Image Isopentenyl pyrophosphate.svg thumb 250px Chemical structure of the terpenoid isopentenyl pyrophosphate The terpenoids IPAc en icon t r p n d respell TUR p noyd , sometimes called isoprenoids , are a large and diverse class of naturally occurring organic compound organic chemicals similar to terpene s, derived from five carbon isoprene units assembled and modified in thousands of ways. Most are multicyclic structures that differ from one another not only in functional group s but also in their basic carbon skeletons. These lipid s can be found in all classes of living things, and are the largest group of natural products. Plant terpenoids are used extensively for their aromatic qualities. They play a role in traditional herbal remedies and are under investigation for antibacterial , antineoplastic , and other pharmaceutical functions. 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 . ref Cite journal url http www.newyorker.com reporting 2009 09 28 090928fa fact specter?currentPage all work The New Yorker title A Life of Its Own author Michael Specter date September 28, 2009 ref Well known terpenoids include citral , menthol , camphor , salvinorin A in the plant Salvia divinorum , and the cannabinoid s found in Cannabis . The steroid s and sterol s in animals are biologically produced from terpenoid precursors. Sometimes terpenoids are added to protein s, e.g., to enhance their attachment to the cell membrane this is known as isoprenylation . Many of these are Substrate biochemistry substrate s for plant Cytochrome P450 . Structure and classification ..., having a partial terpenoid structure Biosynthesis Image Sterol synthesis.svg thumb right 350px Simplified version of the steroid synthesis pathway with the terpenoid intermediates isopentenyl pyrophosphate ... fr Terp no de it Terpeni ja pl Terpenoidy ru sr Terpenoid fi Terpenoidi zh ... more details
Merge to Tetraterpene date February 2012 Tetraterpenoids are terpenoid s of 8 isoprene units hence 40 carbon atoms in the skeleton. carotenoid s Others trianthenol 1 methyl tortuoate C from coral ref http www.informaworld.com smpp content db all content a779551258 ref References Reflist Category Terpenes and terpenoids Chem stub ... more details
Hydrocarbon plants or petroleum plants are plants which produce terpenoid s as secondary metabolite s in sufficient quantities to make it economically feasible to convert their dry mass to gasoline like fuels. Nobel laureate Melvin Calvin has studied the terpenoid terpene biosynthetic pathway s of a number of species of plants to study and quantify this property in various species. Species include latex producing members of the Euphorbiaceae family that cannot be tapped for their liquid latex such as Euphorbia lathyris and Euphorbia tirucalli E. tirucalli . ref name Kalita2008 cite journal last1 Kalita first1 D title Hydrocarbon plant New source of energy for future journal Renewable and Sustainable Energy Reviews volume 12 issue 2 year 2008 pages 455 471 issn 13640321 doi 10.1016 j.rser.2006.07.008 ref ref name Ramawat2010 cite book author K. G. Ramawat title Desert Plants Biology and Biotechnology url http books.google.com books?id UNaNWN4zkqQC&pg PA37 accessdate 23 August 2010 year 2010 publisher Springer isbn 9783642025495 pages 37 ref See also Biogasoline Energy crop Asclepias References reflist bioenergy Category Biofuels material stub ... more details
Triterpenoids are terpenoid derviatives of triterpene molecules. They may have useful anti cancer properties. ref cite journal pages 1549 60 doi 10.1055 s 0029 1186102 title Pentacyclic Triterpenes of the Lupane, Oleanane and Ursane Group as Tools in Cancer Therapy year 2009 last1 Laszczyk first1 Melanie journal Planta Medica volume 75 issue 15 pmid 19742422 ref Notable examples Betulinic acid , possible anti cancer drug Bardoxolone methyl , inflammation modulator Triterpenoid saponins References Reflist Category Terpenes and terpenoids Organic chem stub ... more details
