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Terpenoid

From Wikipedia, the free encyclopedia

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.[1] When combined with the hydrocarbon terpenes, terpenoids comprise about 80,000 compounds.[2] They are the largest class of plant secondary metabolites, representing about 60% of known natural products.[3] Many terpenoids have substantial pharmacological bioactivity and are therefore of interest to medicinal chemists.[4]

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.[5] Well-known terpenoids include citral, menthol, camphor, salvinorin A in the plant Salvia divinorum, ginkgolide and bilobalide found in Ginkgo biloba and the cannabinoids found in cannabis. The provitamin beta carotene is a terpene derivative called a carotenoid.

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. Terpenoids play a role in plant defense as prophylaxis against pathogens and attractants for the predators of herbivores.[6]

Structure and classification

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Terpenoids are modified terpenes,[7] wherein 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 that comprise the parent terpene:

Terpenoids Analogue terpenes Number of isoprene units Number of carbon atoms General formula Examples[8]
Hemiterpenoids Isoprene 1 5 C5H8 DMAPP, isopentenyl pyrophosphate, isoprenol, isovaleramide, isovaleric acid, HMBPP, prenol
Monoterpenoids Monoterpenes 2 10 C10H16 Bornyl acetate, camphor, carvone, citral, citronellal, citronellol, geraniol, eucalyptol, hinokitiol, iridoids, linalool, menthol, thymol
Sesquiterpenoids Sesquiterpenes 3 15 C15H24 Farnesol, geosmin, humulone
Diterpenoids Diterpenes 4 20 C20H32 Abietic acid, ginkgolides, paclitaxel, retinol, salvinorin A, sclareol, steviol
Sesterterpenoids Sesterterpenes 5 25 C25H40 Andrastin A, manoalide
Triterpenoids Triterpenes 6 30 C30H48 Amyrin, betulinic acid, limonoids, oleanolic acid, sterols, squalene, ursolic acid
Tetraterpenoids Tetraterpenes 8 40 C40H64 Carotenoids
Polyterpenoid Polyterpenes >8 >40 (C5H8)n Gutta-percha, natural rubber

Terpenoids can also be classified according to the type and number of cyclic structures they contain: linear, acyclic, monocyclic, bicyclic, tricyclic, tetracyclic, pentacyclic, or macrocyclic.[8] The Salkowski test can be used to identify the presence of terpenoids.[9]

Biosynthesis

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Further information: Terpene § Biosynthesis

Terpenoids, at least those containing an alcohol functional group, often arise by hydrolysis of carbocationic intermediates produced from geranyl pyrophosphate. Analogously hydrolysis of intermediates from farnesyl pyrophosphate gives sesquiterpenoids, and hydrolysis of intermediates from geranylgeranyl pyrophosphate gives diterpenoids, etc.[10]

Impact on aerosols

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In air, terpenoids are converted into various species, such as aldehydes, hydroperoxides, organic nitrates, and epoxides[11] by short-lived free radicals (like the hydroxyl radical) and to a lesser extent by ozone.[12] These new species can dissolve into water droplets and contribute to aerosol and haze formation.[13] Secondary organic aerosols formed from this pathway may have atmospheric impacts.[14]

As an example the Blue Ridge Mountains in the U.S. and Blue Mountains of New South Wales in Australia are noted for having a bluish color when seen from a distance. Trees put the "blue" in Blue Ridge, from their terpenoids released into the atmosphere.[15][16][17]

See also

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References

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  1. ^ Chemistry, International Union of Pure and Applied. IUPAC Compendium of Chemical Terminology. IUPAC. doi:10.1351/goldbook.T06279.
  2. ^ Christianson, David W. (2017). "Structural and Chemical Biology of Terpenoid Cyclases". Chemical Reviews. 117 (17): 11570–11648. doi:10.1021/acs.chemrev.7b00287. PMC 5599884. PMID 28841019.
  3. ^ Firn R (2010). Nature's Chemicals. Oxford: Biology.
  4. ^ Ashour, Mohamed; Wink, Michael; Gershenzon, Jonathan (2010). "Biochemistry of Terpenoids: Monoterpenes, Sesquiterpenes and Diterpenes". Biochemistry of Plant Secondary Metabolism. pp. 258–303. doi:10.1002/9781444320503.ch5. ISBN 9781444320503.
  5. ^ Specter M (September 28, 2009). "A Life of Its Own". The New Yorker.
  6. ^ Singh, Bharat; Sharma, Ram A. (April 2015). "Plant terpenes: defense responses, phylogenetic analysis, regulation and clinical applications". 3 Biotech. 5 (2): 129–151. doi:10.1007/s13205-014-0220-2. ISSN 2190-572X. PMC 4362742. PMID 28324581.
  7. ^ Houghton, Isaac. "The Physiology of Cannabis Terpenes and Terpenoids – A Brief Overview". Elliot Barker. Retrieved 3 May 2016.
  8. ^ a b Ludwiczuk, A.; Skalicka-Woźniak, K.; Georgiev, M.I. (2017). "Terpenoids". Pharmacognosy: 233–266. doi:10.1016/B978-0-12-802104-0.00011-1. ISBN 9780128021040.
  9. ^ Ayoola GA (2008). "Phytochemical Screening and Antioxidant Activities of Some Selected Medicinal Plants Used for Malaria Therapy in Southwestern Nigeria". Tropical Journal of Pharmaceutical Research. 7 (3): 1019–1024. doi:10.4314/tjpr.v7i3.14686. hdl:1807/60332.
  10. ^ Davis, Edward M.; Croteau, Rodney (2000). "Cyclization Enzymes in the Biosynthesis of Monoterpenes, Sesquiterpenes, and Diterpenes". Topics in Current Chemistry. 209: 53–95. doi:10.1007/3-540-48146-X_2. ISBN 978-3-540-66573-1.
  11. ^ Organic Carbon Compounds Emitted By Trees Affect Air Quality, ScienceDaily, Aug. 7, 2009
  12. ^ IUPAC Subcommittee on Gas Kinetic Data Evaluation – Data Sheet Ox_VOC7, 2007
  13. ^ A source of haze, ScienceNews, August 6, 2009
  14. ^ D'Ambro, Emma L.; Schobesberger, Siegfried; Gaston, Cassandra J.; Lopez-Hilfiker, Felipe D.; Lee, Ben H.; Liu, Jiumeng; Zelenyuk, Alla; Bell, David; Cappa, Christopher D.; Helgestad, Taylor; Li, Ziyue (2019-09-05). "Chamber-based insights into the factors controlling epoxydiol (IEPOX) secondary organic aerosol (SOA) yield, composition, and volatility". Atmospheric Chemistry and Physics. 19 (17): 11253–11265. Bibcode:2019ACP....1911253D. doi:10.5194/acp-19-11253-2019. hdl:10138/305801. ISSN 1680-7316.
  15. ^ Johnson AW (1998). Invitation To Organic Chemistry. Jones & Bartlett Learning. p. 261. ISBN 978-0-7637-0432-2. blue mountains chemical terpene.
  16. ^ "Blue Ridge Parkway, Frequently Asked Questions". National Park Service. 2007. Archived from the original on December 28, 2007. Retrieved December 29, 2007.
  17. ^ CSIRO. "Beating the eucalypt blues – new ways to model air quality". www.csiro.au. Retrieved 2023-12-10.
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