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Hydroxydanaidal
Hydroxydanaidal is an insect pheromone biosynthesis, synthesized by some species of moth from pyrrolizidine alkaloids found in their diet. Use The caterpillars of several kinds of Arctiidae, arctiid moth Pyrrolizidine alkaloid sequestration, ingest pyrrolizidine alkaloids—substances which plants produce to deter herbivores—and use them as protection against insectivores. The larva converts the alkaloid into an amine oxide, ''N''-oxide for storage; on metamorphosis, the alkaloid is retained and used by the adult. This was discovered after the observation that ''Utetheisa ornatrix'' moths caught in spiderwebs were cut loose by the spiders. Many insects that carry pyrrolizidine alkaloids are brightly-colored to signal their toxicity. Male tiger moths convert the alkaloid through various intermediate stages into the pheromone hydroxydanaidal;{{cite journal , journal=J Chem Ecol , author=J A Edgar, M Boppré, E Kaufmann , title=Insect-synthesised Retronecine Ester Alkaloids: ...
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Utetheisa Ornatrix
''Utetheisa ornatrix'', also called the bella moth, ornate moth or rattlebox moth is a moth of the subfamily Arctiinae. It is aposematically colored ranging from pink, red, orange and yellow to white coloration with black markings arranged in varying patterns on its wings. It has a wingspan of 33–46 mm. Moths reside in temperate midwestern and eastern North America as well as throughout Mexico and other parts of Central America. Unlike most moths, the bella moth is diurnal. Formerly, the bella moth or beautiful utetheisa of temperate eastern North America was separated as ''Utetheisa bella''. Now it is united with the bella moth in ''Utetheisa ornatrix''. The larvae usually feed on ''Crotalaria'' species, which contain poisonous alkaloid compounds that render them unpalatable to most predators. Larvae may prey on other bella moth larvae in order to compensate for any alkaloid deficiency. The bella moth also demonstrates complex mating strategies and is thus an excellent ...
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Pyrrolizidine Alkaloid Sequestration
Pyrrolizidine alkaloid sequestration by insects is a strategy to facilitate defense and mating. Various species of insects have been known to use molecular compounds from plants for their own defense and even as their pheromones or precursors to their pheromones. A few Lepidoptera have been found to sequester chemicals from plants which they retain throughout their life and some members of Erebidae are examples of this phenomenon. Starting in the mid-twentieth century researchers investigated various members of Arctiidae, and how these insects sequester pyrrolizidine alkaloids (PAs) during their life stages, and use these chemicals as adults for pheromones or pheromone precursors. PAs are also used by members of the Arctiidae for defense against predators throughout the life of the insect. Overview Pyrrolizidine alkaloids are a group of chemicals produced by plants as secondary metabolites, all of which contain a pyrrolizidine nucleus. This nucleus is made up of two pyrrole rings bo ...
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Pheromone
A pheromone () is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting like hormones outside the body of the secreting individual, to affect the behavior of the receiving individuals. There are ''alarm signal, alarm pheromones'', ''food trail pheromones'', ''sex pheromones'', and many others that affect behavior or physiology. Pheromones are used by many organisms, from basic unicellular prokaryotes to complex multicellular eukaryotes. Their use among insects has been particularly well documented. In addition, some vertebrates, plants and ciliates communicate by using pheromones. The ecological functions and evolution of pheromones are a major topic of research in the field of chemical ecology. Background The portmanteau word "pheromone" was coined by Peter Karlson and Martin Lüscher in 1959, based on the Greek φερω ''pheroo'' ('I carry') and ὁρμων ''hormon'' ('stimulating'). P ...
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Biosynthesis
Biosynthesis is a multi-step, enzyme-catalyzed process where substrates are converted into more complex products in living organisms. In biosynthesis, simple compounds are modified, converted into other compounds, or joined to form macromolecules. This process often consists of metabolic pathways. Some of these biosynthetic pathways are located within a single cellular organelle, while others involve enzymes that are located within multiple cellular organelles. Examples of these biosynthetic pathways include the production of lipid membrane components and nucleotides. Biosynthesis is usually synonymous with anabolism. The prerequisite elements for biosynthesis include: precursor compounds, chemical energy (e.g. ATP), and catalytic enzymes which may require coenzymes (e.g.NADH, NADPH). These elements create monomers, the building blocks for macromolecules. Some important biological macromolecules include: proteins, which are composed of amino acid monomers joined via peptide bon ...
