Microbiological transformations of terpenes: Part XXVI--Microbiological transformation of caryophyllene.
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Biotransformation↗
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[Contribution of a combination of alpha and beta benzopyrones, flavonoids and natural terpenes in the treatment of lymphedema of the lower limbs at the 2d stage of the surgical classification].
HYPOTHESIS: To create a phlebolymphologic therapy in order: to activate venous system; to activate lymphatic system; to activate macrophagic system; to reduce the proteic lymphatic load. EXPERIMENTAL: A study was performed on the use of an ideal phlebolymphological association (Tonka Beans, Gingko Biloba, Melilotus Officinalis) as a practical standpoint in the treatment of lymphedema of lower limbs in order to create an efficacious dose of Coumarin, Benzopyrones and Ginkolidi. CLINICAL: We investigated a population of 76 patients treated in an open-label study for six-eight months with a dosage of Coumarin 60 mg/daily + Gingko Biloba 40 mg/daily + Melilotus 40 mg/daily. CONCLUSION: This trilogy induced a very significant improvement in lymphedema (centimeter-aspect) both in functional symptoms (pain heaviness in affected limbs) and physical signs (edema, episodes of infection). Tolerance of long term treatment was good and the improvement was observed from the third month of treatment.
Adolescent↗
Foraging in chemically diverse environments: energy, protein, and alternative foods influence ingestion of plant secondary metabolites by lambs.
Interactions among nutrients and plant secondary metabolites (PSM) may influence how herbivores mix their diets and use food resources. We determined intake of a food containing a mix of terpenoids identified in sagebrush (Artemisia tridentata) when present in isoenergetic diets of increasing concentrations of protein (6, 9, 15, or 21% CP) or in isonitrogenous diets of increasing concentrations of energy (2.17, 2.55, 3.30, or 3.53 Mcal/kg). Lambs were offered choices between those diets with or without terpenes or between diets with terpenes and alfalfa hay. Intake of the diets with terpenes was lowest with the lowest concentrations of protein (6%) and energy (2.17 Mcal/kg) in the diets, and highest with diets of 15% CP and 3.53 Mcal/kg. In contrast, when terpenes were absent from the diets, lambs consumed similar amounts of all four diets with different concentrations of protein, and more of the diets with intermediate amounts of energy. When given a choice between the diet with or without terpenes, lambs preferred the diet without terpenes. When lambs were offered choices between terpene-containing diets and alfalfa, energy and protein concentrations influenced the amount of terpenes animals ingested. Energy densities higher than alfalfa, and protein concentrations higher than 6%, increased intake of the terpene-containing diet. Thus, the nutritional environment interacted with terpenes to influence preference such that lambs offered diets of higher energy or protein concentration ate more terpenes when forced, but not when offered alternative food without terpenes. The nutrients supplied by a plant and its neighbors likely influence how much PSM an animal can ingest, which in turn may affect the dynamics of plant communities, and the distribution of herbivores in a landscape. We discuss implications of these findings for traditional views of grazing refuges and varied diets in herbivores.
Animal Feed↗
Metabolic engineering of sesquiterpene metabolism in yeast.
Terpenes are structurally diverse compounds that are of interest because of their biological activities and industrial value. These compounds consist of chirally rich hydrocarbon backbones derived from terpene synthases, which are subsequently decorated with hydroxyl substituents catalyzed by terpene hydroxylases. Availability of these compounds is, however, limited by intractable synthetic means and because they are produced in low amounts and as complex mixtures by natural sources. We engineered yeast for sesquiterpene accumulation by introducing genetic modifications that enable the yeast to accumulate high levels of the key intermediate farnesyl diphosphate (FPP). Co-expression of terpene synthase genes diverted the enlarged FPP pool to greater than 80 mg/L of sesquiterpene. Efficient coupling of terpene production with hydroxylation was also demonstrated by coordinate expression of terpene hydroxylase activity, yielding 50 mg/L each of hydrocarbon and hydroxylated products. These yeast now provide a convenient format for investigating catalytic coupling between terpene synthases and hydroxylases, as well as a platform for the industrial production of high value, single-entity and stereochemically unique terpenes.
