Alkaloids Simple Indoles

Senecio alkaloids, see Pyrrolizidine alkaloids Simple indole alkaloids, 10, 491 (1967)... 

L-tryptophan Indole alkaloids Indole Simple indole Arundacine... 

This structural group of indole alkaloids covers simple indole alkaloids (e.g., tryptamine, serotonin, psilocin and psilocybin), /3-carboline alkaloids (e.g., harmine), terpenoid indole (e.g., ajmalicine, catharanthine and tabersonine), quinoline alkaloids (e.g., quinine, quinidine and cinchonidine), pyrroloindole... 

The a for structural development of serotonin (simple indole alkaloid) is L-tryptophan, and the j3 is 5-hydroxy-L-tryptophan (Figure 64). Serotonin is a monoamine. It is a hioactive alkaloid known as a neurotransmitter. It has been found in the cardiovascular system, in Wood cells and the peripheral and CNS. 

Figure 64. Structural development of simple indole alkaloids.

Hibino, S. and Choshi, T. 2001. Simple indole alkaloids and those with a nonrear-ranged monoterpenoid unit. Nature Product Reports, 18 66-87. 

Simple indole alkaloids 8, 111, 112, 113 Simple phenylamine alkaloids 110 Simple tetrahydroisoquinoline alkaloids 7,... 

A. Simple indoles, carbazoles, carbolines, and physostygmine type alkaloids 106... 

Somei, M., and Yamada,F. (2003). Simple indole alkaloids and those with nonarranged monoterpenoid unit. Nat. Prod. Rep. 20,171-211. 

The simple indole alkaloids harman (27) and harmine (28) are also susceptible to biotransformation. Polystictus versicolor metabolizes both 27 and 28 to unidentified products, formed in a yield of 50% in the case of 28 (42). Mammalian liver preparations perform an oxidative O-demethylation of harmine (28) to produce harmol (29) (45). The supernatant fraction from the lO.OOOg centrifugation of liver homogenates of cow, mouse, rabbit, guinea pig, rat, and cat were all effective in O-demethylation, the highest yields (90%) being obtained after incubation for 30 min with the preparations from cow and mouse liver (45). No other products were detected from the biotransformation of harmine by the liver preparations mentioned above,... 

Gercideae. (a) The occurrence of alkaloids. Key to branches leading to families that accumulate quinolizidines, pyrrolizidines (No. 1 see arrows) Erythrina (No. 3) indolizidines (No. 4) p-carbolines (No. 5) or simple indoles (No. 2) are marked. The rbcl sequences used (1400 bp) derived from Kass and Wink, 1997a,b Wink and Mohamed (2003). Trees were reconstructed with maximum parsimony. 

The indole group of compounds is conveniently divided into the so-called simple indole derivatives and the indole alkaloids, which often have complicated stmctures, and indole dyes. Thus it was demonstrated that not all compounds are completely separated by either the basic eluent, methyl acetate-isopropanol-25% ammonia (45 35 20, v/v), or the acidic eluent, chloroform-96% acetic acid (95 5, v/v). Therefore one combines the effects of both of these eluent systems in the 2-D TLC method in this way, 14 simple indole derivatives and anthranilic acid can be separated. Compounds are separated into groups according to their polarities. ... 

Several of the alkaloids from bryozoans can be considered to be indoles—Amathla alternata and Zoobotryon vertlcillatum contain simple indoles while Chartella papyracea, Flustra foliacea and Hinckstnojlus-tra denticulata give rise to more complex polycyclic compounds. 

Chapter 17. Terpenoid indole alkaloids and simple indole alkaloids. . . 155... 

TERPENOID INDOLE ALKALOIDS AND SIMPLE INDOLE ALKALOIDS... 

EXPERIMENTAL CONDITIONS USED FOR GAS CHROMATOGRAPHY OF TERPENOID INDOLE ALKALOIDS AND SIMPLE INDOLE ALKALOIDS... 

Several investigators have developed the reductive cyclization of o-nitrostyrenes into an efficient synthesis of indoles. Thus, research by the groups of Watanabe [480], Soderberg [481], and Cenini [482] have established this reductive Pd-catalyzed TV-het-eroannulation reaction as a viable and powerful route to simple indoles and fused indoles (411) as shown below. In addition, Soderberg has shown the application of this method to carbazolones [481d], natural p-carbolines [481e], and the carbazole alkaloid murrayaquinone A [48If]. Ohta described the related Pd-catalyzed cyclization of o-aminophenethyl alcohol to indole in 78% yield [483]. 

Simple indole and oxindole alkaloids and Iryptamine oligomers... 

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