An Alkanna orientalis leaf and flower extract inhibited the growth of Staphylococcus aureus, a pathogen that causes an estimated 478,000 hospitalizations in the US annually. Bioassay-guided fractionation of A. orientalis resulted in isolation of the flavonoid sarothrin (5,7,4′-trihydroxy-3,6,8-trimethoxyflavone), which inhibited the growth of Mycobacterium smegmatis (MIC 75 μM) and S. aureus (MIC >800 μM), and possessed efflux pump inhibitory activity. This is the first report of antimicrobial or efflux pump inhibitory activity of sarothrin, and of its presence in A. orientalis. Our findings suggest that the effectiveness of A. orientalis extracts is due to a combination of multiple constituents, including sarothrin.
With this study, we explored the identity and chemistry of fungal endophytes from the roots of yerba mansa [Anemopsis californica (Nutt.) Hook. & Arn. (Saururaceae)], a botanical traditionally used to treat infection. We compared the diversity of fungal endophytes isolated from a wild-harvested A. californica population, and those from plants cultivated for one year in a greenhouse environment. The wild-harvested population yielded thirteen fungal strains (eleven unique genotypes). Of the extracts prepared from these fungi, four inhibited growth of Staphylococcus aureus by >25% at 20 µg/mL, and three inhibited growth of Pseudomonas aeruginosa by ≥20% at 200 µg/mL. By comparison, A. californica roots after one year of cultivation in the greenhouse produced only two unique genotypes, neither of which displayed significant antimicrobial activity. The fungus Chaetomium cupreum isolated from wild-harvested A. californica yielded a new antimicrobial spirolactone, chaetocuprum (1). An additional fourteen known compounds were identified using LC-MS dereplication of the various fungal endophytes. This study provides new insights into the identity and chemistry of A. californica fungal endophytes, and demonstrates the importance of considering growing conditions when pursuing natural product drug discovery from endophytic fungi.
Topical preparations of Anemopsis californica have been used by Native American tribes in the southwestern United States and northern Mexico to treat inflammation and infections. We report results of bioassay-guided isolation conducted on a sample of A. californica roots. The furofuran lignans sesamin (1) and asarinin (2) were isolated and shown to have MIC values ranging from 23 to 395 µM against five different species of environmental nontuberculous mycobacteria. These findings are significant given that these bacteria can cause skin, pulmonary, and lymphatic infections. Crude A. californica extracts were analyzed by liquid chromatography - mass spectrometry (LC-MS), and it was determined that sesamin and asarinin were extracted at relatively high levels from roots (1.7–3.1g/kg and 1.1–1.7 g/kg, respectively), but lower levels from leaves (0.13 g/kg for both compounds). Our findings suggest that the majority of activity of crude A. californica root extracts against nontuberculous mycobacteria can be attributed to the presence of sesamin and asarinin. This paper is the first to report isolation of these compounds from a member of the Saururaceae family, and the first to describe their activity against nontuberculous mycobacteria.
Gas chromatography mass spectrometry (GCMS) technology, whether in a laboratory or in the field allows scientists to identify and quantitate volatile and semi-volatile chemical compounds at low levels. It was not until the 1990s, well after the birth of GCMS in the 1950’s, that portable GCMS technology became possible. GCMS miniaturization along with a need for scientists to test samples outside of the laboratory drove the development of portable GCMS systems. Currently, scientists in the environmental, emergency response, government, military sectors, and private manufacturing industries use portable GCMS technology to monitor and quantitate various chemicals such as low levels of hazardous compound exposure in the environment. Successful implementation of portable GCMS also required that many sample preparatory techniques used in the laboratory must be modified for application in the field to maintain simplicity and robustness of the analysis of complex matrices like soil or water. This chapter will describe portable GCMS technology along with the current uses and sample preparatory techniques utilized.
SUMMARY WS-3 (N-ethyl-p-menthane-3-carboxamide) is a compound used as a cooling agent for tobacco or nicotine products. Three other similar compounds WS-23 (N,2,3-trimethyl-2-propan-2-ylbutanamide), Evercool 180 (N-p-benzene-acetonitrile menthanecarboxamide), and Evercool 190 (N-(2-pyridine-2-yl)ethyl-3-p-menthancarboxamide) also have cooling properties and can be used as tobacco additives. A few previously reported methods for WS-3 analysis were rather complex, and the goal of present work was to develop a simple, rapid, and accurate procedure for simultaneous analysis of WS-3 and of the other three cooling compounds. For this purpose, a LC/MS procedure has been developed that requires 6-min runs. The method was calibrated to analyze solutions containing each analyte in the range of concentrations between 48.8 ng/mL to 12.5 µg/mL. The procedure is selective and shows excellent precision with typical RSD lower than 3%. In parallel to the LC/MS method, a GC/MS procedure was also developed mainly with the goal of having a proof of the accuracy for both methods. This GC separation requires 20-min runs. The GC/MS technique was calibrated to analyze solutions containing each analyte in the range of concentrations between 1.56 µg/mL to 125 µg/mL for WS-23 and WS-3, from 6.25 µg/mL to 125 µg/mL for Evercool 180, and from 3.13 µg/mL to 125 µg/mL for Evercool 190. The sensitivity of the LC/MS method is significantly higher than the GC/MS one, and for the analysis of traces of cooling agents the LC/MS method is recommended. The LC/MS method was applied for the analysis of WS-3 in tobacco, cigarette smoke, flavor solutions, and in nicotine pouches. No samples containing the other cooling agents were available. [Contrib. Tob. Nicotine Res. 32 (2023) 26–33]
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