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Two new Amaryllidaceae alkaloids, belonging to the mesembrine- and crinine-types, named crinsarnine ( 1 ) and sarniensinol ( 2 ), were isolated from the dried bulbs of Nerine sarniensis together with bowdensine ( 3 ), sarniensine ( 4 ), hippadine ( 5 ) and 1- O -acetyl-lycorine ( 6 ). Crinsarnine ( 1 ) and sarniensinol ( 2 ) were characterized using spectroscopic and chiroptical methods as (1 S ,2 S ,4a R ,10b S )-2,7-dimethoxy-1,2,3,4,4a,6-hexahydro-5,11b-ethano[1,3]dioxolo-[4,5- j ]phenanthridin-1-yl acetate and (6-(3a R ,4 Z ,6 S ,7a S )-6-methoxy-1-methyl-2,3,3a,6,7,7a-hexa-hydro-1 H -indol-3a-yl)benzo[ d ][1,3]dioxol-5-yl)methanol, respectively. Furthermore, the complete spectroscopic characterization of bowdensine ( 3 ) is reported for the first time. Compounds 1 - 6 were evaluated against the Orlando reference strain of Aedes aegypti . None of compounds showed mortality against 1st instar Ae. aegypti larvae at the concentrations tested. In adult topical bioassays, only 1 displayed adulticidal activity with an LD 50 = 2.29 ± 0.049 μg/mosquito. As regards the structure-activity relationship, the pretazettine and crinine scaffold in 2 and 4 and in 1 and 3 respectively, proved to be important for their activity, while the pyrrole[ de ]phenanthridine scaffold present in 5 and 6 was important for their reactivity. Among the pretazettine group compounds, opening of the B ring or the presence of a B ring lactone as well as the trans -stereochemistry of the A/B ring junction, appears to be important for activity, while in crinine-type alkaloids, the substituent at C-2 seems to play a role in their activity.

molecules/molecules online/molecules annual

Alkaloids with Activity against the Zika Virus Vector Aedes aegypti (L.)—Crinsarnine and Sarniensinol, Two New Crinine and Mesembrine Type Alkaloids Isolated from the South African Plant Nerine sarniensis