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OLEUROPEIN and OLEUROPEIN AGLYCONE 1469 of These Compounds Might Help to Confer Those Health 4 468/0LEOCANTHAL PDR FOR NUTRITIONAL SUPPLEMENTS INDICATIONS AND USAGE premium extra-virgin olive oil contains about nine milli- Olecocanthal, an olive polyphenol, has reported antioxida- grams of oleocanthal. The potency of oleocanthal and tive and antiinflammatory activity. One report stirred wide ibuprofen is approximately the same. Therefore, nine milli- interest in the substance by claiming it has ibuprofen-like grams of oleocanthal is approximately equal to nine milli- activity. In common with what has been claimed for other grams of ibuprofen, which is about 10% percent of a low olive polyphenols (see Hydroxytyrosol and Oleuropein), it dose (l00 milligrams) of ibuprofen. may have some cardioprotective and anticancer activity, as Dietary supplements of oleocanthal are currently well, although clinical evidence for this is lacking. unavailable. RESEARCH SUMMARY LITERATURE A brief communication in the journal Nature excited interest Andrewes p, Busch JL, de Joode T, et al. Sensory properties of in oleocanthal when researchers reported that this substance, virgin olive oil polyphenols: identification of deacetoxy- derived from newly pressed extra-virgin olive oil, has some ligstroside aglycon as a key contributor to pungency. Agric characteristics in common with the anti-inflammatory drug Food Chem. 2003;51(5):1415-1420. ibuprofen. They noted that both induce very similar stinging Beauchamp GK, Keast RS, Morel D, et al. Phytochemistry: sensations in the throat and thereafter determined that the ibuprofen-like activity in extra-virgin olive oil. Nature. two substances have structural and pharmacological similari- 2005;437(7055):45-46. ties. They found that oleocanthal, like ibuprofen, is an Fini L, Hotchkiss E, Fogliano V, et al. Chemopreventive inhibitor of the COX-I and COX-2 enzymes in a dose- properties of pinoresinol-rich olive oil involve a selective dependent manner. Thus they hypothesized that, through activation of the ATM-p53 cascade in colon cancer cell lines. consistent long-term consumption of extra-virgin olive oil, Carcinogenesis. 2oo8;29( I): 139-46. some ibuprofen-like relief from inflammation and pain might Fogliano V, Sacchi R. Oleocanthal in olive oil: between myth be realized in some individuals. Others, however, have and reality. Mol Nutr Food Res. 2006;50(1):5-6. questioned whether plasma levels of the polyphenol could Impellizzeri J, Un J. A simple high-performance liquid thus ever be high enough to have a meaningful effect. chromatography method for the determination of throat-burning Research is needed to see whether supplements of this oleocanthal with probated antiinflammatory activity in extra substance could safely and effectively be used in the same virgin olive oils. J Agric Food Chem. 2006;54(9):3204-3208. way that ibuprofen is used. If so, it might have application in Joshi K, Hankey. A, Patwardhan B. Traditional phytochemistry: a number of situations since there are data suggesting that identification of drug by 'taste'. Evid Based Complement ibuprofen, apart from providing pain relief, may, when used Alternat Med. 2007;4(2): 145-148. long-term, have some inhibiting effect on various inflamma- tory processes, including Alzheimer's disease. Smith AB 3rd, Sperry 18, Han Q. Syntheses of (-)-oleocanthal, a natural NSAID found in extra virgin olive oil, the (-)- CONTRA INDICATIONS, PRECAUTIONS, ADVERSE REACTIONS deacetoxy-oleuropein aglycone, and related analogues. J Org CONTRA INDICA TIONS Chem. 2007;72(18):6891-6900. Oleocanthal is contraindicated in those hypersensitive to any Smith AB 3rd, Han Q, Breslin PA, et al. Synthesis and component of an oleocanthal-containing product. Hypersen- assignment of absolute configuration of (-)-oleocanthal: a potent, sitivity to oleocanthal is probably very rare. naturally occurring non-steroidal anti-inflammatory and anti- oxidant agent derived from extra virgin olive oils. Org Lett. PRECAUTIONS 2005;7(22):5075-5078. Those who wish to use oleocanthal for health reasons should first discuss this with his or her physician. ADVERSE REACTIONS No reports. Oleuropein and Oleuropein INTERACTIONS Aglycone No reports. DESCRIPTION Olive oil is the principal fat component in the Mediterranean OVERDOSAGE diet, and the consumption of olive oil by those who live in There are no reports of overdosage. the Mediterranean basin has been associated with a lower DOSAGE AND ADMINISTRATION incidence of coronary heart disease (CHD), some cancers, The concentration of oleocanthal in extra-virgin olive oil is including prostate, breast and colorectal cancer, and other variable. Premium extra-virgin olive oil contains up to 200 chronic degenerative diseases. A large number of phenolic micrograms of oleocanthal per milliliter. Fifty