MENU

Anti-Japanese Encephalitis Virus (JEV) Activity of Triterpenes and Flavonoids from Euphorbia hirta

Wilanfranco C. Tayone1*, Kotaro Ishida2, Simon Goto2, Janeth C. Tayone1,
Masashi Arakawa2, Eiji Morita2, and Masaru Hashimoto2

1Institute of Agriculture and Life Sciences, Davao Oriental State
College of Science and Technology, City of Mati 8200 Philippines
2Faculty of Agriculture and Life Science, Hirosaki University
Hirosaki-shi, Aomori-ken 036-8560 Japan

*Corresponding Author: This email address is being protected from spambots. You need JavaScript enabled to view it.

 

ABSTRACT

Chemical investigation of Euphorbia hirta, a folkloric medicinal plant against dengue in the Philippines, disclosed two known flavonoids (quercetrin and myricitrin) together with seven known triterpenes (taraxerone, taraxerol, β-sitosterol, 24-hydroperoxycycloart-25-en-3β-ol, 25-hydroperoxycycloart-23-en-3β-ol, lupeol, and (23E)-cycloart-23-en-3β, 25-diol). The structures were established mainly with 1H and 13C nuclear magnetic resonance (NMR) spectroscopic analyses in comparison with the literature data. These compounds were tested against Japanese encephalitis virus (JEV). Results showed that myricitrin exhibited good inhibition on the production of the infectious viral particle at 100 µM.

 

 

