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 studies^14,15 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.