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Journal of Natural Products

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https://www.readbyqxmd.com/read/28641017/nanpdb-a-resource-for-natural-products-from-northern-african-sources
#1
Fidele Ntie-Kang, Kiran K Telukunta, Kersten Döring, Conrad V Simoben, Aurélien F A Moumbock, Yvette I Malange, Leonel E Njume, Joseph N Yong, Wolfgang Sippl, Stefan Günther
Natural products (NPs) are often regarded as sources of drugs or drug leads or simply as a "source of inspiration" for the discovery of novel drugs. We have built the Northern African Natural Products Database (NANPDB) by collecting information on ∼4500 NPs, covering literature data for the period from 1962 to 2016. The data cover compounds isolated mainly from plants, with contributions from some endophyte, animal (e.g., coral), fungal, and bacterial sources. The compounds were identified from 617 source species, belonging to 146 families...
June 22, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28636395/synthesis-of-the-marine-myxobacterial-antibiotic-enhygrolide-a
#2
Ramesh Muddala, Jaime A M Acosta, Luiz C A Barbosa, John Boukouvalas
The first synthesis of enhygrolide A, a scarce γ-alkylidenebutenolide antibiotic of the obligate marine myxobacterium Enhygromyxa salina, was achieved in five steps and 54% overall yield from tetronic acid. Key steps include (i) organocatalytic reductive alkylation, (ii) iron-catalyzed sp(2)-sp(3) cross-coupling, and (iii) vinylogous aldol condensation. Aside from its brevity and reliance on environmentally sustainable processes, the synthesis demonstrates the serviceability of butenolide pivalates in cross-coupling reactions...
June 21, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28636357/correction-to-%C3%AE-glucosidase-inhibitory-and-cytotoxic-taxane-diterpenoids-from-the-stem-bark-of-taxus-wallichiana
#3
Phu Hoang Dang, Hai Xuan Nguyen, Truc Thanh Thi Duong, Thao Kim Thi Tran, Phuc Thi Nguyen, Trang Kieu Thi Vu, Hung Chi Vuong, Nguyen Huu Trong Phan, Mai Thanh Thi Nguyen, Nhan Trung Nguyen, Suresh Awale
No abstract text is available yet for this article.
June 21, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28636352/prevention-of-marine-biofouling-using-the-natural-allelopathic-compound-batatasin-iii-and-synthetic-analogues
#4
Lindon W K Moodie, Rozenn Trepos, Gunnar Cervin, Kari Anne Bråthen, Bente Lindgård, Rigmor Reiersen, Patrick Cahill, Henrik Pavia, Claire Hellio, Johan Svenson
The current study reports the first comprehensive evaluation of a class of allelopathic terrestrial natural products as antifoulants in a marine setting. To investigate the antifouling potential of the natural dihydrostilbene scaffold, a library of 22 synthetic dihydrostilbenes with varying substitution patterns, many of which occur naturally in terrestrial plants, were prepared and assessed for their antifouling capacity. The compounds were evaluated in an extensive screen against 16 fouling marine organisms...
June 21, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28627872/xanthohumol-blocks-proliferation-and-migration-of-vascular-smooth-muscle-cells-in-vitro-and-reduces-neointima-formation-in-vivo
#5
Rongxia Liu, Elke H Heiss, Daniel Schachner, Baohong Jiang, Wanhui Liu, Johannes M Breuss, Verena M Dirsch, Atanas G Atanasov
Xanthohumol (1) is a principal prenylated chalcone found in hops. The aim of this study was to examine its influence on platelet-derived growth factor (PDGF)-BB-triggered vascular smooth muscle cell (VSMC) proliferation and migration in vitro and on experimentally induced neointima formation in vivo. Quantification of resazurin conversion indicated that 1 can inhibit PDGF-BB-induced VSMC proliferation concentration-dependently (IC50 = 3.49 μM). Furthermore, in a wound-healing assay 1 potently suppresses PDGF-BB-induced VSMC migration at 15 μM...
