Maslinic acid

Maslinic acid

Names
IUPAC name (4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-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
Systematic IUPAC name (2α,3β)-2,3-Dihydroxyolean-12-en-28-oic acid
Other names Crategolic acid; Masilinic acid; Crataegolic acid
Identifiers
CAS Number	4373-41-5
3D model (Jmol)	Interactive image
ChEBI	CHEBI:66682
ChEMBL	ChEMBL201515
ChemSpider	66312
ECHA InfoCard	100.128.873
KEGG	C16939
PubChem	73659
InChI 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 Key: MDZKJHQSJHYOHJ-LLICELPBSA-N 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 Key: MDZKJHQSJHYOHJ-LLICELPBBZ
SMILES 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
Chemical formula	C30H48O4
Molar mass	472.71 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.

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]

References

1. "Compound From Olive-pomace Oil Inhibits HIV Spread". sciencedaily.com. Retrieved 2009-06-16.
2. Juan ME, et al. (2008). "Antiproliferative and apoptosis-inducing effects of maslinic and oleanolic acids, two pentacyclic triterpenes from olives, on HT-29 colon cancer cells". Br J Nutr. 100 (1): 36–43. doi:10.1017/S0007114508882979. PMID 18298868.
3. Guan T, Qian Y, et al. (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.