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Journal of Natural Products

Yan Zhang, Navid Adnani, Doug R Braun, Gregory A Ellis, Kenneth J Barns, Shirley Parker-Nance, Ilia A Guzei, Tim S Bugni
Despite the fact that actinomycetes harbor the genetic potential to produce terpenes, terpenoid natural products tend to be a rare occurrence in fermentation broths. Here we report two new halimane-type diterpenoids, micromonohalimanes A (1) and B (2), that were isolated from a Micromonospora sp. cultivated from the marine ascidian Symplegma brakenhielmi. This is the first report of the halimane-type diterpenoids from Micromonospora. The structures were determined using spectroscopic methods including X-ray crystallography to establish the absolute configuration...
November 4, 2016: Journal of Natural Products
Michelle F S Pinto, Osmar N Silva, Juliane C Viana, William F Porto, Ludovico Migliolo, Nicolau B da Cunha, Nelson Gomes, Isabel C M Fensterseifer, Michelle L Colgrave, David J Craik, Simoni C Dias, Octavio L Franco
The extraction and purification of parigidin-br3, a cyclotide analogue belonging to the "bracelet" subfamily, from Palicourea rigida leaves is discussed. Unlike conventional cyclotides, parigidin-br3 has free N- and C-termini, as identified by MALDI-TOF/TOF analysis and confirmed by gene structure elucidation, and is one of a small number of acyclotides discovered during recent years. Parigidin-br3 showed cytotoxic activity against MCF-7 (breast cancer) and CACO2 (colorectal adenocarcinoma) cells, with IC50 values of ∼2...
November 3, 2016: Journal of Natural Products
Kuei-Hung Lai, Mei-Chin Lu, Ying-Chi Du, Mohamed El-Shazly, Tung-Ying Wu, Yu-Ming Hsu, Astrid Henz, Juan-Cheng Yang, Anders Backlund, Fang-Rong Chang, Yang-Chang Wu
Six new and 16 known lanostanoids were isolated from the sclerotia of Poria cocos. The structures of the new isolates were elucidated to be 16α-hydroxy-3-oxo-24-methyllanosta-5,7,9(11),24(31)-tetraen-21-oic acid (1), 3β,16α,29-trihydroxy-24-methyllanosta-7,9(11),24(31)-trien-21-oic acid (2), 3β,16α,30-trihydroxy-24-methyllanosta-7,9(11),24(31)-trien-21-oic acid (3), 3β-acetoxy-16α,24β-dihydroxylanosta-7,9(11),25-trien-21-oic acid (4), 3β,16α-dihydroxy-7-oxo-24-methyllanosta-8,24(31)-dien-21-oic acid (5), and 3α,16α-dihydroxy-7-oxo-24-methyllanosta-8,24(31)-dien-21-oic acid (6), based on extensive spectroscopic analyses...
November 3, 2016: Journal of Natural Products
Barbara Tóth, Erika Liktor-Busa, Norbert Kúsz, Ádám Szappanos, Attila Mándi, Tibor Kurtán, Edit Urbán, Judit Hohmann, Fang-Rong Chang, Andrea Vasas
The present study has focused on an investigation of the antibacterial effects of Juncus inflexus and the isolation and identification of its active compounds. Eleven phenanthrenes were isolated from a methanolic extract of the roots. Four compounds (jinflexins A-D, 1-4) are new natural products, while seven phenanthrenes [juncuenins A (5), B (6), and D (8), juncusol (7), dehydrojuncuenins A (9) and B (11), and dehydrojuncusol (10)] were isolated for the first time from the plant. Jinflexin D (4) is a dimer with an unprecedented heptacyclic ring system...
November 3, 2016: Journal of Natural Products
Michael D Rush, Elisabeth M Walker, Tristesse Burton, Richard B van Breemen
To expedite the identification of active natural products in complex mixtures such as botanical extracts, a magnetic microbead affinity selection screening (MagMASS) procedure was developed. This technique utilizes target proteins immobilized on magnetic beads for rapid bioaffinity isolation of ligands from complex mixtures. A MagMASS method was developed and validated for 15-lipoxygenase. As a proof of concept, several North American prairie plants used medicinally by Native Americans were extracted with MeOH and screened...
