Phenolic components of<i>Olea Europaea</i>– isolation of tyrosol derivatives

Bianco, Armandodoriano; Melchioni, Cristiana; Ramunno, Alessia; Romeo, Giovanni; Uccella, Nicola

doi:10.1080/1478641031000111570

Cited by 33 publications

(18 citation statements)

References 2 publications

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“…This cultivar is very common in the MAC eating pattern and is commercially essential for extra virgin olive oil and table olives produced in the region. This cultivar is an important source of olive BPs, which encompasses several BPsecos and has a bitter, astringent flavor with pungency [ 36 , 37 , 38 , 39 ]. The level of bitterness in olive oil from various cultivars is a result of BPseco downstream products [ 40 , 41 , 42 , 43 ].…”

Section: Resultsmentioning

confidence: 99%

Probing Downstream Olive Biophenol Secoiridoids

Sivakumar

Uccella

Gentile

2018

IJMS

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Numerous bioactive biophenol secoiridoids (BPsecos) are found in the fruit, leaves, and oil of olives. These BPsecos play important roles in both the taste of food and human health. The main BPseco bioactive from green olive fruits, leaves, and table olives is oleuropein, while olive oil is rich in oleuropein downstream pathway molecules. The aim of this study was to probe olive BPseco downstream molecular pathways that are alike in biological and olive processing systems at different pHs and reaction times. The downstream molecular pathway were analyzed by high performance liquid chromatography coupled with electrospray ionization mass spectrometry (HPLC-ESI/MS) and typed neglected of different overlap (TNDO) computational methods. Our study showed oleuropein highest occupied molecular orbital (HOMO) and HOMO-1 triggered the free radical processes, while HOMO-2 and lowest unoccupied molecular orbital (LUMO) were polar reactions of glucoside and ester groups. Olive BPsecos were found to be stable under acid and base catalylic experiments. Oleuropein aglycone opened to diales and rearranged to hydroxytyrosil-elenolate under strong reaction conditions. The results suggest that competition among olive BPseco HOMOs could induce glucoside hydrolysis during olive milling due to native olive β-glucosidases. The underlined olive BPsecos downstream molecular mechanism herein could provide new insights into the olive milling process to improve BPseco bioactives in olive oil and table olives, which would enhance both the functional food and the nutraceuticals that are produced from olives.

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Section: Resultsmentioning

confidence: 99%

Probing Downstream Olive Biophenol Secoiridoids

Sivakumar

Uccella

Gentile

2018

IJMS

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“…The first method was employed in our previous work [24]. In particular, the extraction procedure from olive oil and by-products was carried out according to Bianco and coworkers, using 1/1 MeOH-acetone ( v / v ) solution containing 0.5% sodium metabisulfite [35]. Method 2.…”

Section: Methodsmentioning

confidence: 99%

Hydroxytyrosyl Oleate: Improved Extraction Procedure from Olive Oil and By-Products, and In Vitro Antioxidant and Skin Regenerative Properties

et al. 2019

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Recently, we identified hydroxytyrosyl oleate (HtyOle) in the by-products of olive oil, pomace and olive mill waste water (OMWW). Herein, we report that HtyOle is more accurately quantified by extracting the phenolic fraction from both matrices by using aqueous methanol (80%). By applying this method, HtyOle was also detected in extra virgin olive oil (EVOO). Since olive oil is used in the preparation of many cosmetic formulations, we explored the antioxidant capacity of HtyOle in human keratinocytes. Formation of reactive oxygen species (ROS) and malondialdehyde (MDA), as well as activity of Glutathione-S-transferase (GST) and superoxide dismutase (SOD) were decreased by HtyOle. In addition to that, microRNAs (miRs) involved in both redox status balance and skin regeneration potential were also tested. The following miRs, hsa-miR-21 and hsa-miR-29a, were increased while has-miR-34a was not affected by HtyOle.

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“…Some of hydroxytyrosol derivatives like hydroxytyrosol rhamnoside ( 85 ) [ 56 ], hydroxytyrosol glucoside ( 86 ) [ 45 , 57 ], and methyl malate- β -hydroxytyrosol ester ( 98 ) [ 58 ] were isolated from olive fruit for the first time. Isolation of new tyrosol derivatives, tyrosol glucoside salidroside ( 89 ), and 1-oleyltyrosol ( 99 ) [ 59 , 60 ], along with cornoside ( 37 ) [ 20 , 52 ], 2(3,4-dihydroxy-phenyl)ethanol ( 90 ) [ 61 ], halleridone ( 38 ) [ 52 ], and hydroxytyrosol-elenolate ( 14 ) [ 54 , 61 – 63 ] has also been reported from the fruits of O. europaea . An important and major phenolic compound present in natural table olives is 3,4-dihydroxyphenylglycol (DHPG) ( 138 ) which is reported from natural as well as different cultivated olive samples [ 64 , 65 ].…”

Section: Phytochemistrymentioning

confidence: 99%

Traditional Uses, Phytochemistry, and Pharmacology ofOlea europaea(Olive)

Hashmı

Khan

Hanif

et al. 2015

Evidence-Based Complementary and Alternative Medicine

195

161

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Aim of the Review. To grasp the fragmented information available on the botany, traditional uses, phytochemistry, pharmacology, and toxicology of Olea europaea to explore its therapeutic potential and future research opportunities. Material and Methods. All the available information on O. europaea was collected via electronic search (using Pubmed, Scirus, Google Scholar, and Web of Science) and a library search. Results. Ethnomedical uses of O. europaea are recorded throughout the world where it has been used to treat various ailments. Phytochemical research had led to the isolation of flavonoids, secoiridoids, iridoids, flavanones, biophenols, triterpenes, benzoic acid derivatives, isochromans, and other classes of secondary metabolites from O. europaea. The plant materials and isolated components have shown a wide spectrum of in vitro and in vivo pharmacological activities like antidiabetic, anticonvulsant, antioxidant, anti-inflammatory, immunomodulatory, analgesic, antimicrobial, antiviral, antihypertensive, anticancer, antihyperglycemic, antinociceptive, gastroprotective, and wound healing activities. Conclusions. O. europaea emerged as a good source of traditional medicine for the treatment of various ailments. The outcomes of phytochemical and pharmacological studies reported in this review will further expand its existing therapeutic potential and provide a convincing support to its future clinical use in modern medicine.

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Phenolic components ofOlea Europaea– isolation of tyrosol derivatives

Abstract: A new tyrosol derivative, the oleic ester of tyrosol, was isolated from fruits of Olea europaea, Cassanese cultivar. Salidroside, the known glucosyl derivative of thyrosol, was isolated from the Carolea cultivar.

Cited by 33 publications

References 2 publications

Probing Downstream Olive Biophenol Secoiridoids

Probing Downstream Olive Biophenol Secoiridoids

Hydroxytyrosyl Oleate: Improved Extraction Procedure from Olive Oil and By-Products, and In Vitro Antioxidant and Skin Regenerative Properties

Traditional Uses, Phytochemistry, and Pharmacology ofOlea europaea(Olive)

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