Abstract
Three new sesquiterpenes, 6-hydroxy-7-(1-methylethyl)-3,3a,6,7,8,8a-hexahydroazulene-1,4-dicarboxylic acid methyl ester (1, named viscozulenic acid methyl ester), 7-(1-methylethyl)-3,3a,6,7,8,8a-hexahydroazulene-1,4-dicarboxylic acid 1-methyl ester (2, named viscoazucinic acid) and 3-oxo-1-epi-sclerosporin (3, named polygosumic acid), have been isolated from the chloroform extract of the aerial parts of Polygonum viscosum by reversed-phase preparative high performance liquid chromatography (HPLC). The structures of these compounds were established conclusively by ultraviolet (UV), mass spectrometry (MS) and a series of 1D and 2D nuclear magnetic resonance (NMR) analyses. The anti-bacterial properties of 1–3 against 12 pathogenic bacterial strains have also been assessed by the rapid and robust microtitre-plate-based serial dilution method incorporating resazurin as an indicator of cell growth. Polygosumic acid was the most active among the sesquiterpenes and inhibited the growth of penicillin-resistant Escherichia coli (minimum inhibitory concentration, MIC=0.05 mg/ml) and methicillin-resistant Staphylococcus aureus (MRSA) (MIC=0.10 mg/ml).
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Datta BK, Datta SK, Rashid MA, Kundu JK, Hasan CM, Sarker SD (2002) Further sesquiterpenes from Polygonum viscosum (Polygonaceae). Nat Prod Lett 16:143–148
Phytochemical Database (2007) USDA-ARS-NGRL, Beltsville Agricultural Research Center, Beltsville. Available online at http://www.ars-grin.gov/duke/ethnobot.html
Duwiejua M, Zeitlin IJ, Waterman PG, Gray AI (1994) Anti-inflammatory activity of Polygonum bistorta, Guaiacum officinale and Hamamelis virginiana in rats. J Pharm Pharmacol 46:286–290
Duwiejua M, Zeitlin IJ, Gray AI, Waterman PG (1999) The anti-inflammatory compounds of Polygonum bistorta: isolation and characterisation. Plant Med 65:371–374
Simoes CMO, Ribeiro-do-vale RM, Poli A, Nicolau M, Zanin M (1989) The pharmacologic action of extracts of Polygonum punctatum Elliot (= P. acre HBK) (in French). J Pharm Belg 44:275–284
Tsai PL, Wang JP, Chang CW, Kuo SC, Chao PDL (1998) Constituents and bioactive principles of Polygonum chinensis. Phytochemistry 49:1663–1666
Kuo YC, Meng HC, Tsai WJ (2001) Regulation of cell proliferation, inflammatory cytokine production and calcium mobilization in primary human T lymphocytes by emodin from Polygonum hypoleucum Ohwi. Inflamm Res 50:73–82
Hoque MM, Hassan MA, Khan MR (1989) Screening of plants available in Bangladesh for anti-bacterial activity. II. Polygonum L. Bangladesh J Bot 18:141–145
Datta BK, Datta SK, Khan TH, Kundu JK, Rashid MA, Nahar L, Sarker SD (2004) Anti-cholinergic, cytotoxic and anti-HIV-1 activities of sesquiterpenes and a flavonoid glycoside from the aerial parts of Polygonum viscosum. Pharmaceut Biol 42:18–23
Datta BK, Datta SK, Chowdhury MM, Khan TH, Kundu JK, Rashid MA, Nahar L, Sarker SD (2004) Analgesic, antiinflammatory and CNS depressant activities of sesquiterpenes and a flavonoid glycoside from Polygonum viscosum. Pharmazie 59:222–225
Ahmed M, Rouf ASS, Datta BK (1993) Constituents of Polygonum orientale Linn. Bangladesh J Bot 22:97–98
Datta BK, Datta SK, Sarker SD (2000) Quercetin 3-O-(6″-caffeoyl)-beta-D-galactopyranoside from Polygonum viscosum. Fitoterapia 71:459–460
Datta BK, Datta SK, Sarker SD (2000) Quercetin 3-O-(6″-galloyl)-beta-D-galactoside from Polygonum viscosum (Polygonaceae). Biochem Syst Ecol 28:805–807
Datta BK, Datta SK, Rashid MA, Nash RJ, Sarker SD (2000) A sesquiterpene acid and flavonoids from Polygonum viscosum. Phytochemistry 54:201–205
Datta BK, Rashid MA, Kundu JK, Rouf ASS, Sarker SD, Datta SK (2001) Isolation and structure elucidation of viscoazucine, a novel sesquiterpene from Polygonum viscosum. Pharmazie 56:578–579
Datta BK, Rashid MA, Datta SK, Sarker SD (2001) Viscozulenic acid: a novel sesquiterpene acid from Polygonum viscosum. Pharmaceut Biol 39:198–201
Datta BK, Datta SK, Rashid MA, Sarker SD (2002) Flavonoids from Polygonum stagninum (Polygonaceae). Biochem Syst Ecol 30:693–696
Sarker SD, Nahar L, Kumarasamy Y (2007) Microtitre plate-based anti-bacterial assay incorporating resazurin as an indicator of cell growth, and its application in the in vitro anti-bacterial screening of phytochemicals methods (in press)
Dictionary of natural products (DNP), on CD-ROM (2001) Chapman & Hall/CRC Press, Boca Raton, Florida
ISI database (2007) ISI web of knowledge, Thomson ISI, London, UK. Available online at http://wok.mimas.ac.uk/
Katayama M, Marumo S, Hattori H (1983) The revised structure of sclerosporin, a sporogenic substance of Sclerotinia fructicola: the total synthesis of (±) sclerosporin. Tetrahedron Lett 24:1703–1706
Acknowledgements
We thank the EPSRC National Mass Spectrometry Service Centre (Department of Chemistry, University of Wales Swansea, Swansea, Wales, UK) for the mass spectrometry (MS) analyses.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Datta, B.K., Mukhlesur Rahman, M., Gray, A.I. et al. Polygosumic acid, a new cadinane sesquiterpene from Polygonum viscosum, inhibits the growth of drug-resistant Escherichia coli and Staphylococcus aureus (MRSA) in vitro. J Nat Med 61, 391–396 (2007). https://doi.org/10.1007/s11418-007-0165-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11418-007-0165-4