Acylated kaempferol glycosides from the flowers of delphinium formosum

Özden, Seçkin; Dürüst, Nedïme; Toki, Kenjiro; Saitô, Norio; Honda, Toshio

doi:10.1016/s0031-9422(97)01044-3

Cited by 39 publications

(18 citation statements)

References 7 publications

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“…Eight compounds were isolated from the chloroform layer. Compounds 4-30 were identified by detailed comparisons of their spectroscopic data with those in the literature as kaempferol (4), 13) 16) tiliroside (8), 3) quercetin (9), 17) rutin (10), 18) 24) isorhamnetin 3-O-β-d-glucopyranoside (17), 15) gallic acid (18), 25) methyl gallate (19), 26) 4-hydroxybenzoic acid (20), 27) protocatechuic acid (21), 28) methyl brevifolincarboxylate (22), 29) ursolic acid (23), 30) ursolic aldehyde (24), 31) 28-nor-urs-12-ene-3β,17β-diol (25), 32) pomolic acid (26), 33) 2α-hydroxy ursolic acid (27), 33) 23-hydroxy ursolic acid (28), 34) vomifoliol (29), 35) and β-sitosterol (30) 30) (Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

Inhibitory Effects of the Constituents of <i>Hippophae rhamnoides</i> on 3T3-L1 Cell Differentiation and Nitric Oxide Production in RAW264.7 Cells

Yang

Wen

et al. 2013

Chem. Pharm. Bull.

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Three new flavonol glycosides, hippophaeosides A-C (1-3), together with 27 known constituents, were isolated from Hippophae rhamnoides L. leaves. Their structures were determined by spectroscopic analyses. Their inhibitory activities on 3T3-L1 preadipocyte differentiation and triglyceride accumulation in maturing adipocytes, and nitric oxide production in RAW264.7 cells were examined.Key words Hippophae rhamnoides; flavonol glycoside; triterpenoid; adipocyte; macrophage Hippophae rhamnoides L. (Elaeagnaceae), known as "sea buckthorn," is a deciduous shrub distributed throughout Asia and Europe. The fruit has been used as a traditional medicine for the treatment of cough indigestion and blood stasis in China.1) Investigations of H. rhamnoides have yielded flavonols, 2-4) triterpenoids, 5,6) and tannins.3) The leaf has been reported to have anti-inflammatory, 7) antioxidant, 4) anti-obesity, 8,9) and α-glucosidase inhibitory activities. 4)In our previous study, we investigated anti-obesity and antiinflammatory compounds that not only inhibit triglyceride (TG) accumulation by 3T3-L1 adipocytes but also inhibit the secretion of nitric oxide (NO) from RAW264.7 cells. In that study, several crude drugs were examined. [10][11][12] In the present study, the 80% methanol extract of the leaves of H. rhamnoides L. and the chloroform-and ethyl acetatesoluble portions of the extract were observed to inhibit the TG accumulation in 3T3-L1 cells, and inhibit NO production in lipopolysaccharide (LPS) and interferon-γ (IFN-γ) activated macrophages. Furthermore, an attempt to identify the bioactive compounds present in this plant led to the isolation of three new flavonol glycosides, Hippophaeosides A (1), B (2), and C (3), along with 27 known constituents. Results and DiscussionThe leaves of H. rhamnoides L. were extracted with 80% aqueous methanol, followed by evaporation of the solvent under reduced pressure from the combined extract to give the 80% methanol extract. The extract [TG and NO inhibitory activity: 35% and 63%, respectively (30 µg/mL) [42, 15% (30 µg/mL)]. We focused our efforts on investigating the chemical constituents of the chloroform-and ethyl acetate-soluble fractions. The ethyl acetate layer was separated by Sephadex LH-20 column chromatography to yield four fractions from which 22 compounds including three new compounds 1-3 were isolated. Eight compounds were isolated from the chloroform layer. Compounds 4-30 were identified by detailed comparisons of their

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Section: Resultsmentioning

confidence: 99%

Inhibitory Effects of the Constituents of <i>Hippophae rhamnoides</i> on 3T3-L1 Cell Differentiation and Nitric Oxide Production in RAW264.7 Cells

Yang

Wen

et al. 2013

Chem. Pharm. Bull.

