Records of Natural Products Articles

• A new pyridine-containing natural product, kitasatodine (1), and a new sesquiterpene, kitasatopenoid (2), together with a known cycloheximide (3) were isolated from the ethyl acetate extract of the strain H6549 (Kitasatospora sp.), which was isolated from dipterocarp forest of Kepong Kuala Lumpur in Malaysia. Their structures were established by spectroscopic methods including 1D and 2D-NMR experiments and HR-Q-TOF-MS. In addition, compounds 1and 2 showed moderate cytotoxicity against HeLa and HepG-2 cell lines.

Diarylheptanoids, as a class of structurally distinctive compounds with notable biological activities, have been of increasing interest in the past decades. We previously reviewed 307 such materials occur in nature. This review collected the inadvertently missing literature in our previous paper along with the lasted researches on this field, and 102 diarylheptanoids have been retrieved, in addition to their distributions, physiological activities and 13C-NMR spectral data. 72 references are cited.

 The samples of the hazelnut, peanut, pistachio, almond, walnut, chestnut, pumpkin seed and sunflower seed were collected from Turkey. The fatty acid compositions of Turkish nut and seed oils were analyzed by Gas Chromatography (GC) were determined. The antioxidant activity of the samples was assessed by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging capacity assay toward BHT and Vitamin C. Retinol and a -tocopherol were analyzed using High-Pressure Liquid Chromatography with UV Detector (HPLC-UV). The antimicrobial and antifungal activities of Turkish nut and seeds were evaluated using the disk diffusion method toward 9 bacteria and 5 yeasts. The nut and seeds showed strong antimicrobial activity against the test organisms. Spectroscopic determination of minerals (Calcium, magnesium, potassium, sodium, iron, copper, manganese, selenium, zinc, chromium, aluminum) of nuts and seeds was performed with inductively coupled plasma-atomic emission spectrometer (ICP-AES). The calorie values of samples were measured using a Bomb Calorimeter.

Chemical composition of the essential oil obtained from the aerial parts of Scrophularia amplexicaulis Benth. was analyzed, for the first time, by the gas chromatography/mass spectrometry (GC-MS) and gas chromatography/flame ionization detection (GC-FID). A total yield of 3 mg of essential oil per100 g of plant dry mass was obtained, and 27 compounds were identified, representing 97. 7 % of total oil. The essential oil were characterized by a high content of oxygenated monoterpenes and phenolic derivatives. The main constituents were eugenol (53.8%), eugenol acetate (24.5%), b -caryophyllene (5.7%), caryophyllene oxide (6.4%) and aromadendrene oxide II (2.1%). The antimicrobial activity of the essential oil was tested against Staphylococcus aureus using the well diffusion method, and t he free-radical-scavenging activity was assessed by the 2,2-diphenyl-picryl-hydrazyl (DPPH) assay .

The extracts of various marine sponges (Agelas oroides and Axinella damicornis, Axinella cannabina, Ircinia spinulosa, I. fasciculata, and I. variabilis, Dysidea avara, and Sarcotragus spinulosus) collected from different spots of the Turkish cost of the Mediterranean Sea have been evaluated for their antibacterial, antifungal, 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging, and acetylcholinesterase (AChE) inhibitory activities. Three compounds (oroidin, 4,5-dibromopyrrol-2-carboxylic acid, and 25-hydroxy-24-methylcholesterol) were isolated from A. oroides and tested in the same manner. The sponge extracts showed notable antimicrobial and anti-AChE activity and low DPPH scavenging activity. Oroidin was found to have moderate anti-AChE and strong radical scavenging activities. The results demonstrated that the sponge extracts exerted a variable degree of antibacterial, anti-radical, and anti-AChE activity, whereas they seemed to have similar antifungal effect. Our findings point out to the fact that the collection site has an important influence on bioactivity of the sponges.

Five flavonol glycosides, kaempferol 3,7-di-O- α -L-rhamnopyranoside (1) , isorhamnetin 3,7-di-O- α -L-rhamnopyranoside (2) , kaempferol 3-O- β -D-glucopyranoside-7-O- α -L-rhamnopyranoside (3) , isorhamnetin 3-O- β -D-glucopyranoside-7-O- α -L-rhamnopyranoside (4), Kaempferol 3-O- β -xylopyranosyl-(1'''→2'')-O- α -L-rhamnopyranoside-7-O- α -L-rhamnopyranoside (5), have been isolated from the aerial parts of Reseda arabica. Their structures were established on the basis of physical and spectroscopic analysis, and by comparison with the literature data.

 The chemical composition of the essential oils of Perymenium grande Hemsl. var nelsonii (Robins. & Greenm.) Fay (Asteraceae) growing wild in Costa Rica was analyzed by capillary GC-FID and GC-MS. One hundred and two and one hundred and seven compounds were identified in the leaf and branch oils, respectively, corresponding to about 94.9% and 79.3% of the total amount of the oils. The leaf oil consists mainly of sesquiterpene hydrocarbons (50.3%) and monoterpene hydrocarbons (33.8%). The major components of the leaf oil were b -caryophyllene (30.5%), b -pinene (12.4%), germacrene D (10.0%), b -phellandrene (9.8%) and a -pinene (8.9%). The branch oil consists mainly of sesquiterpene hydrocarbons (38.3%), monoterpene hydrocarbons (21.6%) and oxygenated sesquiterpenes (20.4%). The major components of the branch oil were a -isocomene (13.8%), a -pinene (7.4%), b -isocomene (5.2%), b -pinene (4.3%) and b -caryophyllene (4.3%). This is the first report of the chemical composition of the essential oils obtained from this species.

