178600-68-5Relevant academic research and scientific papers
New semi-synthetic analogs of oleuropein show improved anticancer activity in?vitro and in?vivo
Samara, Pinelopi,Christoforidou, Nikoleta,Lemus, Christelle,Argyropoulou, Aikaterini,Ioannou, Kyriaki,Vougogiannopoulou, Konstantina,Aligiannis, Nektarios,Paronis, Efthimios,Gaboriaud-Kolar, Nicolas,Tsitsilonis, Ourania,Skaltsounis, Alexios-Leandros
, p. 11 - 29 (2017)
Oleuropein is a glucosylated seco-iridoid present in olive fruits and leaves. Due to its broad spectrum of biological activities, including anticancer properties, oleuropein has attracted scientific attention for the past 20 years. The promising antiproliferative activity of an olive leaf extract enriched in oleuropein against a series of human cancer cell lines, prompted us to proceed with the semi-synthesis of 51 analogs of oleuropein. Following their initial screening against the estrogen receptor negative breast cancer cell line SKBR3, 7 analogs were shown to display significant cytotoxicity and were further tested against 6 additional solid tumor-derived and leukemic cell lines. The analog with the most promising antitumor activity (24) was selected for more detailed studies. 24 was non-toxic to peripheral blood mononuclear cells derived from healthy blood donors when tested at concentrations close to its half maximal inhibitory concentration. In vivo administration of 24 in melanoma-bearing mice resulted in reducing tumor size in a dose-dependent manner and in inducing anti-melanoma-reactive immune responses. Our results suggest that analog 24, emerging from the initial structure of oleuropein, represents a promising lead structure for further optimization.
Biomimetic Synthesis of Oleocanthal, Oleacein, and Their Analogues Starting from Oleuropein, A Major Compound of Olive Leaves
Sarikaki, Georgia,Christoforidou, Nikoleta,Gaboriaud-Kolar, Nicolas,Smith, Amos B.,Kostakis, Ioannis K.,Skaltsounis, Alexios-Leandros
, p. 1735 - 1739 (2020)
Oleocanthal and oleacein are known for a wide range of beneficial activities in human health and the prevention of diseases. The inability to isolate significant and pure amounts of these natural compounds and their demanding synthesis lead to the development of an efficient, five-step, three-pot procedure. The synthesis is performed by a convenient biomimetic approach, starting from oleuropein, an abundant raw material in olive leaves, through the mixed anhydride of oleoside. The method is stereocontrolled and provides an efficient approach to the synthesis of various oleocanthal analogues; thus, a small library of four compounds was prepared with 35-45% overall yield.
Oleuropein site selective hydrolysis by technomimetic nuclear magnetic resonance experiments
Capozzi,Piperno,Uccella
, p. 1623 - 1629 (2000)
Technomimetic NMR experiments were performed in accordance with the lye treatment adopted during table olive industrial procedures for the debittering process causing oleuropein degradation. The site selective hydrolysis of the two ester groups, character
PROCESS FOR THE PRODUCTION OF OLEOCANTHAL, OLEACEIN AND THEIR ANALOGUES
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Page/Page column 12, (2021/06/26)
A process for the production of a compound according to Formula (I), such as oleocanthal or oleacein, starting from oleuropein. The process provides the dialdehyde core of oleocanthal, oleacein and their analogues having the required stereochemistry. Furthermore, the process can be used for the production of a large number of structurally diverse products by varying the structure of the alcohol moiety in the esterification step.
Ilicifoliosides A and B, bis-secoiridoid glycosides from Osmanthus Ilicifolius
Sakamoto, Shigeaki,Machida, Koichi,Kikuchi, Masao
, p. 937 - 941 (2008/09/19)
Two new bis-secoiridoid glycosides, named ilicifoliosides A and B, were isolated from the leaves of Osmanthus ilicifolius. Their structures have been determined by 1D and 2D NMR analysis.
Main antimicrobial compounds in table olives
Medina, Eduardo,Brenes, Manuel,Romero, Concepcion,Garcia, Aranzazu,De Castro, Antonio
body text, p. 9817 - 9823 (2010/03/31)
The inhibitors involved in the lactic acid fermentation of table olives were investigated in aseptic olive brines of the Manzanilla and Gordal varieties. Phenolic and oleosidic compounds in these brines were identified by high-performance liquid chromatography with ultraviolet and electrospray ionization mass spectrometry detection, and several substances were also characterized by nuclear magnetic resonance. Among these compounds, the dialdehydic form of decarboxymethyl elenolic acid linked to hydroxytyrosol showed the strongest antilactic acid bacteria activity, and its presence in brines could explain the growth inhibition of these microorganisms during olive fermentation. However, it was found that the dialdehydic form of decarboxymethyl elenolic acid, identified for the first time in table olives, and an isomer of oleoside 11-methyl ester were also effective against Lactobacillus pentosus and can, therefore, contribute to the antimicrobial activity of olive brines. It must also be stressed that the three new inhibitors discovered in table olive brines exerted a more potent antibacterial activity than the well-studied oleuropein and hydroxytyrosol.
Three secoiridoid glucosides from Jasminum nudiflorum
Tanahashi, Takao,Takenaka, Yukiko,Nagakura, Naotaka,Nishi, Toyoyuki
, p. 1311 - 1315 (2007/10/03)
Phytochemical study of the leaves and stems of Jasminum nudiflorum has led to the isolation of three secoiridoid glucosides, jasnudiflosides A-C (1- 3). The structures of these compounds were elucidated on the basis of chemical and spectroscopic evidence.
SAMBACOSIDES A, E AND F, NOVEL TETRAMERIC IRIDOID GLUCOSIDES FROM JASMINUM SAMBAC
Tanahashi, Takao,Nagakura, Naotaka,Inoue, Kenichiro,Inouye, Hiroyuki
, p. 1793 - 1796 (2007/10/02)
Structures of three tetrameric iridoid glucosides, sambacosides A, E and F isolated from the leaves of Jasminum sambac (L.) Ait. were elucidated as 2, 3 and 4 by chemical and spectometric means.They represent the first tetrameric iridoid glucosides.
