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 |
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Anti-HIV triterpene acids from Geum japonicum. | 1996 Jul |
|
[Studies on chemical constituents in fruit of Rubus chingii]. | 2005 Feb |
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Pentacyclic triterpenes. Part 1: the first examples of naturally occurring pentacyclic triterpenes as a new class of inhibitors of glycogen phosphorylases. | 2005 Nov 15 |
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Secondary metabolites from the wood bark of Durio zibethinus and Durio kutejensis. | 2006 Aug |
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Diterpenes from Leucas aspera inhibiting prostaglandin-induced contractions. | 2006 Jul |
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[Triterpenes from herb of Potentilla chinesis]. | 2006 Nov |
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(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 |
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Maslinic acid as a feed additive to stimulate growth and hepatic protein-turnover rates in rainbow trout (Onchorhynchus mykiss). | 2006 Oct |
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New glycosides from Tetracentron sinense and their cytotoxic activity. | 2006 Sep |
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[Chemical constituents from root of Actinidia chinensis]. | 2007 Aug |
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Formation of triterpenoids throughout Olea europaea fruit ontogeny. | 2007 Feb |
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Maslinic acid reduces blood glucose in KK-Ay mice. | 2007 Nov |
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Tyrosinase inhibitory pentacyclic triterpenes and analgesic and spasmolytic activities of methanol extracts of Rhododendron collettianum. | 2007 Nov |
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Bioactivity-guided isolation of the active compounds from Rosa nutkana and quantitative analysis of ascorbic acid by HPLC. | 2007 Sep |
|
Aldose-reductase- and protein-glycation-inhibitory principles from the whole plant of Duchesnea chrysantha. | 2008 Feb |
|
Maslinic acid added to the diet increases growth and protein-turnover rates in the white muscle of rainbow trout (Oncorhynchus mykiss). | 2008 Mar |
|
[Studies on the triterpenes from loquat leaf (Eriobotrya japonica)]. | 2008 Sep |
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Synthesis and biological evaluation of heterocyclic ring-substituted maslinic acid derivatives as novel inhibitors of protein tyrosine phosphatase 1B. | 2009 Dec 1 |
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[Chemical constituents of roots of Boehmeria nivea]. | 2009 Oct |
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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 |
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Different pathways for the deoxygenation of the A-ring of natural triterpene compounds. | 2010 |
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Leucas aspera: A review. | 2010 Jan |
|
[Studies on the chemical constituents of Ficus microcarpa]. | 2010 Jun |
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Parasitostatic effect of maslinic acid. I. Growth arrest of Plasmodium falciparum intraerythrocytic stages. | 2011 Apr 10 |
|
Antimalarial evaluation of the chemical constituents of hairy root culture of Bixa orellana L. | 2014 Jan 8 |
|
Semi-synthesis of acylated triterpenes from olive-oil industry wastes for the development of anticancer and anti-HIV agents. | 2014 Mar 3 |
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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
on
Edited
Sat Dec 16 08:13:44 GMT 2023
by
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Sat Dec 16 08:13:44 GMT 2023
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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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Maslinic acid
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DTXSID30905074
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E233J88OHQ
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