Phalaris , indole alkaloids

Audette, R.C.S. etal. 1970, Phytochcmical investigation of Manitoba plants, i. A new indole alkaloid and associated alkaloids from Phalaris arundinacea Canadian Journal of Chemistry 149—155. 

Phalarine (244) (Scheme 44), an indole alkaloid with a novel furanobisindole structure, was isolated from blue canary grass Phalaris coerulescens by Colegate and coworkers in 1999 [93]. Recently, Danishefsky and coworkers reported the first synthesis of this indole alkaloid through a novel rearrangement from azaspiroindo-lenine (derived from 246) to precursor 245 [94, 95] (Scheme 44). 

In two studies, several species of Phalaris (canary grass) were found to contain high levels of tryptamine-type indole alkaloids (101, 102). These alkaloids are apparently produced in endophyte-free tissues, and Corcuera... 

The introduction of some new species of grasses into North America and Australia caused losses in animals. The grass species involved were Phalaris tuberosa and P. arundinacea, both accumulating indole derivatives. P. tuberosa contains predominantly A,A-dimethyltryptamine, 5-methoxy-Ar,AT-dimethyltryptamine, and bufotenine, while P. arundinacea contains mainly gramine and hordenine. The tall fescue, Festuca arundinacea, introduced mostly into Missouri, the Dakotas, and Minnesota has other types of alkaloids, loline and perloline. Although the level of these... 

Phalaris tuberosus.- This species, which contains W,iV-dimethyl-tryptamine and 5-methoxy-ff,ff-dimethyltryptamine as its main alkaloids, served as a source of two ff-methyltransferases which catalyzed the transfer of a methyl group from 5-adenosyl-L-methionine to tryptamine and 5-methoxytryptamine °. These enzymes also catalyzed the methylation of other indole-ethylamines... 

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