Cynarin

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of Clynarin
(1 R , 3 R , 4 S , 5 R ) - ( E , E ) -form (CAS number 212891-05-9)
General
Non-proprietary name Cynarin
other names
  • 1,3-Di- O -caffeoylquinic acid
  • 1,3-Di- O -caffeoylquinic acid
  • (1 R , 3 R , 4 S , 5 R ) -1,3-bis {[( E ) -3- (3,4-dihydroxyphenyl) prop-2-enoyl] oxy} -4,5-dihydroxycyclohexane-1 -carboxylic acid
Molecular formula C 25 H 24 O 12
Brief description

Powder with a slightly sweet taste

External identifiers / databases
CAS number
  • 212891-05-9 [(1 R , 3 R , 4 S , 5 R ) - ( E , E ) -form]
  • 1182-34-9 [ rel - (1α, 3 R , 4α, 5 R ) form with unknown C = C double bond isomerism ]
  • 19870-46-3 [(1 S , 3 R , 4 R , 5 R ) form with unknown C = C double bond isomerism]
  • 30964-13-7 [(1 R , 3 R , 4 S , 5 R ) form with unknown C = C double bond isomerism]
PubChem 5281769
ChemSpider 4445082
Wikidata Q1763092
properties
Molar mass 516.4 g mol −1
Physical state

firmly

density

1.6 g cm −3

solubility
  • partially soluble in water
  • dissolves well in alcohol and acetic acid
safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 280-302 + 352-305 + 351 + 338-312-337 + 313
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cynarin is a natural substance that is found in many plants . From a chemical point of view, it is a caffeoylic acid and an ester of quinic acid and two caffeic acid molecules .

Cynarin is a depsid and biologically active component of artichokes ( Cynara cardunculus ). Many health benefits of cynarin are described. Among other things, it acts as an antioxidant and is used in the treatment of digestive disorders. In addition, foods containing cynarin can make foods that are subsequently consumed taste sweeter . However, this perception has so far only been empirically confirmed for water .

Occurrence

Cynarin is mainly found in plants . The compound is particularly known as a constituent of the leaves and hearts of artichokes of the species Cynara cardunculus , although the concentration of cynarin therein is low. Other plants also contain cynarin, such as B. the thistle , the vinegar tree , the purple coneflower or the ragwort .

Plants containing cynarin (selection)

  • Artichoke ( Cynara cardunculus )

  • Grove ragwort ( Senecio nemorensis )

  • Field thistle ( Cirsium arvense )

  • Vinegar tree ( Rhus typhina )

  • Purple coneflower ( Echinacea purpurea )

properties

Chemical properties

Cynarin is soluble in water , but it dissolves better in alcoholic solutions and acetic acid . Crystalline cynarin can be obtained as a colorless solid in needle form. The compound is a weak acid and optically active {rotation value [α] D 25 = - 59 ° (c = 2; methanol )}. It can be easily oxidized to a yellow solid with barium hydroxide and lead acetate . Cynarin is a tri-depsid , so that the building blocks of the compound ( caffeic acid and quinic acid ) can be obtained by saponification with dilute sodium hydroxide solution .

Physiological properties

Nowadays, plants such as artichokes with a greatly increased content of active ingredients (e.g. cynarin) are specifically cultivated in order to use them for pharmaceutical purposes. In terms of the lipid-lowering effects of artichoke extracts, it has long been considered the main active ingredient. Today it is known that this property is primarily due to luteolin . Cynarin was also accepted as the main antioxidant in artichokes, which is now due to other phenolic ingredients ( flavonoids , hydroxycinnamic acid derivatives ). Nevertheless, together with other ingredients such as chlorogenic acids, it has a lipid-lowering and choleretic effect . In addition, it binds free radicals and has an antioxidant effect (although not as the main active ingredient). It also increases the secretion of bile , which is one of the main active principles in the treatment of digestive disorders . This has been confirmed by both pharmacological tests and clinical studies . Although cynarin is a bitter substance , it modifies the tongue so that food that is subsequently consumed can taste sweeter. The potassium salts of cynarin are responsible for this, although the underlying mechanism has not been researched. This phenomenon is known from other foods, but the duration of the effect is longer with Cynarin.

