myrtenal

Baccharis dracunculifolia DC. and Baccharis microdonta DC. (Asteraceae) are woody species morphologically similar growing in Uruguay, where not taxonomists people often confuse them in field conditions. As the essential oil of B. dracunculifolia ('vassoura' oil) is highly prized by the flavor and fragrance industry, the correct differentiation of the two species is a key factor in exploiting them profitably and reasonably. To differentiate both Baccharis species, in this work their volatile expression profiles were studied as an alternative tool to determine authenticity and quality...

Lippia alba (Mill.) N. E. Br. (Verbenaceae) is an aromatic shrub whose essential oils have stood out as a promising source for application in several industrial fields. In this study, the essential oils chemical characterization of eight new L. alba genotypes was performed. The selected materials were collected from the Active Germplasm Bank of the Agronomic Institute and the essential oils were extracted by hydrodistillation. Flow-modulated comprehensive two-dimensional gas chromatography coupled to mass spectrometry (GC×GC-MS) was employed for chemical characterization and evaluation of possible co-eluted compounds...

The present study was undertaken to evaluate the chemopreventive activity of myrtenal, a natural monoterpene, against bladder carcinoma in rats induced with N-butyl-N-(4-hydroxybutyl)-nitrosamine (BBN) and promoted with γ-ionizing radiation (γ-IRR) as well as to assess the involvement of inflammation, apoptosis and oxidative damage in tumor development. Histopathological examination of rat bladder revealed the presence of noninvasive papillary transitional cell carcinoma (Grade 2) in sections from BBN group indicating the credibility of the applied carcinogenesis model...

Currently, the spectrum of agents against orthopoxviruses, in particular smallpox, is very narrow. Despite the fact that smallpox is well controlled, there is, for many reasons, a real threat of epidemics associated with this or a similar virus. In order to search for new low molecular weight orthopoxvirus inhibitors, a series of amides combining adamantane and monoterpene moieties were synthesized using 1- and 2-adamantanecarboxylic acids as well as myrtenic, citronellic and camphorsulfonic acids as acid components...

This study presented a micromorphological and phytochemical survey on Lavandula dentata L. cultivated at the Ghirardi Botanic Garden (Toscolano Maderno, BS, Italy). The morphological investigation revealed the presence of peltate, short- and medium-stalked capitate trichomes. The histochemical survey showed terpenes production by peltates and medium-stalked capitates, hydrophilic secretions by short-stalked capitates. The phytochemical survey was developed on leaf and flower volatile organic compounds (VOCs) and on the essential oil (EO) from the flowering aerial parts...

Hydrates of myrtenal (C10 H14 O) · (H2 O)n (n = 1, 2, 3) were experimentally investigated in a molecular jet using a cavity-based Fourier transform microwave spectrometer in the 2.6 GHz-15 GHz frequency range. The assignment of the spectra was made possible, thanks to computationally optimized structures at the B3LYP-D3BJ/def2-TZVP and MP2/6-311++G(d,p) levels using the Gaussian 16 software. The spectra of two mono- and two dihydrates and those of the lowest energy conformer among the two expected trihydrates could be assigned...

We report the preparation of enantiomerically pure constrained geometry complexes ( cgc ) of the rare-earth metals bearing a pentadienyl moiety (pdl) derived from the natural product (1 R )-(-)-myrtenal. The potassium salt 1 , [Kpdl*], was treated with ClSiMe 2 NH t Bu, and the resulting pentadiene 2 was deprotonated with the Schlosser -type base KO t Pen/ n -BuLi ( t Pen = CMe 2 (CH 2 Me)) to yield the dipotassium salt [K 2 (pdl*SiMe 2 N t Bu)] ( 3 ). However, 3 rearranges in THF solution to its isomer 3' by a 1,3-H shift, which elongates the bridge between the pdl and SiMe 2 N t Bu moieties by one CH 2 unit...

Schinus polygamus (Anacardiaceae) is a shrub cultivated in Egypt for ornamental purpose. The major components of bark oil were dl -limonene (29.74%), followed by myrtenal (14.02%) and caryophyllene oxide (11.34%), while E -caryophyllene (55.86%), dl -limonene (27.71%) and β -pinene (3.54%) were predominant in the leaf oil. These isolated oils were screened for their antimicrobial activity against Staphylococcus aureus ATCC 33591 , Staphylococcus aureus ATCC 29213, Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 10145, Candida albicans MTCC183 and Aspergillus niger NRRL 595, and two clinical isolates of Staphylococcus aureus ...

BACKGROUND: We found in the literature, an excellent review of the Biginelli reaction that addresses the methodologies for obtaining enantiopure dihydropyrimidinones (DHPMs). In 1992, optically pure DHPMs were obtained by fractional crystallization of the diastereomeric ammonium salt derivative with (S)-(-) and (R)- (+)-α-methyl benzylamine and by other chiral resolution techniques, such as chiral high-performance liquid chromatography (HPLC). Asymmetric syntheses of these compounds are also explained in the literature...

Myrtenal is a natural monoterpene isolated from essential oils of several plants and their derivates have shown to have several biological properties including cytotoxicity. The cytotoxic activity of these derivates are being investigated for their antitumor effect leading to the development of potential anticancer agents. In this study, novels Myrtenyl grafted pseudo-peptides were designed, synthesized and functionally characterized as possible therapeutic agents for cancer treatment. Thirteen novel Myrtenyl grafted pseudo-peptides were prepared in high atom economy and efficiency by a classic Ugi-4CR and sequential post-modification...

