Bioactive Compounds with Added Value Prepared from Terpenes Contained in Solid Wastes from the Olive Oil Industry

Abstract

Starting from solid wastes from two-phase olive-oil extraction, the pentacyclic triterpenes oleanolic acid and maslinic acid were isolated. These natural compounds were transformed into methyl olean-12-en-28-oate (5), which then was transformed into several seco-C-ring triterpene compounds by chemical and photolytic modifications. The triene seco-products were fragmented through several oxidative procedures to produce, simultaneously, cis- and trans-decalin derivatives, both potential synthons for bioactive compounds. The chemical behavior of the isolated fragments was investigated, and a suitable approach to several low-molecular-weight terpenes was performed. These are interesting processes for the value-addition to solid waste from the olive-oil industry.

Towards an Efficient Protocol for the Determination of Triterpenic Acids in Olive Fruit: A Comparative Study of Drying and Extraction Methods

“…The residue was dissolved into 10 mL of methanol. Soxhlet extraction has been used to extract triterpenic acids from an array of plant tissues (Kontogianni et al ., ; Parra et al ., ; Tarvainen et al ., ).…”

Olive Pomace Extract Contains Low Molecular Weight Peptides and Possesses ACE Inhibitory Activity

“…To contribute to environmental sustainability, a number of strategies for the revalorization of olive oil waste have been proposed based on the extraction of compounds with added value that can be used for the food and pharmaceutical industries [8,9]. Such is the case for the recovery of antioxidant polyphenols [10], terpenic acids [11], polar lipids [12], protein hydrolysates [13,14], pigments (chlorophylls and carotenoids), tocopherols, phytosterols, squalene, and aromatic compounds [8]. Examples include the use of phenolic extracts of olive pomace to enrich vegetable oils, fish burgers, fermented milk, and in the coating of edible fruits to take advantage of its antioxidant and antimicrobial effects.…”

Effect of the Solvent and the Sample Preparation on the Determination of Triterpene Compounds in Two-Phase Olive-Mill-Waste Samples

“…Approximately six-million tons of TPOMW are produced annually in Spain, causing serious management problems due to its phytotoxicity and its semisolid texture. , Different technologies have been proposed for the TPOMW treatment. However, this byproduct is a promising source of potentially useful compounds such as phenolic compounds, − oligosaccharides, , mannitol, ,, and triterpene compounds. , This natural starting material is a significant source of triterpenes that can be used to produce chiral intermediates and may have many applications such as flavorings, fragrances, pharmaceuticals, or biocontrol agents . Among them, the main acids are oleanolic (3β-hydroxyolean-12-en-28-oic acid, 1 ), maslinic (2α,3β-dihydroxyolean-12-en-28-oic acid, 2 ), and ursolic (3β-hydroxyursan-12-en-28-oic acid, 3 ); meanwhile, the main alcohols are erythrodiol (olean-12-ene-3β,28-diol, 4 ) and uvaol (urs-12-ene-3β,28-diol, 5 ) (Figure ).…”

“…11,12 This natural starting material is a significant source of triterpenes that can be used to produce chiral intermediates and may have many applications such as flavorings, fragrances, pharmaceuticals, or biocontrol agents. 13 Among them, the main acids are oleanolic (3β-hydroxyolean-12-en-28-oic acid, 1), maslinic (2α,3β-dihydroxyolean-12-en-28-oic acid, 2), and ursolic (3βhydroxyursan-12-en-28-oic acid, 3); meanwhile, the main alcohols are erythrodiol (olean-12-ene-3β,28-diol, 4) and uvaol (urs-12-ene-3β,28-diol, 5) (Figure 1). The studies published on these pentacyclic triterpenes have demonstrated that they display a wide variety of biological effects such as antiinflammatory, anti-HIV, analgesic, antimicrobial, hepatoprotective, and virostatic properties.…”