Galloylated flavonol rhamnosides from the leaves of Calliandra tergemina with antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA)
Graphical abstract
Galloylated flavonol rhamnosides 1–3, together with five known flavonol rhamnosides, were isolated from a leaf extract of Calliandra tergemina. All metabolites were analysed for their potential anti-MRSA activities.
Introduction
The genus Calliandra belongs to the family Leguminosae and subfamily Mimosaceae. The family has about 200 species of flowering plants native to tropical America, Madagascar and India. Several species are planted as ornamental plants (Mattagajasingh et al., 2006). There is, however, presently no paper describing the chemical constituents and bioactivity of Calliandra tergemina although there are reports on several related species including Calliandra portoricensis, Calliandra californica and Calliandra haematocephala (Aguwa and Lawal, 1988, Encarnacion et al., 1994, Agunu et al., 2005, Moharram et al., 2006 Orishadipe et al., 2010). Preliminary screening of the leaf extracts of C. tergemina displayed antibacterial activity against Micrococcus luteus, Bacillus cereus, methicillin-sensitive Staphylococcus aureus (MSSA) and methicillin-resistant Staphylococcus aureus (MRSA), respectively (Chew et al., 2011). The activity against MRSA is interesting as the latter is a major cause of infections in hospitals and resistant to all known beta-lactam antibiotics (Otsuka et al., 2008, Chew et al., 2011). Thus a bioassay-guided fractionation of C. tergemina leaf extracts, coupled with chromatographic separation; was employed to isolate the active constituents. This yielded three new galloylated flavonol rhamnosides and five known flavonol rhamnosides. This paper describes the isolation, structure elucidation and the structure–activity relationships of the isolated compounds.
Section snippets
Results and discussion
Five crude extracts were obtained from the leaves of C. tergemina of which the ethyl acetate extract had the highest anti-MRSA activity (Table 1); and from his extract, eight flavonol glycosides were isolated using a combination of silica gel column and gel filtration chromatography. Three new compounds were identified by their NMR (1H, 13C, HSQC, HMBC), UV and mass spectra, optical rotations, and by comparison with previously reported spectroscopic data. The five known galloylated and
Concluding remarks
Eight flavonol rhamnosides, including three new galloylated flavonol rhamnosides, were isolated from the leaves of C. tergemina. This is the first report on the phytochemical study of C. tergemina. The anti-MRSA activity of the extracts and isolated flavonol rhamnosides showed their structure–activity relationship where the esterification of the rhamnoside moiety was important in conferring anti-MRSA activity compared to the corresponding flavonol rhamnosides. There was no correlation between
General
Silica gel (Kieselgel 60, 70–230, and 230–400 mesh, Merck KGaA, Darmstadt, Germany), and Sephadex LH-20 (Pharmacia Fine Chemicals AB, Uppsala, Sweden) were used for column chromatography (CC). Optical rotations were measured on an Atago AP-300 automatic polarimeter. Ultraviolet (UV) absorption spectra were measured in MeOH using a HPLC with a UV/VIS detector separated by a C-18 reversed phase column (Assentis 25 cm × 4.9 mm × 5 μm). The HPLC profiles were processed with Agilent software to obtain the
Acknowledgements
The authors are thankful to Monash University Malaysia for financial support to EWLC for a visit to the Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde Glasgow for the use their NMR facilities and the University of Malaya Kuala Lumpur for LCMS analysis. We are grateful to Mr. Anthonysamy Savarimuthu (formerly of the University Putra Malaysia) for identifying the plant material.
References (22)
- et al.
Analgesic activity of roots and leaves extracts of Calliandra portoricensis
Fitoterapia
(2005) - et al.
Pharmacologic studies on the active principles of Calliandra portoricensis leaf extracts
J. Ethnopharmacol.
(1988) - et al.
A new flavonol galloylrhamnoside and a new lignan glucoside from the leaves of Koelreuteria henryi Dummer
J. Nat. Med.
(2009) - et al.
Genetic relationships among nine cultivated taxa of Calliandra Benth. (Leguminosae: Mimosoideae) using random amplified polymorphic DNA (RAPD) markers
Sci. Hortic.
(2006) - et al.
In vitro and in vivo antimicrobial effects of mastic chewing gum against Streptococcus mutans and mutans streptococci
Arch. Oral. Biol.
(2006) - et al.
Assessment of phytochemical content, polyphenolic composition, antioxidant and antibacterial activities of Leguminosae medicinal plants in Peninsular Malaysia
BMC Complement Altern. Med.
(2011) - et al.
Antimicrobial activity and biofilm formation inhibition of green tea polyphenols on human teeth
Biotechnol. Bioprocess Eng.
(2010) - Clinical and Laboratory Standards Institute (CLSI), 2002. Reference method for dilution antimicrobial susceptibility...
- et al.
High phenolics and antioxidants of some tropical vegetables related to antibacterial and anticancer activities
Afr. J. Pharm. Pharmacol.
(2011) Isolation and structure elucidation of phenolic compounds of carob leaves grown in Egypt
Curr. Res. J. Biol. Sci.
(2011)
Two new flavones from Calliandra californica
J. Nat. Prod.
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