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Hamidreza Nikpour, Mehdi Mousavi, Hamideh Asadollahzadeh
INTRODUCTION: Teucrium polium is a herbal plant which has curative potential and pharmacological characteristics. Therefore, establishment of accurate analytical methods for characterising its active components is of prime importance. OBJECTIVE: Because of the complex nature of essential oil samples, some results of direct gas chromatography-mass spectrometry (GC-MS) analysis maybe unreliable. Therefore, GC-MS is coupled with chemometric methods to resolve experimental information taken from chromatographic peaks, and assign compounds to them more correctly...
June 7, 2018: Phytochemical Analysis: PCA
Huma Ali, Mubarak Ali Khan, Nazif Ullah, Raham Sher Khan
Light is an important physical factor necessary for the growth, morphogenesis and production of bioactive compounds in plants. In this study, effects of different photoperiod regimes and hormonal elicitors were investigated on the accumulation of biomass, antioxidant potential and biosynthesis of secondary volatiles in the cell cultures of Ajuga bracteosa. Maximum accumulation of biomass (13.2 g/L) was recorded in cell cultures established at 1.0 mg/L benzylaminopurine (BA) in exposure to continuous dark...
April 27, 2018: Journal of Photochemistry and Photobiology. B, Biology
Tímea Gonda, Péter Bérdi, István Zupkó, Ferenc Fülöp, Zsolt Szakonyi
Stereoselective synthesis of monoterpene-based 1,2,4- and 1,3,4-oxadiazole derivatives was accomplished starting from α,β-unsaturated carboxylic acids, obtained by the oxidation of (-)-2-carene-3-aldehyde and commercially available (-)-myrtenal. 1,2,4-Oxadiazoles were prepared in two steps via the corresponding O -acylamidoxime intermediates, which then underwent cyclisation induced by tetrabutylammonium fluoride (TBAF) under mild reaction conditions. Stereoselective dihydroxylation in highly stereospecific reactions with the OsO₄/NMO ( N -methylmorpholine N -oxide) system produced α,β-dihydroxy 1,2,4-oxadiazoles...
December 28, 2017: International Journal of Molecular Sciences
Konstantin Yu Ponomarev, Evgeniy V Suslov, Alexandra L Zakharenko, Olga D Zakharova, Artem D Rogachev, Dina V Korchagina, Ayesha Zafar, Jóhannes Reynisson, Andrey A Nefedov, Konstantin P Volcho, Nariman F Salakhutdinov, Olga I Lavrik
The ability of a number of nitrogen-containing compounds that simultaneously carry the adamantane and monoterpene moieties to inhibit Tdp1, an important enzyme of the DNA repair system, is studied. Inhibition of this enzyme has the potential to overcome chemotherapeutic resistance of some tumor types. Compound (+)-3c synthesized from 1-aminoadamantane and (+)-myrtenal, and compound 4a produced from 2-aminoadamantane and citronellal were found to be most potent as they inhibited Tdp1 with IC50 values of 6 and 3...
February 2018: Bioorganic Chemistry
Elias M Neeman, Juan Ramón Avilés Moreno, Thérèse R Huet
The gas phase structure of the bicyclic atmospheric aerosol precursor α-pinene was investigated employing a combination of quantum chemical calculation and Fourier transform microwave spectroscopy coupled to a supersonic jet expansion. The very weak rotational spectra of the parent species and all singly substituted13 C in natural abundance have been identified, from 2 to 20 GHz, and fitted to Watson's Hamiltonian model. The rotational constants were used together with geometrical parameters from density functional theory and ab initio calculations to determine the rs , r0 , and rm (1) structures of the skeleton, without any structural assumption in the fit concerning the heavy atoms...
December 7, 2017: Journal of Chemical Physics
Konstantin Ponomarev, Ekaterina Morozova, Alla Pavlova, Evgeniy Suslov, Dina Korchagina, Andrej Nefedov, Tat'yana Tolstikova, Konstantin Volcho, Nariman Salakhutdinov
BACKGROUND: It was found earlier that compounds combining diazaadamantane and monoterpene moieties possessed promising analgesic activity along with low acute toxicity and the lack of ulcerogenic activity. OBJECTIVE: In this paper, new structural analogues of the most active compounds were synthesized and evaluated for their analgesic activity. METHODS: Their structures were confirmed by various analytical methods, such as 1H and 13C NMR, HRMS...
2017: Medicinal Chemistry
Adrian Calborean, Florin Graur, Vasile Bintintan
Correlations between DFT and experimental measurements on Zn2+ and Ni2+ chiral meso-(α,β-unsaturated)- porphyrins were performed using Kohn-Sham methodology. The exchange-correlation Becke88-Perdew86 functional was used in conjunction with double-zeta Slater basis sets. An accurate description of the electronic processes depending on the metal ion (Zn, Ni) or ligand (perilaldehyde and myrtenal) was made, confirming experimental results in terms of structural and electronic modifications. Moreover, this theoretical study provides a stronger knowledge and interpretation of the dynamical conformational features of the free base, Zn and Ni structures...
