Phenolic and iridoid glycosides from the rhizomes of Cyperus rotundus L.
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Med Chem Res (2013) 22:4830–4835 DOI 10.1007/s00044-013-0504-9
ORIGINAL RESEARCH
Phenolic and iridoid glycosides from the rhizomes of Cyperus rotundus L. Zhongliu Zhou • Hualin Zhang
Received: 21 October 2012 / Accepted: 17 January 2013 / Published online: 26 January 2013 Ó Springer Science+Business Media New York 2013
Abstract Two new iridoid glycosides, rotunduside A (1) and rotunduside B (2), along with four known compounds, 600 -O-p-coumaroylgenipin gentiobioside (3), isoaragoside (4), chionoside A (5), and helioside C (6) were isolated from the rhizomes of Cyperus rotundus L. Their chemical structures were determined by application of spectroscopic (NMR, MS) and chemical methodologies. The macrophages respiratory burst (MRB) inhibitory activity of all the isolated compounds was reported. Compound 2 showed marginal inhibitory activity against MRB in the test with IC50 value of approximately 31 lM. Keywords Cyperus rotundus L. Rotunduside A Rotunduside B Macrophages respiratory burst
Introduction Macrophages respiratory burst (MRB) plays an important role in specific and nonspecific immune-inflammatory processes, which links to many inflammatory mediators such as cytokines, chemokines, nitric oxide synthase, phospholipases, and free radical generation. And, inhibition of MRB has been one of the well-documented methods for the evaluation of anti-inflammatory activity for various synthetic compounds and natural products (Qi et al., 2006).
Many scientists have turned their interest to explore potential MRB inhibitors from traditional herbal plants. The rhizome of Cyperus rotundus L. is a kind of traditional Chinese medicine named ‘‘Xiangfuzi’’, which is widely used in folk medicine as an anti-inflammatory, antidepressant, antipyretic, analgesic, and antiemetic remedy for dysentery and women’s diseases (Lawal and Oyedeji, 2009; Zhou and Liu, 2012). Previous phytochemical studies on this plant revealed the presence of alkaloids, flavonoids, glycosides, and furochromones, and many new sesquiterpenoids (Raut and Gaikwad, 2006; Sayed et al., 2008; Jeong et al., 2000; Morimoto and Komai, 2005). Our studies indicated that the 95 % aqueous ethanol extract of rhizomes of C. rotundus L. showed considerable inhibition activity against MRB. To further investigate the constituents and screen the bioactive constituents from its rhizomes, a phytochemical study was performed that resulted in the isolation of three iridoid glycosides and three phenolic compounds. In the present article, we describe the structural elucidation of two new compounds named rotunduside A and rotunduside B, together with the MRB inhibitory activity test performed for all isolated compounds.
Materials and methods General
Z. Zhou (&) H. Zhang Chemistry Science and Technology School, Zhanjiang Normal University, 29 Cunjin Road, Chikan, Zhanjiang, Guangdong 524048, People’s Republic of China e-mail: [email protected] H. Zhang e-mail: [email protected]
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UV spectra were recorded on a Hewlett-Packard HP-845 UV–Vis spectrophotometer. S
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