Febrifugine from Dichroa febrifuga

The antimalarial properties attributed to preparations from Dichroa febrifuga by the Chinese were confirmed about 1944 and two alkaloids, febrifugine (999) and isofebrifugine (1000), were isolated eventually. After difficult structural elucidations, syntheses of ( )-febrifugine followed it proved to be half as active as the natural material, itself far better than quinine, but the therapeutic index was disappointingly low (67HC(24-l)490). 

Apparently, febrifugine (41) and isofebrifugine (42) isolated from Dichroa febrifuga have anti-moth activity. Peganum harmala has been shown to elaborate a new alkaloid, pegalol (37 R = H, OH, R = H). The seasonal patterns of peganine (37 R = H2, R = OH) distribution in the roots and ripe seeds of P. harmala have been determined. ... 

Yasuo T, Miyo O (2005) Concise Synthesis of dl-Febrifugine. Chem Pharm Bull 53 868-869 Koepfli JB, Mead JF et al (1947) An alkaloid with high antimalarial activity from Dichroa febrifuga. J Am Chem Soc 69 1837... 

Febrifugine has a history as a malaria remedy which dates back to the first recorded use of Ch ang Shan in China, 200 B.C. It is an alkaloid which is apparently fairly widely distributed in the roots and leaves of plants of the family Saxifragaceae, and has been isolated both from the leaves of the common hydrangea in the United States and from the roots of Dichroa febrifuga Lour. The alleged antimalarial activity of the latter crude plant material has been confirmed by a number of modem investigators (93, 96-99). As a consequence of the careful and independent studies of both American and Chinese workers (100-106), the active alkaloid has been... 

Febrifugine was first isolated from roots of Dichroa febrifuga Lour. (Saxifragaceae), a Chinese medicinal plant traditionally used to treat malaria fevers. This alkaloid showed potent anti-Plasmodium activity, which was superior to quinine, and tmacceptable side effects, such as hepatotoxicity and severe emesis [128,129]. Its properties not only precluded its use as drug but also encouraged the synthesis of safer analogues [127]. 

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