Four new bioactive manzamine-type alkaloids from the Philippine marine sponge Xestospongia ashmorica

Edrada-Ebel, Ruangelie and Proksch, P and Wray, V and Witte, L and Müller, W E and Van Soest, R W (1996) Four new bioactive manzamine-type alkaloids from the Philippine marine sponge Xestospongia ashmorica. Journal of Natural Products, 59 (11). pp. 1056-1060. ISSN 0163-3864

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Abstract

Analysis of the Philippine marine sponge Xestospongia ashmorica afforded four new manzamine congeners 1-4 and four known compounds 5 and 7-9. Compound 1 is the 6-deoxy derivative of manzamine X, while 2-4 are the N-oxides of manzamine J (5), 3,4-dihydromanzamine A (6), and manzamine A (7), respectively. The structures of the new compounds were unambiguously established on the basis of NMR spectroscopic (1H, 13C, COSY, 1H-detected direct, and long-range 13C-1H correlations) and mass spectrometric (EI, FAB-MS, and electrospray ionization) data. Alkaloid N-oxide structures were confirmed by conversion to the corresponding tertiary bases by reduction with Zn/HCl. This is the first report of the occurrence of bioactive manzamine N-oxides in marine sponges. Compound 7 exhibited insecticidal activity toward neonate larvae of the polyphagous pest insect Spodoptera littoralis (with an ED50 of 35 ppm) when incorporated in artificial diet and offered to larvae in a chronic feeding bioassay. Compound 7 was also active against the Gram-positive bacteria Bacillus subtilis and Staphylococcus aureus. Cytotoxicity was studied in vitro using L1578y mouse lymphoma cells. From the alkaloids studied, the N-oxides 3 and 4 were the most active (ED50 = 1.6 micrograms/mL) followed by compound 7 (ED50 = 1.8 micrograms/mL).

  • Item type:Article
    ID code:48521
    Dates:
    Date
    Event
    November 1996
    Published
    22 November 1996
    Published Online
    Keywords:alkaloids, animals, anti-bacterial agents, antineoplastic agents, drug screening assays, antitumor, insecticides, magnetic resonance spectroscopy, mice, microbial sensitivity tests, philippines, porifera, spectrometry, mass, fast atom bombardment, spectrophotometry, infrared, tumor cells, cultured, Pharmacy and materia medica, Therapeutics. Pharmacology, Organic Chemistry, Drug Discovery, Pharmaceutical Science, Molecular Medicine, Complementary and alternative medicine, Analytical Chemistry, Pharmacology
    Subjects:Medicine > Pharmacy and materia medica
    Medicine > Therapeutics. Pharmacology
    Department:Faculty of Science > Strathclyde Institute of Pharmacy and Biomedical Sciences
    Depositing user: Pure Administrator
    Date deposited:13 Jun 2014 11:37
    Last modified:14 May 2021 02:25
    URI:https://strathprints.strath.ac.uk/id/eprint/48521
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