From the fruits of Gardenia jasminoides several carotenoids were isolated and identified. Crocetin (1) was characterized by UV/vis, cochromatography, and LC-MS. The following glycosyl esters of crocetin (1) were identified:  crocin (crocetin di(β-gentiobiosyl) ester) (6) by UV/vis, 1H- and 13C-NMR, and FAB-MS and crocetin mono(β-gentiobiosyl) ester (4) by UV/vis, 1H-NMR, and LC-MS. There are strong indications for the presence of 13Z-crocin (9) (UV/vis, 1H-NMR, and LC-MS). From saffron (Crocus sativus L.), another glycosyl ester of crocetin (1) was isolated. It was identified as crocetin (β-gentiobiosyl) (β-neapolitanosyl) ester (7) by UV/vis, 1H-NMR, and MS. Keywords: Carotenoids; glycosyl esters; isolation; structure elucidation; Gardenia jasminoides; saffron; Crocus sativus

Background: Due to variable absorption and extensive first-pass metabolism, the bioavailability of oral delta-9-tetra­hydrocannabinol (THC) and cannabidiol (CBD) is low, and, therefore, alternative application forms are necessary. Methods: In an open-label, 2-period phase-1 study on 11 healthy volunteers, a combination of THC and CBD was compared by pulmonary (inh) and intravenous (iv) application. The liquid aerosol was produced by an in vitro validated pressurized metered-dose inhaler (pMDI) device, releasing 41–44% of the cannabinoid dose, enabling a dosage of 81 µg THC and 87 µg CBD per actuation. Three subjects (pilot trial, low-dose session) received 324 and 348 μg THC and CBD, respectively, and 8 subjects (main trial, high-dose session) received 648 and 696 µg THC and CBD, respectively. The addition of the local anesthetic lidocaine to the inh preparation should prevent airways irritation and coughing. The pharmacokinetic evaluation was based on plasma profiles acquired by gas chromatography-mass spectrometry. Adverse effects were monitored by visual analog scales and measuring vital functions. Results: After low inh doses, THC and CBD were not measurable in plasma longer than 20 and 40 min after administration, respectively. Therefore, only plasma levels resulting after high doses were further evaluated. After inh and iv administration, THC plasma peaks were observed 5 min post-drug, with THC peak concentrations ranging from 3 to 22 and from 13 to 40 ng/mL, respectively. CBD peaks were also measured 5 min after inh and iv administration, with concentrations ranging from 2 to 17 and from 14 to 26 ng/mL, respectively. The elimination half-lives were 7 and 11 min after inh and 22 and 24 min after iv administration for THC and CBD, respectively. The mean inh bioavailability (calculated vs. iv) was 55 ± 37 and 59 ± 47% for THC and CBD, respectively. Conjugated 11-carboxy-THC was the main THC metabolite. The nebulized aerosol was generally well tolerated with little or no coughing and only slight psychological adverse effects. These were more distinct after iv administration, especially irritations and hallucinations. Besides moderate tachycardia, the vital functions stayed unchanged. Conclusions: We conclude that a THC-CBD inh aerosol shows favorable pharmacokinetic properties, which are similar to those of an iv preparation. Adding a local anesthetic is recommended to prevent coughing, which decreases absorption. The negligible psychoactivity may be due to an anti­psychotic effect of CBD, the low THC dosage, and/or the decreased formation of the psychoactive metabolite 11- hydroxy-THC. Therefore, the inhalation via a pMDI is a viable, safe, and well-tolerated alternative to the oral administration.

Female sticklebacks (Gasterosteus aculeatus) use the red coloration of males as a criterion for mate choice. Redder males are more attractive. However, males often differ not only in the intensity of their coloration (from dull to bright red) but also in color quality (from yellowish to purple-red). We investigated whether the red coloration of the stickleback is actually a multiple signal made by several pigments. We kept wild caught males singly in tanks until they had built a nest and were ready to accept females. Then, we took standard photographs and measured their colors by spectrometer analyses of the slides and by descriptions of human observers. These two measurements were highly correlated. When analyzing the carotenoid content of the sticklebacks' skin we found two groups of carotenoids (astaxanthin and tunaxanthin/lutein) that were quantified for each individual. The differences in color observed in the fish are correlated to this pigment quantification. Redder fish have more astaxanthin in their skin than yellowish fish, while the color of the yellowish fish appears to be made by tunaxanthin/lutein. Our results suggest that the red coloration of sticklebacks is a multiple trait that is made of at least two different carotenoids. This opens the possibility that male sticklebacks signal more detailed information to females than a onedimensional trait would allow.

Since 2004, cannabis has been prohibited by the World Anti-Doping Agency for all sports competitions. In the years since then, about half of all positive doping cases in Switzerland have been related to cannabis consumption. In doping urine analysis, the target analyte is 11-nor-9-carboxy-Delta(9)-tetrahydrocannabinol (THC-COOH), the cutoff being 15 ng/mL. However, the wide urinary detection window of the long-term metabolite of Delta(9)-tetrahydrocannabinol (THC) does not allow a conclusion to be drawn regarding the time of consumption or the impact on the physical performance. The purpose of the present study on light cannabis smokers was to evaluate target analytes with shorter urinary excretion times. Twelve male volunteers smoked a cannabis cigarette standardized to 70 mg THC per cigarette. Plasma and urine were collected up to 8 h and 11 days, respectively. Total THC, 11-hydroxy-Delta(9)-tetrahydrocannabinol (THC-OH), and THC-COOH were determined after hydrolysis followed by solid-phase extraction and gas chromatography/mass spectrometry. The limits of quantitation were 0.1-1.0 ng/mL. Eight puffs delivered a mean THC dose of 45 mg. Plasma levels of total THC, THC-OH, and THC-COOH were measured in the ranges 0.2-59.1, 0.1-3.9, and 0.4-16.4 ng/mL, respectively. Peak concentrations were observed at 5, 5-20, and 20-180 min. Urine levels were measured in the ranges 0.1-1.3, 0.1-14.4, and 0.5-38.2 ng/mL, peaking at 2, 2, and 6-24 h, respectively. The times of the last detectable levels were 2-8, 6-96, and 48-120 h. Besides high to very high THC-COOH levels (245 +/- 1,111 ng/mL), THC (3 +/- 8 ng/mL) and THC-OH (51 +/- 246 ng/mL) were found in 65 and 98% of cannabis-positive athletes' urine samples, respectively. In conclusion, in addition to THC-COOH, the pharmacologically active THC and THC-OH should be used as target analytes for doping urine analysis. In the case of light cannabis use, this may allow the estimation of more recent consumption, probably influencing performance during competitions. However, it is not possible to discriminate the intention of cannabis use, i.e., for recreational or doping purposes. Additionally, pharmacokinetic data of female volunteers are needed to interpret cannabis-positive doping cases of female athletes.

No abstract

No abstract

No abstract