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14216-03-6 , Hederacoside C , Akebiasaponin PK; Tauroside H2; Hederoside H; Astrantiasaponin H

14216-03-6 , Hederacoside C ,
Akebiasaponin PK;
Tauroside H2;
Hederoside H;
Astrantiasaponin H
Cas:14216-03-6
C59H96O26 / 1221.38
MFCD00198062

Hederacoside C, Akebiasaponin PK; 

Tauroside H2; Hederoside H; Astrantiasaponin H

Hederacoside C is a saponin that has been found in K. pictus and has anti-inflammatory activity. It is an inhibitor of acetylcholinesterase (AChE; IC50 = 31.3 μM). Hederacoside C (0.5-5 μg) inhibits mutagenicity induced by aflatoxin B1 in S. typhimurium agar cultures from 21 to 67%.3 It reduces TNF-α, IL-1β, IL-6, COX-2, and nitric oxide synthase (NOS) levels in a concentration-dependent manner and IL-1 receptor-associated kinase-1 (IRAK1) activity in isolated mouse peritoneal macrophages stimulated by LPS when used at concentrations ranging from 5 to 10 μM. Hederacoside C (0.02 mg/kg) reduces carrageenan-induced hind paw edema by 37% compared to vehicle control in a rat model of acute inflammation. It reduces scopolamine-induced memory impairment and increases latency in a passive avoidance test and spontaneous alteration in a Y-maze in mice by 100 and 59%, respectively, when administered at a dose of 40 mg/kg. Hederacoside C (5 mg/kg, i.p.) reduces serum levels of TNF-α and IL-1β in LPS-challenged mice by 60 and 65%, respectively.

Hederacoside C analytical standard provided with w/w absolute assay, to be used for quantitative titration.

Hederacoside C is a triterpene saponin and an active ingredient and a marker of ivy leaf extract. It exhibits biological properties such as expectorant and bronchospasmolytic effects and hence finds therapeutic applications in the treatment of chronic inflammatory bronchial conditions and productive coughs.

Hederacoside C is a major bioactive constituent isolated from Hedera helix L. It exhibits pharmacological properties such as antibacterial, expectorant, bronchodilator and bronchospasmolytic effects. It is widely used in the treatment of respiratory disorders involving acute respiratory infections, chronic inflammatory bronchitis and productive coughs.

Kalopanaxsaponin B is a triterpenoid saponin with hederagenin as the aglycone part. It has been isolated from the stem bark of Kalopanax pictus. It has a role as an anti-inflammatory agent and a plant metabolite. It is a pentacyclic triterpenoid, a triterpenoid saponin and a carboxylic ester. It derives from a hederagenin.

Hederacoside C is a natural compound that is extracted from the acetate extract of the leaves of Hedera helix. It has been shown to have inhibitory effects on inflammatory bowel disease and bowel disease. Hederacoside C has been found to have antimicrobial activity against both Gram-positive and Gram-negative bacteria, including methicillin-resistant Staphylococcus aureus, Salmonella typhimurium, Pseudomonas aeruginosa, Klebsiella pneumoniae, Escherichia coli, and Enterobacter cloacae. The antibacterial effect of hederacoside C is due to its structural similarity to ampicillin. Hederacoside C also has anti-inflammatory properties which are related to its inhibition of prostaglandin synthesis.

CAS Number

14216-03-6

Product Name

Hederacoside C

IUPAC Name

[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate

Molecular Formula

C59H96O26

Molecular Weight

1221.38 g/mol

InChI

InChI=1S/C59H96O26/c1-24-34(63)38(67)42(71)49(78-24)83-46-29(20-60)80-48(45(74)41(46)70)77-22-30-37(66)40(69)44(73)51(81-30)85-53(75)59-17-15-54(3,4)19-27(59)26-9-10-32-55(5)13-12-33(56(6,23-61)31(55)11-14-58(32,8)57(26,7)16-18-59)82-52-47(36(65)28(62)21-76-52)84-50-43(72)39(68)35(64)25(2)79-50/h9,24-25,27-52,60-74H,10-23H2,1-8H3/t24-,25-,27-,28-,29+,30+,31+,32+,33-,34-,35-,36-,37+,38+,39+,40-,41+,42+,43+,44+,45+,46+,47+,48+,49-,50-,51-,52-,55-,56-,57+,58+,59-/m0/s1

InChI Key

RYHDIBJJJRNDSX-MCGLQMIESA-N

SMILES

C[C@@H]1O[C@H]([C@@H]([C@@H]([C@H]1O)O)O)O[C@H]2[C@@H]([C@H]([C@@H](O[C@@H]2CO)OC[C@H]3O[C@H]([C@@H]([C@H]([C@@H]3O)O)O)OC([C@]45CCC(C)(C[C@H]4C6=CC[C@@H]7[C@]8(CC[C@@H]([C@@](CO)([C@@H]8CC[C@]7([C@@]6(CC5)C)C)C)O[C@@H]9OC[C@@H]([C@@H]([C@H]9O[C@@H]%10O[C@H]([C@@H]([C@H]([C@H]%10O)O)O)C)O)O)C)C)=O)O)O

Solubility

Soluble in DMSO

Synonyms

kalopanax saponin B, kalopanaxsaponin B, kizuta saponin K(12), kizuta saponin K12

Canonical SMILES

CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OCC3C(C(C(C(O3)OC(=O)C45CCC(CC4C6=CCC7C8(CCC(C(C8CCC7(C6(CC5)C)C)(C)CO)OC9C(C(C(CO9)O)O)OC1C(C(C(C(O1)C)O)O)O)C)(C)C)O)O)O)CO)O)O)O

Isomeric SMILES

C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)O)OC[C@@H]3[C@H]([C@@H]([C@H]([C@@H](O3)OC(=O)[C@@]45CC[C@@]6(C(=CC[C@H]7[C@]6(CC[C@@H]8[C@@]7(CC[C@@H]([C@@]8(C)CO)O[C@H]9[C@@H]([C@H]([C@H](CO9)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)C)O)O)O)C)C)[C@@H]4CC(CC5)(C)C)C)O)O)O)CO)O)O)O


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