Alkyl and Aryl Transferases↗
Transdermal delivery from eutectic systems: enhanced permeation of a model drug, ibuprofen.
The formation of eutectic systems between ibuprofen (ibu) and seven terpene skin penetration enhancers was studied and, by using the eutectic systems as donors, the effects of melting point depression of the delivery system on transdermal delivery were investigated. A range of ibu:terpene binary mixtures were melted together, cooled, and recrystallised. Composition/melting point phase diagrams were determined by DSC and FT-IR analysis was used to investigated the nature of the interaction. Permeation of ibu across human epidermal membrane from the eutectic system was measured and compared to the flux from a saturated aqueous solution across skin and skin pretreated with the terpenes. The eutectic, i.e. minimum, melting points of these systems ranged from 32 degrees C for ibu:thymol 40:60 (% w/w) to -13 degrees C for ibu:1,8-cineole 40:60 (% w/w) compared to 76 degrees C for ibu alone. FT-IR studies indicated that only the terpenes which formed hydrogen bonds with ibu produced eutectic systems. Each set of ibu:terpene eutectic systems produced a significant (t-test, p = 0.05) increase in flux compared to a saturated aqueous solution applied to untreated and to terpene pretreated skin. For example, ibu:thymol 40:60 (% w/w) produced a flux of 150 micrograms/cm2/h, 5.9 times the flux from a saturated aqueous solution with thymol pretreated skin and 12.7 times the flux from a saturated aqueous solution across non-pretreated skin. In conclusion, a hydrogen bonding interaction is the primary mechanism by which some terpenes form binary eutectic mixtures with ibu. The resultant melting point depression of the delivery system is correlated with a significant increase in transdermal permeation.
Administration, Cutaneous↗
Evaluation of skin damage of cyclic monoterpenes, percutaneous absorption enhancers, by using culture human skin cells.
The cytotoxicity of monoterpenes, percutaneous absorption enhancers, to cultured human skin cells was investigated in order to quantitatively estimate their skin damage. A neutral red bioassay with epidermal keratinocytes and a contraction test of collagen gel in which dermal fibroblasts were cultured were employed for evaluating the cytotoxicity of terpenes. In the neutral red bioassay, keratinocyte proliferation was inhibited on the addition of terpenes, and cell survival remarkably decreased with an increase in the concentration of terpenes fed into the culture well. When the fibroblasts were cultured in a collagen gel matrix, the lattice of collagen contracted as the cells grew. Therefore, the application of cytotoxic agents brings about an inhibition of collagen gel contraction induced by the fibroblasts. Strong inhibition was observed in the cases of hydrocarbons in terpenes, and the inhibition was dependent on the concentration of these compounds added in the culture medium. The cytotoxicity of terpenes was compared with the skin damage evoked by the application of terpenes in rats in vivo. As a result, it was considered that the skin irritation caused by terpenes was predictable to a certain extent by means of the cytotoxic study of cultured human skin cells.
Animals↗
Volatile monoterpenes in black currant (Ribes nigrum L.) juice: effects of heating and enzymatic treatment by beta-glucosidase.
Changes of terpenes in black currant juice induced by the action of heat were investigated in the present study. Limonene, alpha-terpinene, linalool, alpha-terpineol, 4-terpineol, and menthol added to either black currant juice or a model system were thermally treated at 90 degrees C for 30 min. Similar heat-induced decreases in the concentration of the terpenes were observed in the two systems. The concentration of a range of terpene hydrocarbons and oxygenated terpenes increased, alpha-terpineol being a main conversion product of most of the examined compounds. In the main, the measured loss of compounds exceeded the detected concentrations of products formed. In addition, determination of glycosidically bound terpenes in the juice was carried out by two methods of enzymatic hydrolysis, namely, addition of beta-glucosidase to an Amberlite XAD-2 isolate or directly to black currant juice. The two methods gave the same patterns of seven released volatile aglyconic terpenes. However, none of the released terpenes are important for the odor of black currant juice.
Beverages↗
Production of ginkgolides and bilobalide by Ginkgo biloba plants and tissue cultures.
