Alkaloid Studies. I. The Isolation of Pilocereine from the Cactus Lophocereus schottii¹

Systematic Anatomy and Phylogeny of Mexican Columnar Cacti

“…Justification for this segregation was that the growth habit of Machaerocereus is more lax than in Lemaireocereus; spine clusters are well developed and bear a strongly flattened, downward-pointing central spine; and the perianth is very elongate and relatively long persistent. Although the triterpenes of each Machaerocereus species is different (Djerassi, 1957), these taxa have similar hypodermal silica bodies and seeds, and the flowers and fruits are quite similar, though the parts are darker colored in gummosus. On the basis of gross similarities in vegetative form, stem anatomy, triterpene chemistry, and seed structure, machaerocerei are more closely related to S. stellatus than to other cacti examined.…”

“…Heliabravoa) and most species of Stenocereus (incl. Machaerocereus and Rathbunia) recognized in this study except S. deficiens from South America, which is reported to have only traces of these compounds (Djerassi, 1957). Stenocereus chacalapensis, S. chrysocarpus, S. fricii, S. laevigatus, S. martinezii, and S. standleyi have never been examined for triterpenes, and triterpenes in the rathbunias have not been identified (Bird, 1974).…”

“…So far, pilocereine has been discovered in both species of Lophocereus (Djerassi et al, 1953;Djerassi et al, 1954;West et al, 1975) and in Pachycereus marginatus (Djerassi et al, 1954), and two related alkaloids, piloceredine and lophocerine, occur in Lophocereus schottii (Djerassi et al, 1958). Simple tyramine alkaloids occur in other species, including carnegine in Carnegiea gigantea and Pachycereus pecten-aboriginum (see Willaman TABLE 1.…”

“…Summary of triterpenes isolated from saponins (glycosides) from stems of Pachycereeae. Unless indicated by a footnote, reports are cited in Djerassi (1957 & Schubert, 1961); gigantine (Hodgkins et al, 1967;Agurell, 1969), an isomer of pellotine (Brown et al, 1968), and salsolidine (Bruhn et al, 1970) in C. gigantea; anhalonidine in Pachycereus weberi (Djerassi et al, 1954); and 3-hydroxy-4-methoxyphenethylamine in P. pecten-aboriginum (Agurell et al, 1971). Dopamine, the precursor of these alkaloids, occurs at high concentrations in C. gigantea (Steelink et al, 1967) and Pachycereus hollianus (Sa'nchez Mejorada, pers.…”

Simple Isoquinoline Alkaloids

“…Rhamnaceae: Ziziphus amphibia ( 135 (Methyl ether) 153-155°(hexane) (138, 140) 133-135°(EtOAc) (138) (Ethyl ether) 90-95°/15 2-153°(hexane) (138) (Acetate) 186-186.5°( Et2Q/Me2CO) (140) (Dihydrochloride dihydrate) 228-232°( dec.) (MeOH/EtOAc) (140) (Diperchlorate) 214-217°(dec.) (MeOH/EtOAc) (140) (Dimethiodide) 233-244°(dec.) (MeOH/EtOAc) (140) UV: (140,133) IR: (140, 133) MS: (Methyl ether) 757 (139) Sources:…”