Amaryllidaceae and Sceletium alkaloids

Abstract

Covering: July 2010 to June 2012. Previous review: Nat. Prod. Rep., 2011, 28, 1126-1142. Recent progress on the isolation, identification, biological activity and synthetic studies of structurally diverse alkaloids from plants of the family Amaryllidaceae is summarized in this review. In addition, the structurally related alkaloids isolated from Sceletium species are discussed as well.

Antiproliferative activities of Amaryllidaceae alkaloids from Lycoris radiata targeting DNA topoisomerase I

“…Homolycorine, which also belonged to the lycorenine type, showed promising antiproliferative activities against HeLa (human cervical adenocarcinoma), Vero (monkey kidney epithelium) and Jurakat (human T-cell leukemia) cell lines39. Galanthamine and lycoramine were also reported to exhibit acetylcholineaterase (ACHE) inhibitory activity and neuroprotective effect for the treatment of Alzheimer’s disease140. It is well known that many AAs isolated from Amaryllidaceae plants, such as narciprimine, arolycoricidine and distichamine, are the important secondary metabolites used for the treatment of cancer.…”

“…Statistically, more than 500 different kinds of Amaryllidaceae alkaloids (AAs) have been isolated from the medicinal plants of the family Amaryllidaceae123. Owing to the diverse pharmacological activities, such as anticancer, antimalaria, antifungal, neuroprotective effects, acetylcholinesterase and butyrylcholinesterase-inhibitory activity4567, these alkaloids have attracted a great deal of attentions in modern medical societies.…”

The Amaryllidaceae alkaloids: biosynthesis and methods for enzyme discovery

“…Purchasing the substrate is frequently not an option for highly specialized pathway intermediates, so the latter two alternatives become necessary. In the case of Amaryllidaceae alkaloids, there is a large diversity of specialized synthesis methods that have regularly been reviewed by Zhong Jin and can be used for production of various pathway intermediates (Jin, 2013). As biosynthetic genes are discovered, functional expression of these genes in a heterologous system will facilitate chemo-enzymatic syntheses (Augustin et al, 2015).…”

“…Some noteworthy exceptions are the collection of alkaloids that have been found in the genus Hosta that is in the order Asparagales along with Amaryllidaceae (Chase et al, 2009; Li et al, 2012), the potential but un-replicated isolation of acetylcaranine and lycorine from Urginea altissima which is also a member of the order Aspergales (Miyakado et al, 1975; Pohl et al, 2001), and the isolation of crinamine from Dioscorea dregeana (Mulholland et al, 2002). New Amaryllidaceae alkaloid structures and the biosynthesis of these alkaloids have recently been reviewed (Kornienko and Evidente, 2008; Bastida et al, 2011; Jin, 2013; Takos and Rook, 2013). Galanthamine is a prime example of the Amaryllidaceae alkaloids.…”

“…The three common phenol-phenol’ coupling reactions that follow require the same biochemistry to operate and are likely catalyzed by cytochrome P450 enzymes, laccases, or peroxidases (Schlauer et al, 1998; Ikezawa et al, 2003; Ono et al, 2006; Díaz Chávez et al, 2011; Constantin et al, 2012). The extensive work studying the biosynthesis of the derivatives generated from phenol-phenol’ coupling products has been reviewed recently and is beyond the scope of this review (Kornienko and Evidente, 2008; Bastida et al, 2011; Jin, 2013; Takos and Rook, 2013). …”