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Journal of Natural Products

Njogu M Kimani, Josphat C Matasyoh, Marcel Kaiser, Reto Brun, Thomas J Schmidt
In continuation of a search for new antiprotozoal agents from plants of the family Asteraceae, Tarchonanthus camphoratus and Schkuhria pinnata have been investigated. By following the promising in vitro activity of the dichloromethane extracts from their aerial parts, bioassay-guided chromatographic isolation yielded two known sesquiterpene lactones (1 and 2) from T. camphoratus and 20 known compounds of this type from S. pinnata. From the latter, a new eudesmanolide, (1R*,5S*,6R*,7R*,8R*,10R*)-1-hydroxy-8-[5″-hydroxy-4'-(2″-hydroxyisovaleroyloxy)tigloyloxy]-3-oxoeudesma-11(13)-en-6,12-olide (3), and two new germacranolides, 3β-(2″-hydroxyisovaleroyloxy)-8β-(3-furoyloxy)costunolide (14) and 1(10)-epoxy-3β-hydroxy-8β-[5'-hydroxy-4'-(2″-hydroxyisovaleroyloxy)tigloyloxy]costunolide (16), were obtained...
December 15, 2017: Journal of Natural Products
Tappey H Jones, Dylan M Guthrie, Conor T Hogan, Donovan J Robinson, Robert Mesibov, William A Shear, Thomas F Spande, Ralph A Saporito
Millipedes (Diplopoda) are well known for their toxic or repellent defensive secretions. As part of a larger investigation, we describe the chemical constituents of 14 species of Tasmanian millipedes in seven genera. Six species in the genus Gasterogramma were found to produce acyclic ketones, including the pungent unsaturated ketones 1, 2, and 6, and the novel (rel-3R,5S,7S)-3,5,7-trimethyl-2,8-decanedione (7b), for which the stereoconfiguration was established by stereoselective syntheses of pairs of isomers...
December 15, 2017: Journal of Natural Products
Federica Pollastro, Diego Caprioglio, Patrizia Marotta, Aniello Schiano Moriello, Luciano De Petrocellis, Orazio Taglialatela-Scafati, Giovanni Appendino
Treatment with iodine cleanly converts various p-menthane-type phytocannabinoids and their carboxylated precursors into cannabinol (CBN, 1a). The reaction is superior to previously reported protocols in terms of simplicity and substrate range, which includes not only tricyclic tetrahydrocannabinols such as Δ9-THC (2a) but also bicyclic phytocannabinoids such as cannabidiol (CBD, 3a). Lower homologues from the viridin series (2c and 3c, respectively) afforded cannabivarin (CBV), a non-narcotic compound that, when investigated against a series of ionotropic (thermo-TRPs) biological end-points of phytocannabinoids, retained the submicromolar TRPA1-activating and TRPM8-inhibiting properties of CBN, while also potently activating TRPV2...
December 14, 2017: Journal of Natural Products
Luke P Robertson, Sandra Duffy, Yun Wang, Dongdong Wang, Vicky M Avery, Anthony R Carroll
Three members of a new class of ascorbic acid-adduct indole alkaloids (1-3), a new prenylated indole alkaloid (4), and five known compounds (5-9) were isolated from the leaves of Flindersia pimenteliana. The structures of 1-4 were elucidated on the basis of their (+)-HRESIMS and 2D NMR spectroscopic data. Antiplasmodial activity was also reported for the natural products against chloroquine-sensitive (3D7) and chloroquine-resistant (Dd2) Plasmodium falciparum with IC50 values ranging from 0.19 to 3.6 μM.
December 13, 2017: Journal of Natural Products
Shengjuan Dong, Baocai Li, Weifeng Dai, Dong Wang, Yi Qin, Mi Zhang
Eight new sesquiterpenoids (1-8), two new diterpenoids (9 and 10), and 17 known sesqui- and diterpenoids (11-27) were isolated from the radix of Curcuma aromatica. Among these compounds, 1 is an unprecedented guaiane with unique cyclopropane and furan functionalities, and 9 is the first atisane diterpenoid isolated from a Curcuma species. Their 2D and 3D structures were established using HRESIMS and spectroscopic methods, including ECD and IECD data. The antioxidant activities of compounds 1-27 were evaluated based on their ability to protect PC12 cells against H2O2-induced damage, with 1, 2, 5-8, 11, 12, 14, 16, 18, and 19 exhibiting notable antioxidant effects on oxidative injury induced by H2O2...
