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Journal of Natural Products

Chang-An Geng, Xiao-Yan Huang, Yun-Bao Ma, Bo Hou, Tian-Ze Li, Xue-Mei Zhang, Ji-Jun Chen
(±)-Uncarilins A and B (1a/1b and 2a/2b), two pairs of unusual dimeric isoechinulin-type enantiomers with a symmetric four-membered core, were isolated from Uncaria rhynchophylla driven by LCMS-IT-TOF analyses. Their structures were elucidated by extensive 1D and 2D NMR spectra, X-ray diffraction, and ECD spectroscopic data. (-)-Uncarilin B (2a) showed activities on MT1 and MT2 receptors with agonistic rates of 11.26% and 52.44% at a concentration of 0.25 mM.
February 22, 2017: Journal of Natural Products
Peng Fu, Scott La, John B MacMillan
Three new cyclohexene amine derivatives, daryamides D-F (1-3), a new arylamine derivative, carpatamide D (4), and a new ornithine lactamization derivative, ornilactam A (5), were isolated from the marine-derived Streptomyces strain SNE-011. Their structures, including absolute configurations, were elucidated on the basis of spectroscopic analysis and chemical methods. The carpatamide skeleton could be considered as the biosynthetic precursor of the daryamides.
February 22, 2017: Journal of Natural Products
Marianna Iorio, João Cruz, Matteo Simone, Alice Bernasconi, Cristina Brunati, Margherita Sosio, Stefano Donadio, Sonia I Maffioli
Four metabolites, designated paramagnetoquinone A, B, C, and D (1-4), were isolated from three strains belonging to the actinomycete genus Actinoallomurus. Compounds 1 and 2 showed potent antibacterial activity with MIC values lower than 0.015 μg/mL against Gram-positive pathogens, including antibiotic-resistant strains. Since compounds 1 and 2 were NMR-silent due to the presence of an oxygen radical, structure elucidation was achieved through a combination of derivatizations, oxidations, and analysis of (13)C-labeled compounds...
February 20, 2017: Journal of Natural Products
Ting Zeng, Xiu-Yin Wu, Shu-Xia Yang, Wei-Chun Lai, Shun-Dong Shi, Qiang Zou, Yang Liu, Li-Mei Li
Six new monoterpenoid indole alkaloids, kopsinidines C-E (1-3), 11,12-methylenedioxychanofruticosinic acid (4), 12-methoxychanofruticosinic acid (5), and N(4)-methylkopsininate (7), as well as chanofruticosinic acid (6, as a natural product) and 23 known alkaloids, were obtained from the twigs and leaves of Kopsia officinalis. Their structures were characterized by physical data analysis. All isolated compounds were evaluated for their immunosuppressive activity on human T cell proliferation. Rhazinilam (29) significantly inhibited human T cell proliferation activated by anti-CD3/anti-CD28 antibodies (IC50 = 1...
February 20, 2017: Journal of Natural Products
Ping-Chung Kuo, Hsin-Yi Hung, Chi-Wei Nian, Tsong-Long Hwang, Ju-Chien Cheng, Daih-Huang Kuo, E-Jian Lee, Shih-Huang Tai, Tian-Shung Wu
Fifty compounds were isolated from the fruits of Forsythia suspensa, including 13 new compounds characterized as eight new diterpenoids (1-8), three new lignans (9-11), a new iridoid (12), and a new triterpenoid (13). Their structures were established on the basis of spectroscopic and spectrometric analysis. Most of the isolated compounds were examined for their anti-inflammatory activity in vitro. The results showed that several compounds displayed significant inhibition of fMLP/CB-induced superoxide anion generation and elastase release, with IC50 values ranging from 0...
February 20, 2017: Journal of Natural Products
Fan-Dong Kong, Qing-Yun Ma, Sheng-Zhuo Huang, Pei Wang, Jun-Feng Wang, Li-Man Zhou, Jing-Zhe Yuan, Hao-Fu Dai, You-Xing Zhao
Six new meroterpenoids, chrodrimanins K-N (1-4), including two uncommon chlorinated ones (1 and 2), and verruculides B2 (5) and B3 (6), as well as seven known ones (7-13), were isolated from the fermentation broth of Penicillium sp. SCS-KFD09 isolated from a marine worm, Sipunculus nudus, from Haikou Bay, China. The structures including the absolute configurations of the new compounds were unambiguously elucidated by spectroscopic data, X-ray diffraction analysis, and ECD spectra analysis along with quantum ECD calculations...
