Insect chemistry and chirality (original) (raw)
Related papers
Chemical Defenses of Insects: A Rich Resource for Chemical Biology in the Tropics
Springer eBooks, 2011
Insects make up the largest and most diverse group of organisms on earth, contributing to as much as 80-90% of the world's biodiversity. Approximately 950,000 species of insects have been described; some estimate there are 4,000,000þ species in total. Over 70% of drugs on the market are derived from natural compounds. However, insects are one of the least explored groups in drug discovery. The world adds about 70 million people each year. In this chapter you will find: (1) an introduction to the topic of arthropod chemical biodiversity and chemical defense; (2) a brief discussion on various uses of insect chemistry by various cultures; (3) an overview of insect venoms and other chemical defense studies, with a case study on methods utilized to analyze ant venoms; (4) a short discussion on the importance of preserving tropical habitats for bioprospecting; (5) a review of research on stick insect (Order Phasmatodea) chemical defenses, stick insects as a model for biosynthesis studies and my personal experiences with the editors of this book and 2008 PASI workshop in Peru which resulted in this chapter; (6) an overview of examples from the literature of insectderived substances with medicinally relevant biological properties such as toxins and antibiotics; (7) a brief description of the importance of studying biosynthetic pathways in insects and other organisms from whence valuable natural products are identified and (8) a list of recommended literature which I expect would be of particular interest to the readers of this chapter.
Insects and their chemical weaponry: New potential for drug discovery
Natural Product Reports, 2010
Insects make up the largest and most diverse group of organisms on earth, with nearly 1 million species described and millions more estimated to remain undiscovered. Like all other organisms, insects and related arthropods mainly utilize chemistry to adapt to these environments in a wide variety of ways, such as for defense against predation or infection, communication and socialization, life cycle development, and surviving environmental conditions. Arthropods harbor a large variety of chemical substances used for these ecological adaptations, and this is the overarching theme of the field of chemical ecology. Progress in the field has advanced rapidly, and this comprehensive review summarizes the enormous potential for discovery of new natural products with medicinal value from among the phylum Arthropoda. This review: (1) introduces the topic of arthropod chemical biodiversity; (2) reviews cultural uses of arthropods as medicines; (3) provides an overview of insect chemical defense studies and modern natural product analytical methods; (4) describes examples from the literature of insect-derived substances with medicinally relevant biological properties; and (5) summarizes the aforementioned topics to emphasize the value of arthropods as reservoirs of potentially useful new natural products.
Stereochemistry of two pheromonal components of the bumblebee wax moth, Aphomia sociella
Scientific Reports
the bumblebee wax moth, Aphomia sociella, is a parasite of bumblebees. in this species, males produce sexual pheromone to attract females, while females produce an aphrodisiac pheromone that initiates male courtship. Both pheromones contain 6,10,14-trimethylpentadecan-2-one (TMPD-one) and the corresponding alcohol, 6,10,14-trimethylpentadecan-2-ol (TMPD-ol) in sex specific quantities. Male sex pheromone consists of 7 components with TMPD-one as a minor one and traces of TMPD-ol. In female aphrodisiac pheromone, TMPD-ol is the major component, while TMPD-one is present in traces. Here we report on the absolute configuration of TMPD-one in male sex pheromone and TMPD-ol in female aphrodisiac pheromone of A. sociella. The configuration was determined from GC/MS of prepared (S)-acetoxypropionyl esters of TMPD-ol. TMPD-one was first reduced to the alcohol that was then derivatized with (S)-acetoxypropionyl chloride. The GC/MS data of obtained diastereoisomers were compared with synthetic standards. The absolute configuration of TMPD-one in the male pheromone was (6R,10R). The configuration of TMPD-ol in the female pheromone was (2R,6R,10R). Electrophysiological experiments showed that TMPD-one and TMPD-ol are perceived by both sexes. the synthetic standards of naturally produced stereoisomers elicited higher responses than mixtures of all stereoisomers.
Isoprenol biosynthesis in the fly, Sarcophaga bullata
Insect Biochemistry, 1972
Biosynthesis of the isoprenols, geranlol, farnesol, nerolidol, and geranylgeraniol, from [2-1'C]mevalonic acid is described in the fly, Sarcophaga/m//ata. Each was identified by thin-layer and gas chromatographic, infra-red spectroscopic, and mass spectrometric analyses. • These isopreno]s underwent structural rearrangement when acid hydrolysis was used to isolate them from their pyrophoephates. Most of the farnesyl pyrophosphate was converted to nerolidol, while only a fraction of the geranyl pyrophosphate was changed to its isomers. Since farnesol is the major isoprenol product of the b~ vivo incubation, we conclude that this insect is capable of isoprenoid biosynthesis at least to this point, and that the block in the cholesterol biosynthetic pathway lies beyond.
Chemistry, biochemistry, and physiology of insect cuticular lipids
Archives of Insect Biochemistry and Physiology, 1987
The chemistry, biochemistry, and physiology of insect cuticular lipids are reviewed. The types of components present in cuticular extracts are described with special emphasis on the occurrence and identification of the di-and trimethylalkanes and the newly discovered tetramethylalkanes. The methods used in the extraction of cuticular components are discussed, including recommendations to standardize procedures. The structural elucidation of methylalkanes, particularly the mass spectral interpretation of multi-methylbranched alkanes, is reviewed. The biosynthesis of cuticular lipids is discussed with emphasis on the hydrocarbon components, describing elongation reactions and the origin of the methyl branches. The effects of environment and development on cuticular lipids are reviewed.
Physiological and Biochemical Zoology, 2006
Chemical communication is virtually universal among terrestrial and aquatic organisms. Chemical signals control the interactions of cells and organs (hormones) as well as the intra-(pheromones) and interspecific (allelochemicals) relationships between animals. The review considers three examples for chemical communication in insects and other arthropods on different hierarchic levels of biological organization, from the intraindividual level, where hormones control development and reproduction of the animals, to the interspecific level, where semiochemicals function as defense agents against predators or may be used for finding and recognizing food resources. Knowledge of the function of these systems and of the molecular structures of the chemical compounds involved may provide the basis for highly selective techniques of pest control. * This paper was prepared as an overview of a symposium session presented at "Animals and Environments," the Third International Conference for Comparative Physiology and Biochemistry, Ithala Game Reserve, KwaZulu-Natal, South Africa, 2004 (http://www.natural-events.com/ithala/default-follow\_2.asp).