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Phenolic compounds from Halimodendron halodendron (Pall.) voss and their antimicrobial and antioxidant activities.

Wang J, Lou J, Luo C, Zhou L, Wang M, Wang L - Int J Mol Sci (2012)

Bottom Line: All these phenolic compounds showed significant antimicrobial activity with a broad spectrum as well as antioxidant activity based on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging and β-carotene-linoleic acid bleaching assays.In general, the flavonol aglycones with relatively low polarity exhibited stronger activities than the glycosides.The results suggest the potential of this plant as a source of functional food ingredients and provide support data for its utilization as forage as well.

View Article: PubMed Central - PubMed

Affiliation: College of Agronomy and Biotechnology, China Agricultural University, Beijing 100193, China; E-Mails: nxwjh8121@sina.com (J.W.); azaazafighting88@163.com (J.L.); luochaobest@163.com (C. L.).

ABSTRACT
Halimodendron halodendron has been used as forage in northwestern China for a long time. Its young leaves and flowers are edible and favored by indigenous people. In this study, eleven phenolic compounds were bioassay-guided and isolated from the aerial parts of H. halodendron for the first time. They were identified by means of physicochemical and spectrometric analysis as quercetin (1), 3,5,7,8,4'-pentahydroxy-3'-methoxy flavone (2), 3-O-methylquercetin (3), 3,3'-di-O-methylquercetin (4), 3,3'-di-O-methylquercetin-7-O-β-d-glucopyranoside (5), isorhamentin-3-O-β-d-rutinoside (6), 8-O-methylretusin (7), 8-O-methylretusin-7-O-β-d-glucopyranoside (8), salicylic acid (9), p-hydroxybenzoic acid (ferulic acid) (10), and 4-hydroxy-3-methoxy cinnamic acid (11). They were sorted as flavonols (1-6), soflavones (7 and 8), and phenolic acids (9-11). Among the compounds, flanools 1-4 revealed a strong antibacterial activity with minimum inhibitory concentration (MIC) values of 50-150 μg/mL, and median inhibitory concentration (IC(50)) values of 26.8-125.1 μg/mL. The two isoflavones (7 and 8) showed moderate inhibitory activity on the test bacteria. Three phenolic acids (9, 10 and 11) showed strong antibacterial activity with IC(50) values of 28.1-149.7 μg/mL. Antifungal activities of the compounds were similar to their antibacterial activities. All these phenolic compounds showed significant antimicrobial activity with a broad spectrum as well as antioxidant activity based on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging and β-carotene-linoleic acid bleaching assays. In general, the flavonol aglycones with relatively low polarity exhibited stronger activities than the glycosides. The results suggest the potential of this plant as a source of functional food ingredients and provide support data for its utilization as forage as well.

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Chemical structures of the compounds (1–11).
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f1-ijms-13-11349: Chemical structures of the compounds (1–11).

Mentions: Eleven compounds were bioassay-guided and isolated from the crude ethanol extract of H. halodendron (aerial parts) and characterized based on the physicochemical properties and spectral data. Their chemical structures were elucidated based on the spectral data and comparison of the properties and spectral characteristics with those in the literature, which were all known compounds and confirmed as quercetin (1) [21], 3,5,7,8,4′-pentahydroxy-3′-methoxy flavone (2) [22], 3-O-methylquercetin (3) [23], 3,3′-di-O-methylquercetin (4) [24], 3,3′-di-O-methylquercetin-7-O-β-d-glucopyranoside (5) [25], isorhamentin-3-O-β-d-rutinoside (6) [26], 8-O-methylretusin (7) [27], 8-O-methylretusin-7-O-β-d-glucopyranoside (8) [28], salicylic acid (9) [9], p-hydroxybenzoic acid (10) [29], and 4-hydroxy-3-methoxy cinnamic acid (ferulic acid) (11) [30] (Figure 1). Of the 11 compounds, 1–6 were flavonol derivatives, 7 and 8 were isoflavone derivatives, and 9, 10 and 11 were phenolic acids. Compound 6 should be derived from 4 with the methoxy group at Position 3 being substituted by rutinose, Compound 8 derived from 7 with the hydroxyl group at Position 7 glycosilated with glucose, and Compound 5 derived from 4 with the hydroxyl group at Position 7 glycosilated with glucose.


