Isolation and Structure Elucidation of Potential Anti-Dengue Metabolites from Tawa-tawa (Euphorbia hirta Linn.)

Wilanfranco Caballero TAYONE, Janeth Cuevas TAYONE, Masaru HASHIMOTO


Many natural products found in plants exhibit a variety of biological activities including antibiotic, antitumor, and antiviral activities that have been utilized in the medicinal field to cure millions of people from serious diseases. Euphorbia hirta Linn. herb, a folkloric medicinal plant in the Philippines against dengue is reportedly effective against the dengue virus. This deadly and painful mosquito-born disease continuously affects millions of people worldwide for there are no commercially developed drugs or vaccines available. From the viewpoint of overcoming the dengue disease, the authors investigated the chemical components of Euphorbia hirta Linn. Preliminary anti-dengue assay by Plaque Reduction Neutralization Test (PRNT) revealed that the ethyl acetate layer was the most active fraction and significantly reduced the plaque forming capacity of the dengue virus serotypes 1 and 2 relative to the control. Further purification of the active ethyl acetate fraction afforded 6 known triterpene and 3 flavonoid compounds. The planar structures of these molecules were established by ESIMS and NMR spectroscopic analyses.



Tawa-tawa, nuclear magnetic resonance, structure elucidation, chromatography, dengue

Full Text:



DJ Newman and GM Cragg. Natural products as sources of new drugs over the last 25 years. J. Nat. Prod. 2007; 70, 461-77.

NM Parcon. Preparation of thin layer chromatography profile of extracts from Euphorbia hirta, Linn. Agham Mindanaw 2006; 3, 73-7.

JN Ogbulie, CC Ogueke, IC Okoli and BN Anyanwu. Antibacterial activities and toxicological potentials of crude ethanolic extracts of Euphorbia hirta. Afr. J. Biotechnol. 2007; 6, 1544-8.

PB Johnson, EM Abdurahman, EA Tiam, I Abdu-Aguye and IM Hussaini. Euphorbia hirta leaf extracts increase urine output and electrolytes in rats. J. Ethnopharmacol. 1999; 65, 63-9.

GD Singh, P Kaiser, MS Youssouf, S Singh, A Khajuria, A Koul, S Bani, BK Kapahi, NK Satti, KA Suri and RK Johri. Inhibition of early and late phase allergic reactions by Euphorbia hirta L. Phytother. Res. 2006; 20, 316-21.

AA Adedapo, OO Shabi and OA Adedokun. Anthelmintic efficacy of the aqueous crude extract of Euphorbia hirta Linn in Nigerian dogs. Vet. Arhiv. 2005; 75, 39-47.

LAD Williams, MG Williams, A Sajabi, EN Barton and R Fleischhacker. Angiotensin converting enzyme inhibiting and anti-dipsogenic activities of Euphorbia hirta extracts. Phytother. Res. 1997; 11, 401-2.

MG Ladthers, J Fleumntin, F Mortier, R Misslin, P Cabalion. Behavioral and neurotropic effects of an aqueous extract of Euphorbia hirta L. In: Proceedings of the Actes du 2e Colloque Européen d'Ethnophmacologie et de la 1 le Conférence Internationale d'Ethnomédecine, Heidelberg, Germany, 1993, p. 24-7.

J Galvez, A Zarzuelo, ME Crespo, MD Lorente, MA Ocete and J Jiménez. Antidiarrhoeic activity of Euphorbia hirta extract and isolation of an active flavonoid constituent. Planta Med. 1993; 59, 333-6.

KVB Rao, L Karthik, EK Elumalai, K Srinivasan and G Kumar. Antibacterial and antifungal activity of Euphorbia hirta l. Leaves: A comparative study. J. Pharm. Res. 2010; 3, 548-9.

Y Liu, N Murakami, H Ji, P Abreu and S Zhang. Antimalarial Flavonol Glycosides from Euphorbia hirta. Pharm. Biol. 2007; 45, 278-81.

