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Biosynthetic Studies on Mescaline and Related Cactus Alkaloids'

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Biosynthetic Studies on Mescaline and Related Cactus Alkaloids' .icu: rtuum. tniecicu 5, 275-J02 (1971) Biosynthetic studies on mescaline and related cactus alkaloids' JAN LUNDSTRoM Ttepurlmeni of Pharmacognosy, Formaceuiiska Fakulieten, Box 680'1, S-11386 Stockholm In this survey, the following papers will be discussed and will be referred to by the Roman numerals given in the following list. Some unpublished results are also presented. L J. Lundstrom and S. Agurell. Thin-layer chromatography of the peyote alkaloids. Journal of Chromatography 30, 271 (1967). II. J. Lundstrom and S. Agurcll. Gas chromatography of peyote alkaloids.A new peyote alkaloid. Journal of Chromatography 36, 105 (1968). Ill. J. Lundstrom and S, Agurell. Synthesis of specifically labelled substituted .8-phenethylamines, Acta Pluirm. Suecica 7,247 (1970), IV, S. Agurell, J. Lundstrom and F. Sandberg.Biosynthesis of mescaline in peyote, Tetrahedron Letlers 2433 (1967). V, J. Lundstrom and S. Agurell, Biosynthesis of mescaline and anhalamine in peyote. Tetrahedron Letters 4437 (1958). VI. S, Agurcll and J, Lundstrom, Apparent intermediates in the biosynthesis of mescaline and related tetrahvdroisoquinolines. Chemical Communica- tions 1638 (1968), 1 Inaugural dissertation. 275 / I J. LUNDSTRo?rf YII. S. Agurell, J. Lundstrom and A. Masoud. Cactaceae alkaloids VII. Alkaloids of Ecliinocereus merkeri. Journal of Pharmaceutical Sciences 58, 1413 (1969). YIII. J. Lundstrom and S. Agurell. Biosynthesis of mescaline and other peyote alkaloids. Abh. d. Deutsch.Akad, Wissenschaften (Berlin). In press. IX. J. Lundstrom and S. Agurell. A complete hiosynthctic sequence from tyrosine to mescaline in two cactus species. Tetrahedron Letters 3371 (1969) . X. J. Lundstrom. Biosynthesis of mescaline and 3,4-dimethoxyphenethyl- amine in Trichocereus pacliatioi Br&R .. 4cia Pharm. Suecica 7, 651 (1970). XI. J. E. Lindgren, S. Agurell, J. Lundstrom and U. Svensson.Detection of bio- chemical intermediates by mass fragmentography: Mescaline and tetra- hydroisoquinoline precursors. Febs Letters. 13, 21 (1971). XII. S.Agurell, J. G. Bruhn, J. Lundstrom and U. Svensson. Cactus alkaloids X: Alkaloids of TricJwcereus species and some other cacti. Lloydia. In press. XIII. J. Lundstrom. Biosynthesis of mescaline and tetrahydroisoquinoline alkaloids in Lopho pliora urilliamsii (Lem.) Coult. Occurrence and bio- synthesis of catecholamine precursors. Acla Chern, Scand. In press. XIV. J. Lundstrom and S. Agurell. Biosynthesis of mescaline and tetrahydro- isoquinoline alkaloids in Lophophora williamsii (Lem.) Coult. Acta Pharm. Suecica 8,261 (1971). XV. J. Lundstrom. Biosynthesis of tetrahydroisoquinoline alkaloids in Lopho- phora uiilliamsii (Lern.)Coult. Acta Pharm. Suecica. In press. XVI. J. Lundstrom. Identification of new peyote alkaloids.Isomers of the main phenolic thetrahvdroisoquinoliues. Submitted to .4cla Cheiu,Scand. Mescaline represents one of the earliest known hallucinogenic substances, the structure of which was determined as 3,4,5-trimethoxyphenethyl- amine more than 50 years ago [1 J. The hallucinatory properties of mesca- line combined with the observation of the similarities of its structure to physiologically active catecholamines e.g. adrenaline, dopa and dopamine have attracted the interest of a large number of scientists [cf. 2, 3J. Adre- naline, noradrenaline and dopamine are all substances that seem to be intimately involved in the function of the brain and it seemed logical to relate the action of mescaline to these substances. The hallucinatory 276 I l'H6sYN'fHEtfC STUDIES ON MESCALINE AND RELATED CACTUS ALI,ALOIDS OH HO~COOH HO~ HO~ HOV ~H2 HOV ~H2 HOV ~HCH3 MESCALI NE DOPA COPAMI NE ADRENALINE effects of mescaline resemble in some respect symtorns of various mental disturbances and, in fact, it has been suggested that compounds similar to mescaline or mescaline itself could be formed in the body by an erroneous catecholamine metabolism, thus producing an endogenous psychosis. In the hope of finding the cause and maybe even the cure for various mental illnesses, much research work has been performed on mescaline, including its psychopharmacological effects, its metabolism in the animal body and its use for the production of "model psychoses". Recent reviews covering these fields are given by Hoffer and Osmond [2] and Patel [3]. During the preparation of this manuscript, a review by Kapadia and Fayez [4 J on peyote constituents appeared, covering also biological effects of mescaline and similar substances. The earliest and most well-known source of mescaline is the peyote cactus, Lopho phora williamsii (Lem.) Coulter, used from time imme- morial by Indian tribes in the southern parts of USA and in northern Mexico [5, 6].Besides