February 17, 2017: Journal of Natural Products
Yancho Zarev, Kenn Foubert, Iliana Ionkova, Sandra Apers, Luc Pieters
Four new colchicinoids were isolated from the seeds of Gloriosa superba together with the known compounds colchicoside (4) and 3-de-O-methylcolchicine-3-O-β-d-glucopyranosyl-(1→4)-3-O-β-d-glucopyranoside (6), by means of conventional column chromatography and LC-DAD-SPE-NMR. The new compounds were identified as N-deacetyl-N-formyl-3-de-O-methylcolchicine-3-O-β-d-glucopyranoside (1), 3-de-O-methylcolchicine-3-O-β-d-glucopyranosyl-(1→6)-3-O-β-d-glucopyranoside (2), N-deacetyl-N-formyl-3-de-O-methylcolchicine-3-O-β-d-glucopyranosyl-(1→6)-3-O-β-d-glucopyranoside (3), and 3-de-O-methylcolchicine-3-O-β-d-glucopyranosyl-(1→3)-3-O-β-d-glucopyranoside (5)...
February 17, 2017: Journal of Natural Products
George R Pettit, Noeleen Melody, Jean-Charles Chapuis
Discovery of the exceptionally powerful anticancer drug dolastatin 10 (1), contained in the sea hare Dolabella auricularia, opened a new frontier needed for improving human cancer treatment. Subsequently, major advances have been achieved based on results of structurally modifying this unusual natural peptide while maintaining the remarkable anticancer activity necessary for preparation of successful monoclonal antibody drug conjugates (ADC). Among the first several hundred SAR products based on dolastatin 10 our group synthesized and termed auristatins was auristatin E (2a)...
February 17, 2017: Journal of Natural Products
Michal Issac, Maurice Aknin, Anne Gauvin-Bialecki, Nicole De Voogd, Alisson Ledoux, Michel Frederich, Yoel Kashman, Shmuel Carmeli
The extract of a sample of the sponge Theonella aff. swinhoei collected in Madagascar exhibited promising in vitro antiplasmodial activity. The antiplasmodial activity was ascribed in part to the known metabolite swinholide A. Further investigation of the extract afforded three unusual cyclic peptides, cyclotheonellazoles A-C (1-3), which contain six nonproteinogenic amino acids out of the eight acid units that compose these natural products. Among these acids the most novel were 4-propenoyl-2-tyrosylthiazole and 3-amino-4-methyl-2-oxohexanoic acid...
February 16, 2017: Journal of Natural Products
Takaaki Kubota, Kenta Nakamura, Shin-Ichiro Kurimoto, Kanae Sakai, Jane Fromont, Tohru Gonoi, Jun'ichi Kobayashi
A new manzamine alkaloid, zamamidine D (1), was isolated from an Okinawan Amphimedon sp. marine sponge. The structure of zamamidine D (1) including the relative configuration was elucidated on the basis of spectroscopic data. Zamamidine D (1) is the first manzamine alkaloid possessing a 2,2'-methylenebistryptamine unit as the aromatic moiety instead of a β-carboline unit. Zamamidine D (1) showed antimicrobial activity against several bacteria and fungi.
February 16, 2017: Journal of Natural Products
Dan Zheng, Li Han, Xiaodan Qu, Xiu Chen, Jialiang Zhong, Xiaoxu Bi, Jiang Liu, Yi Jiang, Chenglin Jiang, Xueshi Huang
Six new fusicoccane-type diterpenoids (2-7) were isolated from the fermentation broth of Streptomyces violascens, which was isolated from Ailuropoda melanoleuca (giant panda) feces. The structures of these new compounds were elucidated by a detailed spectroscopic data and X-ray crystallographic analysis. Compounds 5-7 demonstrated cytotoxicity against five human cancer cell lines, with IC50 values ranging from 3.5 ± 0.7 to 14.1 ± 0.8 μM. Cell adhesion, migration, and invasion assays showed that 6 inhibited the migration and invasion of human hepatocellular carcinoma SMMC7721 cells in a dose-dependent manner...