Unreferenced date February 2007 Irones are a group of ionone methylionone odorants used in perfumery , derived from Iris plant iris oil, e.g. orris root . The most commercially important of these are cis irone, and cis irone Irones form through slow oxidation of terpenoid triterpenoids in dried rhizome s of the Iris plant iris species, Iris plant Iris pallida . Irones typically have a sweet floral, iris, woody, ionone , odor. Category Perfume ingredients Category Aromatic compounds fr Irone pl Irony ... more details
Perilla may refer to any of the following subjects Perilla a genus of plants Perilla frutescens an edible herb commonly known as Perilla Perilla pet name of Caecilia Metella daughter of Metellus Celer , given by her lover Ticida Perilla restaurant a New York City based restaurant owned by Harold Dieterle Perilla spider Perilla spider a spider genus Perilla aldehyde perillaldehyde , a flavoring Perilla de Castro a municipality located in Spain Perilla ketone a natural terpenoid Perilla Mountains a mountain range in Cochise County, Arizona Perilla oil oil from the seeds of plants of the genus Perilla Perilla sugar perillartine , a sweetener See also Parilla Parrilla disambiguation disambig ... more details
distinguish2 Luteone terpenoid , a twenty three carbon terpenoid from the dorid nudibranch Cadlina luteomarginata chembox verifiedrevid 401016000 Name Luteone ImageFile Luteone.PNG ImageSize 200px ImageName Chemical structure of luteone IUPACName 3 2,4 dihydroxyphenyl 5,7 dihydroxy 6 3 methylbut 2 enyl chromen 4 one OtherNames Ruizgenin br Section1 Chembox Identifiers CASNo 41743 56 0 CASNo Ref CASOther PubChem 5281797 SMILES CC CCC1 C C C2C C1O C O C CO2 C3 C C C C C3 O O O C InChI MeSHName Section2 Chembox Properties Formula C sub 20 sub H sub 18 sub O sub 6 sub MolarMass 354.35 g mol ExactMass 354.110338 u Appearance Density MeltingPt C BoilingPt C Solubility Luteone is a prenyl ated isoflavone , a type of flavonoid. It can be found in the pods of Laburnum anagyroides ref http cat.inist.fr ?aModele afficheN&cpsidt 3619889 Isoflavones from pods of Laburnum anagyroides. Sato H., Tahara S., Ingham J. L. and Dziedzic S. Z., Phytochemistry, 1995, vol. 39, no3, pp. 673 676 ref and can be synthetized. ref http sciencelinks.jp j east article 200110 000020011001A0106511.php Regioselective Synthesis of Prenylisoflavones. Syntheses of Luteone and Luteone Hydrate. Tsukayama M., Wada H., Kishida M., Nishiuchi M. and Kawamura Y., Chem Lett, Vol. No. 12, pp 1362 1363 2000 ref References reflist isoflavone DEFAULTSORT Luteone Isoflavone Category Isoflavones Category Resorcinols natural phenol stub ... more details
Unreferenced date July 2009 chembox verifiedrevid 400332632 ImageFile Norpatchoulenol.png ImageSize 150px IUPACName OtherNames Section1 Chembox Identifiers InChI 1 C14H22O c1 12 2 10 6 8 13 3 11 9 10 5 4 7 14 12,13 15 h4 5,10 11,15H,6 9H2,1 3H3 t10?,11?,13 ,14? m0 s1 InChIKey OSQSDJNIURJARY QHNNHONCBN StdInChI Ref stdinchicite correct chemspider StdInChI 1S C14H22O c1 12 2 10 6 8 13 3 11 9 10 5 4 7 14 12,13 15 h4 5,10 11,15H,6 9H2,1 3H3 t10?,11?,13 ,14? m0 s1 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey OSQSDJNIURJARY QHNNHONCSA N CASNo ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 21106458 PubChem SMILES C C 31CCC2CC3 C C CC1 O C2 C C Section2 Chembox Properties Formula C sub 14 sub H sub 22 sub O MolarMass 206.33 g mol Appearance Density MeltingPt BoilingPt Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition Norpatchoulenol is a tricyclic terpenoid found in commercial patchouli extract in small quantities, and thought to contribute significantly to the aroma of patchouli oil. See also Patchoulol Category Sesquiterpenes ... more details
