Antiplasmodial Quinones from Pentas longiflora and Pentas lanceolata

Abstract

The dichloromethane/methanol (1 : 1) extracts of the roots of Pentas longiflora and Pentas lanceolata showed low micromolar (IC₅₀ = 0.9–3 µg/mL) in vitro antiplasmodial activity against chloroquine-resistant (W2) and chloroquine-sensitive (D6) strains of Plasmodium falciparum. Chromatographic separation of the extract of Pentas longiflora led to the isolation of the pyranonaphthoquinones pentalongin (1) and psychorubrin (2) with IC₅₀ values below 1 µg/mL and the naphthalene derivative mollugin (3), which showed marginal activity. Similar treatment of Pentas lanceolata led to the isolation of eight anthraquinones (4–11, IC₅₀ = 5–31 µg/mL) of which one is new (5,6-dihydroxydamnacanthol, 11), while three – nordamnacanthal (7), lucidin-ω-methyl ether (9), and damnacanthol (10) – are reported here for the first time from the genus Pentas. The compounds were identified by NMR and mass spectroscopic techniques.

Key words

Pentas longiflora - Pentas lanceolata - Rubiaceae - anthraquinone - 5,6-dihydroxydamnacanthol - pyranonaphthoquinone - malaria

References

• 1 WHO .World Malaria Report 2008. Geneva: WHO; 2008: 9
• 2 Heyneman D. The worldwide burden of parasitic disease. In: Leech J, Sande M, Root R, editors Parasitic infections. New York: Churchill Livingstone; 1988: 11-32
• 3 Wongsrichanalai C, Pickard A L, Wernsdorfer W H, Meshnick S R. Epidemiology of drug-resistant malaria.  Lancet Infect Dis. 2002;  2 209-218
• 4 Willox M L, Bodeker G. Traditional herbal medicines for malaria.  Br Med J. 2004;  329 1156-1159
• 5 Njoroge N G, Bussmann W R, Gemmill B, Newton L E, Ngumi V W. Utilisation of weed species as sources of traditional medicines in central Kenya.  Lyonia. 2004;  7 71-87
• 6 Kokwaro J O. Medicinal Plants of East Africa. Nairobi: University of Nairobi Press; 2010: 247-248
• 7 Wanyoike G N, Chhabra S C, Lang'at-Thoruwa C C, Omar S A. Brine shrimp toxicity and antiplasmodial activity of five Kenyan medicinal plants.  J Ethnopharmacol. 2004;  90 129-133
• 8 Koch A, Tamez P, Pezzuto J, Soejarto D. Evaluation of plants used for antimalarial treatment by the Massai of Kenya.  J Ethnopharmacol. 2005;  101 95-99
• 9 Nayak B S, Vinutha B, Geetha B, Sudha B. Experimental evaluation of Pentas lanceolata flowers for wound healing activity in rats.  Fitoterapia. 2005;  76 671-675
• 10 Juma W P, Akala H M, Eyase F L, Muiva L M, Heydenreich M, Okalebo F A, Gitu P M, Peter M G, Walsh D S, Imbuga M, Yenesew A. Terpurinflavone: An antiplasmodial flavone from the stem of Tephrosia Purpurea.  Phytochem Lett. 2011;  4 176-178
• 11 De Kimpe N, Van Puyvelde L, Schripsema J, Erkelens C, Verpoorte R. Complete proton and carbon-¹³NMR spectral assignments of pentalongin.  Magn Reson Chem. 1993;  31 329-330
• 12 Hari L, De Buyck L F, De Pooter H L. Naphthoquinoid pigments from Pentas longiflora.  Phytochemistry. 1991;  30 1726-1727
• 13 El Hady S, Bukuru J, Kesteleyn B, van Puyvelde L, De Kimpe N, Van T N. New pyranonaphthoquinone and pyranonaphthohydroquinone from the roots of Pentas longiflora.  J Nat Prod. 2002;  65 1377-1379
