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Journal of Natural Products

Yi-Bing Wu, Ya-Zhen Wang, Zhi-Yu Ni, Xia Qing, Qing-Wen Shi, Françoise Sauriol, Christopher J Vavricka, Yu-Cheng Gu, Hiromasa Kiyota
Two tetranortriterpenoids with new skeletons, xylomexicanins I and J (1 and 2), were isolated during the investigation of chemical constituents from seeds of the Chinese mangrove, Xylocarpus granatum. Xylomexicanin I (1) is an unprecedented limonoid with bridged B- and C-rings. A biosynthesis pathway for 1 from xylomexicanin F is proposed.
August 22, 2017: Journal of Natural Products
Tatsuro Yoneyama, Midori A Arai, Ryuta Akamine, Kazune Koryudzu, Anna Tsuchiya, Samir K Sadhu, Firoj Ahmed, Motoyuki Itoh, Ryuichi Okamoto, Masami Ishibashi
Neurodegenerative diseases such as Alzheimer's disease and Parkinson's disease occur due to loss of the structure and function of neurons. For the potential treatment of neurodegenerative diseases, accelerators of neuronal differentiation of neural stem cells (NSCs) have been focused on and a cell-based assay system for measuring Notch signaling pathway activity was constructed. Using this assay system, eight compounds isolated from Calotropis gigantea were identified as inhibitors of the Notch signaling pathway...
August 17, 2017: Journal of Natural Products
Birgit M Dietz, Shao-Nong Chen, René F Ramos Alvarenga, Huali Dong, Dejan Nikolić, Martin Biendl, Richard B van Breemen, Judy L Bolton, Guido F Pauli
Botanical dietary supplements contain multiple bioactive compounds that target numerous biological pathways. The lack of uniform standardization requirements is one reason that inconsistent clinical effects are reported frequently. The multifaceted biological interactions of active principles can be disentangled by a coupled pharmacological/phytochemical approach using specialized ("knock-out") extracts. This is demonstrated for hops, a botanical for menopausal symptom management. Employing targeted, adsorbent-free countercurrent separation, Humulus lupulus extracts were designed for pre- and postmenopausal women by containing various amounts of the phytoestrogen 8-prenylnaringenin (8-PN) and the chemopreventive constituent xanthohumol (XH)...
August 16, 2017: Journal of Natural Products
Satomi Tanaka, Shinya Shiomi, Hayato Ishikawa
Isoprene units derived from dimethylallyl diphosphate (DMAPP) are an important motif in many natural products including terpenoids, carotenoids, steroids, and natural rubber. Understanding the chemical characteristics of DMAPP is an important topic in natural products chemistry, organic chemistry, and biochemistry. We have developed a direct bioinspired indole prenylation reaction using DMAPP or its equivalents as the electrophile in homogeneous aqueous acidic media in the absence of enzyme to provide prenylated indole products...
August 13, 2017: Journal of Natural Products
Manuel A Aparicio-Cuevas, Isabel Rivero-Cruz, Mariano Sánchez-Castellanos, Daniel Menéndez, Huzefa A Raja, Pedro Joseph-Nathan, María Del Carmen González, Mario Figueroa
Two new dioxomorpholines, 1 and 2, three new derivatives, 3-5, and the known compound PF1233 B (6) were isolated from a marine-facultative Aspergillus sp. MEXU 27854. Their structures were established by 1D and 2D NMR and HRESIMS data analysis. The absolute configuration of 1 and 2 was elucidated by comparison of experimental and DFT-calculated vibrational circular dichroism spectra. Compounds 3, 5, and 6 were noncytotoxic to a panel of human cancer cell lines with different functional status for the tumor-suppressor protein p53, but were inhibitors of P-glycoprotein-reversing multidrug resistance in a doxorubicin-resistant cell line...
