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Huan Jiang, Gui-Jie Zhang, Hai-Bing Liao, Dong Liang
Two new cadinane sesquiterpene glucosides (1, 2), two new phenylpropanoid glycosides (3, 4), and two new diterpenoid glucosides (5, 6), as well as 6 known compounds were isolated from the stems of Tinospora sinensis. The structures of these compounds were elucidated by extensive spectroscopic analysis and chemical methods. The absolute configuration of compound 1 was determined by timedependent density functional theory (TDDFT) electronic circular dichroism (ECD) calculations and in situ dimolybdenum CD method...
October 16, 2018: Fitoterapia
Jianbei Huang, Henrik Hartmann, Heidi Hellén, Armin Wisthaler, Erica Perreca, Alexander Weinhold, Alexander Rücker, Nicole M van Dam, Jonathan Gershenzon, Susan E Trumbore, Thomas Behrendt
Volatile organic compounds (VOC) play important roles in atmospheric chemistry, plant ecology and physiology, and biogenic VOC (BVOC) emitted by plants is the largest VOC source. Our knowledge about how environmental drivers (e.g. carbon, light and temperature) may regulate BVOC emissions is limited because they are often not controlled. We combined a greenhouse facility to manipulate atmospheric CO2 ([CO2 ]) with proton-transfer-reaction mass spectrometry (PTR-MS) and cavity ring-down spectroscopy to investigate the regulation of BVOC in Norway spruce...
October 18, 2018: Environmental Science & Technology
Rong-Wei Kou, Shuang-Tian Du, Yi-Xiao Li, Xi-Tao Yan, Qiang Zhang, Chen-Yu Cao, Xia Yin, Jin-Ming Gao
Five terpenoids, including two new cyathane diterpenoids neocyathin S (1) and neocyathin T (2), together with three drimane sesquiterpenoids, one known 3β,6β-dihydroxycinnamolide (3), two new ones 3β,6α-dihydroxycinnamolide (4) and 2-keto-3β,6β-dihydroxycinnamolide (5), were isolated from the cultures of the basidiomycete Cyathus africanus. Their structures were established based on extensive spectroscopic methods including 2D NMR (HSQC, 1 H‒1 H-COSY, HMBC, ROESY) and HRESIMS experiments. The absolute configurations of two pairs of epimers, 1 and 2 as well as 3 and 4, were determined by ECD quantum chemical calculation...
October 16, 2018: Journal of Antibiotics
Taek-In Oh, Hye-Jeong Jung, Yoon-Mi Lee, Sujin Lee, Geon-Hee Kim, Sang-Yeon Kan, Hyeji Kang, Taerim Oh, Hyun Myung Ko, Keun-Chang Kwak, Ji-Hong Lim
Zerumbone (ZER), an active constituent of the Zingiberaceae family, has been shown to exhibit several biological activities, such as anti-inflammatory, anti-allergic, anti-microbial, and anti-cancer; however, it has not been studied for anti-melanogenic properties. In the present study, we demonstrate that ZER and Zingiber officinale (ZO) extract significantly attenuate melanin accumulation in α-melanocyte-stimulating hormone (α-MSH)-stimulated mouse melanogenic B16F10 cells. Further, to elucidate the molecular mechanism by which ZER suppresses melanin accumulation, we analyzed the expression of melanogenesis-associated transcription factor, microphthalmia-associated transcription factor (MITF), and its target genes, such as tyrosinase , tyrosinase-related protein 1 ( TYRP1 ), and tyrosinase-related protein 2 ( TYRP2 ), in B16F10 cells that are stimulated by α-MSH...
October 13, 2018: International Journal of Molecular Sciences
Hong Lu, Jie Chen, Yongming Luo, Huanjun Xu, Ling Xiong, Jianjiang Fu
Curcolonol (CCL) is a furan type sesquiterpene isolated from several medical herbs. Based on previous results of anti-migratory activity screening, in this study, we investigated the effects of CCL on cancer cell motility. By in vitro migration assay, we found that CCL significantly inhibited the vertical and horizontal migration of breast cancer cells induced by transforming growth factor (TGF)-β1. In addition, CCL also exerted inhibitory effects on F-actin polymerization in breast cancer cells when the cells were dyed with phalloidin...
