Fritillaria and Veratrum Alkaloids

Several biogenetically important alkaloids have been isolated from Veratrum grandiflorum plants that had been grown in the presence of light.61 This system 

Kaneko, N. Kawamura, M. Tanaka, and H. Mitsuhashi, Koen Yoshishu-Tennen Yuki Kagobutsu Toronkai, 22nd, 1979, 55 (Chem. Abstr., 1980, 93, 8387) cf. K. Kaneko, N. Kawamura, T. Kuribayashi, M. Tanaka, and H. Mitsuhashi, Tetrahedron Lett., 1978, 4801. 

The structure (29) of epirubijervine was deduced mainly on the basis of XH and 13C n.m.r. data, and was confirmed by direct comparison with authentic material.62 

The crystal structure of 3-O-acetylveramarine (30) has been reported.63 Pseudojervine, veratrosine, veratramine, jervine, and a new alkaloid, verdine, have been isolated from V. dahuricum. It was suggested that the new alkaloid possesses the jervanine skeleton.64 Underground parts of V. nigrum have yielded 

Edpetisidinine (31), isolated from Petilium eduardi (Fritillaria sp.), has been assigned the structure and stereochemistry indicated, on the basis of spectroscopic studies on the alkaloid and its derivatives.68 

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The c.d. spectra of a number of Veratrum and Fritillaria alkaloids have been discussed.80... 

Kutney has reviewed the research of his group on the total synthesis of Veratrum and Fritillaria alkaloids. ... 

These alkaloids are widely used today in the treatment of hypertension. Medicinally, the most important alkaloids of Veratrum are the polyesters of protoverine (87) that have hypotensive properties. Plants from Veratrum and Fritillaria have been used in Chinese traditional medicine (Han et al., 1988). 

In Veratrum and Fritillaria (Lihaceae) C-nor-D-homosteroid alkaloids with 27 C-atoms are found. These substances are linked to sugars at the C-3 hydroxy group and many carry acyl residues attached to other OH-groups. Two typical representatives are veratr amine and ver ace vine. 

At least 450 steroid and triterpenoid alkaloids have been reported (Verpoorte et al., 1991). Most steroidal alkaloids occur in a relatively small number of genera (Cestrum, Cy-phomandra, Lycopersicon, Nicotiana, and Solanum) of the family Solanaceae and of the family Liliaceae (Fritillaria, Veratrum, and Zygadems). Related alkaloids are known from the Apocynaceae (Funtumia, Holarrhena, and Ma-louetia) and Buxaceae. Alkaloids based on triterpenoid structures are much less common. Probably the best known ones are found in plants of the Buxaceae (especially Buxus, Pachysandra, and Sarcococca) (Gross et al., 1985 Roddick, 1980, 1986). 

Alkaloids with a benzofluorene skeleton are foimd in the Veratrum, Schoenocavion, Zygadenus and Fritillaria genera of the liliaceae family. Many of the alkaloids occur as glycosides in the plants. Some are important starting materials for syntheses of steroid hormones. 

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