Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Patent
1998-03-20
2000-03-14
Geist, Gary
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
C07C 6112
Patent
active
060374926
DESCRIPTION:
BRIEF SUMMARY
PRIOR ART
The cultivation of olive trees is very important in temperate countries almost throughout the world. The trees are primarily used for olive oil, and Spain is currently a producer of over a million metric tons. Classic olive milling and oil production processes consist of the so-called both continuous and discontinuous "three-phase" processes. In addition to oil, these processes yield such by-products as oil-foot, an aqueous fraction of olives with or without the addition of water, and the various types of pressed olive refuse, which is generally extracted for an additional recovery of oil. In addition to three-phase processes, a so-called "two-phase" process is used which, in addition to oil, yields a mass containing the pulp remains and usually, although not always, the olive stone, mixed with the plant water, resulting in a by-product which is beginning to be known as the "oil-foot refuse".
Oleanolic (3-betahydroxy-28-carboxyoleanene) acid is a triterpenic acid ubiquitously distributed within the plant kingdom. The United States Department of Agriculture phytochemical database (Internet address http://probe.nalusda.gov: 8300/cgi-bin/browse/phytochemdb) has indeed noted its presence in almost a hundred plants, inter alia the Olea europaea, and moreover a number of proven biological activities (abortifacient, anticariogenic, antifertility, antihepatotoxic, anti-inflammatory, antisarcomic, cancer-preventive, cardiotonic, diuretic, hepatoprotective and uterotonic). Publications are continuously being made regarding the potential biological activity of this acid and its glycosides. It has indeed been studied for activity as an inhibitor of the proliferation of leukaemia cells (Essady, D., Najid, A., Simo, A., Denizot, Y., Chulia, A. J., and Delage, C.; Mediators of Inflammation (1994) 3, 181-184), a hypoglucemiant (Yoshikawa, M., Matsuda, H., Harada, E., Mukarami, T., Wariishi, N., Marakami, N. and Yamahara, J., Chemical & Pharmaceutical Bulletin (1994) 42, 1354-1356) an antitumoral (Ohigashi, H., Mukarami, A. and Koshinizu, K. ACS Symposium Series (1994) 547, 251-261), a producer of antagonist effects in anaphylactic shock (Zhang, L. R. and Ma, T. X.; Acta Pharmacologica Sinica (1995) 16, 527-530), a hepatoprotector (Liu, Y. P., Parkinson, A. and Klaasen, C. D.; Journal of Pharmacology and Experimental Therapeutics (1995) 275, 768-774; Connolly, J. D. and Hill, R. A. Natural Product Reports 12, 609-638 (1995), and an anti-inflammatory (Recio, M. D., Giner, R. M., Manez, S. And Rios, J. L., Planta Medica (1995) 61, 182-185. A specific review of the pharmacological activity of oleanolic acid has been published (Liu. J. Journal of Ethnopharmacology (1995) 49, 57-68). Maslinic (2-alpha,3-betadihidroxy-28-carboxyoleanene) acid, also known as crataegolic acid, is far less widespread in nature, and has been found in a dozen plants (Internet Address http://probe.nalusda.ov: 8300/cgi-bin/browse/phytochemdb). It is known (Internet Address http://probe.nalusda.gov:8300/cgi-bin/browse/phytochemdb) to have antihistaminic and anti-inflammatory activity although it has not been extensively studied because of its scarcity. The isolation of oleanolic and maslinic acids from waxes on the surface of the fruit of the Olea europaea has been described (Bianchi, G., Pozzi, N. And Vlahov, G. Phytochemistry (1994) 37, 205-207) by means the methanol extraction from olives previously washed with chloroform. The separation of aids of this type has been described by means of high-speed counter-current chromatography (HSCCC) (Du, Q. Z., Xiong, X. P. and Ito, Y.; Journal of Liquid Chromatography (1995) 18, 1997-2004). ##STR1##
DESCRIPTION OF THE INVENTION
Oil cakes, obtained by classic pressing, "three-phase" processing pressed olive refuse, oil-foot refuse obtained from the so-called "two-phase" system and broadly speaking any residue from the processing of whole olives or parts thereof containing their original skin residues, with or without subsequent processing to recover the oil they contain, with or without preliminary
REFERENCES:
Database CAPLUS on STN, Acc. No. 1986:423292, Lanzani et al., `Olive marc: transformation and recovery technology of by-products for practical appliacations. Note I.` Riv. Ital. Sostanze Grasse (1985), 62(11), pp. 597-604, abstract.
Davis Brian J.
Geist Gary
Universidad de Granada
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