taxobox regnum Plant ae unranked divisio Angiosperms unranked classis Eudicots unranked ordo Rosids ordo Malpighiales familia Calophyllaceae genus Mammea species M. siamensis binomial Mammea siamensis binomial authority T. Anders. synonyms Ochrocarpus siamensis T. Anders. Mammea siamensis lang th , saraphi , soiphi in Southern Thai ref http www.tistr.or.th pharma Mammea 20siamensis.htm Mammea siamensis th icon ref is a species of flowering plant in the Calophyllaceae family. It grows as a tree and is found in Thailand . References reflist External links http www2.psu.ac.th PresidentOffice EduService Journal Thai Herbs pdf 12 terpenoid steroids.pdf A terpenoid and two steroids from the flowers of Mammea siamensis http article.pubs.nrc cnrc.gc.ca RPAS RPViewDoc? handler HandleInitialGet&articleFile v06 157.pdf&journal cjc&volume 84 Phenolic compounds from Mammea siamensis seeds Category Mammea siamensis Calophyllaceae stub th ... more details
italic title Taxobox name Cystoseira elegans image regnum Chromalveolata phylum Heterokont ophyta classis Brown algae Phaeophyceae ordo Fucales familia Fucaceae genus Cystoseira species C. elegans binomial Cystoseira elegans binomial authority C. Sauvageau Sauvageau , 1912 subdivision ranks Subspecies subdivision Cystoseira elegans is a brown alga species in the genus Cystoseira endemic to the Mediterranean. Hydroxylated di terpenoid hydroquinone s can be isolated from C. elegans . ref Hydroxylated diterpenoid hydroquinones from cystoseira elegans significant products or artifacts ? B. Banaigs, C. Francisco, E. Gonzalez, L. Comodier and William Fenical, Tetrahedron Letters, Volume 23, Issue 32, 1982, pages 3271 3272, doi 10.1016 S0040 4039 00 87589 9 ref References reflist External links wikispecies commons category http www.algaebase.org search species detail ?species id 1339 Cystoseira elegans on www.algaebase.org Category Fucales Category Plants described in 1912 alga stub ... more details
enzyme Name delta cadinene synthase EC number 4.2.3.13 CAS number 166800 09 5 IUBMB EC number 4 2 3 13 GO code 0047461 image width caption In enzymology , a delta cadinene synthase EC number 4.2.3.13 is an enzyme that catalysis catalyzes the chemical reaction 2 trans,6 trans farnesyl diphosphate math rightleftharpoons math delta cadinene diphosphate Hence, this enzyme has one substrate biochemistry substrate , 2 trans,6 trans farnesyl diphosphate , and two product chemistry products , delta cadinene and diphosphate . This enzyme belongs to the family of lyase s, specifically those carbon oxygen lyases acting on phosphates. The systematic name of this enzyme class is 2 trans,6 trans farnesyl diphosphate diphosphate lyase cyclizing, delta cadinene forming . This enzyme participates in terpenoid biosynthesis . It employs one cofactor biochemistry cofactor , magnesium . Delta cadinene synthase , a sesquiterpene cyclase , is an enzyme expressed in plants that catalysis catalyzes a cyclization reaction in terpenoid biosynthesis. The enzyme cyclizes farnesyl diphosphate to delta cadinene and releases pyrophosphate . Delta cadinene synthase is one of the key steps in the synthesis of gossypol , a toxic terpenoid produced in cotton seeds. Recently, cotton plants that stably underexpress the enzyme in seeds have been developed using RNA interference techniques, producing a plant that had been proposed as a rich source of protein in nutrition dietary protein for developing countries. ref name Sunilkumar Sunilkumar G, Campbell L, Puckhaber L, Stipanovic R, Rathore K 2006 . Engineering cottonseed for use in human nutrition by tissue specific reduction of toxic gossypol . Proc Natl Acad Sci U S A 103 48 18054 9. DOI 10.1073 pnas.0605389103 PMID 17110445 ref External links http www.brenda.uni koeln.de php result flat.php4?ecno 4.2.3.13 BRENDA entry http expasy.org uniprot P93665 SwissProt entry References reflist 1 cite journal author Chen XY, Chen Y, Heinstein P, Davisson VJ year ... more details
