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Calenduloside E

CAT: 0804-HY-N6850-02Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N6850-02Size:10 mg
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Description
Calenduloside E is a pentacyclic triterpenoid saponin that can be extracted from the bark and roots of Aralia ovata, and has anti-inflammatory and anti-apoptotic activities. Calenduloside E alleviates atherosclerosis by regulating macrophage polarization, improves mitochondrial function by regulating the AMPK-SIRT3 pathway, and alleviates acute liver injury. In addition, Calenduloside E promotes the interaction between L-type calcium channels and Bcl-2 related apoptosis genes, inhibits calcium overload, and alleviates myocardial ischemia/reperfusion injury. Calenduloside E also improves non-alcoholic fatty liver disease by regulating heat shock-dependent pathways, and inhibits ROS mediated JAK1-STAT3 pathways to reduce cellular inflammatory responses[1][2][3][4][5][6].
CAS Number
26020-14-4
UNSPSC
12352005
Target
AMPK; Apoptosis; Bcl-2 Family; Calcium Channel; Interleukin Related; JAK; PPAR; Pyroptosis; Reactive Oxygen Species (ROS) ; SOD; STAT; TNF Receptor
Type
Natural Products
Related Pathways
Apoptosis; Cell Cycle/DNA Damage; Epigenetics; Immunology/Inflammation; JAK/STAT Signaling; Membrane Transporter/Ion Channel; Metabolic Enzyme/Protease; Neuronal Signaling; NF-κB; PI3K/Akt/mTOR; Protein Tyrosine Kinase/RTK; Stem Cell/Wnt; Vitamin D Related/Nuclear Receptor
Field of Research
Inflammation/Immunology; Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/calenduloside-e.html
Purity
99.07
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
C[C@]12[C@]3(C([C@@]4([H])[C@](C(O)=O)(CCC(C)(C)C4)CC3)=CC[C@]1([H])[C@@]5([C@@](C(C)([C@@H](O[C@]6([H])O[C@@H]([C@@H](O)[C@H](O)[C@H]6O)C(O)=O)CC5)C)([H])CC2)C)C
Molecular Formula
C36H56O9
Molecular Weight
632.82
References & Citations
[1]Tian Y, et al. The clickable activity-based probe of anti-apoptotic calenduloside E. Pharm Biol. 2019 Dec;57 (1) :133-139.|[2]Lanfang Li, et al. "Calenduloside e modulates macrophage polarization via KLF2-regulated glycolysis, contributing to attenuates atherosclerosis." International Immunopharmacology 117 (2023) : 109730.|[3]Pengli Guo, et al. "Isolation of Calenduloside E from achyranthes bidentata blume and its effects on LPS/D-GalN-induced acute liver injury in mice by regulating the AMPK-SIRT3 signaling pathway." Phytomedicine 125 (2024) : 155353.|[4]Ruiying Wang, et al. "Calenduloside E suppresses calcium overload by promoting the interaction between L-type calcium channels and Bcl2-associated athanogene 3 to alleviate myocardial ischemia/reperfusion injury." Journal of Advanced Research 34 (2021) : 173-186.|[5]Yifei Le, et al. "Calenduloside E ameliorates non-alcoholic fatty liver disease via modulating a pyroptosis-dependent pathway." Journal of Ethnopharmacology 319 (2024) : 117239.|[6]Min Wang, et al. "Calenduloside E ameliorates myocardial ischemia‐reperfusion injury through regulation of AMPK and mitochondrial OPA1." Oxidative Medicine and Cellular Longevity 2020.1 (2020) : 2415269.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Calenduloside E

Oleanolic acid 3-O-beta-D-glucosiduronic acid is a beta-D-glucosiduronic acid. It is functionally related to an oleanolic acid.

CAS Number26020-14-4
PubChem CID176079
IUPAC Name(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Molecular FormulaC36H56O9
Molecular Weight632.8
XLogP6.1
Topological Polar Surface Area154
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count9
Rotatable Bond Count4
Heavy Atom Count45
Formal Charge0
Complexity1260
SMILES
C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)C)C)(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O)O
InChI
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
InChIKey
IUCHKMAZAWJNBJ-RCYXVVTDSA-N
Chemical Structure
2D Structure
2D structure of Calenduloside E
CAS: 26020-14-4
CID: 176079
Formula: C36H56O9
MW: 632.8
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight632.8
XLogP36.1
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count9
Rotatable Bond Count4
Exact Mass632.39243336
Monoisotopic Mass632.39243336
Topological Polar Surface Area154 Ų
Heavy Atom Count45
Formal Charge0
Complexity1260
Isotope Atom Count0
Defined Atom Stereocenter Count13
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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