June 2017: Journal of Molecular Modeling
D Andrys, M Adaszyńska-Skwirzyńska, D Kulpa
The aim of the present study was to determine the effect of jasmonic acid added to the culture medium on composition of Lavandula angustifolia essential oils. The chemical composition was determined by gas chromatography coupled to mass detector (GC/MS). The experiment was conducted with the use of MS medium supplemented with increasing concentration of JA (0.2, 0.5, 1, 1.5 mg∙dm-3 ). It was found that the analysed essential oils varied in terms of chemical composition depending on the content of JA in the medium...
April 2018: Natural Product Research
Gui-Shan Lin, Wen-Gui Duan, Lin-Xiao Yang, Min Huang, Fu-Hou Lei
A series of novel myrtenal derivatives bearing 1,2,4-triazole moiety were designed and synthesized by multi-step reactions in an attempt to develop potent antifungal agents. Their structures were confirmed by using UV-vis, FTIR, NMR, and ESI-MS analysis. Antifungal activity of the target compounds was preliminarily evaluated by the in vitro method against Fusarium oxysporum f. sp. cucumerinum, Physalospora piricola, Alternaria solani, Cercospora arachidicola, and Gibberella zeae at 50 µg/mL. Compounds 6c (R = i-Pr), 6l (R = o-NO₂ Bn), and 6a (R = Et) exhibited excellent antifungal activity against P...
January 24, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
G Duporté, P-M Flaud, E Geneste, S Augagneur, E Pangui, H Lamkaddam, A Gratien, J-F Doussin, H Budzinski, E Villenave, E Perraudin
In the present study, quasi-static reactor and atmospheric simulation chamber experiments were performed to investigate the formation of α-pinene-derived organosulfates. Organosulfates (R-OSO3 H) were examined for the reactions between acidified ammonium sulfate particles exposed to an individual gaseous volatile organic compound, such as α-pinene and oxidized products (α-pinene oxide, isopinocampheol, pinanediol and myrtenal). Molecular structures were elucidated by liquid chromatography interfaced to high-resolution quadrupole time-of-flight mass spectrometry equipped with electrospray ionization (LC/ESI-HR-QTOFMS)...
October 13, 2016: Journal of Physical Chemistry. A
Ayyasamy Rathinam, Leelavinothan Pari
Insulin signaling pathway is an important role in glucose utilization in tissues. Our Previous study has established that myrtenal has antihyperglycemic effect against diabetic rats. The aim of this study was to explore the molecular mechanism of myrtenal in Streptozotocin-induced diabetic rats. Experimental diabetes was induced by single intraperitoneal injection of Streptozotocin (STZ) (40 mg/kg bw) in Wistar albino rats. Diabetic rats were administered myrtenal (80 mg/kg bw) for a period of 28 days. Diabetic rats showed an increased the levels of plasma glucose, decreased the levels of plasma insulin, down-regulation of insulin receptor substrate 2 (IRS2), Akt and glucose transporter 2 (GLUT2) in liver and insulin receptor substrate 2 (IRS2), Akt and glucose transporter 4 (GLUT4) protein expression in skeletal muscle...
August 25, 2016: Chemico-biological Interactions
Julia M Clay, Dusan Hesek, Allen G Oliver, Mijoon Lee, Jed F Fisher
The buffered permanganate oxidation of (-)-myternal, a member of the pinene family, provides the α-hydroxyketone (-)-(1R,3S,5R)-3-hydroxy-6,6-dimethylbicyclo[3.1.1]heptan-2-one in preparative yield (65% on a multigram scale). This α-hydroxyketone is oxidized, in a second reaction, to the α,β-diketone (1R,5R)-6,6-dimethylbicyclo[3.1.1]heptane-2,3-dione ("PinDione"). As both oxidations are fast, simple, safe, inexpensive, good-yielding, and multigram scalable, these transformations are a preparative expansion of the pinane family...
July 1, 2016: Journal of Organic Chemistry
Rathinam Ayyasamy, Pari Leelavinothan
CONTEXT: Myrtenal is monoterpene a constituent of essential oils found mainly in herbs such as mint, pepper, cumin, etc. It exerts admirable pharmacological activities against many diseases including diabetes. Hyperlipidaemia is a secondary complication of diabetes and also a major risk factor for cardiovascular diseases. OBJECTIVE: The present study investigated the possible antihyperlipidaemic efficacy of myrtenal on plasma glucose, pancreatic insulin, plasma and tissue lipid levels in streptozotocin (STZ) induced diabetic rats...
November 2016: Pharmaceutical Biology
Noura S Dosoky, Debra M Moriarity, William N Setzer
Conradina canescens (Lamiaceae) is an endemic evergreen shrub native to Florida, Mississippi and Alabama, with no phytochemical or biological studies registered in the literature. Thus, a phytochemical study and a toxicity analysis of the chloroform extract obtained from the leaves of C. canescens were performed for the first time. In our preliminary screening, the crude extract and its fractions were subjected to cytotoxicity, antimicrobial and antileishmanial bioassays. The crude extract showed substantial cytotoxic, antimicrobial and antileishmanial activities...
