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Lyconadins G and H,Two Rare Lyconadin-Type lycopodium alkaloids from lycopodium complanatum

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Natural Products and Bioprospecting 2016年第6期6卷 279-284页

作者： Jin-Tang Cheng Zhi-Jun Zhang Xiao-Nian Li Li-Yan Peng Huai-Rong Luo Xing-De Wu Qin-Shi Zhao State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunming 650201People’s Republic of China Institute of Chinese Materia Medica China Academy of Chinese Medical SciencesBeijing 100700People’s Republic of China

Two rare lyconadin-type lycopodium alkaloids,lyconadins G(1)and H(2),together with four known ones(3–6),were isolated from lycopodium *** structures were determined on the basis of their spectroscopic analyses,and the absolute configuration of 1 was established by an X-ray crystallographic *** is the first time to establish the absolute configuration of lyconadin-type lycopodium alkaloid by an X-ray diffraction *** addition,these findings may provide more information for the biosynthesis of lyconadins.

关键词： lycopodium alkaloids lycopodium complanatum Lyconadin

Lycodine-Type lycopodium alkaloids from the Whole Plants of Huperzia serrata

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Natural Products and Bioprospecting 2017年第5期7卷 405-411页

作者： Yu-Chen Liu Zhi-Jun Zhang Jia Su Li-Yan Peng Lu-Tai Pan Xing-De Wu Qin-Shi Zhao State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunming 650201People’s Republic of China University of Chinese Academy of Sciences Beijing 100039People’s Republic of China Guiyang College of Traditional Chinese Medicine GuiyangPeople’s Republic of China

t Three new lycodine-type lycopodium alkaloids,namely 1-methyllycodine(1),8a-hydroxy-15,16-dehydro-desN-methyl-a-obscurine(2),N-methyl-16-hydroxyhuperzine B(3),and one new natural lycodine-type lycopodium alkaloid,N-methylhuperzine A(4),along with 11 known analogues(5–15),were isolated from the whole plants of club moss Huperzia *** structures of 1–4 were elucidated on the basis of NMR spectroscopic and mass spectrometry *** them,compound 1 was the first lycodine-type alkaloid possessing a methyl group at *** addition,the structure of 5 was confirmed by the single-crystal X-ray crystallography data and its^(13)C NMR was reported for the first time in current *** 1–5 were tested their BACE1 inhibitory activity.

关键词： lycopodium alkaloids Lycodine-type Huperzia serrata BACE1 inhibitory activity

Two Novel Hydroperoxylated lycopodium alkaloids from Huperzia serrata

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Acta Botanica Sinica 2003年第1期45卷 118-121页

作者：谭昌恒马晓强周慧蒋山好朱大元中国科学院上海生命科学研究院上海药物研究所国家新药研究重点实验室上海200031

Two novel hydroperoxylated lycopodium alkaloids, 11alpha-hydroperoxyphlegmariurine B (1) and 7-hydroperoxyphlegmariurine B (2), along with a known compound, phlegmanurine B (3), were isolated from the total alkaloid fraction of the Chinese medicinal herb Huperzia serrata (Thunb.) Trev. Their structures and relative configurations were elucidated on the basis of spectroscopic analyses.

关键词： Huperzia serrata lycopodium alkaloids 11 alpha-hydroperoxyphlegmariurine B 7-hydroperoxyphlegmaniurine B

Total Synthesis of Palhinine-Type lycopodium alkaloids

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Total Synthesis of Palhinine-Type Lycopodium Alkaloids

Chemical constituents and biological activities of lycophytes and ferns

中国化学会第十四届全国有机合成化学学术研讨会

作者： Chun-An Fan State Key Laboratory of Applied Organic Chemistry College of Chemistry and Chemical Engineering Lanzhou University

alkaloids are of biologically significant molecules that are widely investigated in pharmaceutics and medicines. Palhinine A and Palhinine D as two members of lycopodium alkaloids were isolated from Palhinhaea cernua L. in 2010 and 2013, respectively. These alkaloids are structurally featured by the unique tetracyclic framework with five stereogenic centers(two contiguous all-carbon quaternary centers). Due to its intriguing bridged core skeleton as well as the potential biological interest, the synthetic studies of palhinine-type lycopodium alkaloids have evoked much interest in the synthetic community. In this presentation, we will present the recent efforts on the total synthesis of lycopodium alkaloids Palhinine A, Palhinine D, and their C3-epimers.

