Phenolic and iridoid glycosides from the rhizomes of Cyperus rotundus L.

Zhou, Zhongliu; Zhang, Hualin

doi:10.1007/s00044-013-0504-9

Cited by 32 publications

(15 citation statements)

References 13 publications

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“…2 Furthermore, the plant possesses different biological activities such as antioxidant, [3][4][5] cytotoxic, 3,5 anti-allergic, 6,7 antipyretic, anti-inflammatory, antiemetic, hypotensive, 8 anticonvulsant, 9 anti-malarial, antimicrobial, 10,11 anti-diarrhoeal, 12 anti-diabetic, 5,13,14 hepatoprotective, 14,15 and insecticide. 16,17 The previous phytochemical studies of C. rotundus L. led to the isolation of sesquiterpenes, 13,[18][19][20][21][22][23] flavonoids, 3,5,8,24,25 phenylpropanoids, 5,26,27 phenolic acids, 5,26 alkaloids, 28 and saponins. 29 In 2013 Zhou and Zhang reported the isolation of iridoid glycosides from C. rotundus rhizomes.…”

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confidence: 99%

Iridoids and other constituents from Cyperus rotundus L. rhizomes

Mohamed

2015

Bulletin of Faculty of Pharmacy, Cairo University

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On continuation of the phytochemical investigation of the MeOH extract of Cyperus rotundus L. Rhizomes, four compounds namely, methyl 3,4-dihydroxy benzoate (1), ipolamiide (2), 6b-hydroxyipolamiide (3), and rutin (4) were isolated. Their structures were established on the basis of 1D and 2D NMR spectroscopic analyses as well as ESIMS spectral data. Compounds 2 and 3 are reported here for the first time from the genus Cyperus and 1 for the first time from the plant. Co-treatment of CCl 4 hepatic injured rats with the total MeOH extract (TME) and EtOAc fraction significantly restored the hepatic marker enzymes and total bilirubin to near-normal values compared to silymarin (reference drug).ª 2015 Production and hosting by Elsevier B.V. on behalf

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Section: Introductionmentioning

confidence: 99%

Iridoids and other constituents from Cyperus rotundus L. rhizomes

Mohamed

2015

Bulletin of Faculty of Pharmacy, Cairo University

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“…Rotunduside C (1) was isolated as a white amorphous powder and gave a molecular formula of C NMR spectroscopic data of 1 were similar to those of rotunduside B, 7 with the exception of two hydroxyl groups at C-3''' and C-5''' in rotunduside B, instead of two methoxyl groups (δ 3.86; δ 56.9) in 1. The suggestion was in accord with the observation of the downfield shift of C-3''' and C-5''' signals from δ 148.6 in rotunduside B to δ 149.4 in 1.…”

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confidence: 88%

“…1,2 Previous phytochemical studies on this plant have led to the isolation and identification of iridoid glycosides, flavonoids, glycosides and furochromones, and many new sesquiterpenoids. [3][4][5][6][7] Our studies indicated that the 95% aqueous ethanol extract of rhizomes of Cyperus rotundus showed considerable inhibition activity against macrophages respiratory burst (MRB). 2 To further investigate the constituents and screen the bioactive constituents from its rhizomes, a phytochemical study was performed that resulted in the isolation of a new iridoid glycoside and two known phenolic glycosides .…”

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A New Iridoid Glycoside from the Rhizomes of Cyperus rotundus

Zhang¹,

Xu²,

Xiao³

et al. 2014

Bulletin of the Korean Chemical Society

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“…Iridoid glycosides, flavonoids, glycosides, and some novel sesquiterpenoids have been reported from Cyperus rotundus [2][3][4][5][6][7]. In this paper we describe a new flavone C-glycoside, 5,7-dihydroxy-4c-methoxy-8-C-[2cc-(2ccc-methylbutyryl)]-E-Dglucopyranosyl flavone, obtained by systematic extraction and isolation from the rhizomes of Cyperus rotundus based on bioactivity-guided analysis.…”

