Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C30H48O4 |
Molecular Weight | 472.6997 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC(C)(C)CC[C@@]1(CC[C@]3(C)C2=CC[C@]4([H])[C@@]5(C)C[C@@H](O)[C@H](O)C(C)(C)[C@]5([H])CC[C@@]34C)C(O)=O
InChI
InChIKey=MDZKJHQSJHYOHJ-LLICELPBSA-N
InChI=1S/C30H48O4/c1-25(2)12-14-30(24(33)34)15-13-28(6)18(19(30)16-25)8-9-22-27(5)17-20(31)23(32)26(3,4)21(27)10-11-29(22,28)7/h8,19-23,31-32H,9-17H2,1-7H3,(H,33,34)/t19-,20+,21-,22+,23-,27-,28+,29+,30-/m0/s1
Molecular Formula | C30H48O4 |
Molecular Weight | 472.6997 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/25093990Curator's Comment: Description was created using several sources including: http://www.olikem.com/products/4/Maslinic-Acid.htm|
https://www.ncbi.nlm.nih.gov/pubmed/21524306|https://www.ncbi.nlm.nih.gov/pubmed/21970807|https://www.ncbi.nlm.nih.gov/pubmed/20814972|https://www.ncbi.nlm.nih.gov/pubmed/24863350|https://www.ncbi.nlm.nih.gov/pubmed/27931683|https://www.ncbi.nlm.nih.gov/pubmed/27976034|https://www.ncbi.nlm.nih.gov/pubmed/27770787|http://www.sciencedirect.com/science/article/pii/S1875536409600054|https://www.ncbi.nlm.nih.gov/pubmed/21800347
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25093990
Curator's Comment: Description was created using several sources including: http://www.olikem.com/products/4/Maslinic-Acid.htm|
https://www.ncbi.nlm.nih.gov/pubmed/21524306|https://www.ncbi.nlm.nih.gov/pubmed/21970807|https://www.ncbi.nlm.nih.gov/pubmed/20814972|https://www.ncbi.nlm.nih.gov/pubmed/24863350|https://www.ncbi.nlm.nih.gov/pubmed/27931683|https://www.ncbi.nlm.nih.gov/pubmed/27976034|https://www.ncbi.nlm.nih.gov/pubmed/27770787|http://www.sciencedirect.com/science/article/pii/S1875536409600054|https://www.ncbi.nlm.nih.gov/pubmed/21800347
Maslinic acid is a pentacyclic triterpene occur naturally in many herbs and plant foods. It is found in the protective wax-like coating of the leaves and fruit of Olea europaea and is one of the ingredients in olive oil. Benefits of the olive oil triterpenes (oleanolic and maslinic acid) on the primary prevention of cardiovascular disease in addition to their bioavailability and disposition have been investigated in Phase 3 clinical trial in healthy participants. Maslinic acid is used in skin care products and dietary supplements. Maslinic acid exerts a wide range of biological activities including antitumor, antidiabetic, anti-obesity, antioxidant, anti-inflammatory, cardioprotective, neuroprotective and antimicrobial. In vitro anti-diabetic effects of maslinic acid are exhibited by increasing glycogen content and inhibiting glycogen phosphorylase activity in HepG2 cells. It was shown to induce the phosphorylation level of IRβ-subunit, Akt, and GSK3β with specific activation of Akt. In vivo maslinic acid treatment of mice fed with a high-fat diet reduced the model-associated adiposity and insulin resistance, and increased the accumulated hepatic glycogen content. In hyperglycemia mice, the elevation of blood glucose level caused by adrenaline or glucose was antagonized by maslinic acid significantly. Diabetic rats pretreated with high-dose maslinic acid had lower blood glucose levels, reduced infarct volumes and improved neurological scores. Less glutamate overflow was also observed in maslinic acid -treated rats after 2 hours of ischemia followed by 24 and 72 hours of reperfusion. In addition, maslinic acid treatment enhanced the glial glutamate transporter GLT-1 expression at the protein and mRNA levels. Direct beneficial effect in cerebral ischemic injury in rats may be correlated with the promotion of glutamate clearance by NF-κB-mediated GLT-1 up-regulation. Through NF-kappa B and MAPK/AP-1 signaling pathways maslinic acid suppresses RANKL-induced osteoclastogenesis as well.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28899728
Curator's Comment: Known to be CNS active in mouse. Human data not available
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2568 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21800347 |
6.91 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Anti-HIV triterpene acids from Geum japonicum. | 1996 Jul |
|
An efficient chemical method for separation of corsolic acid from its isomeric maslinic acid. | 2006 Aug |
|
Constituents of the flowers of Punica granatum. | 2006 Dec |
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Pentacyclic triterpenes. Part 2: Synthesis and biological evaluation of maslinic acid derivatives as glycogen phosphorylase inhibitors. | 2006 Feb |
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Production of triterpenoids in liquid-cultivated hairy roots of Galphimia glauca. | 2006 Jul |
|
New triterpenoids isolated from the root bark of Ulmus pumila L. | 2006 Jun |
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[Study on chemical constituents of Potentilla chinensis Ser]. | 2006 Mar |
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Supressive effect of maslinic acid from pomace olive oil on oxidative stress and cytokine production in stimulated murine macrophages. | 2006 Mar |
|
Triterpenic compounds from "orujo" olive oil elicit vasorelaxation in aorta from spontaneously hypertensive rats. | 2006 Mar 22 |