, annual review, volume 44, 2006 ref C. luteomarginata produces the twenty three carbon terpenoid Luteone terpenoid Luteone ref http www.sciencedirect.com science? ob ArticleURL& udi B6THS 42HXTSC ... three carbon terpenoid from the dorid nudi branch Cadlina luteomarginata. Jocelyne Hellou and Raymond ... more details
image ginkgolides structure.png thumb right Chemical structure of ginkgolides Ginkgolides are biologically active terpenoid terpenic lactone s present in Ginkgo biloba . They are diterpenoid s with 20 carbon skeletons, which are biosynthesized from geranylgeranyl pyrophosphate . ref cite journal title Structure and absolute configuration of ginkgolide B characterized by IR and VCD spectroscopy author Niels H. Andersen, Niels Johan Christensen, Peter R. Lassen, Teresa B.N. Freedman, Laurence A. Nafie, Kristian Str mgaard, Lars Hemmingsen doi 10.1002 chir.20730 journal Chirality volume 22 issue 2 pages 217 223 year February 2010 ref class wikitable ginkgolid R sup 1 sup R sup 2 sup R sup 3 sup A OH H H B OH OH H C OH OH OH J OH H OH M H OH OH Gingkolide B may be effective as preventive treatment in reducing migraine attack frequency. ref Usai S, Grazzi L, Bussone G Gingkolide B as migraine preventive treatment in young age results at 1 year follow up. Neurol Sci. 2011 May 32 Suppl 1 197 9 ref See also Bilobalide References Reflist 2 Category Lactones Category Diterpenes Organic compound stub de Ginkgolide ja sr Ginkgolid tr Ginkgolid vi Ginkgolit ... more details
refimprove date May 2008 Image Nasinov 9024.JPG right thumb Fanning honeybee exposes Nasonov gland white at tip of abdomen releasing pheromone to entice swarm into an empty hive The Nasonov alternatively, Nasanov pheromone honeybee pheromone is released by worker bee worker honeybee bees to orient returning forager bees back to the colony. To broadcast this scent, bees raise their abdomen s, which contain the Nasonov gland s, and fan their wing s vigorously. Nasonov includes a number of different terpenoid s including geraniol , nerolic acid , citral and geranic acid . Bees use these to find the entrance to their colony or hive, and they release them on flowers so other bees know which flowers have nectar. A synthetically produced Nasonov pheromone can be used to attract a Swarming honey bee honey bee swarm to an unoccupied beehive beekeeping hive or a swarm catching box. Synthetically produced Nasonov consists of citral and geraniol in a 2 1 ratio. References reflist DEFAULTSORT Nasonov Pheromone Category Beekeeping Category Insect ecology Category Insect pheromones Category Olfaction Bee stub de Nasanov Pheromon hu Naszonov feromon pl Gruczo Nasonowa sl Nasonov feromon sk Nasonov ferom n ... more details
Orphan date January 2011 File Agelasimine A.svg thumb 100px right Chemical structure of agelasimine A Agelasimines are a group of adenine related bicyclic terpenoid diterpenoids isolated from the orange sea sponge sponge Agelas mauritania . Their chemical structures are closely related to the agelasine s. Both groups of compounds display a range of biological activities, such as cytotoxicity, inhibition of adenosine transfer into rabbit erythrocyte s red blood cells , Ca sup 2 sup channel antagonistic action, Alpha 1 adrenergic receptor 1 adrenergic blockade and others. Both compounds have been reproduced in the laboratory by organic synthesis . References Fathi Afshar R Allen T M Krueger C A Cook D A Clanachan A S Vriend R Baer H P Cass C E, Canadian Journal of Physiology and Pharmacology , 1989, 67 4 , 276 81 Fathi Afshar, R. Allen, T. M., Canadian Journal of Chemistry , 1988, 66 1 , 45 50. Fathi Afshar, R. Allen, T. M. Krueger, C. A. Cook, D. A. Clanachan, A. S. Vriend, R. Baer, H. P. Cass, C. E., Canadian Journal of Physiology and Pharmacology , 1989, 67 4 , 276 81. Ohba, Masashi Iizuka, Kazuaki Ishibashi, Hiroyuki Fujii, Tozo., Tetrahedron journal Tetrahedron 1997, 53 50 , 16977 16986. Category Terpenes and terpenoids organic compound stub ... more details