Phenolic compounds from Halimodendron halodendron (Pall.) voss and their antimicrobial and antioxidant activities.

Wang J, Lou J, Luo C, Zhou L, Wang M, Wang L - Int J Mol Sci (2012)

Chemical structures of the compounds (1–11).
© Copyright Policy - open-access
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC3472750&req=5

f1-ijms-13-11349: Chemical structures of the compounds (1–11).
Mentions: Eleven compounds were bioassay-guided and isolated from the crude ethanol extract of H. halodendron (aerial parts) and characterized based on the physicochemical properties and spectral data. Their chemical structures were elucidated based on the spectral data and comparison of the properties and spectral characteristics with those in the literature, which were all known compounds and confirmed as quercetin (1) [21], 3,5,7,8,4′-pentahydroxy-3′-methoxy flavone (2) [22], 3-O-methylquercetin (3) [23], 3,3′-di-O-methylquercetin (4) [24], 3,3′-di-O-methylquercetin-7-O-β-d-glucopyranoside (5) [25], isorhamentin-3-O-β-d-rutinoside (6) [26], 8-O-methylretusin (7) [27], 8-O-methylretusin-7-O-β-d-glucopyranoside (8) [28], salicylic acid (9) [9], p-hydroxybenzoic acid (10) [29], and 4-hydroxy-3-methoxy cinnamic acid (ferulic acid) (11) [30] (Figure 1). Of the 11 compounds, 1–6 were flavonol derivatives, 7 and 8 were isoflavone derivatives, and 9, 10 and 11 were phenolic acids. Compound 6 should be derived from 4 with the methoxy group at Position 3 being substituted by rutinose, Compound 8 derived from 7 with the hydroxyl group at Position 7 glycosilated with glucose, and Compound 5 derived from 4 with the hydroxyl group at Position 7 glycosilated with glucose.

Bottom Line: All these phenolic compounds showed significant antimicrobial activity with a broad spectrum as well as antioxidant activity based on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging and β-carotene-linoleic acid bleaching assays.In general, the flavonol aglycones with relatively low polarity exhibited stronger activities than the glycosides.The results suggest the potential of this plant as a source of functional food ingredients and provide support data for its utilization as forage as well.

View Article: PubMed Central - PubMed

Affiliation: College of Agronomy and Biotechnology, China Agricultural University, Beijing 100193, China; E-Mails: nxwjh8121@sina.com (J.W.); azaazafighting88@163.com (J.L.); luochaobest@163.com (C. L.).

ABSTRACT
Halimodendron halodendron has been used as forage in northwestern China for a long time. Its young leaves and flowers are edible and favored by indigenous people. In this study, eleven phenolic compounds were bioassay-guided and isolated from the aerial parts of H. halodendron for the first time. They were identified by means of physicochemical and spectrometric analysis as quercetin (1), 3,5,7,8,4'-pentahydroxy-3'-methoxy flavone (2), 3-O-methylquercetin (3), 3,3'-di-O-methylquercetin (4), 3,3'-di-O-methylquercetin-7-O-β-d-glucopyranoside (5), isorhamentin-3-O-β-d-rutinoside (6), 8-O-methylretusin (7), 8-O-methylretusin-7-O-β-d-glucopyranoside (8), salicylic acid (9), p-hydroxybenzoic acid (ferulic acid) (10), and 4-hydroxy-3-methoxy cinnamic acid (11). They were sorted as flavonols (1-6), soflavones (7 and 8), and phenolic acids (9-11). Among the compounds, flanools 1-4 revealed a strong antibacterial activity with minimum inhibitory concentration (MIC) values of 50-150 μg/mL, and median inhibitory concentration (IC(50)) values of 26.8-125.1 μg/mL. The two isoflavones (7 and 8) showed moderate inhibitory activity on the test bacteria. Three phenolic acids (9, 10 and 11) showed strong antibacterial activity with IC(50) values of 28.1-149.7 μg/mL. Antifungal activities of the compounds were similar to their antibacterial activities. All these phenolic compounds showed significant antimicrobial activity with a broad spectrum as well as antioxidant activity based on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging and β-carotene-linoleic acid bleaching assays. In general, the flavonol aglycones with relatively low polarity exhibited stronger activities than the glycosides. The results suggest the potential of this plant as a source of functional food ingredients and provide support data for its utilization as forage as well.

Show MeSH