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Journal of Natural Products

Qi-Bin Chen, Jie Gao, Guo-An Zou, Xue-Lei Xin, Haji Akber Aisa
Fifteen new piperidine derivatives, pyracyclumines A-J (1-10), including five pairs of enantiomers, (+)-1/(-)-1 to (+)-5/(-)-5, together with three known compounds, agrocybenine (11), 4,6,6-trimethyl-5,6-dihydro-2(1 H)-pyridone (12), and 3,5,5-trimethyl-1,5-dihydro-2 H-pyrrol-2-one (13), were isolated from the roots of Anacyclus pyrethrum. Pyracyclumines A, B, and H (1, 2, and 8) possess a novel 6/5/6/6 dimeric piperidine skeleton, a unique 6/5/6 dimeric piperidine skeleton, and a 1,4,6-triazaindan skeleton, respectively...
May 18, 2018: Journal of Natural Products
Jian Xu, Hui-Lin Zhu, Jie Zhang, Tao Du, Er-Yan Guo, Wen-Yuan Liu, Jian-Guang Luo, Feng Ye, Feng Feng, Wei Qu
Glutamate-induced excitotoxicity plays a vital role in neurodegenerative diseases. Neuroprotection against excitotoxicity has been considered as an effective experimental approach for preventing and/or treating excitotoxicity-mediated diseases. In the present study, six new sesquiterpenoids (1-6) and 26 known compounds of this type (7-32) were isolated and characterized from the whole plants of Chloranthus anhuiensis. Chlorantolide A (1) is the first example of a 5,6- seco-germacrane-type sesquiterpenoid, while phacadinane E (2) is a rare 4,5- seco-cadinane-type sesquiterpenoid...
May 18, 2018: Journal of Natural Products
Shuangshuang Xie, Ye Wu, Yuben Qiao, Yi Guo, Jianping Wang, Zhengxi Hu, Qing Zhang, Xiaonian Li, Jinfeng Huang, Qun Zhou, Zengwei Luo, Junjun Liu, Hucheng Zhu, Yongbo Xue, Yonghui Zhang
To explore the chemical diversity of metabolites from endophytic fungi, the strain Phomopsis sp. TJ507A, isolated from the medicinal plant Phyllanthus glaucus, was investigated. A 2,3- seco-protoilludane-type sesquiterpenoid (1), eight protoilludane-type sesquiterpenoids (2-9), four illudalane-type sesquiterpenoids (10a/10b, 11, and 12), and a botryane-type sesquiterpenoid (13) in addition to seven known sesquiterpenoids (14-20) were identified from the liquid culture of the fungus. Structures of the isolated compounds, including their absolute configurations, were elucidated based on extensive spectroscopic analyses, a modified Mosher analysis, electronic circular dichroism (ECD) calculations, and [Rh2 (OCOCF3 )4 ]-induced ECD spectra as well as X-ray crystallographic analyses...
May 17, 2018: Journal of Natural Products
Chun Gui, Jie Yuan, Xuhua Mo, Hongbo Huang, Shanwen Zhang, Yu-Cheng Gu, Jianhua Ju
The C7 (C9 or C10)- O-l-rhodosamine-bearing anthracycline antibiotic cytorhodins and their biosynthetic intermediates were recently isolated from Streptomyces sp. SCSIO 1666. Cosmid p17C4 from the Streptomyces lydicus genomic library, which harbors both the biosynthetic genes for l-rhodinose (or 2-deoxy-l-fucose) and its glycosyltransferase (encoded by slgG), was introduced into SCSIO 1666 to yield the recombinant strain Streptomyces sp. SCSIO 1666/17C4. Chemical investigations of this strain's secondary metabolic potential revealed the production of different anthracyclines featuring C7- O-l-rhodinose (or 2-deoxy-l-fucose) instead of the typically observed l-rhodosamine...
May 16, 2018: Journal of Natural Products
Wonhwa Lee, Doohyun Lee, Yuri Lee, Taeho Lee, Kyung-Sik Song, Eun-Ju Yang, Jong-Sup Bae
Only a few isoflavones have been isolated from plants of the genus Abronia. The biological properties of compounds isolated from Abronia species have not been well established, and their antisepsis effects have not been reported yet. In the present study, a new C-methylcoumarinochromone, was isolated from Abronia nana suspension cultures. Its structure was deduced as 9,11-dihydroxy-10-methylcoumarinochromone (boeravinone Y, 1) by spectroscopic data analysis and verified by chemical synthesis. The potential inhibitory effects of 1 against high mobility group box 1 (HMGB1)-mediated septic responses were investigated...