chembox verifiedrevid 355904776 ImageFile Perilla ketone.png ImageSize 200px IUPACName 1 3 Furanyl 4 methyl 1 pentanone OtherNames beta Furyl isoamyl ketone Section1 Chembox Identifiers CASNo 553 84 4 PubChem 68381 SMILES CC C CCC C1 COC C1 O Section2 Chembox Properties C 10 H 14 O 2 MolarMass Appearance Liquid Density 0.9920 g cm MeltingPt 25 C BoilingPtC 196 Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition Perilla ketone is a natural terpenoid that consists of a furan ring with a six carbon side chain containing a ketone functional group. It is a colorless oil that is sensitive to oxygen, becoming colored upon standing. Perilla ketone is present in the leaves and seeds of purple mint Perilla frutescens , which is toxic to some animals. When cattle and horses consume purple mint when grazing in fields in which it grows, the perilla ketone causes pulmonary edema leading to a condition sometimes called perilla mint toxicosis. References http www.hort.purdue.edu newcrop proceedings1993 V2 322.html Perilla Botany, Uses and Genetic Resources Category Furans Category Ketones Category Monoterpenes ... more details
chembox verifiedrevid 428751289 ImageFile Carvonic acid.svg ImageSize 200px IUPACName 2 4 Methyl 5 oxo cyclohex 3 enyl acrylic acid OtherNames Section1 Chembox Identifiers CASNo Ref cascite correct ?? CASNo 362483 06 5 CASNo Comment racemate PubChem SMILES O C1CC C C O O C CC C1C Section2 Chembox Properties Formula C sub 10 sub H sub 12 sub O sub 3 sub MolarMass 180.20 g mol Appearance Density MeltingPt BoilingPt Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition Carvonic acid , or methylene 4 methyl 5 oxo 3 cyclohexene 1 acetic acid, is a terpenoid formed by metabolism of carvone in humans. ref cite journal author Engel, W. title In Vivo Studies on the Metabolism of the Monoterpenes S and R Carvone in Humans Using the Metabolism of Ingestion Correlated Amounts MICA Approach journal J. Agric. Food Chem. year 2001 volume 49 issue 8 pages 4069&ndash 4075 doi 10.1021 jf010157q ref References Reflist Category Carboxylic acids Category Monoterpenes Category Ketones ketone stub ja ... more details
Gustaf Komppa 1867 in Viipuri 20 January 1949 in Helsinki was a Finland Finnish chemist best known for a world first in commercializing total synthesis , that of camphor in 1903. Komppa was born in Viipuri in 1867. He graduated from the University of Helsinki in 1891 and subsequently worked for a while in Switzerland before obtaining his Ph.D. Shortly after returning to Finland he became the professor of chemistry at the Helsinki University of Technology . He was also a board member in several major Finnish corporations and a founding member of Finnish Academy of Science . Universities of Uppsala University Uppsala , Copenhagen and Heidelberg invited him as a honorary doctor . Komppa worked extensively with organic synthesis of several compounds, most notably camphor and terpenoid s. The camphor synthesis was an important breakthrough, especially because he proceeded to commercialize a semisynthesis from tall oil derived pinene . He also developed methods for converting peat into fuel. During his career Komppa published more than 200 research papers. References http www.kemia lehti.fi pdf gustafkomppa.pdf Article about Komppa in Finnish Persondata Metadata see Wikipedia Persondata . NAME Komppa, Gustaf ALTERNATIVE NAMES SHORT DESCRIPTION DATE OF BIRTH 1867 PLACE OF BIRTH DATE OF DEATH 20 January 1949 PLACE OF DEATH DEFAULTSORT Komppa, Gustaf Category 1867 births Category 1949 deaths Category Finnish scientists Category People from Vyborg Finland scientist stub eu Gustaf Komppa fi Gustaf Komppa ... more details
