Flavonoide aus salix alba. Die struktur des Terniflorins und eines weiteren acylflavonoides

Karl, Christian; Müller, Gerhard; Pedersen, Peter Alsted

doi:10.1016/s0031-9422(00)84419-2

Cited by 32 publications

(16 citation statements)

References 6 publications

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“…These compounds included the six flavonols, quercetin (5), 25) isorhamnetin (6), 26) rhamnetin (7), 27) quercitrin (8), 25) kaempferol (9), 25) and afzelein (10), 28) the five flavons, chrysoeriol (11), 29) apigenin (12), 30) tricin (13), 31) luteolin (14), 32) and amentoflavone (15), 33) the flavanonol, taxifolin (16), 34) the chalcone, isoliquiritigenin (17), 35) the dithiodicarboxylic acid, 3,3′-dithiodipropanoic acid (18), 36) the indole derivative, indole-3-carboxylic acid (19), 37) the alloxazine derivative, 7,8-dimethylalloxazine (20), 38) the phenylpropanoid, (E)-p-coumaric acid (21), 39) and the mono-terpenoid, (6S)-menthiafolic acid (22). 40) Compounds 6, 7, 11-22 were isolated for the first time from the flower of A. julibrissin.…”

Section: Resultsmentioning

confidence: 99%

Flavonol Acylglycosides from Flower of Albizia julibrissin and Their Inhibitory Effects on Lipid Accumulation in 3T3-L1 Cells

2012

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Obesity is a serious health problem worldwide. We investigated the anti-obesity effect of the flower of Albizia julibrissin DURAZZ. (Leguminosae). A 90% EtOH extract of the flower inhibited adipogenesis in 3T3-L1 preadipocytes, as well as the activity of glycerol-3-phosphate dehydrogenase (GPDH) activity. New flavonol acylglycosides (1-4) and eighteen known compounds (5-22) were isolated by bioassay-directed fractionation. These new glycosides were elucidated to be 3″-(E)-p-coumaroylquercitrin (1), 3″-(E)-feruloylquercitrin (2), 3″-(E)-cinnamoylquercitrin (3), and 2″-(E)-cinnamoylquercitrin (4) on the basis of spectroscopic and chemical analysis. These compounds inhibited adipogenesis in 3T3-L1 preadipocytes. In particular, 2 exhibited potent inhibitory effects on triglyceride accumulation. Furthermore, GPDH activity was inhibited by 2. Additionally, 2 inhibited glucose uptake in 3T3-L1 adipocytes. These results indicate that the 90% EtOH extract and compounds isolated from the flower of A. julibrissin inhibit adipogenesis in 3T3-L1 preadipocytes and may have anti-obesity effect through the inhibition of preadipocyte differentiation.

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Section: Resultsmentioning

confidence: 99%

Flavonol Acylglycosides from Flower of Albizia julibrissin and Their Inhibitory Effects on Lipid Accumulation in 3T3-L1 Cells

2012

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“…The I H NMR spectrum of 2 showed low frequency signals at δ 12.34 and 13.18 assignable to the chelated hydroxyl groups at C-3 and C-5 of a flavonoid moiety. Two meta-coupled doublets (J = 2.0 Hz), each integrating for one proton at δ 6.67 and 6.65, were diagnostic for a C- and δ 6.48 (d, J = 15.8 Hz) [19] as well as protrons of p-hydroxy phenyl ring showing another AA XX pattern at 7.48 (d, J = 8.6 Hz) and 7.13 (d, J = 8.6 Hz), respectively. The presence of a pentose moiety was revealed by the signal of anomeric proton at δ 6.21 and further signals of oxymethine and oxymethylene protons at The key to the structure of abutilin A (2) was provided by the acid hydrolysis, which afforded, besides the sugar moiety, a mixture of aglycones identified as (E)-p-coumaric acid and kaempferol.…”

Section: Resultsmentioning

confidence: 99%

Structural determination of abutilins A and B, new flavonoids from Abutilon pakistanicum, by 1D and 2D NMR spectroscopy

Ali

Imran

Hussain

et al. 2009

Magnetic Reson in Chemistry

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Two new flavonoids, abutilin A and B, were isolated from the chloroform soluble fraction of Abutilon pakistanicum and their structures assigned from (1)H and (13)C NMR spectra, DEPT and by 2D COSY, HMQC and HMBC experiments. Ferulic acid (3), (E)-cinnamic acid (4), 5-hydroxy-4',6,7,8-tetramethoxyflavone (5), kaempferol (6), luteolin (7) and luteolin 7-O-beta-D-glucopyranoside (8) have also been reported from this species.

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“…22 The IR spectrum apart from hydroxyl (3408-3030 cm -1 ), monosubstituted double bond (3081, 1642, 982 and 918 cm -1 ), aromatic ring (1600 and 1512 cm -1 ) and glycosidic bond (1075 cm -1 ) characteristic absorption bands, showed an additional a,b-unsaturated ester (1701, 1628 and 970 cm -1 ), indicating the presence of an ester group conjugated with a trans-double bond. 23 . According to these spectral data, 1 was considered to be a trans-sinapoyloxy-8,13-epoxylabdane diterpene glucoside.…”

Section: Resultsmentioning

confidence: 99%

A New Diterpenoid and other Constituents from Acanthopanax Brachypus Harms

Fan

2009

J Chinese Chemical Soc

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Phytochemical investigation of the stem bark of Acanthopanax brachypus afforded a new labdanetype diterpene glycoside, 3a-trans-sinapoyloxy-jhanol 18-O-b-D-glucopyranoside (1), together with four known compounds, including one diterpene acid, acanthoic acid (2), one coumarin, isofraxidin (3), one phenolic glycoside, sasanquin (4), as well as one chalcone glycoside, okanin 4-methyl ether-3¢-O-b-D-glucopyranoside (5). All of the structures were characterized by means of spectroscopic methods, including 1 H, 13 C, 2D-NMR and HR-MS, as well as chemical methods and comparison with the literature data.

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Flavonoide aus salix alba. Die struktur des Terniflorins und eines weiteren acylflavonoides

Cited by 32 publications

References 6 publications

Flavonol Acylglycosides from Flower of Albizia julibrissin and Their Inhibitory Effects on Lipid Accumulation in 3T3-L1 Cells

Flavonol Acylglycosides from Flower of Albizia julibrissin and Their Inhibitory Effects on Lipid Accumulation in 3T3-L1 Cells

Structural determination of abutilins A and B, new flavonoids from Abutilon pakistanicum, by 1D and 2D NMR spectroscopy

A New Diterpenoid and other Constituents from Acanthopanax Brachypus Harms

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