Catalpol
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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 o ...
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Iridoid
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 Glycosides
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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Lamiales
The order Lamiales (also known as the mint order) are an order in the asterid group of dicotyledonous flowering plants. It includes about 23,810 species, 1,059 genera, and is divided into about 25 families. These families include Acanthaceae, Bignoniaceae, Byblidaceae, Calceolariaceae, Carlemanniaceae, Gesneriaceae, Lamiaceae, Lentibulariaceae, Linderniaceae, Martyniaceae, Mazaceae, Oleaceae, Orobanchaceae, Paulowniaceae, Pedaliaceae, Peltantheraceae, Phrymaceae, Plantaginaceae, Plocospermataceae, Schlegeliaceae, Scrophulariaceae, Stilbaceae, Tetrachondraceae, Thomandersiaceae, Verbenaceae. Being one of the largest orders of flowering plants, Lamiales have representatives found all over the world. Well-known or economically important members of this order include lavender, lilac, olive, jasmine, the ash tree, teak, snapdragon, sesame, psyllium, garden sage, and a number of table herbs such as mint, basil, and rosemary. Description Plant species within the order Lamiales are ...
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Glucosides
A glucoside is a glycoside that is derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes. The name was originally given to plant products of this nature, in which the other part of the molecule was, in the greater number of cases, an aromatic aldehydic or phenolic compound (exceptions are Jinigrin and Jalapin or Scammonin). It has now been extended to include synthetic ethers, such as those obtained by acting on alcoholic glucose solutions with hydrochloric acid, and also the polysaccharoses, e.g. cane sugar, which appear to be ethers also. Although glucose is the most common sugar present in glucosides, many are known which yield rhamnose or iso-dulcite; these may be termed pentosides. Much attention has been given to the non-sugar parts (aglyca) of the molecules; the constitutions of many have been determined, and the compounds synthes ...
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Biosynthesis Of Catalpol
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 ...
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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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Geniposidic Acid
Geniposidic acid is a natural chemical compound, classified as an iridoid glucoside, found in a variety of plants including ''Eucommia ulmoides'' and ''Gardenia jasminoides ''Gardenia jasminoides'', commonly known as gardenia, is an evergreen flowering plant in the coffee family Rubiaceae. It is native to parts of South-East Asia. Wild plants range from 30 centimetres to 3 metres (about 1 to 10 feet) in height. The ...''. References Iridoid glycosides Glucosides Carboxylic acids Cyclopentenes {{organic-compound-stub ...
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Geraniol
Geraniol is a monoterpenoid and an alcohol. It is the primary component of citronella oil and is a primary component of rose oil, palmarosa oil. It is a colorless oil, although commercial samples can appear yellow. It has low solubility in water, but it is soluble in common organic solvents. The functional group derived from geraniol (in essence, geraniol lacking the terminal −OH) is called geranyl. Uses and occurrence In addition to rose oil, palmarosa oil, and citronella oil, it also occurs in small quantities in geranium, lemon, and many other essential oils. With a rose-like scent, it is commonly used in perfumes. It is used in flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. Geraniol is produced by the scent glands of honeybees to mark nectar-bearing flowers and locate the entrances to their hives. It is also commonly used as an insect repellent, especially for mosquitoes. The scent of geraniol ...
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Terpenoid
The terpenoids, also known as isoprenoids, are a class of naturally occurring organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeably with "terpenes", terpenoids contain additional functional groups, usually containing oxygen. When combined with the hydrocarbon terpenes, terpenoids comprise about 80,000 compounds. They are the largest class of plant secondary metabolites, representing about 60% of known natural products. Many terpenoids have substantial pharmacological bioactivity and are therefore of interest to medicinal chemists. Plant terpenoids are used for their aromatic qualities and play a role in traditional herbal remedies. Terpenoids contribute to the scent of eucalyptus, the flavors of cinnamon, cloves, and ginger, the yellow color in sunflowers, and the red color in tomatoes. Well-known terpenoids include citral, menthol, camphor, salvinorin A in the plant '' Salvia di ...
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Biosynthetic Pathway
Metabolism (, from el, μεταβολή ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cellular processes; the conversion of food to building blocks for proteins, lipids, nucleic acids, and some carbohydrates; and the elimination of metabolic wastes. These enzyme-catalyzed reactions allow organisms to grow and reproduce, maintain their structures, and respond to their environments. The word metabolism can also refer to the sum of all chemical reactions that occur in living organisms, including digestion and the transportation of substances into and between different cells, in which case the above described set of reactions within the cells is called intermediary (or intermediate) metabolism. Metabolic reactions may be categorized as ''catabolic'' – the ''breaking down'' of compounds (for example, of glucose to pyruvate by cel ...
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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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Bignoniaceae
Bignoniaceae is a family of flowering plants in the order Lamiales commonly known as the bignonias or trumpetvines.Vernon H. Heywood, Richard K. Brummitt, Ole Seberg, and Alastair Culham. ''Flowering Plant Families of the World''. Firefly Books: Ontario, Canada. (2007). . It is not known to which of the other families in the order it is most closely related.Peter F. Stevens (2001 onwards). "Bignoniaceae" At: Angiosperm Phylogeny Website. At: Botanical Databases At: Missouri Botanical Garden Website. (see ''External links'' below) Nearly all of the Bignoniaceae are woody plants, but a few are subwoody, either as vines or subshrubs. A few more are herbaceous plants of high-elevation Montane ecology, montane habitats, in three exclusively herbaceous genera: ''Tourrettia'', ''Argylia'', and ''Incarvillea''. The family includes many lianas, climbing by tendrils, by twining, or rarely, by aerial roots. The largest Tribe (biology), tribe in the family, called Bignonieae, consists mostly ...
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