Showing papers on "Terpene published in 1992"

Identification of metabolites of the antitumor agent d-limonene capable of inhibiting protein isoprenylation and cell growth.

Abstract: Limonene has been shown to be an effective, nontoxic chemopreventive and chemotherapeutic agent in chemically induced rat mammary-cancer models. The present study characterized circulating metabolites of limonene in female rats and determined their effects on cell growth. Metabolism of limonene was analyzed in plasma extracts by gas chromatography. Rapid conversion of limonene to two major metabolites was detected. These metabolites comprised more than 80% of the circulating limonene-derived material at 1 h after administration and thereafter, whereas limonene itself accounted for only 15%. The metabolites were characterized by mass spectroscopy and infrared spectroscopy. The probable structures were synthesized, and identities were confirmed by comparison of retention times and mass spectra. The two major circulating metabolites of limonene were found to be perillic acid and dihydroperillic acid. We have previously reported that limonene, perillic acid, and dihydroperillic acid inhibit the posttranslational isoprenylation of p21ras and other 21- to 26-kDa cell-growth-associated proteins in NIH3T3 cells and in mammary epithelial cells. In the present study, perillic acid was found to inhibit cell growth in a dose-dependent manner. Thus, perillic acid and dihydroperillic acid, the two major circulating metabolites of limonene in the rat, are more potent inhibitors of protein isoprenylation than is limonene, and perillic acid is also a more potent inhibitor of cell growth. These data raise the possibility that the antitumor effects of limonene in vivo may be mediated via perillic acid and, perhaps, other metabolites.

Enantioselective Synthesis: Natural Products from Chiral Terpenes

Abstract: Citronellene, Citronellol, Linalool and their Oxidized Derivatives Limonene Menthone, Piperitone, Perillaldehyde and Related Compounds Pulegone Carvone Carenes and Thujone Pinenes Camphor and Congeners Other Terpenes

Terpenes in sponge cell-membranes - cell-separation and membrane fractionation studies with the tropical marine sponge amphimedon-sp

Abstract: The differing sponge and symbiotic microbial cell types in the tropical marine spongeAmphimedon sp. were fractionated according to density, investigated by electron microscopy, and analyzed by high-performance liquid chromatography and nuclear magnetic resonance for the presence of the terpene metabolite diisocyanoadociane (1) and Δ5,7-sterols (2–7). A sample of whole sponge was dissected into superficial ectosome and deeper choanosome. The superficial tissue was found to be enriched in sterol relative to choanosome; however, extracts from both tissues contained terpene. Dissociation of whole sponge followed by Ficoll density gradient fractionation showed that there are two chemically distinct types of sponge cells inAmphimedon sp.—small non-nucleolated cells of low density contain terpene 1 together with sterols, while larger nucleolated cells contain significant levels of terpene, but only traces of sterol. Membrane fractionation studies were undertaken to establish whether the terpene components were located specifically in the cell membranes of these two cell types. A membrane vesicle pellet spun down at 100,000×g from small sponge cells contained sterols, but only traces of terpene, whereas the membrane vesicle preparation from heavier cells contained both terpenes and sterols. Subsequently, the presence of terpenes together with sterols was demonstrated in a membrane vesicle preparation of purity >90% prepared from bacteria-free sponge cells. These results provide the first experimental evidence that terpenes are associated with sponge cell membranes, where they may function as structural components.

Stereochemistry of α-Amino Oximes From the Monoterpene Hydrocarbons Car-3-ene, Limonene and α-Pinene

Abstract: The conformation and configuration of the α-amino oximes derived from the terpene hydrocarbons car-3-ene, limonene and α- pinene have been determined by n.m.r. spectroscopy (high-field 1H n.m.r., 13C n.m.r., INADEQUATE technique), molecular mechanics calculations and X-ray crystallographic analysis. The crystal structure of (lS,3S,6R)-3-dimethylamino-caran-4-one (E)-oxime has been determined by X-ray diffraction; crystals are orthorhombic, space group P 212121 with a 11.421(2), b 13.223(2), c 16.992(4) A, Z 8. Refinement on 1730 observed reflections measured with Cu K α radiation converged at R 0.053.

Comparison of the volatile compounds from several commercial plum cultivars

Abstract: Volatile fractions were prepared from five ripe commercial plum cultivars and one breeding line by continuous vacuum steam distillation-hexane extraction and analyzed by capillary GC and GC-MS. Thirty-six compounds were identified. The eight major compounds for most cultivars were hexenal, butyl acetate, (E)-2-hexenal, butyl butyrate, hexyl acetate, linalool, γ-decalactone, and γ-dodecalactone. Minor constituents included eleven esters, two alcohols, four lactones, two terpenes, two saturated hydrocarbons, palmitic acid, three phenyl compounds and nonanal.

Technique for using microencapsulated terpenes in lepidopteran artificial diets.