关键词： azonane ring auxiliary ring construction/deconstruction lycopodium alkaloids total synthesis

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Chinese Journal of Natural Medicines 2019年第12期17卷 887-891页

作者： ZHU Qin-Feng ZHAO Qin-Shi State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of Botany Chinese Academy of Sciences

Lycophytes and ferns are unique and charismatic members of many terrestrial ecosystems and occupy the pivotal position in land plant origin and *** Chinese lycophytes and ferns flora,with approximately 2000 species,contributes a substantial component to the global lycophytes and ferns diversity,with estimates of 12000 *** them,about 433 species are medicinally recorded and researches based on their phytochemical properties are important topics in natural *** paper reviewed the research history and current status of chemical constituents and biological activities of lycophytes and ferns,which had highlighted the research progress of our group.

关键词： Lycophytes Ferns Chemical constituents Biological activities lycopodium alkaloids

A new lycopodium alkaloid from Phlegmariurus fargesii

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Chinese Journal of Natural Medicines 2014年第5期12卷 373-376页

作者： PAN Ke LUO Jian-Guang KONG Ling-Yi State Key Laboratory of Natural Medicines Department of Natural Medicinal Chemistry China Pharmaceutical University

AIM: To investigate the chemical constituents from the whole plants of Phlegmariurus fargesii. METHOD: Compounds were isolated by repeated silica gel column chromatography. Their structures were elucidated by spectroscopic methods and chemical correlation. The acetylcholinesterase(AChE) inhibitory activity of the isolated compounds was evaluated. RESULTS: A new lycopodium alkaloid, lycopodine N-oxide(1), along with lycopodine(2), 8,15-dehydrolycopodine(3), 6α-hydroxylycopodine(4), deacetyllycoclavine(5), N-methylhuperzine B(6), lycodine(7), and phlegmarine(8), was isolated. CONCLUSION: Compound 1 is a new lycopodium alkaloid, and compound 3 was obtained from nature for the first time. Other alkaloids are isolated from this plant for the first time.

关键词： Phlegmariurusfargesii lycopodium alkaloids Lycopodine N-oxide

Discovery and Asymmetric Total Synthesis of Phlegmine A as a Selective Inhibitor of ASIC1a

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CCS Chemistry 2024年第10期6卷 2529-2536页

作者： Zai-Feng Yuan Fei Liu Yu-Fei Ou Wen-Yan Li Li-Yan Peng Xiao-Nian Li Qin-Shi Zhao State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunming 650201 School of Pharmacy Chengdu University of Traditional Chinese MedicineChengdu 611137 University of Chinese Academy of Sciences Beijing 10049

Phlegmine A(1),a novel type of lycopodium alkaloid with a unique skeleton,was isolated from the rare and endangered herbal medicinal plant,Phlegmariurus *** methods and X-ray diffraction analysis were employed to unambiguously elucidate the structure of phlegmine A(1).Furthermore,we realized the asymmetric total synthesis of the natural product phlegmine A(1)in 18 linear steps from commercial ingredients,achieving a 1.3%overall *** intramolecular carbene cyclization,dimethyldioxirane(DMDO)enamine oxidation,and Stevens rearrangement were exploited to establish the sterically congested vicinal quaternary centers,and an epimerization/aldol condensation/deacetylation reaction was utilized for the rapid assembly of enone at the final *** our semisynthesis attempts,a novel transformation was developed to constructα-aminoketone from enamine ***,the synthetic sample obtained from this work enabled the successful verification of phlegmine A(1)as a new type of highly selective acidsensing ion channel 1a(ASIC1a)inhibitor,which also exerted an in vivo analgesic effect,rendering it a promising lead compound.

关键词： lycopodium alkaloids phlegmine A total synthesis ASIC1a inhibitor analgesic

One-step synthesis of lycopodium alkaloid(-)-huperzine W via Suzuki-Miyaura coupling

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Natural Products and Bioprospecting 2012年第6期2卷 255-257页

作者： Tao XU Shi-Zhi JIANG Huai-Rong LUO Yu-Rong YANG State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of BotanyChinese Academy of SciencesKunming 650201China University of Chinese Academy of Sciences Beijing 100049China

The first total synthesis of(-)-huperzine W(1)has been *** element of the synthesis is a highly convergent assemblage for the two rings system of target molecule utilizing an efficient Suzuki-Miyaura coupling reaction between chiral iodide 2 and 2-allylpyrrolidinone *** of the AchE inhibition of synthetic huperzine W was also carried out.

关键词： total synthesis huperzine W lycopodium alkaloids

Total Syntheses of （-）-Lycopodine and （-）-Lycospidine A via Phosphoric Acid Promoted Alkyne Aza-Prins Cyclization

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Total Syntheses of （-）-Lycopodine and （-）-Lycospidine A ...