A New Lycopodine Alkaloid from <i>Huperzia Serrata</i>

Shan, Wei Guang; Ren, Fengyun; Ying, You‐Min; Tong, Cui-Ping; Zhan, Zha‐Jun

doi:10.3184/174751912x13249872110014

Cited by 8 publications

(3 citation statements)

References 9 publications

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“…It is a traditional Chinese medicine to treat strain, contusion, schizophrenia, swelling, and myasthenia gravis [8] . Phytochemical and biological investigations disclosed that LAs were the main bioactive components of this plant [9–15] . Especially, huperzine A, a typical member of LAs, [16–18] is an efficient AChE inhibitor for the treatment of Alzheimer's disease in China [8,19] .…”

Section: Introductionmentioning

confidence: 99%

“…[8] Phytochemical and biological investigations disclosed that LAs were the main bioactive components of this plant. [9][10][11][12][13][14][15] Especially, huperzine A, a typical member of LAs, [16][17][18] is an efficient AChE inhibitor for the treatment of Alzheimer's disease in China. [8,19] With the aim for discovering structurally interesting and bioactive LAs, [20,21] a pair of 12-membered macrocyclic alkaloids, huperserratines A and B, were isolated from this plant in 2020.…”

Section: Introductionmentioning

confidence: 99%

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Hupertimines A–E, Fawcettimine‐Type Lycopodium Alkaloids from Huperzia serrata

Deng

Liu

Zhu

et al. 2022

Chemistry & Biodiversity

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Five new fawcettimine‐type Lycopodium alkaloids, hupertimines A–E (1–5), were discovered from the whole plant of Huperzia serrata, along with two known alkaloids, 8α‐hydroxyphlegmariurine B (6) and 8β‐hydroxyphlegmariurine B (7). The structures of 1–7 were identified through HR‐MS, IR, 1H, 13C, and 2D NMR, and single‐crystal X‐ray diffraction analysis. Structurally, compound 1 was the fourth example of Lycopodium alkaloid with an ether linkage between C‐5 and C‐13 and 2 was the third example of Lycopodium alkaloid with a 5/5/5/5/6 pentacyclic ring system and featuring a 1‐aza‐7‐oxabicyclo[2.2.1]heptane unit. Compounds 1–7 were tested for their BACE1 inhibitory activity. In addition, the correct 1H‐ and 13C‐NMR data for 7 were reported in current study.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Hupertimines A–E, Fawcettimine‐Type Lycopodium Alkaloids from Huperzia serrata

Deng

Liu

Zhu

et al. 2022

Chemistry & Biodiversity

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“…Tremulane sesquiterpenes are a class of natural products which were first isolated from the aspen tree rotting fungus Phellinus tremulae 14 and more recently from cultures of the basidiomycete Conocybe siliginea, 13,15,16 Phellinus igniarius, 17 Marasmius cladophyllus 18 , Ceriporia alachuana, 19 in addition to our previous reports. 6,7 To the best of our knowledge, ceriponol P (1) is the first example of monocyclic tremulane sesquiterpene.…”

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Ceriponol P, the First Example of Monocyclic Tremulane Sesquiterpene Produced by Ceriporia Lacerate a Fungal Endophyte of Huperzia Serrata

Ying

Tong

Wang

et al. 2014

Journal of Chemical Research

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A new tremulane sesquiterpene, ceriponol P, has been isolated from the cultures of Ceriporia lacerate, together with three known metabolites 3-indolecarbaldehyde, 3-methyl-2-indolinone, and daucosterol. Its structure was established by detailed analysis of its spectroscopic data, especially 1D, 2D NMR and HR-ESI-MS data. Ceriponol P represents the first example of monocyclic tremulane sesquiterpene. In biological assays, ceriponol P did not exhibit any significant cytotoxicity against HeLa, HepG2, and SGC 7901 cell lines at a concentration of 20 μM. All the known compounds were reported for the first time from the genus Ceriporia.

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The Chemistry and Biology of Lycopodium Alkaloids

Zhang,

Jiang,

Zhao

2024

Chemistry & Biodiversity

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Lycopodium alkaloids (LAs), a class of natural alkaloids have same biogenesis and similar structure characteristics, obtained from Lycopodiales. Which comprises 388 different species and these fascinating organisms have been identified as remnants of prehistoric ferns, with early fossils dating back as far as 300 million years. LAs usually are tricyclic or tetracyclic compounds with C16N or C16N2 skeleton. But then there are also have a few C11N, C15N, C15N2, C22N2, and C27N3 skeleton. LAs have attracted much scientiﬁc attention because of their important biological activities related to acetylcholinesterase and unique structural characteristics. From 1881 to December 2023, there are 593 LAs from 49 species of Lycopodiales have been reported. Because the total amount of LAs is nearly five times that of 1994, the classification and group allocation of some newly isolated LAs is often challenging and not unambiguous by Ayer’s simple classification. This review makes a more systematic and detailed classification for it and provides extensive coverage of naturally occurring LAs discovered from 1881 to December 2023. Until now, there is no comprehensively summary of biological activity of the LAs. This review is the first time covered the biological activity of the all LAs.

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A New Lycopodine Alkaloid from Huperzia Serrata

Cited by 8 publications

References 9 publications

Hupertimines A–E, Fawcettimine‐Type Lycopodium Alkaloids from Huperzia serrata

Hupertimines A–E, Fawcettimine‐Type Lycopodium Alkaloids from Huperzia serrata

Ceriponol P, the First Example of Monocyclic Tremulane Sesquiterpene Produced by Ceriporia Lacerate a Fungal Endophyte of Huperzia Serrata

The Chemistry and Biology of Lycopodium Alkaloids

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