Maslinic acid

Last updated
Maslinic acid
Maslinic-acid-structure.png
Names
IUPAC name
2α,3β-Dihydroxyolean-12-en-28-oic acid
Systematic IUPAC name
(4aS,6aS,6bR,8aR,10R,11R,12aR,12bR,14bS)-10,11-Dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid
Other names
Crategolic acid; Masilinic acid; Crataegolic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.128.873 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • 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 X mark.svgN
    Key: MDZKJHQSJHYOHJ-LLICELPBSA-N X mark.svgN
  • CC1(C)[C@@H](O)[C@H](O)C[C@@]2(C)[C@]([H])1CC[C@]3(C)[C@@]([H])2CC=C4[C@](C)3CC[C@]5([C@](O)=O)[C@]([H])4CC(C)(C)CC5
Properties
C30H48O4
Molar mass 472.710 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Maslinic acid is a compound derived from dry olive-pomace oil (an olive skin wax) which is a byproduct of olive oil extraction. It is a member of the group of triterpenes known as oleananes.

Contents

Pharmacology

In vitro study shows that maslinic acid inhibits serine proteases, key enzymes necessary for the spread of HIV within an individual's body. [1] It also has in vitro antiproliferative effects on colon cancer cells. [2] Maslinic acid increases EAAT2 (GLT-1) glutamate reuptake and may reduce glutamatergic toxicity in rats. [3] Additionally, maslinic acid serves as a glycogen phosphorylase inhibitor in mouse liver, [4] [5] as evidenced by increased glycogen accumulation in rainbow trout liver. [6]

Clinical significance

Maslinic acid demonstrates antioxidant capabilities against oxygen and nitrogen reactive species. [7] [8] It also exhibits a suppressive impact on proinflammatory cytokines like TNF-α and IL-6 in murine macrophages. [8] These mechanisms could contribute to enhanced protein synthesis, growth rates, and joint support. [9] Maslinic acid has been shown to improve muscle mass in the elderly when combined with resistance exercise. [10]

Related Research Articles

<span class="mw-page-title-main">Glycogen phosphorylase</span> Class of enzymes

Glycogen phosphorylase is one of the phosphorylase enzymes. Glycogen phosphorylase catalyzes the rate-limiting step in glycogenolysis in animals by releasing glucose-1-phosphate from the terminal alpha-1,4-glycosidic bond. Glycogen phosphorylase is also studied as a model protein regulated by both reversible phosphorylation and allosteric effects.

<span class="mw-page-title-main">Oleocanthal</span> Chemical compound

Oleocanthal is a phenylethanoid, or a type of natural phenolic compound found in extra-virgin olive oil. It appears to be responsible for the burning sensation that occurs in the back of the throat when consuming such oil. Oleocanthal is a tyrosol ester and its chemical structure is related to oleuropein, also found in olive oil.

<span class="mw-page-title-main">Myricetin</span> Chemical compound

Myricetin is a member of the flavonoid class of polyphenolic compounds, with antioxidant properties. Common dietary sources include vegetables, fruits, nuts, berries, tea, and red wine.

<span class="mw-page-title-main">Moronic acid</span> Chemical compound

Moronic acid is a natural triterpene. Moronic acid can be extracted from Rhus javanica, a sumac plant traditionally believed to hold medicinal applications. The molecule has also been extracted from mistletoe.

<span class="mw-page-title-main">Triterpene</span> Class of chemical compounds

Triterpenes are a class of terpenes composed of six isoprene units with the molecular formula C30H48; they may also be thought of as consisting of three terpene units. Animals, plants and fungi all produce triterpenes, including squalene, the precursor to all steroids.

<span class="mw-page-title-main">Boswellic acid</span> Chemical compound

Boswellic acids are a series of pentacyclic terpenoid molecules that are produced by plants in the genus Boswellia. Like many other terpenes, boswellic acids appear in the resin of the plant that exudes them; it is estimated that they make up 30% of the resin of Boswellia serrata. While boswellic acids are a major component of the resin, the steam or hydro distilled frankincense essential oil does not contain any boswellic acid as these components are non-volatile and too large to come over in the steam distillation process.

