RT journal article
T1 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
A1 Masi, Marco
A1 Tabanca, Nurhayat
A1 Cimmino, Alessio
A1 R. Green, Ivan
A1 R. Bloomquist, Jeffrey
A1 L. van Otterlo, Willem A.
A1 Evidente, Antonio
A1 Cala Peralta, Antonio
A1 Macías Domínguez, Francisco Antonio
A2 Química Orgánica
K1 Nerine sarniensis
K1 Amaryllidaceae
K1 mesembrine
K1 crinine
K1 crinsarnine
K1 sarniensinol
K1 bowdensine
K1 zika virus
K1 aedes aegypti
AB 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 (1S,2S,4aR,10bS)-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-(3aR,4Z,6S,7aS)-6-methoxy-1-methyl-2,3,3a,6,7,7a-hexa-hydro-1H-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 LD50 = 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 importantfor activity, while in crinine-type alkaloids, the substituent at C-2 seems to play a role in their activity.
PB Molecules
YR 2016
FD 2016-10
LK http://hdl.handle.net/10498/20324
UL http://hdl.handle.net/10498/20324
LA eng
DS Repositorio Institucional de la Universidad de Cádiz
RD 21-sep-2026