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Iridoids
Iridoids are a type of monoterpenoids in the general form of cyclopentanopyran, found in a wide variety of plants and some animals. They are biosynthetically derived from 8-oxogeranial. Iridoids are typically found in plants as glycosides, most often bound to glucose. The chemical structure is exemplified by iridomyrmecin, a defensive chemical produced by the ant genus ''Iridomyrmex'', for which iridoids are named. Structurally, they are bicyclic ''cis''-fused cyclopentane-pyrans. Cleavage of a bond in the cyclopentane ring gives rise to a subclass known as ''secoiridoids'', such as oleuropein and amarogentin. Occurrence The iridoids produced by plants act primarily as a defense against herbivores or against infection by microorganisms. The variable checkerspot butterfly also contains iridoids obtained through its diet which act as a defense against avian predators. To humans and other mammals, iridoids are often characterized by a deterrent bitter taste. Aucubin and catal ...
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Iridoid Synthase
Iridoids are a type of monoterpenoids in the general form of cyclopentanopyran, found in a wide variety of plants and some animals. They are biosynthetically derived from 8-oxogeranial. Iridoids are typically found in plants as glycosides, most often bound to glucose. The chemical structure is exemplified by iridomyrmecin, a defensive chemical produced by the ant genus '' Iridomyrmex'', for which iridoids are named. Structurally, they are bicyclic ''cis''-fused cyclopentane-pyrans. Cleavage of a bond in the cyclopentane ring gives rise to a subclass known as ''secoiridoids'', such as oleuropein and amarogentin. Occurrence The iridoids produced by plants act primarily as a defense against herbivores or against infection by microorganisms. The variable checkerspot butterfly also contains iridoids obtained through its diet which act as a defense against avian predators. To humans and other mammals, iridoids are often characterized by a deterrent bitter taste. Aucubin and ca ...
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Aucubin
Aucubin is an iridoid glycoside. Iridoids are commonly found in plants and function as defensive compounds. Iridoids decrease the growth rates of many generalist herbivores. Natural occurrences Aucubin, as other iridoids, is found in asterids such as ''Aucuba japonica'' (Garryaceae), ''Eucommia ulmoides'' (Eucommiaceae), ''Plantago asiatica'', ''Plantago major'', ''Plantago lanceolata'' (Plantaginaceae), '' Galium aparine'' (Rubiaceae) and others. These plants are used in traditional Chinese and folk medicine. Agnuside is composed of aucubin and ''p''-hydroxybenzoic acid. Health effects Aucubin was found to protect against liver damage induced by carbon tetrachloride or alpha-amanitin in mice and rats when 80 mg/kg was dosed intraperitoneally. Chemistry Aucubin is a monoterpenoid based compound. Aucubin, like all iridoids, has a cyclopentan- pyran skeleton. Iridoids can consist of ten, nine, or rarely eight carbons in which C11 is more frequently missing than C10 ...
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Catalpol
Catalpol is an iridoid glucoside. This natural product falls in the class of iridoid glycosides, which are simply monoterpenes with a glucose molecule attached. Natural occurrence First isolated in 1962, catalpol was named for plants in the genus ''Catalpa'' in which it was discovered. Later in 1969, catalpol was found to be present in larger quantities in several plants in genus '' Rehmannia'' (Orobanchaceae). It is also found in plants belonging to several families, including, but not limited to, Scrophulariaceae, Lamiaceae (including scullcap), Plantaginaceae (''Plantago sp'') and Bignoniaceae, all of which being in the order Lamiales. Because they feed on these plants, variable checkerspot butterflies (''Euphydryas chalcedona'') contain high amounts of catalpol, which makes them unpalatable to predators and thus serves as a defense mechanism. Biosynthetic pathway Though first isolated in the 1960s, there has been very little investigation of the biosynthetic pathway ...
