Veratrum album

In addition to the alkaloids such as cyclobuxiae-D (129) and solanidine (130) where the stmctural similarities to steroids are clear (although it must be remembered that detailed evidence actually linkiag the compounds is lacking) there are the less obvious (but nonetheless also clearly related) Veratrum alkaloids. These compounds, of which protoverattine A [143-57-7] (131), obtained from the rhizome of Veratrum album L. (LiUaceae), is a... 

Steroid alkaloids Solanaceae Liliaceae Solanum tuberosum Lycopersicon esculentum Veratrum album Solanidine Tomatine Jervine Cyclop amine Cycloposine Protoveratrine A Protoveratrine B... 

Veratrum album L. and Schoenocaulon officinale (Lindl.), Liliaceae, Ang. 

Even (R)-2-methylbutanoic acid of high enantiomeric purity (more than 99%) has been reported as a natural compound in the extract of the steroid alkaloid containing drug Veratrum album L. [40]. 

Schoenocaubn officinale [seed], Veratrum album, V. mride [rhizome] (Liliaceae) (Liliaceae)... 

An alkaloid obtained from white veratrum, Veratrum album (Liliaceae). 

The steroidal alkaloids have a nucleus based on 21, 24, or 27 carbon atoms (Fig. 44). The C21 alkaloids are pregnane-derived with nitrogen inserted at C-3, at C-20, or at both positions. They are characteristic of the Apocynaceae Funtumia and Holarrhena species) and the Buxaceae Buxus species). The Buxaceae also produces C24 alkaloids based on the cycloartane skeleton. The most interesting alkaloids are those in the Solanaceae and the Liliaceae. These are C27 alkaloids, and examples include solasodine and solanidine many derivatives are glycosylated. The alkaloids from the Liliaceae, such as veratramine of the white hellebore (Veratrum album), were formerly used for cardiac... 

Quatrehomme G, Bertrand F, Chauvet C, Ollier A. Intoxication from Veratrum album. Hum Exp Toxicol 1993 12(2) 111-15. 

Gaillard Y, Pepin G. LC-EI-MS determination of veratri-dine and cevadine in two fatal cases of Veratrum album poisoning. J Anal Toxicol 2001 25(6) 481-5. 

Marinov A, Koev P, Mirchev N. [Electrocardiographic studies of patients with acute hellebore (Veratrum album) poisoning.] Vutr Boles 1987 26(6) 36-9. 

Gamier R, Carlier P, Hoffelt J, Savidan A. Intoxication aigue ahmentaire par I eUebore blanc (Veratum album L.). Donnees chniques et analytiques. A propos de 5 cas. [Acute dietary poisoning by white hellebore (Veratrum album L.). Chnical and analytical data. A propos of 5 cases.] Ann Med Interne (Paris) 1985 136(2) 125-8. 

Veratrine.— This alkaloid, with a composition of C37H53NOU, is found in varions parenchyma cells of Veratrum album. If sections of the rhizome or roots are mounted in 2 drops of water and a drop of concentrated H2SO4 and examined microscopically on a glass slide, the cell contents and walls of the cells which contain this substance first take a yellow color which soon changes to an orange-red and then to a violet. 

Veratrum album. White hellebore. Veratrum album. W. IV. 895. Radix. The root. 

Veratrum alkaloids are produced by lilaceous plants of the suborder Melanthaceae of which Veratrum album, the hellebore of Europe and northern Asia, Veratrum viride, the swamp hellebore or Indian poke of North America, and Schoenocaulon officinale of Central and South America are the best known. The latter yields the sabadilla seed which was used as an insecticide by Indians in pre-Columbian times (Crosby 1971). The alkaloid fraction of the seeds, often termed veratrine, is a poorly defined mixture mostly of the ester alkaloids, veratridine, and cevadine and of the alkamine veracevine or its isomer cevine. 

The empirieal formula of veratrobasine (11) isolated from Veratrum album L. 13,14) was revised and the structure, including the stereochemistry, determined by means of X-ray diffraction analysis (15). 

Removal of the iV-acetyl group yielded the product 58 which is identical with authentic verarine isolated from Veratrum album subsp. lo-belianum. 

The structure of two novel esters of germine containing an aromatic acid was elucidated as follows (57). Both alkaloids isolated from Veratrum album subsp. lobelianum were cleaved by alkaline hydrolysis to germine (82) and isogermine (83), respectively. One mole equivalent of veratric acid was isolated from the acidic portion after saponification of 84. In addition, compound 85 afforded one mole of acetic acid (53). 

Veralinine, a minor alkaloid from Veratrum album subsp. lobelianum, also has the rearranged 22,26-epiminocholestane skeleton (74). From chemical and spectroscopic evidence this Veratrum base is regarded as (22S,25S)-22,26-epimino-17/3-methyl-18-Jior-cholesta-5,12-dien-3 iS-ol (118). This structure was confirmed by correlation with veralkamine. The ketone 115 prepared from veralkamine was treated with ethanedi-thiol. Desulfurization of the resultant thioketal 119 with Raney nickel yielded the C-16 deoxo compound 120, which is identical with (22S,25S)-22,26-acetyl-epimino-17 3-methyl-18-7ior-5a,13a-cholestan-3j8-ol, also prepared from veralinine (118) via catalytic hydrogenation... 

The crude drug "protoveratrine", from Veratrum album, consists of two main compounds, namely protoveratrines A (26a) and B (26b). 

Although Veratrum no longer poses a problem for sheep in the lower 48 states of the United States, a recent outbreak of cyclopia was reported in domestic alpacas in 1995 and 1996 in Alaska (K.E. Panter J. Leach, personal communication). Suspect plants in the vicinity grazed by the alpacas included Veratrum album, from which several jerveratrum alkaloids have been isolated and which are likely responsible for the induction of cyclopia in the alpaca llamas [33-35]. 

The rhizome of Veratrum album, A native of the mountainous regions of central and southern Europe. 

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