June 19, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28621949/cyclotides-from-the-indian-medicinal-plant-viola-odorata-banafsha-identification-and-characterization
#6
M Narayani, Anju Chadha, Smita Srivastava
Cyclotides are cyclic cystine knotted macrocyclic plant peptides that have several promising applications. This study was undertaken to detect and identify known and new cyclotides in Viola odorata, a commercially important medicinal plant, from three geographical locations in India. The number of cyclotides in the plant varied with the tissue (leaves, petioles, flowers, runners, and roots) and with geographical locations in India. Using liquid chromatography coupled to Fourier transform mass spectrometry (FTMS), 166 cyclotide-like masses were observed to display cyclotide-diagnostic mass shifts following reduction, alkylation, and digestion, and 71 of these were positively identified based on automated spectrum matching...
June 16, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28621943/natural-products-discovered-in-a-high-throughput-screen-identified-as-inhibitors-of-rgs17-and-as-cytostatic-and-cytotoxic-agents-for-lung-and-prostate-cancer-cell-lines
#7
Christopher R Bodle, Duncan I Mackie, Michael P Hayes, Josephine H Schamp, Michael R Miller, Michael D Henry, Jonathan A Doorn, Jon C D Houtman, Michael A James, David L Roman
Regulator of G Protein Signaling (RGS) 17 is an overexpressed promoter of cancer survival in lung and prostate tumors, the knockdown of which results in decreased tumor cell proliferation in vitro. Identification of drug-like molecules inhibiting this protein could ameliorate the RGS17's pro-tumorigenic effect. Using high-throughput screening, a chemical library containing natural products was interrogated for inhibition of the RGS17-Gαo interaction. Initial hits were verified in control and counter screens...
June 16, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28621941/sulawesins-a-c-furanosesterterpene-tetronic-acids-that-inhibit-usp7-from-a-psammocinia-sp-marine-sponge
#8
Ahmed H Afifi, Ippei Kagiyama, Ahmed H El-Desoky, Hikaru Kato, Remy E P Mangindaan, Nicole J de Voogd, Nagwa M Ammar, Mohammed S Hifnawy, Sachiko Tsukamoto
Three new furanosesterterpene tetronic acids, sulawesins A-C (1-3), were isolated from a Psammocinia sp. marine sponge, along with the known compounds ircinins-1 (4) and -2 (5). Although ircinins-1 and -2 were previously isolated as (+)- or (-)-enantiomers from marine sponges, we isolated them as enantiomeric mixtures. Sulawesins A and B possess a new carbon skeleton with a 5-(furan-3-yl)-4-hydroxycyclopent-2-enone moiety and were also found to be diastereomeric mixtures of four isomers by an HPLC analysis with a chiral-phase column...
June 16, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28621938/inhibition-of-proliferation-of-vascular-smooth-muscle-cells-by-cucurbitanes-from-momordica-charantia
#9
Nguyen Quoc Tuan, Do-Hyung Lee, Joonseok Oh, Chung Sub Kim, Kyung-Sun Heo, Chang-Seon Myung, MinKyun Na
The cucurbitaceous plant Momordica charantia L., named "bitter melon", inhabits Asia, Africa, and South America and has been used as a traditional medicine. The atypical proliferation of vascular smooth muscle cells (VSMCs) plays an important role in triggering the pathogenesis of cardiovascular diseases. Platelet-derived growth factor (PDGF) is regarded as the most powerful growth factor in promoting the intimal accumulation of VSMCs. The current study features the identification of six new cucurbitane-type triterpenoids (1-6) from the fruits of M...
June 16, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28617598/withanolides-from-aeroponically-grown-physalis-peruviana-and-their-selective-cytotoxicity-to-prostate-cancer-and-renal-carcinoma-cells
#10
Ya-Ming Xu, E M Kithsiri Wijeratne, Ashley L Babyak, Hanna R Marks, Alan D Brooks, Poonam Tewary, Li-Jiang Xuan, Wen-Qiong Wang, Thomas J Sayers, A A Leslie Gunatilaka
Investigation of aeroponically grown Physalis peruviana resulted in the isolation of 11 new withanolides, including perulactones I-L (1-4), 17-deoxy-23β-hydroxywithanolide E (5), 23β-hydroxywithanolide E (6), 4-deoxyphyperunolide A (7), 7β-hydroxywithanolide F (8), 7β-hydroxy-17-epi-withanolide K (9), 24,25-dihydro-23β,28-dihydroxywithanolide G (10), and 24,25-dihydrowithanolide E (11), together with 14 known withanolides (12-25). The structures of 1-11 were elucidated by the analysis of their spectroscopic data, and 12-25 were identified by comparison of their spectroscopic data with those reported...
