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
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 |
---|---|---|
Antitumor-promoting constituents from Chaenomeles sinensis KOEHNE and their activities in JB6 mouse epidermal cells. | 2003 Nov |
|
Secondary metabolites from the wood bark of Durio zibethinus and Durio kutejensis. | 2006 Aug |
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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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Maslinic acid as a feed additive to stimulate growth and hepatic protein-turnover rates in rainbow trout (Onchorhynchus mykiss). | 2006 Oct |
|
[Chemical constituents from root of Actinidia chinensis]. | 2007 Aug |
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Bioactivity-guided isolation of the active compounds from Rosa nutkana and quantitative analysis of ascorbic acid by HPLC. | 2007 Sep |
|
Anti-inflammatory and antioxidant activities and constituents of Platostoma africanum P. Beauv. | 2008 |
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Evaluation of gastroprotective activity of Plinia edulis (Vell.) Sobral (Myrtaceae) leaves in rats. | 2008 Aug 13 |
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Antiproliferative and apoptosis-inducing effects of maslinic and oleanolic acids, two pentacyclic triterpenes from olives, on HT-29 colon cancer cells. | 2008 Jul |
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Naturally occurring pentacyclic triterpenes as inhibitors of glycogen phosphorylase: synthesis, structure-activity relationships, and X-ray crystallographic studies. | 2008 Jun 26 |
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Practical synthesis of bredemolic acid, a natural inhibitor of glycogen phosphorylase. | 2008 Nov |
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Natural triterpenic diols promote apoptosis in astrocytoma cells through ROS-mediated mitochondrial depolarization and JNK activation. | 2009 Jun 22 |
|
[Chemical constituents of roots of Boehmeria nivea]. | 2009 Oct |
|
[Determination of triterpenoid acids in leaves of Eriobotrya japonica collected at in different seasons]. | 2009 Sep |
|
Pharmacological manipulation of brain glycogenolysis as a therapeutic approach to cerebral ischemia. | 2010 Oct |
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.
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4373-41-5
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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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SUBSTANCE RECORD