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Variable Checkerspot
The variable checkerspot or Chalcedon checkerspot (''Euphydryas chalcedona'') is a butterfly in the family Nymphalidae. It is found in western North America, where its range stretches from Alaska in the north to Baja California in the south and extends east through the Rocky Mountains into Colorado, Montana, New Mexico and Wyoming. The butterfly is usually brown or black with extensive white and yellow checkering and some red coloration on the dorsal wing. Adult wingspan is . Adult butterflies feed on nectar from flowers while larvae feed on a variety of plants including snowberry (''Symphoricarpos''), paintbrush (''Castilleja''), ''Buddleja'', '' Diplacus aurantiacus'' and ''Scrophularia californica''. During the breeding period, males congregate around larval host plants to encounter females. Males court female butterflies via physical displays.Rutowski, Ronald L., and George W. Gilchrist. "Courtship, Copulation and Oviposition in the Chalcedon Checkerspot,(Lepidoptera: Nymphali ...
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Iridomyrmecin
Iridomyrmecin is a defensive chemical, classified as an iridoid, isolated from ants of the genus ''Iridomyrmex''. It has also evolved into a sex pheromone in wasps such as ''Leptopilina'', with host species using the smell of iridomyrmecin as a way of detecting the presence of the parasitoid wasps. Iridomyrmecin is also found in a variety of plants including ''Actinidia polygama ''Actinidia polygama'' (also known as , silver vine, , and cat powder) is a species of kiwifruit in the Actinidiaceae family. It grows in the mountainous areas of Korea, Japan and China at elevations between . Silver vine can reach up to high ...''. See also * Cat pheromone#Cat attractants for other chemicals that have behavioural effects on cats References Iridoids Lactones Cyclopentanes {{organic-compound-stub ...
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Oleaceae
Oleaceae, also known as the olive family, is a taxonomic family of flowering shrubs, trees, and a few lianas in the order Lamiales, It presently comprises 28 genera, one of which is recently extinct.Peter S. Green. 2004. "Oleaceae". pages 296-306. In: Klaus Kubitzki (editor) and Joachim W. Kadereit (volume editor). ''The Families and Genera of Vascular Plants'' volume VII. Springer-Verlag: Berlin; Heidelberg, Germany. The extant genera include ''Cartrema'', which was resurrected in 2012. The number of species in the Oleaceae is variously estimated in a wide range around 700. The flowers are often numerous and highly odoriferous.Vernon H. Heywood, Richard K. Brummitt, Ole Seberg, and Alastair Culham. ''Flowering Plant Families of the World''. Firefly Books: Ontario, Canada. . The family has a subcosmopolitan distribution, ranging from the subarctic to the southernmost parts of Africa, Australia, and South America. Notable members include olive, ash, jasmine, and several popular or ...
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Plantaginaceae
Plantaginaceae, the plantain family, is a large, diverse family of flowering plants in the order Lamiales that includes common flowers such as snapdragon and foxglove. It is unrelated to the banana-like fruit also called "plantain." In older classifications, Plantaginaceae was the only family of the order Plantaginales, but numerous phylogenetic studies, summarized by the Angiosperm Phylogeny Group, have demonstrated that this taxon should be included within Lamiales. Overview The plantain family as traditionally circumscribed consisted of only three genera: '' Bougueria'', '' Littorella'', and ''Plantago''. However phylogenetic research has indicated that Plantaginaceae ''sensu stricto'' (in the strict sense) were nested within Scrophulariaceae (but forming a group that did not include the type genus of that family, ''Scrophularia''). Although Veronicaceae (1782) is the oldest family name for this group, Plantaginaceae (1789) is a conserved name under the International Code of ...
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Scrophulariaceae
The Scrophulariaceae are a family of flowering plants, commonly known as the figwort family. The plants are annual and perennial herbs, as well as shrubs. Flowers have bilateral (zygomorphic) or rarely radial (actinomorphic) symmetry. The Scrophulariaceae have a cosmopolitan distribution, with the majority found in temperate areas, including tropical mountains. The family name is based on the name of the included genus '' Scrophularia'' L. Taxonomy In the past, it was treated as including about 275 genera and over 5,000 species, but its circumscription has been radically altered since numerous molecular phylogenies have shown the traditional broad circumscription to be grossly polyphyletic. Many genera have recently been transferred to other families within the Lamiales, notably Plantaginaceae and Orobanchaceae, but also several new families. - on linhere/ref> Several families of the Lamiales have had their circumscriptions enlarged to accommodate genera transferred fr ...
