Showing papers on "Terpene published in 1991"
TL;DR: The penetration enhancers increased drug diffusivity through the membranes, an effect which correlated empirically with the enhancer activities, and the accelerant effects were not due to partitioning phenomena.
Abstract: A series of terpenes has been assessed as skin penetration enhancers towards the model polar penetrant 5-fluorouracil (5-FU). Cyclic terpenes were selected from the chemical classes of hydrocarbons (e.g., α-pinene), alcohols (e.g., α-terpineol), ketones (e.g., carvone), and oxides (e.g., 1,8-cineole, ascaridole). Permeation experiments were performed on excised human epidermal membranes and the terpenes varied in their activities; α-pinene only doubled the permeability coefficient of aqueous 5-FU, whereas 1,8-cineole caused a near 95-fold increase. Essential oils, e.g., chenopodium (70% ascaridole), were less effective than the corresponding isolated terpenes. 5-FU is less soluble in the terpenes than in water, and the terpenes did not exert their action by increasing partitioning of the drug into the membranes as illustrated by stratum corneum:water partitioning studies. The penetration enhancers increased drug diffusivity through the membranes, an effect which correlated empirically with the enhancer activities. The principal mode of action of these accelerants may be described by the lipid–protein–partitioning theory; the terpenes interacted with intercellular stratum corneum lipids to increase diffusivity, and the accelerant effects were not due to partitioning phenomena. Keratin interaction was assumed negligible.
529 citations
Book•
01 Jan 1991
TL;DR: In this article, the main terpenoid types are described: hemiterpenoids monoterpenoids sesquiterpenoid diterpoids sesterperpenoids triterpoid tetraterpenoids polyterpenoids.
Abstract: Description of main terpenoid types hemiterpenoids monoterpenoids sesquiterpenoids diterpenoids sesterperpenoids triterpenoids tetraterpenoids polyterpenoids.
440 citations
TL;DR: The antimicrobial activity of 20 10% solutions in ethanol of terpenes and terpenoids at several concentrations was tested against Erwinia amylovora NCPPB 595 in the liquid medium 523 and β-terpinene was more effective when challenged with larger numbers of cells.
Abstract: The antimicrobial activity of 20 10% (v/v) solutions in ethanol of terpenes and terpenoids at several concentrations was tested against Erwinia amylovora NCPPB 595 in the liquid medium 523. The test organism responded differently to the chemicals. At 600, 900 and 1200 mg/l, none of the compounds reduced the growth of the bacterium. At 1500 mg/l, only some of the chemicals significantly inhibited growth x-Pinene. β-terpinene, dihydrocarveol, isopulegol and linalool reduced growth of suspensions of 1 × 103 cfu/ml, whereas β-pinene was more effective when challenged with larger numbers of cells (i.e. 1 × 105 cfu/ml and 1 × 107 cfu/ml). At 1500 mg/l, geraniol and citronellol exerted a bactericidal activity regardless of the concentrations of the test organism.
204 citations
TL;DR: In this paper, a series of cyclic monoterpenes were assessed as skin penetration enhancers towards a model lipophilic drug, oestradiol, and a novel concept, enhancement index, was introduced to compare differences in terpene activities towards the two permeants.
144 citations
TL;DR: The terpene phenols thymol and carvacrol represent the most important compounds in the genus Thymus, followed by linalool, p-cymene, γ-terpinene, borneol, terpinen-4-ol and 1, 8-cineole.
Abstract: From 1960 to 1989 more than 80 Thymus taxa from 27 different countries all over the world have been investigated for the composition of their essential oils. About 200 different compounds, mostly terpenes, have been identified. The terpene phenols thymol and carvacrol represent the most important compounds in the genus, followed by linalool, p-cymene, γ-terpinene, borneol, terpinen-4-ol and 1, 8-cineole. This paper lists the main components of the essential oils of all the taxa investigated from 1960 to 1989. In addition, seasonal variations of Thymus oils and essential oil polymorphism within the genus Thymus are also reported.
