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Journal of Natural Products

Adson S Soares, Felipe L Barbosa, André L Rüdiger, David L Hughes, Marcos J Salvador, Aleksander R Zampronio, Maria Élida A Stefanello
No abstract text is available yet for this article.
October 13, 2017: Journal of Natural Products
Jessica J Field, Benet Pera, Juan Estévez Gallego, Enrique Calvo, Javier Rodríguez-Salarichs, Gonzalo Sáez-Calvo, Didier Zuwerra, Michel Jordi, José M Andreu, Andrea E Prota, Grégory Ménchon, John H Miller, Karl-Heinz Altmann, J Fernando Díaz
The marine natural product zampanolide and analogues thereof constitute a new chemotype of taxoid site microtubule-stabilizing agents with a covalent mechanism of action. Zampanolide-ligated tubulin has the switch-activation loop (M-loop) in the assembly prone form and, thus, represents an assembly activated state of the protein. In this study, we have characterized the biochemical properties of the covalently modified, activated tubulin dimer, and we have determined the effect of zampanolide on tubulin association and the binding of tubulin ligands at other binding sites...
October 12, 2017: Journal of Natural Products
Yujie Yan, Yu An, Xiaozhong Wang, Yingqi Chen, Melissa R Jacob, Babu L Tekwani, Liyan Dai, Xing-Cong Li
The first synthesis of 2-methyl-6-pentadecyl-Δ(1,6)-piperideine (1), a major alkaloid of the piperideine chemotype in fire ant venoms, and its analogues, 2-methyl-6-tetradecyl-Δ(1,6)-piperideine (2) and 2-methyl-6-hexadecyl-Δ(1,6)-piperideine (3), was achieved by a facile synthetic method starting with glutaric acid (4) and urea (5). Compound 1 showed in vitro antifungal activity against Cryptococcus neoformans and Candida albicans with IC50 values of 6.6 and 12.4 μg/mL, respectively, and antibacterial activity against vancomycin-resistant Enterococcus faecium with an IC50 value of 19...
October 12, 2017: Journal of Natural Products
Yuuki Shimozu, Teruo Kuroda, Tomofusa Tsuchiya, Tsutomu Hatano
Three new ellagitannin oligomers, isorugosins H (1), I (2), and J (3), together with 11 known hydrolyzable tannins were isolated from an aqueous acetone extract of the fresh leaves of Liquidambar formosana. Their chemical structures were elucidated based on spectroscopic data and chemical conversion into known hydrolyzable tannins. The bridging mode of the valoneoyl groups between their sugar moieties has been identified only in this plant species. Additionally, the effects of the isorugosins isolated from this species on drug-resistant bacteria were evaluated and showed that isorugosin A (4) exhibited the most potent antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA)...
October 11, 2017: Journal of Natural Products
Julie G Petitbois, Loida O Casalme, Julius Adam V Lopez, Walied M Alarif, Ahmed Abdel-Lateff, Sultan S Al-Lihaibi, Erina Yoshimura, Yasuyuki Nogata, Taiki Umezawa, Fuyuhiko Matsuda, Tatsufumi Okino
NMR- and MS-guided fractionation of an extract of an Okeania sp. marine cyanobacterium, collected from the Red Sea, led to the isolation of four new metabolites, including serinolamides C (1) and D (2) and lyngbyabellins O (3) and P (4), together with the three known substances lyngbyabellins F (5) and G (6) and dolastatin 16 (7). The planar structures of the new compounds were determined using NMR and MS analyses. The absolute configurations of 1 and 2 were determined by Marfey's analysis of their hydrolysates...
October 11, 2017: Journal of Natural Products
John G Starkus, Peter Poerzgen, Kristine Layugan, Kelly Galbraith Kawabata, Jun-Ichi Goto, Sayuri Suzuki, George Myers, Michelle Kelly, Reinhold Penner, Andrea Fleig, F David Horgen
TRPM2 is a Ca(2+)-permeable, nonselective cation channel that plays a role in oxidant-induced cell death, insulin secretion, and cytokine release. Few TRPM2 inhibitors have been reported, which hampers the validation of TRPM2 as a drug target. While screening our in-house marine-derived chemical library, we identified scalaradial and 12-deacetylscalaradial as the active components within an extract of an undescribed species of Cacospongia (class Demospongiae, family Thorectidae) that strongly inhibited TRPM2-mediated Ca(2+) influx in TRPM2-overexpressing HEK293 cells...
