title: 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.
abstract: Two new Amaryllidaceae alkaloids, belonging to the mesembrine- and crinine-types, named crinsarnine (1) and sarniensinol (2), were isolated from the dried bulbs ofNerine sarniensistogether 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. Compounds1-6were evaluated against the Orlando reference strain ofAedes aegypti. None of compounds showed mortality against 1st instarAe. aegyptilarvae at the concentrations tested. In adult topical bioassays, only1displayed adulticidal activity with an LD50= 2.29 ± 0.049 μg/mosquito. As regards the structure-activity relationship, the pretazettine and crinine scaffold in2and4and in1and3respectively, proved to be important for their activity, while the pyrrole[de]phenanthridine scaffold present in5and6was 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 thetrans-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.
authors: Department of Chemical Sciences, University of Naples "Federico II", Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli, Italy. marco.masi@unina.it.
authors: Marco
authors: M
authors: Masi
authors: Department of Chemical Sciences, University of Naples "Federico II", Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli, Italy. antonio.cala@uca.es.|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. antonio.cala@uca.es.
authors: Antonio
authors: A
authors: Cala
authors: Department of Entomology and Nematology, Emerging Pathogens Institute, University of Florida, Gainesville, FL 32610, USA. ntabanca@ufl.edu.|U.S. Department of Agriculture-Agricultural Research Service, Subtropical Horticulture Research Station, 13601 Old Cutler Rd., Miami, FL 33158, USA. ntabanca@ufl.edu.
authors: Nurhayat
authors: N
authors: Tabanca
authors: Department of Chemical Sciences, University of Naples "Federico II", Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli, Italy. alessio.cimmino@unina.it.
authors: Alessio
authors: A
authors: Cimmino
authors: Department of Chemistry and Polymer Science, University of Stellenbosch, Private Bag X1, Matieland, 7602 Stellenbosch, South Africa. irg@sun.ca.za.
authors: Ivan R
authors: IR
authors: Green
authors: Department of Entomology and Nematology, Emerging Pathogens Institute, University of Florida, Gainesville, FL 32610, USA. jbquist@epi.ufl.edu.
authors: Jeffrey R
authors: JR
authors: Bloomquist
authors: U.S. Department of Agriculture-Agricultural Research Service, Subtropical Horticulture Research Station, 13601 Old Cutler Rd., Miami, FL 33158, USA. wvo@sun.ca.za.
authors: Willem A L
authors: WA
authors: van Otterlo
authors: 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. famacias@uca.es.
authors: Francisco A
authors: FA
authors: Macias
authors: Department of Chemical Sciences, University of Naples "Federico II", Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli, Italy. evidente@unina.it.
authors: Antonio
authors: A
authors: Evidente
mesh_terms: D000330:Aedes; D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D007303:Insect Vectors; D007306:Insecticides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D019684:Magnoliopsida / Q000737:chemistry*; D000071244:Zika Virus
chemical_list: D000470:Alkaloids; D007306:Insecticides
keywords: Aedes aegypti; Amaryllidaceae; Nerine sarniensis; Zika virus; bowdensine; crinine; crinsarnine; mesembrine; sarniensinol