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Journal of Natural Products

Soleiman E Helaly, Samad Ashrafi, Rémy B Teponno, Steffen Bernecker, Abdelfattah A Dababat, Wolfgang Maier, Marc Stadler
The new cyclic lipodepsipeptide ophiotine (1), two new arthrichitin derivatives named arthrichitins B (4) and C (5), a new xanthocillin-like alkaloid, xanthomide Z (2), and the previously described arthrichitin (3) were isolated from the liquid culture broth of a nematode-associated fungus with affinities to the genus Ophiosphaerella. The structural elucidation and determination of the absolute configuration of the new molecules were accomplished using a combination of spectroscopic and chemical techniques, including 1D and 2D NMR, HRMS, and Marfey's analysis...
September 20, 2018: Journal of Natural Products
Peter E Cockram, Terry K Smith
Neglected tropical diseases caused by trypanosomatid parasites are a continuing and escalating problem, which devastate the less economically developed cultures in countries in which they are endemic by impairing both human and animal health. Current drugs for these diseases are regarded as out-of-date and expensive, with unacceptable side-effects and mounting parasite resistance, meaning there is an urgent need for new therapeutics. Natural products have long been a source of potent, structurally diverse bioactive molecules...
September 20, 2018: Journal of Natural Products
Chung Sub Kim, Joonseok Oh, Lalita Subedi, Sun Yeou Kim, Sang Un Choi, Kang Ro Lee
Six new thioglycosides (1-6) were characterized from the roots of Wasabia japonica along with a known analogue (7). Of these compounds, 1-3 possess a disulfide bridge connecting the carbohydrate motif and the aglycone, which is extremely rare in Nature. In particular, compound 1 forms an unusual 1,4,5-oxadithiocane ring system. The structures of the isolated compounds were determined through conventional NMR and HRMS data analysis procedure, and computational methods with advanced statistics were used for the configurational assignments of 1 and two pairs of inseparable epimers, 2/3 and 4/5...
September 20, 2018: Journal of Natural Products
Fredrick O Ojike, Nathalie Lavignac, Maxwell A Casely-Hayford
Combretastatin A-4 (CA-4) (1) is a plant-derived anticancer agent binding to the tubulin colchicine site. Polyunsaturated fatty acids (PUFAs) are readily taken up by cancer cells and have been used to improve cell targeting. In the present study, four CA-4-PUFA conjugates were synthesized by coupling combretastatin A-4 (1) with several polyunsaturated fatty acids. The conjugates (2a-d) were characterized using spectroscopic methods. Their cytotoxicity was evaluated against human breast cancer cells (MCF-7), and the inhibition of tubulin polymerization was determined in vitro...
September 19, 2018: Journal of Natural Products
Li Yang, Hanxiang Li, Ping Wu, Ahmed Mahal, Jinghua Xue, Liangxiong Xu, Xiaoyi Wei
Four new cyclodepsipeptides, dinghupeptins A-D (1-4), possessing a rare N5 -(2-hydroxylethyl)glutamine moiety, were isolated from cultures of the soil-derived Streptomyces sp. SC0581. Their structures were elucidated by spectroscopic and advanced Marfey's amino acid analysis, and their 3D structures were established by theoretical conformational analysis. Compounds 1 and 2, containing a 3-amino-6-hydroxypiperidone unit, displayed selective inhibition of chymotrypsin with IC50 values of 2.1 and 1.1 μM, respectively...
September 17, 2018: Journal of Natural Products
Tomas Zimmermann, Henrik Franzyk, Søren Brøgger Christensen
An alternative procedure for isolation of 4β-phorbol from seeds of Croton tiglium has been developed, and an artifact containing a furan ring formed by rearrangement of 12,13,20- O-triacylated phorbol derivatives into (6b S,7 R,8 R,8a S)-2-(hydroxymethyl)-5,7,9,9-tetramethyl-3,7,8,9,9a,9b-hexahydrocyclopropa[3',4']benzo[1',2':3,4]cyclohepta[1,2- b]furan-6b,8,8a-triol (8a) has been characterized. A mechanism involving an oxidative rearrangement and a decarboxylation for formation of the artifact is proposed...
September 14, 2018: Journal of Natural Products
Nikhil B Ghate, Dipankar Chaudhuri, Sourav Panja, Sudhir S Singh, Gajendra Gupta, Chang Yeon Lee, Nripendranath Mandal
The search for new plant-based anti-inflammatory drugs continues in order to overcome the detrimental side effects of conventional anti-inflammatory agents, both steroidal and nonsteroidal. This study involves the quinoline SPE2, 7-hydroxy-6-methoxyquinolin-2(1 H)-one, isolated from the EtOAc fraction of Spondias pinnata bark. Structure elucidation was done using analytical spectroscopic methods including Fourier transform infrared spectroscopy, high-resolution electrospray ionization mass spectrometry, nuclear magnetic resonance spectroscopy, and single-crystal X-ray crystallography...