Chemokine ligand 1 (CCL1) is also known as small inducible cytokine A1 and I-309 in humans. CCL1 is a small glycoprotein that belongs to the CC chemokine family.

<span class="mw-page-title-main">Mitraphylline</span> Chemical compound

Mitraphylline, an oxindole derivative, is an active alkaloid in the leaves of the tree Mitragyna speciosa, commonly known as kratom. As a non-narcotic constituent, it also occurs to a significant amount in the bark of Uncaria tomentosa along with a number of isomeric alkaloids.

<span class="mw-page-title-main">Oleanolic acid</span> Pentacyclic chemical compound in plant leaves and fruit

Oleanolic acid or oleanic acid is a naturally occurring pentacyclic triterpenoid related to betulinic acid. It is widely distributed in food and plants where it exists as a free acid or as an aglycone of triterpenoid saponins.

<span class="mw-page-title-main">Depside</span> Class of chemical compounds

A depside is a type of polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester group. Depsides are most often found in lichens, but have also been isolated from higher plants, including species of the Ericaceae, Lamiaceae, Papaveraceae and Myrtaceae.

<span class="mw-page-title-main">Protein phosphatase 1</span>

Protein phosphatase 1 (PP1) belongs to a certain class of phosphatases known as protein serine/threonine phosphatases. This type of phosphatase includes metal-dependent protein phosphatases (PPMs) and aspartate-based phosphatases. PP1 has been found to be important in the control of glycogen metabolism, muscle contraction, cell progression, neuronal activities, splicing of RNA, mitosis, cell division, apoptosis, protein synthesis, and regulation of membrane receptors and channels.

<i>Croton lechleri</i> Species of plant

Croton lechleri is a species of flowering plant in the spurge family, Euphorbiaceae, that is native to northwestern South America. It is commonly known as sangre de grado, sangre de drago or sangre de grada. They refer to this tree's thick red latex.

<span class="mw-page-title-main">Amyrin</span> Chemical compound

The amyrins are three closely related natural chemical compounds of the triterpene class. They are designated α-amyrin (ursane skeleton), β-amyrin (oleanane skeleton) and δ-amyrin. Each is a pentacyclic triterpenol with the chemical formula C30H50O. They are widely distributed in nature and have been isolated from a variety of plant sources such as epicuticular wax. In plant biosynthesis, α-amyrin is the precursor of ursolic acid and β-amyrin is the precursor of oleanolic acid. All three amyrins occur in the surface wax of tomato fruit. α-Amyrin is found in dandelion coffee.

<span class="mw-page-title-main">Cucurbitacin E</span> Chemical compound

Cucurbitacin E is a biochemical compound from the family of cucurbitacins. These are found in plants which are member of the family Cucurbitaceae, most of them coming from traditional Chinese medicinal plants, but also in other plants such as pumpkins and gourds.

α-Hederin Chemical compound

α-Hederin (alpha-hederin) is a water-soluble pentacyclic triterpenoid saponin found in the seeds of Nigella sativa and leaves of Hedera helix.

<span class="mw-page-title-main">Nyasol</span> Chemical compound

Nyasol, also known as cis-hinokiresinol or as (Z)-hinokiresinol, is a lignan that is found in Anemarrhena asphodeloides. It has estrogenic activity, acting as a selective agonist of the ERβ, and hence is a phytoestrogen. In addition, (-)-nyasol has been found to inhibit the production of eicosanoids and nitric oxide in vitro and shows anti-inflammatory effects.

<span class="mw-page-title-main">Hinokinin</span> Chemical compound

Hinokinin is a dibenzylbutyrolactone lignan, derived from various species of plants. It is a potential antichagonistic agent and has shown to possess neuroprotective effects as well. It is also found to have anti-inflammatory, anti-cancer, antiviral and antifungal properties.

