OLEANOLIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H48O3
Molecular Weight	456.7014
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@]4([H])[C@@]5(C)CC[C@@]([H])(C(C)(C)[C@]5([H])CC[C@]43C)O)[C@]2([H])C1)C(=O)O

InChI

InChIKey=MIJYXULNPSFWEK-GTOFXWBISA-N

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

HIDE SMILES / InChI

Molecular Formula	C30H48O3
Molecular Weight	456.7014
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22377690http://korea.in-cosmetics.com/en/Exhibitors/2695677/GfN-GmbH-Selco-GmbH/Products/1138708/Ursolic-acid-Na-salt-natural | https://www.ulprospector.com/en/eu/PersonalCare/Detail/3345/93891/Ursolic-Acid-Sodium-Salt
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/16741586

Sodium Oleanolate is a natural active ingredient derived from many plants. This pentacyclic triterpenoid acid is manufactured by extraction of Salvia officinalis leaves, also known as common sage, Loquat leaves and Olea europea. It can be also found mainly in the balm of rosemary leaves. Ursolic acid and Oleanolic acid have an isomer structure and belong to one of the strongest triterpenoids, which is of most interest to use in Anti-Aging and Anti-Photo-Aging products.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Target ID: Elastase Sources: http://korea.in-cosmetics.com/en/Exhibitors/2695677/GfN-GmbH-Selco-GmbH/Products/1138708/Ursolic-acid-Na-salt-natural	Inhibitor 7728
Bile acid receptor FXR 29 Target ID: CHEMBL2047 Sources: http://www.ncbi.nlm.nih.gov/pubmed/19653193	Modulator 780
MAPK signaling pathway 26 Target ID: map04010 Sources: http://www.ncbi.nlm.nih.gov/pubmed/21328610	Activator 1343
PI3K-Akt signaling pathway 23 Target ID: map04151 Sources: http://www.ncbi.nlm.nih.gov/pubmed/21328610	Activator 1343