February 16, 2017: Journal of Natural Products
Huzefa A Raja, Andrew N Miller, Cedric J Pearce, Nicholas H Oberlies
Fungi are morphologically, ecologically, metabolically, and phylogenetically diverse. They are known to produce numerous bioactive molecules, which makes them very useful for natural products researchers in their pursuit of discovering new chemical diversity with agricultural, industrial, and pharmaceutical applications. Despite their importance in natural products chemistry, identification of fungi remains a daunting task for chemists, especially those who do not work with a trained mycologist. The purpose of this review is to update natural products researchers about the tools available for molecular identification of fungi...
February 15, 2017: Journal of Natural Products
Loïc Tissandié, Marc Gaysinski, Hugues Brévard, Uwe J Meierhenrich, Jean-Jacques Filippi
Guaiacwood oil from Bulnesia sarmientoi Lorentz ex. Griseb is a common natural ingredient of the perfume industry used in both domestic and luxury fragrances for its highly appreciated woody-rosy odor, as well as its excellent fixative properties. Despite its long and traditional use as a perfume ingredient, guaiacwood oil has not been extensively studied. Thus, the chemical characterization of its constituents by using a full array of GC-hyphenated techniques (GC-MS, GC × GC-MS, and pc-GC) combined with conventional chemical fractionation was undertaken...
February 14, 2017: Journal of Natural Products
Muhammad Abdul Mojid Mondol, Jannatul Farthouse, Mohammad Tofazzal Islam, Anja Schüffler, Hartmut Laatsch
The endophytic fungus Curvularia sp., strain M12, was isolated from a leaf of the medicinal plant Murraya koenigii and cultured on rice medium followed by chemical screening of the culture extract. Chromatographic analysis led to the isolation of four new compounds, murranofuran A (1), murranolide A (2), murranopyrone (3a), and murranoic acid A (4a), along with six known metabolites, N-(2-hydroxy-6-methoxyphenyl)acetamide (5), curvularin (6), (S)-dehydrocurvularin (7), pyrenolide A (8), modiolide A (9), and 8-hydroxy-6-methoxy-3-methylisocoumarin (10)...
February 14, 2017: Journal of Natural Products
Yu-Shiuan Cheng, Wenyuan Yu, Yunfeng Xu, Robert G Salomon
Levuglandins (LG)D2 and LGE2 are γ-ketoaldehyde levulinaldehyde derivatives with prostanoid side chains produced by spontaneous rearrangement of the endoperoxide intermediate PGH2 in the biosynthesis of prostaglandins. Covalent adduction of LGs with the amyloid peptide Aβ1-42 promotes formation of the type of oligomers that have been associated with neurotoxicity and are a pathologic hallmark of Alzheimer's disease. Within 1 min of their generation during the production of PGH2 by cyclooxygenation of arachidonic acid, LGs are sequestered by covalent adduction to proteins...
February 14, 2017: Journal of Natural Products
Midori A Arai, Mitsuha Tanaka, Kana Tanouchi, Naoki Ishikawa, Firoj Ahmed, Samir K Sadhu, Masami Ishibashi
Hairy and enhancer of split 1 (Hes1) is a transcription factor that acts in neural stem cells to inhibit differentiation. We recently developed target protein oriented natural products isolation (TPO-NAPI) using Hes1-immobilized beads to identify activators of neural stem cells. Isomicromonolactam (1), staurosporin (2), and linarin (3) were isolated as Hes1-binding compounds using the TPO-NAPI method. Of these, compound 1 enhanced neural stem cell differentiation. Using truncated Hes1 proteins, the binding region of Hes1 for 1 was estimated to be in the C-terminal half that includes a TLE/Grg binding site...
February 13, 2017: Journal of Natural Products
Karen J Nicacio, Laura P Ióca, Adriana M Fróes, Luciana Leomil, Luciana R Appolinario, Christiane C Thompson, Fabiano L Thompson, Antonio G Ferreira, David E Williams, Raymond J Andersen, Alessandra S Eustaquio, Roberto G S Berlinck
Herein we report the isolation and spectroscopic identification of fistularin-3 (1), 11-hydroxyaerothionin (2), and verongidoic acid (3), as well as the UPLC-HRMS detection of aerothionin (4), homopurpuroceratic acid B (5), purealidin L (6), and aplysinamisine II (7), from cultures of the marine bacterium Pseudovibrio denitrificans Ab134, isolated from tissues of the marine sponge Arenosclera brasiliensis. These results unambiguously demonstrate for the first time that bromotyrosine-derived alkaloids that were previously isolated only from Verongida sponges can be biosynthesized by a marine bacterium...
February 13, 2017: Journal of Natural Products
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