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Menyanthaceae
Menyanthaceae is a family of aquatic and wetland plants in the order Asterales. There are approximately 60-70 species in six genera distributed worldwide. The simple or compound leaves arise alternately from a creeping rhizome. In the submersed aquatic genus '' Nymphoides'', leaves are floating and support a lax, umbellate or racemose inflorescence. In other genera the inflorescence is erect and consists of one (e.g., ''Liparophyllum'') to many flowers. The sympetalous, insect-pollinated flowers are five-parted and either yellow or white. The petals are ciliate or adorned with lateral wings. Fruit type is a capsule. Species of Menyanthaceae are found worldwide. The genera ''Menyanthes'' and ''Nephrophyllidium'' grow only in the northern hemisphere, while ''Liparophyllum'' and ''Villarsia'' occur only in the southern hemisphere. '' Nymphoides'' species have a cosmopolitan distribution. Menyanthaceae species are of economic importance as ornamental water garden plants, with '' ...
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Valerianaceae
The Valerianaceae Batsch, the valerian family, was a family of flowering plants that is now considered part of the Caprifoliaceae. Plants are generally herbaceous, and their foliage often has a strong, disagreeable odor. They are found native in most regions of the world except for Australia. Some species are cultivated as ornamentals or used in herbal medicine for inducing relaxation and sleep. The genera that were placed in this family, along with some species, include: * '' Centranthus'' : ''C. ruber'' ( red valerian, spur valerian or red spur valerian) * ''Fedia'' : ''F. cornucopiae'' (African valerian, horn of plenty) * '' Nardostachys'' : '' N. jatamansi'' (Spikenard) : '' N. chinensis'' * ''Patrinia'' * '' Plectritis'' * '' Valeriana'' : ''V. dioica'' (marsh valerian) : ''V. officinalis'' (garden valerian) * ''Valerianella ''Valerianella'' is a genus of plant in family Caprifoliaceae. Many plants of this genus are known by the common name corn salad or cornsalad, al ...
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Verbenaceae
The Verbenaceae ( ), the verbena family or vervain family, is a family of mainly tropical flowering plants. It contains trees, shrubs, and herbs notable for heads, spikes, or clusters of small flowers, many of which have an aromatic smell. The family Verbenaceae includes 32 genera and 800 species. Phylogenetic studies have shown that numerous genera traditionally classified in Verbenaceae belong instead in Lamiaceae. The mangrove genus '' Avicennia'', sometimes placed in the Verbenaceae or in its own family, Avicenniaceae, has been placed in the Acanthaceae. Economically important Verbenaceae include: * Lemon verbena (''Aloysia triphylla''), grown for aroma or flavoring * Verbenas or vervains (''Verbena''), some used in herbalism, others grown in gardens Taxonomy Tribes and genera in the family and their estimated species numbers: Casselieae (Schauer) Tronc. * ''Casselia'' Nees & Mart. - 6 species * ''Parodianthus'' Tronc. - 2 species * ''Tamonea'' Aubl. - 6 species ...
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Monoterpene Cyclase
Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen functionality or missing a methyl group, are called monoterpenoids. Monoterpenes and monoterpenoids are diverse. They have relevance to the pharmaceutical, cosmetic, agricultural, and food industries. Biosynthesis Monoterpenes are derived biosynthetically from units of isopentenyl pyrophosphate, which is formed from acetyl-CoA via the intermediacy of mevalonic acid in the HMG-CoA reductase pathway. An alternative, unrelated biosynthesis pathway of IPP is known in some bacterial groups and the plastids of plants, the so-called MEP-(2-methyl-D-erythritol-4-phosphate) pathway, which is initiated from C5 sugars. In both pathways, IPP is isomerized to DMAPP by the enzyme isopentenyl pyrophosphate isomerase. Geranyl pyrophosphate is the precursor ...
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