Abstract
Five novel isoquinoline alkaloids (+)-N-(methoxylcarbonyl)-N-nordicentrin (1), (+)-N-(methoxylcarbonyl)-N-norpredicentrine (2), (+)-N-(methoxylcarbonyl)-N-norbulbodione (3), and (+)-N-(methoxylcarbonyl)-N-norisocorydione (4), and (+)-8-methoxyisolaurenine-N-oxide (5) were isolated, together with one known compound, (+)-N-(methoxylcarbonyl)-N-norglaucine (6), from a 70% EtOH extract of the barks of Litsea cubeba. Structural elucidation of all the compounds were performed by spectral methods such as 1D- and 2D-NMR, IR, UV, and HRESIMS. Alkaloids 1, 2 and 6 showed antimicrobial activity against the bacterium S. aureus and two fungi (A. alternata and C. nicotianae). Compounds 3,4 exhibited significant cytotoxicity against all of six tested tumor cell lines.
Highlights
Litsea cubeba (Lauraceae ) is a 3- to 10 m evergreen tree or shrub widely distributed in Southeastern
The bark of L. cubeba has been used in oriental traditional medicine for the treatment of atopic eczema and coronary heart disease, and its Molecules 2012, 17 antioxidant activities and antimicrobial activities against Staphylococcus aureus, Salmonella typhi, and Pseudomonas aeruginosa have been reported [5,6,7]
Medium used in the antimicrobial activity included nutrient agar medium (S. aureus), Dorset egg medium (M. tuberculosis) and Sabouraud dextrose broth (SDB) agar medium
Summary
Litsea cubeba (Lauraceae ) is a 3- to 10 m evergreen tree or shrub widely distributed in Southeastern. L. cubeba can be used as a flavoring or herbal medicine. The bark of L. cubeba has been used in oriental traditional medicine for the treatment of atopic eczema and coronary heart disease, and its Molecules 2012, 17 antioxidant activities and antimicrobial activities against Staphylococcus aureus, Salmonella typhi, and Pseudomonas aeruginosa have been reported [5,6,7]. Litebamine and its N-homologues possess acetylcholinesterase activity [13]. Chromatographic separation of an aqueous EtOH extract of the barks of L. cubeba has yielded five novel isoquinoline alkaloids, namely (+)-N-(methoxylcarbonyl)-N-nordicentrin (1), (+)-N-(methoxycarbonyl)-N-norpredicentrine (2), (+)-N-(methoxyl-carbonyl)-N-norbulbodione (3), and (+)-N-(methoxycarbonyl)-N-norisocorydione (4), and (+)-8-methoxyl-isolaurenine N-oxide (5), and one known compound,. Their structures were established on the basis of their chromatographic properties, chemical and physicochemical methods. All the triterpenoids were evaluated for their in vitro antibacterial, antifungal and cytotoxic properties
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