<i>Ferula narthex</i> Species of plant

Ferula narthex is a species of plant native to Afghanistan, Tajikistan, northern Pakistan and Kashmir. Although it is often listed as the source of asafoetida, one report stated that its essential oil lacked sulfur-containing compounds which are characteristic of asafoetida.

<span class="mw-page-title-main">Gedunin</span> Chemical compound

Gedunin is a pentacyclic triterpenoid with the molecular formula C28H34 O7. It is most notably found in Azadirachta indica, but is a constituent of several other plants. Gedunin shows therapeutic potential in the treatment of leukemia, and Parkinson's disease.

<i>Cussonia arborea</i> Species of plant

Cussonia arborea is a deciduous small to medium sized tree within the family Araliaceae. Extracts of the species are widely used in traditional medicine to treat a variety of ailments.

References

  1. University of Granada (11 July 2007). "Compound From Olive-pomace Oil Inhibits HIV Spread". sciencedaily.com. Retrieved 2009-06-16.
  2. Juan ME, Planas JM, Ruiz-Gutierrez V, Daniel H, Wenzel U (2008). "Antiproliferative and apoptosis-inducing effects of maslinic and oleanolic acids, two pentacyclic triterpenes from olives, on HT-29 colon cancer cells" (PDF). Br J Nutr. 100 (1): 36–43. doi: 10.1017/S0007114508882979 . PMID   18298868.
  3. Guan T, Qian Y, Guan T, Qian Y, Tang X, Huang M, Huang L, Li Y, Sun M (November 2011). "Maslinic acid, a natural inhibitor of glycogen phosphorylase, reduces cerebral ischemic injury in hyperglycemic rats by GLT-1 up-regulation". J. Neurosci. Res. 89 (11): 1829–39. doi: 10.1002/jnr.22671 . PMID   21800347.
  4. Márquez Martín A, De La Puerta Vázquez R, Fernández-Arche A, Ruiz-Gutiérrez V (2006). "Supressive effect of maslinic acid from pomace olive oil on oxidative stress and cytokine production in stimulated murine macrophages". Free Radical Research. 40 (3): 295–302. doi:10.1080/10715760500467935. ISSN   1071-5762. PMID   16484046.
  5. Wen X, Sun H, Liu J, Wu G, Zhang L, Wu X, Ni P (2005-11-15). "Pentacyclic triterpenes. Part 1: The first examples of naturally occurring pentacyclic triterpenes as a new class of inhibitors of glycogen phosphorylases". Bioorganic & Medicinal Chemistry Letters. 15 (22): 4944–4948. doi:10.1016/j.bmcl.2005.08.026. ISSN   0960-894X. PMID   16169219.
  6. Vlietinck A, De Bruyne T, Apers S, Pieters L (1998). "Plant-Derived Leading Compounds for Chemotherapy of Human Immunodeficiency Virus (HIV) Infection" (PDF). Planta Medica. 64 (02): 97–109. doi: 10.1055/s-2006-957384 . ISSN   0032-0943. PMID   9525100.
  7. Conlon, Ian; Raff, Martin (1999-01-22). "Size Control in Animal Development". Cell. 96 (2): 235–244. doi: 10.1016/S0092-8674(00)80563-2 . PMID   9988218.
  8. 1 2 Montilla MP, Agil A, Navarro MC, Jiménez MI, García-Granados A, Parra A, Cabo MM (2003). "Antioxidant Activity of Maslinic Acid, a Triterpene Derivative Obtained from Olea europaea". Planta Medica. 69 (5): 472–474. doi:10.1055/s-2003-39698. ISSN   0032-0943. PMID   12802735.
  9. Nierding, Axel. "Acide Maslinique: Propriétés Et Bienfaits" [Maslinic Acid: Properties And Benefits]. Polyvalents (in French). Retrieved 2023-12-25.
  10. Nagai N, Yagyu S, Sakane N (2019). "Maslinic acid derived from olive fruit in combination with resistance training improves muscle mass and mobility functions in the elderly". Journal of Clinical Biochemistry and Nutrition. 64 (3): 224–230. doi:10.3164/jcbn.18-104. PMC   6529705 . PMID   31138956.