In this study, narciprimine and arolycoricidine were isolated from G. rizehensis Stern (Amaryllidaceae). The structures of the alkaloids were elucidated by spectroscopic methods (1D NMR, EI-MS). Due to the previous reports on anti-cancer activity of this group of alkaloids, we investigated their effects on DNA topoisomerase reactions, which are known as the cellular targets of a number of chemotherapeutical drugs. The results revealed that arolycoricidine and narciprimine were effective in both type I and type II DNA topoisomerase reactions in a dose-dependent manner. Topoisomerase-interfering ability of these alkaloids partially correlated with cytostaticity assays, using HeLa (cervix adenocarcinoma), MCF7 (breast adenocarcinoma) and A431 (skin epidermoid carcinoma) cells. Our results are discussed in relation to the potential significance of these alkaloids in the course of drug-development studies.

Six coumarins (1-6) and twelve alkaloids (7-18) were isolated from the roots of Clausena excavata. Their structures were elucidated on the basis of spectroscopic methods. This is the first report on the isolation of compounds 1, 7 and 17 from C. excavata. Compound 1 is also the first example of an unsymmetrical dimer coumarin isolated from Clausena species. The completed assignment of 13C NMR spectral data of 1 as well as HMBC spectral data is also reported here for the first time. Compounds 2-7, 11-16 and 18 were evaluated for their cytotoxicity against three human cancer cell lines, oral cavity cancer (KB), breast cancer (MCF7) and small cell lung cancer (NCI-H187). The results showed that compounds 4, 11 and 18 exhibited highest cytotoxicity against KB, MCF7 and NCI-H187 cell lines with IC 50 values of 5.95, 3.76 and 5.65 µg/mL, respectively.

Ptilostemon greuteri Raimondo & Domina is described as a new species and its growth is limited to the area of the province of Trapani. Essential oils of aerial parts of P. greuteri were analized by gas chromatography-mass spectrometry (GC-MS). The analysis of acetonic extract of aerial parts led to identification of triterpenes components: α-amyrin, β-amyrin, α-amyrin acetate, β-amyrin acetate, lupeol, lupeol acetate and taraxasterol. CC and preparative TLC of acetonic extracts has yielded lignan lactone and a sesquiterpene lactone that have been isolated previously from other Ptilostemon species.

The aim of the study was to evaluate the antioxidant activity of extracts of aerial tissues (i.e. flowers, leaves, stems, twigs and berries) of the mistletoe Loranthus europaeus that grow on oak trees in a natural forest, in the mainland of Greece. Total phenolic content and antioxidant potential of aerial issues of L. europaeus was evaluated by the Folin - Ciocalteu method , the Ferric r educing antioxidant power assay , the free radical DPPH · scavenging and the Co(II)/EDTA induced luminol plateau chemiluminescence assay. Extracts of twigs and stems of L. europaeus exhibited higher antioxidant activity in comparison to that of fruits, leaves and flowers.

The aim of the study was to evaluate the antioxidant activity of extracts of aerial tissues (i.e. flowers, leaves, stems, twigs and berries) of the mistletoe Loranthus europaeus that grow on oak trees in a natural forest, in the mainland of Greece. Total phenolic content and antioxidant potential of aerial issues of L. europaeus was evaluated by the Folin - Ciocalteu method , the Ferric r educing antioxidant power assay , the free radical DPPH · scavenging and the Co(II)/EDTA induced luminol plateau chemiluminescence assay. Extracts of twigs and stems of L. europaeus exhibited higher antioxidant activity in comparison to that of fruits, leaves and flowers.

 A chemical investigation of marine sponge Jaspis stellifera, collected from South China Sea, led to the isolation of two new compounds, Jaspiferin A and B (1-2), and six known compounds, gibepyrone F (3) , p- hydroxy benzaldehyde (4) , 3-Indole-3-aldehyde (5) , Thymine (6) , 24(28)-dehydroaplysterol (7) , (25s)-26- methylene-cholest-4-en-3-one (8). Their structures were determined by extensive spectroscopic analysis in association with physical and chemical properties, as well as comparison of their spectral data with these reported in literatures. The biogenetic transformation of compound 2was also speculated.

Water-distilled essential oils from aerial parts of Tanacetum densum (L.) Heywood ssp. eginense Heywood, from Turkey was analysed by GC and GC-MS. T. densum ssp. eginense flower, stem and leaf oils were characterized with camphor (30.9% , 25.7%, 27.7%), 1,8-Cineole (12.4% flower oil), camphene (10.6%, %7.0, flower and leaf oils), bornyl acetate, (9.4%, 11.8%, stem and leaf oils), α-pinene (7.0%, %5.3, flower and leaf oils ), borneol (5.1%, 5.2%, stem and leaf oils), neodihydrocarveol (5.1%, flower oil). An unidentified compound was also present in flower, stem and leaf oils (11.5%, 27.2%, 20.5%). A comparison is done with the previous investigations on the other subspecies of T. densum and the differences were investigated. Flower and stem oils did not show any significant activity to the tested microorganisms when compared to positive control chloramphenicol. Flower and stem oils both showed cytotoxicity to Vibrio fischeri.