Elucidation of the Structure of Solanoeclepin A, a Natural Hatching Factor of Potato and Tomato Cyst Nematodes, by Single-crystal X-ray Diffraction

Potato crops can be severely damaged by potato cyst nematodes Globodera rostochiensis and Globodera pallida, nematodes highly specific to potatoes and some other Solanaceae. Hatching of juveniles is controlled by agents excreted by the roots of some Solanaceae species. Over seventy years much effort has been expended by many groups to isolate these agents and to determine their structures. However, all attempts have failed. We report here the structure determination of a hatching factor excreted from potato and tomato roots. The hatching factor bears some resemblance to Glycinoeclepins as found by Masamune et al.2-5 and is hence designated as Solanoeclepin A.1 C27H30O9.3H2O, Mr = 498.5, monoclinic, P21, a = 11.289(2), b = 20.644(4), c = 11.632(12) Å, β = 90.81(4), V = 2711(3) Å3, Z = 4, Dx = 1.35 g cm–3, λ(Cu-K&alpha ) = 1.5418 Å, μ(Cu-Kα ) = 9.0 cm–1, F(000) = 1176, –60 °C. Final R = 0.117 for 3721 observed reflections