SEX-PHEROMONE FOR THE BROWNBANDED COCKROACH IS AN UNUSUAL DIALKYL-SUBSTITUTED ALPHA-PYRONE

被引:35
作者
CHARLTON, RE
WEBSTER, FX
ZHANG, AJ
SCHAL, C
LIANG, DS
SRENG, I
ROELOFS, WL
机构
[1] CORNELL UNIV, NEW YORK STATE AGR EXPT STN, DEPT ENTOMOL, GENEVA, NY 14456 USA
[2] SYRACUSE UNIV, COLL ENVIRONM SCI & FORESTRY, SYRACUSE, NY 13210 USA
[3] RUTGERS UNIV, COOK COLL, DEPT ENTOMOL, NEW BRUNSWICK, NJ 08903 USA
[4] CNRS, MARSEILLE 09, FRANCE
关键词
SUPELLA-LONGIPALPA; ELECTROANTENNOGRAM; BEHAVIORAL RESPONSES;
D O I
10.1073/pnas.90.21.10202
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Female brownbanded cockroaches, Supella longipalpa, emit a sex pheromone that attracts males from a distance. This pheromone was isolated and identified as 5-(2,4-dimethylheptanyl)-3-methyl-2H-pyran-2-one (which we refer to as supellapyrone), and its structure was confirmed by synthesis. A racemic blend of the synthetic compound elicited behavioral and electrophysiological responses comparable to the natural pheromone across a range of doses. This compound is not only a very different type of cockroach pheromone but also makes up an additional class of natural products namely, 3,5-dialkyl-substituted alpha-pyrones.
引用
收藏
页码:10202 / 10205
页数:4
相关论文
共 34 条
[1]   HETEROCYCLIC PHOTOCHEMISTRY .1. PHOTOTRANSPOSITIONS IN HYDROXYPYRYLIUM CATIONS - PERMUTATION PATTERN-ANALYSIS AND MECHANISTIC STUDIES [J].
BARLTROP, JA ;
BARRETT, JC ;
CARDER, RW ;
DAY, AC ;
HARDING, JR ;
LONG, WE ;
SAMUEL, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (25) :7510-7521
[2]   PRACTICAL ASPECTS OF TWO-DIMENSIONAL TRANSVERSE NOE SPECTROSCOPY [J].
BAX, A ;
DAVIS, DG .
JOURNAL OF MAGNETIC RESONANCE, 1985, 63 (01) :207-213
[3]   MODERN PULSE METHODS IN HIGH-RESOLUTION NMR-SPECTROSCOPY [J].
BENN, R ;
GUNTHER, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1983, 22 (05) :350-380
[4]   A MICRO-PREPARATIVE GAS CHROMATOGRAPH AND A MODIFIED CARBON SKELETON DETERMINATOR [J].
BROWNLEE, RG ;
SILVERST.RM .
ANALYTICAL CHEMISTRY, 1968, 40 (13) :2077-&
[5]   INSECT VENOMS ATTRACTANTS AND REPELLENTS .11. MASSOILACTONE FROM 2 SPECIES OF FORMICINE ANTS AND SOME OBSERVATIONS ON CONSTITUENTS OF BARK OIL OF CRYPTOCARYA MASSOIA [J].
CAVILL, GWK ;
CLARK, DV ;
WHITFIELD, FB .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1968, 21 (11) :2819-+
[6]  
FRANCKE W, 1985, Z NATURFORSCH C, V40, P145
[7]   FEMALE CALLING AND REPRODUCTIVE-BEHAVIOR IN THE BROWN BANDED COCKROACH, SUPELLA-LONGIPALPA (F) (ORTHOPTERA, BLATTELLIDAE) [J].
HALES, RA ;
BREED, MD .
ANNALS OF THE ENTOMOLOGICAL SOCIETY OF AMERICA, 1983, 76 (02) :239-241
[8]   IDENTIFICATION AND SYNTHESIS OF PERIPLANON-A [J].
HAUPTMANN, H ;
MUHLBAUER, G ;
SASS, H .
TETRAHEDRON LETTERS, 1986, 27 (51) :6189-6192
[9]  
Heath R. R., 1984, Techniques in pheromone research, P287
[10]   A SIMPLE STEREOSELECTIVE VERSION OF CLAISEN REARRANGEMENT LEADING TO TRANS-TRISUBSTITUTED OLEFINIC BONDS . SYNTHESIS OF SQUALENE [J].
JOHNSON, WS ;
WERTHEMANN, L ;
BARTLETT, WR ;
BROCKSOM, TJ ;
LI, TT ;
FAULKNER, DJ ;
PETERSEN, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (03) :741-+