The accumulation of the terpenes ginkgolides and bilobalide in Ginkgo biloba was reported in plants as well as in plant cell cultures. Several hundred plants cultivated under controlled conditions in the field have been analyzed for their terpene production over many years. Cross-pollination experiments were performed with mature trees and the terpene content of the progeny was analyzed. The age of the tree is the main factor influencing the terpene content of the leaves as the level always decreases dramatically between young and old trees. 80 cell culture strains have been established and ginkgolides analyzed by GC/MS. These cell cultures reveal very low amounts of terpenes (1 microgram g-1 D.W. or less). On the contrary, isolated in vitro root cultures accumulate terpenes at the same concentration as the young plant leaves (4 mg g-1 D.W.). Attempts to obtain rapid growing roots or even hairy-roots did not succeed but the possibility to transform Ginkgo cell strains has been demonstrated.
Gas Chromatography-Mass Spectrometry↗
Effect of formulation variables on the percutaneous permeation of ketoprofen from gel formulations.
The objectives of our study were to evaluate the effect of four terpene enhancers, enhancer lipophilicity, and ethanol concentration using hydroxypropyl cellulose (HPC) and two Pluronic F-127 (PF-127) gel formulations on the percutaneous permeation of ketoprofen. All experiments were conducted using hairless mouse skin in vitro. Data recorded over 24 hr was compared with that for control gels (containing no terpene) using Franz diffusion cells. In the three gel formulations, the highest increase in the ketoprofen permeation was observed using limonene followed by nerolidol, fenchone, and thymol. Relationships were established between terpene lipophilicity, enhancement ratios for ketoprofen flux (ERflux), and the cumulative amount of ketoprofen after 24 hr (Q24) from the three gel formulations. However, no correlation was established between terpene lipophilicity and ketoprofen skin content values at 24 hr. Ethanol had a synergistic effect on the enhancing activity of the terpenes. Increasing the concentration of ethanol from 10% to 50% was associated with an increase in the permeation of ketoprofen. For example, use of PF-127 gel control (no terpene was included) containing 10% ethanol resulted in a ketoprofen flux of 19 +/- 2 microg/cm2 h and 481 +/- 131 microg/cm2 for Q24. Furthermore, for PF-127 containing 33% ethanol the flux was 34 +/- 3 microg/cm2 h and Q24 was 1,420 +/- 111 microg/cm2. However, HPC gel control that contained 50% ethanol resulted in a ketoprofen flux of 67 +/- 6 microg/cm2 h and 2,839 +/- 222 microg/cm2 for Q24.
Administration, Cutaneous↗
[Quantitative genetic analysis and multiple trait selection of pharmaceutical composition on Ginkgo biloba L. leaves].
The China possesses more than 70% Ginkgo resources in the world. The purposes of this research are to collect fine seedling and grafting clones in China, to probe genetic law on flavone glycosides and terpenes on Ginkgo leaves, and select leaf-used cultivars of high-pharmaceutical composition. In this research, we have collected 87 clones from 13 provenances and have carried out randomized block experiment at Tancheng, Laizhou and Yaoxiang in Shandong Province. Flavone glycosides and terpenes were determined through HPLC method from an improved Van Beek (1991) techniques and Shimadzu Lc-10 AD (Japan). Data and breeding analyses were carried out through IBMPC and SPQG30 software. The results of variance analyses show that there are significant differences to flavone glycosides, terpenes in clones, and the law of genetic parameters on heritability (h2) and genetic variability coefficient (Gcv), is clone > sex > provenance to flavone glycosides in ginkgo leaves. The sigma g2, h2, Gcv and delta G' in male tree clone leaves are higher than female clone leaves on flavone glycosides. We have found that there is a maximum flavone content clone among males and a maximum terpene clone among females. The results of Q-cluster analyses are consistent with R-factor analyses of twenty higher terpenes clones. The results of index selection show that the ri.Y2, E(I) and CGS' of multiple traits selection including (gamma) trait are higher than single trait and multiple traits selection excluding gamma. The direct or index selection is more suited to leaf-used cultivars of Ginkgo. The genetic stability of each clone was appraised by Wricke's ecovalence method and Nassar & Huhu noparameter method. Flavone glycosides and terpenes are more than 2.09%-2.57% and 0.33%-0.41%, respectively, and we have selected four clones.
