Antifungal assay-guided isolation of the 95% ethanol extract of the stems of Colubrina retusa yielded jujubogenin 3-O-α-l-arabinofuranosyl(1→2)-[β-d-glucopyranosyl (1→3)]-α-l-arabinopyranoside (1), which showed modest growth-inhibitory effects against Candida albicans, Cryptococcus neoformans, and Aspergillus fumigatus (MICs, 50 μg/mL). In addition, two new minor saponins, jujubogenin 3-O-α-l-arabinofuranosyl(1→2)-[2-O-(trans,cis)p-coumaroyl-β-d-glucopyranosyl(1→3)]-α-l-arabinopyranoside (2), and jujubogenin 3-O-(5-O-malonyl)-α-l-arabinofuranosyl (1→2)-[β-d-glucopyranosyl(1→3)]-α-l-arabinopyranoside (3), were obtained. Saponin 2 was marginally active against only C. neoformans, with a MIC of 50 μg/mL, while 3 was inactive. NMR spectroscopy was used extensively for the structure determination of these compounds. The previously reported ambiguity of the NMR assignments of jujubogenin saponins for carbons -26 to -29 was clarified by a comprehensive analysis of the NMR spectra of 1.
After incubation of Δ9-tetrahydrocannabivarin with human hepatocytes, a major metabolic product was detected by gas chromatography—mass spectrometry that showed identical retention time and mass spectrum to the synthetic 11-nor-Δ9-tetrahydrocannabivarin-9-carboxylic acid (11-nor-Δ9-THCV-9-COOH). Analysis of human urine specimens from marijuana users and plasma samples from Marinol® users showed that 11-nor-Δ9-THCV-9-COOH was only present in urine specimens of marijuana users. These results supported the conclusion that identification of 11-nor-Δ9-THCV-9-COOH in a donor's urine specimen indicates the use or ingestion of cannabis-related product(s) and would not explain the sole use of Marinol.
The U.S. Congress has passed legislation requiring the U.S. Environmental Protection Agency (U.S. EPA) to develop, validate, and implement screening tests for identifying potential endocrine-disrupting chemicals within 3 years. To aid in the identification of methods suitable for this purpose, the U.S. EPA, the Chemical Manufacturers Association, and the World Wildlife Fund sponsored several workshops, including the present one, which dealt with wildlife species. This workshop was convened with 30 international scientists representing multiple disciplines in March 1997 in Kansas City, Missouri, USA. Participants at the meeting identified methods in terms of their ability to indicate (anti-) estrogenic/androgenic effects, particularly in the context of developmental and reproductive processes. Data derived from structure-activity relationship models and in vitro test systems, although useful in certain contexts, cannot at present replace in vivo tests as the sole basis for screening. A consensus was reached that existing mammalian test methods (e.g., with rats or mice) generally are suitable as screens for assessing potential (anti-) estrogenic/ androgenic effects in mammalian wildlife. However, due to factors such as among-class variation in receptor structure and endocrine function, it is uncertain if these mammalian assays would be of broad utility as screens for other classes of vertebrate wildlife. Existing full and partial life-cycle tests with some avian and fish species could successfully identify chemicals causing endocrine disruption; however, these long-term tests are not suitable for routine screening. However, a number of short-term tests with species from these two classes exist that could serve as effective screening tools for chemicals inducing (anti-) estrogenic/androgenic effects. Existing methods suitable for identifying chemicals with these mechanisms of action in reptiles and amphibians are limited, but in the future, tests with species from these classes may prove highly effective as screens. In the case of invertebrate species, too little is known at present about the biological role of estrogens and androgens in reproduction and development to recommend specific assays.
A new jujubogenin saponin was isolated from the stems of Colubrina retusa and identified as jujubogenin 3-O-α-l-arabinofuranosyl (1→2)-[3-O-(trans)-p-coumaroyl-β-d-glucopyranosyl (1→3)]-α-l-arabinopyranoside (4) on the basis of chemical and spectroscopic data. The antimycobacterial activity expressed as minimum inhibitory concentration (MIC) for compound 4 was 10 μg/mL.
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