Antimicrobial and antiparasitic (+)-trans-hexahydrodibenzopyrans and analogues from Machaerium multiflorum

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2003-06, Vol.66 (6), p.804-809
• Main Authors: Muhammad, I, Li, X.C, Jacob, M.R, Tekwani, B.L, Dunbar, D.C, Ferreira, D
• Format: Article
• Language: English
• Subjects: Animals; Anti-Infective Agents - chemistry; Anti-Infective Agents - isolation & purification; Anti-Infective Agents - pharmacology; antibacterial properties; antifungal properties; antimalarials; Antimalarials - chemistry; Antimalarials - isolation & purification; Antimalarials - pharmacology; Antiparasitic Agents - chemistry; Antiparasitic Agents - isolation & purification; Antiparasitic Agents - pharmacology; bark; benzene; Benzopyrans - chemistry; Benzopyrans - isolation & purification; Benzopyrans - pharmacology; Biological and medical sciences; Candida albicans; Candida albicans - drug effects; carbon; chemical structure; circular dichroism spectroscopy; Fabaceae - chemistry; Faboideae; General pharmacology; heterocyclic compounds; hexahydrodibenzopyran; Inhibitory Concentration 50; Leishmania donovani; Leishmania donovani - drug effects; machaeridiols; machaeriols; Machaerium; Machaerium multiflorum; Medical sciences; Methicillin Resistance; Microbial Sensitivity Tests; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Peru; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; phytochemicals; Plant Bark - drug effects; plant extracts; Plants, Medicinal - chemistry; Plasmodium falciparum; Plasmodium falciparum - drug effects; protons; pyrans; spectral analysis; Staphylococcus aureus; Staphylococcus aureus - drug effects; stems; stereochemistry; Stereoisomerism; stilbenes; styrene
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np030045o

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 (IC(50) 0.65 microg/mL) and methicillin-resistant S. aureus (MRSA) (IC(50) 0.70 microg/mL), while its corresponding 5,6-seco-analogues machaeridiol A (3) and machaeridiol B (4) showed antibacterial activity against S. aureus and MRSA (IC(50) 1.0-2.6 microg/mL) and antifungal activity against Candida albicans (IC(50), 2.0-3.5 microg/mL). In addition, machaeridiol B (4) demonstrated antiparasitic activities against Plasmodium falciparum D6 and W2 clones and Leishmania donavani with IC(50) values of 0.64, 0.22, and 0.9 microg/mL, respectively.