May 15, 2018: Journal of Natural Products
Xiao-Li Qi, Ying-Ying Zhang, Peng Zhao, Le Zhou, Xiao-Bo Wang, Xiao-Xiao Huang, Bin Lin, Shao-Jiang Song
Thirteen new ent-kaurane diterpenoids, stigmaydenes A-M (1-13), together with two known compounds (14, 15), were isolated from the crude extract of corn silk ( Zea mays). The structures of the compounds were confirmed by comprehensive spectroscopic analyses. The absolute configuration of compound 1 was defined by single-crystal X-ray diffraction. The absolute configurations of the compounds were also confirmed by comparison of experimental and calculated specific rotations. The compounds were evaluated for their neuroprotective effects against H2 O2 -induced SH-SY5Y cell injury, and compound 8 was active at 100 μM, as determined by flow cytometry (annexin V-FITC/PI staining) and Hoechst 33258 staining...
May 15, 2018: Journal of Natural Products
Meri Emili F Pinto, Jhenny Z G Najas, Luma G Magalhães, Antonio F Bobey, Jacqueline N Mendonça, Norberto P Lopes, Flávia M Leme, Simone P Teixeira, Marcelo Trovó, Adriano D Andricopulo, Johannes Koehbach, Christian W Gruber, Eduardo Maffud Cilli, Vanderlan S Bolzani
Two new bracelet cyclotides from roots of Pombalia calceolaria with potential anticancer activity have been characterized in this work. The cyclotides Poca A and B (1 and 2) and the previously known CyO4 (3) were de novo sequenced by MALDI-TOF/TOF mass spectrometry (MS). The MS2 spectra were examined and the amino acid sequences were determined. The purified peptides were tested for their cytotoxicity and effects on cell migration of MDA-MB-231, a triple-negative breast cancer cell line. The isolated cyclotides reduced the number of cancer cells by more than 80% at 20 μM, and the concentration-related cytotoxic responses were observed with IC50 values of 1...
May 14, 2018: Journal of Natural Products
Yu-Xun Zhu, Zhao-Xin Zhang, Hui-Min Yan, Di Lu, Huan-Ping Zhang, Li Li, Yun-Bao Liu, Yong Li
Three new leucothane-type (1-3), two new micrathane-type (4, 5), eight new grayanane-type diterpenoids (6-13), and four known compounds were obtained from the ethanol extract of the leaves and twigs of Rhododendron decorum. The structures were determined based on NMR spectra, quantum chemical calculations, and X-ray crystallography. The antinociceptive activities of compounds 1, 3, 4, 6, 8, 10-13, and 15-17 were evaluated via the acetic acid-induced writhing test. Compounds 1, 8, 11-13, and 15 exhibited significant antinociceptive activities...
May 14, 2018: Journal of Natural Products
Joanne Soon-Yee Yeap, Suerialoasan Navanesan, Kae-Shin Sim, Kien-Thai Yong, Subramaniam Gurusamy, Siew-Huah Lim, Yun-Yee Low, Toh-Seok Kam
Examination of the EtOH extract of the Malayan Alstonia penangiana resulted in the isolation of 10 new alkaloids, comprising two ajmaline (1, 2), four macroline oxindole (3-6), and four macroline-akuammiline bisindole alkaloids (7-10). The structures of these alkaloids were determined based on analysis of the spectroscopic data and, in the case of the oxindole 6 and the bisindole alkaloid 7, also confirmed by X-ray diffraction analysis. The bisindole alkaloids 7 and 8 showed pronounced in vitro growth inhibitory activity against an array of human cancer cell lines, including KB, vincristine-resistant KB, PC-3, LNCaP, MCF7, MDA-MB-231, HT-29, HCT 116, and A549 cells with IC50 values in the 0...
May 10, 2018: Journal of Natural Products
Ling Chuang, Chi-Hsiang Wen, Yi-Ru Lee, Yan-Liang Lin, Li-Ren Hsu, Sheng-Yang Wang, Fang-Hua Chu
Terpenoids are a large group of important secondary metabolites that are involved in a variety of physiological mechanisms, and many are used commercially in the cosmetics and pharmaceutical industries. During the past decade, the topic of seasonal variation in terpenoid biosynthesis has garnered increasing attention. Formosan sweet gum ( Liquidambar formosana Hance) is a deciduous tree species. The expression of terpene synthase and accumulation of terpenoids in leaves may vary in different seasons. Here, four sesquiterpene synthases (i...
