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Crystallographic and NMR studies of antiinfective tricyclic guanidine alkaloids from the sponge Monanchora unguifera |
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| Authors: | Hua Hui-ming Peng Jiangnan Fronczek Frank R Kelly Michelle Hamann Mark T |
| Affiliation: | aDepartment of Pharmacognosy, School of Pharmacy, University of Mississippi, University, MS 38677, USA bNational Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS 38677, USA cDepartment of Natural Product Chemistry, School of Traditional Chinese Medicines, Shenyang Pharmaceutical University, Shenyang 110016, China dChemistry Department, Louisiana State University, Baton Rouge, LA 70803-1804, USA eNational Centre for Aquatic Biodiversity and Biosecurity, National Institute of Water and Atmospheric Research Ltd, Newmarket, Auckland, New Zealand |
| Abstract: | Three tricyclic guanidine alkaloids, including 1,8a;8b,3a-didehydro-8β-hydroxyptilocaulin (1), 1,8a;8b,3a-didehydro-8-hydroxyptilocaulin (2) and mirabilin B (3), were identified from the marine sponge Monanchora unguifera. 1,8a;8b,3a-Didehydro-8-hydroxyptilocaulin (2) is a new stereoisomer of 1, the structure of which was elucidated by spectroscopic analysis, comparison of its spectral data with those of 1, and confirmed by X-ray analysis. Compounds 1 and 2 co-crystallized in an unusual perfect order and packed around an approximate inversion center. A mixture of 1 and 2 is active against the malaria parasite Plasmodium falciparum with an IC50 value of 3.8 μg/mL while mirabilin B (3) exhibited antifungal activity against Cryptococcus neoformans with an IC50 value of 7.0 μg/mL and antiprotozoal activity against Leishmania donovani with an IC50 value of 17 μg/mL. |
| Keywords: | Tricyclic guanidine alkaloids Monanchora unguifera Sponge X-ray crystallography Antimalarial Antifungal |
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