Sexual deception of a beetle pollinator through floral mimicry.

Sexual mimicry is a complex multimodal strategy used by some plants to lure insects to flowers for pollination.1-4 It is notable for being highly species-specific and is typically mediated by volatiles belonging to a restricted set of chemical compound classes.3,4 Well-documented cases involve exploitation of bees and wasps (Hymenoptera)5,6 and flies (Diptera).7-9 Although beetles (Coleoptera) are the largest insect order and are well known as pollinators of both early and modern plants,10,11 it has been unclear whether they are sexually deceived by plants during flower visits.12,13 Here we report the discovery of an unambiguous case of sexual deception of a beetle: male longhorn beetles (Chorothyse hessei, Cerambycidae) pollinate the elaborate insectiform flowers of a rare southern African orchid (Disa forficaria), while exhibiting copulatory behavior including biting the antennae-like petals, curving the abdomen into the hairy lip cleft, and ejaculating sperm. The beetles are strongly attracted by (16S,9Z)-16-ethyl hexadec-9-enolide, a novel macrolide that we isolated from the floral scent. Structure-activity studies14,15 confirmed that chirality and other aspects of the structural geometry of the macrolide are critical for the attraction of the male beetles. These results demonstrate a new biological function for plant macrolides and confirm that beetles can be exploited through sexual deception to serve as pollinators.