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Journal of Natural Products

Hauke Löcken, Cinzia Clamor, Klaus Müller
Napabucasin (6) and its angularly anellated isomer (7), for which the synthesis is described, together with related plant-derived naphthoquinones, were evaluated in vitro against human breast cancer (MDA-MB-231) and chronic myelogenous leukemia (K562) cells. As observed for β-lapachone (3), the active naphthoquinones all induced apoptosis in a cell-cycle-independent fashion. In contrast to the pyran-fused β-lapachone (3), however, the most potent furan-fused naphthoquinones were able to redox cycle and generate superoxide in cell-based assays, which was independent of NAD(P)H:quinone oxido-reductase 1...
July 13, 2018: Journal of Natural Products
Muthiah Suresh, Anusueya Kumari, Debjit Das, Raj Bahadur Singh
The total synthesis of the phenolic sesquiterpene onitin using dimethylated indanone as the key intermediate is reported. Key to the success of this synthesis route is the Suzuki-Miyaura cross-coupling reaction of aryl bromide to introduce the vinyl side chain followed by formyl selective Wacker oxidation to generate the aldehyde. The target aldehyde was also obtained in high overall yield via an acid-catalyzed pinacol-pinacolone-type rearrangement of the epoxide. The epoxide was generated from oxidation of a styrene derivative by oxone...
July 12, 2018: Journal of Natural Products
Jiao Li, Hua Tang, Tibor Kurtán, Attila Mándi, Chun-Lin Zhuang, Li Su, Gui-Liang Zheng, Wen Zhang
Swinhoeisterols C-F (1-4), four new steroids having a rearranged 6/6/5/7 ring system, were isolated from the Xisha sponge Theonella swinhoei, together with the known analogue swinhoeisterol A (5). Their structures were determined based on spectroscopic analysis, TDDFT-ECD and optical rotation calculations, and biogenetic correlations. In an in vitro assay, compound 1 showed an inhibitory effect on (h)p300 with an IC50 value of 8.8 μM, whereas compounds 2-4 were not active.
July 10, 2018: Journal of Natural Products
Zhenzhen Zhang, Xueqian He, Guangwei Wu, Congcong Liu, Changjun Lu, Qianqun Gu, Qian Che, Tianjiao Zhu, Guojian Zhang, Dehai Li
Four new tetramic acids, cladosins H-K (1-4), and a related known compound, cladodionen (5), were isolated from the culture of the Mariana Trench (depth 6562 m) sediment-derived fungus Cladosporium sphaerospermum L3P3 treated with the histone deacetylase inhibitor SAHA (suberanilohydroxamic acid). Interestingly, compounds 1-5 existed as equilibrium E/ Z mixtures and 1-4 were the first cases of tetramic acids containing aniline moieties. Their structures including absolute configurations were elucidated through a combination of NMR, MS, and Mosher's method, together with the consideration of biogenetic origins...
July 9, 2018: Journal of Natural Products
Aisling Ní Cheallaigh, David J Mansell, Helen S Toogood, Shirley Tait, Antonios Lygidakis, Nigel S Scrutton, John M Gardiner
A chemoenzymatic approach providing access to all four intermediates in the peppermint biosynthetic pathway between limonene and menthone/isomenthone, including noncommercially available intermediates (-)- trans-isopiperitenol (2), (-)-isopiperitenone (3), and (+)- cis-isopulegone (4), is described. Oxidation of (+)-isopulegol (13) followed by enolate selenation and oxidative elimination steps provides (-)-isopiperitenone (3). A chemical reduction and separation route from (3) provides both native (-)- trans-isopiperitenol (2) and isomer (-)- cis-isopiperitenol (18), while enzymatic conjugate reduction of (-)-isopiperitenone (3) with IPR [(-)-isopiperitenone reductase)] provides (+)- cis-isopulegone (4)...
