ALBERT

Description: A bioassay-guided approach was used to identify defense compounds that are present on the surface of Zostera marina and which inhibit settlement of microfoulers at natural concentrations. Moderately polar eelgrass surface extracts inhibited the settlement of seven marine bacteria and one yeast that originated from non-living substrata. In contrast, five other bacterial strains that had been directly isolated from eelgrass surfaces were all insensitive, which suggested a selective effect of surface metabolites on the microbial communities present on eelgrass. Bioassay-guided isolation of active compounds from the extracts in combination with UPLC-MS and 1H-NMR spectroscopy resulted in the identification of rosmarinic acid, luteolin-7-sulfate and diosmetin-7-sulfate or its isomer chrysoeriol-7-sulfate. All three compounds are nontoxic repellents, as they did not inhibit bacterial growth, but prevented bacterial settlement in a dose-dependent manner. Between 15.6 and 106.8 μg ml−1 of rosmarinic acid were present on the eelgrass surface, enough for half maximal settlement inhibition of bacteria.

Description: Abstract: Context: Some Ajuga L. (Lamiaceae) species are traditionally used for the treatment of malaria, as well as fever, which is a common symptom of many parasitic diseases. Objective: In the continuation of our studies on the identification of antiprotozoal secondary metabolites of Turkish Lamiaceae species, we have investigated the aerial parts of Ajuga laxmannii. Materials and methods: The aerial parts of A. laxmannii were extracted with MeOH. The H2O subextract was subjected to polyamide, C18-MPLC and SiO2 CCs to yield eight metabolites. The structures of the isolates were elucidated by NMR spectroscopy and MS analyses. The extract, subextracts as well as the isolates were tested for their in vitro antiprotozoal activities against Plasmodium falciparum, Trypanasoma brucei rhodesiense, T. cruzi and Leishmania donovani at concentrations of 90–0.123 μg/mL. Results: Two iridoid glycosides harpagide (1) and 8-O-acetylharpagide (2), three o-coumaric acid derivatives cis-melilotoside (3), trans-melilotoside (4) and dihydromelilotoside (5), two phenylethanoid glycosides verbascoside (6) and galactosylmartynoside (7) and a flavone-C-glycoside, isoorientin (8) were isolated. Many compounds showed moderate to good antiparasitic activity, with isoorientin (8) displaying the most significant antimalarial potential (an IC50 value of 9.7 μg/mL). Discussion and conclusion: This is the first report on the antiprotozoal evaluation of A. laxmannii extracts and isolates. Furthermore, isoorientin and dihydromelilotoside are being reported for the first time from the genus Ajuga.

Description: Volatile constituents of various solvent extracts (n-hexane, CH2Cl2, H2O) of 15 different organs (leaves, flowers, fruits) of five Rhododendron species (Ericaceae) growing in Turkey were trapped with headspace solid-phase microextraction (HS-SPME) technique and analyzed by GC-MS. A total of 200 compounds were detected and identified from organic extracts, while the water extracts contained only traces of few volatiles. The CH2Cl2 extract of the R. luteum flowers was found to exhibit the most diverse composition: 34 compounds were identified, with benzyl alcohol (16.6%), limonene (14.6%) and p-cymene (8.4%) being the major compounds. The CH2Cl2-solubles of R. x sochadzeae leaves contained only phenyl ethyl alcohol. This study indicated appreciable intra-specific variations in volatile compositions within the genus. Different anatomical parts also showed altered volatile profiles. This is the first application of HS-SPME-GC-MS on the volatiles of Rhododendron species.

Description: Using thin-layer chromatography (TLC) bioautography, a total of 58 extracts from various organs (aerial parts, leaves, flowers, fruits, roots) of 16 Turkish plants were tested for their antibacterial, antifungal, acetylcholinesterase inhibitory, antioxidant, and radical scavenging activities. The hexane, CHCl3/CH2Cl2, water, and total MeOH extracts were used. No activity was observed against two Gram-negative bacteria (Escherichia coli and Pseudomonas aureginosa) and the yeast Candida albicans. However, 23 plant extracts, mostly the CHCl3/CH2Cl2 and H2O-solubles, inhibited the growth of all five Gram-positive bacteria tested, Micrococcus luteus, Bacillus subtilis, Bacillus cereus, Staphylococcus aureus, and Staphylococcus epidermidis. Of the active extracts, the CHCl3-soluble of the roots of Putoria calabrica (L. fil) DC (Rubiaceae) displayed the highest antibacterial potential. The majority of the CHCl3/CH2Cl2 crude extracts also appeared to inhibit acetylcholinesterase on TLC plates at 100 µg/spot concentration. Particularly active samples were the middle polarity extracts (CHCl3/CH2Cl2) of the leaves of Rhododendron smirnovii Trautv., R. ponticum L., and R. ungernii Trautv. (Ericaceae). β-Carotene, β-carotene/linoleic acid mixture, and 2,2-diphenyl-l-pieryhydrazyl (DPPH) solutions sprayed onto TLC plates were used for detecting antioxidant and radical scavenging properties of the crude extracts. Antioxidant and radical scavenging activities were found to be predominant in highly polar extracts. The water-solubles of all Rhododendron (Ericaceae) and Phlomis (Lamiaceae) species presented the most significant activity.

Description: From the methanolic extract ofthe underground parts of Globularia orientalis, a new antioxidant sugar ester was isolated. The structure ofthe new compound, globularitol (1), was identified as 6-O-feruloyl-ß-d-glucopyranosyl-(156)-glucitol by spectroscopic methods (1D and 2D NMR, ESI- and FAB-MS) and confirmed by chemical means.

Description: A detailed chemical analysis of a Philippine marine sponge Smenospongia sp. has been performed. This study yielded four new metabolites, 5-bromo-l-tryptophan (1), 5-bromoabrine (2), 5,6-dibromoabrine (3) and 5-bromoindole-3-acetic acid (4). The pyrroloiminoquinone alkaloid, makaluvamine O (5) as well as 5,6-dibromotryptamine (6), aureol (7) and furospinulosin 1 (8) were also isolated. Although 1 and 4 have been synthesized previously, this is the first report on the isolation of these compounds from a natural source. The furanosesterterpene furospinulosin 1 (8) was obtained for the first time from the genus Smenospongia. The structures of all compounds were established by spectroscopic methods (UV, IR, 1D and 2D NMR, MS, [α]D). The cytotoxic potential of 1Ð8 was evaluated in a panel of isogenic HCT-116 human colon tumor cell lines.