Alkaloids from Mammals

Akugin, E., and U. Pindur Chemische Eigenschaften und Synthese-Verfahren von 3-Vinylindolen. J. Heterocyclic Chem. 22, 585 (1985). 

Al-Ekabi, H., and P. De Mayo The Cds Photo-induced Dimerisation of N-Vinyl Carbazoles. Tetrahedron 42, 6277 (1986). 

Ascalone, V., and L. Dalbo Rapid and Simple Detection of Carpofen in Plasma by HPLC with Fluorescence Detection. J. Chromatography 276, 230 (1983). 

Banderanayake, M., M.J. Begeley, B.O. Brown, D.G. Clarke, L. Crombie, and D.A. Whiting Synthesis of Acridone and Carbazole Alkaloids Involving Pyridine Catalysed Chromene Formation Crystal and Molecular Structure of Dibromocanna-bicyclol and Its Bearing on the Structures of Cyclol Alkaloids. J. Chem. Soc. Perkin I, 999 (1974). 

Bergman, J., and B. Pelcman Synthesis of Carbazoles Related to Carbazomycin, Hyellazole and Ellipticine. Tetrahedron 44, 5215 (1988). 

---

The remaining two chapters provide fascinating insights into the alkaloids of mammals and of amphibians. As a follow-up to a chapter published in Volume 21 of this series, Arnold Brossi offers a critical review of the current status of the knowledge of mammalian alkaloids, such as those derived from tryptophan and from phenylalanine, and in particular he reviews the literature regarding the fascinating subject of whether morphine-like alkaloids are indeed mammalian metabolites. 

Alkaloids in mammals can be sequestered from vegetal or animal sources and are produced by the organism. It is known that morphine can be synthesized by mammalian cell from dopamine. This mammalian endogenous morphine is identical with vegetal morphine from Papaver somniferum It is empirically evidenced that human cells also can produce morphine. Exogenous alkaloids, depending on their bioactivities, can work in mammals in curative process of disorders and diseases and as hallucinogens or as poisons. Other mammalian alkaloids are well-known alkaloids such as beta-carbolines and isoquinolines. 

Many other bisben2ylisoquinoliae alkaloids, such as tetrandriae (80), from Cjcleapeltata Hook., are also known. Compound (80), for example, although it causes hypotension and hepatotoxicity ia mammals, ia other tests, possessed enough anticancer activity to be considered for preclioical evaluation (55). The arrow poison tubocurare prepared from Chondrendendron spp. also contains the bisben2yhsoquiQoline alkaloid tubocurariae (9). 

According to Biberfeld, palmatine, calumbamine and jatrorrhizine all paralyse the central nervous system in frogs palmatine also produces this effect in mammals and differs from the other two in stopping respiration, probably by paralysis of the respiratory centre. All three alkaloids lower the blood pressure on intravenous injection, palmatine being the most active. 

Copper oxidases are widely distributed in nature, and enzymes from plants, microbes, and mammals have been characterized (104,105). The blue copper oxidases, which include laccases, ascorbate oxidases, and ceruloplasmin, are of particular interest in alkaloid transformations. The principle differences in specificity of these copper oxidases are due to the protein structures as well as to the distribution and environment of copper(II) ions within the enzymes (106). While an in vivo role in metabolism of alkaloids has not been established for these enzymes, copper oxidases have been used in vitro for various alkaloid transformations. 

I want to mention that this alkaloid is of special interest because of its close resemblance to substances derived from the pineal gland of mammals. In particular, 10-methoxy-harmaline, which may be obtained in vitro from the incubation of serotonin in pineal tissue, resembles harmaline in its subjective effects and is of greater activity than the latter. This suggests that harmaline (differing from 10-methoxy-harmaline only in the position of the methoxy group) may derive its activity from the mimicry of a metabolite normally involved in the control of states of consciousness. 

Plant products have also been detected in non-plant organisms. Morphine 1, the archetypal plant alkaloid, has in fact been shown to be a physiological plasma constituent and its production in mammals could be traced to the liver expression of the critical enzymes of its biosynthesis.17 In addition, the plant hormone abscisic acid 12 has been detected as an endogenous constituent of human brain,18 while caffeine 13 was isolated from a marine gorgonian (Paramuricea chamaelon)19 and the atisane diterpenoid serofendic acid 14, an inhibitor of the oxidant-induced mitochondrial death pathway and putative activator of mitoK(ATP) channels, has been characterised from foetal calf serum.20... 

Ryania is made from the ground roots of the tropical shrub Ryania speciosa. The active principle of ryania is the alkaloid ryanodine (C25H35NOu). Ryania is used for controlling aphids, cabbage loopers, Colorado potato beetles, diamondback moths, cucumber beetles, leafhoppers, corn earworms, European corn borers, codling moths, citrus thrips, and so on. Its oral LD30 in rats is 1200 mg/kg so it is practically nontoxic to mammals. 

---