Covering: 2017 to 2023 (now) Amaryllidaceae alkaloids (AAs) are a unique class of specialized metabolites containing heterocyclic nitrogen bridging that play a distinct role in higher plants. Irrespective of their diverse structures, most AAs are biosynthesized via intramolecular oxidative coupling. The complex organization of biosynthetic pathways is constantly enlightened by new insights owing to the advancement of natural product chemistry, synthetic organic chemistry, biochemistry, systems and synthetic biology tools and applications. These promote novel compound identification, trace-level metabolite quantification, synthesis, and characterization of enzymes engaged in AA catalysis, enabling the recognition of biosynthetic pathways. A complete understanding of the pathway benefits biotechnological applications in the long run. This review emphasizes the structural diversity of the AA specialized metabolites involved in biogenesis although the process is not entirely defined yet. Moreover, this work underscores the pivotal role of synthetic and enantioselective studies in justifying biosynthetic conclusions. Their prospective candidacy as lead constituents for antiviral drug discovery has also been established. However, a complete understanding of the pathway requires further interdisciplinary efforts in which antiviral studies address the structure–activity relationship. This review presents current knowledge on the topic.

Amaryllidaceae alkaloid (AA) biosynthesis has garnered significant attention in recent years, particularly with the commercialization of galanthamine as a treatment for the symptoms of Alzheimer’s disease. A significant amount of research work over the last eight decades has focused on the understanding of AA biosynthesis, starting from early radiolabelling studies to recent multi-omics analysis with modern biotechnological advancements. Those studies enabled the identification of hundreds of metabolites, the characterization of biochemical pathways, and an understanding of the environmental stimuli and of the molecular regulation of these pharmaceutically and agriculturally important metabolites. Despite numerous studies, there remain significant gaps in understanding the biosynthesis of AAs in Amaryllidaceae plants. As such, further research is needed to fully elucidate the metabolic pathways and facilitate their production. This review aims to provide a comprehensive summary of the current state of knowledge on AA biosynthesis, from elicitation of expression of transcription factors in the cell nucleus to alkaloid transport in the apoplast, and to highlight the challenges that need to be overcome for further advancement.

Amaryllidaceae alkaloids are a diverse group of alkaloids exclusively reported from the Amaryllidaceae plant family. In planta, their biosynthesis is still not fully characterized; however, a labeling study established 4'-O-methylnorbelladine as the key intermediate compound of the pathway. Previous reports have characterized O-methyltransferases from several Amaryllidaceae species. Nevertheless, the formation of the different O-methylnorbelladine derivatives (3'-O-methylnorbelladine, 4'-O-methylnorbelladine, and 3'4'-O-dimethylnorbelladine), the role, and the preferred substrates of O-methyltransferases are not clearly understood. In this study, we performed the biochemical characterization of an O-methyltransferase candidate from Narcissus papyraceus (NpOMT) in vitro and in vivo, following biotransformation of norbelladine in Nicotiana benthamiana having transient expression of NpOMT. Docking analysis was further used to investigate substrate preferences, as well as key interacting residues of NpOMT. Our study shows that NpOMT methylates norbelladine preferentially at the 4'-OH position in vitro and in planta. Interestingly, NpOMT also catalyzed the synthesis of 3',4'-O-dimethylnorbelladine from norbelladine and 4'-O-methylnorbelladine during in vitro enzymatic assay. Furthermore, we show that NpOMT methylates 3,4-dihydroxybenzylaldehyde and caffeic acid in a nonregiospecific manner to produce meta/para monomethylated products. This study reveals a novel catalytic potential of an Amaryllidaceae O-methyltransferase and its ability to regioselectively methylate norbelladine in the heterologous host N. benthamiana.

Yin, X.-B., Lamara, M., Liyanage, N. S., Zhu, R.-L. & Fenton, N. J. 2021. Riccardia vitrea (Aneuraceae), a liverwort species new to China and North America. – Herzogia 34: 279 –285. The liverwort species Riccardia vitrea Furuki (Aneuraceae) is reported for the first time for China and North America (Canada). This report is primarily focused on its occurrence in Canada.. Riccardia vitrea is characterized by numerous small oil bodies in both epidermal and inner cells, and by prostrate, wide and poorly developed ultimate pinnules, and is thus easily distinguished from other Canadian species of the genus. This constitutes a significant extension of its known range from East Asia to North America. This species could be overlooked owing to the fact that dry specimens without oil bodies are often used in identification, and it is probably more widespread than currently known in the boreal forests of Canada. Illustrations and descriptions based on the Canadian specimens are provided with a key for Canadian species of the genus.