May 10, 2018: Journal of Natural Products
Rui Li, Jing-Fang Zhang, Yu-Zhuo Wu, Yan-Cheng Li, Gui-Yang Xia, Ling-Yan Wang, Bo-Lin Qiu, Min Ma, Sheng Lin
Fractionation of an aqueous extract of the air-dried roots of a traditional Chinese medicinal plant, Paeonia lactiflora, yielded the new monoterpenoid glycosides 1-10. Their structures were assigned via spectroscopic techniques, and the absolute configurations of 1, 4-6, and 8 were verified via chemical methods, specific rotation, and electronic circular dichroism data. Compounds 1-4 are rare compared to the reported cage-like paeoniflorin derivatives; that is, they comprised two monoterpenoidal moieties. In the in vitro assay, compounds 5, 8, and 9 showed weak inhibitions against lipopolysaccharide-induced nitric oxide production in RAW264...
May 9, 2018: Journal of Natural Products
Tian-Xiao Li, Rui-Huan Liu, Xiao-Bing Wang, Jun Luo, Jian-Guang Luo, Ling-Yi Kong, Ming-Hua Yang
Peyronellones A and B (1 and 2), a pair of rare tetracyclic caged adducts of azaphilone with pyruvic acid, along with four new analogues (3-6), were isolated from solid cultures of the endophytic fungus Peyronellaea glomerata. Their structures were elucidated through spectroscopic analysis, and their absolute configurations were unambiguously determined by a combination of single-crystal X-ray crystallography, Rh2 (OCOCF3 )4 -induced ECD experiments, ECD calculations, and modified Mosher methods. Compound 2 (5 μM) was found to have a significant hypoxia-protective effect that improved the survival rate of hypoxia/reoxygenation-treated human umbilical vein endothelial cells from 35% to 70%, which was equal to the potency of the positive control, verapamil...
May 8, 2018: Journal of Natural Products
Yongle Du, Ana L Valenciano, Michael Goetz, Maria B Cassera, David G I Kingston
An extract of Petradoria pumila from the Natural Products Discovery Institute was found to have moderate antiplasmodial activity, with an IC50 value between 5 and 10 μg/mL. The four new diterpenoids petradoriolides A-D (1-4), the new benzotropolone petradoriolone (5), and the two known lignans 6 and 7 were isolated after bioassay-directed fractionation. The structures and stereochemistries of the new compounds were determined by interpretation of NMR spectroscopy, mass spectrometry, and ECD spectra. Among these compounds, petradoriolide C (3) displayed the most potent antiplasmodial activity, with an IC50 value of 7...
May 8, 2018: Journal of Natural Products
Heikki Eräsalo, Mari Hämäläinen, Tiina Leppänen, Ilari Mäki-Opas, Mirka Laavola, Raisa Haavikko, Jari Yli-Kauhaluoma, Eeva Moilanen
Stilbenoids are a group of polyphenolic compounds found in plants, trees, berries, and nuts. Stilbenoids have been shown to serve an antimicrobial and antifungal function in plants. There is also evidence that as a part of the human diet, stilbenoids play an important role as antioxidants and may have anti-inflammatory effects. The PI3K/Akt pathway is a well-characterized signaling pathway controlling cellular functions involved in growth and cell cycle and in metabolism. There is also increasing evidence to show the involvement of this pathway in the regulation of inflammatory responses...
May 4, 2018: Journal of Natural Products
Hitoshi Kamauchi, Yuki Shiraishi, Akiyo Kojima, Naoki Kawazoe, Kaoru Kinoshita, Kiyotaka Koyama
A chemical investigation of the ascomycetes of Daldinia concentrica was performed using silica gel column chromatography, ODS column chromatography, and preparative HPLC. Two new isoindolinone compounds, daldinans B (1) and C (2), two new phthalide compounds, daldinolides A (3) and B (4), and a new naphthoquinone, daldiquinone (5), were isolated together with two known compounds (6 and 7). The structures of 1, 2, and 5 were established using NMR, MS, and IR methods, and the structures of 3 and 4 were determined by derivatization from known compounds (6 and 7)...
