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The effect of the aerial part of Lindera akoensis on lipopolysaccharides (LPS)-induced nitric oxide production in RAW264.7 cells.

Yang CP, Huang GJ, Huang HC, Chen YC, Chang CI, Wang SY, Chang HS, Tseng YH, Chien SC, Kuo YH - Int J Mol Sci (2013)

Bottom Line: Four new secondary metabolites, 3α-((E)-Dodec-1-enyl)-4β-hydroxy-5β-methyldihydrofuran-2-one (1), linderinol (6), 4'-O-methylkaempferol 3-O-α-L-(4''-E-p-coumaroyl)rhamnoside (11) and kaempferol 3-O-α-L-(4''-Z-p-coumaroyl)rhamnoside (12) with eleven known compounds-3-epilistenolide D1 (2), 3-epilistenolide D2 (3), (3Z,4α,5β)-3-(dodec-11-ynylidene)-4-hydroxy-5-methylbutanolide (4), (3E,4β,5β)-3-(dodec-11-ynylidene)-4-hydroxy-5-methylbutanolide (5), matairesinol (7), syringaresinol (8), (+)-pinoresinol (9), salicifoliol (10), 4''-p-coumaroylafzelin (13), catechin (14) and epicatechin (15)-were first isolated from the aerial part of Lindera akoensis.Their structures were determined by detailed analysis of 1D- and 2D-NMR spectroscopic data.All of the compounds isolated from Lindera akoensis showed that in vitro anti-inflammatory activity decreases the LPS-stimulated production of nitric oxide (NO) in RAW 264.7 cell, with IC50 values of 4.1-413.8 µM.

View Article: PubMed Central - PubMed

Affiliation: Department of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung 404, Taiwan. scchien@dragon.nchu.edu.tw.

ABSTRACT
Four new secondary metabolites, 3α-((E)-Dodec-1-enyl)-4β-hydroxy-5β-methyldihydrofuran-2-one (1), linderinol (6), 4'-O-methylkaempferol 3-O-α-L-(4''-E-p-coumaroyl)rhamnoside (11) and kaempferol 3-O-α-L-(4''-Z-p-coumaroyl)rhamnoside (12) with eleven known compounds-3-epilistenolide D1 (2), 3-epilistenolide D2 (3), (3Z,4α,5β)-3-(dodec-11-ynylidene)-4-hydroxy-5-methylbutanolide (4), (3E,4β,5β)-3-(dodec-11-ynylidene)-4-hydroxy-5-methylbutanolide (5), matairesinol (7), syringaresinol (8), (+)-pinoresinol (9), salicifoliol (10), 4''-p-coumaroylafzelin (13), catechin (14) and epicatechin (15)-were first isolated from the aerial part of Lindera akoensis. Their structures were determined by detailed analysis of 1D- and 2D-NMR spectroscopic data. All of the compounds isolated from Lindera akoensis showed that in vitro anti-inflammatory activity decreases the LPS-stimulated production of nitric oxide (NO) in RAW 264.7 cell, with IC50 values of 4.1-413.8 µM.

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The chromatograms of 1–15 on semi-preparative HPLC.
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f3-ijms-14-09168: The chromatograms of 1–15 on semi-preparative HPLC.

Mentions: The materials were totally dried under dark in air. The dried aerial part of L. akoensis (5.9 kg) was cut into small pieces and soaked in 95% ethanol (60 liter, 7 days × 3). After filtration, the crude extract was concentrated and stored under vacuum to yield an brown thick paste (337.8 g) that was suspended in H2O (1000 mL) and extracted with ethyl acetate (1000 mL, 3 times). The resulting ethyl acetate extract was concentrated to yield 127.8 g of a brown thick oil that was purified by 1900 g silica gel with a particle size 0.063–0.200 mm and an internal diameter of the column, 15 cm packed height, 25 cm chromatography, using a gradient of increasing polarity with n-hexane/ethyl acetate (99:1–0:100) as the mobile phase and separated into 21 fractions on the basis of TLC analysis for random isolation of compounds. Fraction 11 (5.08 g) was re-separated by chromatography and semi-preparative HPLC with 40% EtOAc in n-hexane to afford pure, butanolide 1 (6.1 mg, 0.00104‰), 2 (7.7 mg, 0.00131‰), 3 (7.8 mg, 0.00132‰) and 4 (2.1 mg, 0.00036‰) and 5 (1.6 mg, 0.00027‰). Fraction 15 (6.82 g) was re-separated by chromatography and semi-preparative HPLC with 50% EtOAc in n-hexane to afford pure lignans 7 (2.3 mg, 0.00039‰), 9 (1.5 mg, 0.00025‰) and 10 (1.2 mg, 0.00020‰). Fraction 16 (7.15 g) was re-separated by chromatography and semi-preparative HPLC with 60% EtOAc in n-hexane to afford pure lignans 6 (8.3 mg, 0.00141‰), 8 (15.8 mg, 0.00268‰), 11 (16.6 mg, 0.00281‰), 12 (8.9 mg, 0.00151‰), 13 (38.3 mg, 0.00649‰), 14 (62.3 mg, 0.01056‰) and 15 (2.2 mg, 0.00037‰). The flow of semi-preparative HPLC was 1.5 mL/min, the chromatograms of compounds showed on Figure 3.