July 6, 2018: Journal of Natural Products
Pengcheng Yan, Daniel A Ritt, Katherine Zlotkowski, Heidi R Bokesch, William C Reinhold, John S Schneekloth, Deborah K Morrison, Kirk R Gustafson
Six new macrophilone-type pyrroloiminoquines were isolated and identified from an extract of the marine hydroid Macrorhynchia philippina. The proton-deficient and heteroatom-rich structures of macrophilones B-G (2-7) were elucidated by spectroscopic analysis and comparison of their data with those of the previously reported metabolite macrophilone A (1). Compounds 1-7 are the first pyrroloiminoquines to be reported from a hydroid. The macrophilones were shown to inhibit the enzymatic conjugation of SUMO to peptide substrates, and macrophilones A (1) and C (3) exhibit potent and selective cytotoxic properties in the NCI-60 anticancer screen...
July 6, 2018: Journal of Natural Products
Fang-Rong Chang, Pei-Shian Li, Rosa Huang Liu, Hao-Chun Hu, Tsong-Long Hwang, Jin-Ching Lee, Shu-Li Chen, Yang-Chang Wu, Yuan-Bin Cheng
Five new compounds named buxifoximes A-C (1-3), buxifobenzoate (4), and 7- O-(7'-peroxygeranyl) coumarin (5), together with 25 known compounds, were identified from the twigs of Atalantia buxifolia. Compounds 1-3 are unique secondary metabolites with the aldoxime functionality. The structures of the isolates were determined on the basis of spectroscopic data analyses, and the structure of 1 was confirmed by an X-ray single-crystallographic analysis. With respect to bioactivity, antidengue virus, anti-inflammatory, and cytotoxic activities of all purified compounds were tested and evaluated...
July 5, 2018: Journal of Natural Products
Katsuyuki Sakai, Tomoyasu Hirose, Masato Iwatsuki, Takumi Chinen, Toru Kimura, Takuya Suga, Kenichi Nonaka, Takuji Nakashima, Toshiaki Sunazuka, Takeo Usui, Yukihiro Asami, Satoshi O Mura, Kazuro Shiomi
The multidrug-sensitive budding yeast, Saccharomyces cerevisiae 12geneΔ0HSR-iERG6, is very useful in antifungal screens. A novel compound, named pestynol (1), was discovered from a culture of the fungus Pestalotiopsis humus FKI-7473 using the multidrug-sensitive yeast. The structure of 1 was elucidated by NMR studies and modified Mosher's method as (1 R,2 R,3 R,4 R)-( E)-5-(7,11-dimethyl-3-methylenedodeca-6,10-dien-1-yn-1-yl)cyclohex-5-ene-1,2,3,4-tetraol. Compound 1 showed antimicrobial activity against the Gram-positive bacteria, Klebsiella pneumoniae, and S...
July 5, 2018: Journal of Natural Products
Sarath P D Senadeera, Leonardo Lucantoni, Sandra Duffy, Vicky M Avery, Anthony R Carroll
The methanol extract of the flowers of the Australian eucalypt tree Corymbia torelliana yielded six new β-triketone-flavanone hybrids, torellianones A-F (1-6), the tetrahydroxycyclohexane torellianol A (7), and known β-triketones (4 S)-ficifolidione (8) and (4 R)-ficifolidione (9), and β-triketone-flavanones kunzeanone A (10) and kunzeanone B (11). Torellianones A and B, C and D, and E and F were each isolated as inseparable diastereomeric mixtures. Exchange correlations observed in a ROESY spectrum indicated that 5 and 6 also interconverted between stable conformers...
July 3, 2018: Journal of Natural Products
Florent Olivon, Louis-Félix Nothias, Vincent Dumontet, Pascal Retailleau, Sylvie Berger, Gilles Ferry, William Cohen, Bruno Pfeiffer, Jean A Boutin, Elisabeth Scalbert, Fanny Roussi, Marc Litaudon
In an effort to find potent natural inhibitors of RhoA and p115 signaling G-proteins, a systematic in vitro evaluation using enzymatic and plasmonic resonance assays was undertaken on 11 317 plant extracts. The screening procedure led to the selection of the New Caledonian endemic species Meiogyne baillonii for a chemical investigation. Using a bioguided isolation procedure, three enediyne-γ-butyrolactones (1-3) and two enediyne-γ-butenolides (4 and 5), named sapranthins H-L, respectively, two enediyne carboxylic acid (6 and 7), two depsidones, stictic acid (8) and baillonic acid (9), aristolactams AIa and AIIa (10 and 11), and two aporphines, dehydroroemerine (12) and noraristolodione (13), were isolated from the ethyl acetate extract of the bark...
