Abstract
This article reports for the first time the antibacterial, antifungal, antioxidant and anticancer activities of vilangin synthesised from embelin isolated from Embelia ribes berries. E. ribes is widely used as traditional herbal medicine in India. E. ribes is used as appetiser, carminative, anthelmintic, alexiteric, laxative and alterative. This plant is also used to treat tumour, ascites, bronchitis, mental diseases, dyspnoea, heart diseases, urinary discharges, jaundice, hemicrania, and worms in wounds. Here the major compound, embelin, was isolated from the fruits of E. ribes. Vilangin was synthesised by condensation of embelin with formaldehyde in acetic acid solution. The biological activity of vilangin is unknown so far. Hence, we studied antibacterial, antifungal, antioxidant and anticancer activities of vilangin. The minimum inhibitory concentration value of vilangin was 62.5 μg/mL against Staphylococcus epidermidis and Salmonella typhimurium. The radical scavenging activity was maximum at 1,000 μg/mL. Ferric reducing antioxidant power assay of vilangin showed a twofold higher value compared to the standard. Vilangin showed 61.95 % of cytotoxic activity in vitro against A549 lung adenocarcinoma cancer cell line at a dose of 500 μg/mL with half-maximal inhibitory concentration (IC50) of 400 μg/mL. Vilangin can thus be further tested as a new drug.
Similar content being viewed by others
References
Anonymous (2005) Compendium of medicinal plants. National Institute of Industrial Research, Kamalanagar, New Delhi, India, pp 110–113
Balachandran C, Duraipandiyan V, Al-Harbi NA, Balakrishna K, Kalia NP, Rajput VS, Khan IA, Ignacimuthu S (2012a) Antimicrobial and antimycobacterial activities of methyl caffeate isolated from Solanum torvum swartz Fruit. Indian J Microbiol 52:676–681
Balachandran C, Duraipandiyan V, Ignacimuthu S (2012b) Cytotoxic (A549) and antimicrobial effects of Methylobacterium sp. isolate (ERI-135) from Nilgiris forest soil, India. Asian Pac J Trop Biomed 2:712–716
Bheemasankara Rao CH, Venkateswarlu V (1961) Chemical examination of Embelia ribes. I. Isolation of a new constituent, “Vilangin” constitution and synthesis. J Org Chem 26:4529–4532
Chitra M, Sukumar E, Suja V, Devi CS (1994) Antitumor, anti-inflammatory and analgesic property of embelin, a plant product. Exp Chemother 40:109–113
Chitra M, Devi CS, Sukumar E (2003) Antibacterial activity of embelin. Fitoterapia 74:401–403
Chitra M, Devi CS, Sukumar E (2004) Effect of embelin on carbohydrate moieties of glycoprotein in tumor bearing rats. J Nat Rem 4:77–80
Clinical and Laboratory Standards Institute (CLSI) (2008) Reference method for broth dilution antifungal susceptibility testing of filamentous fungi; approved standard second edition. CLSI document M38-A2 (ISBN 1-56238-668-9). Clinical and laboratory standards institute, 940, West valley Road, Suite 1400, Wayne, Pennsylvania 19087-1898 USA
Dail Y, DeSano J, Qu Y, Tang W, Meng y, Lawrence TS, Xu L (2011) Natural IAP inhibitor embelin enhances therapeutic efficacy of ionizing radiation in prostate cancer. Am J Cancer Res 1:128–143
Duraipandiyan V, Ignacimuthu S (2009) Antibacterial and antifungal activity of flindersine isolated from the traditional medicinal plant, Toddalia asiatica (L.) Lam. J Ethnopharmacol 123:494–498
Gupta R, Sharma AK, Sharma MC, Gupta RS (2012) Antioxidant activity and protection of pancreatic β-cells by embelin in streptozotocin-induced diabetes. J Diabetes 4:248–256
