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Oleanolic-acid

Oleanolic acid is a natural pentacyclic triterpene found in Panax ginseng, Rhabdodendron amazonicum, and in many plants as the free acid or the aglycone for many saponins.It can rearrange to the isomer, ursolic acid

General

Type : Not A\/B H target, Natural, Terpenoid

Chemical_Nomenclature : (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Canonical SMILES : CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1)C)C(=O)O)C

InChI : InChI=1S\/C30H48O3\/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7\/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)\/t20-,21-,22+,23-,27-,28+,29+,30-\/m0\/s1

InChIKey : MIJYXULNPSFWEK-GTOFXWBISA-N

Other name(s) : Oleanolic acid, Oleanic acid, Caryophyllin, Astrantiagenin C

MW : 456.7

Formula : C30H48O3

CAS_number : 508-02-1

PubChem : 10494

UniChem : MIJYXULNPSFWEK-GTOFXWBISA-N

Target

Families : Oleanolic-acid ligand of proteins in family
ACHE

Protein :
human-PNLIP

References (13)

Title : Discovery of triterpenoids as potent dual inhibitors of pancreatic lipase and human carboxylesterase 1 - Zhang_2022_J.Enzyme.Inhib.Med.Chem_37_629
Author(s) : Zhang J , Pan QS , Qian XK , Zhou XL , Wang YJ , He RJ , Wang LT , Li YR , Huo H , Sun CG , Sun L , Zou LW , Yang L
Ref : J Enzyme Inhib Med Chem , 37 :629 , 2022
PubMedID: 35100926

Title : Ursolic acid and its isomer oleanolic acid are responsible for the anti-dementia effects of Ocimum sanctum in olfactory bulbectomized mice - Nguyen_2022_J.Nat.Med__
Author(s) : Nguyen HT , Le XT , Van Nguyen T , Phung HN , Pham HTN , Nguyen KM , Matsumoto K
Ref : J Nat Med , : , 2022
PubMedID: 35218459

Title : Phytochemical Analysis and Evaluation of Biological Activity of Lawsonia inermis Seeds Related to Alzheimer's Disease - Balaei-Kahnamoei_2021_Evid.Based.Complement.Alternat.Med_2021_5965061
Author(s) : Balaei-Kahnamoei M , Saeedi M , Rastegari A , Shams Ardekani MR , Akbarzadeh T , Khanavi M
Ref : Evid Based Complement Alternat Med , 2021 :5965061 , 2021
PubMedID: 34335830

Title : Terpenes and Phenylpropanoids as Acetyl- and Butyrylcholinesterase Inhibitors: A Comparative Study - Szwajgier_2019_Curr.Alzheimer.Res_16_963
Author(s) : Szwajgier D , Baranowska-Wojcik E
Ref : Curr Alzheimer Res , 16 :963 , 2019
PubMedID: 31660828

Title : Ursolic and oleanolic acid derivatives with cholinesterase inhibiting potential - Loesche_2018_Bioorg.Chem_85_23
Author(s) : Loesche A , Kowitsch A , Lucas SD , Al-Halabi Z , Sippl W , Al-Harrasi A , Csuk R
Ref : Bioorg Chem , 85 :23 , 2018
PubMedID: 30599410

Title : Oleanolic acid ameliorates cognitive dysfunction caused by cholinergic blockade via TrkB-dependent BDNF signaling - Jeon_2017_Neuropharmacol_113_100
Author(s) : Jeon SJ , Lee HJ , Lee HE , Park SJ , Gwon Y , Kim H , Zhang J , Shin CY , Kim DH , Ryu JH
Ref : Neuropharmacology , 113 :100 , 2017
PubMedID: 27470063

Title : Neurologically Potent Molecules from Crataegus oxyacantha\; Isolation, Anticholinesterase Inhibition, and Molecular Docking - Ali_2017_Front.Pharmacol_8_327
Author(s) : Ali M , Muhammad S , Shah MR , Khan A , Rashid U , Farooq U , Ullah F , Sadiq A , Ayaz M , Ahmad M , Latif A
Ref : Front Pharmacol , 8 :327 , 2017
PubMedID: 28638340

Title : Bioactive constituents of Salvia chrysophylla Stapf - Culhaoglu_2013_Nat.Prod.Res_27_438
Author(s) : Culhaoglu B , Yapar G , Dirmenci T , Topcu G
Ref : Nat Prod Res , 27 :438 , 2013
PubMedID: 23126495

Title : Facile synthesis of three bidesmosidic oleanolic acid saponins with strong inhibitory activity on pancreatic lipase - Guo_2009_Carbohydr.Res_344_1167
Author(s) : Guo T , Liu Q , Wang P , Zhang L , Zhang W , Li Y
Ref : Carbohydr Res , 344 :1167 , 2009
PubMedID: 19463989

Title : Oleanolic acid and related derivatives as medicinally important compounds - Sultana_2008_J.Enzyme.Inhib.Med.Chem_23_739
Author(s) : Sultana N , Ata A
Ref : J Enzyme Inhib Med Chem , 23 :739 , 2008
PubMedID: 18618318

Title : Release of acetylcholine to raise insulin secretion in Wistar rats by oleanolic acid, one of the active principles contained in Cornus officinalis - Hsu_2006_Neurosci.Lett_404_112
Author(s) : Hsu JH , Wu YC , Liu IM , Cheng JT
Ref : Neuroscience Letters , 404 :112 , 2006
PubMedID: 16759806

Title : Three new cholinesterase-inhibiting cis-clerodane diterpenoids from Otostegia limbata - Ahmad_2005_Chem.Pharm.Bull.(Tokyo)_53_378
Author(s) : Ahmad VU , Khan A , Farooq U , Kousar F , Khan SS , Nawaz SA , Abbasi MA , Choudhary MI
Ref : Chem Pharm Bull (Tokyo) , 53 :378 , 2005
PubMedID: 15802835

Title : Inhibition of alpha-glucosidase by oleanolic acid and its synthetic derivatives - Ali_2002_Phytochemistry_60_295
Author(s) : Ali MS , Jahangir M , Hussan SS , Choudhary MI
Ref : Phytochemistry , 60 :295 , 2002
PubMedID: 12031449