July 3, 2018: Journal of Natural Products
Wenjing Wang, Jiaojiao Gong, Xiaorui Liu, Chong Dai, Yanyan Wang, Xiao-Nian Li, Jianping Wang, Zengwei Luo, Yuan Zhou, Yongbo Xue, Hucheng Zhu, Chunmei Chen, Yonghui Zhang
The cocultivation of Aspergillus flavipes and Chaetomium globosum, rich sources of cytochalasans, on solid rice medium, resulted in the production of 13 new, highly oxygenated cytochalasans, aspochalasinols A-D (1-4) and oxichaetoglobosins A-I (5-13), as well as seven known compounds (14-20). Of these compounds, 13 is a novel cytochalasan with an unexpected 2-norindole group. The isolated compounds were characterized by NMR spectroscopy, single-crystal X-ray crystallography, and ECD experiments. Compounds 1-4 represent the first examples of Asp-type cytochalasans with C-12 hydroxy groups, which may be a result of the coculture, as hydroxylated Me-12 groups are frequently found in Chae-type cytochalasans from C...
July 3, 2018: Journal of Natural Products
Hao-Bing Yu, Xiao-Li Wang, Yi-Xin Zhang, Wei-Heng Xu, Jian-Peng Zhang, Xiao-Yi Zhou, Xiao-Ling Lu, Xiao-Yu Liu, Bing-Hua Jiao
Seven new pimarane-type diterpene derivatives, libertellenones O-S (1-5) and eutypellenones A and B (6 and 7), together with two known compounds (8 and 9), were isolated from the culture of Eutypella sp. D-1 obtained from high-latitude soil of the Arctic. Their structures were elucidated from spectroscopic data, as well as experimental and calculated electronic circular dichroism (ECD) analysis. Structurally, compounds 1-5 possess a cyclopropyl-fused pimarane diterpene moiety, whereas compounds 6 and 7 share an unusual cyclobutyl-fused pimarane diterpene skeleton...
June 27, 2018: Journal of Natural Products
Yuki Kanamori, Arihiro Iwasaki, Shimpei Sumimoto, Teruhiko Matsubara, Toshinori Sato, Kiyotake Suenaga
Izenamides A, B, and C (1-3), new linear depsipeptides, were isolated from a taxonomically distinct marine cyanobacterium. Izenamides A and B contain a statine moiety [(3 S,4 S)-4-amino-3-hydroxy-6-methylheptanoic acid] and inhibited the activity of cathepsin D, an aspartic peptidase. Meanwhile, izenamides did not show growth-inhibitory activity against HeLa, HL60, or MCF-7 cells at up to 10 μM.
June 26, 2018: Journal of Natural Products
Raphael Reher, Markus Kuschak, Nina Heycke, Suvi Annala, Stefan Kehraus, Hao-Fu Dai, Christa E Müller, Evi Kostenis, Gabriele M König, Max Crüsemann
The cyclic depsipeptide FR900359 (FR), isolated from the traditional Chinese medicine plant Ardisia crenata, is a potent Gq protein inhibitor and thus a valuable tool to study Gq-mediated signaling of G protein-coupled receptors. Two new FR analogues (3 and 4) were isolated from A. crenata together with the known analogues 1 and 2. The structures of compounds 3 and 4 were established by NMR spectroscopic data and MS-based molecular networking followed by in-depth LCMS2 analysis. The latter approach led to the annotation of further FR analogues 5-9...
June 26, 2018: Journal of Natural Products
Hirofumi Akiyama, Chantra Indananda, Arinthip Thamchaipenet, Atsuko Motojima, Tsutomu Oikawa, Hisayuki Komaki, Akira Hosoyama, Akane Kimura, Naoya Oku, Yasuhiro Igarashi
Two new furanone-containing polyketides, linfuranones B and C, were isolated from a plant-associated actinomycete of the genus Sphaerimonospora. Their structures were determined by NMR and MS spectroscopic analyses, and the absolute configurations were established by anisotropic methods and chemical degradation approaches. In silico analysis of biosynthetic genes suggested that linfuranone B is generated from linfuranone C by oxidative cleavage of the polyketide chain. Linfuranones B and C induced preadipocyte differentiation into matured adipocytes at 20-40 μM without showing cytotoxicity...
