Echimidine

Russian comfrey (Symphytum x uplandicum Nyman) is widely recommended as a medicinal herb and an item of human diet. A previous investigation of this species led to the isolation of three alkaloids which were not fully characterized (cf. Vol. 7, p. 57). Culvenor and co-workers have separated eight pyrrolizidine alkaloids from the leaves of this perennial plant by counter-current distribution.21 The known alkaloids echimidine (51), symphytine (52), lycopsamine (53), and intermedine (54) were present. In addition, four new alkaloids, i.e. 7-acetyl-lycopsamine (55), 7-acetylintermedine (56), symlandine (57), and uplandicine (58), were characterized by spectroscopic methods, and by hydrolysis. The total alkaloidal extract caused chronic hepatotoxic effects in rats, and the authors... 

Echimidine Symphytine Lycopsamine Intermedine 7-Acetyl-lycopsamine 7 - Acetylintermedine Symlandine Uplandicine... 

Echimidine (33) and anadoline (34) have been isolated from Symphytum tuberosum of Turkish origin.16 Extraction of the dried aerial parts of Lindelofia anchusioides gave 1.4% of lindelofine (35) by an ion-exchange method.17... 

Echium seeds, hke other members of family boraginaceae, contain pyrrolizidine alkaloids. The seeds contain echimidine as a major alkaloid and many minor alkaloids, including retronecine, lycopsamine, 7-acetyUycopsamine, and their derivatives. 

Fig. 3.6. HPLC separation of some Symphytum alkaloids Column MN-Nucleosil C18 10 urn (300x4 mm ID), mobile phase methanol - water (45 55), flow rate 2 ml/min, detection UV 220 nm. Peaks 1, echimidine N-oxide 2, symphytine N-oxide. (Reproduced with permission from ref. 18, by courtesy of Hippokrates Verlag)...

Echimidine.echinatine, symphytine Purification and separation alkaloids from Boraginaceae XAD. 50-100 pm or 74-250 pm 260x13, 610x20, 150x10 MeOH - H,0 in various ratios, gradients and pH MeOH - H20(1 1)+ HCl(pH 3.5) 15... 

Comfrey is a perennial herb used for the prevention of kidney stones nourishing and repairing bone and muscle and for the treatment of injuries such as burns and bruises. In Australia, comfrey is classified as a poison and its sales have been restricted in several regions. Many different commercial forms of comfrey are marketed, including oral and external products. Commercial comfrey is usually derived from the leaves or roots of Symphytum officinale (common comfrey). However, some products are also derived from Russian comfrey. Russian comfrey contains a very toxic pyrrolizidine alkaloid, echimidine, which is not found in common comfrey. However, common comfrey contains other hepatotoxic alkaloids, namely 7-acetylintermedine, 7-acetyllycopsamine and symphytine. The metabolites of these alkaloids are very toxic to the liver. Ridker et al. documented hepatic venocclusive disease associated with consumption of comfrey root. Long-term smdies in animals have also confirmed the carcinogenicity of comfrey in animal models. ... 

Commercial comfrey is usually derived from the leaves or roots of Symphytum officinale (common comfrey) (USP, 1998). However, some products are derived from Symphytum x uplandicum Nyman (Russian comfrey) or Symphytum asperum Lepech (prickly comfrey), which appear to be more toxic than common comfrey (Anonymous, 1998). Russian comfrey and prickly comfrey contain a very toxic pyrrolizidine alkaloid (PA) called echimidine that common comfrey does not contain (Tyler, 1994). Although common comfrey does not contain echimidine, it does contain other hepatotoxic PAs. These alkaloids include 7-acetylintermedine, 7-acetyllycopsamine, their unacetylated precursors, and symphytine (Tyler, 1993). 

Echiumine, echimidine, 7-acetylcopsamine, acetintermedine, intermedine, acetylechimidine... 

Acetyllycopsamine, 7-acetylintermedine, symlandine, uplandicine, echimidine, symphytine, lycopsamine, intermedine, echiumine... 

Echimidine C oHjiNO, Echinatine C15H..NO. Echium plantagineum L. (88) Rindera echinata (89) 13.4° < ... 

Dibsters of Nbcine and Two Different Monocarboxylic Acids a. Echimidine (retronecine and angelic, echimidinic acids). 

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