Novel Floral Scent Compounds from Night-Blooming Araceae Pollinated by Cyclocephaline Scarabs (Melolonthidae, Cyclocephalini)

J Chem Ecol. 2019 Feb;45(2):204-213. doi: 10.1007/s10886-018-1018-1. Epub 2018 Sep 19.

Abstract

Nocturnal flowering plants often release strong scents to attract their pollinators. Among night active flower visitors are cyclocephaline scarab beetles, which have been demonstrated to respond to uncommon volatile organic compounds released in high amounts by their host plants. In Araceae, the molecular structure of several such compounds is yet to be unveiled. We investigated headspace floral scent samples of Philodendron squamiferum, Thaumatophyllum mello-baretoanum, and Xanthosoma hylaeae by a variety of approaches, leading to the identification of novel compounds. Dehydrojasmone, (Z)-4-methylene-5-(pent-2-en-1-yl)cyclopent-2-en-1-one (1), (Z)-3-methylene-2-(pent-2-en-1-yl)cyclopentyl acetate (isojasmyl acetate, 3), and (E)-4,8-dimethylnona-1,3,7-trien-5-yl acetate (4) had not been previously reported, while full analytical data of the recently described (Z)-3-methylene-2-(pent-2-en-1-yl)cyclopentan-1-ol (isojasmol, 2) are presented here. All these compounds are derived from more common precursors, (Z)-jasmone and (E)-4,8-dimethyl-1,3,7-nonatriene, likely through biosynthetic "post-processing".

Keywords: Attractants; Beetle pollination; Floral scents; High resolution mass spectrometry; NMR spectroscopy; Preparative gas chromatography; Volatile organic compounds.

MeSH terms

  • Animals
  • Araceae / chemistry*
  • Araceae / metabolism
  • Coleoptera / physiology*
  • Cyclopentanes / chemistry
  • Flowers / chemistry
  • Flowers / metabolism
  • Gas Chromatography-Mass Spectrometry
  • Magnetic Resonance Spectroscopy
  • Oxylipins / chemistry
  • Pollination / drug effects
  • Volatile Organic Compounds / chemistry*
  • Volatile Organic Compounds / pharmacology

Substances

  • Cyclopentanes
  • Oxylipins
  • Volatile Organic Compounds
  • jasmone