• Title/Summary/Keyword: Oxoaporphine alkaloid

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Cytotoxic C-Benzylated Chalcone and Other Constituents of Ellipeiopsis cherrevensis

  • Wirasathien, Lalita;Pengsuparp, Thitima;Moriyasu, Masataka;Kawanishi, Kazuko;Suttisri, Rutt
    • Archives of Pharmacal Research
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    • v.29 no.6
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    • pp.497-502
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    • 2006
  • A new natural C-benzylated chalcone, $2',4'-dihydroxy-3'-(2-hydroxybenzyl)-6{\c}-methoxychalcone$ (2), along with two other flavonoids, tiliroside and kaempferol 3-O-rutinoside, and an oxoaporphine alkaloid, lanuginosine were isolated from the aerial parts of Ellipeiopsis cherrevensis (Annonaceae). Two known polyoxygenated cyclohexene derivatives, ferrudiol and zeylenol, and a new analog, ellipeiopsol D, were also isolated. The chalcone 2 exhibited cytotoxic activity against human small-cell lung-cancer (NCl-H187), epidermoid carcinoma (KB) and breast cancer (BC) cell lines with $IC_{50}$ values of 1.40, 5.31 and $13.92\;{\mu}g/mL$, respectively. This compound also showed antimalarial activity against Plasmodium falciparum with an $IC_{50}$ value of $7.1\;{\mu}g/mL$ as well as antimicrobacterial activity against Mycobacterium tuberculosis with a MIC of 25 mg/mL.

New Azafluorenone Derivative and Antibacterial Activities of Alphonsea cylindrica Barks

  • Talip, Munirah Abdul;Azziz, Saripah Salbiah Syed Abdul;Wong, Chee Fah;Awang, Khalijah;Naz, Humera;Bakri, Yuhanis Mhd;Ahmad, Mohamad Syahrizal;Litaudon, Marc
    • Natural Product Sciences
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    • v.23 no.3
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    • pp.151-156
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    • 2017
  • A phytochemical study of Alphonsea cylindrica King (unreported) has led to the isolation of six alkaloids. The compounds were identified as kinabaline (1; azafluorenone alkaloid), muniranine (2), O-methylmoschatoline (3; oxoaporphine alkaloid), lysicamine (4), atherospermidine (5) and N-methylouregidione (6; 4, 5-dioxoaporphine alkaloid). The structures of the isolated compounds were determined based on the spectroscopic techniques and by comparison with data reported in the literature. Alkaloid 2 was isolated as a new derivative of azafluorenone while alkaloids 1, 3 - 6 were isolated for the first time from Alphonsea species. In addition, alkaloid 3 and 4 showed inhibition zone against Staphylococcus aureus, Pseudomonas aeruginosa and Bacillus cereus in disc diffusion test. The minimum inhibition concentration (MIC) values of lysicamine (4) against S. aureus, B. cereus and P. aeruginosa were found to be smaller than O-methylmoschatoline (3). Therefore, the reported antibacterial activity showed the potential of this plant as natural antibacterial agent and supported the documented traditional use of Alphonsea sp. in the treatment of diarrhea and fever.