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Molecules 2016, 21(11), 1432; doi:10.3390/molecules21111432

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

1
Department of Chemical Sciences, University of Naples “Federico II”, Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli, Italy
2
Allelopathy Group, Department of Organic Chemistry, School of Science, Institute of Biomolecules (INBIO), University of Cádiz, C/República Saharaui 7, 11510 Puerto Real, Cádiz, Spain
3
Department of Entomology and Nematology, Emerging Pathogens Institute, University of Florida, Gainesville, FL 32610, USA
4
U.S. Department of Agriculture-Agricultural Research Service, Subtropical Horticulture Research Station, 13601 Old Cutler Rd., Miami, FL 33158, USA
5
Department of Chemistry and Polymer Science, University of Stellenbosch, Private Bag X1, Matieland, 7602 Stellenbosch, South Africa
*
Author to whom correspondence should be addressed.
Academic Editor: Michael Wink
Received: 19 September 2016 / Revised: 17 October 2016 / Accepted: 19 October 2016 / Published: 27 October 2016
(This article belongs to the Special Issue Diversity of Alkaloids)
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Abstract

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 16 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 important for activity, while in crinine-type alkaloids, the substituent at C-2 seems to play a role in their activity. View Full-Text
Keywords: Nerine sarniensis; Amaryllidaceae; mesembrine; crinine; crinsarnine; sarniensinol; bowdensine; Zika virus; Aedes aegypti Nerine sarniensis; Amaryllidaceae; mesembrine; crinine; crinsarnine; sarniensinol; bowdensine; Zika virus; Aedes aegypti
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Masi, M.; Cala, A.; Tabanca, N.; Cimmino, A.; Green, I.R.; Bloomquist, J.R.; van Otterlo, W.A.L.; Macias, F.A.; Evidente, A. 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. Molecules 2016, 21, 1432.

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