Quaternary Alkaloids from Litsea cubeba and Cryptocarya konishii

Lee, Shoei‐Sheng; Lin, Yi-Jean; Chen, Chien-Kuang; Liu, Karin C. S.; Chen, Chung‐Hsiung

doi:10.1021/np50101a016

Cited by 46 publications

(30 citation statements)

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“…In continuation of our work on phytochemistry and biological evaluation of the metabolites from lauraceous plants, we examined the activity of the MeOH extract of the tree bark of C. konishii Hayata grown in Indonesia against P-388 cells and tyrosine kinase, showing it significantly inhibited both the cells (IC 50 6.5 lg/mL) and the enzyme (% inhibition of 48.9 at 100 lg/mL). This plant has been shown to contain a number of alkaloid derivatives [11][12][13]. In this paper, we report the isolation of two new chalcone derivatives, 2 0 -hydroxychalcone (1) and desmethylinfectocaryone (2), along with five known phenolic derivatives 3-7 ( Fig.…”

Section: Introductionmentioning

confidence: 93%

Phenolic compounds from Cryptocarya konishii: their cytotoxic and tyrosine kinase inhibitory properties

et al. 2009

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Two chalcone derivatives, 2'-hydroxychalcone (1) and desmethylinfectocaryone (2), together with five known phenolic compounds infectocaryone (3), cryptocaryone (4), kurzichalcolactone A (5), pinocembrin (6) and trans-N-feruloyltyramine (7), were isolated from the methanol extract of the wood of Cryptocarya konishii. The structures of the new compounds were determined based on the analysis of spectroscopic data, including UV, IR, 1D and 2D NMR, and mass spectra. Evaluation of the cytotoxic and tyrosine kinase inhibitory activities of compounds 1-7 showed that compounds 2-4 strongly inhibited the growth of murine leukemia P-388 cells, whereas compound 4 significantly inhibited the enzyme.

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Section: Introductionmentioning

confidence: 93%

Phenolic compounds from Cryptocarya konishii: their cytotoxic and tyrosine kinase inhibitory properties

et al. 2009

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“…The plant genus Cryptocarya (Lauraceae) includes over 200 species which are commonly distributed all over the tropical and subtropical regions of the world . Phytochemical studies on this species have led to the discovery of a variety of secondary metabolites, which include lignans, benzylisoquinolines,– proaporphine alkaloids,– flavonoids, cryptochinones, pavines,– and a variety of α ‐pyrone derivatives –. Many of these compounds display numerous biological activities, such as antioxidant, cytotoxic,, antimycobacterial, and antiparacytic activities.…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of Cryptorigidifoliol K: Confirmation of Structure and Absolute Configuration

et al. 2018

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Total synthesis of the revised cryptorigidifoliol K and 2'-epi-cryptorigidifoliol K was accomplished. Salient features of the synthesis involve tandem isomerization followed by CÀ O and CÀ C bond forming reaction, iodolactonization and Nozaki-Hiyama-Kishi reaction. The synthesis allowed for confirmation of the structure as well as the elucidation of the unassigned stereocenter present in the side chain of the revised structure by correlating the spectral and analytical data of the synthetic cryptorigidifoliol K and 2'epi-cryptorigidifoliol K with the natural product data, which was found to be 1S,5R,7S,2'R,3'E.[a] G.

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“…The essential oil from L. cubeba has good fungicidal activities against Sclerotinia sclerotiorum , Thanatephorus cucumeris , Pseudocercospora musae and Colletotrichum gloeosporioides [8,9]. Various types of alkaloids have been isolated from this plant [10,11,12]. Litebamine and its N- homologues possess acetylcholinesterase activity [13].…”

Section: Introductionmentioning

confidence: 99%

Antibacterial, Antifungal and Cytotoxic Isoquinoline Alkaloids from Litsea cubeba

Zhang

et al. 2012

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Five novel isoquinoline alkaloids (+)-N-(methoxylcarbonyl)-N-nordicentrin (1), (+)-N-(methoxylcarbonyl)-N-norpredicentrine (2), (+)-N-(methoxylcarbonyl)-N-norbulbodione (3), and (+)-N-(methoxylcarbonyl)-N-norisocorydione (4), and (+)-8-methoxyisolaurenine-N-oxide (5) were isolated, together with one known compound, (+)-N-(methoxylcarbonyl)-N-norglaucine (6), from a 70% EtOH extract of the barks of Litsea cubeba. Structural elucidation of all the compounds were performed by spectral methods such as 1D- and 2D-NMR, IR, UV, and HRESIMS. Alkaloids 1, 2 and 6 showed antimicrobial activity against the bacterium S. aureus and two fungi (A. alternata and C. nicotianae). Compounds 3,4 exhibited significant cytotoxicity against all of six tested tumor cell lines.

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Quaternary Alkaloids from Litsea cubeba and Cryptocarya konishii

Cited by 46 publications

References 10 publications

Phenolic compounds from Cryptocarya konishii: their cytotoxic and tyrosine kinase inhibitory properties

Phenolic compounds from Cryptocarya konishii: their cytotoxic and tyrosine kinase inhibitory properties

Total Synthesis of Cryptorigidifoliol K: Confirmation of Structure and Absolute Configuration

Antibacterial, Antifungal and Cytotoxic Isoquinoline Alkaloids from Litsea cubeba

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