Conditions

Condition	Modality	Highest Phase	Product
Photoaging of skin 4 Sources: https://www.ulprospector.com/en/eu/PersonalCare/Detail/3345/93891/Ursolic-Acid-Sodium-Salt https://dailymed.nlm.nih.gov/dailymed/getFile.cfm?setid=27ced99b-59a5-473f-90c5-f72b7e48ebdc&type=pdf&name=27ced99b-59a5-473f-90c5-f72b7e48ebdc	Inactive ingredient	Not Provided 492	PREVENTAGE FIRMING DEFENSE NORMAL/OILY BROAD SPECTRUM SPF 15 MERLE NORMAN Approved Use Unknown
Acne 96 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=636ceab4-b6f2-4198-9574-94f123a5299b	Inactive ingredient	Approved 8043	24 HOUR PIMPLE PUNISHER Approved Use For treatment of Acne. Helps keep skin clear of new acne blemishes.
Renal fibrosis 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24393202	Preventing	Preclinical	Unknown Approved Use Unknown
Drug-induced liver injury 10 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17392098	Secondary	Preclinical	Unknown Approved Use Unknown
Tuberculosis 80 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27393091	Secondary	Preclinical	Unknown Approved Use Unknown
Cancer 569 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16741586	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Two new triterpenoid saponins from Aralia subcapitata.	2001	11858547
A new biologically active triterpenoid saponin from the leaves of Lepidagathis hyalina Nees.	2001	11841115
Saikosaponin v-1 from roots of Bupleurum chinense DC.	2001	11407813
Altered immunomodulating and toxicological properties of degraded Quillaja saponaria Molina saponins.	2001 Apr	11357894
Screening of triterpenoids isolated from Phyllanthus flexuosus for DNA topoisomerase inhibitory activity.	2001 Dec	11754608
Phytochemical and antimicrobial studies on Drynaria quercifolia.	2001 Dec	11731121
The first naturally occurring Tie2 kinase inhibitor.	2001 Dec 13	11735581
Synthesis and anti-HIV activity of oleanolic acid derivatives.	2001 Dec 17	11720855
Extraction, isolation and characterisation of antitumor principle, alpha-hederin, from the seeds of Nigella sativa.	2001 Feb	11270717
NMR and LC-MSn characterisation of two minor saponins from Ilex paraguariensis.	2001 Jan-Feb	11704961
Inhibitory role of GDP on saikosaponin (I) stimulated enzymes secretion and rising of [Ca2+]i in rat pancreatic acini.	2001 Jul	11749835
Purification of saponin compounds in Bupleurum falcatum by solvent partitioning and preparative LC.	2001 Jul	11515551
Effects of ginsenosides from Panax ginseng on cell-to-cell communication function mediated by gap junctions.	2001 Jul	11488454
Involvement of p-15(INK4b) and p-16(INK4a) gene expression in saikosaponin a and TPA-induced growth inhibition of HepG2 cells.	2001 Jul 13	11444823
Enantioselective synthesis and complement inhibitory assay of A/B-ring partial analogues of oleanolic acid.	2001 Jul 9	11425522
Effects of Quillaja saponins on growth, metabolism, egg production and muscle cholesterol in individually reared Nile tilapia (Oreochromis niloticus).	2001 Jun	11423383
In vitro antileishmanial activity of three saponins isolated from ivy, alpha-hederin, beta-hederin and hederacolchiside A(1), in association with pentamidine and amphotericin B.	2001 Jun	11406851
Pregnene derivatives from Solenostemma argel leaves.	2001 Jun	11394848
Kalopanaxsaponin A is a basic saponin structure for the anti-tumor activity of hederagenin monodesmosides.	2001 Mar	11301855
Inhibitory effects of triterpenoids and sterols on human immunodeficiency virus-1 reverse transcriptase.	2001 May	11432464
Ursene type nortriterpene from Debregeasia salicifolia.	2001 May	11395260
Studies on the constituents of Clematis species. VIII. Triterpenoid saponins from the aerial part of Clematis tibetana KUNTZ.	2001 May	11383622
Four new oleanane saponins from Anemone anhuiensis.	2001 May	11383621
D:A friedo-oleanane lactones from the stems of Mallotus repandus.	2001 May	11374945
Detoxification of lantana hepatotoxin, lantadene A, using Alcaligenes faecalis.	2001 May-Jun	11404834
[In vitro study of the antimutagenic activity of alphahederin].	2001 May-Jun	11397676
Efficient production of saikosaponins in Bupleurum falcatum root fragments combined with signal transducers.	2001 Nov	11762592
Antimycobacterial plant terpenoids.	2001 Nov	11731906
Two triterpene saponins from Achyranthes bidentata.	2001 Nov	11724247
Triterpenoids.	2001 Oct	11699886
Anti-AIDS agents. 48.(1) Anti-HIV activity of moronic acid derivatives and the new melliferone-related triterpenoid isolated from Brazilian propolis.	2001 Oct	11678650
Medicinal foodstuffs. XXVII. Saponin constituents of gotu kola (2): structures of new ursane- and oleanane-type triterpene oligoglycosides, centellasaponins B, C, and D, from Centella asiatica cultivated in Sri Lanka.	2001 Oct	11605675
Nitric oxide and tumor necrosis factor-alpha production by oleanolic acid via nuclear factor-kappaB activation in macrophages.	2001 Oct 19	11594750
Cancer chemopreventive agents, serratane-type triterpenoids from Picea jezoensis.	2001 Oct 30	11566485
Acetylated triterpene saponins from the Thai medicinal plant, Sapindus emarginatus.	2001 Sep	11558612
Protective effect of endothelin type A receptor antagonist on brain edema and injury after transient middle cerebral artery occlusion in rats.	2001 Sep	11546909
Gastroprotective activity of oleanolic acid derivatives on experimentally induced gastric lesions in rats and mice.	2002 Apr	11999138
In vitro antiinflammatory activity of kalopanaxsaponin A isolated from Kalopanax pictus in murine macrophage RAW 264.7 cells.	2002 Apr	11995927
A new naphthoquinone from Polygonum aviculare.	2002 Apr	11990427
HPLC analysis of plasma 9-methoxycanthin-6-one from Eurycoma longifolia and its application in a bioavailability/pharmacokinetic study.	2002 Apr	11988862
Three new triterpene saponins from two species of Carpolobia.	2002 Apr	11975499
Phytosterol content in American ginseng seed oil.	2002 Feb 13	11829639
Spasmolytic effects of baccharis conferta and some of its constituents.	2002 Jan	11829135
Kalopanaxsaponin A from Kalopanax pictus, a potent antioxidant in the rheumatoidal rat treated with Freund's complete adjuvant reagent.	2002 Jan	11744304
Selective cytotoxicity of betulinic acid on tumor cell lines, but not on normal cells.	2002 Jan 10	11734332
Inhibition of alpha-glucosidase by oleanolic acid and its synthetic derivatives.	2002 Jun	12031449
The anti-inflammatory triterpenoid methyl 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate methanol solvate hydrate.	2002 Mar	11870328
Quantitative determination for cytotoxic Friedo-nor-oleanane derivatives from five morphological types of Maytenus ilicifolia (Celastraceae) by reverse-phase high-performance liquid chromatography.	2002 Mar-Apr	12018026
[Comparative study of cytotoxic and hemolytic effects of triterpenoids isolated from Ginseng and Sea cucumber].	2002 Mar-Apr	11963541
RP-LC determination of oleane derivatives in Terminalia arjuna.	2002 May 15	12008123

