New insecticidal rocaglamide derivatives and related compounds from Aglaia oligophylla.
Organic-soluble extracts of the twigs of Aglaia oligophylla collected in Vietnam yielded four insecticidal cyclopentatetrahydrobenzofurans of the rocaglamide type including one new natural product (compound 4). Moreover, two cyclopentatetrahydrobenzopyran derivatives, belonging to the aglain and aglaforbesin types, respectively, were also isolated. The aglaforbesin derivative 6 proved likewise to be a new natural product. All isolated rocaglamide, aglain, and aglaforbesin derivatives have a characteristic methylenedioxy substituent linked to C-6 and C-7 or to C-7 and C-8, respectively. Structure elucidation of the new natural products and the determination of the absolute configuration of compound 1 by calculation of its CD spectrum with molecular dynamics simulation are described. All isolated rocaglamide derivatives exhibited strong insecticidal activity toward neonate larvae of the polyphageous pest insect Spodoptera littoralis when incorporated into an artificial diet, with LC(50) values varying between 2.15 and 6.52 ppm.
Dreyer
M
M
Institut für Pharmazeutische Biologie, Heinrich Heine Universität, Düsseldorf, Universitätsstrasse 1, Gebäude 26.23, D-40225 Düsseldorf, Germany.
Nugroho
B W
BW
Bohnenstengel
F I
FI
Ebel
R
R
Wray
V
V
Witte
L
L
Bringmann
G
G
Mühlbacher
J
J
Herold
M
M
Hung
P D
PD
Kiet
L C
LC
Proksch
P
P
D000818:Animals; D001572:Benzofurans / Q000737:chemistry / Q000302:isolation & purification*; D002942:Circular Dichroism; D007306:Insecticides / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry / Q000379:methods; D008958:Models, Molecular; D015394:Molecular Structure; D019685:Rosales / Q000737:chemistry*; D018411:Spodoptera; D013237:Stereoisomerism
D001572:Benzofurans; D007306:Insecticides; C107772:rocaglamide