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Cyclamin

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Cyclamin

Cyclamin is an organic compound that has been used by the pharmaceutical industry as an ingredient for nasal sprays.

Research on the cytotoxic and anticlastogenic activities of the cyclamen genus has been limited. In the 1950s and 1960s little research was done on the toxic saponin cyclamin, but no further investigation has recently been performed. Cyclamin, a triterpenoid pentasaccharidic saponin, has previously been extracted from different cyclamen species, including Cyclamen mirabile, Cyclamen trocopteranthum, Cyclamen libanoticum and Cylamen persicum.

Cyclamin can be extracted from cyclamen plants such as the species mirabile and trocopteranthum. Cyclamen are known houseplants; this raises concerns about the awareness of the toxicity of this flower. The compound cyclamin belongs to the family of triterpene saponins, which are derived from the saponin structure. Triterpenoid compounds contain one or more sugar moieties attached to triterpenoid aglycones. The large diversity of structures causes saponins to exhibit a wide range of biological and pharmacological properties. In China, cyclamin has been used as a traditional medicine for years. Cyclamen has been used against menstrual disorders, digestive disorders, and anxiety in women. However, this is only the case for the leaves, the roots of the plants are known to be harmful if ingested. In these roots, cyclamin is found, as well as in the bulbs. Therefore, cyclamin is suspected to be the compound which causes the toxicity of these roots and bulbs in cyclamen plants.

As can be seen in Figure 1, cyclamin consists of a hydrophilic part with five connected saccharide groups. The second part of the cyclamin molecule consists of a non-polar, sterol-like backbone. These two different parts make that cyclamin molecules, and saponins in general, are highly amphipathic compounds. However, the exact mechanism of action of cyclamin has not been extensively researched. The structure-activity relationship (SAR) of cyclamin is not yet known.

The amphipathic nature of cyclamin makes the compound permeable through the membrane. The carbohydrate part of saponins is water-soluble, making them surface-active. Cyclamin is known as a white opaque substance obtained in solid form that absorbs up to 45% water. Upon absorption of water, it becomes a transparent substance. Furthermore, it is soluble in alcohol and turns brown when exposed to light. Saponins overall are known to be soluble in polar solvents. Except for alcohol and water, cyclamin has not been further tested. When dissolved in water, it produces foam by frothing test and upon heating it has the unique property of coagulation. Concentrated sulfuric acid colours cyclamin in purple red, which disappears with water addition.

Not much is known about the mechanism of action of cyclamin. However, a study proposed possible mechanisms of action based on their experimental results. Firstly, cyclamin might activate the proteins caspase-3, caspase-8 and caspase-9. Caspases are proteins that can induce apoptosis when being activated.

Secondly, cyclamin could be responsible for increasing the expression levels of the cyclin-dependent kinase 2 and the cell division cycle 25 homolog A. This can lead to increased DNA synthesis and cell proliferation and an increase in signal transduction pathways.

Thirdly, cyclamin could increase the ratio of Bax/B-cell lymphoma 2 expression. This would favour apoptosis to take place.

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