Purdue University Purdue e-Pubs Open Access Dissertations Theses and Dissertations January 2016 The nflueI nce of Chirality on the Behavioral Responses of Longhorned Beetles (Coleoptera: Cerambycidae) to Volatile and Contact Pheromones Gabriel Patrick Hughes Purdue University Follow this and additional works at: https://docs.lib.purdue.edu/open_access_dissertations Recommended Citation Hughes, Gabriel Patrick, "The nflueI nce of Chirality on the Behavioral Responses of Longhorned Beetles (Coleoptera: Cerambycidae) to Volatile and Contact Pheromones" (2016). Open Access Dissertations. 1216. https://docs.lib.purdue.edu/open_access_dissertations/1216 This document has been made available through Purdue e-Pubs, a service of the Purdue University Libraries. Please contact [email protected] for additional information. THE INFLUENCE OF CHIRALITY ON THE BEHAVIORAL RESPONSES OF LONGHORNED BEETLES (COLEOPTERA: CERAMBYCIDAE) TO VOLATILE AND CONTACT PHEROMONES by Gabriel P. Hughes A Dissertation Submitted to the Faculty of Purdue University In Partial Fulfillment of the Requirements for the degree of Doctor of Philosophy Department of Entomology West Lafayette, Indiana December 2016 ii THE PURDUE UNIVERSITY GRADUATE SCHOOL STATEMENT OF DISSERTATION APPROVAL Dr. Matthew D. Ginzel, Chair Department of Entomology Dr. Michael E. Scharf Department of Entomology Dr. Clifford S. Sadof Department of Entomology Dr. Richard Meilan Department of Forestry and Natural Resources Approved by: Dr. Stephen L. Cameron Head of the Departmental Graduate Program iv ACKNOWLEDGMENTS I would like to thank God and my family for their tireless help and support as I have pursued my education. I thank my advisor, Dr. Matthew Ginzel, for training me in the ways of a true scientist. I thank my committee members for their support and encouragement. I have many people to thank for their assistance on individual chapters of this dissertation. Chapter 2: I thank the Indiana Department of Natural Resources, Division of Nature Preserves and NICHES Land Trust Corporation for permitting me to collect beetles at Black Rock Barrens Nature Preserve. This research was funded by Purdue University Agricultural Research Programs, and this work was in published in Canadian Entomologist, and I express my thanks to the co-authors of this work. The manuscript is reprinted here with permission. Hughes GP, Zou Y, Millar JG, Ginzel MD (2013) Male-produced pheromone of the North American lamiine Astyleiopus variegatus (Coleoptera: Cerambycidae) is composed of (S)-fuscumol and (S)-fuscumol acetate. Can Entomol 145: 327–332 Chapter 3: I thank the Northern Indiana Citizens Helping Ecosystems Survive (NICHES) Land Trust and Tippecanoe County Parks and Recreation Department for allowing me to conduct experiments on their properties, and B. Blood, M. Paschen, T. Stewart, and K. Strack for assistance with field work and identifying beetles. I appreciate funding support from the Alphawood Foundation of Chicago (to LMH), and the Purdue Research Foundation (to MDG). This chapter has been accepted for publication in Environmental Entomology, and I thank the coauthors of this work. This manuscript is reprinted here with permission. Hughes GP, Meier LR, Zou Y, Millar JG, Hanks LM, Ginzel MD (accepted) Stereochemistry of fuscumol and fuscumol acetate influences attraction of longhorned beetles (Coleoptera: Cerambycidae) of the subfamily Lamiinae. Environ Entomol DOI: http://dx.doi.org/10.1093/ee/nvw101, 1271–1275 v Chapter 4: I thank L. M. Hanks for providing pheromone lures to collect Neoclytus a. acuminatus and for supplying female N. a. acuminatus for the CHC isolation and polarimetric studies. I thank J. Hesser, T. Stewart, and K. Strack for assisting with bioassays. I thank B. Blood and T. Stewart for reviewing an early draft of the manuscript. This research was funded in part by the Purdue Research Foundation, and by Hatch project CA-R*ENT-5181-H to J.G.M. This work was published in the Journal of Chemical Ecology, and I thank the coauthors of this work. This manuscript is reprinted here with permission. Hughes GP, Bello JE, Millar JG, Ginzel MD (2015) Determination of the absolute configuration of female-produced contact sex pheromone components of the longhorned beetle, Neocyltus acuminatus (F). J Chem Ecol 41:1050-1057 Chapter 5: I thank M. E. Scharf for his collaboration and letting me use his lab space. I thank B. F. Peterson for her guidance with experimental setup, and for reading a draft of this chapter. I thank S. Rajarapu for teaching me qRT-PCR, and M. Dittmann, A. Meyers, G. Price, and M. Rushton for their assistance in the lab. This project was funded by USDA NIFA-AFRI Predoctoral Fellowship. # 2015-03631 vi TABLE OF CONTENTS LIST OF TABLES ............................................................................................................. ix LIST OF FIGURES ............................................................................................................ x ABSTRACT ....................................................................................................................... xi CHAPTER 1: REVIEW OF CHIRALITY IN THE CHEMICAL COMMUNICATION SYSTEMS OF THE LONGHORNED BEETLES (COLEOPTERA: CERAMBYCIDAE) .............................................................................. 