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N-Methylsecoglaucine, a New Phenanthrene Alkaloid from Fumariaceae

1990; Elsevier BV; Volume: 31; Issue: 6 Linguagem: Inglês

10.3987/com-90-5356

1881-0942

Luís Castedo, Olga María Blanco, Magdalena Cid, Julio A. Seijas, M. Carmen Villaverde,

Plant and fungal interactions

The isolation and its total synthesis of the new phenanthrene alkaloid&methylsecoglaucine (1) from Placycapnos spicata are reponed.The phenanthrene alkaloids are a group of optically inactive bases probably derived biogenetically by Hofmann elimination in aporphine salts.They can therefore be included among the isoquinoline alkaloids.1 More than 30 phenanthrene alkaloids have been isolated from natural sources, moa as secondary or teniary amines bur some as quaternary salts and N-oxides?They occur in several plan: families, 3 though as far as we know there is only one previous repon of their occurrence in Fumariaceae.As part of our continuing research on the alkaloid content of Iberian Fumariaceae we have determined and repon here the alkaloid content of Platycapnos spicaia .This work included the isolation and total synthesis of the new phenanthrene alkaloid N-methylsecoglaucine (1).5 Platycapnos spicala collected in the surroundings of Madrid was extracred with methanol and thz methanolic extract was subjected to standard acid-base fractionation to afford 1.63 % of crude dichloromethane soluble alkaloid P x r a r !whkh 1 -?Z!' h,eL' :s bc formed mainly of the apol~hine alkaloids glaucine (2j and nantenine (3).Chromatography of this exhact separated the known alkaloids glaucine (2), nantenine (3).dehydronantenine (41, dehydroglaucine (51, 0-methylatheroline (6).oxonantenine (71, domesticine (S), N-methyllaurotetanine (9), corunnine (10).thalictuberine (11) and the new phenanthrene alkaloid N-methylsecoglaucine (1).Apan from the major aporphines glaucine (2) and nantenine (3), the alkaloid content of Platycapnos spicara is thus mainly formed of biogenetically related alkaloids such as the corresponding oxoaporphines and dehydroaporphines, and the phenanthrenes N-methylsecoglaucine (1) and thalictuberine (11).