Isolation and Identification of Mosquito Bite Deterrent Terpenoids from Leaves of American (Callicarpa americana) and Japanese (Callicarpa japonica) Beautyberry

Essential oil extracts from Callicarpa americana and Callicarpa japonica were investigated. Bioassay-guided fractionation of C. americana extracts using the yellow fever mosquito, Aedes aegypti, led to the isolation of α-humulene, humulene epoxide II, and intermedeol and a newly isolated terpenoid (...

Full description

Saved in:
Bibliographic Details
Published in:Journal of agricultural and food chemistry 2005-07, Vol.53 (15), p.5948-5953
Main Authors: Cantrell, C. L, Klun, J. A, Bryson, C. T, Kobaisy, M, Duke, S. O
Format: Article
Language:English
Subjects:
Aedes aegypti
Animals
bioassays
Biological and medical sciences
bites and stings
Callicarpa
Callicarpa - chemistry
Callicarpa americana
Callicarpa japonica
callicarpenal
Culicidae
Food industries
Fundamental and applied biological sciences. Psychology
humulene
humulene epoxide II
Insect Bites and Stings - prevention & control
insect repellents
Insect Repellents - isolation & purification
insecticidal properties
intermedeol
leaves
Oils, Volatile - isolation & purification
pesticidal plants
plant extracts
Plant Leaves - chemistry
Terpenes - isolation & purification
terpenoids
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Essential oil extracts from Callicarpa americana and Callicarpa japonica were investigated. Bioassay-guided fractionation of C. americana extracts using the yellow fever mosquito, Aedes aegypti, led to the isolation of α-humulene, humulene epoxide II, and intermedeol and a newly isolated terpenoid (callicarpenal). Similar work involving C. japonica resulted in the isolation of an additional compound, spathulenol, as well as the four compounds isolated from C. americana. Structure elucidation was performed on all isolated compounds using a combination of gas chromatography−mass spectrometry−electron ionization, high-resolution liquid chromatography−MS−electrospray ionization, and one- and two-dimensional NMR experiments. Heretofore, 13,14,15,16-tetranorclerodane, callicarpenal, has never been identified from natural sources. Complete 1H and 13C NMR assignment data are provided for this compound. In bite deterrent studies, spathulenol, intermedeol, and callicarpenal showed significant repellent activity against A. aegypti and Anopheles stephensi. Keywords: Callicarpa; americana; japonica; Verbenaceae; spathulenol; intermedeol; α-humulene; callicarpenal; mosquito; repellent; deterrent; Aedes aegypti; Anopheles stephensi
ISSN:0021-8561
1520-5118
DOI:10.1021/jf0509308