Oviposition stimulants for the pipevine swallowtail butterfly,Battus philenor (Papilionidae), from anAristolochia host plant: Synergism between inositols,aristolochic acids and a monogalactosyl diglyceride

Aristolochia macrophylla (Lam.) is a major host of the pipevine swallowtail butterfly,Battus philenor (L.), in the eastern United States. The female butterflies use a synergistic mixture of inositols, acids and a lipid as oviposition cues in recognizing this plant on contact. The acids and lipid, all isolated from the Et₂O-CHCl₃ fraction of an alcoholic extract of fresh foliage, were identified as aristolochic acid I (1), aristolochic acid II (2) and 1,2-[di(9Z,12Z,15Z)-octadeca-9, 12, 15-trienoyl]-3-galactosyl-sn-glycerol (3). Identifications were facilitated by UV, MS (EI and FAB) and NMR (1D and 2D) spectral techniques and by analysis of the hydrolysis products of 3. The active inositols were identified as D-(+)-pinitol, reported previously, and sequoyitol. Though this is apparently the first report of oviposition responses to a diacyl glycerol glycoside by a phytophagous insect, responses to aristolochic acids and sequoyitol have been reported previously for anAristolochia-feeding swallowtail of a different genus in Japan. This indicates substantial evolutionary conservatism in chemical oviposition cues within the tribe Troidini.     

Sequestration of aristolochic acids by the pipevine swallowtail, Battus philenor (L.): evidence and ecological implications

Summary. It has long been assumed that the North American pipevine swallowtail, Battus philenor (L.) (Papilionidae, Troidini), is protected from natural enemies by aristolochic acids sequestered from its Aristolochia food plants. This study confirmed that populations of B. philenor from Virginia and east Texas sequester these compounds. A comparison of the aristolochic acid profiles of the Virginia butterflies and their A. macrophylla food plants revealed several differences. The aristolochic acid fraction of the foliage was dominated by aristolochic acids I and II, whereas the insects had a much lower proportion of aristolochic acid II and contained, in addition, substantial amounts of aristolochic acids Ia and IVa, which were not detected in the plants. The eggs, larval integument, osmeterial glands, pupal cuticle, and adults (wings and bodies) all contained aristolochic acids. These findings help explain the abundant ecological data indicating that both immature and adult B. philenor are unpalatable and protected from natural enemies. Received 7 April 2000; accepted 31 May 2000