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Natural Product Communications

Alfonso Alejo-Armijo, Joaquín Altarejos, Sofía Salido
This review summarizes the chemical composition reported up to date on Laurus nobilis L. (Lauraceae), an evergreen shrub or tree cultivated for its aromatic leaves and ornamental interest. It has been focused on non-volatile phytochemicals such as sesquiterpene lactones, flavonoids and proanthocyanidins, among others. Moreover, biological activities of laurel extracts and pure compounds have also been reviewed.
May 2017: Natural Product Communications
Alejandro F Barrero, M Mar Herrador Del Pino, Jesús F Arteaga, José A González-Delgado
Apocarotenoids are metabolites originated by degradation of carotenes through the loss of carbon atoms placed at the side chain of their structure as consequence of oxydative reactions. We present here the first review of apocarotenoids in the fungi mucorales Phycomyces blakesleeanus, Blakeslea trispora and Mucor mucedo. This review is divided into two parts: the first one presents their structures and sources, whereas the second part is dedicated to their chemical synthesis.
May 2017: Natural Product Communications
Silvia Roscales, Joaquín Plumet
Metathesis reactions is firmly established as a valuable synthetic tool in organic chemistry, clearly comparable with the venerable Diels-Alder and Wittig reactions and, more recently, with the metal-catalyzed cross-coupling reactions. Metathesis reactions can be considered as a fascinating synthetic methodology, allowing different variants regarding substrate (alkene and alkyne metathesis) and type of metathetical reactions. On the other hand, tandem metathesis reactions such.Ring Rearrangement Metathesis (RRM) and the coupling of metathesis reaction with other reactions of alkenes such as Diels-Alder or Heck reactions,...
May 2017: Natural Product Communications
Nuria I Guardo, Paula Sainz, Azucena González-Coloma, Jesús Burillo, Rafael A Martinez-Díaz
Fourteen essential oils (EOs) from selected live germplasm of medicinal plants have been tested for their antitrypanosomal and cytotoxic activity. These plants have been domesticated and maintained under experimental cultivation. Their EOs were tested on epimastigote forms of Trypanosoma cruzi strain Y and human lung fibroblasts LC5 cell line, along with the major components of the active oils, both separately and in binary combinations. Mentha rotundifolia, Thymus zygis, T. vulgaris and Hyssopus officinalis were the most active EOs against T...
May 2017: Natural Product Communications
Yamile Massuh, Angel Cruz-Estrada, Azucena González-Coloma, Marta S Ojeda, Julio A Zygadlo, Maria Fe Andrés
Essential oils composition of three Tagetes minuta varieties and a wild population (WP) from Argentina and their in vitro and in vivo nematicidal activity against root-knot nematode, Meloidogynejavanica, are described. All T. minuta EOs tested were very active against nematode juveniles (J2), but the strongest nematicidal effects were exhibited by the TmV3 variety oil, characterized by a high content of (E)-ocimenone. High nematode egg hatching suppression (> 90%) was induced by TmV3 EO after five days of incubation...
May 2017: Natural Product Communications
Rosa Martí-Centelles, Juan Murga, Eva Falomira, Miguel Carda, J Alberto Marco
A group of 28 N-benzylidene aniline derivatives structurally related to the natural stilbene resveratrol has been prepared through condensation of anilines with the corresponding aldehydes. The ability of these imines to inhibit proliferation of two tumor cell lines (HT-29 and MCF-7) and one non-tumor cell line (HEK- 293) was first determined. Subsequently, we determined the ability of some of the most cytotoxic compounds to inhibit the secretion of the VEGF-A factor in HT-29 cells and to downregulate the expression of the VEGF and hTERT genes, the latter one being involved in the activation of telomerase...
May 2017: Natural Product Communications
Maitane Maisterra, Ma Ángeles Castro, Luz Ma Muñoz-Centeno, Ricardo C Calhelha, Isabel C Ferreira, Pablo A García
The cobalt crust fungus Terana coerulea (Phanerochaetaceae family) was selected for a bio-guided study after an ethnobotanical survey at the Irati's Forest (Navarra, Spain) for its local use as antibiotic. Six extracts of increasing polarity, from hexane to hot water, were obtained from powdered dry fungi and tested for cytotoxicity against four human tumour cell lines and one non-tumour primary cell culture. From the most cytotoxic, EtOAc extract, we isolated and identified three terphenyl neolignans: two of them new natural products, named corticins D and E, and one previously described as corticin A, whose earlier structure has been revised...
