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Latest revision as of 01:30, 12 July 2024 edit undoحسن علي البط (talk | contribs)Extended confirmed users, Pending changes reviewers19,940 edits added Category:Pentacyclic compounds using HotCat |
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{{chembox |
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|ImageFile=Maslinic-acid-structure.png |
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|ImageSize=200px |
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| verifiedrevid = 373368435 |
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|IUPACName=(4a''S'',6a''R'',6a''S'',6b''R'',8a''R'',10''R'',11''R'',12a''R'',14b''S'')-10,11-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid |
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| ImageFile = Maslinic-acid-structure.png |
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|OtherNames= |
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| ImageSize = 300px |
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| IUPACName = 2α,3β-Dihydroxyolean-12-en-28-oic acid |
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| SystematicName = (4a''S'',6a''S'',6b''R'',8a''R'',10''R'',11''R'',12a''R'',12b''R'',14b''S'')-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(2''H'')-carboxylic acid |
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| OtherNames = Crategolic acid; Masilinic acid; Crataegolic acid |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo=4373-41-5 |
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| CASNo = 4373-41-5 |
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| PubChem=73659 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES=CC1(C)(O)(O)C2(C)()1CC3(C)()2CC=C4(C)3CC5((O)=O)()4CC(C)(C)CC5 |
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| UNII = E233J88OHQ |
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| PubChem = 73659 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 66682 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 201515 |
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| SMILES=CC1(C)(O)(O)C2(C)()1CC3(C)()2CC=C4(C)3CC5((O)=O)()4CC(C)(C)CC5 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 66312 |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 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 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = MDZKJHQSJHYOHJ-LLICELPBSA-N |
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| KEGG = C16939 |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=30 |
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| Formula=C<sub>30</sub>H<sub>48</sub>O<sub>4</sub> |
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| H=48 |
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| MolarMass=472.70 g/mol |
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| O=4 |
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'''Maslinic acid''' is a compound derived from dry olive-pomace oil (an olive skin wax) which is a byproduct of ]. It is a member of the group of ]s known as oleananes. |
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'''Maslinic acid''' is a compound derived from dry olive-pomace oil (an olive skin wax) which is a byproduct of ]. It is a member of the group of ]s known as ]s. |
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==Pharmacology== |
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==Biological activities== |
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'']'' study shows that maslinic acid ] ]s, key enzymes necessary for the spread of ] within an individual's body.<ref>{{cite news |author=University of Granada |date=11 July 2007 |title=Compound From Olive-pomace Oil Inhibits HIV Spread |website=sciencedaily.com| url=https://www.sciencedaily.com/releases/2007/07/070709111536.htm |access-date=2009-06-16}}</ref> It also has ''in vitro'' ] effects on colon cancer cells.<ref>{{cite journal |vauthors=Juan ME, Planas JM, Ruiz-Gutierrez V, Daniel H, Wenzel U |title=Antiproliferative and apoptosis-inducing effects of maslinic and oleanolic acids, two pentacyclic triterpenes from olives, on HT-29 colon cancer cells |journal=Br J Nutr |year=2008 |volume=100 |issue=1 |pages=36–43 |doi=10.1017/S0007114508882979 |pmid=18298868| url=https://digital.csic.es/bitstream/10261/53542/1/HT-29.pdf |doi-access=free}}</ref> Maslinic acid increases ] (GLT-1) glutamate reuptake and may reduce glutamatergic toxicity in rats.