Conferols A and B, New Anti-inflammatory 4-Hydroxyisoflavones from Caragana conferta

Khan, Rahmat Ullah; Malik, Abdul; Adhikari, Achyut; Qadir, Muhammad Irfan; Choudhary, M. Iqbal

doi:10.1248/cpb.57.415

Cited by 17 publications

(12 citation statements)

References 14 publications

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“…7 Proton signals at d H 6.52 (J = 2.2 Hz), d H 6.45 (J = 2.2, 8.6 Hz) and d H 7.01 (J = 8.6 Hz) also revealed that the ring B should be 2¢,4¢-disubstituted. 8 The HMBC correlations ( Fig. 2) of phenolic hydroxy proton signal (d H 11.27) with C-3¢ (d C 100.2), C-4¢ (d C 160.0) and C-5¢ (d C 107.1) indicated that the phenolic hydroxy group should be located at C-4¢.…”

Section: Resultsmentioning

confidence: 95%

Two New 4‐Hydroxyisoflavanes from the Root of Codonopsis cordifolioidea and Their Anti‐virus Activities

Yang³

et al. 2012

J Chinese Chemical Soc

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Two new 4-hydroxyisoflavanes, cordifoliflavanes A and B (1 and 2), were isolated from the roots of Codonopsis cordifolioidea. Their structures were elucidated by spectroscopic methods, including extensive 1D-and 2D-NMR techniques. Compounds 1 and 2 were tested for their anti-HIV-1 activities and anti-tobacco mosaic virus activities. The results showed that compounds 1 and 2 have modest anti-HIV-1 activities and anti-tobacco mosaic virus activities, respectively.

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Section: Resultsmentioning

confidence: 95%

Two New 4‐Hydroxyisoflavanes from the Root of Codonopsis cordifolioidea and Their Anti‐virus Activities

Yang³

et al. 2012

J Chinese Chemical Soc

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“…The signal of the methoxyl group appeared at  3.80 (3H, s). The position of the methoxyl group was ascertained through HMBC, showing 3 J correlation of methoxyl protons with C-3' ( 149.2). It was supported by the observation of a strong NOESY (nuclear Overhauser effect spectroscopy) correlation between the methoxyl protons and H-2' (Figure 2).…”

Section: Resultsmentioning

confidence: 99%

“…Plants of the genus Caragana are used as folk medicine in China and Korea for the treatment of neuralgia, rheumatism, arthritis, and hypertension 2 . A literature survey revealed that few compounds have so far been reported from this species 3,4 . A methanolic extract of this plant showed strong toxicity in the brine shrimp lethality test, and on subsequent fractionation the major toxicity was observed in the ethyl acetate soluble sub-fraction.…”

Section: Introductionmentioning

confidence: 99%

“…Further pharmacological screening of this fraction revealed potent antioxidant activity. In this article we report the isolation of a new isoflavone (1), named conferin, along with several known compounds: biochanin A (2) 5 , p-hydroxybenzoic acid (3) 6 , 3,5-dimethoxybenzoic acid (4) 6 , ursolic acid (5) 7 , erythrodiol (6) 8 , pinoresinol (7) 9 , and syringresinol (8) 10 . This study was undertaken to investigate the antioxidant potentials using different tests including 1,1-diphenyl-2-picryl-hydrazyl (DPPH) radical scavenging activity and reducing power.…”

Section: Introductionmentioning

confidence: 99%

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Conferin, potent antioxidant and anti-inflammatory isoflavone fromCaragana confertaBenth

Khan

Perveen

Malik

et al. 2010

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…This is a new steroidal glycoside isolated from a natural or synthetic source for the first time. The known compounds have been identified as stigmast-5en-3E-ol (E-sitosterol) [15,16], lup-20(29)-en-3E-ol(lupeol) [16,17], and stigmast-5en-3E-ol-E-D-glucopyranoside (E-sitosterol glucoside) [16,18].…”

