Melilot Coumarins

Coumarin, mp 68°C, is a colourless crystalline compound it is the aromatic principle in woodruff and also occurs in other plants, e.g. lavender and melilot. Coumarin is prepared from salicylaldehyde by a Perkin reaction with acetic anhydride or by cyclocondensation with 1,1-dimorpholinoethene [27] ... 

Electroreduction of Coumarin. The principal cathodic reaction of coumarin is the reduction to melilotic acid (Fig. 10.18). A second reduction product is an approximately equimolar mixture of o-hydroxyphenylpropanol and o-propylphenol (Fig. 10.18). Hence, there are three reactions involving coumarin. 

Melilotus alba Medicus M. indica (L.) All. M. suaveolens Ledeb. Be Han Cao (Clover) (whole plant) Hydroxycinnamic acid, coumarinic acid, 4-hydroxycinnamic acid, cumaric acid, umbelliferone, scopoletin, melilotoside, melilotic acid, beta-D-glucosyloxy, dicumarol, chlogogenic acid, caffeic acid, melilotic acid.48 Anticoagulant, treat bowel complaints, infantile diarrhea. A bactericide. 

Coumarin constituents (black cohosh, chamomile, fenugreek, horse chestnut, sweet melilot, tonka beans, sweet woodruff). Naturally occurring coumarins are only weakly anticoagulant, but improper storage causes the production of dicoumarol by microbial transformation. Woodruff may contain constituents of warfarin... 

Coumarin is found in a large number of plants belonging to many different families including tonka beans, woodruff, lavender oil, cassia, melilot (sweet clover), and other plants. It is found in edible plants such as strawberries, cinnamon, peppermint, green... 

Phytochemistry The herb contains coumarins, mehlotin, melilotic add, melilotocide, purine derivatives, essential oil, vitamins C and E, carotene, protein, and lipids. The seeds contain protein, fatty oils, starch, and alkaloids (Tolmachev 1976 Khalmatov et al. 1984 Chikov 1989 Martino et al. 2006). 

The action of promoting cell elongation by coumarin is related to the intact structure of the molecule [104]. Some derivatives have shown inhibition at the same concentrations at which coumarin exerted an activation. Particularly hydroxy substitution elicited this adverse effect, whereas methyl and halogen replacement only reduced the stimulatory action. Open ring derivatives, o-coumaric and melilotic (o-hydroxyphenylpropionic) acids, were also less active than coumarin [97]. 3- and 4-Hydroxycoumarins were not only inhibitors of growth stimulation but these compounds counteracted the enhancing action of coumarin. 

Coumarin Yeiiow sweet ciover ( yeilow melilot) Melilotus officinalis... 

The true melilot Melilotus officinalis) is thoroughly resistant to drought but its content of bound coumarin is troublesome to cattle and, in addition to this, the highly poisonous dicoumarol can be formed from its precursors. On the other hand, certain crosses among the related white... 

---