NORSESQUITERPENES AS DEFENSIVE TOXINS OF WHIRLIGIG BEETLES (COLEOPTERA: GYRINIDAE)

被引:11
作者
Miller, James R. [1 ]
Hendry, Lawrence B.
Mumma, Ralph O.
机构
[1] Penn State Univ, Dept Entomol, University Pk, PA 16802 USA
关键词
biocommunication; defensive secretions; Gyrinidae; norsesquiterpenes; gyrinidal; isogyrinidal; gyrinidone; gyrinidione; steroid anesthesia;
D O I
10.1007/BF00987720
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
By use of a minnow bioassay, toxins wore detected in the pygidial secretions of the gyrinid beetles Dineutus assimilis (Kirby) and Dineutus nigrior Roberts. The active agents, which may be largely responsible for the relative immunity of the Gyrinidae from predation, wore isolated and identified as the norsesquiterpenes gyrinidione [(E)-1-mcthyl-2-formyl-3-(V-methylhex-Y-ene-2', 5'-dione)-cyclopentane], gyrinidone [(E, Z)-2-hydroxy-5,9-dimethyl-4-(but-1'-ene-3'-one)-3-oxobicyclo[4.3.0]-non-4-ene], gyrinidol [(E, E, E)-3,7-dimethyl-8,11-dioxo-2,6,9-dodecatrienal], and isogyrinidal [(E, E, Z)-3,7-dimethyl-8,11-dioxo-2,6,9-dodecatrienal]. Since gyrinidione and isogyrinidal are being reported for the first time, their physical and chemical properties are printed and biosynthetic relationships of the four norsesquiterpene structures are discussed. About 50% of the beetle defensive material was norsesquitorpenes, 25% polar lipids, and 20% could not be extracted from water into chloroform. As quantified by gas-liquid chromatography, D. asaimilia contained 245 +/- 73 mu g and D. nigrior 144+/- 64 mu g norsesquitorpenes per individual. The average relative composition of norsesquitorpenes in the pygidial secretions of both beetle species was constant: isogyrinidal, 6%; gyrinidone, 7%; gyrinidione, 36%; and gyrinidal, 48%. When administered externally in solution to fish, isolated norsesquitorpenes possessed narcotic and toxic activity similar to that of the anesthetic steroids deoxycorticosterone (DOC) and testosterone. Minnow dose-response curves demonstrated that gyrinidione and gyrinidal (LC100 := ca. 2 mu g/ml) were as toxic to fish as was DOC (LC100 = ca. 3 mu g/ml). Gyrinidone was less toxic (LC100 = ca. 15 mu g/ml) while isogyrinidal was relatively inactive (LC100 = ca. 90 mu g/ml).
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页码:59 / 82
页数:24
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