Terpenoids and phytosteroids isolated from Commelina benghalensis Linn. with antioxidant activity
-
Amina Khatun
,
Mahmudur Rahman
,
Mohammad Sharifur Rahman
Abstract
Background
Commelina benghalensis Linn. (Family: Commelinaceae) is a common weed available in Bangladesh with several uses in traditional medicine. However, the chemical profile of this medicinal plant is scarce in relation to its medicinal uses. The aerial parts of this plant have been investigated for the isolation of secondary metabolites and evaluation of the biological activities.
Methods
Major phytochemical groups were analyzed using chromogenic reagents, whereas n-hexane soluble fractionates of the methanol extract were subjected to 1H nuclear magnetic resonance (NMR) spectroscopic analysis. The antioxidant property of the obtained compounds was evaluated using 1,1-diphenyl-2-picryl-hydrazyl (DPPH).
Results
Dammara-12-en-3-one (CB-1), stigmasterol (CB-2) and 3 (2,3,4,5,6-pentahydroxy)-cinnamoyl dammara-12-ene (CB-3) were isolated from the n-hexane fractionate of methanol extract of C. benghalensis. In the study of DPPH radical scavenging activity, IC50 values were predicted to be 790.18, 4186.94 and 2001.16 μg/mL for CB-1, CB-2 and CB-3, respectively, whereas standard ascorbic acid showed IC50 at 1.26 μg/mL.
Conclusions
Two new dammarane-type triterpene (CB-1 and CB-3) and one phytosterol (CB-2) were identified in C. benghalensis with mild antioxidant property.
Acknowledgments
The authors thank the Chemical Research Division, Bangladesh Council for Scientific and Industrial Research (BCSIR) for assisting with the NMR analysis of our samples. Thanks also go to the authority of Bangladesh National Herbarium for identifying the plant and letting us use their library.
Research funding: None declared.
Author contributions: All authors have accepted responsibility for the entire content of this manuscript and approved its submission.
Competing interest: Authors state no conflict of interest.
References
[1] Ahmed N. Wild flowers of Bangladesh. Dhaka: University Press Ltd., 1997.Search in Google Scholar
[2] Ghani A. Medicinal plants of Bangladesh: chemical constituents and uses. Dhaka: Asiatic Society of Bangladesh, 1998.Search in Google Scholar
[3] Hooker J. The flora of British India, vol. iv. London: L. Reeve. 1875–97, 1961.10.5962/bhl.title.54393Search in Google Scholar
[4] Khan MAA, Islam MT, Rahman MA, Ahsan Q. Antibacterial activity of different fractions of Commelina benghalensis L. Der Pharmacia Sinica 2011;2:320–6.Search in Google Scholar
[5] Raqibul Hasan SM, Hossain MM, Akter R, Jamila M, Mazumder EH, Rahman S. Sedative and anxiolytic effects of different fractions of the Commelina benghalensis Linn. Drug Discov Ther 2009;3:221–7.Search in Google Scholar
[6] Mbazima VG, Mokgotho MP, February F, Rees DJ, Mampuru LJ. Alteration of Bax-to-Bcl-2 ratio modulates the anticancer activity of methanolic extract of Commelina benghalensis (Commelinaceae) in Jurkat T cells. Afr J Biotechnol 2008;7:3569–76.Search in Google Scholar
[7] Khatun A, Rahman M, Haque T, Rahman MM, Akter M, Akter S, et al. Cytotoxicity potentials of eleven Bangladeshi medicinal plants. Sci World J 2014;2014:7.10.1155/2014/913127Search in Google Scholar PubMed PubMed Central
[8] Khatun A, Rahman M, Jahan S. Preliminary phytochemical, cytotoxic, thrombolytic and antioxidant activities of the methanol extract of Murraya exotica Linn. leaves. Orient Pharm Exp Med 2014;14:223–9.10.1007/s13596-014-0150-xSearch in Google Scholar