1 1.1 Introduction .............................................................................................................. 1 1.1.1 Longhorned Beetles .......................................................................................... 1 1.1.2 Chirality and Insect Chemical Communication ................................................ 2 1.2 Volatile Pheromones ................................................................................................ 3 1.2.1 Male-Produced Pheromones ............................................................................. 3 1.2.2 Female-Produced Pheromones.......................................................................... 5 1.3 Contact Pheromones ................................................................................................. 6 1.4 Summary .................................................................................................................. 7 1.5 References ................................................................................................................ 9 CHAPTER 2: (S)-FUSCUMOL AND (S)-FUSCUMOL ACETATE PRODUCED BY A MALE ASTYLEIOPUS VARIEGATUS (COLEOPTERA: CERAMBYCIDAE) ............. 15 2.1 Abstract .................................................................................................................. 15 2.2 Introduction ............................................................................................................ 16 2.3 Methods and Materials ........................................................................................... 17 2.4 Results .................................................................................................................... 20 2.5 Discussion .............................................................................................................. 21 2.6 References .............................................................................................................. 22 CHAPTER 3: STEREOCHEMISTRY OF FUSCUMOL AND FUSCUMOL ACETATE INFLUENCES ATTRACTION OF LONGHORNED BEETLES OF THE SUBFAMILY LAMIINAE ............................................................................................... 27 3.1 Abstract .................................................................................................................. 27 3.2 Introduction ............................................................................................................ 28 vii 3.3 Methods and Materials ........................................................................................... 30 3.3.1 Sources of Chemicals...................................................................................... 30 3.3.2 Study Sites ...................................................................................................... 30 3.3.3 Field Screening Experiments .......................................................................... 30 3.4 Results .................................................................................................................... 32 3.5 Discussion .............................................................................................................. 33 3.6 References .............................................................................................................. 35 CHAPTER 4: DETERMINATION OF THE ABSOLUTE CONFIGURATION OF FEMALE-PRODUCED CONTACT SEX PHEROMONE COMPONENTS OF THE LONGHORNED BEETLE, NEOCLYTUS ACUMINATUS ACUMINATUS (F.) (COLEOPTERA: CERAMBYCIDAE) ............................................................................ 45 4.1 Abstract .................................................................................................................. 45 4.2 Introduction ............................................................................................................ 46 4.3 Methods and Materials ........................................................................................... 48 4.3.1 Sources of Beetles ........................................................................................... 48 4.3.2 Authentic Standards of Methyl-Branched CHC Enantiomers ........................ 49 4.3.3 Extraction of CHCs from Female N. a. acuminatus