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
CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2C1)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 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
32.8 ng/mL |
30 mL single, oral dose: 30 mL route of administration: Oral experiment type: SINGLE co-administered: |
MASLINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
33.6 ng/mL |
30 mL single, oral dose: 30 mL route of administration: Oral experiment type: SINGLE co-administered: |
MASLINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
31.9 ng/mL |
30 mL single, oral dose: 30 mL route of administration: Oral experiment type: SINGLE co-administered: |
MASLINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
185.1 ng × h/mL |
30 mL single, oral dose: 30 mL route of administration: Oral experiment type: SINGLE co-administered: |
MASLINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
178.7 ng × h/mL |
30 mL single, oral dose: 30 mL route of administration: Oral experiment type: SINGLE co-administered: |
MASLINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
192.8 ng × h/mL |
30 mL single, oral dose: 30 mL route of administration: Oral experiment type: SINGLE co-administered: |
MASLINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.26 h |
30 mL single, oral dose: 30 mL route of administration: Oral experiment type: SINGLE co-administered: |
MASLINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
2.08 h |
30 mL single, oral dose: 30 mL route of administration: Oral experiment type: SINGLE co-administered: |
MASLINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
2.27 h |
30 mL single, oral dose: 30 mL route of administration: Oral experiment type: SINGLE co-administered: |
MASLINIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FED |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Evaluation of pentacyclic triterpenes found in Perilla frutescens for inhibition of skin tumor promotion by 12-O-tetradecanoylphorbol-13-acetate. | 2015-11-17 |
|
| Semi-synthesis of acylated triterpenes from olive-oil industry wastes for the development of anticancer and anti-HIV agents. | 2014-03-03 |
|
| Antimalarial evaluation of the chemical constituents of hairy root culture of Bixa orellana L. | 2014-01-08 |
|
| Multi-targeted activity of maslinic acid as an antimalarial natural compound. | 2011-08 |
|
| Parasitostatic effect of maslinic acid. I. Growth arrest of Plasmodium falciparum intraerythrocytic stages. | 2011-04-10 |
|
| Targeting inflammatory pathways by triterpenoids for prevention and treatment of cancer. | 2010-10 |
|
| Pharmacological manipulation of brain glycogenolysis as a therapeutic approach to cerebral ischemia. | 2010-10 |
|
| Antioxidant and antiatherogenic activities of pentacyclic triterpenic diols and acids. | 2010-10 |
|
| Pentacyclic triterpenoids from olive fruit and leaf. | 2010-09-08 |
|
| Chemical constituents with free-radical-scavenging activities from the stem of Microcos paniculata. | 2010-08-12 |
|
| Anticoccidial activity of maslinic acid against infection with Eimeria tenella in chickens. | 2010-08 |
|
| Total phenolic contents and antioxidant capacities of selected chinese medicinal plants. | 2010-06-01 |
|
| [Studies on the chemical constituents of Ficus microcarpa]. | 2010-06 |
|
| Action of a pentacyclic triterpenoid, maslinic acid, against Toxoplasma gondii. | 2010-05-28 |
|
| Chemopreventive properties of phytosterols and maslinic acid extracted from Coleus tuberosus in inhibiting the expression of EBV early-antigen in Raji cells. | 2010-05 |
|
| Maslinic acid potentiates the anti-tumor activity of tumor necrosis factor alpha by inhibiting NF-kappaB signaling pathway. | 2010-04-06 |
|
| Transformed cell suspension culture of Galphimia glauca producing sedative nor-friedelanes. | 2010-03 |
|
| Bioactive compounds with added value prepared from terpenes contained in solid wastes from the olive oil industry. | 2010-02 |
|
