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Antimicrobial and Antiparasitic (+)-trans-Hexahydrodibenzopyrans and Analogues from Machaerium multiflorum

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National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, Mississippi 38677
Cite this: J. Nat. Prod. 2003, 66, 6, 804–809
Publication Date (Web):May 30, 2003
https://doi.org/10.1021/np030045o
Copyright © 2003 American Chemical Society and American Society of Pharmacognosy
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    Abstract

    Machaerium multiflorum yielded two additional new (+)-trans-hexahydrodibenzopyrans (HHDBP's), machaeriol C (1) and machaeriol D (2), and three new 5,6-seco-HHDBP's, machaeridiol A (3), machaeridiol B (4), and machaeridiol C (5). Their structures and stereochemistries were determined by 1D and 2D NMR data, including HMBC, NOESY, and circular dichroism experiments. Machaeriol C (1) demonstrated in vitro antibacterial activity against Staphylococcus aureus (IC50 0.65 μg/mL) and methicillin-resistant S. aureus (MRSA) (IC50 0.70 μg/mL), while its corresponding 5,6-seco-analogues machaeridiol A (3) and machaeridiol B (4) showed antibacterial activity against S. aureus and MRSA (IC50 1.0−2.6 μg/mL) and antifungal activity against Candida albicans (IC50, 2.0−3.5 μg/mL). In addition, machaeridiol B (4) demonstrated antiparasitic activities against Plasmodium falciparum D6 and W2 clones and Leishmania donavani with IC50 values of 0.64, 0.22, and 0.9 μg/mL, respectively.

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