September 14, 2018: Journal of Natural Products
Ye Ye, Drolma Dawa, Guang-Hui Liu, Min Zhao, Dorje Tseden, Yu-Cheng Gu, Li-Sheng Ding, Zhi-Xing Cao, Yan Zhou
Twenty-two new sesquiterpenoids with four skeletal types and 15 known analogues were isolated from the whole plants of Ligularia rumicifolia. The structures of the isolates were elucidated based on comprehensive spectroscopic data analysis. Compound 1 is a C14 nor-sesquiterpenoid featuring a 6/6/6 tricyclic skeleton with a 9,13-ether bridge. The absolute configuration of 2 was established through single-crystal X-ray diffraction data. Compounds 13-16 exhibited in vitro antiproliferative activity against the four human tumor cell lines A-549, HGC-27, HeLa, and MV4-11...
September 13, 2018: Journal of Natural Products
Yong-Jun Jiang, Da-Shan Zhang, Hao-Jian Zhang, Jia-Qi Li, Wan-Jing Ding, Cheng-Dong Xu, Zhong-Jun Ma
Four new medermycin-type naphthoquinones, strepoxepinmycins A-D (1-4), and one known compound, medermycin (5), were identified from Streptomyces sp. XMA39. Their structures were elucidated by analysis of HRESIMS, 1D and 2D NMR spectroscopic data, and ECD calculations. Among these compounds, strepoxepinmycin A (1) represents a rare 5,10-oxepindione ring system typically formed by a Baeyer-Villiger oxidation, and strepoxepinmycin B (2) is an isolation artifact derived from 1. Bioactivity evaluations of these compounds showed that compounds 3 and 4 exhibited cytotoxicity against HCT-116 and PC-3 cancer cell lines and 4 exhibited moderate inhibition of ROCK 2 protein kinase...
September 13, 2018: Journal of Natural Products
Jun-Pil Jang, Gwi Ja Hwang, Mina Jang, Shunji Takahashi, Sung-Kyun Ko, Hiroyuki Osada, Jae-Hyuk Jang, Jong Seog Ahn
A chemical investigation of a culture extract from a soil-derived Streptomyces sp. RK88-1441 led to the isolation and characterization of two new glycosylated anthraquinones, aturanosides A (1) and B (2), and a new anthraquinone derivative, aturanocin (3). The structures of these compounds were elucidated by detailed NMR and MS spectroscopic analyses. The absolute configurations of the sugar units, based on the magnitudes of the coupling constants, ROESY correlations, and chemical derivatization, from 1 and 2 are 6- O-[ N-acetyl-α-d-glucosamino-(1→2)-α-l-rhamnoside] and 6- O-α-l-rhamnoside, respectively...
September 12, 2018: Journal of Natural Products
Luca Pompermaier, Elke H Heiss, Mostafa Alilou, Fabian Mayr, Mawunu Monizi, Thea Lautenschlaeger, Daniela Schuster, Stefan Schwaiger, Hermann Stuppner
Six new and four known dihydrochalcone glucoside derivatives (1-10), the phenylpropanoid coniferin (11), and the lignans (+)-pinoresinol (12) and lariciresinol (13) were isolated from the subaerial plant parts of Thonningia sanguinea in the course of a screening campaign for new antidiabetic lead compounds. The structures of the new substances were elucidated by HRESIMS, NMR, GC-MS, and ECD data evaluation. 2'- O-(3-Galloyl-4,6- O- Sa -hexahydroxydiphenoyl-β-d-glucopyranosyl)-3-hydroxyphloretin (4), 2'- O-(4,6- O- Sa -hexahydroxydiphenoyl-β-d-glucopyranosyl)phloretin (5), 2'- O-(3- O-galloyl-4,6- O- Sa -hexahydroxydiphenoyl-β-d-glucopyranosyl)phloretin (6), and thonningianin B (9) showed moderate protein tyrosine phosphatase-1B inhibition in an enzyme assay (IC50 values ranging from 19 to 25 μM), whereas thonningianin A (10) was identified as a more potent inhibitor (IC50 = 4...
September 12, 2018: Journal of Natural Products
Shasha Zhang, Xia Wang, Jin Hao, Dangdang Li, René Csuk, Shengkun Li
The efficient synthesis and antifungal exploration of (+)-yahazunol and related natural products are described. Central to this strategy is the Barton decarboxylative coupling, comprising a one-pot radical decarboxylation and quinone addition cascade. The scalable synthesis of (+)-yahazunol was accomplished in five longest linear sequences (LLS) starting from commercially available and inexpensive (-)-sclareol. The divergent translational potential of (+)-yahazunol was demonstrated by the expedient preparation of (-)-zonarone, (-)-isozonarone, (-)-zonarol, (-)-isozonarol, (+)-chromazonarol, and (+)-yahazunone...