The effect of the aerial part of Lindera akoensis on lipopolysaccharides (LPS)-induced nitric oxide production in RAW264.7 cells.

Yang CP, Huang GJ, Huang HC, Chen YC, Chang CI, Wang SY, Chang HS, Tseng YH, Chien SC, Kuo YH - Int J Mol Sci (2013)

The chromatograms of 1–15 on semi-preparative HPLC.
© Copyright Policy - open-access
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC3676778&req=5

f3-ijms-14-09168: The chromatograms of 1–15 on semi-preparative HPLC.
Mentions: The materials were totally dried under dark in air. The dried aerial part of L. akoensis (5.9 kg) was cut into small pieces and soaked in 95% ethanol (60 liter, 7 days × 3). After filtration, the crude extract was concentrated and stored under vacuum to yield an brown thick paste (337.8 g) that was suspended in H2O (1000 mL) and extracted with ethyl acetate (1000 mL, 3 times). The resulting ethyl acetate extract was concentrated to yield 127.8 g of a brown thick oil that was purified by 1900 g silica gel with a particle size 0.063–0.200 mm and an internal diameter of the column, 15 cm packed height, 25 cm chromatography, using a gradient of increasing polarity with n-hexane/ethyl acetate (99:1–0:100) as the mobile phase and separated into 21 fractions on the basis of TLC analysis for random isolation of compounds. Fraction 11 (5.08 g) was re-separated by chromatography and semi-preparative HPLC with 40% EtOAc in n-hexane to afford pure, butanolide 1 (6.1 mg, 0.00104‰), 2 (7.7 mg, 0.00131‰), 3 (7.8 mg, 0.00132‰) and 4 (2.1 mg, 0.00036‰) and 5 (1.6 mg, 0.00027‰). Fraction 15 (6.82 g) was re-separated by chromatography and semi-preparative HPLC with 50% EtOAc in n-hexane to afford pure lignans 7 (2.3 mg, 0.00039‰), 9 (1.5 mg, 0.00025‰) and 10 (1.2 mg, 0.00020‰). Fraction 16 (7.15 g) was re-separated by chromatography and semi-preparative HPLC with 60% EtOAc in n-hexane to afford pure lignans 6 (8.3 mg, 0.00141‰), 8 (15.8 mg, 0.00268‰), 11 (16.6 mg, 0.00281‰), 12 (8.9 mg, 0.00151‰), 13 (38.3 mg, 0.00649‰), 14 (62.3 mg, 0.01056‰) and 15 (2.2 mg, 0.00037‰). The flow of semi-preparative HPLC was 1.5 mL/min, the chromatograms of compounds showed on Figure 3.

Bottom Line: Four new secondary metabolites, 3α-((E)-Dodec-1-enyl)-4β-hydroxy-5β-methyldihydrofuran-2-one (1), linderinol (6), 4'-O-methylkaempferol 3-O-α-L-(4''-E-p-coumaroyl)rhamnoside (11) and kaempferol 3-O-α-L-(4''-Z-p-coumaroyl)rhamnoside (12) with eleven known compounds-3-epilistenolide D1 (2), 3-epilistenolide D2 (3), (3Z,4α,5β)-3-(dodec-11-ynylidene)-4-hydroxy-5-methylbutanolide (4), (3E,4β,5β)-3-(dodec-11-ynylidene)-4-hydroxy-5-methylbutanolide (5), matairesinol (7), syringaresinol (8), (+)-pinoresinol (9), salicifoliol (10), 4''-p-coumaroylafzelin (13), catechin (14) and epicatechin (15)-were first isolated from the aerial part of Lindera akoensis.Their structures were determined by detailed analysis of 1D- and 2D-NMR spectroscopic data.All of the compounds isolated from Lindera akoensis showed that in vitro anti-inflammatory activity decreases the LPS-stimulated production of nitric oxide (NO) in RAW 264.7 cell, with IC50 values of 4.1-413.8 µM.

View Article: PubMed Central - PubMed

Affiliation: Department of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung 404, Taiwan. scchien@dragon.nchu.edu.tw.

ABSTRACT
Four new secondary metabolites, 3α-((E)-Dodec-1-enyl)-4β-hydroxy-5β-methyldihydrofuran-2-one (1), linderinol (6), 4'-O-methylkaempferol 3-O-α-L-(4''-E-p-coumaroyl)rhamnoside (11) and kaempferol 3-O-α-L-(4''-Z-p-coumaroyl)rhamnoside (12) with eleven known compounds-3-epilistenolide D1 (2), 3-epilistenolide D2 (3), (3Z,4α,5β)-3-(dodec-11-ynylidene)-4-hydroxy-5-methylbutanolide (4), (3E,4β,5β)-3-(dodec-11-ynylidene)-4-hydroxy-5-methylbutanolide (5), matairesinol (7), syringaresinol (8), (+)-pinoresinol (9), salicifoliol (10), 4''-p-coumaroylafzelin (13), catechin (14) and epicatechin (15)-were first isolated from the aerial part of Lindera akoensis. Their structures were determined by detailed analysis of 1D- and 2D-NMR spectroscopic data. All of the compounds isolated from Lindera akoensis showed that in vitro anti-inflammatory activity decreases the LPS-stimulated production of nitric oxide (NO) in RAW 264.7 cell, with IC50 values of 4.1-413.8 µM.

Show MeSH