Hypepontine, a new quaternary alkaloid with antimicrobial properties.

New isoquinoline alkaloid hypepontine (1) together with a five known compounds, were identified in Hypecoum ponticum Velen, the partial synonym of Hypecoum procumbens L. The structure of the new substance was elucidated based on spectroscopic evidence. The tertiary and quaternary alkaloid mixtures as well as the isolated alkaloids were evaluated for their antibacterial and antifungal activity. The result revealed that the crude alkaloid mixture containing quaternary isoquinoline alkaloids showed potent antifungal and antibacterial activity.

Alkaloids of Seeds, in vitro Cultivated, and ex vitro Adapted Plants of the Bulgarian Endemic Species Papaver degenii (Papaveraceae).

Papaver degenii (Urum. & Jav.) Kuzmanov is a Bulgarian endemic and glacial relict growing in the alpine zone of Pirin Mountains and it is included in the Red Data Book of Bulgaria. Numerous plants were in vitro multiplied in order to study the alkaloid composition of the species and to test the potential for green biotechnology establishment. Percentages of the crude alkaloid mixture in dried in vitro shoots and ex vitro adapted plants to room phytoiron were similar to that in seeds (0.49%) and 5 to 6 times higher than in the aerial parts of wild-growing plants. Amurensine was the only alkaloid detected in the seeds. Four isoquinoline alkaloids were isolated from the regenerated plants, belonging to two alkaloid types: isopavines (amurensine and Ο-methylthalisopavine) and protopines (allocryptopine and protopine), amurensine being the main alkaloid: 63.4% in in vitro shoots, up to 88.1% in the aerial parts of ex vitro adapted plants. Allocryptopine was in higher amount (30%) in the roots of the ex vitro adapted plants.

Comparative Study of Alkaloid Pattern of Four Bulgarian Fumaria species.

The alkaloid pattern of four Fumaria species (Fumaria kralikii, Fumaria rostellata, Fumaria schleicherii, Fumaria thureii) growing in Bulgaria was investigated by GC-MS and twenty isoquinoline alkaloids were determined. Phytochemical investigation of the alkaloid composition on Fumaria thuretii Boiss was made for the first time. The alkaloid profile of the species was compared at two levels, between different species and within two species from different habitats. Two chemotypical groups, based on the types of isoquinoline alkaloids were suggested. To group A belong species F. kralikii, F. rostellata (F. r. 1) and F. thuretii containing more than 50% spirobenzylisoquinoline alkaloids of the crude alkaloid mixtures. To group B belong species F. rostellata (F. r. 2) and F. schleicherii containing more than 40% protopine alkaloids and relatively high percentage phthaldeisoquinoline alkaloids (11-19%). In group A phthaldeisoquinoline alkaloids were not detected.