August 10, 2017: Journal of Natural Products
Yun-Seo Kil, Seong Min Kim, Unwoo Kang, Hae Young Chung, Eun Kyoung Seo
Ten new glycosides, 6,10-O-di-trans-feruloyl catalpol (1), 6,6'-O-di-trans-feruloyl catalpol (2), 3,4-dihydro-6-O-di-trans-feruloyl catalpol (10), (8R,7'S,8'R)-lariciresinol 9'-O-β-d-(6-O-trans-feruloyl)glucopyranoside (17), and ovatosides A-F (18-22, 24), were isolated from the stem bark of Catalpa ovata along with 19 known compounds. All isolates, except 6 (catalposide) and 9 (6-O-veratroyl catalpol), were found to scavenge peroxynitrite (ONOO(-)) formed by 3-morpholinosydnonimine. In particular, 12 compounds showed potent activity, with IC50 values in the range 0...
August 8, 2017: Journal of Natural Products
Hai X Nguyen, Mai T T Nguyen, Nhan T Nguyen, Suresh Awale
The ethanol extract of propolis from the Vietnamese stingless bee Trigona minor possessed potent preferential cytotoxicity against PANC-1 human pancreatic cancer cells in nutrient-deprived medium, with a PC50 value of 14.0 μg/mL. Chemical investigation of this extract led to the isolation of 15 cycloartane-type triterpenoids, including five new compounds (1-5), and a lanostane-type triterpenoid. The structures of the new compounds were elucidated on the basis of NMR spectroscopic analysis. Among the isolated compounds, 23-hydroxyisomangiferolic acid B (5) and 27-hydroxyisomangiferolic acid (13) exhibited the most potent preferential cytotoxicity against PANC-1 human pancreatic cancer cells under nutrition-deprived conditions, with PC50 values of 4...
August 7, 2017: Journal of Natural Products
Melinda J Waterman, Ari S Nugraha, Rudi Hendra, Graham E Ball, Sharon A Robinson, Paul A Keller
Ceratodon purpureus is a cosmopolitan moss that survives some of the harshest places on Earth: from frozen Antarctica to hot South Australian deserts. In a study on the survival mechanisms of the species, nine compounds were isolated from Australian and Antarctic C. purpureus. This included five biflavonoids, with complete structural elucidation of 1 and 2 reported here for the first time, as well as an additional four known phenolic compounds. Dispersion-corrected DFT calculations suggested a rotational barrier, leading to atropisomerism, resulting in the presence of diastereomers for compound 2...
August 7, 2017: Journal of Natural Products
Fekadu-Roge Gobu, Jian-Jun Chen, Jun Zeng, Wen-Jun Wei, Wei-Feng Wang, Chang-Jun Lin, Kun Gao
Six new (1-3 and 6-8) and seven known diterpenoids were isolated from the whole plant of Ligularia fischeri. Compound 1 is a new 15,16-dinorerythroxylane-type diterpenoid possessing a C18 skeleton, and 2 is the first example of a 6/6/6/6/5/5-fused hexacyclic ent-kaurane diterpenoid with 19,20-olide and 11,16-epoxy moieties. The structures of the new compounds were elucidated by spectroscopic analysis and chemical methods. The absolute configurations of 1 and 7 were determined by single-crystal X-ray diffraction...
August 7, 2017: Journal of Natural Products
C Benjamin Naman, Jehad Almaliti, Lorene Armstrong, Eduardo J Caro-Díaz, Marsha L Pierce, Evgenia Glukhov, Amanda Fenner, Carmenza Spadafora, Hosana M Debonsi, Pieter C Dorrestein, Thomas F Murray, William H Gerwick
A recent untargeted metabolomics investigation into the chemical profile of 10 organic extracts from cf. Symploca spp. revealed several interesting chemical leads for further natural product drug discovery. Subsequent target-directed isolation efforts with one of these, a Panamanian marine cyanobacterium cf. Symploca sp., yielded a phenethylamide metabolite that terminates in a relatively rare gem-dichlorovinylidene moiety, caracolamide A (1), along with a known isotactic polymethoxy-1-alkene (2). Detailed NMR and HRESIMS analyses were used to determine the structures of these molecules, and compound 1 was confirmed by a three-step synthesis...
