Carinatines A and B, Lycopodium Alkaloids from Phlegmariurus carinatus

Liu, Fei; Liu, Yucheng; Jiang, Weiwei; He, Juan; Wu, Xing‐De; Peng, Li‐Yan; Su, Jia; Cheng, Xiuwen; Zhao, Qin‐Shi

doi:10.1007/s13659-014-0030-6

Cited by 22 publications

(24 citation statements)

References 31 publications

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“…Carinatine A (22) with a unique 5/6/6/6 ring system was first identified from P. carinatus, and its absolute configuration remains unassigned. 31 The concomitant isolation of 18 and 22 in the present study, together with their well-matched ECD curves (Figure S19, Supporting Information), established a (7S,12S,15R) absolute configuration for 22.…”

Section: ■ Results and Discussionsupporting

confidence: 61%

“…The 13 C NMR (Table ) and HMQC data showed 16 carbon resonances, of which the one at δ C 149.3 (C-13) could be assigned to a nitrone moiety. A comparison of the 1D NMR data of 18 with those of carinatine A ( 22 ) revealed that 18 was the 8-hydroxy derivative of carinatine A, which was supported by the 2D NMR data of 18 (Figure S17, Supporting Information). Notably, H-14b (δ H 2.38) showed a ddt splitting pattern ( J = 19.0, 6.0, 2.9 Hz), which was consistent with the 1 H– 1 H COSY correlation of H-14b/H 2 -9, implying unusual five-bond couplings between H-14b and H 2 -9.…”

Section: Results and Discussionmentioning

confidence: 59%

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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 Discussionsupporting

confidence: 61%

Section: Results and Discussionmentioning

confidence: 59%

Lycosquarrines A–R, Lycopodium Alkaloids from Phlegmariurus squarrosus

et al. 2020

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“…Their structures are shown below, and their names and the corresponding plant sources are listed in the Table. As it can be seen, alkaloids and serratane‐type triterpenoids are the dominant chemical constituents in the plants of the genus Phlegmariurus .…”

Section: Chemical Constituentsmentioning

confidence: 99%

Chemical Constituents of Plants from the Genus Phlegmariurus

Yang

Wang

et al. 2016

Chemistry & Biodiversity

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“…P. carinatus was used as a traditional herbal medicine in China for long time (Liu et al. 2014 ). It has significant curative effect on rheumatoid arthritis, rheumatoid arthritis, muscle and bone pain (Zhang et al.…”

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confidence: 99%

The complete chloroplast genome sequence of Phlegmariurus carinatus

Luo

Yuan

et al. 2019

Mitochondrial DNA Part B

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The first complete chloroplast genome (cpDNA) sequence of Phlegmariurus carinatus was determined from Illumina HiSeq pair-end sequencing data in this study. The cpDNA is 150,349 bp in length, contains a large single-copy region (LSC) of 100,582 bp and a small single-copy region (SSC) of 19,455 bp, which were separated by a pair of inverted repeat (IR) regions of 15,156 bp. The genome contains 120 genes, including 79 protein-coding genes, 8 ribosomal RNA genes, and 33 transfer RNA genes. The overall GC content of the whole genome is 34.0%, and the corresponding values of the LSC, SSC, and IR regions are 31.6%, 30.4%, and 44.2%, respectively. Further phylogenomic analysis showed that P. carinatus and Huperzia serrata clustered in a clade in family Lycopodiaceae. ARTICLE HISTORY

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Carinatines A and B, Lycopodium Alkaloids from Phlegmariurus carinatus

Cited by 22 publications

References 31 publications

Lycosquarrines A–R, Lycopodium Alkaloids from Phlegmariurus squarrosus

Lycosquarrines A–R, Lycopodium Alkaloids from Phlegmariurus squarrosus

Chemical Constituents of Plants from the Genus Phlegmariurus

The complete chloroplast genome sequence of Phlegmariurus carinatus

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