title: Insect antifeedants, pterocarpans and pterocarpol, in heartwood of Pterocarpus macrocarpus Kruz.
abstract: The insect antifeedant activities of pterocarpans and a sesquiterpene alcohol from the dichloromethane extract of Pterocarpus macrocarpus Kruz. (Leguminosae) were evaluated against the common cutworm, Spodoptera litura F. (Noctuidae), and the subterranean termite, Reticulitermes speratus (Kolbe)(Rhinotermitidae). Three pterocarpans, (-)-homopterocarpin (1), (-)-pterocarpin (2), and (-)-hydroxyhomopterocarpin (3) and the sesquiterpene alcohol, (+)-pterocarpol (5), were isolated from the dichloromethane extract of the heartwood of P. macrocarpus under guidance by a biological assay. Among these natural products, the most active insect antifeedant against both S. litura and R. speratus was 1. On the other hand, sesquiterpene alcohol 5 showed less insect antifeedant activity than the other pterocarpans against both insect species. While its methylated derivative, (-)-methoxyhomopterocarpin (4), showed high biological activity, 3 showed less insect antifeedant activity in this study. Interestingly, racemic 1 did not show insect antifeedant activity against S. litura. However, all of the test pterocarpans and isoflavones showed antifeedant activity against the test termites. Additionally, since these compounds were major constituents of P. macrocarpus, these antifeedant phenolics may act as chemical defense factors in this tree. In Thailand, lumber made from this tree is used to make furniture and in building construction due to its resistance to termite attack.
authors.affiliation: Department of Agricultural Chemistry, Faculty of Agriculture, Kinki University, Nakamachi, Japan. masanori@nara.kindai.ac.jp
authors.forename: Masanori
authors.initials: M
authors.lastname: Morimoto
authors.forename: Hiromi
authors.initials: H
authors.lastname: Fukumoto
authors.forename: Masaru
authors.initials: M
authors.lastname: Hiratani
authors.forename: Warinthorn
authors.initials: W
authors.lastname: Chavasiri
authors.forename: Koichiro
authors.initials: K
authors.lastname: Komai
mesh_terms: D000438:Alcohols / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D001572:Benzofurans / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D001578:Benzopyrans / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D005247:Feeding Behavior / Q000187:drug effects; D020049:Isoptera / Q000187:drug effects; D008968:Molecular Conformation; D009036:Moths / Q000187:drug effects; D010572:Pest Control, Biological; D010936:Plant Extracts / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D036343:Pterocarpans / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D035721:Pterocarpus / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D013045:Species Specificity; D013237:Stereoisomerism; D014934:Wood
chemical_list: D000438:Alcohols; D001572:Benzofurans; D001578:Benzopyrans; D010936:Plant Extracts; D036343:Pterocarpans; D012717:Sesquiterpenes; C514760:homopterocarpin; C514761:pterocarpol