Antispasmodic Activity of Fractions and Cynaropicrin from Cynara scolymus on Guinea-Pig Ileum

Abstract

Cynara scolymus (Compositae), popularly known as "alcachofra" or "artichoke", is widely cultivated In Mediterranean and American countries, and its sprout is commonly eaten as a vegetable. Its leaves are frequently used in folk medicine in many countries, to treat several ailments, including hepatitis, hyperlipidemia, and obesity, dyspeptic disorder, among others. Clinical and pre-clinical trials have confirmed the therapeutic potential of this plant, particularly in the treatment of hepato-biliary dysfunction and digestive complaints, and also its effectiveness in patients with irritable bowel syndrome and hyperlipoproteinemia, as well as its choleretic and antioxidant effects. 1-5)The literature reports several phenolic compounds as the main chemical constituents of artichoke leaves, such as cynarin, caffeic and chlorogenic acids, luteolin, cynaroside and scolymoside, and sesquiterpenes, such as cynaropicrin, which are indicated as the active principles of this plant. [6][7][8][9] In previous studies conducted in our laboratories, we have described the chemical and biological activities (cytotoxic and diuretic) of artichoke cultivated in Brazil. Our results showed that the main constituents are glycosyl flavonoids (cynaroside and scolymoside), along with cynaropicrin and lupeol.10) More recently, we have also demonstrated that methanolic extract of C. scolymus exhibits an antispasmodic profile against the action of acetylcholine on preparations with isolated guinea-pig ileum and rat duoden, by using experimental models in vitro. 11)In order to elucidate the antispasmodic component(s) of this plant, we carried out a bio-guided assay against acetylcholine in guinea pig-ileum. MATERIAL AND METHODS Plant Material, Preparation of Fractions and Isolation of CynaropicrinLeaves of Cynara scolymus were picked, in February 2000, from the "Central de Plantas" at Curitiba, in the State of Parana, southern Brazil. Air-dried leaves (1900 g) were macerated with methanol at room temperature for approximately 7 d, followed by the removal of solvent under reduced pressure to obtain the crude methanolic extract (CME). Afterwards, the CME was suspended in water and successively partitioned with solvents of increasing polarity (hexane, dichloromethane, ethyl acetate and butanol), yielding the respective fractions, according to the method previously described.12) The most active fraction, dichloromethane, was studied in more detail, and the most potent subfraction furnished the compound cynaropicrin, which was directly compared with an authentic sample previously isolated by us.10) All the fractions and compounds were dissolved in ethanol solution (10%) at the desired concentration, immediately prior to biological use.Animals Guinea-pigs (300-400 g) of both sexes were kept in automatically controlled temperature conditions (23Ϯ2°C), in 12 h light-dark cycles and with food and water "ad libitum". The animals were kept in the laboratory for 48 h prior to the experiments and their food was restrained 24 h before the experiments.Evalua...

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

“…In addition, after successive washings, the contractile response to agonists was restored. These findings are consistent with the popular use of artichoke as a home remedy for the treatment of gastrointestinal disturbances (Emendörfer et al, 2005). In the same context, another recent study showed that cynaropicrin has a weak in vitro acetyl cholinesterase inhibition with an IC 50 value of 10 μg/ml and radical scavenging activity against 1,1-diphenyl-2-picryl-hydrazil (DPPH) radicals (Hegazy et al, 2016).…”

Sesquiterpenoids in subtribe Centaureinae (Cass.) Dumort (tribe Cardueae, Asteraceae): Distribution, 13C NMR spectral data and biological properties

“…The dichloromethane fraction showed the most promising biological effects, with an IC 50 of 0.93 (0.49-1.77) lg/mL. Its main active component, the sesquiterpene lactone cynaropicrin, exhibited potent activity, with IC 50 of 0.065 (0.049-0.086) lg/mL, being about 14-fold more active than dichloromethane fraction and having similar potency to that of papaverine, a well-known antispasmodic agent (Emendoerfer et al, 2005).…”

Supercritical fluid extraction of cynaropicrin and 20‐hydroxyecdysone from Leuzea carthamoides DC

“…It has recently been shown that cynaropicrin (Fig. 1) has an antispasmodic activity [21], is a potent, irreversible inhibitor of the bacterial enzyme MurA [22], may participate in inflammatory response by inhibiting the production of inflammatory mediators and the proliferation of lymphocytes [23], shows significant cytotoxicity against five cultured human tumour cell lines [24] and may be a potential anticancer agent against some leukocyte cancer cells such as lymphoma or leukaemia [25]. It is desirable to remove the bitter compounds selectively from the leaves of L. carthamoides, as the extract could be used in the food industry and in the animal production as an additive to feedstuff to improve the digestion of monogastric animals and galliformes, while the ecdysteroids would be extracted from the leaves in the next step by an organic solvent.…”