D-Isoboldine

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[edit] Description

The aporphine alkaloid isoboldine has been isolated from opium. It has been identified by NMR and mass spectrometry and by comparison of its infrared spectrum with that of synthetic (±)-isoboldine. ORD measurements have shown that the isolated alkaloid has the absolute configuration corresponding to the (S)-series.

The anti microbial activity of isobolidine against a series of bacteria and fungi was evaluvated via in vitro screening. The alkaloid failed to demonstrate any inhibitory activity against the growth the growth of bacteria but was strongly inhibitory to the growth of superficial fungus Tricophyton rubrum. The alkaloid exhibited only waek inhibition of the growth of the superficial fungus Microsporum gyspseum. The in vitro antimicrobial activity of isoboldine was investegated by agar diffusion and dilution methods against various gram positive and gram negative bacteria as well as acid fast organism Mycobacterium pheli and the yeast Candida albicans. Isoboldine exhibited no significant avtivity against any of the test organisms. Isoboldine was evaluated for its in vitro antimicrobial activity against a variety of microorganisms. The alkaloid was found to be inactive against gram positive and gram negative bacteria as wall as an acid fast bacillus and a yeast.The oxoderivatives of aporphine were more active against granm positive bacteria than the reduced aporphins, but the former had a lower activity against yeast and no activity against gram negative bacteria.

Isoboldine was determined to inhibit rabit lens aldose reductase(IC50 2.7X10-4M).

[edit] General Properties

*Molecular Weight

327.37434

*Molecular Formula

C₁₉H₂₁NO₄

*IUPAC NAME

N/A

*Canonical Smiles

CN1CCC2=CC(=C(C3=C2C1CC4=CC(=C(C=C43)OC)O)O)OC

*Isomeric Smiles

N/A

*XLogP

2.1

*Topological Polar Surface Area

62.2

[edit] External Links

• Pubchem

Link to BIAdb Database