Production of Cholinesterase-Inhibiting Compounds in In Vitro Cultures of Club Mosses

Szypuła, Wojciech J.; Pietrosiuk, Agnieszka

doi:10.1007/978-3-030-11253-0_30-1

Cited by 3 publications

(19 citation statements)

References 164 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Lim et al [22] found HupA in 11 of 17 investigated Huperzia species. Members of the genus Lycopodium L. and Diphasiastrum Holub (Lycopodiaceae sensu stricto), commonly found over large areas in Europe, America and Asia, are rich in a variety of alkaloids, mainly lycopodine and its derivatives [23]. As confirmed by the published studies, only a few members of the Lycopodiaceae family can synthesize HupA and HupB, which is another factor limiting the procurement of the raw plant material for the pharmaceutical industry [23].…”

Section: Introductionmentioning

confidence: 99%

“…With the growing interest in therapeutic applications of HupA, the demand for club mosses as a source of this and other alkaloids which are acetylcholinesterase inhibitors is increasing rapidly and studies on in vitro cultures of Lycopods are gaining in importance. Larger-scale HupA and HupB procurement using tissue culture techniques requires highly efficient and fast plant tissue growth and alkaloid biosynthesis in vitro [23]. Earlier studies [17,19,24] proposed ways to enhance the production of alkaloids and plant tissue in a variety of tissue culture models.…”

Section: Introductionmentioning

confidence: 99%

“…In the present study, we used the cultures Huperzia selago gametophytes for the biosynthesis of HupA and for the first time HupB. H. selago is the only European Huperzia species which contains HupA [5,20,23] (Figure 1). Importantly, H. selago is a rich source of HupA, since its sporophytes contain much more of the alkaloid than found in Huperzia serrata native to Asia [17,20,23].…”

Section: Introductionmentioning

confidence: 99%

“…H. selago is the only European Huperzia species which contains HupA [5,20,23] (Figure 1). Importantly, H. selago is a rich source of HupA, since its sporophytes contain much more of the alkaloid than found in Huperzia serrata native to Asia [17,20,23]. The preliminary studies of HupA production in in vitro culture of H. selago gametophytes indicate that this is a more efficient method of obtaining secondary metabolites than sporophyte culture [17,23,25].…”

Section: Introductionmentioning

confidence: 99%

“…Importantly, H. selago is a rich source of HupA, since its sporophytes contain much more of the alkaloid than found in Huperzia serrata native to Asia [17,20,23]. The preliminary studies of HupA production in in vitro culture of H. selago gametophytes indicate that this is a more efficient method of obtaining secondary metabolites than sporophyte culture [17,23,25]. So far, there have been no studies on the biosynthesis of alkaloids or any other metabolites using in vitro culture of gametophytes (prothallus).…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Huperzine A and Huperzine B Production by Prothallus Cultures of Huperzia selago (L.) Bernh. ex Schrank et Mart

et al. 2020

Self Cite

View full text Add to dashboard Cite

This is the first report of an efficient and effective procedure to optimize the biosynthesis of huperzine A (HupA) and huperzine B (HupB) in vitro from Huperzia selago gametophytes. Axenic tissue cultures were established using spores collected from the sporophytes growing in the wild. The prothalia were obtained after 7–18 months. Approximately 90 up to 100% of the gametophytes were viable and grew rapidly after each transfer on to a fresh medium every 3 months. The best biomass growth index for prothallus calculated on a fresh (FW) and dry weight (DW) basis, at 24 weeks of culture, was 2500% (FW) and 2200% (DW), respectively. The huperzine A content in the gametophytes was very high and ranged from 0.74 mg/g to 4.73 mg/g DW. The highest yield HupA biosynthesis at >4 mg/g DW was observed on W/S medium without growth regulators at 8 to 24 weeks of culture. The highest HupB content ranged from 0.10 mg/g to 0.52 mg/g DW and was obtained on the same medium. The results demonstrate the superiority of H. selago gametophyte cultures, with the level of HupA biosynthesis approximately 42% higher compared to sporophyte cultures and 35-fold higher than when the alkaloid was isolated from H. serrata, its current source for the pharmaceutical industry. Moreover, the biosynthesis of HupB was several-fold more efficient than in H. selago sporophytes growing in the wild. HPLC-HR-MS analyses of the extracts identified eight new alkaloids previously unreported in H. selago: deacetylfawcettine, fawcettimine, 16-hydroxyhuperzine B, deacetyllycoclavine, annopodine, lycopecurine, des-N-methylfastigiatine and flabelline.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Huperzine A and Huperzine B Production by Prothallus Cultures of Huperzia selago (L.) Bernh. ex Schrank et Mart

et al. 2020

Self Cite

View full text Add to dashboard Cite

show abstract

Biological and Ecological Roles of Club Mosses (Lycopodiaceae) Alkaloids

Szypuła,

Pietrosiuk

2023

Reference Series in Phytochemistry

View full text Add to dashboard Cite

Fractionation of Lycopodiaceae Alkaloids and Evaluation of Their Anticholinesterase and Cytotoxic Activities

et al. 2021

View full text Add to dashboard Cite

In view of the abundant evidence that Lycopodiaceae alkaloids, including the well-known huperzine A (HupA), are among the potent acetylcholinesterase (AChE) inhibitors, an attempt was made to search for new compounds responsible for this property. For this purpose, three plant species belonging to the Lycopodiaceae family, commonly found in the Euro-Asia region, were subjected to the isolation of bioactive compounds, their identification and subsequent evaluation of their anticholinesterase and cytotoxic activities. Methanolic extracts of two Lycopodium and one Hupezia species were obtained via optimized pressurized liquid extraction (PLE) and then pre-purified using innovative gradient vacuum liquid chromatography (gVLC). For the first time, three sorbents of different porosity packed in polypropylene cartridges and mobile phase systems of different polarity were used to elute the target compounds. This technique proved to be a rapid tool for the obtainment of alkaloid fractions and allowed one to select the appropriate process conditions to yield potent AChE inhibitors in each of the species studied. More than 100 collected fractions were analyzed via HPLC/ESI-QTOF-MS, which enabled one to detect more than 50 compounds, including several new ones previously unreported. Some of them were present in high purity fractions (60–90% of the established purity). TLC bioautography assays proved that the analyzed species are rich sources of AChE inhibitors, but H. selago showed the highest anti-AChE activity. Additionally, the modified silanized silica gel sorbent used allowed one to isolate L. clavatum alkaloids more efficiently using an aqueous reversed-phase solvent system. Furthermore, the tested extracts from the three plant extracts were found to be safe, as they did not exhibit cytotoxicity to skin fibroblasts.

show abstract

Production of Cholinesterase-Inhibiting Compounds in In Vitro Cultures of Club Mosses

Cited by 3 publications

References 164 publications

Huperzine A and Huperzine B Production by Prothallus Cultures of Huperzia selago (L.) Bernh. ex Schrank et Mart

Huperzine A and Huperzine B Production by Prothallus Cultures of Huperzia selago (L.) Bernh. ex Schrank et Mart

Biological and Ecological Roles of Club Mosses (Lycopodiaceae) Alkaloids

Fractionation of Lycopodiaceae Alkaloids and Evaluation of Their Anticholinesterase and Cytotoxic Activities

Contact Info

Product

Resources

About