<ref>{{cite journal |vauthors=Guan T, Qian Y, Guan T, Qian Y, Tang X, Huang M, Huang L, Li Y, Sun M |title=Maslinic acid, a natural inhibitor of glycogen phosphorylase, reduces cerebral ischemic injury in hyperglycemic rats by GLT-1 up-regulation |journal=J. Neurosci. Res. |date=November 2011 |volume=89 |issue=11 |pages=1829–39 |doi=10.1002/jnr.22671 |pmid=21800347|doi-access=free }}</ref> Additionally, maslinic acid serves as a glycogen phosphorylase inhibitor in mouse liver,<ref>{{Cite journal |vauthors=Márquez Martín A, De La Puerta Vázquez R, Fernández-Arche A, Ruiz-Gutiérrez V |date=2006 |title=Supressive effect of maslinic acid from pomace olive oil on oxidative stress and cytokine production in stimulated murine macrophages |journal=Free Radical Research |language=en |volume=40 |issue=3 |pages=295–302 |doi=10.1080/10715760500467935 |issn=1071-5762 |pmid=16484046}}</ref><ref>{{Cite journal |vauthors=Wen X, Sun H, Liu J, Wu G, Zhang L, Wu X, Ni P |date=2005-11-15 |title=Pentacyclic triterpenes. Part 1: The first examples of naturally occurring pentacyclic triterpenes as a new class of inhibitors of glycogen phosphorylases |journal=Bioorganic & Medicinal Chemistry Letters |volume=15 |issue=22 |pages=4944–4948 |doi=10.1016/j.bmcl.2005.08.026 |issn=0960-894X |pmid=16169219}}</ref> as evidenced by increased glycogen accumulation in rainbow trout liver.<ref>{{Cite journal |vauthors=Vlietinck A, De Bruyne T, Apers S, Pieters L |date=1998 |title=Plant-Derived Leading Compounds for Chemotherapy of Human Immunodeficiency Virus (HIV) Infection |url=https://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2006-957384.pdf |journal=Planta Medica |language=en |volume=64 |issue=02 |pages=97–109 |doi=10.1055/s-2006-957384 |doi-access=free |issn=0032-0943 |pmid=9525100}}</ref> |
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Research at the ] and Hospital Carlos III in Madrid indicates that maslinic acid ] ]s, key enzymes necessary for the spread of ] within an individual's body.<ref>{{cite news | first= | last= | coauthors= | title=Compound From Olive-pomace Oil Inhibits HIV Spread | date= | publisher= sciencedaily.com| url =http://www.sciencedaily.com/releases/2007/07/070709111536.htm | work = | pages = | accessdate = 2009-06-16 | language = }}</ref> |
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==Clinical significance== |
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Also, research at the University of Barcelona suggests that maslinic acid may prevent colon cancer by acting as an antiproliferative of colon cancer cells.<ref>{{cite journal | author = Juan ME, et al. | title = Antiproliferative and apoptosis-inducing effects of maslinic and oleanolic acids, two pentacyclic triterpenes from olives, on HT-29 colon cancer cells | journal = Br J Nutr | year = 2008 | volume = 100 | issue = 1 | pages = 36–43 | doi = 10.1017/S0007114508882979 | pmid = 18298868}}</ref> |
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Maslinic acid demonstrates antioxidant capabilities against oxygen and nitrogen reactive species.<ref>{{Cite journal |last=Conlon |first=Ian |last2=Raff |first2=Martin |date=1999-01-22 |title=Size Control in Animal Development |journal=Cell |language=en |volume=96 |issue=2 |pages=235–244 |pmid=9988218 |doi=10.1016/S0092-8674(00)80563-2 |doi-access=free}}</ref><ref name="montilla">{{Cite journal |vauthors=Montilla MP, Agil A, Navarro MC, Jiménez MI, García-Granados A, Parra A, Cabo MM |date=2003 |title=Antioxidant Activity of Maslinic Acid, a Triterpene Derivative Obtained from Olea europaea |journal=Planta Medica |language=en |volume=69 |issue=5 |pages=472–474 |doi=10.1055/s-2003-39698 |issn=0032-0943 |pmid=12802735}}</ref> It also exhibits a suppressive impact on proinflammatory cytokines like TNF-α and IL-6 in murine macrophages.<ref name="montilla" /> These mechanisms could contribute to enhanced protein synthesis, growth rates, and joint support.<ref>{{cite web |title=Acide Maslinique: Propriétés Et Bienfaits |trans-title=Maslinic Acid: Properties And Benefits |language=fr |last=Nierding |first=Axel |website=Polyvalents |url=https://polyvalents.fr/acide-maslinique/ |access-date=2023-12-25}}</ref> Maslinic acid has been shown to improve muscle mass in the elderly when combined with ].<ref name="pmid31138956">{{cite journal | vauthors = Nagai N, Yagyu S, Sakane N | title=Maslinic acid derived from olive fruit in combination with resistance training improves muscle mass and mobility functions in the elderly | journal=Journal of Clinical Biochemistry and Nutrition | volume=64 | issue=3 | pages=224-230 | year=2019 | doi= 10.3164/jcbn.18-104 | pmc=6529705 | pmid=31138956}}</ref> |
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==References== |
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