June 15, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28616931/database-for-rapid-dereplication-of-known-natural-products-using-data-from-ms-and-fast-nmr-experiments
#11
Carlos L Zani, Anthony R Carroll
The discovery of novel and/or new bioactive natural products from biota sources is often confounded by the reisolation of known natural products. Dereplication strategies that involve the analysis of NMR and MS spectroscopic data to infer structural features present in purified natural products in combination with database searches of these substructures provide an efficient method to rapidly identify known natural products. Unfortunately this strategy has been hampered by the lack of publically available and comprehensive natural product databases and open source cheminformatics tools...
June 15, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28613872/detection-of-a-toxic-methylated-derivative-of-phomopsin-a-produced-by-the-legume-infesting-fungus-diaporthe-toxica
#12
Svenja Schloß, Thomas Hackl, Corinna Herz, Evelyn Lamy, Matthias Koch, Sascha Rohn, Ronald Maul
Phomopsin A (PHO-A), produced by the fungus Diaporthe toxica, is a mycotoxin known to be responsible for fatal liver disease of lupin-fed sheep. The full spectrum of the toxic secondary metabolites produced by D. toxica is still unknown. PHO-A and the naturally occurring derivatives B-E have been subject to several studies to reveal their structures as well as chemical and toxicological properties. In this work, a methylated derivative (1) of PHO-A isolated from lupin seeds inoculated with D. toxica is described...
June 14, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28613071/potent-inhibitor-of-drug-resistant-hiv-1-strains-identified-from-the-medicinal-plant-justicia-gendarussa
#13
Hong-Jie Zhang, Emily Rumschlag-Booms, Yi-Fu Guan, Dong-Ying Wang, Kang-Lun Liu, Wan-Fei Li, Van H Nguyen, Nguyen M Cuong, Djaja D Soejarto, Harry H S Fong, Lijun Rong
Justicia gendarussa, a medicinal plant collected in Vietnam, was identified as a potent anti-HIV-1 active lead from the evaluation of over 4500 plant extracts. Bioassay-guided separation of the extracts of the stems and roots of this plant led to the isolation of an anti-HIV arylnaphthalene lignan (ANL) glycoside, patentiflorin A (1). Evaluation of the compound against both the M- and T-tropic HIV-1 isolates showed it to possess a significantly higher inhibition effect than the clinically used anti-HIV drug AZT...
June 14, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28609099/botrysphones-a-c-and-botrysphins-a-f-triketides-and-diterpenoids-from-the-fungus-botrysphaeria-laricina
#14
Peng-Liang Zhang, Yang Han, Long-Teng Zhang, Xiao-Ling Wang, Tao Shen, Dongmei Ren, Hongxiang Lou, Xiao-Ning Wang
Three new triketides, botrysphones A-C (1-3) and six new isopimarane-type diterpenoids, botrysphins A-F (4-9), together with the known triketides sphaeropsidone (10) and chlorosphaeropsidone (11) and diterpenoids sphaeropsidins A and B (12 and 13), were obtained from culture of the fungus Botrysphaeria laricina associated with the moss Rhodobryum umgiganteum. The structures of the new compounds were established on the basis of extensive spectroscopic techniques including HRMS and 1D and 2D NMR data. Compounds 7 and 12 showed significant quinone reductase inducing activity in Hepa 1c1c7 cells...
June 13, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28598633/ochracenes-a-i-humulane-derived-sesquiterpenoids-from-the-antarctic-fungus-aspergillus-ochraceopetaliformis
#15
Junfeng Wang, Weijun He, Fandong Kong, Xinpeng Tian, Pei Wang, Xiaojiang Zhou, Yonghong Liu
Nine new humulane-derived sesquiterpenoids, ochracenes A-I (1-9), were isolated from the Antarctic fungus Aspergillus ochraceopetaliformis SCSIO 05702. Their structures including absolute configurations were elucidated on the basis of spectroscopic analysis, Mosher's method, and electronic circular dichroism analysis. Compared with previous humulane-type sesquiterpenoids, ochracenes A-I (1-9) featured novel carbon skeletons with corresponding methyl migration, ring cleavage, and carbon loss. Two unprecedented 8,9-secocyclic sesquiterpenoids (2 and 3) exhibited inhibitory effects on lipopolysaccharide-induced NO release in RAW 264...
