Cassain

All the erythrophleum alkaloids examined in detail so far are of the same type, viz., acyl esters of either monomethylaminoethanol, e.g., erythrophleine and coumingidine or dimethylaminoethanol, such as cassaine or cassaidine. The acyl substituents are complex, yield 1 7 8-trimethylphenanthrene on selenium dehydrogenation, and contain at least one hydroxyl group, which may be acylated by an aliphatic acid, e.g., coumingine forms three components on hydrolysis. 

Cassaine, C34HJ9O4N. This alkaloid was first isolated by Dalma and was further examined by Faltis and Holzinger. According to Dalma it is... 

Cassaine Cassia carnaval, Erythrophleum Na+, K+-ATPase [anaesthetic,... 

Cells carefully control the homeostasis of their ion concentrations by the action of ion channels (Na, K , Ca " channels) and throu Na, K -ATPase and Ca -ATPase. These channels and pumps are involved in signal transduction, active transport processes, and neuronal and neuromuscular signaling. Inhibition of transport processes (ion channels, carriers) is achieved by (Table IV) acronycine, ervatamine, harmaline, quinine, reserpine, colchicine, nitidine, salsolinol, sanguinarine, stepholidine, caffeine, sparteine, monocrotaline, steroidal alkaloids, aconitine, capsaicine, cassaine, maitoxin, ochratoxin, palytoxin, pumiliotoxin, saxitoxin, sole-nopsine, and tetrodotoxin. 

DE 019 bucillamine, deacetyllanatoside C deslanoside, deanol [ban] (norcholine N-dimethylethanolamine) is isolated from a Neurospora crassa strain and is a residue present in the alkaloids cassaine and cassaidine. It is a choline precursor and has been used to enhance central acetylcholine formation. It has been used as a CNS STIMULANT (nootropic agent) to enhance mental function, and as an ANTIDEPRESSANT,... 

Cardiac glycosides found in plants, some insects and in the skin of toads (Bufonidae) are potent and well-known inhibitors of Na+/K+-ATPase. Also few alkaloids, such as harmaline, nitidine, sanguinarine, capsaicine, cassaine, and solenopsine (from ants) exhibit Na+/K+-ATPase inhibition, which interferes with the maintainance of the membrane potential and secondary active transport systems. 

There followed a rapid succession of reports of the isolation and characterization of alkaloids Schlittler (13) described the secondary coumingidine from E. couminga Ruzicka, Plattner, and Engel (14) isolated coumingine and a new tertiary base, which was also found in E. guineense along with a second tertiary base by Engel and Tondeur (15) Paris (16) isolated cassaine from an unknown but botanically described Erythrophleum from Indo-China. 

Cassaine, C24H39O4N, crystallizes from ether in glossy flakes, belonging to the rhombic system. It melts at 142.5° and has [a] —113° (ethanol) and [a] —117° (iV/10 hydrochloric acid) (10). 

Cassaine is a tertiary base that can be satisfactorily titrated with methyl red, bromophenol green, or iodoeosin as indicators it gives a yellow-colored solution in sulfuric acid which in the presence of vanadium pentoxide becomes green. The bisulfate, B H2SO4 2H2O, melts with decomposition at 290° and the hydrochloride, B-HC1-H20, melts at 212-213° (17). 

The presence of a hydroxyl and a carbonyl in cassaine are proved by the formation of a basic monoacetyl derivative (m.p. 123-124°) and of an oxime (m.p. 123-125°). The two remaining oxygen atoms are accounted for by an ester linkage which is hydrolyzed by acids as follows ... 

The absorption spectra of cassaic acid and of cassaine show that the double bond which is shown to be present by the ready reduction of the alkaloid to dihydrocassaine (m.p. 115-116°) [a]n 0° in ethanol, —6.5° in A /10 hydrochloric acid) is a,fi- to the carboxyl rather than to the carbonyl. Dihydrocassaic acid melts at 253-255° and has [a] 0° (ethanol), — 5° (A /IO sodium hydroxide). 

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