPPH (1,1-diphenyl-2-picrylhydrazyl) radical as substrate. The antioxidant activities of 3 and 4 (IC50 values of 15.0 and 19.2 microM, respectively) were comparable to that of the standard positive control caffeic acid, whilst 2 and 5 were only weakly active and 1 was inactive.     

C(15) Acetogenins from the red alga Laurencia obtusa.

Four C(15) acetogenins, 13-epilaurencienyne (3Z) (1), 13-epipinnatifidenyne (3E) (2), (3E, 6S(*), 7R(*), 9S(*), 10S(*), 12R(*))-9-chloro-13-bromo-6:12-epoxy-7, 10-diacetoxypentadec-3-en-1-yne (3), (3Z, 6S(*), 7R(*), 9S(*), 10S(*), 12R(*))-9-chloro-13-bromo-6:12-epoxy-7, 10-diacetoxypentadec-3-en-1-yne (4), along with the known 13-epilaurencienyne (3E) (5), have been isolated from the organic extract of the red alga Laurencia obtusa, collected in the Aegean Sea, Greece. The structures of the new natural products, as well as their relative stereochemistry, were established by means of spectral data analysis, including 2D NMR spectroscopic experiments. Some of the new metabolites exhibited significant insecticidal activity.     

Leishmanicidal cycloartane-type triterpene glycosides from Astragalus oleifolius

Two new cycloartane-type glycosides oleifoliosides A (1) and B (2) were isolated from the lower stem parts of Astragalus oleifolius. Their structures were identified as 3-O-[beta-xylopyranosyl-(1 --> 2)-alpha-arabinopyranosyl]-6-O-beta-xylopyranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxycycloartane and 3-O-[beta-xylopyranosyl-(1 --> 2)-alpha-arabinopyranosyl]-6-O-beta-glucopyranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxycycloartane, respectively, by means of spectroscopic methods (IR, 1D and 2D NMR, ESI-MS). Three known cycloartane glycosides cyclocanthoside E (3), astragaloside II (4) and astragaloside IV (5) were also isolated and characterized. All five compounds were evaluated for in vitro trypanocidal, leishmanicidal and antiplasmodial activities as well as their cytotoxic potential on primary mammalian (L6) cells. Except for the compound 5, all compounds showed notable growth inhibitory activity against Leishmania donovani with IC50 values ranging from 13.2 to 21.3 microg/ml. Only weak activity against Trypanosoma brucei rhodesiense was observed with the known compounds astragaloside II (4, IC50 66.6 microg/ml) and cyclocanthoside E (3, IC50 85.2 microg/ml), while all compounds were inactive against Trypanosoma cruzi and Plasmodium falciparum. None of the compounds were toxic to mammalian cells (IC50's > 90 microg/ml). This is the first report of leishmanicidal and trypanocidal activity of cycloartane-type triterpene glycosides.     

Alkaloids from Portulaca oleracea L

Five alkaloids (oleraceins A, B, C, D and E) were isolated from Portulaca oleracea L., and their structures determined by spectroscopic methods as 5-hydroxy-1-p-coumaric acyl-2,3-dihydro-1H-indole-2-carboxylic acid-6-O-beta-D-glucopyranoside, 5-hydroxy-1-ferulic acyl-2,3-dihydro-1H-indole-2-carboxylic acid-6-O-beta-D-glucopyranoside, 5-hydroxy-1-(p-coumaric acyl-7'-O-beta-D-glucopyranose)-2,3-dihydro-1H-indole-2-carboxylic acid-6-O-beta-D-glucopyranoside, 5-hydroxy-1-(ferulic acyl-7'-O-beta-D-glucopyranose)-2,3-dihydro-1H-indole-2-carboxylic acid-6-O-beta-D-glucopyranoside and 8,9-dihydroxy-1,5,6,10b-tetrahydro-2H-pyrrolo[2,1-a]isoquinolin-3-one, respectively.     

Immune depression in Rhodnius prolixus by seco-steroids, physalins

A comparative study of the effects of physalins, seco-steroidal substances of Physalis angulata (Solanaceae), on the immune reactions of R. prolixus was carried out. Ecdysis and mortality were not affected by treatment with physalins B, D, F or G (1-10 microg/ml of blood meal). R. prolixus larvae fed with blood containing physalins and inoculated with 1 microl of Enterobacter cloacae beta12 (5 x 10(3)/insect) exhibited mortality rates three times higher than controls. The insects treated with physalin B, and F (1 microg/ml) and inoculated with E. cloacae beta12 showed significant differences on lysozyme activity in the hemolymph compared to untreated insects. Furthermore, physalin D (1 microg/ml) significantly reduced the antibacterial activity. Concerning cellular immune reactions, all insects treated with physalins (1 microg/ml), exhibited drastic reductions in the quantity of yeast cell-hemocyte binding and subsequent internalization. Insects inoculated with bacteria and treated with physalins B, F and G showed reductions of microaggregate formation but physalin D did not. Physalins B and F also reduced total hemocyte count in the hemolymph. These results suggest that, in different ways, probably due to their different chemical structures, physalin B, D, F and G are immunomodulatory substances for the bloodsucking insect, R. prolixus.     

Anti-staphylococcal acylphloroglucinols from Hypericum beanii

As part of an ongoing project to investigate the anti-staphylococcal properties of the Hypericum genus, an acylphloroglucinol, 1,5-dihydroxy-2-(2'-methylpropionyl)-3-methoxy-6-methylbenzene (1), was isolated from the dichloromethane extract of the aerial parts of H. beanii (Guttiferae), together with a minor related acylphloroglucinol 1,5-dihydroxy-2-(2'-methylbutanoyl)-3-methoxy-6-methylbenzene (2) as a mixture in a 5:2 ratio. The known compounds 1,7-dihydroxyxanthone (3), stigmasterol, catechin and shikimic acid were also isolated from this plant. The structures of the compounds were characterized by extensive 1- and 2D NMR spectroscopy and mass spectrometry. The minimum inhibitory concentration (MIC) values the acylphloroglucinol mixture and (3) against a panel of multidrug-resistant strains of Staphylococcus aureus ranged from 16-32 microg/ml to 128-256 microg/ml, respectively.