October 10, 2018: International Journal of Oncology
Jorge De La Chapa, Prajjal Kanti Singha, Mckay Sallaway, Kristen Self, Ranna Nasreldin, Ramesh Dasari, Matthew Hart, Alexander Kornienko, Jeremy Just, Jason A Smith, Alex C Bissember, Cara B Gonzales
Polygodial, a drimane sesquiterpenoid dialdehyde isolated as a pungent component of the water pepper Persicaria hydropiper, exhibits antifeedant, antimicrobial, anti-inflammatory and anticancer effects. Polygodial also activates transient receptor potential vanilloid subtype 1 (TRPV1) channels. Previously, we described the synthesis of a C12-Wittig derivative of polygodial, termed P3, with significant antiproliferative effects against multiple cancer types including oral squamous cell carcinoma (OSCC). In the present study, a more potent derivative, P27, with superior anti-proliferative effects in vitro and antitumor effects in Cal-27 derived xenografts is described...
October 5, 2018: International Journal of Oncology
Victor Fattori, Ana C Zarpelon, Larissa Staurengo-Ferrari, Sergio M Borghi, Tiago H Zaninelli, Fernando B Da Costa, Jose C Alves-Filho, Thiago M Cunha, Fernando Q Cunha, Rubia Casagrande, Nilton S Arakawa, Waldiceu A Verri
Background: Gout is the most common inflammatory arthritis worldwide. It is a painful inflammatory disease induced by the deposition of monosodium urate (MSU) crystals in the joints and peri-articular tissues. Sesquiterpene lactones (SLs) are secondary metabolite biosynthesized mainly by species from the family Asteraceae. It has been demonstrated that SLs present anti-inflammatory, analgesic, antitumoral, antiparasitic, and antimicrobial activities. In this study, we aimed at evaluating the efficacy of the SL budlein A in a model of acute gout arthritis in mice...
2018: Frontiers in Pharmacology
Michael Afolayan, Radhakrishnan Srivedavyasasri, Olayinka T Asekun, Oluwole B Familoni, Abayomi Orishadipe, Fazila Zulfiqar, Mohamed A Ibrahim, Samir A Ross
Piliostigma thonningii (Schumach.) Milne-Redhead. (Leguminosae) is used for various medicinal purposes in African countries. Phytochemical investigation of P. thonningii yielded two compounds newly isolated from natural sources, 2 β -methoxyclovan-9 α -ol ( 1 ), and methyl- ent -3 β -hydroxylabd-8(17)-en-15-oate ( 2 ), along with 14 known compounds ( 3 - 16 ). Compounds 1 and 4 (alepterolic acid) showed potential selectivity towards Trypanosoma brucei brucei with IC50 7.89 and 3.42 μM, respectively. Compound 2 showed activity towards T...
October 2018: Medicinal Chemistry Research
Joanna Drogosz, Anna Janecka
Sesquiterpene lactones, secondary metabolites of plants, present in a large number of species mostly from the Asteracea family, were used in the traditional medicine of many countries for the treatment of various pathological conditions. They exert a broad range of activities, including anti-inflammatory, anti-bacterial and anti-cancer properties. The best known sesquiterpene lactones which are already used as drugs or are in clinical trials are artemisinin, thapsigargin and parthenolide. Yet another sesquiterpene lactone, helenalin, an active component of Arnica montana, known for its strong anti-inflammatory activity, has been used for centuries in folk medicine to treat minor injuries...