REFERENCES

ADEDAPO AA, SHABI OO, ADEDOKUN OA. 2005. Anthelmintic efficacy of the aqueous crude extract of Euphorbia hirta Linn in Nigerian dogs. Veterinarski Arhiv 75(1): 39–47.
BONNER TG, MCNAMARA P. 1968. The pyridine-catalysed acetylation of phenols and alcohols by acetic anhydride. Journal of the Chemical Society B: Physical Organic (0): 795–797.
CHAIYADEJ K, WONGTHAP H, VADHANAVIKIT S, CHANTRAPROMMA K. 2004. Bioactive constituents from the twigs of Sonneratia alba. Walailak Journal of Science and Technology 1(1): 15–22.
CHATURVEDULA VSP, PRAKASH I. 2012. Isolation of stigmasterol and β-sitosterol from the dichloromethane extract of Rubus suavissimus. International Current Pharmaceutical Journal 1(9): 239–242.
CHEN YS, ER HM. 2010. Antioxidant, anti-proliferative and bronchodilatory activities of Euphorbia hirta extracts. Malaysian Journal of Science 29(1): 22–29.
DOMITROVIĆ R, RASHED K, CVIJANOVIĆ O, KNEŽEVIĆ SV, ŠKODA M, VIŠNIĆ A. 2015. Myricitrin exhibits antioxidant, anti-inflammatory and antifibrotic activity in carbon tetrachloride-intoxicated mice. Chemico-Biological Interactions 230: 21–29.
EKPO OE, PRETORIUS E. 2007. Asthma, Euphorbia hirta and its anti-inflammatory properties. South African Journal of Science 103: 201–203.
FENG Z, WANG Y, ZHANG P. 2005. The chemical constituents of Rhododendron ovatum Planch. Acta Pharmaceutica Sinica 40(2): 150–152.
GALVEZ J, ZARZUELO A, CRESPO ME, LORENTE MD, OCETE MA, JIMÉNEZ J. 1993. Antidiarrhoeic activity of Euphorbia hirta extract and isolation of an active flavonoid constituent. Planta Medica 59(4): 333–336.
GYURIS A, SZLÁVIK L, MINÁROVITS J, VASAS A, MOLNÁR J, HOHMANN H. 2009. Antiviral activities of extracts of Euphorbia hirta L. against HIV-1, HIV-2 and SIVmac251. In Vivo 23(3): 429–432.
JAMAL AK, YAACOB WA, DIN LB. 2009. Triterpenes from the root bark of Phyllanthus columnaris. Australian Journal of Basic and Applied Sciences 3(2): 1428–1431.
JOHARI J, KIANMEHR A, MUSTAFA MR, ABUBAKAR S, ZANDI K. 2012. Antiviral activity of baicalein and quercetin against the japanese encephalitis virus. International Journal of Molecular Sciences 13(12): 16785–16795.
JOHNSON PB, ABDURAHMAN EM, TIAM EA, ABDU-AGUYE I, HUSSAINI IM. 1999. Euphorbia hirta leaf extracts increase urine output and electrolytes in rats. Journal of Ethnopharmacology 65(1): 63–69.
KATO T, FREI B, HEINRICH M, STICHER O. 1996. Antibacterial hydroperoxysterols from Xanthosoma robustum. Phytochemistry 41(4): 1191–1195.
[Kew] Royal Botanic Gardens. n/d. Euphorbia hirta L. Retrieved on 14 Apr 2020 from http://plantsoftheworldonline.org/taxon/urn:lsid:ipni.org:names:101651-2#image-gallery
KUMAR S, RASHMI N, KUMAR D. 2010. Evaluation of antidiabetic activity of Euphorbia hirta Linn in streptozotocin induced diabetic mice. Indian Journal of Natural Products and Resources 1(2): 200–203.
LANHERS MC, FLEURENTIN J, CABALION P, ROLLAND A, DORFMAN P, MISSLIN R, PELT JM. 1990. Behavioural effects of Euphorbia hirta L.: sedative and anxiolytic properties. Journal of Ethnopharmacology 29(2): 189–198.
LEE KH, CHEN YS, JUDSON JP, CHAKRAVARTHI S, SIM YM, ER HM. 2008. The effect of water extracts of Euphorbia hirta on cartilage degeneration in arthritic rats. The Malaysian Journal of Pathology 30(2): 95–102.
LEI Y. 2017. Myricitrin decreases traumatic injury of the spinal cord and exhibits antioxidant and anti‑inflammatory activities in a rat model via inhibition of COX‑2, TGF‑β1, p53 and elevation of Bcl‑2/Bax signaling pathway. Molecular Medicine Reports 16(5): 7699–7705.
LIU Q, CHEN CJ, SHI X, ZHANG L, CHEN HJ, GAO K. 2010. Chemical constituents from Aphanamixis grandifolia. Chemical and Pharmaceutical Bulletin 58(11): 1431–1435.
LIU Y, MURAKAMI N, JI H, ABREU P, ZHANG S. 2007. Antimalarial flavonol glycosides from Euphorbia hirta. Pharmaceutical Biology 45(4): 278–281.
NI JC, SHI JT, TAN QW, CHEN QJ. 2017. Phenylpropionamides, piperidine, and phenolic derivatives from the fruit of Ailanthus altissima. Molecules 22: 1–12.
OGBULIE JN, OGUEKE CC, OKOLI IC, ANYANWU BN. 2007. Antibacterial activities and toxicological potentials of crude ethanolic extracts of Euphorbia hirta. African Journal of Biotechnology 6(13): 1544–1548.
PATIL SB, MAGDUM CS. 2011. Phytochemical investigation and antitumour activity of Euphorbia hirta Linn. European Journal of Experimental Biology 1(1): 51–56.
PATIL SB, NAIKWADE NS, MAGDUM CS. 2009. Review on phytochemistry and pharmacological aspects of Euphorbia hirta Linn. Journal of Pharmaceutical Research and Health Care 1(1): 113–133.
RAGASA CY, CORNELIO KB. 2013. Triterpenes from Euphorbia hirta and their cytotoxicity. Chinese Journal of Natural Medicines 11(5): 528–533.
RAO KVB, KARTHIK L, ELUMALAI EK, SRINIVASAN K, KUMAR G. 2010. Antibacterial and antifungal activity of Euphorbia hirta L. leaves: a comparative study. Journal of Pharmacy Research 3: 548–549.
SCHWINN MK, MACHLEIDT T, ZIMMERMAN K, EGGERS CT, DIXON AS, HURST R, HALL MP, ENCELL LP, BINKOWSKI BF, WOOD KV. 2018. CRISPR – mediated tagging of endogenous proteins with a luminescent peptide. ACS Chemical Biology 13(2): 467–474.
SENCKENBERG. n/d. West African plants: a photo guide. Euphorbia hirta L. Retrieved on 14 Apr 2020 from http://www.westafricanplants.senckenberg.de/root/index.php?page_id=14&id=688#
SEO C, AHN EK, KANG JS, LEE JH, OH JS, HONG SS. 2017. Excavasides A and B, two new flavonoid glycosides from Clausena excavata Burm. f. (Rutaceae). Phytochemistry Letters 20: 93–97.
SHIH MF, CHENG YD, SHEN CR, CHENG JY. 2010. 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. Journal of Natural Medicines 64(3): 330–335.
SIDAMBARAM RR, DINESH MG, JAYALAKSHMI ET. 2011. An in vitro study of cytotoxic activity of Euphorbia hirta on Hep-2 cells of human epithelioma of larynx. International Journal of Pharmacy and Pharmaceutical Sciences 3(3): 101–103.
SINGH GD, KAISER P, YOUSSOUF MS, SINGH S, KHAJURIA A, KOUL A, BANI S, KAPAHI BK, SATTI NK, SURI KA, JOHRI RK. 2006. Inhibition of early and late phase allergic reactions by Euphorbia hirta L. Phytotherapy Research 20(4): 316–321.
TAMURA T, FUKUHARA T, UCHIDA T, ONO C, MORI H, SATO A, FAUZYAH Y, OKAMOTO T, KUROSU T, SETOH YX, IMAMURA M, TAUTZ N, SAKODA Y, KHROMYKH AA, CHAYAMA K, MATSUURA Y. 2018. Characterization of recombinant flaviviridae viruses possessing a small reporter tag. Journal of Virology 92(2): 1–19.
TAYONE WC, TAYONE JC, HASHIMOTO M. 2014. Isolation and structure elucidation of potential anti-dengue metabolites from tawa-tawa (Euphorbia hirta Linn.). Walailak Journal of Science and Technology 11(10): 825–832.
VALADÃO ALC, AGUIAR RS, DE ARRUDA LB. 2016. Interplay between Inflammation and cellular stress triggered by flaviviridae viruses. Frontiers in Microbiology 7: 1–19.
WILLIAMS LAD, WILLIAMS MG, SAJABI A, BARTON EN, FLEISCHHACKER R. 1997. Angiotensin converting enzyme inhibiting and anti‐dipsogenic activities of Euphorbia hirta extracts. Phytotherapy Research 11(5): 401–402.
ZHANG Y, WANG Z, CHEN H, CHEN Z, TIAN Y. 2014. Antioxidants: potential antiviral agents for japanese encephalitis virus infection. International Journal of Infectious Diseases 24: 30–36.