Datura ferox

Atropine and scopolamine, the main toxic alkaloids of Datura stramonium and Datura ferox, were detected and quantified using HPLC-ESl-MS both in Datura seeds and in the gastric content of a man whose death was ascribed to a fatal heart attack [100]. 

Isolated from Datura ferox L. 29), this product was hydrolyzed to (— )-3a,6/S-tropanediol and ( —)-tropic acid. A synthesis of XXI was achieved by hydrogenolytic cleavage (30) of A — )-hyoscine (XXII), obtained by total synthesis, and followed by separation of the diastereo-isomeric S( — )-tropoyltropanediols with dibenzoyltartaric acid. Feeding D. stramonium L. seedlings with hyoscyamine-(methyl-i4C) brought about its conversion to the 6 3-hydroxy derivative-(methyl-i C) 31). 

Tropane alkaloids. It is probable that hyoscyamine-like alkaloids are formed in shoots of Atropa and Datura and in ripening seeds of the latter (246, 267). Grafts of Datura on tomato yielded unidentified alkaloids, and Atropa grafts on tomato yielded ouscohygrine (268). Grafts of Nicotiana tabacum L. on Duboisia myoporoides yielded very little hyoscine or hyosoyamine but some nicotine and nornicotine and more than the normal amount of tropine (269). It was concluded that tropine and scopine are formed in the root and esterified in the leaf. Romeike (270) observed that leaves of Datura ferox L. can transform hyosoyamine into hyoscine. 

L. On partial hydrolysis it yielded meteloidine and tiglic acid hence it is ( )3a,6/S-ditigloyloxy-7jS-hydroxytropane (111). (—)3a,6j3-ditigloyl-oxy-tropane has been isolated from Datura roots (141). A new alkaloid is described from Datura ferox L. (142). 

Torres C, Mimosa M, Galetto L. Nectar ecology of Datura ferox (Solanaceae) An invasive weed with nocturnal flowers in agro-ecosystems from central Argentina. 

Tropane alkaloids are produced in the roots of plants and transported to the aereal portions. In grafting experiments, when aereal portions of Datura ferox, D. stramonium, D. innoxia, and Atropa belladonna were grafted onto roots of Cyphomandra betacea (normally not alkaloid containing), the aereal portions lacked alkaloids. In the reverse situation, aereal portions of C. betacea plants grafted onto roots of the other species contained tropane alkaloids (Waller and Nowacki, 1978). 

Hybrids of Datura ferox [virus susceptible and hyoscine (23) producing] and D. stramonium [virus resistant and hyoscyamine (18) producing] produced vigorous virus-resistant plants that produced hyoscine, an alkaloid important in medicine. The Fi plants inherited the high alkaloid level of D. stramonium, but the oxidative ability of D. ferox. The segregation ratio in the F2 generation is 3 1 and hyoscine production is dominant (Waller and Nowacki, 1978). 

Another, 6,7-disubstituted derivative of hyoscyamine with the proposed structure 7P-hydroxy-6P-propenyloxy-3a-tropoyloxytropane was reported as a minor constituent of the seeds of Datura ferox (Vitale et al. 1995) however, due to the fact that the structure was determined only by GC/MS data the stereochemistry of this compound was not elucidated unequivocally this also implicates that it is not in accordance with the adjustment of Lounasmaa and Tamminen (1993). Thus, it might be alternatively the 6P-hydroxy-7P-acyloxy isomer. By the way, the structural formula given by the authors is in accordance with this alternative if the usual numbering for tropanes would have been chosen by them. 

Rare Derivatives of Scopolamine (Hyoscine) Not Included in Table 3.1. Another 3-acyloxyscopine derivative, 3-phenylacetoxy-6p,7P-epoxytropane was identified in the seeds of Datura ferox (Vitale et al. 1995). It may be assumed that this metabolite is 3a-substituted since only 3a-acyloxy congeners were found in this species and natural 3P-substituted scopines are unknown in general however, the stereochemistry at C-3 has not yet been determined. 

Hartmann et al. 1986), respectively. To date, 3a-phenylacetoxytropane was found again only in transformed root cultures of a Brugmansia Candida x aurea hybrid (Robins et al. 1990) as well as of Hyoscyamus x gyGrjfyi (lonkova et al. 1994), whereas the occurrence of 3a-cinnamoyloxytropane is confined to L pubiflora. A stereochemically not determined 3-phenylacetoxy-6,7-epoxytropane, found in the seeds of Datura ferox, has been mentioned already above (Vitale et al. 1995). 

VauqueUn LN (1809b) Atropa belladonna. Ann Chim 72 53 fide Czapek (1925) p 280 Vitale AA, Acher A, PomiUo AB (1995) Alkaloids of Datura ferox from Argentina. J Ethnopharmacol 49 81-89... 

In 1958 Romeike reported a successful cross between Datura ferox and Datura stramonium, D, ferox is a small, virus-susceptible plant that produces only minute amounts of alkaloids, but its alkaloid is the valuable drug hyoscine. The other parent, a vigorous and non-virus-susceptible plant containing at least ten times as much alkaloid, produces hyoscy-amine, which could not readily be converted to hyoscine chemically. The difference is in the oxidation level, hyoscine being the epoxide of hyoscy-amine. There are at least three reactions necessary to perform the oxidation. The Fi plants inherited the high alkaloid level of Datura stramonium and the oxidation ability of Datura ferox. The yield of alkaloids per plant... 

The scion of Datura ferox transformed hyoscyamine into hyoscine (see Chapter 2, on genetics of tropane alkaloids, p. 69). Since the Datura stramonium scion was not able to transform alkaloids, it accumulated the same type as was produced in the root similarly, the Cyphomandra scion could not effect transformation it accumulated only hyoscyamine. There-... 

A cell suspension culture of Datura ferox, when supplied with dl-[2- C]-ornithine, yielded radioactive putrescine, citrulline, arginosuccinate, arginine, y-aminobutyric acid, glutamic acid, aspartic acid, a-keto-8-guanidovalerate, and a-keto-S-aminovalerate. However, none of the tropane alkaloids produced by this species was radioactive. It was suggested that this in vitro cell culture lacks the enzyme which catalysed the reaction between A -pyrroline-2-carboxylic acid (55) and acetoacetyl coenzyme A. The product of this condensation ultimately yields hygrine (57) and then tropine (56) as illustrated in Scheme 12. 

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