June 25, 2018: Journal of Natural Products
Young Hye Seo, Ju-Hyun Jeon, Miran Jeong, Seung Mok Ryu, Won Kyung Jeon, Dae Sik Jang, Sang Hee Shim, Dongho Lee, Jung-Hye Choi, Jun Lee
Apios americana is an important food crop producing edible tubers with high nutritional and medicinal values and is widely cultivated in many countries. Despite its usefulness, research on its secondary metabolites and biological activities has been limited. In the present study, a new coumaronochromone, (2 R,3 S)-3,7,4'-trihydroxy-5-methoxycoumaronochromone (1), and two new isoflavone glucosides, 7,2',4'-trihydroxy-5-methoxyisoflavone-4'- O-β-d-glucopyranoside (3) and 5,7,4'-trihydroxyisoflavone-7- O-β-d-gentiotrioside (5), were isolated from the tubers of A...
June 22, 2018: Journal of Natural Products
Thiago F Martins, Ilka M Vasconcelos, Rodolpho G G Silva, Fredy D A Silva, Pedro F N Souza, Anna L N Varela, Louise M Albuquerque, Jose T A Oliveira
Staphylococcus aureus is a multidrug-resistant bacterium responsible for several cases of hospital-acquired infections, which constitute a global public health problem. The introduction of new healthcare strategies and/or the discovery of molecules capable of inhibiting the growth or killing S. aureus would have a huge impact on the treatment of S. aureus-mediated diseases. Herein, a Bowman-Birk protease inhibitor ( LzaBBI), with strong in vitro antibacterial activity against S. aureus, was purified to homogeneity from Luetzelburgia auriculata seeds...
June 21, 2018: Journal of Natural Products
Frederick Annang, Ignacio Pérez-Victoria, Guiomar Pérez-Moreno, Elizabeth Domingo, Ignacio González, José Rubén Tormo, Jesús Martín, Luis M Ruiz-Pérez, Olga Genilloud, Dolores González-Pacanowska, Francisca Vicente, Fernando Reyes
A potent antiplasmodial polycyclic xanthone, MDN-0185 (1), was isolated from an unidentified species of the genus Micromonospora. The planar structure of 1 was established as a seven-ring polycyclic xanthone with partial structures very similar to two known natural products, namely, xantholipin and Sch 54445. Using ROESY correlations, the relative stereochemistry of the two independent stereoclusters of compound 1 could be determined. Mosher analysis and comparison of the specific rotation of compound 1 with that of xantholipin allowed the determination of its absolute configuration...
June 20, 2018: Journal of Natural Products
Hai-Jun Hu, Yue Zhou, Zhu-Zhen Han, Yan-Hong Shi, Shu-Sheng Zhang, Zheng-Tao Wang, Li Yang
Twelve new abietane diterpenoids (1-12) and 31 known analogues (13-43) were isolated from a medicinal Chinese herb, Clerodendrum trichotomum Thunberg. The absolute configurations of 1-3 were established on the basis of ECD and X-ray crystallography data, whereas that of 4 was elucidated by comparison of experimental and calculated ECD data. Eight diterpenoids, 15,16-dehydroteuvincenone G (1), trichotomin A (4), 2α-hydrocaryopincaolide F (7), villosin C (20), 15-dehydro-17-hydroxycyrtophyllone A (22), demethylcryptojaponol (38), 6β-hydroxydemethylcryptojaponol (39), and trichotomone (43), exerted inhibitory effects against NO production with IC50 values of 5...
June 20, 2018: Journal of Natural Products
Nirmal K Chaudhary, John I Pitt, Ernest Lacey, Andrew Crombie, Daniel Vuong, Andrew M Piggott, Peter Karuso
Chemical investigation of an Australian fungus, Aspergillus banksianus, led to the isolation of the major metabolite banksialactone A (1), eight new isochromanones, banksialactones B-I (2-9), two new isocoumarins, banksiamarins A and B (10 and 11), and the reported compounds, clearanol I (12), dothideomynone A (13), questin (14), and endocrocin (15). The structures of 1-11 were established by NMR spectroscopic data analysis, and the absolute configurations were determined from optical rotations and ECD spectra in conjunction with TD-DFT calculations...
June 19, 2018: Journal of Natural Products
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