Breeding↗
Different sources of reduced carbon contribute to form three classes of terpenoid emitted by Quercus ilex L. leaves.
Quercus ilex L. leaves emit terpenes but do not have specialized structures for terpene storage. We exploited this unique feature to investigate terpene biosynthesis in intact leaves of Q. ilex. Light induction allowed us to distinguish three classes of terpenes: (i) a rapidly induced class including alpha-pinene; (ii) a more slowly induced class, including cis-beta-ocimene; and (iii) the most slowly induced class, including 3-methyl-3-buten-1-ol. Using 13C, we found that alpha-pinene and cis-beta-ocimene were labeled quickly and almost completely while there was a delay before label appeared in linalool and 3-methyl-3-buten-1-ol. The acetyl group of 3-methyl-3-buten-1-yl acetate was labeled quickly but label was limited to 20% of the moiety. It is suggested that the ocimene class of monoterpenes is made from one or more terpenes of the alpha-pinene class and that both classes are made entirely from reduced carbon pools inside the chloroplasts. Linalool and 3-methyl-3-buten-1-ol are made from a different pool of reduced carbon, possibly in nonphotosynthetic plastids. The acetyl group of the 3-methyl-3-buten-1-yl acetate is derived mostly from carbon that does not participate in photosynthetic reactions. Low humidity and prolonged exposure to light favored ocimenes emission and induced linalool emission. This may indicate conversion between terpene classes.
Journal Article↗
Terpenoid secondary metabolism in Arabidopsis thaliana: cDNA cloning, characterization, and functional expression of a myrcene/(E)-beta-ocimene synthase.
The Arabidopsis genome project has recently reported sequences with similarity to members of the terpene synthase (TPS) gene family of higher plants. Surprisingly, several Arabidopsis terpene synthase-like sequences (AtTPS) share the most identity with TPS genes that participate in secondary metabolism in terpenoid-accumulating plant species. Expression of a putative Arabidopsis terpene synthase gene, designated AtTPS03, was demonstrated by amplification of a 392-bp cDNA fragment using primers designed to conserved regions of plant terpene synthases. Using the AtTPS03 fragment as a hybridization probe, a second AtTPS cDNA, designated AtTPS10, was isolated from a jasmonate-induced cDNA library. The partial AtTPS10 cDNA clone contained an open reading frame of 1665 bp encoding a protein of 555 amino acids. Functional expression of AtTPS10 in Escherichia coli yielded an active monoterpene synthase enzyme, which converted geranyl diphosphate (C(10)) into the acyclic monoterpenes beta-myrcene and (E)-beta-ocimene and small amounts of cyclic monoterpenes. Based on sequence relatedness, AtTPS10 was classified as a member of the TPSb subfamily of angiosperm monoterpene synthases. Sequence comparison of AtTPS10 with previously cloned monoterpene synthases suggests independent events of functional specialization of terpene synthases during the evolution of terpenoid secondary metabolism in gymnosperms and angiosperms. Functional characterization of the AtTPS10 gene was prompted by the availability of Arabidopsis genome sequences. Although Arabidoposis has not been reported to form terpenoid secondary metabolites, the unexpected expression of TPS genes belonging to the TPSb subfamily in this species strongly suggests that terpenoid secondary metabolism is active in the model system Arabidopsis.
Acyclic Monoterpenes↗
Ozone removal in the sampling of parts per billion levels of terpenoid compounds: an evaluation of different scrubber materials.
