Band 73, Heft 1-2

Three new coumarin types were isolated from the aerial parts of the wild medicinal plant Ammi majus , which was collected from western Asia (Saudi Arabia), including pyrano coumarin, namely, 5-isobutylcoumarin-6-C-glucoside (1) ; furanocoumarin, namely, 6,7,9-Trimethoxy-3-(8′-methoxy-2′-oxo-2H-chromen-3-yl)-2H-furo[3,2-g]chromen-2(3H)-one (2) ; and pyrone coumarin, namely, 6-hydroxy-3-(2-hydroxypropyl)-7-methoxy-4 methyl coumarin (3) . The structures were determined by spectroscopic methods, mainly 1D- and 2D-NMR. In vitro cytotoxicity was evaluated by 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyl-tetrazolium bromide (MTT) assay. The results of cytotoxicity depending on their structure features showed that compound 3 had high activity on different cell lines, while compound 1 showed no activity against HCT116. Compound 2 had high activity towards HCT116 cell line.

A new pseudoguaiane-type sesquiterpene named litopharbol ( 1 ) was isolated from the methanolic extract of the Red Sea soft coral Litophyton arboreum , along with known sesquiterpenoids alismol ( 2 ), alismorientol B ( 3 ), teuhetenone A ( 4 ), and calamusin I ( 5 ); steroid, 24-methyl-cholesta-5,24(28)-diene-3β-ol ( 6 ), alkyl glyceryl ether, chimyl alcohol ( 7 ); sphingolipid, erythro- N -dodecanoyl-docosasphinga-(4 E ,8 E )-dienine ( 8 ); and nitrogenous bases, thymine ( 9 ) and thymidine ( 10 ). The structures were determined on the basis of nuclear magnetic resonance (NMR) spectroscopic (1D and 2D NMR data including heteronuclear single quantum coherence spectroscopy, heteronuclear multiple-bond correlation spectroscopy, and nuclear Overhauser effect spectroscopy) and mass spectrometric analyses. Compounds 1–5 were explored for antimicrobial activity and cancer cell line sensitivity tests. Compound 1 exhibited antibacterial activity against Bacillus cereus with a minimum inhibition concentration of 1.8 μg/mL, whereas compound 3 showed significant potent cytotoxic effect against MCF-7 (breast cancer cells) with IC 50 4.32 μM.

With the increase in human demands for energy, purpose-grown woody crops could be part of the global renewable energy solution, especially in geographical regions where plantation forestry is feasible and economically important. In addition, efficient utilization of woody feedstocks would engage in mitigating greenhouse gas emissions, decreasing the challenge of food and energy security, and resolving the conflict between land use for food or biofuel production. This review compiles existing knowledge on biotechnological and genomics-aided improvements of biomass performance of purpose-grown poplar, willow, eucalyptus and pine species, and their relative hybrids, for efficient and sustainable bioenergy applications. This includes advancements in tree in vitro regeneration, and stable expression or modification of selected genes encoding desirable traits, which enhanced growth and yield, wood properties, site adaptability, and biotic and abiotic stress tolerance. Genetic modifications used to alter lignin/cellulose/hemicelluloses ratio and lignin composition, towards effective lignocellulosic feedstock conversion into cellulosic ethanol, are also examined. Biotech-trees still need to pass challengeable regulatory authorities’ processes, including biosafety and risk assessment analyses prior to their commercialization release. Hence, strategies developed to contain transgenes, or to mitigate potential transgene flow risks, are discussed.

Three new glucosylceramides (GluCers) named malusides I–III ( 1–3 ) were isolated from apple (cultivars of Malus domestica ) pomace (fruit material remaining after juice extraction). An unusual oxo/hydroxy group pattern within the sphingadienine (d18:2) type sphingoid base was observed. All compounds contained the same α -hydroxylated fatty acid (h16:0) and a β -D-glucose moiety. Their structures were assigned on the basis of one- and two-dimensional (1D and 2D) nuclear magnetic resonance (NMR) spectroscopic analyses and mass spectrometry (MS) measurements.

A comparative investigation of n-hexane soluble compounds from aerial parts of dandelion ( Taraxacum officinale Weber ex F.H. Wigg.) collected during different vegetative stages was carried out. The GC-MS analysis of the n-hexane (unpolar) fraction showed the presence of 30 biologically active compounds. Phytol [14.7% of total ion current (TIC)], lupeol (14.5% of TIC), taraxasteryl acetate (11.4% of TIC), β-sitosterol (10.3% of TIC), α-amyrin (9.0% of TIC), β-amyrin (8.3% of TIC), and cycloartenol acetate (5.8% of TIC) were identified as the major components in n-hexane fraction. The unpolar fraction exhibited promising antioxidant activity – 46.7 mmol Trolox equivalents/g extract (determined by 1,1-diphenyl-2-picrylhydrazyl method). This fraction demonstrated insignificant antimicrobial activity and can be used in cosmetic and pharmaceutical industries.