enzyme Name 6 endo hydroxycineole dehydrogenase EC number 1.1.1.241 CAS number 122933 68 0 IUBMB EC number 1 1 1 241 GO code 0045481 image width caption In enzymology , a 6 endo hydroxycineole dehydrogenase EC number 1.1.1.241 is an enzyme that catalysis catalyzes the chemical reaction 6 endo hydroxycineole NAD sup sup math rightleftharpoons math 6 oxocineole NADH H sup sup Thus, the two substrate biochemistry substrates of this enzyme are 6 endo hydroxycineole and nicotinamide adenine dinucleotide NAD sup sup , whereas its 3 product chemistry products are 6 oxocineole , nicotinamide adenine dinucleotide NADH , and hydrogen ion H sup sup . This enzyme belongs to the family of oxidoreductase s, specifically those acting on the CH OH group of donor with NAD or NADP as acceptor. The systematic name of this enzyme class is 6 endo hydroxycineole NAD 6 oxidoreductase . This enzyme participates in terpenoid biosynthesis . References reflist 1 cite journal author Williams DR, Trudgill PW and Taylor DG date 1989 title Metabolism of 1,8 cineole by Rhodococcus species ring cleavage reactions journal J. Gen. Microbiol. volume 135 pages 1957&ndash 1967 1.1.1 enzyme stub Category EC 1.1.1 Category NADH dependent enzymes Category Enzymes of unknown structure it 6 endo idrossicineolo deidrogenasi ja 6 endo ... more details
Infobox protein family Symbol DXP reductoisom Name 1 deoxy D xylulose 5 phosphate reductoisomerase image PDB 1q0q EBI.jpg width caption crystal structure of dxr in complex with the substrate 1 deoxy d xylulose 5 phosphate Pfam PF02670 Pfam clan CL0063 InterPro IPR013512 SMART PROSITE MEROPS SCOP 1onn TCDB OPM family OPM protein CAZy CDD Infobox protein family Symbol DXP redisom C Name 1 deoxy D xylulose 5 phosphate reductoisomerase C terminal image PDB 1q0q EBI.jpg width caption crystal structure of dxr in complex with the substrate 1 deoxy d xylulose 5 phosphate Pfam PF08436 Pfam clan CL0063 InterPro IPR013644 SMART PROSITE MEROPS SCOP TCDB OPM family OPM protein CAZy CDD DXP reductoisomerase or 1 deoxy d xylulose 5 phosphate reductoisomerase is an enzyme that intraconverts 1 deoxy D xylulose 5 phosphate and 2 C methyl D erythritol 4 phosphate . ref name pmid9707569 cite journal author Takahashi S, Kuzuyama T, Watanabe H, Seto H title A 1 deoxy D xylulose 5 phosphate reductoisomerase catalyzing the formation of 2 C methyl D erythritol 4 phosphate in an alternative nonmevalonate pathway for terpenoid biosynthesis journal Proc. Natl. Acad. Sci. U.S.A. volume 95 issue 17 pages 9879 84 year 1998 month August pmid 9707569 pmc 21430 doi 10.1073 pnas.95.17.9879 url ref gallery Image DOXP.png 1 Deoxy D xylulose 5 phosphate Image MEP.png 2 C methylerythritol 4 phosphate gallery It is classified under EC number 1.1.1.267 . It is part of the non mevalonate pathway , and it is inhibited by fosmidomycin . It is normally abbreviated DXR, but it is sometimes named IspC. This enzyme is responsible for terpenoid biosynthesis in some organism s. ref name pmid9707569 In Arabidopsis thaliana Arabidopsis thaliana 1 deoxy D xylulose 5 phosphate reductoisomerase is the first committed enzyme of the non mevalonate pathway for isoprenoid biosynthesis. The enzyme requires Manganese Mn2 , Cobalt Co2 or Magnesium Mg2 for activity, with Mn2 being most effective. External links MeshName DXP red ... more details