Some reactive volatile organic compounds (VOCs) are prone to degradation during sampling in an ozone-rich environment. A wide variety of different chemicals have been used to remove the ozone prior to sampling, but the possibility of interference by such chemicals with the sampled VOCs has not been thoroughly examined. In the present investigation, the retention/degradation of four terpenes (alpha-pinene, beta-pinene, 3-carene, and limonene) and isoprene together with some of their oxidation products (alpha-pinene oxide, nopinone, 4-acetyl-1-methylcyclohexene (AMCH), methylglyoxal, and methacrolein) has been studied, using various ozone-removing chemicals in an attempt to evaluate their potential as ozone scrubbers in the sampling of ambient air. The chemicals included in this first screening and their ozone-removing capacity are as follows: KI, MnO2, and Na2SO3 removed ozone for more than 24 h when exposed to 73-78 ppb (150-160 microg/m3) at a sampling flow rate of 500 mL/min. Silanized poly(1,4-phenylene sulfide) (PFS) removed ozone for 5 h, unsilanized PFS removed ozone for 1 h and 50 min, and Na2S2O3 removed ozone for 20 min. The recovery of the selected compounds with the different scrubbers was >95% for all compounds for KI; >95% for the terpenes oxidation products; >90% for the terpenes and isoprene for PFS; >90% for the terpenes and isoprene for MnO2 on copper nets, Na2SO3, and Na2S2O3; and <90% for the terpenes and isoprene for carulite (a commercial mixture between MnO2, CuO, and Al2O3), CuO, and indigo carmine.
Air Pollutants↗
Efficient extraction of ginkgolides and bilobalide from Ginkgo biloba leaves.
An efficient and rapid protocol has been developed for extracting ginkgolides and bilobalide (terpene trilactones) from Ginkgo biloba leaves. The procedure takes advantage of the extraordinary stability of the terpene trilactone structure to a variety of chemical treatments, especially oxidation, despite the presence of multiple oxygen functions. The protocol involves boiling the aqueous extract of leaves with dilute hydrogen peroxide, extraction with ethyl acetate, washing with basic solutions, and charcoal filtration to yield an off-white powder, terpene trilactone content 60-70%. It is likely that the hydrogen peroxide treatment degrades the undesired leaf constituents that lead to intense emulsification during extractions. Further reversed-phase chromatography of the extracts with polymeric resins removes the undesirable ginkgolic acids to amounts less than 10 ppm. The extracts are suited for pure terpene trilactone preparation, enrichment of terpene trilactone content in nutraceuticals, and preparations of low-flavonoid/high-terpene trilactone controls in medicinal studies. The four ginkgolides (ginkgolides A, B, C, J) and bilobalide isolated from the extract were identical in all respects with authentic specimens.
Chromatography, High Pressure Liquid↗
The pharmacokinetics of the bronchosecretolytic ozothin after intravenous injection.
Blood concentrations of the terpenes myrtenal, myrtenol, pionocarveol, verbenon and terbinhydrate in ozothin were investigated as a function of time after intravenous injection of 10 ml ozothin in 36 subjects. On each occasion 10 ml of the terpene mixture was injected into the inside right elbow. During the first 60 minutes after injection several 7 ml samples of citrate blood were withdrawn from the inside left elbow, immediately spun down and analysed by gas chromatography. Elimination of the terpenes from the blood during the first 10 minutes after injection appeared to follow a half-life time of three to four minutes with a second half-life time of 60 to 65 minutes. The concentration of these terpenes in expired air was determined in 27 subjects. Approximately 7% of the substances were eliminated via the lungs during the first 60 minutes. In a further series of experiments the concentration in subcutaneous fat during the first 24 hours after injection was studied. The whole terpenes concentrations range from 2.4 ng terpenes/g fat tissue to 0.8 ng terpenes/g fat at 24 hours.
Adipose Tissue↗
Capillary-HPLC-ESI-MS/MS method for the determination of acidic products from the oxidation of monoterpenes in atmospheric aerosol samples.