• 14 Hayashi T, Smith F T, Lee K H. Antitumor agents. 89. Psychorubrin, a new cytotoxic naphthoquinone from Psychotria rubra and its structure-activity relationships.  J Med Chem. 1987;  30 2005-2008
• 15 Liu R, Lu Y, Wu T, Pan Y. Simultaneous isolation and purification of mollugin and two anthraquinones from Rubia cordifolia by HSCCC.  Chromatographia. 2008;  68 95-99
• 16 Van T, De Kimpe N. Synthesis of pyranonaphthoquinone antibiotics involving the ring closing metathesis of a vinyl ether.  Tetrahedron Lett. 2004;  45 3443-3446
• 17 Puyvelde L V, Geysen D, Ayobangira F X, Hakizamungu E, Nshimyimana A, Kalise A. Screening of medicinal plants of Rwanda for acaricidal activity.  J Ethnopharmacol. 1985;  13 209-215
• 18 Ho L K, Don M J, Chen H C, Yeh S F, Chen J M. Inhibition of hepatitis B surface antigen secretion on human hepatoma cells. Components from Rubia cordifolia.  J Nat Prod. 1996;  59 330-333
• 19 Kusamba C, Federici E, De Vicente Y, Galeffi C. The anthraquinones of Pentas zanzibarica.  Fitoterapia. 1993;  64 18-22
• 20 Adesogan E K. Anthraquinones and anthraquinols from Morinda lucida: The biogenetic significance of oruwal and oruwalol.  Tetrahedron. 1973;  29 4099-4102
• 21 Ferrari F, Monache G D, Alves de Lima R. Two naphthopyran derivatives from Faramea cyanea.  Phytochemistry. 1985;  24 2753-2755
• 22 Koumaglo K, Gbeassor M, Nikabu O, De Souza C, Werner W. Effects of three compounds extracted from Morinda lucida on Plasmodium falciparum.  Planta Med. 1992;  58 533-534
• 23 Scott A I. Interpretation of the ultraviolet spectra of natural products. Oxford: Pergamon Press; 1964: 286-289
• 24 Schripsema J, Dagnino D. Elucidation of the substitution pattern of 9, 10-anthraquinones through the chemical shifts of peri-hydroxyl protons.  Phytochemistry. 1996;  42 177-184
• 25 Han Y S, Van der Heijen R, Verpoorte R. Biosynthesis of anthraquinones in cell cultures of Rubiaceae.  Plant Cell Tissue Organ Cult. 2001;  67 201-220
• 26 Caliş I, Tasdemir D, Ireland C M, Sticher O. Lucidin type anthraquinone glycosides from Putoria calabrica.  Chem Pharm Bull (Tokyo). 2002;  50 701-702
• 27 Gonzalez A, Barrosso J T, Cardona R J, Medina J M, Rodriguez Luis F. Química de la Rubiáceas. II. Componentes de la “Putoria calábrica” Perss.  Anales de Quimica. 1977;  73 538-545
• 28 Schripsema J, Ramos V A, Verpoorte R. Robustaquinones, novel anthraquinones from an elicited Cinchona robusta suspension culture.  Phytochemistry. 1999;  51 55-60
• 29 Leistner E. Biosynthesis of morindone and alizarin in intact plants and cell suspension cultures of Morinda citrifolia.  Phytochemistry. 1973;  12 1669-1674
• 30 Ee G C L, Wen Y P, Sukari M A, Go R, Lee H L. A new anthraquinone from Morinda citrifolia roots.  Nat Prod Res. 2009;  23 1322-1329
• 31 Osman C P, Ismail N H, Ahmad R, Ahmat N, Awang K, Jaafar F M. Anthraquinones with antiplasmodial activity from the roots of Rennellia elliptica Korth. (Rubiaceae).  Molecules. 2010;  15 7218-7226