Abstract: We have developed and tested a technique to microencapsulate terpene compounds by forming gelatin-walled microcapsules around the terpene essential oils. Eight terpenes that are common constituents of Douglas fir (Pseudotsuga menziesii) oleoresin were encapsulated, including five monoterpenes (α-pinene,β-pinene, camphene, myrcene, and limonene) and three oxygenated monoterpenes (bornyl acetate, linalool, andβ-citronellol). The encapsulated terpenes were mixed into artificial diets to determine the effects they had on western spruce budworm (Choristoneura occidentalis) survival and reproduction, using a three-generation bioassay. We describe the technique and present data from preliminary bioassays with seven of the terpenes to demonstrate thatC. occidentalis larvae would consume diets fortified with microencapsulated terpenes. The technique is useful because it helps to reduce the rate at which terpenes volatilize from the diets and it “packages” the terpenes in a manner more closely resembling the way they are present in the resin canals of plant foliage. Many scientists investigating the biological importance of terpenes in mediating plant-herbivore interactions may find that microencapsulated terpenes are useful in both laboratory diet studies and field and greenhouse experiments with plant material.

Inhibitory effects of terpene alcohols and aldehydes on growth of green algaChlorella pyrenoidosa.

Abstract: The growth of the green algaChlorella pyrenoidosa was inhibited by terpene alcohols and the terpene aldehyde citral. The strongest activity was shown by citral. Nerol, geraniol, and citronellol also showed pronounced activity. Strong inhibition was linked to acyclic terpenes containing a primary alcohol or aldehyde function. Inhibition appeared to be taking place through the vapor phase rather than by diffusion through the agar medium from the terpene-treated paper disks used in the system. Inhibition through agar diffusion was shown by certain aged samples of terpene hydrocarbons but not by recently purchased samples.

Terpenes Emitted to Air from Forestry and the Forest Industry

Abstract: A major environmental concern with respect to hydrocarbon emissions is the formation of phytotoxic photooxidants. The work reported in this thesis focusses on the poorly studied anthropogenic terpene emissions from the industrial use of softwood. The advanced analytical determinations were made by adsorption sampling followed by thermal desorption and gas chromatography in the laboratory. Monoterpenes from forestry were analyzed for Scots pine (Pinus sylvestris) and Norway spruce (Picea abies). Near to a harvester, the total monoterpene concentrations reached ~1000 mg/m 3 , whereas the background level was ~1 mg/m 3 . Prominent monoterpenes were a-pinene, b-pinene, 3-carene, camphene, limonene, b-phellandrene, myrcene and terpinolene. Local formation of phytotoxic photooxidants may occur because of the short lifetimes of terpenes in air. Terpenes in process emissions and plumes from kraft pulp industries were found to have a uniform composition similar to that of pulpwood and of recovered sulphate turpentine. Predominant monoterpenes were a-pinene and 3-carene from Scots pine. The emitted terpenes give rise to photooxidants and to oxidation of co-emitted sulphur and nitrogen oxides. The monoterpenes in emissions from industries producing stone groundwood and thermomechanical pulp were similar in composition to that of the processed pulpwood from Norway spruce. The major monoterpenes were a-pinene (>50%) and b-pinene (~25%). The process emissions from a sulphite mill consisted mainly of p-cymene, formed from spruce monoterpenes by acid rearrangements. The terpene emissions from the barking of timber and pulpwood differed somewhat in composition from that of the wood. Increased proportions of b-phellandrene and myrcene were observed for Norway spruce. Oxidative decomposition and acid rearrangements of monoterpenes in the sampling cartridges were studied as major analytical difficulties. Pretreatment with thiosulphate and hydrogencarbonate prevented unwanted reactions of the terpenes.

Phenotypic Plasticity in Mentha viridis lavanduliodora

Abstract: Mentha viridis L. cult, lavanduliodora Sacco was characterized by high levels of linalool and linalyl acetate. The same features were found in a F1 population coming from seed. Phenotypic plasticity, genotypic variability and genotypic variation for phenotypic plasticity were studied by analyzing essential oils distilled from flowering F1 hybrids during two growing seasons: 1989 and 1990. The oils were analyzed by GC/MS: limonene, 1, 8-cineole, linalool, linalyl acetate, β-caryophyllene, α-terpineol and geraniol were found to be the main compounds and were statistically processed. The linalool/linalyl acetate (R1) and 1, 8-cineole/limonene (R2) ratios were also calculated and statistically processed. Two-way AN OVA, Clusters Analysis (CA) and Principal Component Analysis (PCA) were used to evaluate genotypic variability and phenotypic plasticity respectively; statistical linkage as well as pattern and structure of terpenes and partition among plants. The results showed high genotypic variability ...

Fungicidal composition based on copper tallate with terpene derivatives, and its production

Abstract: This composition is characterised in that it contains terpene derivatives based on alcohols and terpene hydrocarbons. The copper phthalate is obtained from a mixture of fatty acids and resinic acids which are actually present in the terpene derivatives used in the composition.