November 1, 2016: Journal of Natural Products
Orkhon Banzragchgarav, Toshihiro Murata, Gendaram Odontuya, Buyanmandakh Buyankhishig, Keisuke Suganuma, Bekh-Ochir Davaapurev, Noboru Inoue, Javzan Batkhuu, Kenroh Sasaki
Eleven 2,5-diphenyloxazole derivatives (1-11), together with six known isoflavonoid derivatives, were isolated from the roots of Oxytropis lanata. The 2,5-diphenyloxazole (1) obtained proved to be identical to a standard sample used as a scintillator and liquid laser dye. The other oxazole derivatives isolated were found to have one to four hydroxy and/or O-methyl groups in their phenyl rings. Seven of the oxazole derivatives obtained are new (3-9). The inhibitory activity of the isolated compounds was evaluated against Trypanosoma congolense, the causative agent of African trypanosomosis in animals...
October 31, 2016: Journal of Natural Products
Juan M Calle, Andy J Pérez, Ana M Simonet, José O Guerra, Francisco A Macías
Four new steroidal saponins (1-4) along with 13 known saponins were isolated from the leaves of Furcraea hexapetala. The new compounds were identified as (20R,22R,25R)-3β-hydroxy-5α-spirostan-12-one 3-O-{α-l-rhamnopyranosyl-(1→4)-O-β-d-glucopyranosyl-(1→3)-O-[β-d-glucopyranosyl-(1→3)-O-β-d-glucopyranosyl-(1→2)]-O-β-d-glucopyranosyl-(1→4)-O-β-d-galactopyranoside} (1), (25R)-3β-hydroxy-5α-spirost-20(21)-en-12-one 3-O-{α-l-rhamnopyranosyl-(1→4)-O-β-d-glucopyranosyl-(1→3)-O-[β-d-glucopyranosyl-(1→3)-O-β-d-glucopyranosyl-(1→2)]-O-β-d-glucopyranosyl-(1→4)-O-β-d-galactopyranoside} (2), (25R)-5α-spirostan-3β-ol 3-O-{β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→4)-O-β-d-galactopyranoside} (3), and (25R)-5β-spirostan-3β-ol 3-O-{β-d-glucopyranosyl-(1→6)-O-β-d-galactopyranoside} (4) by spectroscopic analysis, including one- and two-dimensional NMR techniques, mass spectrometry, and chemical methods...
October 31, 2016: Journal of Natural Products
Chen Wang, Ping Wu, Shuai Tian, Jinghua Xue, Liangxiong Xu, Hanxiang Li, Xiaoyi Wei
Thirteen new pentacyclic triterpenoids, cleistocalyxic acids A-K (1, 2, 4, 5, and 7-13) and cleistocalyxolides A (3) and B (6), and 15 known analogues (14-28), based on taraxastane, oleanane, ursane, multiflorane, and lupane skeletons, were isolated from the leaves of Cleistocalyx operculatus. The structures of 1-13 were elucidated by analysis of their spectroscopic data and ECD/TDDFT computations. Cleistocalyxolide A (3), presumed to be derived from the known taraxastane-type compound 14, has a rare rearranged triterpenoid backbone...
October 31, 2016: Journal of Natural Products
Paul Coulerie, Yann Ratinaud, Sofia Moco, Loraine Merminod, Martine Naranjo Pinta, Julien Boccard, Laurent Bultot, Maria Deak, Kei Sakamoto, Emerson Ferreira Queiroz, Jean-Luc Wolfender, Denis Barron
To identify natural bioactive compounds from complex mixtures such as plant extracts, efficient fractionation for biological screening is mandatory. In this context, a fully automated workflow based on two-dimensional liquid chromatography (2D-LC × LC) was developed, allowing for the production of hundreds of semipure fractions per extract. Moreover, the ELSD response was used for online sample weight estimation and automated concentration normalization for subsequent bioassays. To evaluate the efficiency of this protocol, an enzymatic assay was developed using AMP-activated protein kinase (AMPK)...
