{"title":"Does the orchid Luisia teres attract its male chafer pollinators (Scarabaeidae: Protaetia pryeri pryeri) by sexual deception?","authors":"Sadao Wakamura, Norio Arakaki, Daisuke Moriyama, Shoko Kanayama, Masahiro Oike, Anna Kimura, Saki Wajima, Hiroshi Ono, Hiroe Yasui","doi":"10.1007/s00049-019-00297-x","DOIUrl":null,"url":null,"abstract":"<p>The epiphytic orchid <i>Luisia teres</i> (Asparagales: Orchidaceae) releases floral scent that attracts males of the cupreous polished chafer <i>Protaetia pryeri pryeri</i> (Coleoptera: Scarabaeidae) for pollination. We analyzed this floral scent to identify the attractant(s). When various flower parts were extracted with diethyl ether and assayed, male chafers were attracted to the extract of petals but not to that of sepals or lips. The petal extracts were chromatographed on silica gel column and the activity was found in ether and methanol fractions. Gas chromatography/mass spectrometry (GC/MS) analyses and subsequent NMR analyses revealed that both active fractions contained 2,3-dihydroxypropyl isovalerate (2,3-DHPiV) as a major compound. Natural 2,3-DHPiV showed identical retention time to that of synthetic (<i>R</i>)-enantiomer in subsequent HPLC analyses using a chiral column, while (<i>S</i>)-enantiomer was not detected. The amount of this compound was ca. 5?μg/flower. In field tests performed in Okinawa, Japan, males of <i>P. pryeri pryeri</i> were observed to fly around and land on a cotton ball impregnated with synthetic (<i>R</i>)-2,3-DHPiV, but no male was attracted to the (<i>S</i>)-enantiomer or the racemic mixture. Thus, the chemical attractant released from the flower was identified to be (<i>R</i>)-2,3-DHPiV. 2,3-DHPiV was also found in a volatile sample collected from the virgin females by GC/MS analyses using achiral column, while this compound did not occur in males. Because of the difficulty in HPLC detection of a small amount of 2,3-DHPiV, the chirality remains to be determined. Nevertheless, these results strongly suggest that the flowers of <i>L. teres</i> release the same compound as females of its pollinator <i>P. pryeri pryeri,</i> indicating that the flower of this orchid chemically mimics the female sex pheromone.</p>","PeriodicalId":515,"journal":{"name":"Chemoecology","volume":"30 2","pages":"49 - 57"},"PeriodicalIF":1.6000,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/s00049-019-00297-x","citationCount":"10","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemoecology","FirstCategoryId":"93","ListUrlMain":"https://link.springer.com/article/10.1007/s00049-019-00297-x","RegionNum":3,"RegionCategory":"环境科学与生态学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
引用次数: 10
Abstract
The epiphytic orchid Luisia teres (Asparagales: Orchidaceae) releases floral scent that attracts males of the cupreous polished chafer Protaetia pryeri pryeri (Coleoptera: Scarabaeidae) for pollination. We analyzed this floral scent to identify the attractant(s). When various flower parts were extracted with diethyl ether and assayed, male chafers were attracted to the extract of petals but not to that of sepals or lips. The petal extracts were chromatographed on silica gel column and the activity was found in ether and methanol fractions. Gas chromatography/mass spectrometry (GC/MS) analyses and subsequent NMR analyses revealed that both active fractions contained 2,3-dihydroxypropyl isovalerate (2,3-DHPiV) as a major compound. Natural 2,3-DHPiV showed identical retention time to that of synthetic (R)-enantiomer in subsequent HPLC analyses using a chiral column, while (S)-enantiomer was not detected. The amount of this compound was ca. 5?μg/flower. In field tests performed in Okinawa, Japan, males of P. pryeri pryeri were observed to fly around and land on a cotton ball impregnated with synthetic (R)-2,3-DHPiV, but no male was attracted to the (S)-enantiomer or the racemic mixture. Thus, the chemical attractant released from the flower was identified to be (R)-2,3-DHPiV. 2,3-DHPiV was also found in a volatile sample collected from the virgin females by GC/MS analyses using achiral column, while this compound did not occur in males. Because of the difficulty in HPLC detection of a small amount of 2,3-DHPiV, the chirality remains to be determined. Nevertheless, these results strongly suggest that the flowers of L. teres release the same compound as females of its pollinator P. pryeri pryeri, indicating that the flower of this orchid chemically mimics the female sex pheromone.
期刊介绍:
It is the aim of Chemoecology to promote and stimulate basic science in the field of chemical ecology by publishing research papers that integrate evolution and/or ecology and chemistry in an attempt to increase our understanding of the biological significance of natural products. Its scopes cover the evolutionary biology, mechanisms and chemistry of biotic interactions and the evolution and synthesis of the underlying natural products. Manuscripts on the evolution and ecology of trophic relationships, intra- and interspecific communication, competition, and other kinds of chemical communication in all types of organismic interactions will be considered suitable for publication. Ecological studies of trophic interactions will be considered also if they are based on the information of the transmission of natural products (e.g. fatty acids) through the food-chain. Chemoecology further publishes papers that relate to the evolution and ecology of interactions mediated by non-volatile compounds (e.g. adhesive secretions). Mechanistic approaches may include the identification, biosynthesis and metabolism of substances that carry information and the elucidation of receptor- and transduction systems using physiological, biochemical and molecular techniques. Papers describing the structure and functional morphology of organs involved in chemical communication will also be considered.