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Encyclopedia > Terpenoids

The terpenoids, sometimes referred to as isoprenoids, are a large and diverse class of naturally occurring organic chemicals similar to terpenes, derived from five-carbon isoprene units assembled and modified in thousands of ways. Most are multicyclic structures which differ from one another not only in functional groups, but also in their basic carbon skeletons. These lipids can be found in all classes of living things, and are the largest group of natural products. Benzene is the simplest of the arenes, a family of organic compounds An organic compound is any member of a large class of chemical compounds whose molecules contain carbon and hydrogen; therefore, carbides, carbonates, carbon oxides and elementary carbon are not organic (see below for more on the definition controversy... Many terpenes are derived from conifer resins, here a pine. ... Isoprene is a common synonym for the chemical compound 2-methyl-1,3-butadiene. ... In organic chemistry, functional groups are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ... Lipids are a class of hydrocarbon-containing organic compounds. ...


Plant terpenoids are extensively used for their aromatic qualities. They play a role in traditional herbal remedies and are under investigation for antibacterial, antineoplastic and other pharmaceutical effects. Terpenoids contribute to the scent of eucalyptus, the flavors of cinnamon, cloves and ginger and the color of yellow flowers. Well-known terpenoids include citral, menthol, camphor and the cannabinoids found in the Cannabis plant. An antiseptic is a substance that kills or prevents the growth of bacteria on the external surfaces of the body. ... herbs that have the specific action of inhibiting and combating the development of tumors. ... Pharmacology (in Greek: pharmacon is drug, and logos is science) is the study of how chemical substances interfere with living systems. ... This article is about the plant genus. ... Binomial name Cinnamomum verum J.Presl Cassia (Indonesian cinnamon) is also commonly called (and sometimes sold as) cinnamon. ... This article is about spices, the word clove is also used to describe a segment of a head of garlic and a clove hitch is a useful kind of knot. ... Binomial name Zingiber officinale Roscoe Ginger is used extensively as a spice in cuisines throughout the world. ... Citral or 3,7-dimethylocta-2,6-dien-1-al or lemonal C10H16O is a chemical compound and part of the terpene family. ... Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. ... R-phrases 11-20/21/22-36/37/38 S-phrases 16-26-36 RTECS number EX1260000 (R) EX1250000 (S) Supplementary data page Structure and properties n, εr, etc. ... Cannabinoids are a group of chemicals which activate the bodys cannabinoid receptors. ... Look up Cannabis in Wiktionary, the free dictionary. ...


The steroids and sterols in animals are biologically produced from terpenoid precursors. Sometimes terpenoids are added to proteins, e.g. to enhance their attachment to the cell membrane; this is known as isoprenylation. Steroid skeleton of lanosterol. ... Sterols, or steroid alcohols are a subgroup of steroids with a hydroxyl group in the 3-position of the A-ring. ... A representation of the 3D structure of myoglobin, showing coloured alpha helices. ... Illustration of a cell membrane The cell membrane, also called the plasma membrane or plasmalemma, is a semipermeable lipid layer surrounding the cytoplasm of all living cells. ... Prenylation or isoprenylation is the addition of hydrophobic molecules to a protein to facilitate its attachment to the cell membrane. ...

Contents

Structure and classification

Terpenes are hydrocarbons resulting from the combination of several isoprene units. Terpenoids can be thought of as modified terpenes, where methyl groups have been moved or removed, or oxygen atoms added. (Some authors use the term "terpene" more broadly, to include the terpenoids.) Just like terpenes, the terpenoids can be classified according to the number of isoprene units used: Many terpenes are derived from conifer resins, here a pine. ... Hydrocarbons are refined at oil refineries and processed at chemical plants A hydrocarbon is a chemical compound that consists only of the elements carbon (C) and hydrogen (H). ... Isoprene is a common synonym for the chemical compound 2-methyl-1,3-butadiene. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... General Name, Symbol, Number oxygen, O, 8 Chemical series Nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Atomic mass 15. ...