Halvorsen BL, Holte K, Myhrstad MCW, Barikmo I, Hvattum E, Remberg SF et al (2002) A systematic screening of total antioxidants in dietary plants. J Nutr 132:461–471
Jayaprakasha GK, Girennavar B, Patil BS (2008) Radical scavenging activities of rio red grapefruits and sour orange fruit extracts in different in vitro model systems. Bioresour Technol 99:4484–4494
Johri RK, Pahwa GS, Sharma SC, Zutshi U (1991) Determination of estrogenic/antiestrogenic potential of antifertility substances using rat uterine peroxidise assay. Contraception 44:549–557
Joshi R, Kamat JP, Mukherjee T (2007) Free radical scavenging reactions and antioxidant activity of embelin: biochemical and pulse radiolytic studies. Chem Biol Interact 167:125–134
Khan MA, Naidu MA, Akbar Z (2010) In-vitro antimicrobial activity of fruits extract of Embelia ribes Burm. Int J Pharm Bio Arch 1:267–270
Kirtikar KR, Basu BD (2006) Indian Medicinal Plants (vol 2), In: Blatter E, Caius JF, Mhaskar KS (ed), 2nd edn. Bishen Singh, Mahendrapal Singh, New Connaught Place, Dehra Dun, India, pp 1477–1481
Kubola J, Siriamornpun S (2011) Phytochemicals and antioxidant activity of different fruit fractions (peel, pulp, aril and seed) of thai gac (Momordica cochinchinensis spreng). Food Chem 127:1138–1145
Nadkarni AK, Nadkarni’s (2007) Indian materia medica. Popular Prakashan Pvt Ltd. Mumbai, India 1: 478
NCCLS (2002) M27-A2. In National committee for clinical laboratory standards. Reference method for broth dilution antifungal susceptibility testing of yeasts: proposed standard
Prieto P, Pineda M, Aguilar M (1999) Spectrophotometric quantitation of antioxidant capacity through the formation of a phosphor molybdenum complex: specific application to the determination of vitamin E. Anal Biochem 269:337–341
Radhakrishnan N, Gnanamani A, Mandal AB (2011) A potential antibacterial agent Embelin, a natural benzoquinone extracted from Embelia ribes. Bio Med 3:1–7
Rathinam K, Santhakumari Ramiah G, Ramiah N (1976) Studies on the antifertility activity of embelin. J Res Ind Med 11:84–90
Schlesier K, Harwat M, Böhm V, Bitsch R (2002) Assessment of antioxidant activity by using different in vitro methods. Free Radical Res 36:177–178
Shankarmurthy K, Krishna V, Maruthi KR, Rahiman BA (2004) Rapid adventitious organogenesis from leaf segments of Embelia ribes Burm. A Threatened Medicinal Plant. Taiwania 49:194–200
Siegelin MD, Gaiser T, Siegelin Y (2009) The XIAP inhibitor embelin enhances TRAIL-mediated apoptosis in malignant glioma cells by down-regulation of the short isoform of FLIP. Neurochem Int 55:423–430
Srinivas K (2010) Anticancer and antimicrobial activity of embelin derivatives. Int J Preclin Pharm Res 1:35–38
Suthar M, Patel R, Hapani K, Patel K (2009) Screening of Embelia ribes for antifungal Activity. Int J Pharm Sci Drug Res 1:203–206
Wang X, Li X (2011) Evaluation of antioxidant activity of isoferulic acid in vitro. Nat Prod Commun 6:1285–1288
Warrier PK, Nambiar VPK, Ganapathy PM (2001) Some important medicinal plants of the Western Ghats, India: a profile. international development research centre (IDRC), Canada pp 139–156
Acknowledgments
We are grateful to Entomology Research Institute for financial assistance.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Balachandran, C., Duraipandiyan, V., Balakrishna, K. et al. Synthesis and medicinal properties of plant-derived vilangin. Environ Chem Lett 11, 303–308 (2013). https://doi.org/10.1007/s10311-013-0408-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10311-013-0408-4