September 12, 2018: Journal of Natural Products
Thuc-Huy Duong, Mehdi A Beniddir, Van-Kieu Nguyen, Thammarat Aree, Jean-François Gallard, Dinh-Hung Mac, Huu-Hung Nguyen, Xuan-Hao Bui, Joël Boustie, Kim-Phi-Phung Nguyen, Warinthorn Chavasiri, Pierre Le Pogam
Six new sulfonic acid-containing flavonoids, acidoflavanone (1), acidoauronol (2), 5- O-methylacidoauronol (3), acidoaurone (4), acidoisoflavone (5), and acidoflavonol (6), were isolated from the EtOH extract of the roots of Phyllanthus acidus. Their structures were unambiguously established by interpretation of their HRESIMS and 1D and 2D NMR data, single-crystal X-ray diffraction analysis, and comparison to the literature data. These new structures represent the first examples of sulfonic acid-containing flavanones, auronols, aurones, and isoflavones...
September 12, 2018: Journal of Natural Products
Changxing Qi, Mengting Liu, Qun Zhou, Weixi Gao, Chunmei Chen, Yongji Lai, Zhengxi Hu, Yongbo Xue, Jinwen Zhang, Dongyan Li, Xiao-Nian Li, Qing Zhang, Jianping Wang, Hucheng Zhu, Yonghui Zhang
Sixteen 3,5-dimethylorsellinic acid-based (DMOA-based) meroterpenoids, including 10 new compounds, asperterpenes D-M (1-10), were obtained from Aspergillus terreus. The structures and absolute configurations of the new compounds were confirmed by extensive spectroscopy, single-crystal X-ray diffraction analysis, and experimental electronic circular dichroism (ECD) measurements. Compounds 2, 3, and 7 are the first 3,5-dimethylorsellinic acid-based meroterpenoids possessing a unique cis-fused A/B ring system...
September 12, 2018: Journal of Natural Products
Shibdas Banerjee, Elumalai Gnanamani, Stephen R Lynch, Fernando Zamudio Zuñiga, Juana María Jiménez-Vargas, Lourival Domingos Possani, Richard N Zare
No abstract text is available yet for this article.
September 11, 2018: Journal of Natural Products
Ricardo J Ferreira, Annamária Kincses, Márió Gajdács, Gabriella Spengler, Daniel J V A Dos Santos, Joseph Molnár, Maria-José U Ferreira
The phytochemical study of Euphorbia pedroi led to the isolation of a new tetracyclic triterpenoid with an unusual spiro scaffold, spiropedroxodiol (1), along with seven known terpenoids (2-8). Aiming at obtaining compounds with improved multidrug-resistance (MDR) reversal activity, compound 8, an ent-abietane diterpene, was derivatized by introducing nitrogen-containing and aromatic moieties, yielding compounds 9-14. The structures of compounds were characterized by detailed spectroscopic analysis, including 2D NMR experiments (COSY, HMQC/HSQC, HMBC, and NOESY)...
September 10, 2018: Journal of Natural Products
Jung-Ho Lee, Matthew Dean, Julia R Austin, Joanna E Burdette, Brian T Murphy
The use of botanical dietary supplements is becoming increasingly popular for the alleviation of hormonal-based conditions such as hot flashes, premenstrual syndrome, and fertility. Estrogen and progesterone receptors (ER and PR) play an essential role in these processes. However, despite the fact that many therapies used to alleviate gynecological conditions act through PR-mediated mechanisms, few studies have investigated or identified any herbal natural product components that act on this receptor. In the current study, we used a progesterone response element (PRE)-luciferase (Luc) reporter assay to identify four phytoprogestins present in a standardized red clover ( Trifolium pratense) extract...
September 10, 2018: Journal of Natural Products
Camila M Crnkovic, Aleksej Krunic, Daniel S May, Tyler A Wilson, Diana Kao, Joanna E Burdette, James R Fuchs, Nicholas H Oberlies, Jimmy Orjala
Cyanobacteria are a source of chemically diverse metabolites with potential medicinal and biotechnological applications. Rapid identification of compounds is central to expedite the natural product discovery process. Mass spectrometry has been shown to be an important tool for dereplication of complex natural product samples. In addition, chromatographic separation and complementary spectroscopic analysis (e.g., UV) can enhance the confidence of the dereplication process. Here, we applied a droplet-liquid microjunction-surface sampling probe (droplet probe) coupled with UPLC-PDA-HRMS-MS/MS to identify two new natural products in situ from the freshwater strain Calothrix sp...
September 7, 2018: Journal of Natural Products
Catalina Rozo-Lugo, Luis Enrique Cuca-Suárez, Thomas J Schmidt, Ericsson Coy-Barrera
Three new tetrahydrobenzofuran-6(2 H)-one-type neolignans, heterochromins A-C (1-3), along with a bicyclo[3.2.1]octane neolignan, cinerin C (4), were isolated from an ethanol extract from the leaves of Ocotea heterochroma, a native plant growing in the Colombo-Ecuadorian region of the Andes. The chemical structures of 1-3 were elucidated by spectroscopic methods. The platelet activating factor (PAF) antagonistic activity was tested in vitro for these compounds. Additionally, their binding mode to the PAF receptor was studied by molecular docking and molecular dynamics simulations in order to rationalize such activity...
September 6, 2018: Journal of Natural Products
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