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sesquiterpene wikipedia jump to content main menu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 biosynthesis and examples toggle biosynthesis and examples subsection 1 1 sesquiterpenoids 2 references 3 external links toggle the table of contents sesquiterpene 21 languages català čeština ελληνικά español euskara suomi français galego bahasa indonesia italiano 日本語 македонски polski português română русский srpskohrvatski српскохрватски српски srpski українська tiếng việt 中文 edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia class of terpenes big sagebrush artemisia tridentata contains sesquiterpene lactones which are sesquiterpenoids built from three isoprene units and contain a lactone ring hence the name these compounds are found in many other plants and can cause allergic reactions and toxicity if consumed in excess particularly in grazing livestock phallus indusiatus in cooktown queensland australia which produces two unique sesquiterpenes sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula c 15 h 24 like monoterpenes sesquiterpenes may be cyclic or contain rings including many combinations biochemical modifications such as oxidation or rearrangement produce the related sesquiterpenoids 1 it is estimated 2006 that 3000 sesquiterpenes have been identified 2 biosynthesis and examples edit the reaction of geranyl pyrophosphate with isopentenyl pyrophosphate results in the 15 carbon farnesyl pyrophosphate fpp which is an intermediate in the biosynthesis of sesquiterpenes such as farnesene 3 4 farnesyl pyrophosphate precursor to all sesquiterpenes cyclic sesquiterpenes are more common than cyclic monoterpenes because of the increased chain length and additional double bond in the sesquiterpene precursors in addition to common six membered ring systems such as the ones found in zingiberene and bisacurone cyclization of one end of the chain to the other end can lead to macrocyclic rings such as humulene selected sesquiterpenes and sesquiterpenoids longifolene found in terpentine zingiberene abundant in ginger δ cadinene found in cade juniper humulene found in hops 5 caryophyllene which is pervasive but especially in cloves the cadinenes contain two fused six membered rings caryophyllene a component of many essential oils such as clove oil contains a nine membered ring fused to a cyclobutane ring rishitin is another example of a cadinene which is found in potatoes and tomatoes 6 7 vetivazulene and guaiazulene are aromatic bicyclic sesquiterpenoids with the addition of a third ring the possible structures become increasingly varied examples include longifolene copaene and the alcohol patchoulol sesquiterpenoids edit the fpp backbone can be rearranged in several different ways and further decorated with different functional groups hence the large variety of sesquiterpenoids geosmin the volatile compound that gives an earthy taste and musty odor in drinking water and the characteristic odor on a rainy day is a sesquiterpenoid produced by bacteria especially cyanobacteria that are present in the soils and water supplies 8 oxidation of farnesene then provides the sesquiterpenoid farnesol sesquiterpene lactones are a common class of sesquiterpenoids that contain a lactone ring hence the name they are found in many plants and can cause allergic reactions and toxicity if consumed excessively particularly in grazing livestock 9 the term merosesquiterpenoids was coined in 1968 to describe molecules of this class that have a mixed biosynthetic origin meaning isoprenoid precursors like isopentenyl pyrophosphate are derived from both the mevalonate and non mevalonate pathways 10 references edit eberhard breitmaier 2006 sesquiterpenes terpenes flavors fragrances pharmaca pheromones pp 24 51 doi 10 1002 9783527609949 ch3 isbn 9783527609949 sell charles s 2006 terpenoids kirk othmer encyclopedia of chemical technology doi 10 1002 0471238961 2005181602120504 a01 pub2 isbn 0471238961 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 cite journal cs1 maint periodical has isbn link chizzola r 2013 regular monoterpenes and sesquiterpenes essential oils natural products springer berlin heidelberg pp 2973 3008 doi 10 1007 978 3 642 22144 6_130 isbn 9783642221439 schönberger c kostelecky t 16 may 2012 125th anniversary review the role of hops in