May 2017: Natural Product Communications
Braulio M Fraga, Inmaculada Cabrera
In an earlier work we reported that treatment of precocene I with Brönsted and Lewis acids produces its oligomerization, giving dimers, trimers, tetramers, etc. Now, in this article we show that bromination of precocene I with phenyltrimethylammonium tribromide (PTT) blocks its oligomerization giving a dibromo- dimer, which was reduced with tri-n-butyl tin hydride affording the same dimer obtained in the reactions with acid, thus avoiding the oligomerization. Additionally, the oxidations of precocene I with Jones reagent afforded the corresponding 3-hydroxy-4-chromanone, 3,4-chromandione, 3,4-diacid, and two dimers...
May 2017: Natural Product Communications
Lauren Manck, Ester Quintana, Rocio Suárez, Fernando G Brunb, Ignacio Hernández, Maria J Ortega, Eva Zubia
Seagrasses are marine plants that play important ecological functions in coastal ecosystems. The species Zostera noltei is widely distributed along the European coasts thriving in a variety of environmental conditions. In this study, the phenolic natural products of Z. noltei have been analyzed quantitatively by using UPLC-MS. Plants from the Natural Park of the Bay of Cadiz (Spain) were shown to contain rosmarinic acid (1) and the flavonoids apigenin-7-0- glucoside (2), luteolin-7-sulfate (7), apigenin-7-sulfate (8), diosmetin-7-sulfate (9), and acacetin-7-sulfate (10)...
May 2017: Natural Product Communications
Eleuterio Burgueño-Tapia, Mariano Sánchez-Castellanos, Pedro Joseph-Nathan
Epimeric catechin and epicatechin peracetates offer the possibility to explore the number of conformers needed for the absolute configuration determination without affecting the reliability of the assignment. Comparisons between experimental and DFT B3PW91/DGDZVP calculated curves showed that, in molecules.where the conformational flexibility generates a large number of conformers, it is possible to significantly reduce the number of conformers needed to generate VCD results that provide secure absolute configuration assignment...
May 2017: Natural Product Communications
Margarida Costa, Paz Zúñiga, Ana Ma Peñalver, Margrét Thorsteinsdottir, Marta Pérez, Librada M Cañedo, Carmen Cuevas
Two new fluvirucin aglycones, named fluvirucinins C, and C2 (1-2), have been isolated from the ethyl acetate mycelial cake extract of the fermentation broth of.a marine sponge-associated actinomycete. Fluvirucinins C, (1) and C2 (2) represent a new type of 14-membered macrolactam aglycon, structurally related with the common aglycon of the known fluvirucins. Their structures were elucidated on the basis of ID and 2D NMR analyses, as well as HRESIMS experiments. The antimicrobial and cytotoxic activities of compounds 1 and 2 have been evaluated, but no significant activities found for fluvirucinins C, and C2...
May 2017: Natural Product Communications
Carolina P Reyes, Ignacio A Jiménez, Isabel L Bazzocchi
Phytochemical analysis of the root bark extract of Maytenus cuzcoina (Celastraceae) led to the isolation and characterization of sixteen triterpenoids with a 6/6/6/6/6 pentacyclic system, including the new 22α-hydroxy-29-methoxy-3β-tetradecanoate-olean-12-ene, and 3β,24β-epoxy-29-methoxy-2α,3α,6α- -trihydroxy-D:A-friedelane that is reported for the first time as a natural product. This is the first instance of the isolation of a tetradecanoate triterpene ester from a Celastraceae species. The structures were elucidated on the basis of spectrometric and spectroscopic methods, including ID and 2D NMR techniques...
May 2017: Natural Product Communications
María Jesús Durán-Peña, María Eugenia Flores-Giubi, José Manuel Botubol-Ares, Felipe Escobar-Montaño, Antonio J Macías-Sánchez, Luis F Echeverri, Isidro G Collado, Rosario Hernández-Galán
Two new macrocyclic diterpenes, 2-epi-latazienone (4) and 15β-acetoxy-7β-nicotinoyloxy-3β,8α-di-(2-methylpropanoyloxy)-4αH,9αH,l1αH-lathyra- 5E,12E-dien-14-one (5), and three known lathyrane-type diterpenes (1-3) were isolated from Euphorbia laurifolia latex. Their structures were determined on the basis of a detailed analysis of their 1D and 2D NMR spectroscopic and mass spectral data.