  • Monoterpenoids, 2 isoprene units
  • Sesquiterpenoids, 3 isoprene units
  • Diterpenoids, 4 isoprene units
  • Sesterterpenoids, 5 isoprene units
  • Triterpenoids, 6 isoprene units
  • Tetraterpenoids, 8 isoprene units
  • Polyterpenoids with a larger number of isoprene units

Terpenoids can also be classified according to the number of cyclic structures they contain.


Biosynthesis

There are two metabolic pathways of creating terpenoids: In biochemistry, a metabolic pathway is a series of chemical reactions occurring within a cell, catalyzed by enzymes, resulting in either the formation of a metabolic product to be used or stored by the cell, or the initiation of another metabolic pathway (then called a flux generating step). ...


Mevalonic acid pathway

Many organisms manufacture terpenoids through the HMG-CoA reductase pathway, the pathway that also produces cholesterol. The reactions take place in the cytosol. The pathway was discovered in the 1950s. The HMG-CoA reductase pathway, also known as MVA pathway or mevalonate-dependent (MAD) route, is an important cellular metabolic pathway present in virtually all organisms. ... Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. ... The cytosol (cf. ... // Recovering from World War II and its aftermath, the economic miracle emerged in West Germany and Italy. ...


MEP/DOXP pathway

The 2-C-methyl-D-erythritol 4-phosphate/1-deoxy-D-xylulose 5-phosphate pathway (MEP/DOXP pathway), also known as non-mevalonate pathway or mevalonic acid independent pathway, takes place in the plastids of plants and apicomplexan protozoa as well as in many bacteria. It was discovered in the late 1980s. Mevalonic acid is a key organic compound in biochemistry. ... Plastids are major organelles found in plants and algae. ... Classes & Subclasses Aconoidasida Haemosporasina Piroplasmasina Blastocystea Conoidasida Coccidiasina Gregarinasina The Apicomplexa are a large group of protozoa, characterized by the presence of a unique organelle called an apical complex. ... Phyla Actinobacteria Aquificae Chlamydiae Bacteroidetes/Chlorobi Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Lentisphaerae Nitrospirae Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Verrucomicrobia Bacteria (singular: bacterium) are unicellular microorganisms. ...


Pyruvate and glyceraldehyde 3-phosphate are converted by DOXP synthase (Dxs) to 1-deoxy-D-xylulose 5-phosphate, and by DOXP reductase (Dxr, IspC) to 2-C-methyl-D-erythritol 4-phosphate (MEP). The subsequent three reaction steps catalyzed by 4-diphosphocytidyl-2-C-methyl-D-erythritol synthase (YgbP, IspD), 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase (YchB, IspE), and 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase (YgbB, IspF) mediate the formation of 2-C-methyl-D-erythritol 2,4-cyclopyrophosphate (MEcPP). Finally, MEcPP is converted to (E)-4-hydroxy-3-methyl-but-2-enyl pyrophosphate (HMB-PP) by HMB-PP synthase (GcpE, IspG), and HMB-PP is converted to isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP) by HMB-PP reductase (LytB, IspH). Pyruvate (CH3COCOO−) is the ionized form of pyruvic acid. ... G3P (structure) Glyceraldehyde 3-phosphate (G3P) is an intermediate in both glycolysis and gluconeogenesis. ... Chemical structure of isopentenyl pyrophosphate. ... Structure of dimethyallyl pyrophosphate Dimethylallyl pyrophosphate (or -diphosphate) (DMAPP) is an intermediate product of both mevalonic acid (MVA) pathway and DOXP/MEP pathway. ...


IPP and DMAPP are the end products in either pathway, and are the precursors of isoprene, monoterpenoids (10-carbon), diterpenoids (20-carbon), carotenoids (40-carbon), chlorophylls and plastoquinone-9 (45-carbon). Synthesis of all higher terpenoids proceeds via formation of geranyl pyrophosphate (GPP), farnesyl pyrophosphate (FPP), and geranylgeranyl pyrophosphate (GGPP). Isoprene is a common synonym for the chemical compound 2-methyl-1,3-butadiene. ... Carotenoids are organic pigments that are naturally occurring in plants and some other photosynthetic organisms like algae, some types of fungus and some bacteria. ... Chlorophyll gives leaves their green color Space-filling model of the chlorophyll molecule Chlorophyll is a green photosynthetic pigment found in most plants, algae, and cyanobacteria. ... Plastoquinone Plastoquinone, often abbreviated pq, is a molecule used in the electron transport chain in the light-dependent reactions of photosynthesis. ... Chemical structure of geranyl pyrophosphate. ... Chemical structure of farnesyl pyrophosphate. ... Chemical structure of geranylgeranyl pyrophosphate. ...


