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Journal of Natural Products

Mario Wibowo, Qian Wang, Jeff Holst, Jonathan M White, Andreas Hofmann, Rohan A Davis
Seven new dihydro-β-agarofurans, celastrofurans A-G (1-7), along with two known secondary metabolites, 9β-benzoyloxy-1α-furoyloxydihydro-β-agarofuran (8) and (1R,2R,4R,5S,7R,9S,10R)-2-acetoxy-9-benzoyloxy-1-furoyloxydihydro-β-agarofuran (9), were obtained from the leaves of the Australian rainforest vine, Celastrus subspicata. The structures of the new compounds were determined by detailed spectroscopic (1D/2D NMR) and MS data analysis. The absolute configurations of compounds 1-4 were defined by ECD and single-crystal X-ray diffraction studies...
May 26, 2017: Journal of Natural Products
Cheng-Gang Zhang, Gui-Xin Chou, Xu-Dong Mao, Qing-Shan Yang, Jian-Li Zhou
Nepetaefolins A-J (1-10) and seven known compounds were isolated from the whole plant of Caryopteris nepetaefolia. The absolute configurations of 1-3 were determined from single-crystal X-ray diffraction and spectroscopic data. Compounds 6 and 7, with IC50 values of 6.3-9.0 μM, showed higher cytotoxicity than paclitaxel in one non-small-cell lung cancer, patient-derived xenograft (PDX) model when tested using PDX models and the adenosine triphosphate-tumor chemosensitivity assay (ATP-TCA).
May 26, 2017: Journal of Natural Products
Arihiro Iwasaki, Ikuma Shiota, Shimpei Sumimoto, Teruhiko Matsubara, Toshinori Sato, Kiyotake Suenaga
Kohamamides A, B, and C (1-3), new cyclic depsipeptides that belong to the kulolide superfamily, were isolated from an Okeania sp. marine cyanobacterium. Their structures were elucidated by spectroscopic analyses and degradation reactions. Kohamamide B (2) exhibited moderate cytotoxicity against HL60 cells. Although many natural products in the kulolide superfamily have been isolated from cyanobacteria collected in various parts of the world, kohamamides 1-3 are the first members to be isolated from the East Asian marine environment...
May 25, 2017: Journal of Natural Products
Ling-Yan Wang, Ming-Hua Chen, Jiang Wu, Hua Sun, Wei Liu, Yu-Hong Qu, Yan-Cheng Li, Yu-Zhuo Wu, Rui Li, Dan Zhang, Su-Juan Wang, Sheng Lin
The air-dried twigs of Litsea cubeba, a traditional Chinese medicinal tree, afforded 10 new aromatic glycosides (1-10) and 26 known analogues. Their structures were assigned by extensive 1D and 2D NMR experiments, and the absolute configurations were resolved by chemical methods, electronic circular dichroism, specific rotation, and X-ray crystallographic analysis. Compound 4 is the first example of a naturally occurring homoneolignan glucoside. Compounds 4, 6-8, and the known neolignan glucosides (11, 12, and 14) at respective 10 μM concentrations were found to reduce acetaminophen-induced HepG2 cell injury with 30...
May 25, 2017: Journal of Natural Products
Jehad Almaliti, Karla L Malloy, Evgenia Glukhov, Carmenza Spadafora, Marcelino Gutiérrez, William H Gerwick
A family of 2,2-dimethyl-3-hydroxy-7-octynoic acid (Dhoya)-containing cyclic depsipeptides, named dudawalamides A-D (1-4), was isolated from a Papua New Guinean field collection of the cyanobacterium Moorea producens using bioassay-guided and spectroscopic approaches. The planar structures of dudawalamides A-D were determined by a combination of 1D and 2D NMR experiments and MS analysis, whereas the absolute configurations were determined by X-ray crystallography, modified Marfey's analysis, chiral-phase GCMS, and chiral-phase HPLC...
