Kaempferol triosides from Silphium perfoliatum

El-Sayed, Nabil H.; Wojcińska, Małgorzata; Drost-Karbowska, K; Matławska, Irena; Williams, Jeffrey; Mabry, Tom J.

doi:10.1016/s0031-9422(02)00133-4

Cited by 37 publications

(29 citation statements)

References 14 publications

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“…Biological activity of methanol extracts may be associated with the occurrence of soluble phenolic and polyphenolic compounds, including phenolic acids (Table 3) (Kowalski & Wolski, 2003a,b), caffeotanoids and flavonoids (El-Sayed et al, 2002;Kowalski, 2003) (Table 3), oleanosides (Davidjanc & Abubakirov, 1992;Kowalski, 2002Kowalski, , 2004b (Table 3), and volatile terpenes (Kowalski & Wolski, 2005) (Table 2) in S. perfoliatum. Furthermore, besides the biologically active substances given above, significant contents of 16-acetoxycarterochaetol (about 68%) (Table 2) in methanol extract versus about 45% in hexane extract were found in rhizomes, which may also have an effect on higher activity of alcohol extracts made of below-ground parts of the plant.…”

Section: Resultsmentioning

confidence: 99%

“…Chemical composition determinations revealed the above-mentioned Silphium species contained: phenolic acids (Kowalski & Wolski, 2003a,b;Kowalski, 2004b), flavonoids (El-Sayed et al, 2002;Kowalski, 2003Kowalski, , 2004b, terpenes (Bohlmann & Jakupovic, 1979, 1980Pcolinski et al, 1994;Kowalski, 2005) including triterpene saponins-oleanosides (Davidjanc & Abubakirov, 1992;Kowalski, 2002Kowalski, , 2004b, as well as essential oils Kowalski & Wolski, 2005). Moreover, rhizomes and roots of Silphium contained the reserve carbohydrate inulin (Kowalski & Wierciń ski, 2004a) and seeds may be an alternative source that would enrich the functional food in nutrients and pro-health components (Kowalski & Wierciń ski, 2004b).…”

Section: Introductionmentioning

confidence: 99%

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Antibacterial Activity ofSilphium perfoliatum. Extracts

Kowalski¹,

Kędzia

2007

Pharmaceutical Biology

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Methanol and hexane extracts obtained from above-and below-ground organs of the cup plant Silphium perfoliatum L. (Asteraceae) were analyzed by gas chromatography-mass spectrometry (GC-MS). Eighty-five components were identified in the extracts. Moreover, evaluation of the content of total secondary metabolites (flavonoids, o-dihydroxyphenols, and glycoside-bonded oleanolic acid) was made in the methanol extract. It was found that leaf, inflorescence, and rhizome extracts of S. perfoliatum were characterized by antibacterial action toward Gram-positive (Enterococcus faecalis, Staphylococcus aureus) and Gram-negative (Escherichia coli, Pseudomonas aeruginosa bacteria). All the extracts showed extremely high activity toward Staphylococcus aureus FDA 209P strains (MIC values: 1.00 mg=mL for rhizome alcohol and hexane extracts; 2.50 mg=mL for leaf and inflorescence alcohol extracts and for leaf hexane extracts; 5.00 mg=mL for inflorescence hexane extracts). In general, alcohol extracts had slightly stronger antibacterial properties compared with lipophilic ones. Among the alcohol extracts, those made of S. perfoliatum rhizomes had the highest activity compared with the leaf and inflorescence extracts.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Antibacterial Activity ofSilphium perfoliatum. Extracts

Kowalski¹,

Kędzia

2007

Pharmaceutical Biology

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“…Nine (2-10) of these compounds were identified as trans-tiliroside (2) [4], caffeic acid (3) [5], chlorogenic acid (4) [6,7] (Table 1) of 1 also indicated the presence of three sugar moieties together with a C15 aglycone unit. These spectral data of 1 were almost identical with those of kaempferol trioside [12,13]. Additionally, from the 1 H-and 13 C-NMR spectral data, 1 was supposed to be a kaempferol glycoside with rutinose [14][15][16] and apiofuranose [13] moieties.…”

Section: Resultsmentioning

confidence: 52%

“…These spectral data of 1 were almost identical with those of kaempferol trioside [12,13]. Additionally, from the 1 H-and 13 C-NMR spectral data, 1 was supposed to be a kaempferol glycoside with rutinose [14][15][16] and apiofuranose [13] moieties. The HMBC correlation (Fig.…”