October 12, 2018: Current Drug Targets
Tareq Abu-Izneid, Abdur Rauf, Muhammad Saleem, Nashwa Mansour, Mohamed I S Abdelhady, Munjed M Ibrahim, Seema Patel
Urease inhibition potential of compound (1), guaiane-type sesquiterpene (2), confertin (3) and scopoletin (4) was carried out with high throughput mechanism-based assay. These compounds were isolated from Hypochaeris radicata L., an Asteraceae family member. The pure compounds were screened for their urease and carbonic anhydrase inhibitory activities. The ethyl acetate fractions were subjected to column chromatography, which resulted in the isolation and purification of four compounds (1-4). On evaluation, compounds (1-4) exhibited selective activity against urease enzyme with an IC50 value of 180...
October 15, 2018: Natural Product Research
Ahmad Nazif Aziz, Nor Hadiani Ismail, Siti Nadiah Abdul Halim, Chung Yeng Looi, El Hassane Anouar, Moses K Langat, Dulcie Mulholland, Khalijah Awang
A phytochemical investigation of the stem barks of the Malaysian Croton oblongus Burm.f. (Syn. Croton laevifolius Blume) (Euphorbiaceae) yielded seven previously undescribed ent-neo-clerodane diterpenoids, laevifins A - G and the known crovatin (3). Structures were established by a combination of spectroscopic methods including HRESIMS, NMR spectroscopy and X-ray crystallography. The absolute configuration of crovatin and laevifins A-G was established by comparison of experimental ECD and theoretical TDDFT ECD calculated spectra...
October 10, 2018: Phytochemistry
Zhaodi Wu, Dongyan Li, Fanrong Zeng, Qingyi Tong, Yinyu Zheng, Junjun Liu, Qun Zhou, Xiao-Nian Li, Chunmei Chen, Yongji Lai, Hucheng Zhu, Yonghui Zhang
Brasilanones A-F and asperterreusines A-C, undescribed brasilane sesquiterpenoids and dihydrobenzofuran derivatives, were isolated from the marine-derived fungus Aspergillus terreus [CFCC 81836]. Their structures with absolute configurations were elucidated on the basis of spectroscopic data, X-ray crystallographic analyses, and electronic circular dichroism (ECD) calculations. Brasilanones A-F are unusual brasilane sesquiterpenoids with an α,β-unsaturated ketone unit, interestingly, brasilanones B-D are stereo isomers...
October 8, 2018: Phytochemistry
Simon J Kim, Alan J Lough, Robert A Batey
A domino silver(I) promoted electrocyclic 2-disrotatory electrocyclic ring-opening / intramolecular nucleophilic trapping of [n.1.0]-dibromocyclopropanes by tethered carboxylic acids results in cyclization to butyrolactones fused to six- and seven-membered carbocycles. In the case of bicyclic [4.3.0] lactones the cis-fused stereoisomer was formed, whereas for the bicyclic [5.3.0] lactones the trans-fused stereoisomer was formed. Optimal conditions for the reaction used silver(I) trifluoroacetate (2.0 eq...
October 10, 2018: Journal of Organic Chemistry
Changchun Yuan, Shangyong Zhong, Xingyi Li, Yanhong Wang, Miao-Miao Xun, Yunli Bai, Kongkai Zhu
Total synthesis and absolute configuration confirmation of γ-elemene-type sesquiterpenes, which possess vast potential for biological activities, was investigated based on a convergent synthetic strategy. A key intermediate with all functional groups of this family of natural products was accessed by an intermolecular aldol reaction and then an acetylation of a known ketone (12) derived from commercially available verbenone. The versatile intermediate can be easily transformed into structurally different γ-elemene-type sesquiterpenes based on control of base-promoted cyclization manipulation in different solvents...
October 10, 2018: Organic & Biomolecular Chemistry
Gauri Lamture, Peter A Crooks, Michael J Borrelli
Preclinical Research & Development Pancreatic cancer is the third leading cause of death in the US with a poor 5-year survival rate of 8.5%. A novel anti-cancer drug, dimethylamino parthenolide (DMAPT), is the water-soluble analog of the natural sesquiterpene lactone, parthenolide. The putative modes of action of DMAPT are inhibition of the Nuclear chain factor kappa-light-chain enhancer of activated B cells (NFκB) pathway and depletion of glutathione levels; the latter causing cancer cells to be more susceptible to oxidative stress-induced cell death...