YS Chen and HM Er. Antioxidant, anti-proliferative and bronchodilatory activities of Euphorbia hirta extracts. Malays. J. Sci. 2010; 29, 22-9.

S Kumar, R Kumar and D Kumar. Evaluation of antidiabetic activity of Euphobia hirta Linn. in streptozotocin-induced diabetic mice. Indian J. Nat. Prod. Resour. 2010; 12, 200-3.

RR Sidambaram, MG Dinesh and ET Jayalakshmi. An in vitro study of cytotoxic activity of Euphorbia hirta on HEP-2 cells of human epithelioma of larynx. Int. J. Pharm. Pharm. Sci. 2011; 3, 101­3.

KH Lee, YS Chen, JP Judson, S Chakravarthi, YM Sim and HM Er. The effect of water extracts of Euphorbia hirta on cartilage degeneration in arthritic rats. Malays. J. Pathol. 2008; 30; 95-102.

MF Shih, YD Cheng, CR Shen and JY Cherng. A molecular pharmacology study into the anti-inflammatory actions of Euphorbia hirta L. on the LPS-induced RAW 264.7 cells through selective iNOS protein inhibition. J. Nat. Med. 2010; 64, 330-5.

SB Patil and CS Magdum. Phytochemical investigation and antitumour activity of Euphorbia hirta Linn. Eur. J. Exp. Bio. 2011; 1, 51-6.

A Gyuris, L Szlávik, J Minárovits, A Vasas, J Molnár and Hohmann. Antiviral activities of extracts of Euphorbia hirta L. against HIV-1, HIV-2 and SIVmac251. In Vivo 2009; 23, 429-32.

AK Jamal, WA Yaacob and LB Din. Triterpenes from the root bark of Phyllanthus Columnaris. Aust. J. Basic Appl. Sci. 2009, 3, 1428-31.

K Chaiyadej, H Wongthap, S Vadhanavikit and K Chantrapromma. Bioactive constituents from the twigs of Sonneratia alba. Walailak J. Sci. & Tech. 2004; 1, 15-22.

EJ Corey, SPT Matsuda and B Bartel. Isolation of an Arabidopsis thaliana gene encoding cycloartenol synthase by functional expression in a yeast mutant lacking lanosterol synthase by the use of a chromatographic screen. Proc. Natl. Acad. Sci. 1993; 90, 11628-32.

J Vincken, L Heng, A de Groot and H Gruppen. Saponins, classification and occurrence in the plant kingdom. Phytochemistry 2007; 68, 275-97.

H Sun, W Fang, W Wang and C Hu. Structure-activity relationships of oleanane- and ursane-type triterpenoids. Botanical Studies 2006; 47, 339-68.

J Liu. Pharmacology of oleanolic acid and ursolic acid. J. Ethnopharmacol. 1995; 49, 57-68.

Z Feng, Y Wang and P Zhang. The chemical constituents of Rhododendron ovatum Planch. Acta Pharmaceut. Sinic 2005; 40, 150-2.

MS Ali, M Saleem, W Ahmad, M Parvez and R Yamdagni. A chlorinated monoterpene ketone, acylated β-sitosterol glycosides and a flavanone glycoside from Mentha longifolia (Lamiaceae). Phytochemistry 2002; 59, 889-95.

W De-Eknamkul and B Potduang. Biosynthesis of β-sitosterol and stigmasterol in Croton sublyratus proceeds via a mixed origin of isoprene units. Phytochemistry 2003; 62, 389-98.

K Bock and C Pedersen. Advances in Carbohydrate Chemistry and Biochemistry. Vol 41, Academic Press, New York, 1983, p. 1-27.

T Fossen, A Larsen, BT Kiremire and O Andersen. Flavonoids from blue flowers of Nymphaèa caerulea. Phytochemistry 1999; 51, 1133-7.


  • There are currently no refbacks.

Online ISSN: 2228-835X

Last updated: 12 August 2019