Abstract
BackgroundSince long back, several plants species belonging to family Lycopodiaceae or Huperziaceae are being traditionally used in treatment of diseases like Alzheimer’s disease and myasthenia gravis. In 1986, huperzine A, structurally lycodine type of alkaloid was isolated and established as potent acetylcholine esterase inhibitor. Hence, further, in pursuit of similar compounds, several hundreds of different types of lycopodium alkaloids have been isolated from different Lycopodiaceae or Huperziaceae plants species.Main bodyFor few of these recently isolated alkaloids, the possible mechanisms of their biosynthesis have been proposed while few of them were tried for their laboratory total asymmetric synthesis. This review summarized lycodine-type Lycopodium alkaloids, whose isolation, biosynthesis, and total synthesis have been reported after 2000. It also includes structure–activity relationship.Short conclusionMore than 40 lycodine-type alkaloids have been isolated and structurally elucidated since 2000. Their biosynthetic pathway suggested that they got biosynthesized from lysine, while structure–activity relationship established the structural requirement of lycodine-type alkaloids to possess potent acetylcholine esterase inhibitory activity.
Highlights
Biological significance and need of isolation of new Lycopodium alkaloids Since long back, several traditional Chinese medicinal plants of family Lycopodiaceae and Huperziaceaeare being used in treatment of sprains, strains and myasthenia [12]
Short conclusion: More than 40 lycodine-type alkaloids have been isolated and structurally elucidated since 2000. Their biosynthetic pathway suggested that they got biosynthesized from lysine, while structure–activity relationship established the structural requirement of lycodine-type alkaloids to possess potent acetylcholine esterase inhibitory activity
It was observed that a polycyclic carbon skeleton with different levels of oxidation is the common feature in all Lycopodium alkaloids, posing the challenging target for total synthesis [33,34,35]
Summary
Lycopodium alkaloids with unique heterocyclic frameworks of different types like C11N, C15N, C16N, C16N2, C22N2, or C27N3 have gained enormous research interest with focus on their biogenesis [1,2,3] and biological activities [4]. As per Ayer et al 1991, lycopodium alkaloids are of four types: lycodine-type, lycopodane-type, fawcettimine-type, and miscellaneous-type [5]. In 1938, Achmatowicz and Uzieblo again isolated lycopodine with correct molecular formula, and two new nitrogencontaining compounds [7]. As per our literature survey, since 2000, only few (14 out of 500+) species of plants belonging to family either lycopodiaceae or huperziaceae have been processed for isolation of active lycodine type of lycopodium alkaloid
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