Download PDF
Planta Med 2012; 78(1): 31-35
DOI: 10.1055/s-0031-1280179
Biological and Pharmacological Activity
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Antiplasmodial Quinones from Pentas longiflora and Pentas lanceolata

Milkyas Endale1 , John Patrick Alao2 , Hoseah M. Akala3 , Nelson K. Rono1 , Fredrick L. Eyase3 , Solomon Derese1 , Albert Ndakala1 , Martin Mbugua1 , Douglas S. Walsh3 , Per Sunnerhagen2 , Mate Erdelyi4 , Abiy Yenesew1
  • 1Department of Chemistry, University of Nairobi, Nairobi, Kenya
  • 2Department of Cell- and Molecular Biology, University of Gothenburg, Gothenburg, Sweden
  • 3United States Army Medical Research Unit-Kenya, MRU 64109, APO, AE 09831-4109, USA
  • 4Department of Chemistry, University of Gothenburg, Sweden, and the Swedish NMR Centre, University of Gothenburg, Gothenburg, Sweden
Further Information

Publication History

received February 19, 2011 revised July 21, 2011

accepted July 25, 2011

Publication Date:
06 October 2011 (online)

Also available at
    Permissions and Reprints

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

Supporting Information

References

  • 1 WHO .World Malaria Report 2008. Geneva: WHO; 2008: 9
    Search in Google Scholar
  • 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
    Search in Google Scholar
  • 3 Wongsrichanalai C, Pickard A L, Wernsdorfer W H, Meshnick S R. Epidemiology of drug-resistant malaria.  Lancet Infect Dis. 2002;  2 209-218
    CrossrefPubMedSearch in Google Scholar
  • 4 Willox M L, Bodeker G. Traditional herbal medicines for malaria.  Br Med J. 2004;  329 1156-1159
    CrossrefPubMedSearch in Google Scholar
  • 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
    PubMedSearch in Google Scholar
  • 6 Kokwaro J O. Medicinal Plants of East Africa. Nairobi: University of Nairobi Press; 2010: 247-248
    Search in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 12 Hari L, De Buyck L F, De Pooter H L. Naphthoquinoid pigments from Pentas longiflora.  Phytochemistry. 1991;  30 1726-1727
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 19 Kusamba C, Federici E, De Vicente Y, Galeffi C. The anthraquinones of Pentas zanzibarica.  Fitoterapia. 1993;  64 18-22
    PubMedSearch in Google Scholar
  • 20 Adesogan E K. Anthraquinones and anthraquinols from Morinda lucida: The biogenetic significance of oruwal and oruwalol.  Tetrahedron. 1973;  29 4099-4102
    CrossrefPubMedSearch in Google Scholar
  • 21 Ferrari F, Monache G D, Alves de Lima R. Two naphthopyran derivatives from Faramea cyanea.  Phytochemistry. 1985;  24 2753-2755
    CrossrefPubMedSearch in Google Scholar
  • 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
    Thieme ConnectPubMedSearch in Google Scholar
  • 23 Scott A I. Interpretation of the ultraviolet spectra of natural products. Oxford: Pergamon Press; 1964: 286-289
    Search in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    PubMedSearch in Google Scholar
  • 28 Schripsema J, Ramos V A, Verpoorte R. Robustaquinones, novel anthraquinones from an elicited Cinchona robusta suspension culture.  Phytochemistry. 1999;  51 55-60
    CrossrefPubMedSearch in Google Scholar
  • 29 Leistner E. Biosynthesis of morindone and alizarin in intact plants and cell suspension cultures of Morinda citrifolia.  Phytochemistry. 1973;  12 1669-1674
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar

Abiy Yenesew

Department of Chemistry
University of Nairobi

Chiromo Road

30197-00100 Nairobi

Kenya

Phone: +254 20 24 44 61 38

Fax: +254 20 24 44 61 38

Email: ayenesew@uonbi.ac.ke

Mate Erdelyi

Department of Chemistry
University of Gothenburg

Kemivägen 10

413 23 Gothenburg

Sweden

Phone: +46 317 86 90 33

Fax: +46 317 72 13 94

Email: mate@chem.gu.se