May 23, 2017: Journal of Natural Products
Jinlian Zhao, Jiamin Feng, Zhen Tan, Jimei Liu, Jianyuan Zhao, Ridao Chen, Kebo Xie, Dewu Zhang, Yan Li, Liyan Yu, Xiaoguang Chen, Jungui Dai
Seven new phenylspirodrimane derivatives named stachybotrysins A-G (2-8), together with five known compounds (1, 9-12), were isolated from Stachybotrys chartarum CGMCC 3.5365. Stachybotrysin D (5) is the first reported example of a naturally occurring alcoholic O-sulfation of a phenylspirodrimane, and stachybotrysins F and G (7 and 8) are the first examples possessing an isobenzotetrahydrofuran ring with an acetonyl moiety attached. The structures of these compounds were elucidated on the basis of extensive spectroscopic data analysis and by comparison with reported data...
May 22, 2017: Journal of Natural Products
Marco Gargaro, Francesco Epifano, Serena Fiorito, Vito Alessandro Taddeo, Salvatore Genovese, Matteo Pirro, Antonella Turco, Paolo Puccetti, Carsten B Schmidt-Weber, Francesca Fallarino
The aryl hydrocarbon receptor (AhR) is a transcription factor activated by a vast array of natural and synthetic ligands. It plays a pivotal role in numerous physiological and pathological responses, such as cell proliferation and differentiation, induction of xenobiotic metabolizing enzymes, response to environmental toxins, and several others. In this study, we investigated the ability of some natural compounds (oxyprenylated ferulic acid and umbelliferone derivatives) and their semisynthetic analogues (e...
May 19, 2017: Journal of Natural Products
Antonietta Cerulli, Gianluigi Lauro, Milena Masullo, Vincenza Cantone, Beata Olas, Bogdan Kontek, Filomena Nazzaro, Giuseppe Bifulco, Sonia Piacente
The methanol extract of the leafy covers of Corylus avellana, source of the Italian PGI (protected geographical indication) product "Nocciola di Giffoni", afforded two new cyclic diarylheptanoids, giffonins T and U (2 and 3), along with two known cyclic diarylheptanoids, a quinic acid, flavonoid-, and citric acid derivatives. The structures of giffonins T and U were determined as highly hydroxylated cyclic diarylheptanoids by 1D and 2D NMR experiments. Their relative configurations were assigned by a combined quantum mechanical/NMR approach, comparing the experimental (13)C/(1)H NMR chemical shift data and the related predicted values...
May 18, 2017: Journal of Natural Products
Stephanie M Forget, Andrew W Robertson, David P Overy, Russell G Kerr, David L Jakeman
Angucycline antibiotics are composed of a classical four-ring angularly linked polyaromatic backbone. Differential cyclization chemistry of the A- and B-rings in jadomycin biosynthesis led to the discovery of two new furan analogues, while oxidation led to a ring-opened form of the jadomycin Nε-trifluoroacetyl-l-lysine (TFAL) congener. The compounds were isolated from Streptomyces venezuelae ISP5230 cultures grown with TFAL. Biosynthetic incorporation using d-[1-(13)C]-glucose in cultures enabled the unambiguous assignment of the aldehyde, alcohol, and amide functionalities present in these new congeners through NMR spectroscopy...
May 18, 2017: Journal of Natural Products
George Hsiao, Wei-Chiung Chi, Ka-Lai Pang, Jih-Jung Chen, Yueh-Hsiung Kuo, Yu-Kai Wang, Hyo-Jung Cha, Shen-Chieh Chou, Tzong-Huei Lee
The marine red alga Pterocladiella capillacea is an economic alga for the food industry in Taiwan, and its associated highly diversified fungi have not been investigated meticulously thus far. The EtOAc extract of the fermented broth of Chondrostereum sp. NTOU4196, a fungal strain isolated from P. capillacea, was found to exhibit significant nitric oxide (NO) production inhibitory activity in lipopolysaccharide-activated murine RAW 264.7 cells at a concentration of 100 μg/mL in the preliminary screening. Therefore, separation of the active principles from the fermented broths was performed, and that has led to the isolation of eight new 5,5,5-tricyclic hirsutane-type sesquiterpenes, namely, chondroterpenes A-H (1-8), together with seven known analogues...
