Kyselina arachidonová

Kyselina arachidonová
Obecné
Systematický názevall-cis-ikosa-5,8,11,14-tetraenová kyselina
Ostatní názvyall-cis-eikosa-5,8,11,14-tetraenová kyselina
Sumární vzorecC20H32O2
Identifikace
Registrační číslo CAS506-32-1
Vlastnosti
Molární hmotnost304,47 g/mol
Hustota0,922 g/cm3
Disociační konstanta pKa4,752
Bezpečnost
GHS07 – dráždivé látky
GHS07
[1]
Varování[1]
Není-li uvedeno jinak, jsou použity
jednotky SI a STP (25 °C, 100 kPa).
Některá data mohou pocházet z datové položky.

Kyselina arachidonová (resp. konjugovaná báze arachidonát) je dvacetiuhlíkatá polynenasycená omega-6 mastná kyselina se čtyřmi dvojnými vazbami, důležitá v metabolismu celé řady rostlin i živočichů včetně člověka. Z kyseliny arachidonové jsou chemicky odvozeny eikosanoidy[2] – tedy zejména různé leukotrieny, prostaglandiny, prostacykliny a tromboxany, důležité signální látky či hormony.

Arachidonová kyselina je důležitou složkou buněčných membrán živočichů, ale ve velkém se vyskytuje i v živočišné tukové tkáni.[3]

Metabolismus

Kyselina arachidonová není považována za esenciální mastnou kyselinu, protože většina živočichů včetně člověka je schopna ji vyrábět.[4] V posledních letech se však ukazuje, že přítomnost arachidonové kyseliny v potravě má pozitivní vliv na zdraví dětí[5] a situace je sporná.

Syntéza arachidonové kyseliny probíhá z kyseliny linolové, což však již je esenciální mastná kyselina, neboť živočichové neumí zavádět dvojné vazby dále než na devátém uhlíku. Linolová (omega-6) kyselina je nejprve za pomoci NADH oxidována mezi šestým a sedmým uhlíkem, čímž vzniká gama-linolenová kyselina, načež elongázovým systémem dochází k přidání dvou uhlíků. V posledním kroku vzniká za spotřeby NADH nenasycená vazba mezi 5. a 6. uhlíkem.[4]

Kyselina arachidonová je hlavní výchozí látkou pro tvorbu různých eikosanoidů. Nejčastěji se pro tyto potřeby arachidonová kyselina uvolňuje z druhé uhlíkové pozice glycerolového skeletu fosfolipidů, tuto hydrolýzu katalyzuje fosfolipáza A2. Následně může být arachidonát použit v různých metabolických drahách. Cyklooxygenázovou cestou dochází k syntéze prostanoidů, lipoxygenázovou cestou vznikají leukotrieny a lipoxiny.[4]

Reference

  1. ↑ a b Arachidonic acid. pubchem.ncbi.nlm.nih.gov [online]. PubChem [cit. 2021-05-23]. Dostupné online. (anglicky) 
  2. ↑ LEHNINGER, Albert L., David L. Nelson, Michael M. Cox. Lehninger principles of biochemistry. 3rd. vyd. New York: Worth Publishers, 2000. Dostupné online. ISBN 1-57259-931-6. 
  3. ↑ Robert K. Murray; Daryl K. Granner; Joe C. Davis; Peter A. Mayes; Victor W. Rodwell. Harper’s Illustrated Biochemistry; 29th edition. [s.l.]: [s.n.] 
  4. ↑ a b c Robert K. Murray; Daryl K. Granner; Joe C. Davis; Peter A. Mayes; Victor W. Rodwell. Harper’s Illustrated Biochemistry; twenty-sixth edition. [s.l.]: [s.n.], 2003. ISBN 0-07-138901-6. 
  5. ↑ ROSS, Don. Food and Nutrition. Jaipur, Indie: Oxford Book Company, 2010. ISBN 978-93-80179-13-1. 

Externí odkazy

Monokarboxylové kyseliny
monokarboxylové nasycené kyseliny
kyselina mravenčí (HCOOH) • kyselina octová (CH3COOH) • kyselina propionová (C2H5COOH) • kyselina máselná (C3H7COOH) • kyselina valerová (C4H9COOH) • kyselina 3-methylbutanová (isovalerová) (CH3CH(CH3)CH2COOH) • kyselina kapronová (C5H11COOH) • kyselina enanthová (C6H13COOH) • kyselina kaprylová (C7H15COOH) • kyselina pelargonová (C8H17COOH) • kyselina kaprinová (C9H19COOH) • kyselina undecylová (C10H21COOH) • kyselina laurová (C11H23COOH) • kyselina tridecylová (C12H25COOH) • kyselina myristová (C13H27COOH) • kyselina pentadecylová (C14H29COOH) • kyselina palmitová (C15H31COOH) • kyselina heptadekanová (C16H33COOH) • kyselina stearová (C17H35COOH) • kyselina nonadecylová (C18H37COOH) • kyselina arachidová (C19H39COOH) • kyselina behenová (C21H43COOH) • kyselina lignocerová (C23H47COOH)
mononenasycené monokarboxylové kyseliny
polynenasycené monokarboxylové kyseliny
kyselina linolová (C17H31COOH) • kyselina linolenová (C17H29COOH) • kyselina alfa-eleostearová (C17H29COOH) • kyselina arachidonová (C19H31COOH) • kyselina eikosapentaenová (C19H29COOH) • kyselina klupadonová (dokosapentaenová) (C21H33COOH) • kyselina dokosahexaenová (C21H31COOH)
aromatické monokarboxylové kyseliny
kyselina acetyloctová (CH3COCH2COOH)
dikarboxylové kyseliny • hydroxykyseliny

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