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A New C-Glycosylflavone from the Rhizomes of Cyperus rotundus

et al. 2015

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Cyperus rotundus. Its chemical structure was elucidated on the basis of UV, IR, MS, and NMR spectroscopic analyses. Compound 1 showed moderate inhibitory activity against MRB in the test, with an IC 50 value of approximately 56.03 PM. Keywords: Cyperus rotundus, flavonoid, macrophage respiratory burst.The rhizome of Cyperus rotundus is an important traditional Chinese medicine, which is widely used in folk medicine as an anti-inflammatory, antidepressant, antipyretic, analgesic, and antiemetic remedy for dysentery and womencs diseases [1]. Iridoid glycosides, flavonoids, glycosides, and some novel sesquiterpenoids have been reported from Cyperus rotundus [2][3][4][5][6][7]. In this paper we describe a new flavone C-glycoside, 5,7-dihydroxy-4c-methoxy-8-C-[2cc-(2ccc-methylbutyryl)]-E-Dglucopyranosyl flavone, obtained by systematic extraction and isolation from the rhizomes of Cyperus rotundus based on bioactivity-guided analysis.Compound 1 was isolated as a pale yellow amorphous powder. Its molecular formula, C 27 H 30 O 11 , was deduced by HR-EI-MS (calcd m/z 531.1904; found 531.1872, [M + H] + ). The UV spectrum exhibited absorption maxima at 266 nm (band II) and 340 nm (band I), which are characteristic absorption bands of a flavone skeleton. The IR spectrum of 1 displayed absorptions at 3346 (hydroxyl), 1736 (ester), and 1643 cm -1 (D,E-unsaturated ketone). The occurrence of a flavone skeleton in the molecule could be easily deduced from the 1 H NMR spectrum, which showed the signals for an exchangeable proton at G 13.58 (1H, s, 5-OH), a sharp one-proton singlet at G 6.87 (1H, s, H-3) on the C-ring, and AAcBBc-type aromatic protons at G 8.10 (2H, d, J = 8.0 Hz, H-2c, 6c) and G 6.93 (2H, d, J = 8.0 Hz, H-3c, 5') on the B-ring, together with one broad singlet at G 6.08 (1H, s, H-6) on the A-ring [8,9]. The above NMR spectroscopic data revealed the presence of a trisubstituted A-ring and a p-substituted B-ring in 1. In addition, the 1 H NMR spectrum showed a series of signals between G 3.50 and 4.90 indicative of a sugar moiety. The coupling constant (J = 10.0 Hz) of the anomeric proton [G 4.88 (1H, d)] is consistent with the presence of a E-C-glucoside in 1 [10], a fact supported further by the 13 C NMR signals (G 70.6, 71.4, 75.2, 70.4, 82.5, and G 61.1) of the sugar unit [11]. The 1 H and 13 C NMR spectrum also displayed the presence of signals attributable to a 2ccc-methylbutyryl unit [G H 0.61 (3H, t, J = 7.2 Hz, H-4ccc), 0.68 (3H, t, J = 7.2 Hz, 2ccc-CH 3 ), 1.11 (2H, m, H-3ccc), and 1.99 (1H, m, H-2ccc); G C 11.0 (C-4ccc), 16.3 (2ccc-Me), 25.6 (C-3ccc), 40.3 (C-2ccc), 174.4 (C-1ccc)], which was confirmed by long-range correlations from H- (Fig. 1). The observed 13 C NMR chemical shift of the C-glycosylated carbon (G 104.3, C-8) of ring A revealed the presence of a C-8 glycosylated flavonoid skeleton in 1. The presence of the C-8 glycosyl moiety was supported further by the HMBC correlations observed between the anomeric proton [G 4.88 (1H, d, J = 10.0 Hz,] and the quaternary carbons C-7, C-8, and C-8a of r...

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Phenolic and iridoid glycosides from the rhizomes of Cyperus rotundus L.

Cited by 32 publications

References 13 publications

Iridoids and other constituents from Cyperus rotundus L. rhizomes

Iridoids and other constituents from Cyperus rotundus L. rhizomes

A New Iridoid Glycoside from the Rhizomes of Cyperus rotundus

A New C-Glycosylflavone from the Rhizomes of Cyperus rotundus

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