| Leucas aspera: A review. | 2010-01 |
|
| Different pathways for the deoxygenation of the A-ring of natural triterpene compounds. | 2010 |
|
| Synthesis and biological evaluation of heterocyclic ring-substituted maslinic acid derivatives as novel inhibitors of protein tyrosine phosphatase 1B. | 2009-12-01 |
|
| Apolipoprotein E determines the hepatic transcriptional profile of dietary maslinic acid in mice. | 2009-11 |
|
| Fruit quality and olive leaf and stone addition affect Picual virgin olive oil triterpenic content. | 2009-10-14 |
|
| [Chemical constituents of roots of Boehmeria nivea]. | 2009-10 |
|
| [Determination of triterpenoid acids in leaves of Eriobotrya japonica collected at in different seasons]. | 2009-09 |
|
| Effects of maslinic acid, a natural triterpene, on glycogen metabolism in cultured cortical astrocytes. | 2009-08 |
|
| Natural triterpenic diols promote apoptosis in astrocytoma cells through ROS-mediated mitochondrial depolarization and JNK activation. | 2009-06-22 |
|
| Triterpenic content and chemometric analysis of virgin olive oils from forty olive cultivars. | 2009-05-13 |
|
| Novel binding studies of human serum albumin with trans-feruloyl maslinic acid. | 2009-05-04 |
|
| Triterpene acids isolated from Lagerstroemia speciosa leaves as alpha-glucosidase inhibitors. | 2009-05 |
|
| [Studies on chemical constituents of leaves of Psidium guajava]. | 2009-03 |
|
| Solution- and solid-phase synthesis and anti-HIV activity of maslinic acid derivatives containing amino acids and peptides. | 2009-02-01 |
|
| Maslinic acid, a natural triterpene from Olea europaea L., induces apoptosis in HT29 human colon-cancer cells via the mitochondrial apoptotic pathway. | 2009-01-08 |
|
| [Chemical constituents from herbs of Swertia mileensis]. | 2008-12 |
|
| Triterpenoic acids of Prunella vulgaris var. lilacina and their cytotoxic activities in vitro. | 2008-12 |
|
| [Triterpenoids and steroids of root of Rubus biflorus]. | 2008-11 |
|
| Medicinal flowers. XXIII. New taraxastane-type triterpene, punicanolic acid, with tumor necrosis factor-alpha inhibitory activity from the flowers of Punica granatum. | 2008-11 |
|
| Practical synthesis of bredemolic acid, a natural inhibitor of glycogen phosphorylase. | 2008-11 |
|
| [Studies on the triterpenes from loquat leaf (Eriobotrya japonica)]. | 2008-09 |
|
| Evaluation of gastroprotective activity of Plinia edulis (Vell.) Sobral (Myrtaceae) leaves in rats. | 2008-08-13 |
|
| Antiproliferative and apoptosis-inducing effects of maslinic and oleanolic acids, two pentacyclic triterpenes from olives, on HT-29 colon cancer cells. | 2008-07 |
|
| Naturally occurring pentacyclic triterpenes as inhibitors of glycogen phosphorylase: synthesis, structure-activity relationships, and X-ray crystallographic studies. | 2008-06-26 |
|
| Maslinic acid added to the diet increases growth and protein-turnover rates in the white muscle of rainbow trout (Oncorhynchus mykiss). | 2008-03 |
|
| Aldose-reductase- and protein-glycation-inhibitory principles from the whole plant of Duchesnea chrysantha. | 2008-02 |
|
| Anti-inflammatory and antioxidant activities and constituents of Platostoma africanum P. Beauv. | 2008 |
|
| Antielastase and free radical scavenging activities of compounds from the stems of Cornus kousa. | 2007-12 |
|
| Maslinic acid reduces blood glucose in KK-Ay mice. | 2007-11 |
|
| Bioactivity-guided isolation of the active compounds from Rosa nutkana and quantitative analysis of ascorbic acid by HPLC. | 2007-09 |
|
| [Chemical constituents from root of Actinidia chinensis]. | 2007-08 |
|
| Anti-HIV triterpene acids from Geum japonicum. | 1996-07 |
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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| Record UNII |
E233J88OHQ
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| Record Status |
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Maslinic acid
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