Density of α-pinene, Β-pinene, limonene, and essence of turpentine

Abstract: Densities of ga-pinene, Β-pinene, limonene, and essence of turpentine have been measured at 293.15, 298.15, 303.15, 308.15, and 313.15 K, at atmospheric pressure, with a mechanical oscillator densimeter. Benzene and cyclohexane were used as calibration fluids. The precision is of the order of 0.01 kg · m−3, while the accuracy is estimated to be 0.1%. A linear representation of the variation of the density with temperature reproduces the experimental data within 0.2%.

Novel Neurotrophic Isocuparane‐Type Sesquiterpene Dimers, Mastigophorenes A, B, C and D, Isolated from the Liverwort Mastigophora diclados.

Abstract: Four dimeric isocuparane-type sesquiterpenes, mastigophorenes A, B, C and D, isolated together with a new 3,4-dihydroxylated isocuparene from the liverwort Mastigophora diclados, have been assigned structures on the basis of detailed spectroscopic analyses. Among them, mastigophorenes A, B and D have been found to accelerate neuritic sprouting at 10–5–10–7 mol dm–3 in a neuritic cell culture of foetal rat cerebral hemisphere; their biosynthesis, initiated by phenolic oxidation of (–)-herbertenediol, is proposed.

Bicyclic diterpene PAF antagonist compounds

Abstract: Four bicyclic terpenes isolated from a culture broth of Phoma sp SCF0592, ATCC 74077, pharmaceutical compositions containing them and their use as PAF antagonists to treat allergic and inflammatory diseases are disclosed.

Comparison of Two Monoterpene Cyclases Isolated from Higher Plants; γ-Terpinene Synthase from Thymus Vulgaris, and Limonene Synthase from Mentha x Piperita

Abstract: Monoterpenes are the C10 members of the terpenoid family of natural products, and they diverge from higher isoprenoid biosynthesis at the level of geranyl pyrophosphate. γ-Terpinene synthase and limonene synthase catalyze the divalent metal ion-dependent cyclization of geranyl pyrophosphate to cyclic monoterpenes of the p-menthane type; however, γ-terpinene synthase generates a diverse assortment of minor monoterpene co-products from geranyl pyrophosphate whereas limonene synthase produces a single product. The basic physical and chemical characteristics of these two monoterpene cyclases are described and compared to properties of other terpene cyclases.

Process for extracting plant essential oils by cold maceration and by cold removal of terpenes

Abstract: Extraction of essential oils of plant origin in a substantially pure state by cold maceration of the plants in a solvent permitting the extraction, without preliminary grinding, the concentration and the cold removal of terpenes from the essences, ensuring: - a better quality (essences obtained strictly pure after terpene removal), - a better economic yield. With recovery of the solvent by phase separation and the removal of the last traces of the solvent by evaporation. Also separation of the terpenes from the essences with the aid of alcohol. Recovery of the terpenes. Separation of the "essence-alcohol" mixture under the action of a salt. Recovery of the essence; also recovery of the solution which has allowed the terpenes to be separated off.

Synthesis of Physiological Active Terpenes. Part VI. Synthesis and Physiological Activity of Monoterpene Carboxypyrrolidinamides and Piperidinamides.

Abstract: The monoterpene aldehydes (-)-myrtenal, (-)-perillaldehyde, and (+)-α-campholenic aldehyde were converted to nitriles by sequential N, N-dimethylhydrazonation, methylation, and an elimination reaction of the Hofmann-type. The nitriles were converted to terpenoyl chlorides by hydrolysis and chlorination with thionyl chloride. The chlorocarbonylated terpenes were condensed with pyrrolidine, 2-, 3-, or 4-methylpiperidines, and 2, 6- or 3, 5-dimethylpiperidines to obtain 21 terpene amides in 11_??_36% overall yields for the four steps starting from the imidation of the terpene aldehydes. The bactericidal and fungicidal activities of these amides toward Puccinia recondita ROBERGE (wheat leaf rust), Phytophthora infestans (MONT.) de BARY, and Erysiphe graminis D. C. (f. sp. tritici MARCHAL). 2, 6-Dimethyl-1-[2-(2, 2, 3-trimethyl-cyclopentyl-3-ene) acetoyl] piper idine at 300 ppm prevented the growth of Puccinia recondita ROBERGE in a pot test. When used to treat Disbrotica longicornis SAY, Spodoptera frugiperda J. E. SMITH, and Tetranychus urticae KOCH, 1-(6, 6-dimethylbicyclo-[3.1.1] hepto-2-ene-2-carbonyl)-2-methylpiperidine at 300 ppm almost completely eradicated Disbrotica longicornis SAY (corn rootworm) in soil treated with the amide. 1-(4-Isopropenyl-l-cyclohexene-l-carbonyl) pyrrolidine at 300 ppm inhibited the germination and growth of Lycopersicon esculentum MILL. (tomato), but had no effect on Echinochloa crus-galli BEAUV., Setaria viridis BEAUV., Tagetes sp.; and Abutilon theophrasti MODIK. The other amides at the concentration of 300 ppm had little or no activity.