Image Strigolactones general chemical structure.png 200px thumb General chemical structure and numbering scheme of strigolactones Strigolactones are plant hormones that have been implicated in inhibition of shoot branching. ref cite journal author Gomez Roldan V, Fermas S, Brewer PB, Puech Pag s V, Dun EA, Pillot JP, Letisse F, Matusova R, Danoun S, Portais JC, Bouwmeester H, B card G, Beveridge CA, Rameau C, Rochange SF year 2008 title Strigolactone inhibition of shoot branching journal Nature volume 455 issue 7210 pages 180 194 pmid 18690209 doi 10.1038 nature07271 ref ref cite journal author Umehara M, Hanada A, Yoshida S, Akiyama K, Arite T, Takeda Kamiya N, Magome H, Kamiya Y, Shirasu K, Yoneyama K, Kyozuka J, Yamaguchi S year 2008 title Inhibition of shoot branching by new terpenoid plant hormones journal Nature volume 455 issue 7210 pages 195 200 pmid 18690207 doi 10.1038 nature07272 ref Strigolactones are carotenoid derived and trigger germination of parasitic plant seeds for example Striga plant Striga from which they gained their name and stimulate symbiotic mycorrhiza mycorrhizal fungi. ref cite journal author Kohki Akiyama, Hideo Hayashi year 2006 title Strigolactones Chemical Signals for Fungal Symbionts and Parasitic Weeds in Plant Roots journal Annals of Botany volume 97 issue 6 pages 925 931 pmid 16574693 doi 10.1093 aob mcl063 url pmc 2803390 ref Strigolactones contain a labile ether bond that is easily hydrolyzed in the rhizosphere meaning that there is a large concentration gradient between areas near the root and those further away. Chemistry Strigolactones are terpenoid lactone s and are derived from carotenoid s. Image Strigol chemical structure.png 150px Chemical structure and numbering of strigol Image Strigyl acetate chemical structure.png 150px Chemical structure and numbering of strigyl acetate align center Strigol Strigyl acetate Image Orobanchol chemical structure.png 150px Chemical structure and numbering of orobanchol Image Orobanchyl ... more details
chembox Verifiedfields changed verifiedrevid 461119902 ImageFile Geranyl pyrophosphate.png ImageSize 220px ImageName Skeletal formula ImageFile1 Geranyl pyrophosphate 3D balls.png ImageSize1 240px ImageName1 Ball and stick model IUPACName OtherNames Section1 Chembox Identifiers ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 393471 InChI 1 C10H20O7P2 c1 9 2 5 4 6 10 3 7 8 16 19 14,15 17 18 11,12 13 h5,7H,4,6,8H2,1 3H3, H,14,15 H2,11,12,13 b10 7 InChIKey GVVPGTZRZFNKDS JXMROGBWBE StdInChI Ref stdinchicite correct chemspider StdInChI 1S C10H20O7P2 c1 9 2 5 4 6 10 3 7 8 16 19 14,15 17 18 11,12 13 h5,7H,4,6,8H2,1 3H3, H,14,15 H2,11,12,13 b10 7 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey GVVPGTZRZFNKDS JXMROGBWSA N CASNo Ref cascite changed ?? CASNo 763 10 0 ChEMBL Ref ebicite correct EBI ChEMBL 41342 PubChem 445995 DrugBank Ref drugbankcite correct drugbank DrugBank DB02552 ChEBI Ref ebicite correct EBI ChEBI 17211 SMILES O P O O OP O OC C C CC C C C C C O MeSHName Geranyl pyrophosphate Section2 Chembox Properties Formula C sub 10 sub H sub 20 sub O sub 7 sub P sub 2 sub MolarMass 314.209 Appearance Density MeltingPt BoilingPt Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition Geranyl pyrophosphate is an intermediate in the HMG CoA reductase pathway used by organisms in the biosynthesis of farnesyl pyrophosphate , geranylgeranyl pyrophosphate , cholesterol , terpene s and terpenoid s. Image Sterol synthesis.svg thumb center 350px Simplified version of the steroid synthesis pathway with the intermediates isopentenyl pyrophosphate IPP , dimethylallyl pyrophosphate DMAPP , geranyl pyrophosphate GPP and squalene shown. Some intermediates are omitted. Related compounds Geraniol Farnesyl pyrophosphate Geranylgeranyl pyrophosphate See also Dimethylallyltranstransferase References reflist Cholesterol metabolism intermediates Category Organophosphates Category Monoterpenes biochem stub de Geranylpyrophosphat es Pirofosfato de ger ... more details
