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The antimalarial davanone in several Artemisia species

March 11, 2017 - 20:03 -- Pierre Lutgen

In Mexico eight species of Artemisia have been described and among them just Artemisia ludoviciana has been empirically used in the treatment of intermittent fever (malaria). To know whether this Mexican Artemisia had antimalarial activity several in vivo experiments were performed, on mice infected by Plasmodium yoelii yoelii, in a four-day test scheme. The results of the in vivo experiments showed that the parasite reproduction was inhibited up to 98.6% at the fifth day.

           Malagón F, Vázquez J, Delgado G, Ruiz A. Antimalaric effect of an alcoholic extract of Artemisia ludoviciana mexicana in a rodent malaria model Parasitologia. 1997 Mar;39(1):3-7.

It is worth the effort to understand why this Artemisia ludoviciana also called “Armoise de Louisiane” or “prairie sage” has strong antimalarial effects while not containing artemisinin.

The chemical composition of essential oils isolated from aerial parts of seven wild sages from Western Canada - Artemisia absinthium L., Artemisia biennis Willd., Artemisia cana Pursh, Artemisia dracunculus L., Artemisia frigida Willd., Artemisia longifolia Nutt. and Artemisia ludoviciana , was investigated by GC-MS. The oil of A. ludoviciana was also characterized by a high content of oxygenated sesquiterpenes, of which davanone (11.5%) was the main component identified. This molecule was absent in the six other Artemisia species.

           Daíse Lopes-Lutz, Daniela S. Alviano , Celuta S. Alviano, Paul P. Kolodziejczyk, Screening of chemical composition, antimicrobial and antioxidant activities of Artemisia essential oils Phytochemistry 69 (2008) 1732–1738

The name davanone stems from a Far Eastern plant, Artemisia pallens, also called davana and which has an essential oil very rich in davanone. It is an unsaturated ketonic sesquiterpene and has several isomers. It can also be present in these plants under the form of hydroxydavanone, a furanoid sequiterpene alcohol. Under this form it is found in Artemisia maritima (alias Artemisia campestris) in Northern Germany and the Ile d’Yeu in France.

           Helmut Jork, Mandfred Nachtrab, Hydroxy-Davanon, ein furanoider Sequiterpenalkohol, Neue Substanzen aus ätherischen Oelen verschiener Artemisia Species. Arch Pharm (Winheim) 1979, 312, 923-932

Artemisia maritima has antiplasmodial activities in in vivo murine trials.

           Ene Atawodi, Ameh, Kwanashie, and Agomo, P. In vivo antiplasmodial effect of chloroform extracts of Artemisia maciverae Linn and Artemisia maritima Linn. African Journal of Biotechnology Vol. 8 (23), pp. 6612-6616, 1 December, 2009

           N Valecha, S Biswas, Antimalarial activity of Artemisia maritima and Artemisia nilegarica. Indian J of Pharmacology. 1994, 26-2, 144-146.

Artemisia sieberi and Artemisia herba alba which were found by the University Al Quds (personal communication) to have a strong inhibitory effect of beta-hematin crystallization, indicative of antimalarial properties, also contain davanone or hydroxydavanone.

           L Awahibi, O Basudan, K Bolla, Sesquiterpene lactones and flavonoids from Artemisia sieberi, Int J Pharmacognosy and Phytochem Res, 2016 8(4), 639-644

           H Ben-Nasr, M Abderrahim, K Zeghal, Potential Phytotherapy use of Artemisia Plants. J Appl Pharmaceut Sc, 2013, 3(05), 120-125

           S Salido, L Valenzuela, E Cano, Composition and infraspecific variability of Artemisia herba alba from Southern Spain; Biochemical Systeatics and Ecology, 2004, 32 265-277

           Maggio A, Rosselli S, Brancazio CL, Spadaro V, Raimondo FM, Bruno M. Metabolites from the aerial parts of the Sicilian population of Artemisia alba. Nat Prod Commun. 2013 Mar;8(3):283-6.

Dichloromathane extract of A. kopetdaghensis and PE extract of A. turcomanica show remarkable anti-malarial activity with IC50 values of 1.04mg/mL and 0.90 mg/mL, respectively, compared to positive control chloroquine, IC50 0.04 mg/mL.

            M.Mojarrab, S.A. Emami, Sh. Gheibi, A.M. Taleb, F. Heshmati Afshar. Evaluation of anti-malarial activity of Artemisia turcomanica and A. kopetdaghensis by cell-free β-hematin formation assay. Research Journal of Pharmacognosy (RJP) 3(4), 2016: 59-65

Artemisia abrotanum has known antimalarial properties. In Poland they found a content of 21% of davanone in the extract.