[9] Evans W. Trease and Evan’s textbook of pharmacognosy. New York: Cambridge University Press, 1989.Search in Google Scholar
[10] Ahmed F, Rahman MS, Al-Mansur MA, Rashid MA. Triterpenoids and steroid from the leaves of Callistemon citrinus (Curtis.). Dhaka Univ J Pharm Sci 2016;15:1–5.10.3329/dujps.v15i1.29185Search in Google Scholar
[11] Khatun A, Rahman M, Rahman MM, Hossain H, Jahan IA, Nesa ML. Antioxidant, antinociceptive and CNS activities of Viscum orientale and high sensitive quantification of bioactive polyphenols by UPLC. Front Pharmacol 2016;7:176.10.3389/fphar.2016.00176Search in Google Scholar PubMed PubMed Central
[12] Siddiqui B, Ilyas F, Rasheed M, Begum S. Chemical constituents of leaves and stem bark of Plumeria obtusa. Phytochemistry 2014;65:2077–84.10.1016/j.phytochem.2004.04.024Search in Google Scholar PubMed
[13] Sufian MA, Begum F, Haque MR, Hasan CM, Rashid MA. Sterol and triterpenoids from Hygrophila schulli Buch.-Ham. Bangl J Bot 2015;44:319–21.10.3329/bjb.v44i2.38523Search in Google Scholar
[14] Rashid MA. Phytochemical studies in Eriostemenae. Glasgow, UK: University of Strathclyde, 1992.Search in Google Scholar
[15] Kitajima J, Kimizuka K, Tanaka Y. New dammarane-type acetylated triterpenoids and their related compounds of Ficus pumila fruit. Chem Pharm Bull (Tokyo) 1999;47:1138–40.10.1248/cpb.47.1138Search in Google Scholar
[16] Torpocco V, Chávez H, Estévez-Braun A, Ravelo AG. New dammarane triterpenes from Maytenus macrocarpa. Chem Pharm Bull (Tokyo) 2007;55:812–4.10.1248/cpb.55.812Search in Google Scholar PubMed
[17] Chapman & Hall Dictionary of natural products on CD-ROM. London: CRC Press, 1998.Search in Google Scholar
[18] Khan R. Natural product: a laboratory guide. New York: Academic Press, 1991.Search in Google Scholar
[19] Beckhauser TF, Francis-Oliveira J, De Pasquale R. Reactive oxygen species: physiological and physiopathological effects on synaptic plasticity. J Exp Neurosci 2016;10(Suppl 1):23–48.10.4137/JEN.S39887Search in Google Scholar PubMed PubMed Central
[20] Pandey KB, Rizvi SI. Plant polyphenols as dietary antioxidants in human health and disease. Oxid Med Cell Longev 2009;2:270–8.10.4161/oxim.2.5.9498Search in Google Scholar PubMed PubMed Central
[21] Blokhina O, Virolainen E, Fagerstedt KV. Antioxidants, oxidative damage and oxygen deprivation stress: a review. Ann Bot 2003;91:179–94.10.1093/aob/mcf118Search in Google Scholar PubMed PubMed Central
[22] Wilmsen PK, Spada DS, Mirian S. Antioxidant activity of the flavonoid hesperidin in chemical and biological system. J Agric Food Chem 2005;53:4757–61.10.1021/jf0502000Search in Google Scholar PubMed
[23] Saeed N, Khan MR, Shabbir M. Antioxidant activity, total phenolic and total flavonoid contents of whole plant extracts Torilis leptophylla L. BMC Complement Altern Med 2012;12:221.10.1186/1472-6882-12-221Search in Google Scholar PubMed PubMed Central
[24] Middha SK, Talambedu U, Pande V. HPLC evaluation of phenolic profile, nutritive content, and antioxidant capacity of extracts obtained from Punica granatum fruit peel. Adv Pharma Sci 2013;2013:6.10.1155/2013/296236Search in Google Scholar
Supplementary Material
The online version of this article offers supplementary material (DOI: 10.1515/jbcpp-2018-0218).
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- Assessment of cardiac risk in chronic asymptomatic alcoholics using blood pressure and electrocardiogram, and the relation with duration of drinking
- Effect of ghrelin on VEGF-B and connexin-43 in a rat model of doxorubicin-induced cardiomyopathy
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