Alkaloids isolation

Figure 9 3-Alkylpiperidine alkaloids isolated from sponges in the order Haplosclerida...

Narcotoline, This alkaloid, isolated from opium-poppy... 

Adlumine and Adlumidine. (Items 1, 21, 24, 25, 29 list, p. 169). From Adlumia cirrhosa Rap. Schlotterbeck isolated two alkaloids, adlumine, C3,H3 09N(0H)(0Me)2, m.p. 188, [ ]d + 39-88°, and adlumidine, C30H29O9N, m.p. 234°. Manske used these two names for alkaloids isolated from A. fungosa Greene, stated to be identical with A. cirrhosa Rap., and suggested (I) that Schlotterbeck s adlumine was probably bicuculline with some adlumine and (II) that the two adlumidines are identical. 

This alkaloid, isolated by Faltis (1912, ef. Scholtz, 1913), was first assigned... 

There are also on record a number of other observations regarding S. American plants believed to be associated with this drug, e.g., Freise has given preliminary descriptions of alkaloids isolated from the following species —... 

Tazettine, CuHjiOsN. This alkaloid isolated by Spath and Kahovee, has m.p. 210-1° vac.), + 150-4° (CHClg) and yields an 0-aeet ... 

Strychnicine. This alkaloid, isolated from nux-vomica leaves grown in. lava, forms needles, m.p. 240° dec.), and is characterised by the following colour reaction. When sodium hydroxide solution is added drop by drop to a solution of a salt of the alkaloid in water, the precipitate formed dissolves on addition of more alkali, forming an orange-coloured liquid which develops a violet colour on addition of hydrochloric acid. Strychnicine is scarcely poisonous, but is said to produce tetanus in frogs. 

Villalstonine, C40HgjO4N4. This alkaloid, isolated by Sharp, is a eolourless granular powder, sintering at 218° and melting at 260° it yields well-crystallised salts. The hydrochloride, B. 2HC1.4H2O, forms colourless needles, m.p. 270° dec., [ ]d + 56-3° (HgO) the hydrobromide. 

VsUlago maydis. Alkaloids isolated from this maize fungus were named ustilaginine and ustilagotoxine and are stated to resemble ergotinine and ergo-toxine respectively. (Mas, Bol. Soc. Quim. Peru, 1938, 4, 3.)... 

Evodiamine, the alkaloid from the Chinese drug plant Evodia rutaecarpa Benth. and Hook., has also been called rhetsine and its oxidation product rhetsinine, which is also found in nature, was shown to be the diamide (53). Recently a hypotensive red alkaloid isolated from the Brazilian plant Hortia arborea Engl, was given the name hortiamine. Degradation and synthetic studies have shown it to possess the structure (55). It was found together with another... 

Antitumor compounds, among them cyclic peptides, terpenoids, and alkaloids isolated from higher plants 99YZ529. 

Heteronuclear two-dimensional /-resolved spectra contain the chemical shift information of one nuclear species (e.g., C) along one axis, and its coupling information with another type of nucleus (say, H) along the other axis. 2D /-resolved spectra are therefore often referred to as /,8-spectra. The heteronuclear 2D /-resolved spectrum of stricticine, a new alkaloid isolated by one of the authors from Rhazya stricta, is shown in Fig. 5.1. On the extreme left is the broadband H-decoupled C-NMR spectrum, in the center is the 2D /-resolved spectrum recorded as a stacked plot, and on the right is the con tour plot, the most common way to present such spectra. The multiplicity of each carbon can be seen clearly in the contour plot. 

Figure 5.49 shows the four HOHAHA spectra obtained at 20, 40, 60, and 100 ms of hyocyamine, an alkaloid isolated from Datura fastusa. The various short-range and long-range homonuclear connectivities established on the basis of HOHAHA spectra of hyoscyamine provided a powerful tool for structure elucidation. The spectrum obtained with a mixing time of... 

Figure 5.50 (A) ID H-NMR spectrum of hyoscyamine, an alkaloid isolated from Datura fastusa. (B) HOHAHA spectra of the same compound recorded at 20, 60, and 100 ms. The projection spectra are taken at (a) 8 1.30, (b) 8 3.50, and (c) 8 5.16.

Figure 8.1 H-NMR spectrum and substructures of 3a-hydroxylupanine, an alkaloid isolated from I ontice leontopetalum. The fragments, I, II, and III are labeled with the alphabetic assignment of every proton or set of close-lying protons.

Marine sponges are a source of an array of polycyclic diamine alkaloids of common biogenetic origin. This class of secondary metabolites has been the subject of four previous reviews [4-7]. Therefore, the present review will include literature reports previously not discussed, dealing with the isolation, structure determination, biological activities, and total synthesis of polycycUc diamine alkaloids isolated from marine sponges. This review will not include guanidine alkaloids [8,9] or the manzamine alkaloids [10,11], since these compounds have been recently reviewed elsewhere. Only polycycUc... 

Andersen RJ, van Soest RWM, Kong F (1996) 3-Alkylpiperidine alkaloids isolated from marine sponges in the order Haplosclerida. In Alkaloids chemical and biological perspectives. Pergamon, New York, p 301... 

Entries 5 to 8 are synthetic applications in more complex molecules. Entries 5 and 6 illustrate the diphenylphosphoroyl azide method. Entry 7 was used in the late stages of the synthesis of an antitumor macrolide, zampanolide, to introduce the amino group. The ultimate target molecule in Entry 8 is himandrine, one of several polycyclic alkaloids isolated from an ancient plant species. 

It is noteworthy that gelsenicine is the most toxic alkaloid isolated so far from G. elegans. The LD50 value is 185 /ig/kg for mice on intraperitoneal injection. 

During the period 1976-1986, biosynthetic studies on hasubanan alkaloids were carried out by Battersby et al. (81-84) for hasubanonine (5) together with protostephanine (57). The two alkaloids, isolated from Stephania japonica, arise from the same precursor, and their unusual structures are of biosynthetic interest, namely, the vicinally trioxygenated ring C in 5 and the unique natural example of a dibenz d,f ] azonine skeleton in 57. 

---