mescaline, the peyote cactus produces a range of tetrahydroisoquinoline alkaloids exemplified by anhalamine, pellotine, lophophorine and anhalinine (see also p. 282) l7]. LOPHOPHORINE ANHALAMINE ANHALININE PELLOTINE A second source of mescaline was found in the huge column cactus Triclioceretis pachanoi Britton & Rose [8], used by Indians in Peru in their preparation of "cimora", a hallucinogenic drink [6, 9].Mescaline has also recently been found in several other Tricliocereus species [XII, 10,11] . Although considerable information was available at the commencement of this work concerning the metabolism of mescaline and similar sub- stances in animal tissues, little was known about the formation and meta- bolism in the plant [3J. It has long been a matter of general agreement that alkaloids like these arise in nature from amino acid precursors such as phenylalanine and tyrosine [12]. More detailed investigation of the biosynthesis of mescaline and similar compounds in their parent plants was desired, for the aforementioned reasons, in order to obtain a broader understanding of hallucinogenic substances. Furthermore, detailed in- 277 I J. LU~DSTRinI formation concerning the biochemical reactions leading from primary metabolites, e.g. tyrosine, to mescaline and to its related compounds, would be of importance for an understanding of secondary metabolism in plants. The alkaloids produced by cacti showing a range of structural varieties within limited frameworks appeared suitable for biosynthetic experiments. Scope of the present investigation "Then this work was initiated, it was known from Leete's early experi- ments [13 J that tyrosine could be converted to mescaline in peyote. A few types of biochemical reactions seemed to be involved in the trans- formation of tyrosine to mescaline: decarboxylation, hydroxylation of the aromatic nucleus and O-methylations. Enzymes from both animal and plant origin which catalyze these types of reactions are known. We decided to investigate rigorously the sequence of ordcr, if any, for these biochemical transformations occurring in the conversion of tyro- sine to mescaline. It was also our intention to investigate thc biosynthesis of the tetrahydroisoquinoline alkaloids of peyote and especially to study the extent to which the biosynthesis of mescaline and these structurally related compounds were linked by common pathways, For the accurate determination of hiosynthetic pathways, compounds, postulated as precursors and intermediates on account of incorporation experiments using radioactive tracers, should also be identified as natu- rally occurring metabolites.In performing this research, sensitive methods such as gas chromatography and gas chromatography-mass spectrometry (GLC-MS) were used and several compounds fitting in the hiosynthetic schemes were identified as occurring naturally in cacti. To broaden our experience in the biosynthesis of mescaline, parallel studies were performcd in the two mescaline producing cacti L urilliamsii and T. pachanoi, Thus, according to our results, and results meanwhile obtained inde- pendently by other groups, Leete [Ll, 15], Paul et al, [ef. 16],Battersby et al, [17, 18J and Kapadia ei al. [cf. 4, 19], the hiosynthetic sequence in the formation of mescaline and the phenethylarnine portion of thc tetrahydroisoquinoline alkaloids of peyote, is one of the most complete sequences in alkaloid biosynthesis known today. In addition to L. uiilliamsi and T. pachanoi, the alkaloid contents of several Trichocereus species were examined and mescaline was found in some of these. Also, some other cacti were investigated and many alka- loidal compounds, previously unknown from cacti or other plants, were identified and valuable information regarding the biosvnthetic work was gained. Chromatographic methods (TLC, GLC) of great importance for further work are mainly described in papers I and II. 278 r BIOSY::\THETICSTUDIES 0::\ MESCALI::\E AND RELATED CACTUS ALKALOIDS Methods for the synthesis of labelled compounds are mainly described in paper III. Some additional syntheses of doubly labelled compounds are presented in paper XV. Results on the biosynthesis of mescaline are presented in the papers IY, V, VIII-X and XIII, XIV. The biosynthesis of 3,1~-dimethoxyphenethyl- amine is treated in paper X. Biosynthesis of the phenethylamine portion of the tetralujdroisoquitioline alkaloids is described in papers V, VIII, IX and XIII-XV. Some results on the ring closing units (C-l and C-l + C-9) in the tetrolnjtiroiscquinoline biosuniliesis are presented in papers V and XY. Intermediates of the biosijnihetic pathways, identified by GLC-MS or in "trapping experiments" are discussed in papers ·VI, XIV and XV. The use of the sensitive and very selective analytical method called mass [raqmentoorcphu, in the search for intermediates of biosynthetic routes
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