August 7, 2017: Journal of Natural Products
Olga V Tsepaeva, Andrey V Nemtarev, Timur I Abdullin, Leysan R Grigor'eva, Elena V Kuznetsova, Rezeda A Akhmadishina, Liliya E Ziganshina, Hanh H Cong, Vladimir F Mironov
A series of new triphenylphosphonium (TPP) derivatives of the triterpenoid betulin (1, 3-lup-20(29)-ene-3β,28-diol) have been synthesized and evaluated for cytotoxic effects against human breast cancer (MCF-7), prostate adenocarcinoma (PC-3), vinblastine-resistant human breast cancer (MCF-7/Vinb), and human skin fibroblast (HSF) cells. The TPP moiety was applied as a carrier group through the acyl linker at the 28- or 3- and 28-positions of betulin to promote cellular and mitochondrial accumulation of the resultant compounds...
August 7, 2017: Journal of Natural Products
Nicholas Lorig-Roach, Patrick C Still, David Coppage, Jennifer E Compton, Mitchell S Crews, Gabriel Navarro, Karen Tenney, Phillip Crews
The biosynthetic potential of marine-sediment-derived Gram-negative bacteria is poorly understood. Sampling of California near-shore marine environments afforded isolation of numerous Gram-negative bacteria in the Proteobacteria and Bacteriodetes phyla, which were grown in the laboratory to provide extracts whose metabolites were identified by comparative analyses of LC-mass spectrometry and MS(n) data. Overall, we developed an assemblage of seven bacterial strains grown in five different media types designed to coax out unique secondary metabolite production as a function of varying culture conditions...
August 4, 2017: Journal of Natural Products
Elda M Melchor-Martínez, David A Silva-Mares, Ernesto Torres-López, Noemí Waksman-Minsky, Guido F Pauli, Shao-Nong Chen, Matthias Niemitz, Mariano Sánchez-Castellanos, Alfredo Toscano, Gabriel Cuevas, Verónica M Rivas-Galindo
The dichloromethane extract of the roots of Jatropha dioica afforded riolozatrione (1) and a C-6 epimer of riolozatrione, 6-epi-riolozatrione (2), as a new structure and only the second reported riolozane diterpenoid. The two known diterpenoids jatrophatrione (3) and citlalitrione (4) were also isolated and characterized. Both epimers 1 and 2 are genuine plant constituents, with 2 likely being the biosynthesis precursor of 1 due to the tendency for the quantitative transformation of 2 into 1 under base catalysis...
August 3, 2017: Journal of Natural Products
Takayuki Tonoi, Yutaka Yoshinaga, Moe Fujishiro, Keisuke Mameda, Takashi Kato, Kentaro Shibamoto, Isamu Shiina
The originally proposed structure of astakolactin was revised, and an asymmetric total synthesis of the newly proposed structure was achieved. The key transformations in the synthesis were a Johnson-Claisen rearrangement, an asymmetric Mukaiyama aldol reaction, and a Mitsunobu-type cyclodehydration. The spectroscopic data and specific rotation of the compound obtained matched well with those reported for naturally occurring astakolactin.
August 2, 2017: Journal of Natural Products
Fredrik Brustad Mellbye, Per Bendix Jeppesen, Pedram Shokouh, Christoffer Laustsen, Kjeld Hermansen, Søren Gregersen
Daily coffee consumption is inversely associated with risk of type-2 diabetes (T2D). Cafestol, a bioactive substance in coffee, increases glucose-stimulated insulin secretion in vitro and increases glucose uptake in human skeletal muscle cells. We hypothesized that cafestol can postpone development of T2D in KKAy mice. Forty-seven male KKAy mice were randomized to consume chow supplemented daily with either 1.1 (high), 0.4 (low), or 0 (control) mg of cafestol for 10 weeks. We collected blood samples for fasting glucose, glucagon, and insulin as well as liver, muscle, and fat tissues for gene expression analysis...
