Spiraea alkaloids

The genera of Aconitum (commonly known as Monkshood) and Delphinium, and to a lesser extent Rumex, Consolida, and Spiraea, have long been recognized as a rich source of alkaloid natural products [1], The diterpenoid alkaloids are generally classified into two major groups the Ci9-diterpenoid alkaloids (sometimes referred to as the Cig-norditerpenoid alkaloids) and the C2o-diterpenoid alkaloids. Within the C2o-diterpenoid alkaloids, at least 11 separate classes have been isolated, including the hetisine alkaloids (Chart 1.1). 

Spiraea salicifolia L. S. salicifolia L. var. grosseserrata Liou Liou fil. S. salicifolia L. var. oligodonta Yu Xiu Xian Jiu (Bridal wreath) (whole plant) Flavonoids, carotenoids, vitamin C, alkaloids, seed oil.33 Diuretic, treat cough, pain, monthly period, constipation. 

Diterpenoid alkaloids have been isolated from the genera of the families Ranunculaceae (Aconitum, Consolida, Delphinium, Thalictrum), Garryaceae (Garraya), Rosaceae (Spiraea), and Compositae (Inula). These alkaloids can be divided into two broad categories norditerpenoid alkaloids (based on a C -skeleton) and the diterpenoid alkaloids (based on a Cft-skeleton).1 The chemistry of the diterpenoid alkaloids has been reviewed in earlier literature. ... 

In 1964 Molodozhnikov and co-workers (137) reported the isolation of several diterpenoid alkaloids from the shrub Spiraea japonica L. fil. of the Roseaceae family. Later Goto and co-workers (138) examined alkaloids of the same plant (Japanese name Shimotsuke ) and isolated 10 new alkaloids. The structures of 3 of these, spiradine A (152), spiradine B (153), and spiradine C (154) have been determined by chemical correlations coupled with a single-crystal X-ray analysis (139) of spiradine A methiodide (155). 

Spiredine.—Gorbunov et al. ° have isolated the previously reported spiradine A (109), C20H25NO2, m.p. 280—282 C, and a new alkaloid, spiredine, from Spiraea japonica. This new base, C22H27NO3, m.p. 163 "C, was assigned structure (110) on the basis of the i.r. and n.m.r. spectral data and by a chemical correlation with spiradine A. Catalytic hydrogenation of spiredine gave (111), which is identical to the compound obtained by the addition of ethylene oxide to dihydrospiradine A (112). 

H. Diterpene Alkaloids from Spiraea japonica L. (Rosaceae). 187... 

Alkaloid from roots of Spiraea japonica var. incisa (Rosaceae). Needles (MeOH). Mp 237-239°. [a], —49 (c, 0.81 in CHCI3). 

Spiraea japonica L.6I., are three such alkaloids, although vakognavine (129) is novel in that it has a C(4)-aldehyde substituent rather than the N-CH4-C(4) linkage common to hetisine, hypognavinol, and spiradine A. More extensive variations of the basic hetisine skeleton are observed in delnudine (132) ... 

Nitrogenous Extractives 5.2J.2 Alkaloids from Mevalonate 5JJ,2J Spiraea Alkaloids... 

The presence of alkaloids in Spiraea japonica was reported by a Russian research group in 1964 (46). This plant is a small shrub, about 1 m high, belonging to the Rosaceae. It must be noted that the occurrence of alkaloids in Rosaceae plants is quite rare. Several alkaloids were isolated by Japanese researchers from the plant the structures of spiradine A and spiradine D are shown (54). 

Goto G, Sasaki K, Sakabe N, Hirata Y 1968 The alkaloids obtained from Spiraea japonica L. fil. Tetrahedron Lett 1369-1373... 

The hetisine natural products are a family of complex Cao-diterpenoid alkaloids isolated from the Aconitum, Con-solida. Delphinium, Rumex, and Spiraea genera, plants that have been widely used in traditional herbal medicine (Figure 16.10). Several of the more than 100 members... 

---