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Pyrrolizidine Alkaloid
Pyrrolizidine alkaloids (PAs), sometimes referred to as necine bases, are a group of naturally occurring alkaloids based on the structure of pyrrolizidine. Pyrrolizidine alkaloids are produced by plants as a defense mechanism against insect herbivores. More than 660 PAs and PA N-oxides have been identified in over 6,000 plants, and about half of them exhibit hepatotoxicity. They are found frequently in plants in the Boraginaceae, Asteraceae, Orchidaceae and Fabaceae families; less frequently in the Convolvulaceae and Poaceae, and in at least one species in the Lamiaceae. It has been estimated that 3% of the world’s flowering plants contain pyrrolizidine alkaloids. Honey can contain pyrrolizidine alkaloids, as can grains, milk, offal and eggs. To date (2011), there is no international regulation of PAs in food, unlike those for herbs and medicines. Unsaturated pyrrolizidine alkaloids are hepatotoxic, that is, damaging to the liver. PAs also cause hepatic veno-occlusive disea ...
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Arctiidae
The Arctiinae (formerly called the family Arctiidae) are a large and diverse subfamily of moths with around 11,000 species found all over the world, including 6,000 neotropical species.Scoble, MJ. (1995). ''The Lepidoptera: Form, Function and Diversity''. Second ed. Oxford University Press. This subfamily includes the groups commonly known as tiger moths (or tigers), which usually have bright colours, footmen, which are usually much drabber, lichen moths, and wasp moths. Many species have "hairy" caterpillars that are popularly known as woolly bears or woolly worms. The scientific name Arctiinae refers to this hairiness (Gk. αρκτος = a bear). Some species within the Arctiinae have the word "tussock"' in their common names because they have been misidentified as members of the Lymantriinae subfamily based on the characteristics of the larvae. Taxonomy The subfamily was previously classified as the family Arctiidae of the superfamily Noctuoidea and is a monophyletic group. ...
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Amine Oxide
In chemistry, an amine oxide, also known as an amine ''N''-oxide or simply ''N''-oxide, is a chemical compound that contains the functional group , a nitrogen-oxygen coordinate covalent bond with three additional hydrogen and/or substituent-group side chains attached to N. Sometimes it is written as →O or, incorrectly, as . In the strict sense, the term ''amine oxide'' applies only to oxides of tertiary amines. Sometimes it is also used for the analogous derivatives of primary and secondary amines. Examples of amine oxides include pyridine-''N''-oxide, a water-soluble crystalline solid with melting point 62–67 °C, and ''N''-methylmorpholine ''N''-oxide, which is an oxidant. Applications Amine oxides are surfactants commonly used in consumer products such as shampoos, conditioners, detergents, and hard surface cleaners. Alkyl dimethyl amine oxide (chain lengths C10–C16) is the most commercially used amine oxide. They are considered a high production volume class of ...
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Insect Pheromones
Insects (from Latin ') are pancrustacean Hexapoda, hexapod invertebrates of the class (biology), class Insecta. They are the largest group within the arthropod phylum. Insects have a chitinous exoskeleton, a three-part body (head, Thorax (insect anatomy), thorax and abdomen (insect anatomy), abdomen), three pairs of jointed Arthropod leg, legs, compound eyes and one pair of antenna (biology), antennae. Their blood is not totally contained in vessels; some circulates in an open cavity known as the haemocoel. Insects are the most diverse group of animals; they include more than a million described species and represent more than half of all known living organisms. The total number of Extant taxon, extant species is estimated at between six and ten million; In: potentially over 90% of the animal life forms on Earth are insects. Insects may be found in nearly all Natural environment, environments, although only a small number of species reside in the oceans, which are dominated by ...
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Aromatic Aldehydes
In chemistry, aromaticity is a chemical property of cyclic (ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to saturated compounds having single bonds, and other geometric or connective non-cyclic arrangements with the same set of atoms. Aromatic rings are very stable and do not break apart easily. Organic compounds that are not aromatic are classified as aliphatic compounds—they might be cyclic, but only aromatic rings have enhanced stability. The term ''aromaticity'' with this meaning is historically related to the concept of having an aroma, but is a distinct property from that meaning. Since the most common aromatic compounds are derivatives of benzene (an aromatic hydrocarbon common in petroleum and its distillates), the word ''aromatic'' occasionally refers informally to benzene derivatives, and so it was first defined. Nevertheless, many non-benz ...
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Secondary Alcohols
In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl () functional group bound to a saturated carbon atom. The term ''alcohol'' originally referred to the primary alcohol ethanol (ethyl alcohol), which is used as a drug and is the main alcohol present in alcoholic drinks. An important class of alcohols, of which methanol and ethanol are the simplest examples, includes all compounds which conform to the general formula . Simple monoalcohols that are the subject of this article include primary (), secondary () and tertiary () alcohols. The suffix ''-ol'' appears in the IUPAC chemical name of all substances where the hydroxyl group is the functional group with the highest priority. When a higher priority group is present in the compound, the prefix ''hydroxy-'' is used in its IUPAC name. The suffix ''-ol'' in non-IUPAC names (such as paracetamol or cholesterol) also typically indicates that the substance is an alcohol. However, some compound ...
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