May 17, 2017: Journal of Natural Products
Minghe Luo, Zhaomeng Cui, Hongbo Huang, Xianqin Song, Aijun Sun, Yongjun Dang, Laichun Lu, Jianhua Ju
Emodacidamides A-H (1-8), natural products featuring anthraquinone-amino acid conjugates, have been isolated from a marine-derived fungus, Penicillium sp. SCSIO sof101, together with known anthraquinones 9 and 10. The planar structures of 1-8 were elucidated using a combination of NMR spectroscopy and mass spectrometry. The absolute configurations of the amino acid residues were confirmed using Marfey's method and chiral-phase HPLC analyses. Additionally, isolates were evaluated for possible immunomodulatory and cytotoxic activities...
May 16, 2017: Journal of Natural Products
Lei Chen, Weiyun Chai, Wenling Wang, Tengfei Song, Xiao-Yuan Lian, Zhizhen Zhang
New bagremycins C-E (3-5) and bagrelactone A (6), together with known bagremycins A (1) and B (2), 4-hydroxystyrene (7), and 4-hydroxystyrene 4-O-α-d-galactopyranoside (8), were isolated from a mangrove-derived actinomycete, Streptomyces sp. Q22. Structures of these new compounds were elucidated based on their NMR and HRESIMS spectroscopic data as well as chemical degradation. Bagremycin C (3) is a unique analogue with an N-acetyl-(S)-cysteine moiety, while bagrelactone A (6) represents the first example of this type of bagremycin-derived macrolide...
May 15, 2017: Journal of Natural Products
Masahiko Isaka, Panida Chinthanom, Malipan Sappan, Sumalee Supothina, Vanicha Vichai, Kannawat Danwisetkanjana, Thitiya Boonpratuang, Kevin D Hyde, Rattaket Choeyklin
In a continuation of our research into antitubercular lanostane triterpenoids from submerged cultures of Ganoderma species, three strains, Ganoderma orbiforme BCC 22325, Ganoderma sp. BCC 60695, and Ganoderma australe BCC 22314, have been investigated. Fourteen new lanostane triterpenoids, together with 35 known compounds, were isolated. Antitubercular activities of these mycelium-associated Ganoderma lanostanoids against Mycobacterium tuberculosis H37Ra were evaluated. Taken together with the assay data of previously isolated compounds, structure-activity relationships of the antitubercular activity are proposed...
May 15, 2017: Journal of Natural Products
Luana Pulvirenti, Vera Muccilli, Nunzio Cardullo, Carmela Spatafora, Corrado Tringali
A chemoenzymatic synthesis of a small library of dimeric neolignans inspired by magnolol (1) is reported. The 2-iodoxybenzoic acid (IBX)-mediated regioselective ortho-hydroxylation of magnolol is described, affording the bisphenols 6 and 7. Further magnolol analogues (12, 13, 15-17, 19-23) were obtained from eugenol (3), tyrosol (4), and homovanillic alcohol (5), through horseradish peroxidase (HRP)-mediated oxidative coupling and regioselective ortho-hydroxylation or ortho-demethylation in the presence of IBX, followed by reductive treatment with Na2S2O4...
May 12, 2017: Journal of Natural Products
Dharmendra K Yadav, Yogesh P Bharitkar, Abhijit Hazra, Uttam Pal, Sugreev Verma, Sayantan Jana, Umesh P Singh, Nakul C Maiti, Nirup B Mondal, Snehasikta Swarnakar
Neem (Azadirachta indica) is a well-known medicinal and insecticidal plant. Although previous studies have reported the antiulcer activity of neem leaf extract, the lead compound is still unidentified. The present study reports tamarixetin 3-O-β-d-glucopyranoside (1) from a methanol extract of neem leaves and its gastroprotective activity in an animal model. Compound 1 showed significant protection against indomethacin-induced gastric ulceration in mice in a dose-dependent manner. Moreover, ex vivo and circular dichroism studies confirmed that 1 inhibited the enzyme matrix metalloproteinase-9 (MMP-9) activity with an IC50 value of ca...
