Three Lycopodium alkaloids from Thai club mosses

Nilsu, Thanasan; Thaisaeng, Wachirasak; Thamnarak, Wanlaya; Eurtivong, Chatchakorn; Jumraksa, Apiwan; Thorroad, Sakornrat; Khunnawutmanotham, Nisachon; Ruchirawat, Somsak; Thasana, Nopporn

doi:10.1016/j.phytochem.2018.09.001

Cited by 15 publications

(15 citation statements)

References 23 publications

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“…Lycosquarrines A–E ( 1 – 5 ), each possessing a β-oriented hydrogen at C-4, represent new examples of uncommon 4-epilycopodine-type alkaloids. Only four such compounds have been reported, namely, lycopodatine C, 4-epilycopodine, and phlenumdines A and B . In addition, compound 19 , previously obtained by acid methanolysis of phlenumdine A, was isolated in the present study as a natural product for the first time.…”

Section: Results and Discussionmentioning

confidence: 99%

“…In addition, compound 19 , previously obtained by acid methanolysis of phlenumdine A, was isolated in the present study as a natural product for the first time. Biosynthetically, 1 – 5 and 19 could be traced back to 4-epilycopodine, which was possibly generated from lycopodine during keto–enol tautomerization between C-4 and C-5 . As outlined in Scheme , 4-epilycopodine could be converted to intermediate A via dehydrogenation and reduction; subsequently, either oxygenation at C-8 would produce 19 or epoxidation of the Δ 11(12) double bond would yield intermediate B .…”

Section: Results and Discussionmentioning

confidence: 99%

“…Löve & D. Löve (Huperziaceae) is an epiphytic clubmoss mainly distributed in Southeast Asia, Oceania, and Southwest China that can be found on trees and rocks in lowland to mid-altitude forests . The first study on the alkaloidal constituents of this plant was reported in 2011; since then, dozens of Lycopodium alkaloids with diverse structures have been isolated. − As part of our ongoing search for structurally intriguing and biologically significant alkaloids, , the aerial parts of P. squarrosus collected from Guangxi Zhuang Autonomous Region of China were studied. This investigation led to the isolation of 18 new Lycopodium alkaloids, namely, eight lycopodine-type ( 1 – 8 ), seven lycodine-type ( 9 – 15 ), two fawcettimine-type ( 16 and 17 ), and a miscellaneous alkaloid ( 18 ), as well as eight known alkaloids.…”

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Lycosquarrines A–R, Lycopodium Alkaloids from Phlegmariurus squarrosus

et al. 2020

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Eighteen new Lycopodium alkaloids, lycosquarrines A−R (1−18), and eight known alkaloids were isolated from the aerial parts of Phlegmariurus squarrosus. Compounds 1−5 and 19, identified from natural sources for the first time, are uncommon lycopodine-type alkaloids with β-oriented H-4. Pentacyclic 4 and 5 represent the first examples of 5,12-and 5,11-epoxy Lycopodium alkaloids, respectively, and an epoxide-opening cyclization reaction is suggested to be a key step in their biosynthesis. Compound 18 possesses the same carbon skeleton as carinatine A ( 22), which was previously reported as a unique Lycopodium alkaloid with a 5/ 6/6/6 ring system. X-ray crystallographic data analysis was used to determine the absolute configuration of 18, leading to the establishment of the absolute configuration of 22 by comparison of the ECD spectra. An anti-acetylcholinesterase activity assay showed that 11 and 20 exhibited inhibitory activities with IC 50 values of 4.2 and 2.1 μM, respectively.

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Section: Results and Discussionmentioning

confidence: 99%

Section: Results and Discussionmentioning

confidence: 99%

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Lycosquarrines A–R, Lycopodium Alkaloids from Phlegmariurus squarrosus

et al. 2020

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“…Approximately 276 species have been identifiedin this family, they distributed sporadically around the world and differ greatly between region [8,9]. A research on 11 species native to Panama has found that most of them differ in AChEI potency with 2 plants: Huperzia chamaeleon and Huperzia reflexa show high AChEI and antioxidant properties [10].…”

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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“…13 Accepted: 2020-05 -29 2020SciPress Ltd, Switzerland Online: 2020 H. squarrosa is known as a highly valuable medicinal plant, which contains alkaloids, flavones, triterpenes, phenolic acids, especially including Huperzine A (Hup A), Huperzine B (Hup B), N-methyl-huperzine B, Huperzinine, Lycoporine A, Carina-tumine A, etc [5]. To the best of our knowledge, over 300 Lycopodium alkaloids have been reported [6]. According to the report of Ngoc et al [7], the alkaloids isolated from H. squarrosa collected from Lam Dong province -Vietnam includes 6 main compounds: lycosquarosine A, acetylaposerratinine, huperzine A, huperzine B, 8α-hydrophlemariurine B and huperzinine which may account for the effectiveness of this plant in the treatment of several brain diseases [8].…”

Section: Introductionmentioning

confidence: 99%

Evaluation of Genetic Diversity and Identification of <i>Huperzia</i> Species Collected in Some Different Areas in Vietnam by Molecular Markers

Hà

Khanh

Trung

2020

ILNS

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The objective of this study was to evaluate genetic diversity of 35 Huperzia samples collected from the different ecological areas in Vietnam by using rbcL markers. The results revealed that the samples were genetically diverse in high genetic similarity which ranged from 98.0 to 99.0%, respectively. Based on the Genbank data in comparison, it was ascertained that only one sample (BK3) is a member of H.phlegmarioides group, and others belonged H. squarrosa group as divided into two main groups by phylogenetic tree analyses. It suggests that some Huperzia samples may plausibly descend from the same origin, evolution and arising relations. This study has provided useful information for further identifying the high-quality genetic plant sources for propagation, development and conservation of the high-valued medicinal materials of Huperzia plants in this country.

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Three Lycopodium alkaloids from Thai club mosses

Cited by 15 publications

References 23 publications

Lycosquarrines A–R, Lycopodium Alkaloids from Phlegmariurus squarrosus

Lycosquarrines A–R, Lycopodium Alkaloids from Phlegmariurus squarrosus

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

Evaluation of Genetic Diversity and Identification of <i>Huperzia</i> Species Collected in Some Different Areas in Vietnam by Molecular Markers

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