Synthesis of Artekeiskeanin A: A New Coumarin Monoterpene Ether from Artemisia keiskeana

Maes, Dominick; Syngel, Kris Van; Kimpe, Norbert De

doi:10.3987/com-07-s(w)1

Cited by 2 publications

(1 citation statement)

References 9 publications

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“…1 H-NMR (500 MHz, CDCl 3 ) δ ppm: 7.65 (1H, d, J = 9.5 Hz, H-4), 6.87 (1H, s, H-5), 6.84 (1H, s, H-8), 6.29 (1H, d, J = 9.5 Hz, H-3), 5.50 (1H, t, H-2'), 5.08 (1H, t, H-6'), 4.71 (2H, d, J = 6.0 Hz, H-1'), 3.93 (3H, s, 6-OCH 3 ), 2.13 (2H, m, H-5'), 2.10 (2H, m, H-4'), 1.79 (3H, s, H-9'), 1.67 (3H, s, H-8'), 1.61 (3H, s, H-10'). 13 C-NMR (125 MHz, CDCl 3 ) δ ppm: 161.5 (C-2), 152.1 (C-7), 150.0 (C-9), 146.7 (C-6), 143.3 (C-4), 142.1 (C-3'), 131.9 (C-7'), 123.6 (C-6'), 118.5 (C-2'), 113.3 (C-3), 111.3 (C-10), 108.1 (C-5), 101.2 (C-8), 66.3 (C-1'), 56.4 (6-OCH 3 ), 39.5 (C-4'), 26.2 (C-5'), 25.6 (C-8'), 17.7 (C-10'), 16.9 (C-9') [22].…”

Section: Methodsmentioning

confidence: 99%

Cytotoxic Compounds Isolated from Murraya tetramera Huang

et al. 2014

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Abstract:A new compound and seven known compounds were isolated from Murraya tetramera Huang for the first time, and they were identified with NMR and MS spectral analysis. It was confirmed that the new compound was 10-methoxy-7-methyl-2H-benzo[g]chromen-2-one (3) and the others were β-eudesmol (1), trans-3β-(1-hydroxy-1-methylethyl)-8aβ-methyl-5-methylenedecalin-2-one (2), 5,7-dimethoxy-8-[(Z)-3'-methylbutan-1',3'-dienyl]coumarin (4), 7-geranyloxy-6-methoxycoumarin (5), 5,7-dimethoxy-8-(3-methyl-2-oxo-butyl)coumarin (6), murrangatin acetate (7) and toddalenone (8). Furthermore, the cytotoxic activity against human lung adenocarcinoma (A549), human hepatocellular carcinoma cells (SMMC-7721), human bladder tumor cells (EJ), human cervical carcinoma cells (HeLa), and human B-lineage acute lymphoblastic leukemia 1 cells (BALL-1) was evaluated for all compounds. It was found that five of them displayed various degrees of OPEN ACCESSMolecules 2014, 19 13226 cytotoxicity against different testing targets. Compound 1 showed significant cytotoxic activity against the five cell lines (A549, SMMC-7721, EJ, Hela and BALL-1). Compounds 2 and 5 showed significant cytotoxicity against three cell lines (A549, SMMC-7721 and BALL-1). Compound 4 showed significant cytotoxicity against three cell lines (A549, EJ and BALL-1). However, compound 3 only showed fair cytotoxicity against the BALL-1 cell line. The structure-active relationships were investigated as well. These active compounds might be potential lead compounds for the treatment of cancer.

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Section: Methodsmentioning

confidence: 99%

Cytotoxic Compounds Isolated from Murraya tetramera Huang

et al. 2014

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ChemInform Abstract: Synthesis of Artekeiskeanin A: A New Coumarin Monoterpene Ether from Artemisia keiskeana.

2008

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Terpenes U 0200 Synthesis of Artekeiskeanin A: A New Coumarin Monoterpene Ether from Artemisia keiskeana. -The total synthesis of artekeiskeanin (III) involves the selective monoxidation of the geranyloxy side chain of coumarin (II) under microwave irradiation as the key step. -(MAES, D.; VAN SYNGEL, K.; DE KIMPE*, N.; Heterocycles 74 (2007) 1, 927-930; Dep. Org. Chem., Fac. Biosci. Eng., Univ. Gent, B-9000 Gent, Belg.; Eng.) -C. Cyrus 23-182

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Synthesis of Artekeiskeanin A: A New Coumarin Monoterpene Ether from Artemisia keiskeana

Cited by 2 publications

References 9 publications

Cytotoxic Compounds Isolated from Murraya tetramera Huang

Cytotoxic Compounds Isolated from Murraya tetramera Huang

ChemInform Abstract: Synthesis of Artekeiskeanin A: A New Coumarin Monoterpene Ether from Artemisia keiskeana.

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