December 13, 2017: Journal of Natural Products
Bruno M Bizzarri, Lorenzo Botta, Eliana Capecchi, Ignacio Celestino, Paola Checconi, Anna T Palamara, Lucia Nencioni, Raffaele Saladino
Different catechol and pyrogallol derivatives have been synthesized by oxidation of coumarins with 2-iodoxybenzoic acid (IBX) in DMSO at 25 °C. A high regioselectivity was observed in accordance with the stability order of the incipient carbocation or radical benzylic-like intermediate. The oxidation was also effective in water under heterogeneous conditions by using IBX supported on polystyrene. The new derivatives showed improved antioxidant effects in the DPPH test and inhibitory activity against the influenza A/PR8/H1N1 virus...
December 13, 2017: Journal of Natural Products
Mai T T Nguyen, Tho H Le, Hai X Nguyen, Phu H Dang, Truong N V Do, Manabu Abe, Ryukichi Takagi, Nhan T Nguyen
Phytochemical analysis of an EtOAc extract of the stems of Artocarpus rigida led to the identification of seven new prenylated 4-chromenones, artocarmins G-M (1-7), and nine known compounds (8-17). Their structures were identified based on physical data analysis. In the tyrosinase inhibitory activity test, norartocarpetin (8) displayed the strongest effect, with an IC50 value of 0.023 μM.
December 11, 2017: Journal of Natural Products
Hui-Xia Huo, Zhi-Xiang Zhu, Yue-Lin Song, She-Po Shi, Jing Sun, Hui Sun, Yun-Fang Zhao, Jiao Zheng, Daneel Ferreira, Jordan K Zjawiony, Peng-Fei Tu, Jun Li
Sixteen new 2-(2-phenylethyl)chromone dimers, including four pairs of enantiomers (1a/1b, 3a/3b, 6a/6b, and 8a/8b), along with eight optically pure analogues (2, 4, 5, 7, and 9-12) were isolated from the resinous wood of Aquilaria sinensis. Their structures were determined by extensive spectroscopic analysis (1D and 2D NMR, UV, IR, and HRMS) and experimental and computed ECD data. Compounds 1-10 feature an unusual 3,4-dihydro-2H-pyran ring linkage connecting two 2-(2-phenylethyl)chromone monomeric units, while compounds 11 and 12 possess an unprecedented 6,7-dihydro-5H-1,4-dioxepine moiety in their structures...
December 11, 2017: Journal of Natural Products
Ming Zhao, Brian Guo, Michael M Onakpa, Tiffany Wong, Kyo Wakasa, Chun-Tao Che, Katherine Warpeha
Broadleaf weeds are very costly for crop growers. Additional herbicidal compounds need to be obtained, especially from natural sources. Extracts of Icacina trichantha were evaluated for responses in germinating seeds and seedlings of rice (Oryza sativa) and Arabidopsis (Arabidopsis thaliana). An ethyl acetate fraction of I. trichantha tuber and a diterpenoid constituent, icacinol (1), were found to have impacts on germination and growth of seedlings. The seed germination inhibitory activity on rice was minimal, but significant on Arabidopsis...
December 11, 2017: Journal of Natural Products
Anthony Fatino, Giovanna Baca, Chamitha Weeramange, Ryan J Rafferty
Reniochalistatin E (1) is one of the five related cyclic peptides isolated from the marine sponge Reniochalina stalagmitis. The discovery of these compounds resulted from a screening program directed toward the identification of proline-rich bioactive compounds. Reniochalistatin E is the only member of the family to possess a tryptophan amino acid residue. Given the cytotoxicity observed for 1, efforts were directed toward developing a synthetic route to 1. The first total synthesis of 1 has been accomplished in a 15-step route in an overall 5...
