Chemical and biological modification of cynaropicrin and grosheimin: a structure–bitterness relationship study

Cravotto, Giancarlo; Nano, Gian Mario; Binello, Arianna; Spagliardi, Paola; Seu, G.

doi:10.1002/jsfa.2180

Cited by 34 publications

(18 citation statements)

References 24 publications

(25 reference statements)

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“…(1) The cynaropicrin is one of the main active constituents of artichoke; the therapeutic effects of the latter have been observed in several clinical trials (Giacosa et al, 2015) and it has recently attracted attention because of its well-proven safety at concentrations currently employed in alcoholic beverages (Cravotto et al, 2005). Another clinical study recommended artichoke extract for treating hyperlipoproteinemia and, thus, prevention of atherosclerosis and coronary heart disease and showed that there were no drug-related adverse events indicating an excellent tolerability of artichoke extract (Englisch et al, 2000).…”

Section: Discussionmentioning

confidence: 99%

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Cynaropicrin: A Comprehensive Research Review and Therapeutic Potential As an Anti-Hepatitis C Virus Agent

2016

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The different pharmacologic properties of plants-containing cynaropicrin, especially artichokes, have been known for many centuries. More recently, cynaropicrin exhibited a potential activity against all genotypes of hepatitis C virus (HCV). Cynaropicrin has also shown a wide range of other pharmacologic properties such as anti-hyperlipidemic, anti-trypanosomal, anti-malarial, antifeedant, antispasmodic, anti-photoaging, and anti-tumor action, as well as activation of bitter sensory receptors, and anti-inflammatory properties (e.g., associated with the suppression of the key pro-inflammatory NF-κB pathway). These pharmacological effects are very supportive factors to its outstanding activity against HCV. Structurally, cynaropicrin might be considered as a potential drug candidate, since it has no violations for the rule of five and its water-solubility could allow formulation as therapeutic injections. Moreover, cynaropicrin is a small molecule that can be easily synthesized and as the major constituent of the edible plant artichoke, which has a history of safe dietary use. In summary, cynaropicrin is a promising bioactive natural product that, with minor hit-to-lead optimization, might be developed as a drug for HCV.

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Section: Discussionmentioning

confidence: 99%

“…Cynaropicrin contributes to approximately 80% of the characteristic bitter taste of artichoke, which is associated with the activation of bitter sensory receptors (Cravotto et al, 2005; Eljounaidi et al, 2015). Cynaropicrin can be isolated in gram-scale by employing countercurrent chromatography (Adekenova et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

Cynaropicrin: A Comprehensive Research Review and Therapeutic Potential As an Anti-Hepatitis C Virus Agent

2016

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“…For example, several studies proposed a correlation between hydrophobicity and bitterness (44,45). Additionally, a recent study showed that bitterness of the soy peptides is predominantly associated with molecular mass (47).…”

Section: Examplesmentioning

confidence: 99%

BitterDB: a database of bitter compounds

Wiener

Shudler

Levit

et al. 2011

Nucleic Acids Research

217

199

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Basic taste qualities like sour, salty, sweet, bitter and umami serve specific functions in identifying food components found in the diet of humans and animals, and are recognized by proteins in the oral cavity. Recognition of bitter taste and aversion to it are thought to protect the organism against the ingestion of poisonous food compounds, which are often bitter. Interestingly, bitter taste receptors are expressed not only in the mouth but also in extraoral tissues, such as the gastrointestinal tract, indicating that they may play a role in digestive and metabolic processes. BitterDB database, available at http://bitterdb.agri.huji.ac.il/bitterdb/, includes over 550 compounds that were reported to taste bitter to humans. The compounds can be searched by name, chemical structure, similarity to other bitter compounds, association with a particular human bitter taste receptor, and so on. The database also contains information on mutations in bitter taste receptors that were shown to influence receptor activation by bitter compounds. The aim of BitterDB is to facilitate studying the chemical features associated with bitterness. These studies may contribute to predicting bitterness of unknown compounds, predicting ligands for bitter receptors from different species and rational design of bitterness modulators.

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“…Grosheimin (1) is a sesquiterpene lactone of guaiane type has high antitumour, antiviral, antiphlogistic, and bactericidal activity [3][4][5]. The "Hartinol" is a pharmaceutical water-soluble form of Grosheimin, is obtained by chemical modification.…”

Section: Introductionmentioning

confidence: 99%

“…Cynaropicrin (2) is a sesquiterpene lactone of guaiane type possessing high antitumor, antibacterial, anti-protist and anti-trichomonas activities [5,7] It is active component of the "Sausalin" antiparasitic pharmaceutical effect. (1)…”

Section: Introductionmentioning

confidence: 99%

Reference Standards Based on the Grosheimin and Cynaropicrin

Adekenova¹

2016

Eur Chem Tech J

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The aim of this work is the development of effective method for producing the reference standards of Grosheimin and Cynaropicrin for quality control of domestic herbal medicines, as well as project development concerning normative documents on reference standards of Grosheimin and Cynaropicrin, an introduction of reference standards to the Pharmacopoeia of Kazakhstan. This article discusses the method of allocation and purification of reference standards of Grosheimin and Cynaropicrin which are sesquiterpene lactones of guaiane type were obtained from the ethyl acetate extract of Chartolepis intermedia Boiss., using centrifugal distribution chromatography and high performance liquid chromatography, allows to obtain the qualitative target products. The effectiveness of developed technology has reduced the labor contribution in 2.0 times and as a consequence the prime cost of end products come down 3 times. Using of Grosheimin and Cynaropicrin as own reference standard of the Republic of Kazakhstan for monitoring of staged quality control of pharmaceutical production: access control, intermediate control and output control, it means the finished dosage form. There are some chromatographic analysis data of the samples. Such methods as IR and NMR-spectophotometries were applied for determination of molecular structure. Pharmacopoeial methods were used to determine the color, taste, odor and solubility of reference standards in various solvents. Projects for temporary Analytical Normative Documents on reference standards of Grosheimin and Cynaropicrin were developed in accordance with requirement of State Pharmacopeia of the Republic of Kazakhstan. On the basis of obtained results the database for State Pharmacopoeia of the Republic of Kazakhstan will be formed, as well as control over production of new pharmaceuticals from Chartolepis intermedia Boiss. and Saussurea salsa (Pall.) Spreng.

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Chemical and biological modification of cynaropicrin and grosheimin: a structure–bitterness relationship study

Cited by 34 publications

References 24 publications

Cynaropicrin: A Comprehensive Research Review and Therapeutic Potential As an Anti-Hepatitis C Virus Agent

Cynaropicrin: A Comprehensive Research Review and Therapeutic Potential As an Anti-Hepatitis C Virus Agent

BitterDB: a database of bitter compounds

Reference Standards Based on the Grosheimin and Cynaropicrin

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