Anti-leishmanial activity of neolignans from Virola species and synthetic analogues

• Published in: Phytochemistry (Oxford) Vol. 55; no. 6; pp. 589 - 595
• Main Authors: Barata, Lauro E.S, Santos, Lourivaldo S, Ferri, Pedro H, Phillipson, J.David, Paine, Angela, Croft, Simon L
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.11.2000; Elsevier
• Subjects: 3,4,5-Trimethoxy-8-[2',6'-dimethoxy-4'-(E)-propenylphenoxy]- phenyl-propane; Animals; Anisoles - chemistry; Anisoles - isolation & purification; Anisoles - pharmacology; Anti-leishmanial activity; Antiprotozoal Agents - chemistry; Antiprotozoal Agents - isolation & purification; Antiprotozoal Agents - pharmacology; Biochemistry & Molecular Biology; Biological and medical sciences; Chemical constitution; Disease Models, Animal; Drug Evaluation, Preclinical; Female; Fundamental and applied biological sciences. Psychology; General pharmacology; Leishmania donovani; Leishmania donovani - drug effects; Leishmaniasis, Visceral - drug therapy; Life Sciences & Biomedicine; Lignans - chemistry; Lignans - isolation & purification; Lignans - pharmacology; Magnoliopsida - chemistry; Medical sciences; Mice; Mice, Inbred BALB C; Myristicaceae; Neolignans; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Plant physiology and development; Plant Sciences; Science & Technology; surinamensin; Virola; Virola pavonis; Virola surinamensis; β-Ketoamines; β-Ketoethers; β-Ketosulfides; β-Ketoamines; Virola surinamensis; Virola pavonis; Neolignans; Leishmania donovani; β-Ketoethers; Myristicaceae; β-Ketosulfides; Anti-leishmanial activity; beta-ketoethers; DONOVANI; NATURAL-PRODUCTS; anti-leishmanial activity; FIGHT; beta-ketosulfides; beta-ketoamines; neolignans; DRUGS; AMAZONENSIS; ANTILEISHMANIAL ACTIVITY; Kinetoplastida; Protozoa; Protozoal disease; Molecular structure; Pharmacognosy; Parasitosis; Leishmaniasis; In vitro; Biological activity; Medicinal plant; Infection; Structure activity relation; Dicotyledones; Analog; Angiospermae; Parasiticid; Plant origin; Isolation; Lignan; Spermatophyta; Chemical synthesis
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/S0031-9422(00)00240-5

Surinamensin, a neolignan isolated from Virola surinamensis, 3,4,5-trimethoxy-8-[2′,6′-dimethoxy-4′-(E)-propenylphenoxy]-phenylpropane, a neolignan isolated from Virola pavonis, and 25 of its synthetic analogues or correlated substances with ether linkages and their corresponding C-8 sulphur and nitrogen analogues, were tested for activity against Leishmania donovani amastigotes and promastigotes in vitro. Some were active against L. donovani promastigotes at 30 μM but inactive against intracellular amastigotes.The natural neolignan from V. pavonis was active against promastigotes at 100 μM. The highest selective activity was found in those compounds with sulphur bridges.The β-ketosulfide (3,4-dimethoxy)-8-(4′-methylthiophenoxy)-propiophenone produced 42% inhibition of L. donovani amastigotes in the liver of BALB/c mice at 100 mg/kg given once daily for five consecutive days ( P>0.05).