Carbon-13 NMR studies of flavonoids—I

Ternai, B.; Markham, Kenneth R.

doi:10.1016/s0040-4020(01)93772-x

Cited by 156 publications

(73 citation statements)

References 7 publications

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“…1 H NMR and 13 C NMR spectra of compound 2 were compared with those of apigenin [5,7-dihydroxy-2-(4?-hydroxyphenyl)-4H-1-benzopyran-4-one]. 25,26) Compound 2 was identiˆed as apigenin from these spectral data and physical properties. .…”

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confidence: 99%

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Antimutagenic Activity of Flavonoids fromChrysanthemum morifolium

Miyazawa

Hisama

2003

Bioscience, Biotechnology, and Biochemistry

196

113

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A methanol extract from the ‰ower heads of Chrysanthemum morifolium showed a suppressive eŠect on umu gene expression of the SOS response in Salmonella typhimurium TA1535 W pSK1002 against the mutagen 2-(2-furyl)-3-(5-nitro-2-furyl)acrylamide (furylfuramide). The methanol extract was re-extracted with hexane, chloroform, ethyl acetate, butanol, and water. The ethyl acetate fraction showed a suppressive eŠect. Suppressive compounds in the ethyl acetate fraction were isolated by silica gel column chromatography and identiˆed as the ‰avonoids acacetin (1), apigenin (2), luteolin (3), and quercetin (4) by EI-MS, IR, and 1 H and 13 C NMR spectroscopy. Compounds 1-4 suppressed the furylfuramide-induced SOS response in the umu test. Compounds 1-4 suppressed 60.2, 75.7, 90.0, and 66.6z of the SOS-inducing activity at a concentration of 0.70 mmol W ml. The ID 50 (50z inhibitory dose) values of 1-4 were 0.62, 0.55, 0.44, and 0.59 mmol W ml. These compounds had the suppressive eŠects on umu gene expression of the SOS response against other mutagens, 4-nitroquinolin 1-oxide (4NQO) and N-methyl-N?-nitro-N-nitrosoguanidine (MNNG), which do not require liver-metabolizing enzymes. These compounds also showed the suppression of SOS-inducing activity against the other mutagens a‰atoxin B 1 (AfB 1 ) and 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1), which require liver-metabolizing enzymes, and UV irradiation. In addition to the antimutagenic activities of these compounds against furylfuramide, Trp-P-1 and activated Trp-P-1 were also assayed by the Ames test using S. typhimurium TA100.

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confidence: 99%

“…. 26,27) Compound 3 was identiˆed as luteolin from these spectral data and physical properties. 28) Compound 4 was identiˆed as quercetin from these spectral data and physical properties.…”

Section: )mentioning

confidence: 99%

Antimutagenic Activity of Flavonoids fromChrysanthemum morifolium

Miyazawa

Hisama

2003

Bioscience, Biotechnology, and Biochemistry

196

113

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“…The structures of the isolated compounds were determined to be kaempferol-3,4' -O-dimethylether (3), kaempferol-3-O-methylether (4), kaempferol-3-O-(3,4-Odiacetyl-a-L-rhamnopyranoside) (6) and kaempferol-3-0-(2,4-O-diacetyl-<z-L-rhamnopyranoside) (7). The stability of the two flavonoid glycosides (6 and 7) and their occurrence in the fresh rhizome are also discussed.…”

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“…After standing for 1 hr at 23°C, the solvent was removed in vacuo to give 9. By the same procedure, 9 was also obtained from 7 Re-extraction of the rhizomes ofZingiber zerumbet. Fresh samples of the rhizomes (10g each) were crushed and immersed in either MeOHor acetone for one week at 23°C.…”

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Flavonoid constituents of Zingiber zerumbet Smith.

Nakatani

Jitoe

Masuda

et al. 1991

Agricultural and Biological Chemistry

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“…Structure characterization of these compounds was carried out by interpretation of their spectral data and comparison with the data reported in the literature. Compounds 4-9 were identifi ed as kaempferol-3-O-L-rhamnopyranoside (4) [Hur et al, 2001;Jang et al, 2002] [Kim et al, 1992;Hasan et al, 1995], isorhamnetin-3-O-glucopyranoside (6) [Kim et al, 1998], quer cetin-3-O-α-L-rhamnopyranoside (7) [Lee et al, 2007] [Hong et al, 2008], and quercetin (9) [Ternai and Markham 1976;Lee et al, 1997;Lee et al, 2007], respectively.…”

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confidence: 99%

Antioxidative Constituents of the Aerial Parts of Galium spurium

Yang¹,

Park²,

Ahn³

et al. 2011

Biomolecules and Therapeutics

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Reactive oxygen species (ROS), in the form of superoxide anion(O 2 − ), hydroxyl radical (·OH) and hydrogen peroxide (H 2 O 2 ), are generated in living organisms through many pathways (Chung et al., 2005). An imbalance between production of ROS and their elimination in the organisms cause oxidative stress (Monika et al., 2010). Oxidative stress has been implicated as a possible factor in the etiology of several human diseases, including cancer, cardiovascular disease, Alzheimer's disease and aging (Suganya et al., 2007). Antioxidants are the important defense factors against oxidative stress caused by ROS. However, the use of synthetic antioxidant components, such as butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT), has been limited because of their possible toxic and carcinogenic effects (Branen, 1975). Thus, there is a growing interest in fi nding natural herbal plants with low in toxicity and high in radical scavenging activity (Branen, 1975). In the course of screening for antioxidant from Korean natural plants by measuring the radical scavenging effect on 1,1-diphenyl-2-picrylhydrazyl (DPPH), a total extract of the Galium spurium L. (Rubiaceae) was found to show a potent antioxidant activity. G. spurium is annual or biannual plant. Phytochemical studies on the genus have shown it to be chemically diverse, yielding among others, triterpenoid saponins, iridoidAs part of an ongoing search for natural plants with antioxidant compounds by measuring the radical scavenging effect on 1,1-diphenyl-2-picrylhydrazyl (DPPH), a total extract of the twigs of Galium spurium L. (Rubiaceae) was found to show potent antioxidant activity. Subsequent activity-guided fractionation of the methanolic extract led to the isolation of nine compounds, asperulosidic acid methyl ester (1), asperuloside (2), caffeic acid ( (8), and quercetin (9). Their structures were elucidated by spectroscopic studies. Compounds 1, 3-8 were isolated for the fi rst time from this plant. Among them, compounds 3 and 9 showed the signifi cant radical scavenging effects on DPPH, and compounds 3 and 7 showed the potent ribofl avin originated superoxide quenching activities. et al., 2000). Some iridoids (Deliorman et al., 2001), anthraquinones (Koyama et al., 1993) and fl avonoids (Cai et al., 2009) were analyzed from G. spurium. Its aerial parts have been used for the treatment of the bones and sinews pain and hematuria. Crude extract of G. spurium was also used as a anticancer agent in folk medicine. It has been reported to have immunostimulant and anti-tumor activity (Yoon et al., 2005). However, information concerning the antioxidant activity of G. spurium is unavailable. This paper deals with the isolation and structural characterization of these compounds and their scavenging activity of the stable DPPH free radical and superoxide quenching activities.

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Carbon-13 NMR studies of flavonoids—I

Cited by 156 publications

References 7 publications

Antimutagenic Activity of Flavonoids fromChrysanthemum morifolium

Antimutagenic Activity of Flavonoids fromChrysanthemum morifolium

Flavonoid constituents of Zingiber zerumbet Smith.

Antioxidative Constituents of the Aerial Parts of Galium spurium

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