136 citations
Book•
01 Jan 1991
TL;DR: In this article, the authors present a list of METABOLISM of NITRILES, NITRO COMPOUNDS, AMIDES, and other ALIPHATIC NITRALOIDS.
Abstract: METABOLISM OF HYDROCARBONS. ALIPHATIC HYDROCARBONS. MONOTERPENOID HYDROCARBONS. Acyclic Terpene Hydrocarbons. Monocyclic Terpene Hydrocarbons. Bicyclic Terpene Hydrocarbons. AROMATIC HYDROCARBONS. METABOLISM OF ALCOHOLS. ALIPHATIC ALCOHOLS. MONOTERPENOID ALCOHOLS. Acyclic Terpene Alcohols. Monocyclic Terpene Alcohols. Bicyclic Terpene Alcohols. AROMATIC ALCOHOLS. METABOLISM OF PHENOLS AND ETHERS. PHENOLS. ETHERS. METABOLISM OF ALDEHYDES, KETONES, AND QUINONES. ALDEHYDES. Aliphatic Aldehydes. Monoterpenoid Aldehydes. Aromatic Aldehydes. KETONES. Aliphatic Ketones. Monoterpenoid Ketones. Aromatic Ketones. QUINONES. Naphthoquinones. Anthraquinones. METABOLISM OF ACIDS, LACTONES, AND ESTERS. ACIDS. Aliphatic Acids. Alicyclic Acids. Aromatic Acids. LACTONES. ESTERS. METABOLISM OF HIGHER TERPENOIDS. SESQUITERPENOIDS. DITERPENOIDS. Linear Derivatives. Abietane Derivatives. Kaurane Derivatives. Taxane Derivatives. Cassane Derivatives. Other Derivatives. TRITERPENOIDS. Ursane Derivative s. Oleanane Derivatives. Dammarane Derivatives. Cycloartane Derivatives. Cardiac Steroids. Miscellaneous Steroids. TETRATERPENOIDS. METABOLISM OF OXYGEN HETEROCYCLIC COMPOUNDS. FURANS. PYRONES. a-Pyrones. g-Pyrones. CHROMAN, CHROMENE, CHROMANONE, AND CHROMONE DERIVATIVES. Chroman Derivatives. Chromene Derivatives. Chromanone Derivatives. Chromone Derivatives. COUMARINS. Coumarin. Coumarin Derivatives Containing Hydroxy and/or Methoxy Groups. Coumarin Derivatives Containing More Complex Substituents. FLAVONOIDS. Flavones. Flavonols. Flavanones. Anthocyanins. Catechins. Dihydrochalcones and Chalcones. Isoflavonoids. XANTHONES. OTHER OXYGEN HETEROCYCLIC COMPOUNDS. METABOLISM OF AMINO COMPOUNDS. METABOLISM OF NITRILES, NONPROTEIN AMINO ACIDS, NITRO COMPOUNDS, AMIDES, AND OTHER ALIPHATIC NITROGEN COMPOUNDS. NITRILES. NONPROTEIN AMINO ACIDS. NITRO COMPOUNDS. AMIDES. OTHER ALIPHATIC NITROGEN COMPOUNDS. METABOLISM OF NITROGEN HETEROCYCLIC COMPOUNDS. PYRROLIDINE DERIVATIVES. PIPERIDINE D ERIVATIVES. PYRIDINE DERIVATIVES. PYRAZINE DERIVATIVES. TROPANE DERIVATIVES. INDOLE DERIVATIVES. QUINOLINE DERIVATIVES. ISOQUINOLINE DERIVATIVES. MORPHINAN DERIVATIVES. PYRROLIZIDINE DERIVATIVES. IMIDAZOLE DERIVATIVES. QUINOLIZIDINE DERIVATIVES. PURINE DERIVATIVES. OTHER ALKALOIDS. METABOLISM OF SULFUR COMPOUNDS. THIOLS. SULFIDES. DISULFIDES. SULFONIUM COMPOUNDS. SULFOXIDES. GLUCOSINOLATES. THIAZOLES. INDEX.