December 8, 2017: Journal of Natural Products
Kine Ø Hansen, Johan Isaksson, Annette Bayer, Jostein A Johansen, Jeanette H Andersen, Espen Hansen
Bryozoans belonging to the Flustridae family have proven to be a rich source of structurally unique secondary metabolites. As part of our continuing search for bioactive secondary metabolites from Arctic marine invertebrates, the organic extract of Securiflustra securifrons was examined. This resulted in the isolation of three new halogenated, hexacyclic indole-imidazole alkaloids, securamines H-J (1-3), together with the previously reported compounds securamines C (4) and E (5). The structures of the new compounds were elucidated by spectroscopic methods including 1D and 2D NMR and analysis of HRMS data...
December 8, 2017: Journal of Natural Products
Xiao Wang, Lin Li, Rongxiu Zhu, Jiaozhen Zhang, Jinchuan Zhou, Hongxiang Lou
Six new pairs of bibenzyl-based meroterpenoid enantiomers, (±)-rasumatranin A-D (1-4) and (±)-radulanin M and N (5 and 6), and six known compounds were isolated from the adnascent Chinese liverwort, Radula sumatrana. Their structures were elucidated based on spectroscopic data and chiral phase HPLC-ECD analyses. The structures of 1 and 7 were also confirmed by single-crystal X-ray diffraction analysis. Cytotoxicity tests of the isolated compounds showed that 6-hydroxy-3-methyl-8-phenylethylbenzo[b]oxepin-5-one (8) showed activity against the human cancer cell lines MCF-7, PC-3, and SMMC-7721, with IC50 values of 3...
December 7, 2017: Journal of Natural Products
Samantha J Mascuch, Paul D Boudreau, Tristan M Carland, N Tessa Pierce, Joshua Olson, Mary E Hensler, Hyukjae Choi, Joseph Campanale, Amro Hamdoun, Victor Nizet, William H Gerwick, Teresa Gaasterland, Lena Gerwick
The cyanobacterial marine natural product honaucin A inhibits mammalian innate inflammation in vitro and in vivo. To decipher its mechanism of action, RNA sequencing was used to evaluate differences in gene expression of cultured macrophages following honaucin A treatment. This analysis led to the hypothesis that honaucin A exerts its anti-inflammatory activity through activation of the cytoprotective nuclear erythroid 2-related factor 2 (Nrf2)-antioxidant response element/electrophile response element (ARE/EpRE) signaling pathway...
December 7, 2017: Journal of Natural Products
María Yolanda Rios, Víctor Navarro, M Ángeles Ramírez-Cisneros, Enrique Salazar-Rios
Six new compounds, aristoloxazine A (1), aristoloxazine B (2), 7-methoxytaliscanine (3), humul-7-en-1,4,11-triol (4), 8-hydroxy-β-logipinene (5), and 1β-hydroxy-4(14)-eudesmene (6), corresponding to two sulfur-containing aristoloxazines (1 and 2), an aristolactam (3), and three sesquiterpenes (4-6) were isolated, along with 26 known compounds, from the roots of Aristolochia orbicularis. The structures of the new compounds were established based on their spectroscopic and spectrometric data and in the case of aristoloxazine A (1) by single-crystal X-ray crystallography...
December 6, 2017: Journal of Natural Products
Justine Ramseyer, Barbara Thuerig, Maria De Mieri, Hans-Jakob Schärer, Thomas Oberhänsli, Mahabir P Gupta, Lucius Tamm, Matthias Hamburger, Olivier Potterat
An in-house library of more than 3000 extracts of plant and fungal origin was screened against some major plant pathogens. As one of the hits, an ethyl acetate extract from inflorescences of Verbesina lanata showed significant inhibitory activity in vitro against grapevine downy mildew (Plasmopara viticola), with a MIC100 value of 35 μg/mL. An emulsifiable concentrate formulation with 50 mg/g of the extract was developed for in vivo evaluation. A suspension of the formulation containing 1 mg/mL of extract lowered leaf surface infection of grapevine seedling by 82% compared to the nontreated control...