            R Kowalski, G Zawislak, Analysis of essential oils and extracts from Artemisia abrotanum and Artemisia dracunculs. Herba Polonica. 2007, 33.3.

            B Cubukcu, D Bray, D WarhurstIn vitro antimalarial activity of crude extracts and compounds from Artemisia abrotanum . Phytomedicine, 1990, DOI: 10.1002/ptr.2650040510

Artemisia indica contains up to 30% of davanone and has known antimalarial properties.

            SZ Haider, M Mohan, H Andola, Consituents of Artemisia indica from Uttarakhand Himalaya : a source of davanone. Pharmacognosy Research, Jul-Sept 2014                       Rachada Chanphen , Yodhathai Thebtaranonth. Antimalarial Principles from Artemisia indica. J. Nat. Prod., 1998, 61 (9), pp 1146–1147 DOI: 10.1021/np980041x

Artemisia persica contains up to 60% of davanone. It is well known as antipyretic and antimalarial plant.

            Omid Sadeghpour, Gholamreza Asgharib, Mohammad Reza Shams Ardekanic. Composition of Essential Oil Pharmaceutical of Artemisia persica Boiss. from Iran. Iranian Journal of Research (2004) 3: 65-67

Artemisia turanica contains 19.3 % davanone in its essential oil. A study from Iran confirmed antimalarial effects of A. turanica extracts against murine malaria in vivo during early infection. There are more benefits on pathophysiological symptoms by this medication than for classical antimalarials like chloroquine or Fansidar which cause side-effects.

            Ali Firouznia , Mohammad Taghi Akbari , Abdolhossein Rustaiyan , Shiva Masoudi , Mohsen Bigdeli & Maryam Tabatabaei Anaraki. Composition of the Essential oils of Artemisia turanica Krasch., Helichrysum oocephalum Boiss. and Centaurea ispahanica Boiss. Three Asteraceae Herbs Growing Wild in Iran. J Essential Oil bearing Plants, 2007, 10-2,Pages: 88-93

            Mahboubeh Taherkhani, Abdolhossein Rustaiyan, Hossein Nahrevanian, Comparison of antimalarial activity of Artemisia turanica extract withcurrent drugs in vivo. J Vector Borne Dis 50, March 2013, pp. 51–56 Davanone has antimicrobial and antifungal properties V Vasj, M Sokov, S Milosaivleji.

            Antifungal activity of davanone-type sesquiterpenes from Artemisia lobelii J. Serb. Chem. Soc. 69 (11) 969–972 (2004) UDC 582.998.2:615.281/.282

Davanone showed no toxicity in murine tests.

            Oser BG, Carson S, Toxicological tests of flavouring maters. Fd Cosmetic Toxicol, 195, 3, 563.

The best explanation for the antimalarial activity of davanone can be found in a thesis from Cape Town University. It contributes also to the understanding of the strong antimalarial properties of Artemisia afra. The fraction of the extract containing hydroxydavanone had an IC 50 of 0.5 microg/ml against the D10 chloroquine-sensitive strain and the same against the FAC8 chloroquine-resistant strain. The antimalarial properties were lower for plant samples collected after the flowering period

            Meryl A Abrahams. Bio-assay guides fractionation of Artemisia afra for in vitro antimalarial activity against Plasmodium falciparum. PhD Thesis Cape Town University, 1966.

This remains evidently an open research field. Some results from the literature seem to support the important role of davanone against parasites. An in vitro trial in Ethiopia showed that Artemisia absinthium had stronger antitrypanosomal properties than Artemisia annua. The essential oil of Artemisia absinthium contained 6.7 % of davanone and Artemisia annua none.

            E Nibret, M Wink, Volatile components of four Ethiopian Artemisia species extracts and their antitrypanosomal and cytotoxic activities. Phytomedicine, 2010 Apr;17(5):369-74. doi: 10.1016/j.phymed.2009.07.016.

Another element in support of the davanone antimalarial hypothesis is the fact theat Lantana camara which contains up to 15% of davanone is used in many countries as antimalarial plant.

            Carrillo-Rosario T, Diaz de Ramirez A. Actividad antimalarica de extractos de Camara lantana en ratones infectados. Revista de la Facultad de Farmacia 2006 vol 48(1).

            E Omoregie, I Aliyu, K Folashade. Chemical components of the essential oil of Lantana Camara in Nigeria. Am Chem Soc J, 2016, 12(1), 1-7.

            V Ranpariya, S Parmar, R sheth, Antiplasmodial activity of Lantana caamara in mice. Brit J Pharm Res, 2016, 13(4) 1-8

            Gabi Baba, A Adewumi, VO Aina, Phytochemical characterization and in vivo anti-malaria activity of Lantana camara leaf