September 2018: Drug Development Research
Leticia Alves Gomes Albertti, Thierry L Delatte, Katyuce Souza de Farias, Amanda Galdi Boaretto, Francel Verstappen, Adele van Houwelingen, Katarina Cankar, Carlos Alexandre Carollo, Harro J Bouwmeester, Jules Beekwilder
Candeia ( Eremanthus erythropappus (DC) McLeisch, Asteraceae) is a Brazilian tree, mainly occurring in the cerrado areas. From ethnobotanical information its essential oil is known to have wound healing and nociceptive properties. These properties are ascribed to result from a sesquiterpene alcohol, (-)-α-bisabolol, which is present at high concentrations in this oil. Bisabolol is highly valued by the cosmetic industry because of its antibacterial, anti-inflammatory, skin-smoothing and wound healing properties...
2018: Frontiers in Plant Science
An-Dong Wang, Yun-Qiang Zhang, Mei-Chen Li, Xia Wang, Bin Lin, Jian-Yu Liu, Yong-Nan Xu
Zeasesquiterpene A-E (1-5), five new sesquiterpenes with two cyclohexanes, were isolated from the roots of Zea mays. Their structures were elucidated on the basis of 1D and 2D NMR spectral data and ECD analysis. A plausible biosynthetic pathway for the compounds (1-6) were hypothesized. All isolated compounds were screened for cytotoxicities against five human cancer cell lines (A549, MDA-MB-231, SK-Hep-1, SNU638 and HCT116) in vitro by MTT assay. Compound 4 showed potential cytotoxic activities against A549 (14...
October 2, 2018: Fitoterapia
Juan Xiong, Li-Jun Wang, Jianchang Qian, Pei-Pei Wang, Xue-Jiao Wang, Guang-Lei Ma, Huaqiang Zeng, Jia Li, Jin-Feng Hu
A preliminary phytochemical investigation on the MeOH extract of the leaves and twigs of the endangered ornamental plant Michelia shiluensis led to the isolation of 16 sesquiterpenoids. The isolated compounds comprised germacrane- (1-4, 13, 14), guaiane- (5-9, 15), amorphane- (10), and eudesmane-type (11, 12, 16) sesquiterpenoids. The new structures (1-12) were elucidated by spectroscopic and computational methods, and their absolute configurations (except for 9) were assigned by single-crystal X-ray diffraction crystallographic data and/or electronic circular dichroism spectra...
October 5, 2018: Journal of Natural Products
Omar Farid, Naoufel Ali Zeggwagh, Mohamed Eddouks
OBJECTIVE: The aim of this work was to evaluate the antihyperglycemic activity of aerial parts aqueous extract (A.P.A.E) of Mentha pulegium (M. pulegium) on blood glucose levels in normal and streptozotocin(STZ)-induced diabetic rat. Also the glucose tolerance was evaluated in normal rats. Moreover, the histological sections and morphometric analysis at the liver and pancreas have been carried out in this investigation both in normal and STZ-diabetic rats. METHODS: The effect of A...
October 4, 2018: Endocrine, Metabolic & Immune Disorders Drug Targets
Juxiang Liu, Lianli Zhang, Dan Liu, Baocai Li, Mi Zhang
Aim & objectives: Curcumins, also known as diarylheptanoids, are regarded as characteristic constituents in Curcuma, which have obviously neuroprotective activities against oxidative stress. As one of Traditional Chinese Medicines from Curcuma, the radix of Curcuma aromatic is also rich in curcumins, but its neuroprotective activity and underlying mechanism remains unknown. The aim of current study is to evaluate the neuroprotective effects of different extracts from the radix of C. aromatic (ECAs) on hydrogen peroxide (H2O2) -damaged PC12 cells...
October 5, 2018: Combinatorial Chemistry & High Throughput Screening
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