A method is presented for the determination of acidic products from terpene oxidation in filter samples of the atmospheric particle phase. Oxidation products of monoterpenes are believed to add a large fraction to the secondary organic aerosol (SOA) in the troposphere. Those products with structures containing one or more carboxylic acid groups have especially low vapour pressures and therefore they are believed to contribute substantially to the particle phase. Although many experiments were performed in simulation chambers to study the SOA generation by oxidation of terpenes, concentration measurements of products in the atmospheric particle phase are still rare. This is especially true for oxidation products of terpenes other than alpha- and beta-pinene. Therefore, we developed a method for the quantification of acidic products from terpene oxidation in atmospheric aerosol samples. After passing a PM 2.5 (PM = particulate matter) pre-separator to remove coarse particles, fine atmospheric particles were collected onto quartz fibre filters. A backup filter was placed behind the first filter to estimate possible sampling artifacts. The filters were extracted in an ultrasonic bath using methanol. After enrichment and re-dissolving in water the samples were analysed using a capillary-HPLC-ESI(-)-MS(n) set-up. The ion trap mass spectrometer could be used to gain structural information about the analytes and to enhance the selectivity of the measurements by using its MS/MS capability. A variety of products from different terpenes could be identified and quantified in samples of the ambient atmosphere using reference data from chamber experiments. Due to strong matrix effects quantification of samples from the real atmosphere had to be done by the standard addition method.
Journal Article↗
Monoterpenes as novel substrates for oxidation and halo-hydroxylation with chloroperoxidase from Caldariomyces fumago.
Chloroperoxidase (CPO) from Caldariomyces fumago was analysed for its ability to oxidize ten different monoterpenes with hydrogen peroxide as oxidant. In the absence of halide ions geraniol and, to a lesser extent, citronellol and nerol were converted into the corresponding aldehydes, whereas terpene hydrocarbons did not serve as substrates under these conditions. In the presence of chloride, bromide and iodide ions, every terpene tested was converted into one or more products. (1S)-(+)-3-carene was chosen as a model substrate for the CPO-catalysed conversion of terpenes in the presence of sodium halides. With chloride, bromide and iodide, the reaction products were the respective (1S,3R,4R,6R)-4-halo-3,7,7-trimethyl-bicyclo[4.1.0]-heptane-3-ols, as identified by 1H and 13C nuclear magnetic resonance. These product formations turned out to be strictly regio- and stereoselective and proceeded very rapidly and almost quantitatively. Initial specific activities of halohydrin formation increased from 4.22 U mg-1 with chloride to 12.22 U mg-1 with bromide and 37.11 U mg-1 with iodide as the respective halide ion. These results represent the first examples of the application of CPO as a highly efficient biocatalyst for monoterpene functionalization. This is a promising strategy for 'green' terpene chemistry overcoming drawbacks usually associated with cofactor-dependent oxygenases, whole-cell biocatalysts and conventional chemical methods used for terpene conversions.
Ascomycota↗
Effect of L-menthol and 1,8-cineole on phase behavior and molecular organization of SC lipids and skin permeation of zidovudine.
The aim of this investigation was to study the effect of 1,8-cineole and L-menthol on phase behavior and molecular organization of Stratum corneum (SC) lipids and permeation of zidovudine (AZT) across human cadaver skin (HCS). Permeation studies were conducted across HCS using Franz diffusion cells at 37 degrees C. Differential scanning calorimetry (DSC) and attenuated total reflectance Fourier transform infrared spectroscopy (ATR-FTIR) were employed to understand the effect of terpenes on phase behavior and molecular organization of a model SC lipid system consisting of an equimolar mixture of ceramide, palmitic acid and cholesterol. Both 1,8-cineole and L-menthol applied at 5% w/v in 66.6% ethanol as a vehicle significantly enhanced the pseudosteady state flux of AZT across HCS. The vehicle reduced the number of endothermic transitions observed in the DSC thermogram of a hydrated model SC lipid system from three to two with a lowered midtransition temperature (Tm), while the inclusion of terpenes resulted in a single but very broad endothermic transition for the model SC lipid system. Correspondingly, ATR-FTIR studies revealed that both 1,8-cineole and L-menthol increased CH2 stretching frequencies on either side of lipid transition in addition to lowering the Tm of model SC lipid system by approximately 2-8 degrees C. The alterations observed in the amide-I frequencies of model SC lipid system after the inclusion of terpenes suggest that they disrupt the interlamellar hydrogen-bonding network at the polar head group region. Further, terpenes also increased the hydration levels of the lipid system probably by forming new aqueous channels. These results indicate that terpenes enhance transdermal permeation of AZT and other drugs by transforming SC lipids from a highly ordered orthorhombic perpendicular subcellular packing to a less ordered hexagonal subcell packing.
Animals↗