October 11, 2017: Journal of Natural Products
Yoshinori Asakawa, Agnieszka Ludwiczuk
Comparatively little attention has been paid to the bryophytes for use in the human diet or medicine in spite of the presence of 23 000 species globally. Several hundred new compounds have been isolated from the liverworts (Marchantiophyta), and more than 40 new carbon skeletons of terpenoids and aromatic compounds were found. Most of the liverworts studied elaborate characteristic odiferous, pungent, and bitter-tasting compounds, of which many show antimicrobial, antifungal, antiviral, allergic contact dermatitis, cytotoxic, insecticidal, anti-HIV, plant growth regulatory, neurotrophic, NO production and superoxide anion radical release inhibitory, muscle relaxing, antiobesity, piscicidal, and nematocidal activities...
October 11, 2017: Journal of Natural Products
Xu Pang, Jian-Yuan Zhao, Xiao-Mei Fang, Tao Zhang, De-Wu Zhang, Hong-Yu Liu, Jing Su, Shan Cen, Li-Yan Yu
Thirty-three metabolites including five phenalenone derivatives (1-5), seven cytochalasins (6-12), thirteen butenolides (13-25), and eight phenyl derivatives (26-33) were isolated from Aspergillus sp. CPCC 400735 cultured on rice. The structures of all compounds were elucidated by NMR, MS, and CD experiments, of which 1-5 (asperphenalenones A-E), 6 (aspochalasin R), and 13 (aspulvinone R) were identified as new compounds. Specifically, asperphenalenones A-E (1-5) represent an unusual structure composed of a linear diterpene derivative linked to a phenalenone derivative via a C-C bond...
October 10, 2017: Journal of Natural Products
Kentaro Takada, Raku Irie, Rei Suo, Shigeki Matsunaga
Direct comparison of authentic ciliatamide A with four synthetic isomers (1-4) by means of NMR and chiral-phase HPLC revealed that ciliatamide A possesses the 12R (d-N-MePhe residue) and 22S (l-Lys residue) configurations, which were not identical with either our previous assignment or those proposed by others through total synthesis. The absolute configuration of the methionine sulfoxide residue in ciliatamide D was also revised to be d.
October 10, 2017: Journal of Natural Products
Ruimin Yang, Jing Yang, Li Wang, Jian-Ping Huang, Zijun Xiong, Jianying Luo, Mingming Yu, Yijun Yan, Sheng-Xiong Huang
Our natural products discovery program utilizes endophytic actinomycetes associated with plants and employs biological assays and HPLC-based metabolite profiles as the preliminary screen to identify strains of interest, followed by large-scale fermentation and isolation, leading to new and/or bioactive natural products. Six new trialkyl-substituted aromatic acids, namely, lorneic acids E-J (1-6), together with two known analogues (7 and 8), were isolated and identified from the culture extract of Streptomyces sp...
October 9, 2017: Journal of Natural Products
Jungmoo Huh, Thi Kim Quy Ha, Kyo Bin Kang, Ki Hyun Kim, Won Keun Oh, Jinwoong Kim, Sang Hyun Sung
Thirteen C-methylated flavonoid glycosides (1-13), along with 15 previously known flavonoids (14-28), were isolated from rhizomes of Pentarhizidium orientale. Among these compounds, matteuorienates D-K (1-8) were obtained as analogues of matteuorienates A-C (14-16), which contain a characteristic 3-hydroxy-3-methylglutaryl (HMG) moiety. The structures of 1-13 were characterized by spectroscopic analysis and chemical derivatization. The isolates were evaluated for their antiviral activities against influenza virus (H1N1), with compounds 21, 22, 23, 25, and 26 showing inhibitory effects (IC50 of 23...
October 6, 2017: Journal of Natural Products
Alla A Kicha, Anatoly I Kalinovsky, Natalia V Ivanchina, Timofey V Malyarenko, Pavel S Dmitrenok, Alexandra S Kuzmich, Ekaterina V Sokolova, Valentin A Stonik
Seven new asterosaponins, pentaregulosides A-G (1-7), including two furostane-type steroid oligoglycosides (2, 3), along with four previously known compounds (8-11) were isolated from the ethanolic extract of the starfish Pentaceraster regulus, collected off the coast of Vietnam. The structures of 1-7 were elucidated by extensive NMR and ESIMS techniques as well as chemical transformations. The aglycons of compounds 1 and 3 have not previously been observed in starfish steroid oligoglycosides, while the aglycons of compounds 2 and 4-6 are very rare for this structural group...
October 5, 2017: Journal of Natural Products
Diana Jæger, Chi P Ndi, Christoph Crocoll, Bradley S Simpson, Bekzod Khakimov, Ruth Marian Guzman-Genuino, John D Hayball, Xiaohui Xing, Vincent Bulone, Philip Weinstein, Birger L Møller, Susan J Semple
The Australian plant Acacia ligulata has a number of traditional food and medicinal uses by Australian Aboriginal people, although no bioactive compounds have previously been isolated from this species. Bioassay-guided fractionation of an ethanolic extract of the mature pods of A. ligulata led to the isolation of the two new echinocystic acid triterpenoid saponins, ligulatasides A (1) and B (2), which differ in the fine structure of their glycan substituents. Their structures were elucidated on the basis of 1D and 2D NMR, GC-MS, LC-MS/MS, and saccharide linkage analysis...