May 11, 2017: Journal of Natural Products
Chun Gui, Shanwen Zhang, Xiangcheng Zhu, Wenjuan Ding, Hongbo Huang, Yu-Cheng Gu, Yanwen Duan, Jianhua Ju
Two new spirotetronate aglycones, 22-dehydroxymethyl-kijanolide (1) and 8-hydroxy-22-dehydroxymethyl-kijanolide (2), along with seven new spirotetronate glycosides, microsporanates A-F (3-8) and tetrocarcin P (9), together with three known tetrocarcins [tetrocarcins A (10), B (11), and AC6H (12)], were isolated from fermentation broths of the marine-derived Micromonospora harpali SCSIO GJ089. The structures of 1-9 were elucidated on the basis of 1D and 2D NMR and MS spectroscopic data. Compounds 3-8 feature an α,β-unsaturated carbonyl moiety within their spirotetronate skeletons...
May 10, 2017: Journal of Natural Products
Višnja Popović, Jan L Goeman, Nadia Bougarne, Sven Eyckerman, Arne Heyerick, Karolien De Bosscher, Johan Van der Eycken
Species of the genus Laserpitium have been used traditionally to treat inflammation and infection. From the herb of Laserpitium zernyi, six new compounds were isolated and their structures elucidated (using IR, NMR, HRMS data) as derivatives of 8-daucene-2,4,10-triol (1, 2, and 4), 7-daucene-2,4,10-triol (3), a lapiferin derivative featuring a C-2 ester moiety (5), and a daucane featuring an exomethylene group at C-8 (6). Also isolated were the rare daucanes vaginatin (7) and laserpitin (8). In a search for selective glucocorticoid receptor (GR) modulators, the compounds were tested for their capacity to inhibit NF-κB and AP-1 pro-inflammatory factors and for a potential competitive effect on a dexamethasone (Dex)-induced GR-driven glucocorticoid response element (GRE) reporter gene...
May 10, 2017: Journal of Natural Products
Teerayut Sriyatep, Raymond J Andersen, Brian O Patrick, Stephen G Pyne, Chatchai Muanprasat, Sawinee Seemakhan, Suparerk Borwornpinyo, Surat Laphookhieo
Seven new caged xanthones, doitunggarcinones E-K (1-7), all as scalemic mixtures and 10 known compounds (8-17), were isolated from the stem bark extract of Garcinia propinqua. The structures were elucidated on the basis of spectroscopic methods. The separation of the enantiomers of 1-6 was achieved by semipreparative chiral HPLC. The absolute configuration of compound (+)-1 was determined by single-crystal X-ray crystallographic analysis using Cu Kα radiation. The absolute configurations of the other related compounds were determined from comparisons of their ECD spectra with that of compound (+)-1...
May 10, 2017: Journal of Natural Products
Dieudonné Tshitenge Tshitenge, Doris Feineis, Suresh Awale, Gerhard Bringmann
From the tropical plant Gardenia ternifolia Schumach. and Thonn. (Rubiaceae), eight stereoisomeric 2,3-dihydrobenzo[b]furan neolignans, named gardenifolins A-H (1a-d and 2a-d), were isolated and fully structurally characterized. Reversed-phase chromatography of a stem bark extract afforded two peaks, viz. mixtures I and II, each one consisting of two diastereomers and their respective enantiomers. They were resolved and stereochemically analyzed by HPLC on a chiral phase coupled to electronic circular dichroism (ECD) spectroscopy, giving single ECD spectra of all eight stereoisomers...
May 10, 2017: Journal of Natural Products
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