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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-OSO3H) 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
Xirui Hu, Thomas J Maimone
A four-step synthesis of the antimalarial terpene cardamom peroxide, a 1,2-dioxepane-containing natural product, is reported from (-)-myrtenal and molecular oxygen. This highly concise route was guided by biosynthetic logic and enabled by an unusual manganese-catalyzed, tandem hydroperoxidation reaction. The absolute configuration of the cardamom peroxide is reported, and its mode of fragmentation following Fe(II)-mediated endoperoxide reduction is established. These studies reveal the generation of reactive intermediates distinct from previously studied endoperoxide natural products...
April 9, 2014: Journal of the American Chemical Society
Ana T Rufino, Madalena Ribeiro, Fernando Judas, Lígia Salgueiro, Maria C Lopes, Carlos Cavaleiro, Alexandrina F Mendes
Previous studies have suggested that α-pinene, a common volatile plant metabolite, may have anti-inflammatory effects in human chondrocytes, thus exhibiting potential antiosteoarthritic activity. The objective of this study was to further characterize the potential antiosteoarthritic activity of selected pinene derivatives by evaluating their ability to modulate inflammation and extracellular matrix remodeling in human chondrocytes and to correlate the biological and chemical properties by determining whether the effects are isomer- and/or enantiomer-selective...
February 28, 2014: Journal of Natural Products
S Jonsson, G Bergström, B S Lanne, U Stensdotter
The emission of species-specific odors byPristiphora erichsonii andP. wesmaeli is accompanied by a characteristic defensive behavior called "snap bending." When the larvae are disturbed, blends of volatile compounds are emitted from ventral glands. The odor ofP. erichsonii, a colonial species, is composed of bornyl acetate, borneol,trans-pinocarveol, myrtenol, benzaldehyde, and tetradecyl, hexadecyl, and octadecyl acetates, whereas that of the solitaryP. wesmaeli is composed of 3-carene-10-al, linalool, myrtenal, and benzaldehyde...
February 1988: Journal of Chemical Ecology
T W Phillips, J L Nation, R C Wilkinson, J L Foltz
Controlled infestation ofDendroctonus terebrans (Olivier) on bolts of slash pine,Pinus ellionii Engelm. var.elliottii, elicited greater attraction of wild conspecifics than uninfested bolts. Secondary attraction was not apparent, however, to standing slash pines that had received volunteer attacks, when compared with attraction to unattacked but susceptible trees. Hindguts from in-flight or attacking femaleD. terebrans contained frontalin, and those from in-flight or attacking males containedexo-brevicomin...
May 1989: Journal of Chemical Ecology
R Ramachandran, Z R Khan, P Caballero, B O Juliano
Electroantennograms (EAGs) were recorded from male and female moths of two sympatric leaf folder species,Cnaphalocrocis medinalis (Gue-née) andMarasmia patnalis Bradley (Lepidoptera: Pyralidae) to 91 volatile chemicals of plant origin. Responses of both leaf folder species were similar to all compounds except to three monoterpenes-β-myrcene, menthone, and isomenthone- and two sesquiterpenes-cis-nerolidol and isophytol. Response ofM. patnalis, an oligophagous leaf folder, to these compounds was higher compared with that of polyphagousC...
September 1990: Journal of Chemical Ecology
J C Grégoire, M Baisier, A Drumont, D L Dahlsten, H Meyer, W Francke
During a laboratory study evaluatingRhizophagus grandis (a specific native predator of the Eurasian bark beetle,Dendroctonus micans), as a potential biocontrol agent against the North American bark beetle,Dendroctonus valens, it was found that feeding larvae and laboratory-produced frass of the potential prey elicited very high oviposition responses in the predator. Comparative chemical analysis of this laboratory-produced larval frass revealed that one major volatile compound, (-)-fenchone, is associated with the larvae of bothDendroctonus species...
October 1991: Journal of Chemical Ecology
J Hardie, R Isaacs, J A Pickett, L J Wadhams, C M Woodcock
Methyl salicylate and (-)-(1R,5S)-myrtenal stimulate specific olfactory cells in the primary rhinaria on the sixth and fifth antennal segments, respectively, of the black bean aphid.Aphis fabae. In behavioral studies employing a linear track olfactometer, both compounds were repellent toA. fabae and also inhibited attraction to volatiles from its host, broad bean (Vicia faba). Methyl salicylate is associated with secondary metabolite-based defense in plants, and the monoterpenoid (-)-(1R,5S)-myrtenal is metabolically related to (-)-(1S,5S)-α-pinene, an abundant component of defensive resins produced by gymnosperms...
November 1994: Journal of Chemical Ecology
Igor Jerković, Piotr Marek Kuś, Carlo Ignazio Giovanni Tuberoso, Mladenka Šarolić
The case study of Polish Salix spp. honey was compared with published data on willow honey from other regions. GC-FID/MS (after HS-SPME and ultrasonic solvent extraction) and targeted HPLC-DAD were applied. Phenolic content, FRAP/DPPH assays and the colour coordinates were determined spectrophotometrically. Beside ubiquitous linalool derivatives, borneol (up to 10.9%), bicyclic monoterpenes with pinane skeleton (pinocarvone up to 10.6%, myrtenal up to 4.8% and verbenone up to 3.4%) and trans-β-damascenone (up to 13...
February 15, 2014: Food Chemistry
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