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confidence: 99%

New steroidal glycosides from the stem bark of Mimusops elengi

2010

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Two new steroidal glycosides (1 and 2) have been isolated from the ethanolic extract of the stem bark of Mimusops elengi L. and characterized as Keywords: Mimusops elengi L., Sapotaceae, stem bark, steroidal glycosides.Mimusops elengi L. (Sapotaceae) is an ornamental small tree with sweet scented flowers growing wild throughout the greater part of India [1]. All parts of the plant are prescribed in the indigenous system of medicine as a febrifuge, astringent, purgative, and stimulant [2]. The decoction of the bark is used as a gargle [3]. It exhibited antimicrobial, antiulcer, hypotensive, anti-HIV, and spasmolytic activities [4][5][6][7][8]. Ursolic acid, betulinic acid, the fatty acid ester of D-spinasterol [9], 3E,6E,19D,23-tetrahydroxyurs-12-ene, 1E-hydroxy-3E-hexanoyllup-20(29)-ene-23,28-dioic acid, and bassic acid have been isolated from the bark [10,11]. This paper deals with the isolation and structural elucidation of two new steroidal glycosides from the stem bark of Mimusops elengi L.Compound 1, designated as stigmasterol-E-D-glycopyranoside, was obtained as a colorless amorphous powder from chloroform-methanol (19:1) eluants. It gave a positive test for sterol glycosides. Its IR spectrum exhibited absorption bands for hydroxyl groups (3450, 3380, 3260 cm -1 ), ester group (1738 cm -1 ), and unsaturation (1614 cm -1 ). On the basis of mass and 13 C NMR spectra, its molecular weight was established at m/z 750, consistent with the molecular formula of a sterol diglucoside, C 41 H 66 O 12 , and confirmed by HR-MS 751.9713 [M + H] + . Its mass spectrum showed important ion fragments appearing at m/z 411 [M -C 12 H 19 O 11 , diglycoside] + , 271 [411 -C 10 H 19 , side chain] + , 255 [271 -Me] + , and 239 [255 -Me] + .These fragments suggested that it was a C 29 sterol possessing one double bond in the carbocyclic ring system and one double bond in the side chain. The mass spectrum indicated the presence of an ethyl group in the side chain, which was placed at C-24 on the basis of biosynthesis analogy as well as similarities in chemical shifts of protons and carbons of the side chain with the related compounds. The ion fragments at m/z 339 [M -411] + and 179 [C 6 H 11 O 6 ] + suggested the glucuronosyl glucoside nature of the carbohydrate moiety. The 1 H NMR spectrum of 1 exhibited two one-proton multiplets at G 5.07 and 5.28 assigned to vinylic H-22 and H-23. A one-proton broad signal at G 5.30 was ascribed to vinylic H-6. A one-proton broad multiplet at G 3.85 with half-width 16.5 Hz was attributed to D-oriented C-3 carbinol proton. Two one-proton doublets at G 4.95 (J = 7.2 Hz) and 4.88 (J = 7.0 Hz) were attributed to H-1c and H-1cc anomeric protons, respectively. A two-proton broad signal at G 3.33 was associated with oxygenated C-6cc methylene protons. The remaining hydroxymethine protons of the glycosidic linkage appeared between G 4.50-3.35. Two three-proton broad signals at G 0.66 and 1.19 were assigned to C-18 and C-19 tertiary methyl protons. Four doublets at G 0.96 (J = 6.1 Hz), 0.86 (J = 8.4 Hz), ...

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Conferols A and B, New Anti-inflammatory 4-Hydroxyisoflavones from Caragana conferta

Cited by 17 publications

References 14 publications

Two New 4‐Hydroxyisoflavanes from the Root of Codonopsis cordifolioidea and Their Anti‐virus Activities

Two New 4‐Hydroxyisoflavanes from the Root of Codonopsis cordifolioidea and Their Anti‐virus Activities

Conferin, potent antioxidant and anti-inflammatory isoflavone fromCaragana confertaBenth

New steroidal glycosides from the stem bark of Mimusops elengi

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