Description
This alkaloid is of widespread occurrence, being found in Stemmadenia species
and also is Vocanga africana, v. dregii and V. obtusa. It forms colourless needles
when crystallized from MeOH and has [0'10 - 42° (c 1.0, CHCI3). It sublimes under vacuum at 135°CjO.01 mm and is readily soluble in CHC13 or Me2CO, but
only sparingly so in EtOH or MeOH. Hydrolysis with KOH followed by acidification
with HCl yields Ibogaine (q.v.).
Definition
ChEBI: (-)-voacangine is a monoterpenoid indole alkaloid with formula C22H28N2O3, isolated from several plant species. It has a role as an angiogenesis inhibitor, an antineoplastic agent and a plant metabolite. It is a monoterpenoid indole alkaloid, a tertiary amino compound, a methyl ester, an organic heteropentacyclic compound and an alkaloid ester. It is a conjugate base of a (-)-voacangine(1+).
References
lanot, Goutarel., Compt. rend., 241,986 (1955)
Stauffacher, Seebeck., Helv. Chim. Acta, 41,169 (1958)
Watts, Collera, Sandoval., Tetrahedron, 2, 173 (1958)
Schuler, Verbeck, Warren.,J. Chern. Soc., 4776 (1958)
Bartlett, Dickel, Taylor.,J. Amer. Chern. Soc., 80, 126 (1958)
Renner, Prins, Stoll., Helv. Chim. Acta, 42,1572 (1959)
Budzikiewicz etal., Bull. Soc. Chim. Fr., 1899 (1963)
