Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C25H24O12 |
Molecular Weight | 516.4509 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 2 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@@H]1C[C@](C[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@H]1O)(OC(=O)\C=C\C3=CC(O)=C(O)C=C3)C(O)=O
InChI
InChIKey=YDDUMTOHNYZQPO-RVXRWRFUSA-N
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1
Cynarine (Cynarin) is the most noteworthy active ingredient of the artichoke, and is considered a medicinal foodstuff due to its beneficial effect on the organism, derived from its condition as a stimulant of bile secretion (choleretic effect). Cynarine is present in artichoke leaves and has a beneficial effect on the control of gallstones, helps control cholesterol levels and improves gallbladder function. Chlorogenic acid and cynarin have been shown to have
activity against oxidative stress in human leukocytes,
whereas cynarin has also been shown to have hypocholesterolemic, hepatoprotective, and, more recently, antihuman immunodeficiency virus-1 (anti-HIV-1; 44) activities. Cynarin had marked antioxidant, anticholinergic, reducing ability, radical-scavenging, and metal-binding activities.
Originator
Sources: http://www.organic-herb.com/Product/552.html
Curator's Comment: Cynarin, isolated from artichoke, was characterized for the first time by Panizzi and Scarpati.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: WP2708 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8824943 |
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Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25792498 |
243.67 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Palliative | Cynara scolymus Approved UseDigestive complaints, Dyspepsia |
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Palliative | Cynara scolymus Approved UseHyperlipidemia |
Sample Use Guides
In Vivo Use Guide
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Herbal_-_HMPC_assessment_report/2011/12/WC500119940.pdf
Curator's Comment: Humans, oral: Many artichoke supplements recommend a dosage of around 1500 mg to 2000 mg. http://www.nutragreenbio.com/product/artichoke-extract
Cynarin (100 and 200 mg/kg body weight) administered intravenously to rabbits, lowered serum cholesterol by about 20% Triton WR 1339-induced hypercholesterolaemia. In rats it was significantly lowered (p=0.05-0.02) by cynarin after intraperitoneal administration (2*200 mg/kg body weight).
Route of Administration:
Other
In Vitro Use Guide
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Herbal_-_HMPC_assessment_report/2011/12/WC500119940.pdf
Curator's Comment: Cynarin demonstrated 87.72% inhibition of linoleic acid lipid peroxidation at 30 ug/mL concentration. https://www.ncbi.nlm.nih.gov/pubmed/25792498
Cynarin and caffeic acid showed significant cytoprotective activity (p<0.01 at 1 mg/ml) against carbon tetrachloride in isolated rat hepatocytes, reducing leakage of the liver enzymes glutamine oxaloacetic transaminase and glutamic pyrovic transaminase.
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NCI_THESAURUS |
C66913
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100000083760
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3124
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SUB06870MIG
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CHEMBL2105478
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CYNARINE
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5281769
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C100257
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m4033
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30964-13-7
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C81041
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212891-05-9
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ACTIVE MOIETY