Patents

Sample Use Guides

In Vivo Use Guide

In model of kidney disease, oleanolic acid was dissolved in 2% w/v dimethyl sulfoxide (DMSO) and then diluted with distilled water for each injection to a final DMSO concentration of 0.2% w/v. Oleanolic acid or vehicle was administered intraperitoneally (60 mg/kg i.p). one day before UUO, and was continued for 3 or 7 days after surgery.

Route of Administration: Other

In Vitro Use Guide

For cell viability assay, HepG2 cells were plated at a density of 5000 per well in a 96-well plate. After culturing overnight, the cells were exposed to fresh medium containing different concentrations of OA. 24 hours later, the cell viability was determined by CellTiter-Glo Luminescence Cell Viability Assay (Promega) according to the manufacturer’s instructions. In order to determine whether OA would affect the activity of FXR-LBD, HepG2 cells were transfected with an expression vector for Gal4-DBD-FXR-LBD, a reporter plasmid pFR-Luc, an internal control Renilla luciferase vector and then treated with FXR agonist CDCA in the presence of increasing amounts of OA.

Substance Class	Chemical Created by `admin` on `Sat Jun 26 08:12:12 UTC 2021` Edited by `admin` on `Sat Jun 26 08:12:12 UTC 2021`
Record UNII	6SMK8R7TGJ
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

OLEANOLIC ACID

Official Name

English

OLEANIC ACID

Common Name

English

OLEANOLIC ACID [WHO-DD]

Common Name

English

(3.BETA.)-3-HYDROXYOLEAN-12-EN-28-OIC ACID

Common Name

English

OLEANOLIC ACID (CONSTITUENT OF HOLY BASIL LEAF) [DSC]

Common Name

English

OLEANOLIC ACID (CONSTITUENT OF BANABA LEAF) [DSC]

Common Name

English

ASTRANTIAGENIN C

Common Name

English

GIGANTEUMGENIN C

Common Name

English

VIRGAUREAGENIN B

Common Name

English

OLEANOLIC ACID [INCI]

Common Name

English

OLEANOLIC ACID [MI]

Common Name

English

OLEANOLIC ACID [USP-RS]

Common Name

English

OLEONOLIC ACID

Common Name

English

3.BETA.-HYDROXYOLEAN-12-EN-28-OIC ACID

Common Name

English

NSC-114945

Code

English

OLEANOL

Common Name

English

GLEDIGENIN 1

Common Name

English

CARYOPHYLLIN

Common Name

English

Classification Tree Code System Code

DSLD

1800 (Number of products:12)