Recent progress in chemistry and bioactivity of monoterpenoid indole alkaloids from the genus gelsemium : a comprehensive review

Abstract

Monoterpenoid indole alkaloids (MIAs) represent a major class of active ingredients from the plants of the genus Gelsemium . Gelsemium MIAs with diverse chemical structures can be divided into six categories: gelsedine-, gelsemine-, humantenine-, koumine-, sarpagine- and yohimbane-type. Additionally, gelsemium MIAs exert a wide range of bioactivities, including anti-tumour, immunosuppression, anti-anxiety, analgesia, and so on. Owing to their fascinating structures and potent pharmaceutical properties, these gelsemium MIAs arouse significant organic chemists’ interest to design state-of-the-art synthetic strategies for their total synthesis. In this review, we comprehensively summarised recently reported novel gelsemium MIAs, potential pharmacological activities of some active molecules, and total synthetic strategies covering the period from 2013 to 2022. It is expected that this study may open the window to timely illuminate and guide further study and development of gelsemium MIAs and their derivatives in clinical practice.

Aza-Achmatowicz rearrangement coupled with intermolecular aza-Friedel–Crafts enables total syntheses of uleine and aspidosperma alkaloids

“…3000 members) with diverse biological activities and intricate skeletal diversity. 1–7 They continue to influence the research fields of natural products, drug discovery, biochemistry, and especially organic chemistry (total synthesis and methodology development). 8,9 Structurally, the direct covalent C3–C2′ linkage of indole (in blue) with piperidine (in red) characterizes this subclass of alkaloids and thus has sparked great interest from generations of organic chemists in developing novel and efficient synthetic strategies 10–40 (Scheme 1c).…”

Molecular Pharmacology of Gelsemium Alkaloids on Inhibitory Receptors

“…Several studies have characterized the phytochemical profile of Gelsemium plants [ 2 , 3 , 4 ]. These reports describe the species as a rich source of natural compounds, including iridoids, coumarins, steroids, and alkaloids.…”

“…Studies using purified indole alkaloids have shown many biological effects in both in vitro and in vivo assays [ 2 , 3 , 4 ]. These actions range from antitumor activity to antioxidant and anti-inflammatory effects [ 2 , 4 , 5 ].…”

The antianxiety effects of koumine and gelsemine, two main active components in the traditional Chinese herbal medicine Gelsemium: A comprehensive review

“…More than 120 alkaloid compounds have been successfully obtained and determined from the stems, leaves, and roots of plants in the genus Gelsemium , of which more than 80 are indole and hydroxyindole alkaloids [14‐17] . Gelsemium monoterpenoid indole alkaloids are classified into six classes based on their chemical structures: gelsedine, gelsemine, humantenine, koumine, sarpagine, and yohimbane [18] . Among them, koumine is a monoterpene indole alkaloid with the highest content among Gelsemium alkaloid monomers, followed by gelsemine [19] .…”

“…[14][15][16][17] Gelsemium monoterpenoid indole alkaloids are classified into six classes based on their chemical structures: gelsedine, gelsemine, humantenine, koumine, sarpagine, and yohimbane. [18] Among them, koumine is a monoterpene indole alkaloid with the highest content among Gelsemium alkaloid monomers, followed by gelsemine. [19] These two alkaloids are rapidly absorbed and eliminated, can penetrate the blood-brain barrier, and are widely distributed in all tissues, including the brain.…”