Section: Resultsmentioning

confidence: 52%

A new kaempferol trioside from Solidago altissima L.

et al. 2007

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A new kaempferol trioside [kaempferol 3-O-rutinoside 7-O-b-D-apiofuranoside, (1)] was isolated together with nine phenolic compounds, trans-tiliroside (2), caffeic acid (3), chlorogenic acid (4), 3-O-caffeoylquinic acid (5), 4-O-caffeoylquinic acid (6), 3-Ocoumaroylquinic acid (7), 4-O-coumaroylquinic acid (8), 3,5-di-O-caffeoylquinic acid (9) and 4,5-dicaffeoylquinic acid (10) from the leaves of Solidago altissima L. The structure elucidations of the compounds were based on the analyses of spectroscopic data.

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“…300 ml each) were collected and combined on the basis of TLC analysis leading to two main series I-II. Series I (4 g) [fractions [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16] was eluted with a mixture of hexane/ethyl acetate (5 : 2) to deliver b,2,3Ј,4,4Ј,6-hexahydroxy-a-(a-Lrhamnopyranosyl)dihydrochalcone (2, 2.4 mg). Series II (1.5 g) [fractions 17-35] was column chromatographed on silica gel and eluted with CH 2 Cl 2 -MeOH (3 : 1) to yield 12-hentriacontanol (1.9 mg) 14) and hentriacontane (4.7 mg).…”

Section: Methodsmentioning

confidence: 99%

Flavonoid Glycosides and Other Constituents of Psorospermum androsaemifolium BAKER (Clusiaceae)

Poumale

Randrianasolo

Rakotoarimanga

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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Psorospermum androsaemifolium BAKER, an endemic plant from Madagascar, locally known as "Tsifady", "Harongampanihy", "Fanerana" or "Hazomafaika" belongs to the Clusiaceae family.1) In the traditional medicine it is used as remedy for spiders or scorpions bite and also healing stomach disease.2,3) The widespread use of P. androsaemifolium in indigenous medicine for different ailments, justified further attempts to isolate and identify active compounds. The present paper deals with the isolation and structural elucidation of one new flavone glycoside and one new dihydrochalcone glycoside including their antimicrobial activities. To the best of our knowledge, no previous phytochemical study has been reported on P. androsaemifolium. Results and DiscussionThe leaves of P. androsaemifolium were extracted at room temperature with methanol for 2 d. This extract was concentrated to dryness under vacuum, and after flash chromatography on silica gel using a hexane/ethyl acetate gradient of increasing polarity; fractions A-C were obtained. Repeated column chromatography and preparative TLC afforded quercetin (1), acanthophorin B (1a), vismiaquinone, aand b-amyrine, 12-hentriacontanol, hentriacontane and two new flavonoid glycosides: 3Ј-(2Љ,4Љ-dihydroxybenzyloxy)-acanthophorin B (1b) and b,2,3Ј,4,4Ј,6-hexahydroxy-a-(a-L-rhamnopyranosyl)dihydrochalcone (2). The 1 H-and 13 C-NMR, and MS data of the known compounds were consistent with those reported in the literature.Compounds 1 and 1a were isolated as yellow powder in silica gel column (3ϫ40 cm) from fraction A eluted with solvent system dichloromethane/methanol of increasing polarity. The EI mass spectrum of compound 1a exhibited a molecular ion at m/z 448 corresponding to a molecular formula C 21 H 20 O 11 . Two new flavonoid glycosides, namely 3-(2؆,4؆-dihydroxybenzyloxy)acanthophorin B (1b) and b b,2,3,4,4,6-hexahydroxy-a a-(a a-L-rhamnopyranosyl)dihydrochalcone (2) were isolated from the leaves of Psorospermum androsaemifolium together with quercetin (1), acanthophorin B (1a), a a-(3) and b b-amyrine (3a), vismiaquinone (4), 12-hentriacontanol and hentriacontane. The structures of these secondary metabolites were established using detailed spectroscopic analysis and by comparison with published data. Compounds 1, 1a, 1b, 2, 3, 3a and 4 showed weak antifungal and antibacterial activities.

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Kaempferol triosides from Silphium perfoliatum

Cited by 37 publications

References 14 publications

Antibacterial Activity ofSilphium perfoliatum. Extracts

Antibacterial Activity ofSilphium perfoliatum. Extracts

A new kaempferol trioside from Solidago altissima L.

Flavonoid Glycosides and Other Constituents of Psorospermum androsaemifolium BAKER (Clusiaceae)

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