4373-41-5 Usage
Description
Maslinic acid, scientifically known as 2-α,3-β-dihydroxyolean-12-en-28-oic acid, is a pentacyclic triterpene compound found abundantly in the cuticular lipid layer of olive fruits. It consists of 30 carbon atoms arranged in five cycles with various substitutes, featuring two hydroxyl groups bound to carbons 2 and 3, a carboxyl group bound to carbon 17, and a double bond between carbons 12 and 13. Maslinic acid is highly hydrophobic and has low water solubility. It is synthesized in plants through the cytoplasmic acetate/mevalonate pathway, which leads to oxidosqualene and is then transformed into β-amyrin, erythrodiol, oleanolic acid, and finally maslinic acid.
Uses
Used in Pharmaceutical Industry:
Maslinic acid is used as an antiproliferative agent for its potential anticancer properties. It has demonstrated an antiproliferative effect against various cancer cells, including Caco-2, HT-29 human colon cancer cells, 1321N1 astrocytoma cells, and human leukemia cells. Its antiproliferative activity is believed to stem from the induction of an oxidative apoptotic pathway, leading to cell cycle and cytoskeleton alterations.
Used in Analytical Chemistry:
Maslinic acid serves as an analytical reference standard for the quantification of the analyte in the leaves of Ziziphus species and fruits using different chromatography techniques.
Used in Antiviral Applications:
Maslinic acid is used as an inhibitor of the HIV virus, as it has been found to inhibit the replication of a primary HIV-1 isolate, decrease the cytopathic effect, and reduce p24 antigen levels in MT2 cells.
Used in Anti-inflammatory Applications:
Maslinic acid is used as an anti-inflammatory agent, as it has been found to attenuate intracellular oxidative stress via the inhibition of NO and H2O2 production and reduction of pro-inflammatory cytokine generation in murine macrophages.
Used in Apoptosis Induction:
Maslinic acid is used as an apoptosis inducer in lung cancer cells, effective under both normoxic and hypoxic conditions.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 4373-41-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,3,7 and 3 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 4373-41:
(6*4)+(5*3)+(4*7)+(3*3)+(2*4)+(1*1)=85
85 % 10 = 5
So 4373-41-5 is a valid CAS Registry Number.
InChI:InChI=1/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
4373-41-5Relevant articles and documents
Straightforward partial synthesis of four diastereomeric 2,3-dihydroxy-olean-12-en-28-oic acids from oleanolic acid
Sommerwerk, Sven,Heller, Lucie,Serbian, Immo,Csuk, René
, p. 8528 - 8534 (2016/02/03)
The four diastereomeric 2,3-dihydroxy-olean-12-en-28-oic acids (maslinic, augustic, bredemolic and 3-epi-maslinic acid) were easily accessed from one single starting material, oleanolic acid. The procedures allow the medium-to-large scale preparation of these valuable starting materials. Except for maslinic acid, the triterpenoic acids showed only a low cytotoxicity towards several human tumor cell lines.
Convenient and chromatography-free partial syntheses of maslinic acid and augustic acid
Sommerwerk, Sven,Csuk, René
, p. 5156 - 5158 (2014/12/11)
A convenient and chromatography-free 4-step synthesis of analytically pure maslinic acid (1, 41.2%) from oleanolic acid has been developed. Slight variations in the final steps gave an excellent yield of isomeric augustic acid (7, 71.9%).
Semi-synthesis of acylated triterpenes from olive-oil industry wastes for the development of anticancer and anti-HIV agents
Parra, Andres,Martin-Fonseca, Samuel,Rivas, Francisco,Reyes-Zurita, Fernando J.,Medina-O'Donnell, Marta,Martinez, Antonio,Garcia-Granados, Andres,Lupia?ez, Jose A.,Albericio, Fernando
, p. 278 - 301 (2014/02/14)
A broad set of potential bioactive conjugate compounds has been semi-synthesized through solution- and solid-phase organic procedures, coupling two natural pentacyclic triterpene acids, oleanolic (OA) and maslinic acids (MA), at the hydroxyl groups of the A-ring of the triterpene skeleton, with 10 different acyl groups. These acyl OA and MA derivatives have been tested for their anti-proliferative (against the b16f10 murine melanoma cancer cells) and antiviral (as inhibitors of the HIV-1-protease) effects. Several derivatives have shown high levels of early and total apoptosis (up to 90%). Most of the compounds that exhibited anti-proliferative effects also generated ROS, probably involving the activation of an intrinsic apoptotic route. The only four compounds that did not cause the release of ROS could be related to the participation of a probable extrinsic activation of the apoptosis mechanism. A great number of these acyl OA and MA derivatives have proved to be potent inhibitors of the HIV-1-protease, the most active inhibitors having IC 50 values between 0.31 and 15.6 μM, these values being between 4 and 186 times lower than their non-acylated precursors. The potent activities exhibited in the apoptosis-activation processes and in the inhibition of the HIV-1-protease by some OA and MA acylated derivatives imply that these compounds could be used as new, safe, and effective anticancer and/or antiviral drugs.