May 1, 2018: Journal of Natural Products
Bianca J Deans, Nathan L Kilah, Gregory J Jordan, Alex C Bissember, Jason A Smith
Extensive phytochemical studies of the paleoendemic Tasmanian Proteaceae species Bellendena montana, Cenarrhenes nitida, and Persoonia gunnii were conducted employing pressurized hot water extraction. As part of these studies, six novel glycosides were isolated, including rare examples of glycoside-containing natural products featuring tiglic acid esters. These polar molecules may represent potential phytochemical markers in ancient Proteaceae.
May 1, 2018: Journal of Natural Products
Rei Suo, Kentaro Takada, Raku Irie, Ryuichi Watanabe, Toshiyuki Suzuki, Yuji Ise, Susumu Ohtsuka, Shigeru Okada, Shigeki Matsunaga
Poecillastrin H (1), a chondropsin-type macrolide with a conjugated pentaene moiety, was isolated from the Characella sp. marine sponge. The planar structure of 1 was elucidated by analysis of spectroscopic data. The absolute configuration of the β-hydroxyaspartic acid residue (β-OHAsp) was determined to be d- threo by Marfey's analysis, and the mode of lactone ring formation through the OHAsp residue was determined by chemical degradation. Poecillastrin H was extremely sensitive toward light and showed potent cytotoxic activity against 3Y1 cells with an IC50 value of 4...
April 27, 2018: Journal of Natural Products
Midori A Arai, Ryuta Akamine, Narumi Hayashi, Takashi Koyano, Thaworn Kowithayakorn, Masami Ishibashi
Notch signaling plays a crucial role in differentiation and cell maintenance, but once aberrantly activated, it contributes to cancer progression. Notch inhibitors were isolated from plant extracts and tested using an originally constructed cell-based assay system. We isolated eight compounds from Nerium indicum that showed inhibition of the Notch signaling pathway. HES1 and HES5 are target genes of the Notch signaling pathway, and oleandrin (1) decreased the protein levels of HES1 and HES5 in assay cells. Oleandrin (1) showed potent cytotoxicity against HPB-ALL cells and decreased HES1 and the Notch intracellular domain in these cells...
April 25, 2018: Journal of Natural Products
Safa M Shams Eldin, Mohamed M Radwan, Amira S Wanas, Abdel-Azim M Habib, Fahima F Kassem, Hala M Hammoda, Shabana I Khan, Michael L Klein, Khaled M Elokely, Mahmoud A ElSohly
The in vitro antidiabetic and antihyperlipidemic activities of an alcoholic extract of Trigonella stellata were evaluated in terms of the activation of PPARα and PPARγ in human hepatoma (HepG2) cells. The extract was investigated phytochemically, aiming at the isolation of the most active compounds to be used as a platform for drug discovery. Three new isoflavans, (3 S,4 R)-4,2',4'-trihydroxy)-7-methoxyisoflavan (1), (3 R,4 S)-4,2',4'-trihydroxy-7-methoxy-4'- O-β-d-glucopyranosylisoflavan (2), and (2 S,3 R,4 R)-4,2',4'-trihydroxy-2,7-dimethoxyisoflavan (3), were isolated and characterized along with the five known compounds p-hydroxybenzoic acid (4), 7,4'-dihydroxyflavone (5), dihydromelilotoside (6), quercetin-3,7- O-α-l-dirhamnoside (7), and soyasaponin I (8)...
April 20, 2018: Journal of Natural Products
Kan'ichiro Ishiuchi, Dai Hirose, Takuma Suzuki, Waka Nakayama, Wen-Ping Jiang, Orawan Monthakantirat, Jin-Bin Wu, Susumu Kitanaka, Toshiaki Makino
12- epi-Lycopodine (1), a Lycopodium alkaloid, along with lycopodine (2) and huperzine A (3), were discovered in the mycelium of Paraboeremia sp. Lsl3KI076, a UV-irradiated strain of Paraboeremia sp. Lsl3, an endophytic fungus from Lycopodium serratum Thunb. var. longipetiolatum Spring. Additionally, a trace of 1 was isolated from Phlegmariurus nummulariifolius (Blume) Ching, and the structure was elucidated on the basis of spectroscopic data. This is the first report proving that a new naturally occurring Lycopodium alkaloid can be obtained from an endophytic fungus...
April 20, 2018: Journal of Natural Products
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