Journal of Chemical Ecology

, Volume 45, Issue 11–12, pp 926–933 | Cite as

An Oviposition Stimulant for a Magnoliaceae-Feeding Swallowtail Butterfly, Graphium doson, from its Primary Host Plant, Michelia compressa

  • Tadanobu Nakayama
  • Keiichi HondaEmail author


Chemical examination of plant constituents responsible for oviposition by a Magnoliaceae-feeding butterfly, Graphium doson, was conducted using its major host plant, Michelia compressa. A methanol extract prepared from young leaves of the plant elicited a strong oviposition response from females. The methanolic extract was then separated by solvent partition into three fractions: CHCl3, i-BuOH, and aqueous fractions. Active substance(s) resided in both i-BuOH- and water-soluble fractions. Bioassay-guided further fractionation of the water-soluble substances by means of various chromatographic techniques led to the isolation of an oviposition stimulant. The stimulant was identified as d-(+)-pinitol on the basis of 13C NMR spectra and physicochemical properties. d-(+)-Pinitol singly exhibited a moderate oviposition-stimulatory activity at a dose of 150 μg/cm2. This compound was present also in another host plant, Magnolia grandiflora, in a sufficient amount to induce oviposition behavior of G. doson females. Certain cyclitols including d-(+)-pinitol have been reported to be involved in stimulation of oviposition by some Aristolochiaceae- and Rutaceae-feeding papilionid butterflies. A possible pathway of phytochemical-mediated host shifts in the Papilionidae, in which certain cyclitols could enact important mediators, is discussed in relation to the evolution of cyclitol biosynthesis in plants.


d-(+)-Pinitol Host shift Papilionidae Aristolochiaceae Magnoliaceae Rutaceae 



We thank late Dr. M. Nakai and K. Gotoh for help with collecting G. doson females and kind supply of larval food plant.

Supplementary material

10886_2019_1115_MOESM1_ESM.pdf (327 kb)
ESM 1 (PDF 327 kb)


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Authors and Affiliations

  1. 1.Division of Environmental Sciences, Faculty of Integrated Arts and SciencesHiroshima UniversityHigashihiroshimaJapan
  2. 2.Drug Engineering divisionChugai Pharmaceutical Co., Ltd.TokyoJapan
  3. 3.Graduate School of Biosphere ScienceHiroshima UniversityHigashihiroshimaJapan
  4. 4.Saijo Ecology InstituteHigashihiroshimaJapan

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