October 28, 2016: Journal of Natural Products
Xiao-Jing Lv, Yong Li, Shuang-Gang Ma, Jing Qu, Yun-Bao Liu, Yu-Huan Li, Dan Zhang, Li Li, Shi-Shan Yu
Eleven new 9,10-seco-cycloartan triterpene glycosides (1-11), seven new lanostane triterpene glycosides (12-18), and two new ursane triterpenoids (19-20) were isolated from the twigs and leaves of Lyonia ovalifolia. The structures of these compounds were elucidated by extensive MS and NMR spectroscopic analysis. The absolute configuration of compound 1a (the aglycone of 1) was established by X-ray crystallography, and that of C-24 in compounds 2, 7, and 12 was established by Mo2(OAc)4-induced electronic circular dichroism experiments...
October 28, 2016: Journal of Natural Products
Jin-Long Li, Lei Wu, Jian Wu, Hong-Xuan Feng, Hong-Min Wang, Yan Fu, Ru-Jun Zhang, Hai-Yan Zhang, Wei-Min Zhao
Three new triterpenoids, celastrusins A-C (1-3), together with 3-O-caffeoyl-α-amyrin (4) were isolated from the root bark of Celastrus orbiculatus. Their structures were identified by spectroscopic analysis, X-ray crystallography using Cu Kα radiation, and the comparison of both observed and reported spectroscopic data. An in vitro bioassay revealed that the caffeoyl triterpenoid esters 1, 3, and 4 possess neuroprotective effects against oxygen-glucose deprivation (OGD) induced SH-SY5Y cell damage. Further animal studies indicated that compound 1 significantly reduced brain infarction after transient middle cerebral artery occlusion (MCAO) in rats using a 10 mg/kg (i...
October 28, 2016: Journal of Natural Products
Amira Arciniegas, Ana-L Pérez-Castorena, Antonio Nieto-Camacho, José L Villaseñor, Alfonso Romo de Vivar
The phytochemical study of the aerial parts of Melampodium perfoliatum afforded six melampolides (1, 3, 5-8), a eudesmanolide (9), two diterpene lactones (10, 11), and two ent-kaurane derivatives (12, 13), together with the known melampodin (2) and polymatin A (4). The structures of the compounds were elucidated by physical data analysis and chemical reactions. Compounds 2, 4, 5, and 10 exhibited dose-dependent anti-inflammatory activity on the 12-O-tetradecanoylphorbol-13-acetate-induced ear edema model, with ID50 values of 1...
October 27, 2016: Journal of Natural Products
Fayrouz El Maddah, Stefan Kehraus, Mamona Nazir, Celso Almeida, Gabriele M König
The marine-sponge-derived fungus Stachylidium sp. 293 K04 produces the N-methylated peptides endolide A (1) and endolide B (2), showing affinity for the vasopressin receptor 1A and serotonin receptor 5HT2B, respectively. Both peptides feature the rare amino acid 3-(3-furyl)alanine. Isotope labeling experiments, employing several (13)C-enriched precursors, revealed that this unprecedented heterocyclic amino acid moiety in endolide A (1) is synthesized from a cyclic intermediate of the shikimate pathway, but not from phenylalanine...
October 27, 2016: Journal of Natural Products
Mélissa Esposito, Louis-Félix Nothias, Hirsto Nedev, Jean-François Gallard, Pieter Leyssen, Pascal Retailleau, Jean Costa, Fanny Roussi, Bogdan I Iorga, Julien Paolini, Marc Litaudon
An efficient process was used to isolate six new jatrophane esters, euphodendroidins J (3), K (5), L (6), M, (8), N (10), and O (11), along with seven known diterpenoid esters, namely, euphodendroidins A (4), B (9), E (1), and F (2), jatrophane ester (7), and 3α-hydroxyterracinolides G and B (12 and 13), and terracinolides J and C (14 and 15) from the latex of Euphorbia dendroides. Their 2D structures and relative configurations were established by extensive NMR spectroscopic analysis. The absolute configurations of compounds 1, 11, and 15 were determined by X-ray diffraction analysis...