May 2017: Natural Product Communications
Ignacio E Tobal, Lourdes Castañeda, Alejandro M Roncero, Rosalina F Moro, David Diez, Isidro S Marcos
Sclareol has been employed as starting material for the synthesis of several advanced intermediates towards the synthesis of highly ring B oxygenated labdanes. Dinorlabdanes 6,7,8,9-tetraoxygenated with 6,7-dioxygenated functionalities with a-cis or O-cis dispositions, have been prepared and can be used for forskolin or analogues synthesis.
May 2017: Natural Product Communications
M Teresa Agulló-Ortuño, Carmen E Diaz, Azucena González-Coloma, Matías Reina
The aim of this research was to determine the cytotoxic action of sixteen structurally-related eremophilane-type sesquiterpenes, isolated from several species of Senecio, against a panel of cancer cell lines. The cytotoxic activities were evaluated by WST-I test and the ICso values calculated. The investigated compounds exerted dose-dependent cytotoxic actions against selected cancer cell lines and no-tumoral HS5 cell line. The comparative structure-activity relationships demonstrated the importance of C-1, C-6, and C-8 substituents in the molecule...
May 2017: Natural Product Communications
Alexis Castillo, José Fco Quilez Del Moral, Alejandro F Barrero
Two catalytic cascade cyclization methods (radical and 'cationic) to obtain aromatic polycyclic diterpenes hydroxylated at C3 starting from aromatic epoxypolyprenes were developed. The catalytic use of the Lewis superacid bismuth triflate produces a good yield of cyclized 2 from epoxypolyprene 3. This researchmay well direct future efforts to the synthesis of bioactive natural products.
May 2017: Natural Product Communications
Sofia Pombal, Yaiza Hernández, David Diez, Eily Mondolis, Aldahir Mero, Juan Morin-Pinzón, Estela I Guerrero, Jesús M Rodilla
Carvone has corroborated its versatility as starting material for building blocks synthesis in organic chemistry, being achieved a new chiral lactone. It has been done a study on the antioxidant activity against superoxide of carvone and a chloro derivative that show the potent activity of the natural product (R)-carvone, 1.
May 2017: Natural Product Communications
Sabrin R M Ibrahim, Gamal A Mohamed, Amgad I M Khedr
Recently, numerous metabolites possessing uncommon structures and potent bioactivity have been isolated from strains of fungi collected from diverse environments. The genus Aspergillus is known as a rich source of y-butyrolactones. These are a group of fungal secondary metabolites, consisting of a five- membered lactone bearing two aromatic rings, which shows a great variety of biological activities. This review summarizes the research on the biosynthesis, source, and biological activities of the naturally occurring y-butyrolactones that have been isolated from Aspergillus species published over the last decades...
May 2017: Natural Product Communications
Entela Hodaj-Çeliku, Olga Tsiftsoglou, Lulëzim Shuka, Sokol Abazi, Dimitra Hadjipavlou-Litina, Diamanto Lazari
The chemical compositions have been investigated of the volatile oils of nine populations of six species from Albania, namely Artemisia absinthium, Calamintha nepeta, Hypericum perforatum, Sideritis raeseri subsp. raeseri, Origanum vulgare subsp. hirtum from two wild .populations, and Salvia officinalis (sage) from two wild and one cultivated population,. The essential oils were obtained by hydrodistillation and their analyses were performed by GC-MS. The major constituents were: A. absinthium: neryl isovalerate (19...
May 2017: Natural Product Communications
Shan-Shan Wang, Ning-Ning Zhang, Ning He, Wen-Qiang Guo, Xuan Lei, Qiang Cai, Bin Hong, Yun-Ying Xie
Further exploration of substrate diversity of the sansaninycin biosynthetic pathway using available halogen- and methyl-phenylalanines led to the generation of diverse sansanmycin derivatives, either at the single C- or N-terminus alone or at both C- and N-termini. The structures of all of these derivatives were determined by MS/MS spectra, and amongst them, the structures of [2-Cl-Phe]-sansanmycin H (1) and [2-Cl-Phe]-sansanmycin A (2) were further identified by NMR. Both the C-terminal derivative I and the N-terminal derivative 2 were assayed for their antibacterial activitiesi and compound 1 exhibited moderate activity against P...
May 2017: Natural Product Communications
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