Two New Nitrone Alkaloids from <i>Huperzia serrata</i>

Li, Yiming; Jiang, Shidong; Zhu, Da‐Yuan

doi:10.1002/hlca.200890110

Cited by 21 publications

(14 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In addition, the single bond between the N atom and C-13 can be broken to yield derivatives with nine-membered heterocyclic rings such as lycoposerramines A, B and T (Takayama et al 2001;Katakawa et al 2005Katakawa et al , 2009. A variety of phlegmarine-type alkaloids have been isolated from H. serrata, including N-oxides such as huperzines J-N, lycoposerramines X-Z, and huperserramine A (Gao et al 2000a(Gao et al , 2008aKatakawa et al 2006;Ying et al 2014). Derivatives featuring a single bond between C-4 and C-12 of the phlegmarine skeleton have also been identified; this modification introduces a new five-membered ring and is observed in phlegmarine alkaloids from H. serrata such as lycoposerramine R and huperzimine (Katakawa et al 2009;Yu et al 2014).…”

Section: Fawcettimine Alkaloidsmentioning

confidence: 99%

Phytochemicals from fern species: potential for medicine applications

et al. 2017

View full text Add to dashboard Cite

Ferns are an important phytogenetic bridge between lower and higher plants. Historically they have been used in many ways by humans, including as ornamental plants, domestic utensils, foods, and in handicrafts. In addition, they have found uses as medicinal herbs. Ferns produce a wide array of secondary metabolites endowed with different bioactivities that could potentially be useful in the treatment of many diseases. However, there is currently relatively little information in the literature on the phytochemicals present in ferns and their pharmacological applications, and the most recent review of the literature on the occurrence, chemotaxonomy and physiological activity of fern secondary metabolites was published over 20 years ago, by Soeder (Bot Rev 51:442–536, 1985). Here, we provide an updated review of this field, covering recent findings concerning the bioactive phytochemicals and pharmacology of fern species

show abstract

Section: Fawcettimine Alkaloidsmentioning

confidence: 99%

Phytochemicals from fern species: potential for medicine applications

et al. 2017

View full text Add to dashboard Cite

show abstract

“…The dried whole grass has been extensively used as a traditional Chinese medicinal (TCM) herb, named Qian Ceng Ta , to cure fever, contusions, strains, hematuria, schizophrenia, and snakebite for several hundreds of years in China [ 7 , 8 , 9 , 10 , 11 , 12 ]. Modern pharmacological studies have shown that the described medicinal properties of Qian Ceng Ta are mainly due to the anticholinesterase activity and anti-inflammatory activity of Lycopodium -like alkaloids in H. serrata [ 13 , 14 , 15 ]. Therefore, H. serrata has become a standout natural resource to explore new drugs to treat cardiovascular diseases and neuromuscular system disease.…”

Section: Introductionmentioning

confidence: 99%

Endophytic Fungal Community of Huperzia serrata: Diversity and Relevance to the Production of Huperzine A by the Plant Host

et al. 2021

View full text Add to dashboard Cite

As the population ages globally, there seem to be more people with Alzheimer’s disease. Unfortunately, there is currently no specific treatment for the disease. At present, Huperzine A (HupA) is one of the best drugs used for the treatment of Alzheimer’s disease and has been used in clinical trials for several years in China. HupA was first separated from Huperzia serrata, a traditional medicinal herb that is used to cure fever, contusions, strains, hematuria, schizophrenia, and snakebite for several hundreds of years in China, and has been confirmed to have acetylcholinesterase inhibitory activity. With the very slow growth of H. serrata, resources are becoming too scarce to meet the need for clinical treatment. Some endophytic fungal strains that produce HupA were isolated from H. serrate in previous studies. In this article, the diversity of the endophytic fungal community within H. serrata was observed and the relevance to the production of HupA by the host plant was further analyzed. A total of 1167 strains were obtained from the leaves of H. serrata followed by the stems (1045) and roots (824). The richness as well as diversity of endophytic fungi within the leaf and stem were higher than in the root. The endophytic fungal community was similar within stems as well as in leaves at all taxonomic levels. The 11 genera (Derxomyces, Lophiostoma, Cyphellophora, Devriesia, Serendipita, Kurtzmanomyces, Mycosphaerella, Conoideocrella, Brevicellicium, Piskurozyma, and Trichomerium) were positively correlated with HupA content. The correlation index of Derxomyces with HupA contents displayed the highest value (CI = 0.92), whereas Trichomerium showed the lowest value (CI = 0.02). Through electrospray ionization mass spectrometry (ESI-MS), it was confirmed that the HS7-1 strain could produce HupA and the total alkaloid concentration was 3.7 ug/g. This study will enable us to screen and isolate the strain that can produce HupA and to figure out the correlation between endophytic fungal diversity with HupA content in different plant organs. This can provide new insights into the screening of strains that can produce HupA more effectively.

show abstract

“…Lycoposerramine-Z ( 1 ) is a representative alkaloid with a cis -fused decahydroquinoline core in this family, and it was first synthesized by the Takayama group and then was achieved by Bradshaw and co-workers . The unusual nitrone moiety of lycoposerramine-Z was postulated to act as a radical trap halting destructive cascades initiated by free radicals and, hence, shows potential application in neurodegenerative diseases . On the basis of our previous work in this family of alkaloids, we wish to report a new enantioselective total synthesis of lycoposerramine-Z ( 1 ) applying a newly developed chiral phosphoric acid catalyzed intramolecular Michael addition.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Total Synthesis of Lycoposerramine-Z Using Chiral Phosphoric Acid Catalyzed Intramolecular Michael Addition

et al. 2016

View full text Add to dashboard Cite

A new enantioselective total synthesis of phlegmarine-type Lycopodium alkaloid lycoposerramine-Z (1) has been accomplished, using one-pot chemoselective sequential additions of two different Grignard reagents to the bis-Weinreb-amide intermediate and an efficient construction of the fully fuctionalized cyclohexanone intermediate with a chiral phosphoric acid catalyzed enantioselective intramolecular Michael addition.

show abstract

Two New Nitrone Alkaloids from Huperzia serrata

Cited by 21 publications

References 7 publications

Phytochemicals from fern species: potential for medicine applications

Phytochemicals from fern species: potential for medicine applications

Endophytic Fungal Community of Huperzia serrata: Diversity and Relevance to the Production of Huperzine A by the Plant Host

Enantioselective Total Synthesis of Lycoposerramine-Z Using Chiral Phosphoric Acid Catalyzed Intramolecular Michael Addition

Contact Info

Product

Resources

About