December 4, 2017: Journal of Natural Products
Tim Harig, Christian Schlawis, Lisa Ziesche, Marion Pohlner, Bert Engelen, Stefan Schulz
Bacteria can produce a wide variety of volatile compounds. Many of these volatiles carry oxygen, while nitrogen-containing volatiles are less frequently observed. We report here on the identification and synthesis of new nitrogen-containing volatiles from Salinispora pacifica CNS863 and explore the occurrence in another bacterial lineage, exemplified by Roseobacter-group bacteria. Several compound classes not reported before from bacteria were identified, such as dialkyl ureas and oxalamides. Sulfinamides have not been reported before as natural products...
December 1, 2017: Journal of Natural Products
Livia Marques Casanova, Wenqian Gu, Sônia Soares Costa, Per Bendix Jeppesen
Ocimum gratissimum and Ocimum basilicum are plants ethnopharmacologically used to treat diabetes mellitus, a life-threatening disease that affects millions of people worldwide. In order to further understand their antidiabetic potential, which has been previously demonstrated in animal models, we aimed to investigate the acute and chronic effects of major phenolic substances from both plants on insulin secretion and gene expression in pancreatic islets isolated from NMRI mice. Insulin secretion was measured after acute (1 h) and long-term (72 h) incubation of islets with one of four cinnamic acid derivatives (caftaric, caffeic, chicoric, and rosmarinic acids) or a C-glucosylated flavonoid (vicenin-2)...
December 1, 2017: Journal of Natural Products
Menna El Gaafary, Shahira M Ezzat, Abeer M El Sayed, Omar M Sabry, Susanne Hafner, Sophia Lang, Michael Schmiech, Tatiana Syrovets, Thomas Simmet
We investigated the cytotoxic potential of the cardenolide glycoside acovenoside A against non-small-cell lung cancer cells. Lung cancer is the leading cause of cancer-related mortality and the second most common cancer diagnosed. Epidemiological studies revealed a direct correlation between the regular administration of cardiac glycosides and a lower incidence of various cancers. Acovenoside A, isolated from the pericarps of Acokanthera oppositifolia, potently inhibited proliferation and induced cytotoxicity in A549 non-small-cell lung cancer cells with an IC50 of 68 ± 3 nM after 48 h of exposure...
November 30, 2017: Journal of Natural Products
Dewu Zhang, Jiamei Guo, Min Zhang, Xiao Liu, Mingyu Ba, Xiaoyu Tao, Liyan Yu, Ying Guo, Jungui Dai
Four new oxazole-containing diterpenoids, salvianans A-D (1-4), along with three known diterpenoids (5-7), were isolated from Salvia miltiorrhiza cell cultures. The structures of the new compounds were elucidated using spectroscopic methods and single-crystal X-ray diffraction. The evaluation for their anti-HIV-1 activities revealed that 2 and 3 displayed inhibitory activities with IC50 values of 0.03 and 1.2 μM, respectively. The time of addition (TOA) assay and long terminal repeat (LTR) luciferase reporter assay results indicated that compound 2 was an HIV-1 transcription inhibitor and might be a lead compound of antiviral agents acting on HIV-1 transcription...
November 29, 2017: Journal of Natural Products
Yao-Yue Fan, Jin-Biao Xu, Hong-Chun Liu, Li-She Gan, Jian Ding, Jian-Min Yue
Ten new cephalotane-type diterpenoids, cephanolides A-J (1-10), and two known analogues were isolated and characterized from Cephalotaxus sinensis. Compounds 1-3 represent the first examples of A-ring-contracted cephalotane-type dinorditerpenoids, and compound 4 is an A-ring-contracted norditerpenoid. The biosynthetic pathways for compounds 1-4 are postulated with the coexisting cephalotane-type troponoids as the precursors. Compounds 11 and 12 showed significant cytotoxicities against a panel of tumor cell lines (A549, KB, HL-60, and HT-29) with IC50 values ranging from 0...
November 28, 2017: Journal of Natural Products
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