128 citations
TL;DR: In vitro results show that the terpene β‐myrcene is not mutagenic in mammalian cells, but has antimutagenic properties, and the possibility that myrcene exerts its antimUTagenic activity by inhibiting certain forms of the cytochrome P‐450 isoenzymes required for activation of premutagens and precarcinogenes is discussed.
Abstract: The genotoxicity of the terpene beta-myrcene was evaluated in mammalian cells in vitro. Myrcene is the major constituent of oil of bay and hop which are used in the manufacture of alcoholic beverages. Myrcene is also present in lemon grass (Cymbopogon citratus), a plant widely used in Brazilian folk medicine. Recently, it was shown that myrcene is a very potent analgesic substance and might be an alternative to the already available analgesic drugs. Myrcene was tested up to 1,000 micrograms/ml (limit of solubility) in the presence and absence of S9-mix and did not induce chromosome aberrations and sister chromatid exchanges (SCEs) in human lymphocytes in vitro. Neither the mitotic index nor the proliferation index was influenced by the myrcene treatment. Myrcene did not cause increased mutation frequencies at the hprt-locus in V79-cells. Tests with and without S9-mix revealed negative results. There was no indication for induced cytotoxicity. However, myrcene reduced the SCE-inducing effect of cyclophosphamide in human lymphocytes in a dose dependent manner and also reduced the toxic and mutagenic effect of cyclophosphamide in V79-cells. Under the same test conditions, SCE induction by ethyl methanesulfonate (EMS) and benzo [a]pyrene (BP) was not significantly influenced by simultaneous myrcene treatment. The in vitro results show that myrcene is not mutagenic in mammalian cells, but has antimutagenic properties. The possibility that myrcene exerts its antimutagenic activity by inhibiting certain forms of the cytochrome P-450 isoenzymes required for activation of premutagens and precarcinogenes is discussed.
73 citations
TL;DR: Synthesis of Furanoid terpenes via an Efficient Palladium-Catalyzed Cyclization of 4,6-Dienols as mentioned in this paper, using a Palladium catalyst.
Abstract: Synthesis of Furanoid Terpenes via an Efficient Palladium-Catalyzed Cyclization of 4,6-Dienols
39 citations
TL;DR: In this article, the double bond of the resulting α,β-unsaturated terpene alcohols was further hydrogenated to form the corresponding saturated TERPENE alcohols, and a small amount of terpenic acids was also formed.
31 citations
TL;DR: A comparison of the composition of terpenes in resins of Arizona ponderosa pine with those of feed trees in Colorado indicates that Abert squirrels may have adapted to resinsof feed trees characteristic of their respective regions.
22 citations
TL;DR: In this paper, a tris(triphenylphosphine)rhodium carbonyl hydride RhHCO(PPh3)3 was performed on selected terpenes: terpinolene, S(−)limonene, α- and β-cedrenes, α-, β-caryophyllenes, α, and β caryophylla oxide.
Abstract: Hydroformylation in the presence of tris(triphenylphosphine)rhodium carbonyl hydride RhHCO(PPh3)3 was performed on selected terpenes: terpinolene, S(—)limonene, α- and β-cedrenes, α- and β-caryophyllenes and caryophyllene oxide. Except for terpinolene, in which only the trisubstituted endocyclic bond was hydroformylated. the double bonds affected were always exocyclic. These new fragrant compounds may be of use in perfumery.
TL;DR: In this article, the structures of five new monoterpenoid components of Urtica dioica were elucidated by spectrometry, and the mass spectra of the derivatives provided more information compared to those of the free compounds.
TL;DR: In this article, the essential oil of Festuca arundinacea was isolated by steam distillation of fresh grass with a yield of 0.005% (w/w).