October 27, 2016: Journal of Natural Products
Tomasz Laskowski, Katarzyna Szwarc, Paweł Szczeblewski, Paweł Sowiński, Edward Borowski, Jan Pawlak
Herein, a new method for the elucidation of the absolute configuration of chiral secondary alcohols is proposed. This method is an alternative for a widely used approach reported by Mosher and Dale and similar methods that are based on the (1)H NMR shift (δ) changes of protons that are attached to the substituents of the oxymethine carbon atom. The presented method is not based on tracking the chemical shift changes and utilizes stereochemically defined monosaccharides as chiral probes. A secondary alcohol is glycosylated, and the resulting glycoside is subjected to NMR studies...
October 26, 2016: Journal of Natural Products
Yuki Hitora, Kentaro Takada, Yuji Ise, Shigeru Okada, Shigeki Matsunaga
LCMS analysis of the extract and a cytotoxicity assay of the HPLC fractions generated from a small-scale extract of a Lipastrotethya sp. marine sponge demonstrated the presence of bisindole alkaloids that were associated with the cytotoxic activity. Two bisindole alkaloids tethered by a guanidino ethylthiopyrazine moiety, dragmacidins G (1) and H (2), were isolated, and their structures were assigned by analysis of the MS and NMR data. They showed moderate cytotoxic activity against HeLa cells.
October 25, 2016: Journal of Natural Products
Katsunori Miyake, Airi Suzuki, Chihiro Morita, Masuo Goto, David J Newman, Barry R O'Keefe, Susan L Morris-Natschke, Kuo-Hsiung Lee, Kyoko Nakagawa-Goto
Seven new [acronyculatins I-O (1-7)] and four known acetophenone monomers were isolated from a CH3OH/CH2Cl2 (1:1) extract (N089419) of Acronychia trifoliolata provided by the U.S. National Cancer Institute (NCI, Frederick, MD, USA). Their structures were characterized by using various NMR and HRMS techniques. Among the known compounds, the structure of acronyculatin B (8) was revised. Some of the isolated compounds were evaluated for antiproliferative activity against human cancer cell lines. While most of the tested compounds were not cytotoxic, acronyculatins I (1) and J (2) showed moderate antiproliferative activity...
October 24, 2016: Journal of Natural Products
Choy-Eng Nge, Kae-Shin Sim, Siew-Huah Lim, Noel F Thomas, Yun-Yee Low, Toh-Seok Kam
Examination of the EtOH extract of the Malayan Tabernaemontana corymbosa resulted in the isolation of three new alkaloids, viz., cononuridine (1), an unusual hexacyclic, iboga-derived, monoterpenoid indole characterized by contraction of the tetrahydroazepine C-ring and incorporation of an additional isoxazolidine ring, taberisidine (2), a seco-corynanthean alkaloid, and conofolidine (3), an Aspidosperma-Aspidosperma bisindole that showed pronounced in vitro growth inhibitory activity against an array of human cancer cell lines, including KB, vincristine-resistant KB, PC-3, LNCaP, MCF7, MDA-MB-231, HT-29, and HCT 116 cells...
October 19, 2016: Journal of Natural Products
Yu-Ming Hsu, Fang-Rong Chang, I-Wen Lo, Kuei-Hung Lai, Mohamed El-Shazly, Tung-Ying Wu, Ying-Chi Du, Tsong-Long Hwang, Yuan-Bin Cheng, Yang-Chang Wu
Zoanthus kuroshio is a colorful zoanthid with a fluorescent pink oral disc and brown tentacles, which dominates certain parts of the Taiwanese and Japanese coasts. This sea anemone is a rich source of biologically active alkaloids. In the current investigation, two novel halogenated zoanthamines [5α-iodozoanthenamine (1) and 11β-chloro-11-deoxykuroshine A (2)], along with four new zoanthamines [18-epi-kuroshine A (3), 7α-hydroxykuroshine E (4), 5α-methoxykuroshine E (5), and 18-epi-kuroshine E (6)], and six known compounds were isolated from Z...
October 19, 2016: Journal of Natural Products
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