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“…Since catalytic step(s) in the anthocyanin synthesis pathway in addition to DFR may also possibly be rate limiting, the levels of expression of genes for other enzymes will need to be quantified and their enzyme activities will need to be determined in 'SHP' . Delphinium sepals also accumulate flavonol glycosides and, thus, the possible co-pigmentation roles of flavonoids in modulating flower color hue need to be considered (Özden et al 1998;Yoshida et al 2009). Additionally, since visible flower color is affected by cell shape, vacuolar pH, and anthocyanic vacuolar inclusion formation, as well as accumulated anthocyanin molecules, the possibility of multiple factors influencing flower color intensity will be examined in future studies.…”

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Dihydroflavonol 4-reductase activity is associated with the intensity of flower colors in delphinium

Miyagawa

Miyahara

Okamoto³

et al. 2015

Plant Biotechnology

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Flower color intensity is largely determined by the amount of accumulated anthocyanins. Delphinium flowers show a wide range of colors from pale pink to deep orange to red to dark blue. Here, we demonstrated that the level of anthocyanin accumulation in dark blue, orange and red varieties was higher than in pale blue and pale pink varieties. Since dihydroflavonol 4-reductase (DFR) is a key enzyme in anthocyanin biosynthesis and accumulation in plants, we investigated the relationship between flower color intensity and the level of DFR gene expression. Six delphinium varieties with different flower colors were analyzed. Varieties that accumulated relatively high levels of anthocyanin also had high levels of DFR expression and enzyme activity in crude protein extracts. By contrast, DFR expression and activity was low in varieties with low anthocyanin accumulation. Alignment of DFR amino acid sequences in the six varieties showed the presence of two types, termed DgDFR and DnDFR. Recombinant DgDFR and DnDFR proteins had similar substrate specificities, but the kinetic turnover rate of the DnDFR enzyme was higher than that of DgDFR. We conclude that DFR expression level is closely correlated with flower color intensity and that DFR is an important factor that determines anthocyanin accumulation and delphinium flower color intensity.

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“…The aqueous layer was extracted with n-butanol (n-BuOH) to give n-BuOH-and H 2 O-soluble fractions. The EtOAc-and n-BuOH-soluble fractions were subjected to silica gel and octadecyl silica (ODS) column chromatography and finally to HPLC to furnish three new flavonoid glycosides, cissoside I (1, 0.0018% from natural medicine), cissoside II (2, 0.00029%), and cissoside III (3, 0.00038%); a new benzofuran-type stilbene, cissusin (4, 0.00054%); 18 flavonols, kaempferol (5, 0.0011%), 8) kaempferol-3-O-a-L-rhamnopyranoside (6, 0.00023%), 8) kaempferol-3-O-b-D-glucopyranoside (7, 0.00029%), 9) kaempferol-3-O-a-L-arabinofuranoside (8, 0.00024%), 8) kaempferol-7-O-a-L-rhamnopyranoside (9, 0.00065%), 10) kaempferol-3-O-a-L-rhamnopyranosyl-7-O-a-L-rhamnopyranoside (10, 0.010%), 8) kaempferol-3-O-b-D-glucopyranosyl-7-O-a-L-rhamnopyranoside (11, 0.00039%), 10) kaempferol-3-O-b-D-galactopyranosyl-7-Oa-L-rhamnopyranoside (12, 0.0010%), 11) kaempferol-3-…”

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Structures of New Flavonoids and Benzofuran-Type Stilbene and Degranulation Inhibitors of Rat Basophilic Leukemia Cells from the Brazilian Herbal Medicine Cissus sicyoides

Matsuda

Hata

et al. 2009

Chem. Pharm. Bull.

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Acylated kaempferol glycosides from the flowers of delphinium formosum

Cited by 39 publications

References 7 publications

Inhibitory Effects of the Constituents of <i>Hippophae rhamnoides</i> on 3T3-L1 Cell Differentiation and Nitric Oxide Production in RAW264.7 Cells

Inhibitory Effects of the Constituents of <i>Hippophae rhamnoides</i> on 3T3-L1 Cell Differentiation and Nitric Oxide Production in RAW264.7 Cells

Dihydroflavonol 4-reductase activity is associated with the intensity of flower colors in delphinium

Structures of New Flavonoids and Benzofuran-Type Stilbene and Degranulation Inhibitors of Rat Basophilic Leukemia Cells from the Brazilian Herbal Medicine Cissus sicyoides

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