ConspectusFrom structure elucidation and biogenesis to synthetic methodology and total synthesis, terpene natural products have profoundly influenced the development of organic chemistry. Moreover, their myriad functional attributes range from fragrance to pharmaceuticals and have had great societal impact. Ruzicka's formulation of the "biogenetic isoprene rule," a Nobel Prize winning discovery now over 80 years old, allowed for identification of higher order terpene (aka "isoprenoid") structures from simple five-carbon isoprene fragments...

We compared the neuroprotective action of three natural bio-antioxidants (AOs): ellagic acid (EA), α-lipoic acid (LA), and myrtenal (Myrt) in an experimental model of Parkinson's disease (PD) that was induced in male Wistar rats through an intrastriatal injection of 6-hydroxydopamine (6-OHDA). The animals were divided into five groups: the sham-operated (SO) control group; striatal 6-OHDA-lesioned control group; and three groups of 6-OHDA-lesioned rats pre-treated for five days with EA, LA, and Myrt (50 mg/kg; intraperitoneally- i...

The present work is an extensive laboratory study of organosulfate (OS) formation from the reaction of α-pinene oxidation products or proxies with acidified ammonium sulfate aerosols in three different acidity conditions ((NH4)2SO4 0.06 M; (NH4)2SO4/H2SO4 0.06 M/0.005 M; (NH4)2SO4/H2SO4 0.03 M/0.05 M). The kinetics of the reactions of α-pinene, α-pinene oxide, isopinocampheol, pinanediol and myrtenal with ammonium sulfate particles were studied using a quasi-static reactor. The reaction of α-pinene oxide with the highly acidic ammonium sulfate particles was determined to be 7, 10, 21 and 24 times faster than for isopinocampheol, α-pinene, pinanedial and myrtenal, respectively for an OS precursor concentration of 1 ppm and after 1h reaction time...

The present study was aimed to investigate the effect of myrtenal on diabetes-associated oxidative stress, lipid peroxidation (LPO), and inflammation using a rat model of streptozotocin (STZ)-induced diabetes. Following the induction of diabetes in male Wistar rats using STZ (40 mg/kg body weight), myrtenal (80 mg/kg body weight) was administered orally to diabetic rats for four weeks and then sacrificed to harvest tissues. We measured the levels of antioxidants, LPO, and proinflammatory cytokines such as tumor necrosis factor-α (TNF-α) and interleukin 6 (IL-6), and the p65 subunit of nuclear factor-kappa B (NF-kB p65)...

Culex pipiens is a main vector for Bancroftian filariasis, Rift Valley Fever and diseases caused by other viruses, leaving several peoples with disabilities. In recent years, plant derived compounds have received much attention as potential alternatives to synthetic chemicals due to their low toxicity to mammals and environmental persistence. Twenty-one monoterpenes from different chemical groups (hydrocarbons and oxygenated products) were evaluated against Culex pipiens larvae. In addition, in vivo biochemical studies including effects on acetylcholine esterase (AChE), acid and alkaline phosphatases (ACP and ALP), total adenosine triphosphatase (ATPase) and gamma-aminobutyric acid transaminase (GABA-T) were investigated...

BACKGROUND: Insect pheromones and host volatiles are important for pest control due to their high efficiency and low potential for environmental pollution. The functions of myrtenol, myrtanol and myrtenal in pest-host interactions are unknown. This study aimed to determine the presence of myrtenol, myrtanol and myrtenal in newly emerged and emerged stages of Dendroctonus armandi and in infected and healthy Pinus armandi, and to identify their roles in tree protection and pest management based on electroantennography (EAG), Y-tube and toxicity experiments...

The enantiomerically pure pentadienyl (Pdl*) ligand derived from the natural product (1R)-(-)-myrtenal forms with MCl3 (M = La, Ce, Pr, and Nd) the corresponding homoleptic [(η5-U-Pdl*)3M compounds (1-M). These complexes were fully characterised by 1H NMR spectroscopy, elemental analyses and X-ray diffraction. They exhibit in solution and solid state idealized C3 symmetry, and their molecular structures also reveal that the Pdl* ligand adopts a U-conformation and coordinates exclusively with its less sterically encumbered face to the rare-earth metal atom...

By the reaction of an enantiopure nitronyl nitroxide radical, 2-((1 R)-(-)-myrtenal)-4,4,5,5-tetramethylimidazolin-1-oxyl-3-oxide), abbreviated as (1 R)-(-)-myrtenal-NIT, and Dy(hfac)3 ·2H2 O (hfac = hexafluoroacetylacetonate), we successfully obtained a homochiral DyIII -radical chain compound [Dy(hfac)3 (1 R)-(-)-myrtenal-NIT] n (1) with full characterization. 1 crystallizes in the chiral P21 space group and exhibits slow magnetization relaxation, holding an effective energy barrier (Δτ / kB ) of 64.6 K (44...

BACKGROUND: Metastatic tumor cells have acidic extracellular pH and differential electrochemical H+ gradients generated across their cell membranes by V-type H+ -ATPases. This study shows that inhibition of the V-ATPases by the plant-derived monoterpene Myrtenal results in tumor cell death and decreased metastatic dissemination in mice. METHODS: The Myrtenal anticancer toxicity was evaluated in vitro using murine (B16F0 and B16F10) and human (SkMel-5) melanoma cell lines, and in in vivo mouse metastatic dissemination model...

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...