biosynthesis

The biosynthesis of cynarin can take place indirectly or directly. The indirect variants start from phenylalanine , which can be enzymatically synthesized to cynarin in different ways via different caffeoyl acids. Quinic acid is an intermediate product. However, this can also be acylated directly to chlorogenic acid with the coenzyme caffeoyl-CoA . A further acylation to 1,5- O -caffeoylquinic acid and subsequent transesterification produces cynarin:

Cynarin biosynthesis

use

Cynarin and other active ingredients from artichokes (e.g. chlorogenic acids ) are used as extracts in pharmacology because of their antioxidant , choleretic and lipid-lowering effects . Medicinal plants containing cynarin and medicinal plants with similar ingredients are used in the Japanese and Korean traditions to treat inflammation and allergic diseases.

Individual evidence

  1. ↑ a b c d e f Entry on Cynarin. In: Römpp Online . Georg Thieme Verlag, accessed on November 16, 2019.
  2. ↑ ChemSRC: cynarine .
  3. ↑ a b c Cynarin data sheet (PDF) from Carl Roth , accessed on November 16, 2019.
  4. ^ A b Luigi Panizzi, Maria Luisa Scarpati: Constitution of Cynarine, the Active Principle of the Artichoke . In: Nature . tape 174 , no. 4440 , 1954, pp. 1062 , doi : 10.1038 / 1741062a0 .
  5. ↑ a b c d e R. Hansel, O. Sticher (Ed.): Pharmakognosie - Phytopharmazie. 9th edition. Springer Medizin Verlag, Heidelberg 2010, ISBN 978-3-642-00962-4 , pp. 1065-1069.
  6. ↑ K. Hiller: Cynarea folium. In: M. Wichtl (ed.): Tea drugs and phytopharmaceuticals: A manual for practice on a scientific basis. 4th edition. Wissenschaftliche Verlagsgesellschaft, Stuttgart 2002, ISBN 3-8047-1854-X , pp. 173-175.
  7. ^ Ceren Gezer: Potential health effects of the popular compound of artichoke: Cynarin (CYN) . In: Progress in Nutrition . tape 19 , 1-S, 2017, ISSN  1129-8723 , p. 5-9 , doi : 10.23751 / pn.v19i1-p.4967 .
  8. ↑ a b Linda M. Bartoshuk, Chi-Hang Lee, Richard Scarpellino: Sweet Taste of Water Induced by Artichoke (Cynara scolymus) . In: Science . tape 178 , no. 4064 , 1972, pp. 988-990 , doi : 10.1126 / science.178.4064.988 , PMID 5084667 .
  9. ↑ Meryem Topal et al .: Antioxidant, antiradical, and anticholinergic properties of cynarin purified from the Illyrian thistle (Onopordum illyricum L.) . In: Journal of Enzyme Inhibition and Medicinal Chemistry . tape 31 , no. 2 , 2016, ISSN  1475-6366 , p. 266-275 , doi : 10.3109 / 14756366.2015.1018244 , PMID 25792498 .
  10. ↑ P. Matuschowski, A. Nahrstedt, H. Winterhoff: Pharmacological investigations of a fresh plant juice from Cynara scolymus for choleretic effects . In: Journal of Phytotherapy . tape 26 , no. 1 , 2005, ISSN  0722-348X , p. 14-19 , doi : 10.1055 / s-2005-865246 .
  11. ↑ Cinzia Comino et al .: Isolation and functional characterization of a cDNA coding a hydroxycinnamoyltransferase Involved in phenylpropanoid biosynthesis in Cynara cardunculus L . In: BMC Plant Biology . tape 7 , no. 1 , 2007, ISSN  1471-2229 , pp. 1-14 , doi : 10.1186 / 1471-2229-7-14 , PMID 17374149 .
  12. ↑ Hideko Morishita, Motoyo Ohnishi: Absorption, metabolism and biological activities of chlorogenic acids and related compounds . In: Studies in Natural Products Chemistry . tape 25 . Elsevier, 2001, p. 919-953 , doi : 10.1016 / s1572-5995 (01) 80024-7 .