October 4, 2017: Journal of Natural Products
Carmina Sirignano, Alì Snene, Daniela Rigano, Sofia Tapanelli, Carmen Formisano, Paolo Luciano, Ridha El Mokni, Saoussen Hammami, Alain Rodrigue Tenoh, Annette Habluetzel, Orazio Taglialatela-Scafati
Phytochemical investigation of the aerial parts of the Tunisian plant Daucus virgatus led to the isolation of eight new germacranolides named daucovirgolides A-H (1-8). The stereostructures of these sesquiterpene lactones, decorated by either one or two angeloyl groups, have been determined by a combination of MS, NMR spectroscopy, chemical derivatization, and comparison of experimental electronic circular dichroism curves with TDDFT-predicted data. Daucovirgolide G (7) proved to be the single member of this family to possess a marked inhibitory activity (92% at 50 μg/mL) on the development of Plasmodium early sporogonic stages, the nonpathogenic transmissible stages of malaria parasites, devoid of general cytotoxicity...
October 4, 2017: Journal of Natural Products
Kyo Bin Kang, Eun Jin Park, Jinwoong Kim, Sang Hyun Sung
Three compounds in a new class of 2-acetoxy-ω-phenylpentaene fatty acid triglycosides, berchemiosides A-C (1-3), and a biosynthetically related phenolic glycoside (4) were isolated from the unripe fruits of Berchemia berchemiifolia, along with three flavonoid 5-O-diglycosides (5-7) and three known flavonoids (8-10). Their chemical structures including absolute configurations were determined by spectroscopic analysis in combination with chemical derivatization. The pentaene group of 1 was found to have (6E,8E,10Z,12Z,14E)-geometry, whereas those of 2 and 3 exhibited all-E geometries...
October 3, 2017: Journal of Natural Products
Tiphaine Péresse, Gwenaëlle Jézéquel, Pierre-Marie Allard, Van-Cuong Pham, Doan T M Huong, Florent Blanchard, Jérôme Bignon, Hélène Lévaique, Jean-Luc Wolfender, Marc Litaudon, Fanny Roussi
With the aim of discovering new cytotoxic prenylated stilbenes of the schweinfurthin series, Macaranga tanarius was selected for detailed phytochemical investigation among 21 Macaranga species examined by using a molecular networking approach. From an ethanol extract of the fruits, seven new prenylated stilbenes, schweinfurthins K-Q (7-13), were isolated, along with vedelianin (1), schwenfurthins E-G (2-4), mappain (5), and methyl-mappain (6). The structures of the new compounds were established by spectroscopic data analysis...
October 3, 2017: Journal of Natural Products
Hyung Won Ryu, Yhun Jung Park, Su Ui Lee, Seoghyun Lee, Heung Joo Yuk, Kyeong-Hwa Seo, Yeah-Un Kim, Bang Yeon Hwang, Sei-Ryang Oh
As part of an ongoing search for new natural products from medicinal plants to treat respiratory disease, six new compounds, a dihydroflavonol (1) and five C-geranylated flavanones (3, 6, 8, 13, and 14), and 13 known compounds were isolated from mature fruits of Paulownia tomentosa. The structures of the new compounds were determined via interpretation of their spectroscopic data (1D and 2D NMR, UV, IR, ECD, and MS). In biological activity assays with human alveolar basal epithelial cells, the expression of TNF-α-induced proinflammatory cytokines (IL-8 and IL-6) was reduced significantly by the EtOAc fraction of a P...
October 2, 2017: Journal of Natural Products
Hyun-Jae Jang, Soyoung Lee, Seung-Jae Lee, Hyung-Jin Lim, Kyungsook Jung, Young Ho Kim, Seung Woong Lee, Mun-Chual Rho
Nine new sesquiterpenoid lactones and 11 known analogues were isolated from the aerial parts of Salvia plebeia R.Br. Their structures were elucidated via HRESIMS and NMR data, and their absolute configurations were defined via electronic circular dichroism data, X-ray crystallographic analysis, and the modified Mosher's ester method. Compounds 1-20 were investigated for their ability to inhibit LPS-stimulated nitric oxide production in murine macrophage cells. Of the isolates, epi-eudebeiolide C (20) showed the highest inhibitory effect (IC50 of 17...
September 29, 2017: Journal of Natural Products
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