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Bioavailability and pharmacokinetics of natural volatile terpenes in animals and humans.

Herbal medicinal products containing natural volatiles are used in the treatment of gastrointestinal diseases, pain, colds and bronchitis. Many pharmacological studies report a wide variety of in vitro effects, with anti-inflammatory and antimicrobial activities investigated most frequently. In comparison, relatively few studies on the bioavailability and pharmacokinetics have been carried out. Thus, the relevance of the in vitro activity to the therapeutic effects found in individual studies or documented in textbooks of phytotherapy is still not established. Further studies with essential oils and their single compounds providing supporting evidence of efficacy and demonstrating systemic availability are necessary. Such data could also be important in the context of safety.

Animals↗

Bioactive terpenes from the roots of Chloranthus henryi.

12,15-Epoxy-5alpha H,9beta H-labda-8(17),13-dien-19-oic acid (1) and 14-methoxy-15,16-dinor-5alpha H,9alpha H-labda-13(E),8(17)-dien-12-one (2), two new labdane-type diterpenes, and 1alpha-hydroxy-8,12-epoxyeudesma-4,7,11-triene-6,9-dione (3), one new eudesmane-type sesquiterpene, were isolated from Chloranthus henryi Hemsl, along with two known compounds, 8beta H-eudesma-4(14),7(11)-dien-12,8-olide (4) and 8beta-hydroxyeudesma-4(14),7(11)-dien-12,8-olide (5). Their structures were established by a combination of 1D- and 2D-NMR spectroscopic techniques. The new compounds 2, 3 and the known compound 4 exhibited antitumor activities against Hela and K562 human tumor cell lines.

Antineoplastic Agents, Phytogenic↗

Biosynthesis of terpenes: studies on 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate reductase.

Earlier in vivo studies showed the involvement of IspH protein in the conversion of 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate into isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP). We have demonstrated now that cell extract of an Escherichia coli strain engineered for hyperexpression of the ispH (lytB) gene catalyzes the in vitro conversion of 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate into IPP and DMAPP. The reaction requires NADH, FAD, divalent cations (preferably Co2+), and probably one or more as-yet-unidentified proteins. The low intrinsic catalytic activities of wild-type E. coli cell extract and isolated chromoplasts of red pepper (Capsicum annuum) are enhanced by the addition of purified recombinant IspH protein.

Amino Acid Sequence↗

Studies on the nonmevalonate pathway to terpenes: the role of the GcpE (IspG) protein.

Recombinant Escherichia coli cells engineered for the expression of the xylB gene in conjunction with genes of the nonmevalonate pathway were supplied with (13)C-labeled 1-deoxy-D-xylulose. Cell extracts were analyzed directly by NMR spectroscopy. (13)C-labeled 2C-methyl-D-erythritol 2,4-cyclodiphosphate was detected at high levels in cells expressing xylB, ispC, ispD, ispE, and ispF. The additional expression of the gcpE gene afforded 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate as an intermediate of the nonmevalonate pathway. Hypothetical mechanisms involving conserved cysteine residues are proposed for the enzymatic conversion of 2C-methyl-D-erythritol 2,4-cyclodiphosphate into 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate catalyzed by the GcpE protein.

Amino Acid Sequence↗

Systemic induction of the biosynthesis of terpenic compounds in Digitalis lanata.

A bacterial screening was carried out in the rhizosphere of two Digitalis species, D. thapsi and D. parviflora, both at the vegetative stage and at flowering. A total of 480 isolates were characterised at genus level, Bacillus being the dominant genera in all cases. Fifty percent of the Bacillus strains isolated from each species were analysed by PCR-RAPDs. At 85% similarity, 12 groups separated for D. thapsi and 18 for D. parviflora. One strain of each group was selected for biological assay on D. lanata, evaluating growth promotion and cardenolide content in leaves after inoculation performed in the root system. The plant parameters evaluated were leaf surface area, shoot and root dry weight and leaf number. Lanatoside C content was evaluated by HPLC. Only 17 strains caused significant increases in at least one of the parameters evaluated. The most striking result was that some strains promoted growth and increased cardenolide content at the same time. This effect was detected on leaves while inoculation was carried out on roots. Interestingly, these two parameters are not enhanced simultaneously under regular conditions in pot or in tissue cultures.

Bacillus↗

Effect of different terpene-containing essential oils on percutaneous absorption of trazodone hydrochloride through mouse epidermis.

The aim of our study was to investigate the enhancing effect of several essential oils in the percutaneous absorption of trazodone hydrochloride (TZN). For this purpose, fennel oil, eucalyptus oil, citronella oil, and mentha oil were applied on the skin membrane in three different ways: included in the transdermal device, as a pretreatment, or both. To investigate the effect of penetration enhancers used in this study on the percutaneous absorption of TZN through mouse epidermis, Keshary-Chien diffusion cells were employed. The receptor phase was constantly stirring saline phosphate buffer of pH 7.4 at 37 +/- 1 degrees C. Results showed that pretreatment of skin with essential oils increases the flux values of TZN compared with the values obtained when the same essential oils were included in the transdermal devices. The percutaneous penetration flux for TZN was increased with skin pretreatment by 10% essential oils in the following order: fennel oil > eucalyptus oil > citronella oil > mentha oil. The amount of TZN retained in the skin after pretreatment with essential oils was found to be very similar in all cases and much higher than in the experiments without skin pretreatment.

Administration, Cutaneous↗

Three 2-(2-phenylethyl) chromones and two terpenes from agarwood.

A new Chromone, 7,8-dimethoxy-2-[2-(3'-acetoxyphenyl)ethyl]chromone (1) was isolated from an acetone extract of the Cambodian agarwood along with two known chromones, 6-methoxy-2-(2-phenylethyl)chromone (2) and 6,7-dimethoxy-2-(2-phenylethyl)chromone (3). In addition, an abietane ester (4) and the sesquiterpene dehydrofukinone (5) were isolated from the agarwood oil of the same origin. Structural elucidation of all isolated compounds was made based on IR, 1H and 13C NMR spectroscopic data.

Chromones↗