grams of compounds are found in olive oil, and it is thought that some SUPPLEMENT MONOGRAPHS OLEUROPEIN AND OLEUROPEIN AGLYCONE 1469 of these compounds might help to confer those health 4. OJeuropein is represented by the following chemical benefits. structure. The phenolic compounds found in olive oil can be broken down into simple phenols (eg, tyrosol, hydroxytyrosol and elenolic acid), lignans (eg, pinoresinol and acetoxypinoresi- no!) and secoiridoids (eg, oleuropein aglycone, deacetoxy oleuropein aglycone, and ligstroside aglycone). Oleuropein aglycone is the most abundant polyphenol in olive oil and is responsible for the characteristic bitter, pungent taste of the oil. Oleuropein (oleuropein glycoside) is found in olive fruit, in the leaves and bark of the olive tree (Olea europaea L.), and in olive mill wastewater. Oleuropein Oleuropein is also found in the fruits and leaves of the Japanese privet tree (Ligustrum japonicum) and the Chinese privet tree Oleuropein is moderately soluble In water; oleuropein (Ligustrum lucidum). Oleuropein, known as the bitter aglycone is much less so. principle of the olive tree, is present in high amounts in the leaves. It is a secondary metabolite of the olive tree and ACTIONS AND PHARMACOLOGY ACTIONS confers resistance to disease and to insect infestation. Olive Oleuropein has antioxidant actiVity. It may also have leaf extracts, mainly oleuropein, were used by the ancient anticancer, anti-inflammatory, antimicrobial, antithrombotic, Egyptians to mummify their pharaohs and, in the 1800s, by cardioprotective and rejuvenating/anti aging activities. the British to treat tropical diseases, including malaria. MECHANISM OF ACTION The types of phenols in extra-virgin olive oil are different Anticancer activity: Oleuropein was shown to inh'ibit the from those of the olive fruit. The olives mainly contain the proliferation and migration of advanced-grade human tumor polar glycosides oleuropein and ligstroside. Oleuropein is the cell lines dose-dependently. The tumor cell lines included ester of elenoic acid with 3,4/-dihydroxyphenylethanol LN-18, poorly differentiated glioblastoma, TF-la, erythro- (hydroxytyrosol), and ligstroside is the ester of elenolic acid leukemia, 786-0, renal cell adenocarcinoma, T-47D, infiltrat- with 4-hydroxyphenylethanol (tyrosol). Oleuropein and lig- ing ductal carcinoma of the breast-pleural effusion, MCF-7, stroside are the parent compounds of the less polar oleuro- mammary gland adenocarcinoma, pleural effusion, RPMI- pein aglycone and ligstroside aglycone. Oleuropein aglycone 7952, malignant melanoma of the skin, node metastasis, and and ligstroside aglycone are formed during ripening by removal of the glucose moiety from the oleuropein- and LoV0, colorectal adenocarcinoma and suprascapular region metastasis. ligstroside-glycosides via the enzyme, beta-glucosidase. Those aglycones and their various derivatives are the most Oleuropein was shown to induce the production of irrever- abundant phenols in olive oil. Hydroxytyrosol is mainly sibly rounded cells, preventing their replication, motility and formed from the hydrolysis of the secoiridoid oleuropein invasiveness. No viable cells could be recovered from those aglycone (see Hydroxytyrosol). tumors. Oleuropein directly disrupted actin filaments in cells and in a cell-free system. Only very high doses of the olive The name "oleuropein" refers to the glycoside form and i~ polyphenol caused growth inhibition in normal fibroblasts. sometimes called oleuropein glycoside; the aglycone form is always called, or should always be called, oleuropein In order to see if the glucose moiety in oleuropein affected aglycone. These names are not always used correctly. its biological activity, it was removed with beta-glucosidase to produce oleuropein aglycone. Beta-glucosidase treated Oleuropein is chemically described as methyl (4S,5E,6S)-4- oleuropein was less effective in inhibiting cell proliferation [2-[2-(3,4-dihydroxypheny!)ethoxy]- 2-oxoethyl]-5- ethyli- than the nontreated phenol. Possibly, the glucose transporters dene-6- [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6- (hydroxymeth- (GLUTs) were necessary to facilitate the diffusion of yl)oxan-2-yl]oxy-4H-pyran-3-carboxylate. It is also known oleuropein into the cells, and they didn't work as well for as [2S-(2alpha,3E,4beta)]- 3-ethylidene- 2-(beta- D-glucopyra- oleuropein aglycone. The mechanism of this interesting nosyloxy)- 3,4-dihydro- 5-(methoxycarbony 1)-2H-pyran-4-a- anticancer activity of oleuropein is unclear. Continued cetic acid 2-(3,4-dihydroxyphenyl)ethyl ester. research in this promising area is needed and warranted. Oleuropein's empirical formula is C2sH32013, its molecular Human epidermal growth factor receptor 2 (HER2) is an weight is 540.51 and its CAS Registry Number is 32619-42-
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