August 1, 2017: Journal of Natural Products
Ji-Qin Hou, Cui Guo, Jian-Juan Zhao, Yang-Yang Dong, Xiao-Long Hu, Qi-Wei He, Bao-Bao Zhang, Ming Yan, Hao Wang
Frutescones H-R (1-11), new sesqui- or monoterpene-based meroterpenoids, were isolated from the aerial parts of Baeckea frutescens. Their structures and absolute configurations were established by means of spectroscopic analyses (HRESIMS, 1D and 2D NMR, and ECD), as well as single-crystal X-ray crystallography of 1, (-)-7, and 9. The anti-inflammatory activities of all isolates were evaluated by measuring their inhibitory effects on NO production in LPS-stimulated RAW 264.7 macrophages, and the structure-activity relationships of 1-11 are also discussed...
July 28, 2017: Journal of Natural Products
Danilo Del Prete, Orazio Taglialatela-Scafati, Alberto Minassi, Carmina Sirignano, Cristina Cruz, Maria L Bellido, Eduardo Muñoz, Giovanni Appendino
Bardoxolone methyl (1) is the quintessential member of triterpenoid cyanoacrylates, an emerging class of bioactive compounds capable of transient covalent binding to thiols. The mechanistic basis for this unusual "pulsed reactivity" profile and the mode of its biological translation are unknown. To provide clues on these issues, a series of Δ(1)-dehydrooleanolates bearing an electron-withdrawing group at C-2 (7a-m) were prepared from oleanolic acid (3a) and comparatively investigated in terms of reactivity with thiols and bioactivity against a series of electrophile-sensitive transcription factors (Nrf2, NF-κB, STAT3)...
July 28, 2017: Journal of Natural Products
Liangxiong Xu, Ping Wu, Jinghua Xue, Istvan Molnar, Xiaoyi Wei
Eight new β-resorcylic acid lactones (RALs), including the hypothemycin-type compounds paecilomycins N-P (1-3) and the radicicol-type metabolites dechloropochonin I (4), monocillins VI (5) and VII (6), 4'-hydroxymonocillin IV (7), and 4'-methoxymonocillin IV (8), along with nine known RALs (9-17), were isolated from the cultures of Paecilomyces sp. SC0924. Compounds 1 and 2 feature a novel 6/11/5 ring system, and 3 is the first 5'-keto RAL. The structures of 1-8 were elucidated on the basis of extensive spectroscopic analysis, X-ray diffraction analysis, and theoretical calculations of ECD spectra...
July 27, 2017: Journal of Natural Products
Jie Ren, Shuang-Shuang Ding, Ao Zhu, Fei Cao, Hua-Jie Zhu
Six new azaphilone derivatives, talaraculones A-F (1-6), together with five known analogues (7-11), were obtained from the saline soil-derived fungus Talaromyces aculeatus. The absolute configurations of 1 and 6 were assigned by quantum chemical calculations of the electronic circular dichroism (ECD) spectra. Compounds 1 and 5 represent the first reported azaphilone derivatives with a C4 aliphatic side chain and a methylal group at C-3, respectively. Talaraculones A and B (1 and 2) exhibited stronger inhibitory activity against α-glucosidase than the positive control acarbose (IC50 = 101...
July 27, 2017: Journal of Natural Products
Ji Sun Hwang, Geum Jin Kim, Hyun Gyu Choi, Min Cheol Kim, Dongyup Hahn, Joo-Won Nam, Sang-Jip Nam, Hak Choel Kwon, Jungwook Chin, Sung Jin Cho, Hayoung Hwang, Hyukjae Choi
Angiogenesis is the process of new blood vessel formation. Excessive angiogenesis is a critical factor in the progression of cancer, macular degeneration, and other chronic inflammatory diseases. When investigating the effects of crude extracts of cultured marine microorganisms, an extract of the cultured Streptomyces sp. YP127 strain was found to inhibit human umbilical vein endothelial cell (HUVEC) tube formation. Bioassay-guided fractionation and spectroscopic data analyses led to the identification of napyradiomycin A1 (1) as an antiangiogenic component of the extract...
July 27, 2017: Journal of Natural Products
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