January 2016: Natural Product Communications
Lukas Schmidt, Thomas Göen
We studied the human in vivo metabolism and the elimination kinetics of α-pinene (αPN), a natural monoterpene which commonly occurs in the environment. Four volunteers were exposed to a single oral dose of 10 mg αPN. Each subject provided one pre-exposure and subsequently all post-exposure urine samples up to 24 h after administration. Additionally, blood samples were drawn hourly from two volunteers for 5 h. The analysis of the parent compound in blood was performed by a headspace GC-MS procedure, whereas the proposed αPN metabolites myrtenol (MYR) and cis- and trans-verbenol (cVER; tVER) were quantified in blood and urine using GC-PCI-MS/MS...
February 2017: Archives of Toxicology
Booupathy Lokeshkumar, Venkatachalam Sathishkumar, Natarajan Nandakumar, Thamaraiselvan Rengarajan, Arumugam Madankumar, Maruthaiveeran Periyasamy Balasubramanian
Colon cancer is considered as the precarious forms of cancer in many developed countries, with few to no symptoms; the tumor is often diagnosed in the later stages of cancer. Monoterpenes are a major part of plant essential oils found largely in fruits, vegetables and herbs. The cellular and molecular activities show therapeutic progression that may reduce the risk of developing cancer by modulating the factors responsible for colon carcinogenesis. Colon cancer was induced with DMH with a dose of (20 mg/Kg/body weight) for 15 weeks by subcutaneous injection once in a week...
September 2015: Biomolecules & Therapeutics
Evgeniy V Suslov, Konstantin Yu Ponomarev, Artem D Rogachev, Michail A Pokrovsky, Andrey G Pokrovsky, Maria B Pykhtina, Anatoly B Beklemishev, Dina V Korchagina, Konstantin P Volcho, Nariman F Salakhutdinov
A series of secondary amines combining monoterpenoid and aminoadamantane moieties have been synthesized. Their cytotoxic activity against human cancer cells CEM-13, MT-4, and U-937 has been studied for the first time. Most of the obtained compounds exhibited a significant cytotoxic activity with the median cytotoxic dose (CTD50) ranging from 6 to 84 µM. The most promising results were obtained for compound 2b which was synthesized from 1-aminoadamantane and (-)-myrtenal and revealed a high activity against all tumor lines used (CTD50 = 12 ÷ 21 µM) along with low toxicity with respect to MDCK cells (CTD50 = 1500 µM)...
2015: Medicinal Chemistry
S Iravani, B Zolfaghari
Bark extract of Pinus pinaster contains numerous phenolic compounds such as catechins, taxifolin, and phenolic acids. These compounds have received considerable attentions because of their anti-inflammatory, antimutagenic, anticarcinogenic, antimetastatic and high antioxidant activities. Although P. pinaster bark has been intensely investigated in the past; there is comparably less information available in the literature in regard to P. eldarica bark. Therefore, the aim of this study was to determine the chemical composition of P...
July 2014: Research in Pharmaceutical Sciences
Manuel Honrado, Antonio Otero, Juan Fernández-Baeza, Luis F Sánchez-Barba, Andrés Garcés, Agustín Lara-Sánchez, Ana M Rodríguez
The reaction of bpzbeH, bpzteH (racemic mixture) or (R,R)-bpzmmH (enantiopure) with the amide complexes Zn{N(SiMe3)2}2 or Zn{N(SiHMe2)2}2 in 1 : 1 molar ratio in toluene afforded the mononuclear amide zinc complexes [Zn(NR2)(κ(3)-NNO)] (1-6) [κ(3)-NNO = bpzbe, R = SiMe3 1, SiHMe2 2; bpzte, R = SiMe3 3, SiHMe2 4; (R,R)-bpzmm, SiMe3 5, SiHMe2 6]. These complexes were employed in a protonolysis reaction with HCl-Et2O in 2 : 1 molar ratio to yield the dinuclear amide/chloride zinc complexes [Zn(κ(2)-NN-μ-O)2{ZnCl(NR2)}] (7-12) [κ(2)-NN-μ-O = bpzbe, R = SiMe3 7, SiHMe2 8; bpzte, R = SiMe3 9, SiHMe2 10; (R,R)-bpzmm, SiMe3 11, SiHMe2 12]...
December 7, 2014: Dalton Transactions: An International Journal of Inorganic Chemistry
Ayyasamy Rathinam, Leelavinothan Pari, Ramasamy Chandramohan, Bashir Ahmad Sheikh
This study aims to evaluate the efficacy of myrtenal, a natural monoterpene, for its antihyperglycemic effects and β cell protective properties in streptozotocin (STZ)-induced diabetic rats. Oral administration of myrtenal at doses of 20, 40, and 80 mg/kg body weight to diabetic rats for 28 days resulted in a significant reduction (P < 0.05) in the levels of plasma glucose, glycosylated hemoglobin (HbA1c), and an increase in the levels of insulin and hemoglobin (Hb). Protection of body weight loss of diabetic rats by myrtenal was noted...
December 2014: Journal of Physiology and Biochemistry
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