Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C36H56O9 |
Molecular Weight | 632.8244 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 13 / 13 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]6(O[C@H]1CC[C@@]2(C)[C@@]([H])(CC[C@]3(C)[C@]2([H])CC=C4[C@]5([H])CC(C)(C)CC[C@@]5(CC[C@@]34C)C(O)=O)C1(C)C)O[C@@H]([C@@H](O)[C@H](O)[C@H]6O)C(O)=O
InChI
InChIKey=IUCHKMAZAWJNBJ-RCYXVVTDSA-N
InChI=1S/C36H56O9/c1-31(2)14-16-36(30(42)43)17-15-34(6)19(20(36)18-31)8-9-22-33(5)12-11-23(32(3,4)21(33)10-13-35(22,34)7)44-29-26(39)24(37)25(38)27(45-29)28(40)41/h8,20-27,29,37-39H,9-18H2,1-7H3,(H,40,41)(H,42,43)/t20-,21-,22+,23-,24-,25-,26+,27-,29+,33-,34+,35+,36-/m0/s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/24556278Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22807953 |
http://www.hmdb.ca/metabolites/HMDB40851
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24556278
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22807953 |
http://www.hmdb.ca/metabolites/HMDB40851
Calenduloside E (3-O-[beta-d-glucuronopyranosyl]oleanolic acid), the glucuronic acid conjugate of oleanolic acid, is a triterpenoid saponin present in a wide variety of Aralia plants, in which the content of calenduloside E is about 0.02%. A number of studies of the biological activity of calenduloside E has been reported since its first isolation by Kasprzyk and Wojciechowski. These studies indicate that calenduloside E has hypoglycemic activity and is potentially useful in the treatment of diabetes and morbid obesity. It may also be useful as a spermicidal contraceptive and as an antiarrhythmic agent. Because of its wide-ranging biological activity and low toxicity, the potential clinical use of calenduloside E has attracted much attention in recent years. Furthermore, its active metabolite, oleanolic acid, has been shown to possess analgesic, antiinflammatory, hepatoprotective, antitumor and hypolipidemic effects as well as having hypoglycemic activity.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:1901317 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21237343 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
---|---|---|
Calenduloside E 6'-methyl ester induces apoptosis in CT-26 mouse colon carcinoma cells and inhibits tumor growth in a CT-26 xenograft animal model. | 2012 Jul |
|
Pharmacokinetic study of calenduloside E and its active metabolite oleanolic acid in beagle dog using liquid chromatography-tandem mass spectrometry. | 2014 Mar 1 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24556278
In pharmacokinetic study Calenduloside E was administered as single oral and intravenous doses to dogs. The oral dose was formulated in a capsule with -cyclodextrin as excipient and administered at doses of 1.05, 2.10 and 4.20 mg/kg. The intravenous dose was formulated at a concentration of 5 mg/mL in a vehicle of polyethylene glycol 400:saline (2:1, v/v) and administered at a dose of 2.10 mg/kg.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21237343
The spermicidal activity of OAG was assayed according to the Sander–Cramer method. Varying concentrations of OAG solution were prepared in physiological saline (0, 10, 30, 40, 50, 60 mkg/mL) and 100 mkL of each was mixed with an aliquot of 20 mkL of sperm suspension. The specimens were examined under a phase contrast microscope (×100) after 20 s of treatment and counted for motile sperm.
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SUBSTANCE RECORD