Zur Konstitution des Ammoresinols (XXXI. Mitteil. über natürliche Cumarine)

Peyote Constituents: Chemistry, Biogenesis, and Biological Effects

“…The elucidation of the structure and the synthesis of all these alkaloids had to wait until Spath made his contributions. He published the first of a series of papers on "Anhalonium alkaloids" in 1919 and continued his work up to 1939 (3,(73)(74)(75)(76)(77)(78)(79)(80)(81)(82)(83)(84)(85)(86)(87)(88)(89)(90); his work also included studies on the alkaloids obtained from other Cactaceae. In addition to the previously mentioned alkaloids, Spath isolated from peyote five other products: anhalinine and anhalidine in 1935 (80, 81), N-methylmescaline in 1937 (83), N-acetylmescaline in 1938 (84), and O-methyl-danhalonidine in 1939 (85).…”

Amaryllidaceae alkaloids: Absolute configuration and biological activity

“…Tazettine (50, Figure 7) is one of the most abundant alkaloids of this subgroup of Amaryllidaceae alkaloids 93,115 and its structure was assigned in 1943. 116 Later on, 50 was also isolated from Sprekelia fonnosissima together with haemanthamine (15), haemanthidine (14), and ismine and from Isnaene calithina, together with galanthamine, homolycorine, lycorine (1), and nerinine. 57 The absolute configuration of 50 was assigned by X-ray analysis of its methyl iodide.…”

Ammodoremin, an Epimeric Mixture of Prenylated Chromandiones from Ammoniacum

“…and some related plants from Central Asia and Persia [2], and its medicinal use was already known to the ancients, being documented in the Greek and Latin medical literature [2]. Early studies by Sputh et al [3] and Kunz and Hoops [4] culminated in the structure elucidation of the major phenolic constituent ammoresinol (l), but the interest in Ammoniacum was then scanty [5] [6], even though a recent patent claims antitumor properties for the crude gum resin [7]. We report here the isolation of a mixture of epimeric non-phenolic compounds occurring in Ammoniacum in a concentration comparable to that of 1.Results and Discussion.…”

“…Hexane AcOEt 9: 1 eluted 8.05 g of 2-nor-l,2-secoammoresinol[5] [6], and hexane AcOEt 8:2 gave 28 g (1 1.7%) of a 5:4:1 mixture of 2a/3a/4 as a yellowish gum. Further elution yielded 32 g of crude ammoresinol (l), that was purified using the method of Spiith et al [3].Acetylation of2a/3a/4. A soln.…”