Alkaloids hydrangea

Hydrangea umbellata Rheder (Saxifragaceae). A Chinese anti-malarial drug said to contain several crystalline alkaloids. (Jang, Fu, Huang, Wang, Nature, 1948, 161, 401.)... 

In addition to lupines, poison-hemlock and Nicotiana spp., other plant species of the genera Genista, Prosopis, Lobelia, Cytisus, Sophora, Pinus, Punica, Duboisia, Sedum, Withania, Carica, Hydrangea, Dichroa, Cassia, Ammondendron, Liparia, and Colidium contain potentially toxic and teratogenic piperidine alkaloids. Many plant species or varieties from these genera may be included in animal and human diets (Keeler and Crowe, 1984). 

Only three of 75 samples tested gave positive alkaloid tests Astilbe rivularis, Hydrangea arborescens, Vahlia capensis. 

Largely on the basis of the magnitude (7 Hz) of J13 (obtained by irradiation at the side chain methylene) in febrifugine acetate di-hydro-chloride [272] this derivative of the hydrangea alkaloid was assigned the trans configuration shown. (173)... 

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... 

The total alkaloid content of the Chinese root is 0.1-0.15% (43, 46), but that of Indian root is only about one tenth as great (46). The leaves of D. febrifuga also contain febrifugine (43, 44, 46), but in much smaller amount than the roots nevertheless, the leaves (known as Shuu Chi, or in Yunnan as Chunine ) have a high antimalarial activity and probably contain some other active alkaloid (44). Febrifugine has also been isolated from hydrangea leaves (51). 

Fabrifugina a quinolazine alkaloid isolated from the comon hydrangea, and from the shrub Dichroa febrifuga which has been used in Chinese folk medicine since ancient times, m.p. 139-140 C, [a]g -t6° (c = O.S in CHCI3). F. is a powerful antimalarial and antipyretic, but is too toxic for human use. 

Chang F-R, Lee Y-H, Yang Y-L, Hsieh P-W, Khalil AT. Chen C-Y, Wu Y-C (2003) Secoiridoid glycoside and alkaloid constituents of Hydrangea chinensis. J Nat Prod 66 1245-1248... 

Baker BR, Schaub RE, McEvoy FJ, Williams JH (1952) An antimalarial alkaloid from hydrangea. xii. synthesis of 3-[P-keto-y-(3-hydroxy-2-piperidyl) propyl]-4-quinazolone, the alkaloid. JOig Chem 17 132-140... 

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