Patent•
19 Dec 1991TL;DR: In this paper, the use in augmenting or enhancing the aroma or taste of a foodstuff of a reaction product of linalool with citric acid wherein the reaction is carried out at 100° C. in aqueous media for a period of from about two up to four hours.
Abstract: Described is the use in augmenting or enhancing the aroma or taste of a foodstuff of a reaction product of linalool with citric acid wherein the reaction is carried out at 100° C. in aqueous media for a period of from about two up to four hours. The resulting reaction product contains a novel mixture of terpenes.
TL;DR: In this article, three new terpenes have been isolated from Thapsia villosa var. minor [2n=22 (=2x] and, mainly by spectroscopic methods, shown to be monoesters of the novel sesquiterpene alcohol (4S,5S,7S,8S)-1(10)-guaiene-8,11-diol.
TL;DR: From Artemisia salsoloides, a sesquiterpene epoxide with a new carbon skeleton, salsolene oxide (1), was isolated from extended NMR studies.
TL;DR: The label from acetate was incorporated with the expected selectivity (as revealed by Kuhn-Roth degradation), but degradation of the mevalonate-labelled samples indicated some scrambling of label, presumably via acetate incorporation of degraded meval onate.
Abstract: 1.
1. Sodium [2-14C] acetate is utilized for de novo synthesis of the lipid cetyl palmitate (9) but not for de novo terpene synthesis in the alcyonacean soft coral A. molle. It was established by chemical degradation that >95% of the 14C label associated with the major terpene metabolite (4) appeared in the two butyrate ester functions with the remaining activity associated with an acetate ester substituent.
2.
2. In contrast, for Heteroxenia sp., de novo synthesis of the terpenes cubebol (5) and clavukerin A (6) from sodium [1-14C] acetate and from d,l-[2-14C] mevalonolactone was detected.
3.
3. The label from acetate was incorporated with the expected selectivity (as revealed by Kuhn-Roth degradation), but degradation of the mevalonate-labelled samples indicated some scrambling of label, presumably via acetate incorporation of degraded mevalonate.
Journal Article•
01 Jan 1991
TL;DR: In this paper, the authors reviewed the literature of a diverse collection of cyclohexane, cyclo-hexene, and cyclo hexadiene natural products from 1971 through mid-1991, and presented functionalized examples of products that contain amino acids and pseudosugars.
Abstract: Publisher Summary The chapter reviews the literature of a diverse collection of cyclohexane, cyclohexene, and cyclohexadiene natural products from 1971 through mid-1991. It discusses nonfunctionalized terpenes, unusual terpenoids, and nonterpenoids, each containing a of cyclohexane, cyclohexene or cyclohexadiene ring. Examples of nonfunctionalized terpenes, which include herbal plants that secrete one of these compounds, are illustrated. The chapter then presents functionalized examples of products that contain amino acids, oxygenated cyclohexanes, and oxygenated cyclohexenes. It also describes the structure of nonfunctionalized or unusual terpenoids. C13 Norterpenoids are discussed next, and are described as a group of compounds that play an important role as aroma components in fruits and plants. The structure of the shikimic acid pathway is described including its mechanistic aspects, its synthesis, analogues, and natural occurrence. The structure of cyclitols and their derivatives are also discussed. Similarly, inositols are explained in detail. Thereafter, the chapter explains pseudosugars, which are sugars in which the ring oxygen is replaced with a methylene group. Aminocyclitols that yield an array of novel antibiotics are explained. Benzoquinones and quinols that are remarkable in their medicinal qualities are addressed. Finally, halogenated tyrosine metabolites that are a collection of marine natural products are described.
TL;DR: In this paper, a three-step synthesis of enantiomeric cannabinoid terpene synthons from (+)- and/or (−)-nopinone is described.
Abstract: A three-step synthesis of important, enantiomeric cannabinoid terpene synthons, 1, from (+)- and/or (–)-nopinone is described.