Leishmanicidal, Antiplasmodial, and Cytotoxic Activity of Novel Diterpenoid 1,2-Quinones from Perovskia abrotanoides:  New Source of Tanshinones

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2001-11, Vol.64 (11), p.1398-1403
• Main Authors: Sairafianpour, Majid, Christensen, Jette, Stærk, Dan, Budnik, Bogdan A, Kharazmi, Arsalan, Bagherzadeh, Karim, Jaroszewski, Jerzy W
• Format: Article
• Language: English
• Subjects: Animals; Anti-Infective Agents - chemistry; Anti-Infective Agents - isolation & purification; Anti-Infective Agents - pharmacology; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; Antiprotozoal Agents - chemistry; Antiprotozoal Agents - isolation & purification; Antiprotozoal Agents - pharmacology; Biological and medical sciences; Chromatography, Thin Layer; Diterpenes - chemistry; Diterpenes - isolation & purification; Diterpenes - pharmacology; Diterpenes, Abietane; Drug Resistance - physiology; General pharmacology; Humans; Iran; Lamiaceae - chemistry; Leishmania major - drug effects; Lymphocytes - blood; Lymphocytes - drug effects; Medical sciences; Nuclear Magnetic Resonance, Biomolecular; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Phenanthrenes - chemistry; Phenanthrenes - isolation & purification; Phenanthrenes - pharmacology; Phytohemagglutinins - pharmacology; Plant Lectins; Plant Roots - chemistry; Plants, Medicinal - chemistry; Plasmodium falciparum - drug effects; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; Tumor Cells, Cultured - drug effects
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np010032f

Cryptotanshinone (1), a quinoid diterpene with a nor-abietane skeleton, and three new natural products, 1β-hydroxycryptotanshinone (2), 1-oxocryptotanshinone (3), and 1-oxomiltirone (4), were isolated from roots of the Iranian medicinal plant Perovskia abrotanoides. Their structures were established using homo- and heteronuclear two-dimensional NMR experiments, supported by HRMS. The total amount of tanshinones isolated from dry roots of Perovskia abrotanoides was about 1.5%. The compounds exhibited leishmanicidal activity in vitro (IC50 values in the range 18−47 μM). These findings provide a rationale for traditional use of the roots in Iran as a constituent of poultices for treatment of cutaneous leishmaniasis. The isolated tanshinones also inhibited growth of cultured malaria parasites (3D7 strain of Plasmodium falciparum), drug-sensitive KB-3-1 human carcinoma cell line, multidrug-resistant KB-V1 cell line, and human lymphocytes activated with phytohaemagglutinin A (IC50 values in the range 5−45 μM). The toxicity of tanshinones toward the drug-sensitive KB-3-1 and the multidrug-resistant KB-V1 cells was the same, indicating that the compounds are not substrates for the P-glycoprotein drug efflux pump.