In the course of our screening program for new bioactive compounds, a naturally new 18-membered macrolide antibiotic, N -acetylborrelidin B ( 1 ) along with borrelidin ( 2 ) were obtained from the marine Streptomyces mutabilis sp. MII. The strain was isolated from a sediment sample collected in the Red Sea at the Hurghada Coast and characterized taxonomically. Additional nine diverse bioactive compounds were reported: 6-prenyl-indole-3-acetonitrile ( 3 ), sitosteryl-3 β - d -glucoside, campesterol, ferulic acid, linoleic acid methyl ester, linoleic acid, N -acetylanthranilic acid, indole 3-acetic acid methyl ester, indole 3-carboxylic acid, and adenosine. Structure 1 was confirmed by in-depth NMR studies and by mass spectra, and comparison with related literature data. The antimicrobial activity of the strain extract and compounds 1 and 2 were studied using a panel of pathogenic microorganisms. The in vitro cytotoxicity of compounds 1 and 2 as well as the crude extract were tested against the human cervix carcinoma cell line (KB-3-1).

(9 Z )-Methyl 4-dihydrotrisporate B and (9 Z )-methyl trisporate B, pheromones of Zygomycetes fungi, have been synthesized using Stille cross-coupling from previously described cyclohexenone precursors. Conducting the coupling without protection groups allowed for a short and stereospecific synthesis route of the late trisporoids. Stability studies for both the compounds revealed (9 Z )-methyl trisporate B to be very unstable against UV irradiation.

While the chemical composition of leaf and stem bark essential oils of the Chinese cinnamon, Cinnamomum cassia (L.) J. Presl, has been well investigated, little is known about the volatilom of its buds, which appeared recently on German markets. Soxhlet extracts of the commercial samples were prepared, fractionated using silica gel and characterised by gas chromatography-flame ionisation detector (GC-FID) for semi-quantification, by gas chromatography-mass spectrometry (GC-MS) for identification and by GC-FID/olfactometry for sensory evaluation. Cinnamaldehyde was the most abundant compound with concentrations up to 40 mg/g sample. In total, 36 compounds were identified and 30 were semi-quantified. The extracts contained mostly phenylpropanoids, mono- and sesquiterpene hydrocarbons and oxygenated derivatives. Because of the high abundance of cinnamaldehyde, the aldehyde fraction was removed from the extracts by adding hydrogen sulphite to improve both the detection of trace compounds and column chromatography. The aldehyde fraction was analysed by GC-MS separately. The highest flavour dilution factor of 316 was calculated for cinnamaldehyde. Other main sensory contributors were 2-phenylethanol and cinnamyl alcohol. This report provides the first GC-olfactometry data of a plant part of a Cinnamomum species. The strongly lignified C. cassia buds combine a high abundance of cinnamaldehyde with comparably low coumarin concentrations (<0.48 mg/g), and provide a large cinnamaldehyde depot for slow release applications.

Algae collection and chlorophyll extraction are two troublesome steps in the traditional methods used for the determination of chlorophyll concentration in natural water. A new method was established in this study for fast collection and extraction of chlorophyll. Based on our results, the optimum centrifugation condition for collecting algae was determined as: 5000 g for 15 min at 4 °C, and the optimum dilution ratio of dimethyl sulfoxide: 90% acetone was 1:4. The specific steps were as follows: the algae in water samples were collected by centrifugation at 5000 g at 4 °C for 15 min. The precipitated algae were suspended with 2 mL DMSO. Then the sample was transferred to a 15 mL centrifuge tube, and the tube was incubated at 65 °C for 1–2 h in the dark until the sample turned white. After cooling, the chlorophyll extract was diluted with 8 mL 90% acetone, before centrifugation at 5000 g for 5 min. The absorbance values of the supernatants at 750, 664, 647 and 630 nm were used for the calculation of chlorophyll concentrations by the trichromatic equations. This new method saved the filter cost, simplified the extraction process, improved the algae acquisition efficiency, and accelerated the chlorophyll extraction rate.

The synthesis of hydroxyflavone derivatives is described. The acyl derivatives of 3-, 6-, 7-hydroxyflavones (compounds 2 , 4 , 6 , respectively) and chrysin (5,7-dihydroxyflavone, 7 ) were obtained in high yields and evaluated in vitro for their cytotoxic activity against several cancer cell lines of different origin: MCF-7 (breast cancer), A549 (nonsmall cell lung cancer), MES-SA (uterine sarcoma), LoVo (colon cancer), drug-resistant human cancer cells (MES-SA/DX5, LoVo/DX) and also towards non-cancer cell line MCF-10A (normal breast epithelial cells). The flavones modified with acyl group showed higher antiproliferative activity than free hydroxyflavones. The highest activity was noted for 3-acetoxyflavone ( 2 ), which proved active against LoVo, LoVo/DX, and MES-SA cell lines (IC 50 from 4.7 μM to 7.8 μM, respectively). The highest ability to overcome the barrier of resistance (resistance index=0.82) against the drug-resistant MES-SA/DX5 cells compared to the parental drug-sensitive MES-SA cell line was found for 7-acetoxyflavone ( 6 ).