Unreferenced stub auto yes date December 2009 Chembox verifiedrevid 424660305 ImageFile Farnesyl pyrophosphate.png ImageSize 220px ImageName Skeletal formula ImageFile1 Farnesyl pyrophosphate 3D balls.png ImageSize1 250px ImageName1 Ball and stick model IUPACName OtherNames Section1 Chembox Identifiers CASNo Ref cascite correct ?? CASNo 13058 04 3 PubChem 706 SMILES MeSHName farnesyl pyrophosphate Section2 Chembox Properties Formula C sub 15 sub H sub 28 sub O sub 7 sub P sub 2 sub MolarMass 382.326 Appearance Density MeltingPt BoilingPt Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition Farnesyl pyrophosphate FPP , also known as farnesyl diphosphate FDP , is an intermediate in the HMG CoA reductase pathway used by organisms in the biosynthesis of terpene s, terpenoid s, and sterol s. It is the immediate precursor of squalene via the enzyme squalene synthase , dehydrodolichol diphosphate a precursor of dolichol , and geranylgeranyl pyrophosphate GGPP . Biosynthesis Farnesyl pyrophosphate synthase a prenyl transferase catalyzes sequential condensation reactions of dimethylallyl pyrophosphate with 2 units of 3 isopentenyl pyrophosphate to form farnesyl pyrophosphate, as is shown in the following two steps Dimethylallyl pyrophosphate reacts with 3 isopentenyl pyrophosphate to form geranyl pyrophosphate Image Cholesterol Synthesis Reaction8.png Geranyl pyrophosphate then reacts with another molecule of 3 isopentenyl pyrophosphate to form farnesyl pyrophosphate Image Cholesterol Synthesis Reaction9.png Regulation The above reactions are inhibited by bisphosphonate s used for osteoporosis . Related compounds Farnesene Farnesol Geranyl pyrophosphate Geranylgeranyl pyrophosphate Cholesterol metabolism intermediates DEFAULTSORT Farnesyl Pyrophosphate Category Organophosphates Category Sesquiterpenes Biochem stub fi Farnesyylipyrofosfaatti zh ... more details
Chembox Watchedfields changed verifiedrevid 443835762 ImageFile Geranylgeranyl pyrophosphate.png ImageSize IUPACName OtherNames Section1 Chembox Identifiers ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 394418 InChI 1 C20H36O7P2 c1 17 2 9 6 10 18 3 11 7 12 19 4 13 8 14 20 5 15 16 26 29 24,25 27 28 21,22 23 h9,11,13,15H,6 8,10,12,14,16H2,1 5H3, H,24,25 H2,21,22,23 b18 11 ,19 13 ,20 15 InChIKey OINNEUNVOZHBOX QIRCYJPOBR StdInChI Ref stdinchicite correct chemspider StdInChI 1S C20H36O7P2 c1 17 2 9 6 10 18 3 11 7 12 19 4 13 8 14 20 5 15 16 26 29 24,25 27 28 21,22 23 h9,11,13,15H,6 8,10,12,14,16H2,1 5H3, H,24,25 H2,21,22,23 b18 11 ,19 13 ,20 15 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey OINNEUNVOZHBOX QIRCYJPOSA N CASNo 6699 20 3 PubChem 447277 ChEBI Ref ebicite correct EBI ChEBI 48861 SMILES O P O O OP O O OC C C CC C C C CC C C C CC C C C C C MeSHName geranylgeranyl pyrophosphate Section2 Chembox Properties C 20 H 36 O 7 P 2 Appearance Density MeltingPt BoilingPt Section3 Chembox Hazards Solubility MainHazards FlashPt Autoignition Geranylgeranyl pyrophosphate is an intermediate in the HMG CoA reductase pathway used by organisms in the biosynthesis of terpene s and terpenoid s. ref http www.rpi.edu dept bcbp molbiochem MBWeb mb2 part1 cholesterol.htm Cholesterol Synthesis , Rensselaer Polytechnic Institute ref In plants it is also the precursor to carotenoid s, gibberellin s, tocopherol s, and chlorophyll s. It is also a precursor to geranylgeranylation geranylgeranylated proteins. Related compounds Geranylgeraniol Geranyl pyrophosphate Farnesyl pyrophosphate References reflist Cholesterol metabolism intermediates DEFAULTSORT Geranylgeranyl Pyrophosphate Category Organophosphates Category Diterpenes Biochem stub ja fi Geranyyligeranyylipyrofosfaatti ... more details
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