June 9, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28598616/identification-of-bmi1-promoter-inhibitors-from-beaumontia-murtonii-and-eugenia-operculata
#16
Yui Kaneta, Midori A Arai, Naoki Ishikawa, Kazufumi Toume, Takashi Koyano, Thaworn Kowithayakorn, Tetsuhiro Chiba, Atsushi Iwama, Masami Ishibashi
B-Cell-specific Moloney murine leukemia virus insertion region 1 (BMI1) is a core component of the polycomb repressive complex 1 (PRC1). Abnormal expression of BMI1 is associated with a number of human malignances and cancer stem cells (CSCs), which cause chemotherapy resistance. Therefore, small molecules that inhibit BMI1 expression are potential candidates for cancer therapy. In this study, a cell-based reporter gene assay was developed that allowed BMI1 promoter activity to be measured in 293T human embryonic kidney cells based on luciferase expression levels...
June 9, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28598175/naphthoquinones-of-sinningia-reitzii-and-anti-inflammatory-antinociceptive-activities-of-8-hydroxydehydrodunnione
#17
Adson S Soares, Felipe L Barbosa, André L Rüdiger, David L Hughes, Marcos J Salvador, Aleksander R Zampronio, Maria Élida A Stefanello
Chemical investigation of the tubers of Sinningia reitzii led to the isolation of five new naphthoquinones, 8-hydroxydehydrodunnione (1), 7-hydroxydehydrodunnione (2), 5-hydroxy-6,7-dimethoxy-α-dunnione (3), 5-hydroxy-6,7-dimethoxydunniol (4), and 8-hydroxy-7-methoxy-2-O-methylstreptocarpone (5). Three known naphthoquinones, 7-hydroxy-α-dunnione, 8-hydroxydunnione, and 6,8-dihydroxy-7-methoxy-2-O-methyldunniol, were also identified. When tested for anti-inflammatory activity in a mouse model, compound 1 (50-500 pg/paw) reduced the edema induced by carrageenan in a dose-dependent fashion...
June 9, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28594169/biosynthesis-of-fluorinated-peptaibols-using-a-site-directed-building-block-incorporation-approach
#18
José Rivera-Chávez, Huzefa A Raja, Tyler N Graf, Joanna E Burdette, Cedric J Pearce, Nicholas H Oberlies
Synthetic biological approaches, such as site-directed biosynthesis, have contributed to the expansion of the chemical space of natural products, making possible the biosynthesis of unnatural metabolites that otherwise would be difficult to access. Such methods may allow the incorporation of fluorine, an atom rarely found in nature, into complex secondary metabolites. Organofluorine compounds and secondary metabolites have both played pivotal roles in the development of drugs; however, their discovery and development are often via nonintersecting tracks...
June 8, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28590734/derivatives-of-the-lignan-7-hydroxymatairesinol-with-antioxidant-properties-and-enhanced-lipophilicity
#19
Thomas Moraux, Stéphane Dumarçay, Philippe Gérardin, Christine Gérardin-Charbonnier
The lignan 7'-hydroxymatairesinol (1), extracted from the knotwoods of fir (Abies alba), spruce (Picea abies), and Douglas fir (Pseudotsuga menziesii), exhibited unexpected reactivity when esterification reactions were attempted on the hydroxy group at position C-7'. To circumvent the rapid intramolecular cyclization procedure, leading quantitatively to the lignan conidendrin (7), a simple strategy for 7'-esterification of 1 under mild conditions (three steps, up to 80% overall yield) was developed. Compared to hydroxymatairesinol (1) (log K'w = 1...
June 7, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28590124/terpenoids-from-euphorbia-soongarica-and-their-multidrug-resistance-reversal-activity
#20
Jie Gao, Haji A Aisa
Ten new terpenoids, including five diterpenoids (1-5), three nortriterpenoids (6-8), and two triterpenoids (9, 10), and 15 known terpenoids (11-25) were isolated from an acetone extract of Euphorbia soongarica. Sooneuphoramine (1) is the first example of a euphoractine B-type diterpenoid alkaloid, while sooneuphanones A-C (6-8) are rare nortriterpenoids from the Euphorbia genus. The isolated terpenoids were tested for their cytotoxicity and multidrug resistance (MDR) reversal activity, 10 of which showed moderate cytotoxicity against the KB and KBv200 cell lines, while 11 compounds exhibited P-gp modulating potential...
June 7, 2017: Journal of Natural Products
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