Triterpenes oleanolic acid

Cloves contain about 2% of the triterpene, oleanolic acid. Narayanan and Natu (1974) isolated maslinic acid from clove buds. From clove, 2a-hydroxyoleanolic acid was isolated by Brieskorn et al. (1975). 

The triterpenes oleanolic acid, ursolic acid 10 and 1-4 were isolated from fraction III. All pure compounds, tested by the same procedure, were inactive. Since the tested doses were very low (ranging from 0.04 mg/Kg to 0.51 mg/Kg), a further set of experiments was performed at higher doses (0.014 mmol of each compound/Kg, equivalent to the ED50 of indomethacin) however no significant inhibition of the edema was seen, although the control, indomethacin (5mg/Kg po), was active. 

Figure 5.1 Structures of the pure triterpenes studied by GALDI MS hydroxydammarenone (20 hydroxydammar 24 en 3 one) 1, oleanolic acid (3 hydroxyolean 12 en 28 oic acid) 2, oleanonic acid (3 oxoolean 12 en 28 oic acid) 3, 18(3 glycyrrhetinic acid ((3(3,18(3,20(3) 3 hydroxy 11 oxoolean 12 en 29 oic acid) 4, uvaol (urs 12 en 3,28 diol) 5, ursolic acid (3 hydroxyurs 12 en 28 oic acid) 6, and ursonic acid (3 oxours 12 en 28 oic acid) 7...

Cholenic acid-3P-ol] (triterpene) Human animal origin cf. oleanolic acid PKA (8)... 

Aleuritolic acid (triterpene) Fulvoplumierin (iridoid monoterpene) Oleanolic acid (oleanane triterpene)... 

Oleanolic acid (triterpene) Lonicera nigra (Caprifoliaceae), Beta vulgaris (Chenopodiaceae), Syzygium aromaticum (Myrtaceae) COX-1, COX-2 [AI]... 

Triterpenic Acids. The following pentacyclic mono- and dihydroxy triterpenic acids are present in virgin olive oil (35, 43, 44) 3p-hydroxy-17-carboxy-5-12-olea-nene (oleanolic acid) 3 3,2a-dihydroxy-17-carboxy-5-12-oleanene (maslinic acid) 3p-hydroxy-17-carboxy-8-12-ursene (ursolic acid) 2a,3p-dihydroxy-17-carboxy-5-12-ursene (2a-hydroxyursolic acid) and deoxyursolic acid (structure not fully elucidated). 

Triterpenols and sterols are present as free or esterified with fatty acids (oleic acid and linoleic acid as the most relevant). Total content of triterpens is between 100-300 mg/100 g of oil. 24-Methylen-cycloartanol and cycloartenol are dominant. Erythrodiol, uvaol and triterpenic acids (ursolic, oleanolic acids etc) have been described in the imsaponifiable fraction of olive oil. The terpenoid fraction is complex and many constituents are still imdefined. 

Less polar compounds such as polyhydroxylated triterpenes and their esters and flavonoid aglycones are usiuilly separated from CHCI3 extracts by preliminary fractionation on silica gel column with CHCI3 -MeOH gradients followed by RP-HPLC on a Cig column with MeOH or Me0H-H20 mixtures as the eluent. A typical example is the separation of ursolic acid derivatives from oleanolic acid derivatives and their esters from E.Japonica (23). 

Oleanolic acid (oleanene triterpene) Lujfa cylindrica (Cucurbitaceae), Rosmarinus officinalis (Lamiaceae) HIV-I protease (8 pM 22 pM) (C3-convertase, Elastase) [46]... 

Continued efforts are still ongoing to find economical ways to isolate and purify these compounds [20], Furthermore, rme sees in olive pomace a source for squalene (16) [32], tocopherols (17) [33], D-marmitol (18) [34], triterpenes oleanolic (19) and maslinic (20) acids [35], pectic polysaccharides [13], hemicelluloses [36], and oligosaccharides [34]. 

Preliminary structure-activity relationship studies on triterpene saponins have shown the best activity against HSV-1, -2, adenovirus (AD-2), polyovirus (PV-2) and VSV for saponins having as aglycones ursolic acid, glycyrrhetinic acid, hederagenin and oleanolic acid [152],... 

Compounds isolated from Celastraceae had showed cytotoxic activity [3,4]. This property has been related mainly to nor-triterpene quinonemethides, but cytotoxic triterpenes had also been reported [96]. As an example, both, tumor initiation and promotion are inhibited by two triterpenes commonly isolated from the familiy, ursolic and oleanolic acids [16]. 

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