brewing journal of the institute of brewing 117 3 259 doi 10 1002 j 2050 0416 2011 tb00471 x katsui n murai a takasugi m imaizumi k masamune t tomiyama k 1968 the structure of rishitin a new antifungal compound from diseased potato tubers chemical communications 1 43 44 doi 10 1039 c19680000043 d harlingue a mamdouh a m malfatti p soulie m c bompeix g 1995 evidence for rishitin biosynthesis in tomato cultures phytochemistry 39 1 69 70 https doi org 10 1016 0031 9422 94 00844 j izaguirre g taylor wd june 1995 geosmin and 2 methylisoborneol production in a major aqueduct system water science and technology 31 11 41 48 doi 10 1016 0273 1223 95 00454 u sesquiterpene lactones and their toxicity to livestock cornell cals cornell university retrieved december 29 2018 simpson thomas j ahmed salman a rupert mcintyre c scott fiona e sadler ian h 1997 03 17 biosynthesis of polyketide terpenoid meroterpenoid metabolites andibenin b and andilesin a in aspergillus variecolor tetrahedron 53 11 4013 4034 doi 10 1016 s0040 4020 97 00015 x issn 0040 4020 external links edit look up sesquiterpene in wiktionary the free dictionary sesquiterpenes at the u s national library of medicine medical subject headings mesh v t e types of terpenes and terpenoids of isoprene units basic forms acyclic linear cis and trans forms monocyclic single ring bicyclic 2 rings iridoids cyclopentane ring iridoid glycosides iridoids bound to a sugar steroids 4 rings hemiterpenoids 1 isoprene c 5 h 8 prenol isovaleric acid monoterpenes c 10 h 16 2 acyclic ocimene myrcenes monocyclic limonene terpinene phellandrene bicyclic pinene α and β camphene thujene sabinene carene monoterpenoids 2 modified acyclic citronellal citral citronellol geraniol geranyl pyrophosphate halomon linalool monocyclic achilleol a grapefruit mercaptan menthol p cymene thujaplicins hinokitiol thymol perillyl alcohol carvacrol bicyclic camphor borneol bornyl acetate eucalyptol ascaridole umbellulone sesquiterpenoids 3 artemisinin bisabolol cadinene cadinol cedrene chanootin farnesyl pyrophosphate juniperol longifolene muurolene nootkatin diterpenoids 4 acyclic phytol geranylgeranyl pyrophosphate geranyl linalool monocyclic retinol retinal bicyclic cis abienol epimanool salvinorin a tricyclic cembrene forskolin manoyl oxide pimaral pimarol tetracyclic aphidicolin gibberellin paclitaxel resin acids abietic acid communic acid dehydroabietic acid isopimaric acid lambertianic acid levopimaric acid mercusic acid neoabietic acid pimaric acid sandaracopimaric acid secodehydroabietic acid palustric acid sesterterpenoids 5 geranylfarnesol triterpenoids 6 steroids phytosterols campesterol citrostadienol cycloartenol sitostanol sitosterol stigmasterol tocopherols cholesterol testosterone cholecalciferol ecdysones other betulin euphol lanosterol madecassoside saponins serratenediol squalane acids oleanolic acid ursolic acid betulinic acid moronic acid madecassic acid zizyberenalic acid sesquarterpenes oids 7 ferrugicadiol tetraprenylcurcumene tetraterpenoids carotenoids 8 carotenes alpha carotene beta carotene gamma carotene delta carotene lycopene neurosporene phytofluene phytoene xanthophylls canthaxanthin cryptoxanthin zeaxanthin astaxanthin lutein rubixanthin polyterpenoids many natural rubber gutta percha gutta balatá norisoprenoids modified 3 oxo α ionol 7 8 dihydroionone synthesis terpene synthase enzymes many having in common a terpene synthase n terminal domain protein domain activated isoprene forms isopentenyl pyrophosphate ipp dimethylallyl pyrophosphate dmapp retrieved from https en wikipedia org w index php title sesquiterpene oldid 1360735392 category sesquiterpenes hidden categories articles with short description short description is different from wikidata cs1 maint periodical has isbn this page was last edited on 23 june 2026 at 07 42 utc page was rendered with parsoid text is available under the creative commons attribution sharealike 4 0 license additional terms may apply by using this site you agree to the terms of use and privacy policy wikipedia is a registered trademark of the wikimedia foundation inc a non profit organization privacy policy about wikipedia disclaimers contact wikipedia legal safety contacts code of conduct developers statistics cookie statement mobile view search search toggle the table of contents sesquiterpene 21 languages add topic