Although both pathways, MVA and MEP, are mutually exclusive in most organisms, interactions between them have been reported in plants and few bacteria species. u fuck in ua ... Phyla Actinobacteria Aquificae Chlamydiae Bacteroidetes/Chlorobi Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Lentisphaerae Nitrospirae Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Verrucomicrobia Bacteria (singular: bacterium) are unicellular microorganisms. ...

Organism Pathways
Eubacteria MVA or MEP
Archaea MVA
Green Algae MEP
Plants MVA and MEP
Animals MVA
Fungi MVA

Subgroups Actinobacteria Aquificae Bacteroidetes/Chlorobi Chlamydiae/Verrucomicrobia Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Nitrospirae Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Bacteria (singular: bacterium) are microscopic, unicellular organisms. ... Phyla / Classes Phylum Crenarchaeota Phylum Euryarchaeota     Halobacteria     Methanobacteria     Methanococci     Methanopyri     Archaeoglobi     Thermoplasmata     Thermococci Phylum Korarchaeota Phylum Nanoarchaeota Archaea (; from Greek αρχαία, ancient ones; singular Archaeum, Archaean, or Archaeon), also called Archaebacteria (), is a major division of living organisms. ... A seaweed (Laurencia) up close: the branches are multicellular and only about 1 mm thick. ... Divisions Green algae Chlorophyta Charophyta Land plants (embryophytes) Non-vascular plants (bryophytes) Marchantiophyta - liverworts Anthocerotophyta - hornworts Bryophyta - mosses Vascular plants (tracheophytes) †Rhyniophyta - rhyniophytes †Zosterophyllophyta - zosterophylls Lycopodiophyta - clubmosses †Trimerophytophyta - trimerophytes Pteridophyta - ferns and horsetails Seed plants (spermatophytes) †Pteridospermatophyta - seed ferns Pinophyta - conifers Cycadophyta - cycads Ginkgophyta - ginkgo Gnetophyta - gnetae Magnoliophyta - flowering plants... Animalia redirects here. ... Divisions Chytridiomycota Zygomycota Ascomycota Basidiomycota The Fungi (singular: fungus) are a large group of organisms ranked as a kingdom within the Domain Eukaryota. ...

See also

Pharmacology (in Greek: pharmacon (φάρμακον) meaning drug, and logos (λόγος) meaning science) is the study of how substances interact with living organisms to produce a change in function. ...

External link

  • IUPAC nomenclature of terpenoids
  • Links to external chemical sources

  Results from FactBites:
 
Terpenoid - Wikipedia, the free encyclopedia (417 words)
The terpenoids, sometimes referred to as isoprenoids, are a large and diverse class of naturally occurring organic chemicals similar to terpenes, derived from five-carbon isoprene units assembled and modified in thousands of ways.
Terpenoids contribute to the scent of eucalyptus, the flavors of cinnamon, cloves and ginger and the color of yellow flowers.
Terpenoids can be thought of as modified terpenes, where methyl groups have been moved or removed, or oxygen atoms added.
911. Esters/branched-chain terpenoid alc./aliphatic acyclic lin./B-C carb. acids (WHO Food Additives Series 40) (5935 words)
Terpenoid esters are principal flavour components of citrus and citrus peel oils, and have also been detected in wide variety of other fruits, spices and vegetables.
The terpenoid esters are usually found at concentration of < 1 mg/kg in citrus fruit juices, < 20 000 mg/kg in citrus peel oils, and < 50 000 mg/kg in spices (CIVO-TNO, 1994).
The terpenoid alcohols are expected to undergo omega-oxidation and functional group oxidation to yield polar metabolites which are excreted as the glucuronic acid conjugate in the urine.
  More results at FactBites »

 
 

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