This article may be too technical for most readers to understand.(February 2015) |
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Preferred IUPAC name (1R,4aS,7S,7aR)-1-Hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid | |
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3D model (JSmol) | |
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CompTox Dashboard (EPA) | |
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Properties | |
C10H14O4 | |
Molar mass | 198.218 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
7-Deoxyloganetic acid is an iridoid monoterpene. It is produced from nepetalactol or iridodial by the enzyme iridoid oxidase (IO). [1] 7-Deoxyloganetic acid is a substrate for 7-deoxyloganetic acid glucosyltransferase (7-DLGT) which synthesizes 7-deoxyloganic acid. [2]
Catharanthus is a genus of flowering plants in the family Apocynaceae. Like the genus Vinca, they are known commonly as periwinkles. There are eight known species. Seven are endemic to Madagascar, though one, C. roseus, is widely naturalized around the world. The eighth species, C. pusillus, is native to India and Sri Lanka. The name Catharanthus comes from the Greek for "pure flower".
Vincristine, also known as leurocristine and marketed under the brand name Oncovin among others, is a chemotherapy medication used to treat a number of types of cancer. This includes acute lymphocytic leukemia, acute myeloid leukemia, Hodgkin's disease, neuroblastoma, and small cell lung cancer among others. It is given intravenously.
Catharanthus roseus, commonly known as bright eyes, Cape periwinkle, graveyard plant, Madagascar periwinkle, old maid, pink periwinkle, rose periwinkle, is a perennial species of flowering plant in the family Apocynaceae. It is native and endemic to Madagascar, but is grown elsewhere as an ornamental and medicinal plant, and now has a pantropical distribution. It is a source of the drugs vincristine and vinblastine, used to treat cancer. It was formerly included in the genus Vinca as Vinca rosea.
Vinca alkaloids are a set of anti-mitotic and anti-microtubule alkaloid agents originally derived from the periwinkle plant Catharanthus roseus and other vinca plants. They block beta-tubulin polymerization in a dividing cell.
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.
Ambovombe-Androy, or just Ambovombe, is a city in the far south of Madagascar, and the capital of the Androy region. Ambovombe has now acquired city status with an officially estimated population in 2018 of 114,230.
Strictosidine synthase (EC 4.3.3.2) is an enzyme in alkaloid biosynthesis that catalyses the condensation of tryptamine with secologanin to form strictosidine in a formal Pictet–Spengler reaction:
Rosinidin is an O-methylated anthocyanidin derived from Cyanidin. It is a pigment found in the flowers of Catharanthus roseus and, in lower concentration, in Primula rosea.
Hirsutidin is an O-methylated anthocyanidin, a chemical compound belonging to the anthocyanins. It can be found in Catharanthus roseus where it is the prominent compound in petals and can also be found in callus cultures.
The O-methylated flavonoids or methoxyflavonoids are flavonoids with methylations on hydroxyl groups. O-methylation has an effect on the solubility of flavonoids.
Ajmalicine, also known as δ-yohimbine or raubasine, is an antihypertensive drug used in the treatment of high blood pressure. It has been marketed under numerous brand names including Card-Lamuran, Circolene, Cristanyl, Duxil, Duxor, Hydroxysarpon, Iskedyl, Isosarpan, Isquebral, Lamuran, Melanex, Raunatin, Saltucin Co, Salvalion, and Sarpan. It is an alkaloid found naturally in various plants such as Rauvolfia spp., Catharanthus roseus, and Mitragyna speciosa.
Secologanin is a secoiridoid monoterpene synthesized from geranyl pyrophosphate in the mevalonate pathway. Secologanin then proceeds with dopamine or tryptamine to form ipecac and terpene indole alkaloids, respectively.
Akuammicine is a monoterpene indole alkaloid of the Vinca sub-group. It is found in the Apocynaceae family of plants including Picralima nitida, Vinca minor and the Aspidosperma.
Vindoline is a chemical precursor to vinblastine. Vindoline is formed through biosynthesis from Tabersonine.
Strictosidine is a natural chemical compound and is classified as a glucoalkaloid and a vinca alkaloid. It is formed by the Pictet–Spengler condensation reaction of tryptamine with secologanin, catalyzed by the enzyme strictosidine synthase. Thousands of strictosidine derivatives are sometimes referred to by the broad phrase of monoterpene indole alkaloids. Strictosidine is an intermediate in the biosynthesis of numerous pharmaceutically valuable metabolites including quinine, camptothecin, ajmalicine, serpentine, vinblastine, vincristine and mitragynine.
Deacetylvindoline is a terpene indole alkaloid produced by Catharanthus roseus. Deacetylvindoline is the product of a hydroxylation of desacetoxyvindoline by deacetoxyvindoline 4-hydroxylase (D4H). It is a substrate for deacetylvindoline O-acetyltransferase (DAT) which acetylates a hydroxy group to form vindoline, one of the two immediate precursors for the formation of the pharmacetucially valuable bisindole alkaloid vinblastine.
8-Hydroxygeraniol is a monoterpene synthesized from geraniol by the enzyme geraniol 8-hydroxylase. 8-Hydroxygeraniol is a substrate for 8-hydroxygeraniol dehydrogenase (G80) which synthesizes 8-oxogeranial. 8-Hydroxygeraniol is step in the synthesis of the secologanin, a key monoterpene needed for formation of terpene indole alkaloids.
8-Oxogeranial is a chemical substance, that is a monoterpene. The terpenoid is produced by 8-hydroxygeraniol dehydrogenase which uses 8-hydroxygeraniol as its substrate. 8-Oxogeranial is itself a substrate for iridoid synthase which synthesizes cis–trans-iridodial and cis–trans-nepetalactol.
7-Deoxyloganic acid is an iridoid monoterpene. 7-Deoxyloganic acid is produced from 7-deoxyloganetic acid by the enzyme 7-deoxyloganetic acid glucosyltransferase (7-DLGT). The metabolite is a substrate for the enzyme 7-deoxyloganic acid hydroxylase (7-DLH) which synthesizes loganic acid.
Loganic acid is an iridoid. Loganic acid is synthesized from 7-deoxyloganic acid by the enzyme 7-deoxyloganic acid hydroxylase (7-DLH). It is a substrate for the enzyme loganate O-methyltransferase for the production of loganin.