|
(2Alpha,3beta)-2,3-dihydroxyolean-12-en-28-oic acid, a new natural triterpene from Olea europea, induces caspase dependent apoptosis selectively in colon adenocarcinoma cells. | 2006 Nov 27 |
|
Maslinic acid as a feed additive to stimulate growth and hepatic protein-turnover rates in rainbow trout (Onchorhynchus mykiss). | 2006 Oct |
|
New glycosides from Tetracentron sinense and their cytotoxic activity. | 2006 Sep |
|
[Chemical constituents from root of Actinidia chinensis]. | 2007 Aug |
|
Antielastase and free radical scavenging activities of compounds from the stems of Cornus kousa. | 2007 Dec |
|
Production of triterpene acids by cell suspension cultures of Olea europaea. | 2007 May |
|
Triterpenoids isolated from apple peels have potent antiproliferative activity and may be partially responsible for apple's anticancer activity. | 2007 May 30 |
|
Maslinic acid reduces blood glucose in KK-Ay mice. | 2007 Nov |
|
Tyrosinase inhibitory pentacyclic triterpenes and analgesic and spasmolytic activities of methanol extracts of Rhododendron collettianum. | 2007 Nov |
|
Evaluation of gastroprotective activity of Plinia edulis (Vell.) Sobral (Myrtaceae) leaves in rats. | 2008 Aug 13 |
|
Antiproliferative and apoptosis-inducing effects of maslinic and oleanolic acids, two pentacyclic triterpenes from olives, on HT-29 colon cancer cells. | 2008 Jul |
|
Maslinic acid added to the diet increases growth and protein-turnover rates in the white muscle of rainbow trout (Oncorhynchus mykiss). | 2008 Mar |
|
[Triterpenoids and steroids of root of Rubus biflorus]. | 2008 Nov |
|
Practical synthesis of bredemolic acid, a natural inhibitor of glycogen phosphorylase. | 2008 Nov |
|
Solution- and solid-phase synthesis and anti-HIV activity of maslinic acid derivatives containing amino acids and peptides. | 2009 Feb 1 |
|
Natural triterpenic diols promote apoptosis in astrocytoma cells through ROS-mediated mitochondrial depolarization and JNK activation. | 2009 Jun 22 |
|
[Studies on chemical constituents of leaves of Psidium guajava]. | 2009 Mar |
|
Apolipoprotein E determines the hepatic transcriptional profile of dietary maslinic acid in mice. | 2009 Nov |
|
Fruit quality and olive leaf and stone addition affect Picual virgin olive oil triterpenic content. | 2009 Oct 14 |
|
[Determination of triterpenoid acids in leaves of Eriobotrya japonica collected at in different seasons]. | 2009 Sep |
|
Anticoccidial activity of maslinic acid against infection with Eimeria tenella in chickens. | 2010 Aug |
|
Chemical constituents with free-radical-scavenging activities from the stem of Microcos paniculata. | 2010 Aug 12 |
|
Bioactive compounds with added value prepared from terpenes contained in solid wastes from the olive oil industry. | 2010 Feb |
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Leucas aspera: A review. | 2010 Jan |
|
Total phenolic contents and antioxidant capacities of selected chinese medicinal plants. | 2010 Jun 1 |
|
Transformed cell suspension culture of Galphimia glauca producing sedative nor-friedelanes. | 2010 Mar |
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Targeting inflammatory pathways by triterpenoids for prevention and treatment of cancer. | 2010 Oct |
|
Pharmacological manipulation of brain glycogenolysis as a therapeutic approach to cerebral ischemia. | 2010 Oct |
|
Antioxidant and antiatherogenic activities of pentacyclic triterpenic diols and acids. | 2010 Oct |
|
Antimalarial evaluation of the chemical constituents of hairy root culture of Bixa orellana L. | 2014 Jan 8 |
|
Evaluation of pentacyclic triterpenes found in Perilla frutescens for inhibition of skin tumor promotion by 12-O-tetradecanoylphorbol-13-acetate. | 2015 Nov 17 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27770787
Consumption of 30 ml/day raw functional virgin olive oil inreached with triterpenic acids (389 mg/kg total, 218 mg/kg maslinic acid) in healthy volunteers (aged 20 to 50) over 3-week periods preceded by 2-week washout ones
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24863350
The IC50 of maslinic acid in HepG2 cells was 6.91 uM,
which was substantially lower than the IC50 of the positive
control compound (caffeine: 307 uM). Moreover, the inhibitory effect of maslinic acid on glycogen phosphorylase activity in the HepG2 cells was dose-dependent.
Substance Class |
Chemical
Created
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admin
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Edited
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Record UNII |
E233J88OHQ
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Record Status |
Validated (UNII)
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Record Version |
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73659
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8099
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66682
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Maslinic acid
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DTXSID30905074
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E233J88OHQ
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