Veratrum lobelianum

Veratrum lobelianum Veratrum californicum 0-ace ty Ifervine Jervine Cyclop amin Cycloposine Protoveratrine A Protoveratrine B... 

Suladze, T. S. and Vachnadze, V. Y. 2002. Alkaloids of Veratrum lobelianum growing in Georgia. Chemistry of Natural Compounds, 38(5) 470. 

Veralozidine (97) (C27H43NO2 mp 153-155° [a] —92.2° in ethanol) was isolated from the green part of Veratrum lobelianum 69). The mass spectrum of veralozidine exhibited a fragmentation pattern indicative of a 22,26-epiminocholestane skeleton. The UV spectrum of this alkaloid showed a maximum attributable to the C=N double bond. Veralozidine displayed IR absorption due to a hydroxy, a 3jS-hydroxy-5-ene, and a C=N group. 

Alkamine X (mp 215-217°) was found in Veratrum lobelianum its IR spectrum exhibited absorption due to a double bond and a hydroxy and an amino group (58). 

The alkaloid constituents of Veratrum lobelianum have been the subject of continuing close scrutiny.Veralosidinine and veralodisine have recently been isolated from this plant and have been assigned the structures (18) and (19), respectively. 

Saffron genus Colchicum (Colchicum L.) produces colchicines. Metacolchicine is in Sandersonia aurantiaca and other colchicines in meadow saffron (Colchicum autumnale L.). Stereoidal alkaloids in the Liliaceae family are found in the Hellebore genus (Veratrum Bemch.). Jervine, cyclo-pamine (Figure 1.18), cycloposine, protoveratrine A, and protoveratrine B yield Veratrum album. Veramadines A and B are reported to be found in Veratratum mackii var. japonicum. O-Acetyljervine has been reported in the false hellebore (Veratrum lobelianum Bemch.). Steroidal alkaloids... 

ShaMrov R, Kul kova VV, Nakhatov 1 (1995) Alkaloids of Veratrum lobelianum verdinine and 3,15-Dl-0-(2-methylbutyroyl)germine. Chem Nat Compd 31(l) 79-82... 

Jervine has also been recorded from other Veratrum spp., e.g., V. nigrum, V. lobelianum and V. grandiflorum and veratrine-like alkaloids in Zygadenus spp. (p. 779). 

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... 

Veracintine (134) was isolated from the part of Veratrum subsp. lobelianum (77) which is above the ground. By catalytic hydrogenation the alkaloid afforded, in ethanol, a dihydro derivative (135) in acetic acid, tetrahydroveracintine (136). The amorphous iV, 0-diacetyl derivative (137) was isolated in the reaction of veracintine with acetic anhydride in pyridine. The bands in the IR spectrum of 137 showed the amido group and the presence of a double bond. The absorption in the UV... 

Kaneko et al. proposed that cholesterol is an important precursor in the biosynthesis of Veratrum alkaloids 126). Cholesterol [4- C]-3-phosphate and cholesterol [26- C] were used as precursors in Veratrum grandifiorum Loesen. fil. to establish them as biological precursors of Veratrum alkaloids. Cholesterol was incorporated in very small quantities (0.01%) only in jervine and veratramine. Cholesterol [4- C] fed to V. album subsp. lobelianum by the cotton wick method was found not to be incorporated into jervine and veratroylzygadenine 128). 

Synonyms Veratmm album ssp. lobelianum (Bemh.) Schuebl. Martens, Veratrum album ssp. virescens (Gaudin) Jav. ... 

Soo, Veratrum album var. lobelianum (Bemh.) Koch, Veratmm album var. virescens Gaudin. 

Isolated from Veratrum album subsp. lobelianum-, containing one ace-toxy, one hydroxy, and one ketone group the authors (144) assumed a similarity with tomatillidine, for which, however, a new structural formula was proposed later (172) , Huang-Minlon reduction of deacetylveralodisine led to veralosidine (144). 

Isolated from Veratrum album subsp. lobelianum probably 0(16)-acetyletioline (cf. 142). By CD the (2S5)-configuration was demonstrated... 

Veralkamine, C27H43NO2, which does not have the structure previously suggested 289), the related veramine, C27H41NO2, and vera-linine, C27H43NO, which are minor alkaloids from Veratrum album subsp. lobelianum 184, 187, 227), appear to be compound.s with the... 

No new jerveratrum glycoalkaloids appear to have been isolated since the last review (Volume VII). However, Tomko and collaborators have reported isolation of pseudojervine from Veratrum album subsp. lobelianum (Bernh.) Suessenguth (9). 

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