Isolation of a new lycodine alkaloid from <i>Lycopodium japonicum</i>

Wu, Ji‐Chun; Wang, Huanqin; Ma, Yangmin; Jiang, Jingjing; Zhan, Rui; Chen, Ye‐Gao

doi:10.1080/14786419.2014.984184

Cited by 9 publications

(5 citation statements)

References 7 publications

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“…(18 S )‐Hydroxypropyllycodine ( 5 ) and (18 S )‐ N ‐methylhydroxypropyllycodine ( 6 ) possess the molecular formula C 19 H 28 N 2 O and C 20 H 30 N 2 O, respectively, obtained from the HR‐ESI‐MS data. Analysis of the 1D NMR data and HSQC spectrum of 5 & 6 (Table 2) resolved identical structures respective to hydroxypropyllycodine [23] and N ‐methylhydroxypropyllycodine [23] . Conclusion of the above was confirmed by the 1 H− 1 H COSY and HMBC data (Figure 2).…”

Section: Resultssupporting

confidence: 52%

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Lycopodium Alkaloids from Huperzia serrata and Their Anti‐acetylcholinesterase Activities

Zhu

Shen

et al. 2023

Chemistry & Biodiversity

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One new fawcettimine‐type alkaloid (1), one new miscellaneous‐type alkaloid (2), four new lycodine‐type alkaloids (3–6), and eight known ones (7–14) were isolated from the whole plants of Huperzia serrata. Their structures and absolute configurations were elucidated based on spectroscopic data, X‐ray diffraction, ECD calculation and Mosher's method. Compound 1 was a rare C18N2‐type Lycopodium alkaloid, possessing serratinine skeleton with an amide side chain in C‐5. The absolute configuration of the 18‐OH of compounds 4–6 were first determined by Mosher's method. Moreover, compounds 1–14 were assayed anti‐acetylcholinesterase effect in vitro, and compound 7 showed significant anti‐acetylcholinesterase activity with an IC50 value of 16.18±1.64 μM.

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Section: Resultssupporting

confidence: 52%

“…(18S)-Hydroxypropyllycodine 2) resolved identical structures respective to hydroxypropyllycodine [23] and N-methylhydroxypropyllycodine. [23] Conclusion of the above was confirmed by the 1 HÀ 1 H COSY and HMBC data (Figure 2). Meanwhile, we obtained the crystal of 6 and determined its relative configuration (Figure 4).…”

Section: Resultsmentioning

confidence: 84%

Lycopodium Alkaloids from Huperzia serrata and Their Anti‐acetylcholinesterase Activities

Zhu

Shen

et al. 2023

Chemistry & Biodiversity

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“…To date, researchers have only used conventional methods to obtain the bioactive alkaloids of Lycopodiaceae and Amaryllidaceae. However, a number of papers have been published using different organic solvents such as methanol, ethanol, hexane, chloroform and many others at various concentrations [14,15]. The application of these solvents has led to the isolation of alkaloids and confirmation of many of their properties, including anti-AChE activity.…”

Section: Methods Of Isolationmentioning

confidence: 99%

Methods of isolation and bioactivity of alkaloids obtained from selected species belonging to the Amaryllidaceae and Lycopodiaceae families

Dymek

Mroczek

2021

Current Issues in Pharmacy and Medical Sciences

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Alkaloids obtained from plants belonging to the Amaryllidaceae and Lycopodiaceae families are of great interest due to their numerous properties. They play a very important role mainly due to their strong antioxidant, anxiolytic and anticholinesterase activities. The bioactive compounds obtained from these two families, especially galanthamine and huperzine A, have found application in the treatment of the common and incurable dementia-like Alzheimer’s disease. Thanks to this discovery, there has been a breakthrough in its treatment by significantly improving the patient’s quality of life and slowing down disease symptoms – albeit with no chance of a complete cure. Therefore, a continuous search for new compounds with potent anti-AChE activity is needed in modern medicine. In obtaining new therapeutic bioactive phytochemicals from plant material, the isolation process and its efficiency are crucial. Many techniques are known for isolating bioactive compounds and determining their amounts in complex samples. The most commonly utilized methods are extraction using different variants of organic solvents allied with chromatographic and spectrometric techniques. Optimization of these methods and modification of their procedures potentially allows researchers to obtain the expected results. The aim of this paper is to present known techniques for the isolation of alkaloids, especially from three species Narcissus, Lycopodium and Huperzia that are a rich source of AChE inhibitors. In addition, innovative combinations of chromatographic and spectrometric methods and novel TLC-bioautography will be presented to enable researchers to better study the bioactivity of alkaloids.

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“…Huperzine A has a high potential for the treatment of Alzheimer Disease (AD) [2][3][4][5]. Another prominent species is Lycopodium clavatum in which many high potency alkaloids have been found, to name a few: Hupezine E, α-Onocerin, α-obscurine, des-N-methyl-α-obscurine,… [6,7].…”

Section: Introduction *mentioning

confidence: 99%

“…Chuong et al has found a new alkaloid: lycosquarosine A in Vietnamese sourced Huperzia squarrosa [11]. Lycopodium japonicum, a species common in Japan and China, has a unique structure alkaloid group named lycojaponicumins [12], in 2015 another alkaloid: N-methylhydroxypropyllycodine was discovered [7]. Lycopodium clavatum is one of the most widespread species in the family Lycopodiaceae and abundantly found in various area.…”

Section: Introduction *mentioning

confidence: 99%

The Toxicity Evaluation of Lycopodiacea Extracts by Mice Neural Cell and Zebrafish Embryo

Kien¹,

Trang²,

Thanh³

et al. 2021

NST

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Many species in the family Lycopodiacea possess highly potential medical substances, notably are Huperzine A of Huperzia serrata and alkaloids isolated from Lycopodium clavatum(α-Onocerin , Lycopodine,..). Various members of this family are found throughout of Vietnam and a few researches on its diversity as well as alkaloid isolation has been conducted, however, there is a lack of toxicology studies on this subject. In this study, three crude extracts (labeled AI.1, AI.2 and AI.3), which come from Lycopodium sp.collected from 3 different regions of Vietnam, have been tested on 2 toxicological models: primary neural cells derived from Swiss white mouse (in vitro) and Zebrafish (Danio rerio) embryos (in vivo). Our results show that the all three extracts are relatively low in toxicity, IC50 value on primary neural cell ranging from 800 - 1100 mg/L, while LC50 of fish embryos at 100 - 300 mg/L. AI.2 has the least effect of viability of both cells and embryos compare to the others. This data give the prove showed that the safety using Lycopodium as tradional medicine.

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Isolation of a new lycodine alkaloid from Lycopodium japonicum

Cited by 9 publications

References 7 publications

Lycopodium Alkaloids from Huperzia serrata and Their Anti‐acetylcholinesterase Activities

Lycopodium Alkaloids from Huperzia serrata and Their Anti‐acetylcholinesterase Activities

Methods of isolation and bioactivity of alkaloids obtained from selected species belonging to the Amaryllidaceae and Lycopodiaceae families

The Toxicity Evaluation of Lycopodiacea Extracts by Mice Neural Cell and Zebrafish Embryo

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