Ormosia Alkaloids

These alkaloids have been exhaustively examined only recently although their existence has been known for some 50 years 118). They occur along with other lupine alkaloids in Ormosia species. Their structures are known for the greater part although none has been synthesized. 

Three well-defined alkaloids have been isolated from O. panamensis Benth. ormosinine, C20H33N3 (mp 220° [a],49 +9.0°) panamine, C20H33N3 (mp 36°-40° -11°) and ormosanine, C20H35N3 (mp 

The original investigation of 0. dasycarpa Jacks. (118) reported the presence of ormosine and ormosinine but a later investigation (123) failed to confirm these findings. In addition to —)-sparteine two new alkaloids were reported dasycarpine, C20H35N3 (tripicrate, mp 152° perchlorate, mp 240°) and alkaloid-I, C20H37O3N3 (mp 207°  

A more recent examination of P. nanus revealed the presence of a new base, piptanthine, C20H35N3 (mp 143°) (124). Piptanthine (CLVIII) reacts with formaldehyde to form homopiptanthine (CLXI) (mp 189°) which suffers hydrolysis to its progenition on acid treatment. With phosgene, or less satisfactorily with ethyl chloroformate, in the presence of triethylamine there is formed homoxypiptanthine (CLX) (mp 155°). Lithium aluminum hydride reduction of the latter gives homopiptanthine. 

Ormosanine (CLV) and formaldehyde condense to Jamine (CLVI), C21H35N3 (mp 154°), (125) the structure of which was determined by 

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Treatment of (144) with Na2C03 in aqueous MeOH gave the ketoaldehyde (145)48), which possessed the Ormosia alkaloid skeleton. 

The Lupinine-Lupanine-Sparteine-Matrine Group and the Ormosia Alkaloids... 

Specific experiments to demonstrate the biogenesis of the Ormosia alkaloids have not been reported although the involvement of 4 moles of lysine (below) would seem probable (37). Of interest is the copresence of... 

Russian studies of the stereochemistry of alkaloids of the matrine group by X-ray analysis have been extended to cis-matrine (20), sophoridine N-oxide (21), " and lehmannine N-oxide (22). The stereochemical complexity of some Ormosia alkaloids was discussed last year (c. Vol. 12, p.76-77). Now the alkaloid sweetinine, first obtained from Sweetia panamensis, has been isolated from S. 

Full details have appeared of the determination by X-ray analysis of the absolute configuration of the Ormosia alkaloid, podopetaline (see Vol. 4, p. 114). ... 

Valenta and Liu have given an account of the structure and synthesis of Ormosia alkaloids, and a review of the Nuphar alkaloids has been published. Carbon-13 n.m.r. and mass spectroscopy of quinoiizidine alkaloids have been reviewed. 

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