Maslinic acid Chemical Properties

Melting point:

267～269℃

Boiling point:

570.0±50.0 °C(Predicted)

Density 

1.14±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

acetone: soluble1mg/mL, clear, colorless

pka

4.63±0.70(Predicted)

form 

powder

color 

white to off-white

Stability:

Hygroscopic

InChIKey

MDZKJHQSJHYOHJ-LLICELPBSA-N

SMILES

[C@@]12(C)CC[C@@]3([H])C(C)(C)[C@@H](O)[C@H](O)C[C@]3(C)[C@@]1([H])CC=C1[C@]3([H])CC(CC[C@]3(C(=O)O)CC[C@@]21C)(C)C |&1:0,4,9,11,14,16,21,27,33,r|

LogP

7.870 (est)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29181990

Hazardous Substances Data

4373-41-5(Hazardous Substances Data)

Maslinic acid Usage And Synthesis

Description

Maslinic acid (2-α,3-β-dihydroxyolean-12-en-28-oic acid) is a pentacyclic triterpene abundant in the cuticular lipid layer of olive fruits (Bianchi et al.，1994) .It is a compound of 30 carbon atoms grouped in five cycles that have several substitutes. Maslinic acid presents two hydroxyl groups bound to carbons 2 and 3,one carboxyl group bound to carbon 17, and a double bond between carbons 12 and 13.It is a highly hydrophobic compound of low water solubility. Maslinic acid is synthesized in plants via the cytoplasmic acetate/mevalonate pathway that leads to oxidosqualene (Seo et al., 1988).Oxidosqualene is cycled by various oxidosqualene cyclases, among them β-amyrin synthase, which catalyzes the transformation of oxydosqualene into β-amyrin (olean-12-3n-3β-ol). Afterwards,β-amyrin is converted by successive reactions into erythrodiol, oleanolic acid, and finally maslinic acid (Saimaru et al.,2007; Stiti et al.,2007).

Description

Maslinic acid is found in a number of natural sources, most notably pomace olive oil (orujo). This pentacyclic triterpene has an antiproliferative effect against Caco-2 cancer cells (EC₅₀ = 15 μM), HT-29 human colon cancer cells (EC₅₀ = 74 μM), 1321N1 astrocytoma cells (IC₅₀ = 25 μM), and human leukemia (CCRF-CEM and CEM/ADR5000) cells (IC₅₀ = 7 μM and 9 μM respectively). Maslinic acid''s antiproliferative activity likely comes from the induction of an oxidative apoptotic pathway, causing cell cycle and cytoskeleton alterations. Maslinic acid has been found to attenuate intracellular oxidative stress via inhibition of NO and H₂O₂ production and reduction of pro-inflammatory cytokine generation in murine macrophages. Recently maslinic acid has been found to inhibit the spread of the HIV virus by inhibiting the replication of a primary HIV-1 isolate as well as decreased the cytopathic effect and p24 antigen levels in MT2 cells.

Uses

Maslinic acid may be used as an analytical reference standard for the quantification of the analyte in the leaves of Ziziphus species and fruits using different chromatography techniques.

Uses

Maslinic Acid is an apoptosis inducer in lung cancer cells, occuring under normoxic and hypoxic conditions.

Definition

Maslinic acid is a pentacyclic triterpenoid that is olean-12-ene substituted by hydroxy groups at positions 2 and 3 and a carboxy group at position 28 (the 2alpha,3beta stereoisomer). It is isolated from Olea europaea and Salvia canariensis and exhibits anti-inflammatory, antioxidant and antineoplastic activity. It has a role as an antioxidant, an antineoplastic agent, an anti-inflammatory agent and a plant metabolite. It is a pentacyclic triterpenoid and a dihydroxy monocarboxylic acid. It derives from a hydride of an oleanane.

General Description

Maslinic acid belongs to the class of triterpenic acids, a group of phytochemicals present in a large variety of plants. It exhibits a broad-spectrum of biological properties such as cardiovascular, antihyperlipidemic, antioxidant effects, hepatoprotective effects, antitumor activity. It is also involved in enhancing the cellular immune system.

Biological Activity

Maslinic acid is found in a number of natural sources, most notably pomace olive oil (orujo). This pentacyclic triterpene has an antiproliferative effect against Caco-2 cancer cells (EC50 = 15 μM), HT-29 human colon cancer cells (EC50 = 74 μM), 1321N1 astrocytoma cells (IC50 = 25 μM), and human leukemia (CCRF-CEM and CEM/ADR5000) cells (IC50 = 7 μM and 9 μM respectively). Maslinic acid's antiproliferative activity likely comes from the induction of an oxidative apoptotic pathway, causing cell cycle and cytoskeleton alterations. Maslinic acid has been found to attenuate intracellular oxidative stress via inhibition of NO and H2O2 production and reduction of pro-inflammatory cytokine generation in murine macrophages. Recently maslinic acid has been found to inhibit the spread of the HIV virus by inhibiting the replication of a primary HIV-1 isolate as well as decreased the cytopathic effect and p24 antigen levels in MT2 cells.

Biochem/physiol Actions

Predominant triterpenoid found in olives. Anti-proliferative. Promising chemopreventive agent.

Cytotoxicity

IC₅₀ (μg/mL): 6.48 (518A2), 13.61(HT29),17.58 (MCF-7), 11.06 (A549), 9.22(A2780), 8.04 (8505C) (Siewert et al.2014)
IC₅₀ (μg/mL): 9.97 (NIH-3T3)(Sommerwerk et al. 2016).

References

[1] reyes-zurita f j, rufino-palomares e e, lupiáez j a, et al. maslinic acid, a natural triterpene from olea europaea l., induces apoptosis in ht29 human colon-cancer cells via the mitochondrial apoptotic pathway[j]. cancer letters, 2009, 273(1): 44-54.
[2] garcía, a. compound from olive-pomace oil inhibits hiv spread. 070709111536, 1-1 (2007).
[3] liu j, sun h, duan w, et al. maslinic acid reduces blood glucose in kk-ay mice[j]. biological and pharmaceutical bulletin, 2007, 30(11): 2075-2078.
[4] guan t, qian y, tang x, et al. maslinic acid, a natural inhibitor of glycogen phosphorylase, reduces cerebral ischemic injury in hyperglycemic rats by glt‐1 up‐regulation[j]. journal of neuroscience research, 2011, 89(11): 1829-1839.

Maslinic acid(4373-41-5)Related Product Information

• 4-Hydroxycinnamic acid
• Stearic acid
• 1,7-DIOXASPIRO[5.5]UNDECANE
• Citric acid
• Folic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Oleanolic acid
• Ascoric Acid
• Methyl maslinate
• Arjunolic acid
• (2α,3β)-2,3-Dihydroxy-olean-12-en-28-oic acid ethyl ester
• Maslinic acid
• (2α,3β)-2,3-Dihydroxy-olean-12-en-28-oic acid 2-hydroxyethyl ester,
• (2α,3β)- 2,3-Bis(acetyloxy)-olean- 12-en-28-oic acid
• 2,3-BIS(ACETYLOXY)-(2ALPHA,3BETA)-OLEAN-12-EN-28-OIC ACID METHYL ESTER
• (2α,3β)-2,3-Dihydroxy-olean-12-en-28-oic acid carboxymethyl ester
• 2-ACETYLOXY-3-HYDROXY-(2ALPHA,3BETA)-OLEAN-12-EN-28-OIC ACID METHYL ESTER
• (2α,3β)- 2-(Acetyloxy)-3-hydroxy- olean-12-en-28-oic acid