Hydropiperside, a new Sphingoglycolipid from Polygonum hydropiper

Abstract

One new sphingoglycolipid, hydropiperside, along with two known compounds, flaccidine and quercetin were isolated from the methanolic extract of Polygonum hydropiper. Elucidation of structures was achieved by NMR (1D and 2D) data, mass (EI and FAB) spectroscopy and chemical means.The genus Polygonum, family Polygonaceae, is comprised of about 60 species of annual or perennial herbs [1]. P. hydropiper Linn (syn. Persicaria hydropiper) is used in traditional medicine for many ailments like headache, liver enlargement, gastric ulcer, dysentery, loss of appetite, dysmenorrhea, skin diseases, painful carbuncles, cancer and hemostatics [2,3]. Phytochemical investigations of the species resulted in the isolation of sesquiterpenoids [2,[4][5][6] and aromatic constituents [7][8][9]. In this paper, we describe the isolation, elucidation of structure and bioactivity of a new sphingoglycolipid, hydropiperside (1), together with two known compounds falccidine (2) and quercetin (3) from the methonol extract of the whole plant. Structures were determined by spectroscopic and chemical methods, as well as by comparing the data with that in reported.Hydropiperside, a new sphingoglycolipid from Polygonum hydropiper Natural Product Communications Vol. 10 (4) 2015 643 Compound 1 (1 mg) was heated with 5% HCl in MeOH (1-2 mL) and refluxed for 12 h at 70°C in a scaled small volume vial. The reaction mixture was extracted with n-hexane and the hexane layer was concentrated under reduced pressure to give a mixture of FAM; the MeOH layer was concentrated under vacuum to give a mixture of LCB and the methyl glycoside for GC GCMS analysis [11]. Methanolysis of compound 1: Dimethyl disulfide (DMDS) derivatives of compound 1:Compound 1 (1 mg) was dissolved in CS 2 , and then dimethyl disulfide (0.2 mL) and iodine (1 mg) were added to the solution.The resulting mixture was stored at 60°C for 40 h in a small sealed vial. The reaction was subsequently quenched with aqueous Na 2 S 2 O 3 (5%), and the mixture extracted with n-hexane (0.3 mL). The extract was concentrated to give the DMDS derivative [11].

Identification and biological activity of some new compounds isolated from aerial parts of Polygonum hydropiper

“…Phytochemical investigation of Polygonum hydropiper is essential from the point of economical, medicinal and biological importance. Earlier investigation on the medicinal plant Polygonum hydropiper, Linn, reported some drimane-type sesquiand nor sesquiterpenoids (Huq et al, 2014;Sultana et al, 2011;Haraguchi et al, 1992;Fukuyama et al, 1985Fukuyama et al, , 1982, flavonoid (Peng et al, 2003;Smolarz, 2002;Furuta et al, 1986), and recently, cerebroside (Sultana et al, 2015) type compounds have been isolated. It is also found that one report has been made on the phytochemical investigation of the Bangladeshi origin of this species.…”