Silybum marianum

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Silybum marianum (Compositae/Asteraceae) is a biennial thistle-like plant (milk thistle) common in the Mediterranean area of Europe. The seeds yield 1.5-3% of flavonolignans collectively termed silymarin. This mixture contains mainly silybin (Figure 4.44), together with silychristin (Figure 4.45), silydianin (Figure 4.46), and small amounts of isosilybin (Figure 4.45). Both silybin and isosilybin are equimolar mixtures of two trans diastereoisomers. Silybum marianum is widely used in traditional European medicine, the fruits being used to treat a variety of hepatic and other disorders. Silymarin has been shown to protect animal livers against the damaging effects of carbon tetrachloride, thioacetamide, drugs such as paracetamol, and the toxins a-amanitin and phalloin found in the death cap fungus (Amanita phalloides) (see page 433). Silymarin may be used in many cases of liver disease and injury, though it still remains peripheral to mainstream medicine. It can offer particular benefit in the treatment of poisoning by the death cap fungus. These agents appear to have two main modes of action. They act on the cellular membrane of hepatocytes inhibiting absorption of toxins, and secondly, because of their phenolic nature, they can act as antioxidants and scavengers for free radicals which cause liver damage originating from liver detoxification of foreign chemicals. Derivatives of silybin with improved water-solubility and/or bioavailability have been developed, e.g. the bis-hemisuccinate and a phosphatidylcholine complex.

OH O

OH O

isosilybin (diastereoisomeric pair)

radical ° coupling

OH O

isosilybin (diastereoisomeric pair)

If OH HO

O OMe

OH O

radical ° coupling

OH O

Figure 4.46

OH O

OH O

If OH HO

OH O

OH O

silychristin

OH O

silychristin

Figure 4.45

(i) nucleophilic attack of enolate on to quinonemethide

(ii) hemiketal formation

OH O

silydianin

OH O

silydianin

Figure 4.46

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