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Anti-inflammatory effects of apo-9'-fucoxanthinone from the brown alga, Sargassum muticum.

Yang EJ, Ham YM, Lee WJ, Lee NH, Hyun CG - Daru (2013)

Bottom Line: S. muticum is a traditional Korean food stuff and has pharmacological functions including anti-inflammatory effects.Apo-9'-fucoxanthinone effectively suppressed LPS-induced nitric oxide (NO) and prostaglandin E2 (PGE2) production.This is the first report describing effective anti-inflammatory activity for apo-9'-fucoxanthinone'-fucoxanthnone isolated from S. muticum.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, Cosmetic Science Center, Jeju National University, Jeju 690-756, Korea. cghyun@jejunu.ac.kr.

ABSTRACT

Background: The marine environment is a unique source of bioactive natural products, of which Sargassum muticum (Yendo) Fensholt is an important brown algae distributed in Jeju Island, Korea. S. muticum is a traditional Korean food stuff and has pharmacological functions including anti-inflammatory effects. However, the active ingredients from S. muticum have not been characterized.

Methods: Bioguided fractionation of the ethanolic extract of S. muticum, collected from Jeju island, led to the isolation of a norisoprenoid. Its structure was determined by analysis of the spectroscopic data. In vitro anti-inflammatory activity and mechanisms of action of this compound were examined using lipopolysaccharide (LPS)-stimulated RAW 264.7 cells through ELISA assays and Western blot analysis.

Results: Apo-9'-fucoxanthinone, belonging to the norisoprenoid family were identified. Apo-9'-fucoxanthinone effectively suppressed LPS-induced nitric oxide (NO) and prostaglandin E2 (PGE2) production. This compound also exerted their anti-inflammatory actions by down-regulating of NF-κB activation via suppression of IκB-α in macrophages.

Conclusions: This is the first report describing effective anti-inflammatory activity for apo-9'-fucoxanthinone'-fucoxanthnone isolated from S. muticum. Apo-9'-fucoxanthinone may be a good candidate for delaying the progression of human inflammatory diseases and warrants further studies.

No MeSH data available.


Related in: MedlinePlus

L The structure of Apo-9′-fucoxanthinone.
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Figure 1: L The structure of Apo-9′-fucoxanthinone.

Mentions: S. muticum was collected from the coasts of Jeju Island in March 2009, and verified by Dr. Wook Jae Lee at Jeju Technopark (JTP). A voucher specimen (CSC-002) was deposited at Department of Chemistry, Jeju National University, Jeju, Korea. S. muticum were washed 3 times with water to remove any salt, epiphytes, and sand attached to the surface. They were dried at 60°C for 24 h in an oven, and pulverized in a grinder prior to extraction. The dried powder (800 g) was extracted with 70% aqueous ethanol with stirring for 2 days at room temperature. The filtrate was concentrated under reduced pressure. The extract (105 g) was suspended in water (1.0 L), and successively partitioned into n-hexane, methylene chloride, ethyl acetate, and n-butanol fractions. The fraction of methylene chloride (7 g), being dissolved in solvent, mixed with celite, and evaporated using a rotary vacuum evaporator. After lyophilization, it was chromatographed and eluted by using the solvents 500 mL of into n-hexane, methylene chloride/ethyl acetate (10:1, 5:1, 2:1), methylene chloride, ethyl acetate, and methanol in order. The hexane fraction was chromatographed over a silica gel column using n-hexane:EtOAc (3:1) in order to obtain 10 sub-fractions (F-1 to F-10). All fractions containing the same constituent(s) identified on the TLC plates were combined and the solvents were evaporated using a rotary vacuum evaporator. Structures of fraction 10 of them (F10, 2.3 g) were determined using proton-nuclear magnetic resonance (1H NMR) and 13C NMR. The compound’s structural identity was determined by one-and two-dimensional nuclear magnetic resonance (NMR) spectroscopic analysis (Additional file 1) and comparison to published values. Structures of these compounds are given in Figure 1.


Anti-inflammatory effects of apo-9'-fucoxanthinone from the brown alga, Sargassum muticum.

Yang EJ, Ham YM, Lee WJ, Lee NH, Hyun CG - Daru (2013)

L The structure of Apo-9′-fucoxanthinone.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3733608&req=5

Figure 1: L The structure of Apo-9′-fucoxanthinone.
Mentions: S. muticum was collected from the coasts of Jeju Island in March 2009, and verified by Dr. Wook Jae Lee at Jeju Technopark (JTP). A voucher specimen (CSC-002) was deposited at Department of Chemistry, Jeju National University, Jeju, Korea. S. muticum were washed 3 times with water to remove any salt, epiphytes, and sand attached to the surface. They were dried at 60°C for 24 h in an oven, and pulverized in a grinder prior to extraction. The dried powder (800 g) was extracted with 70% aqueous ethanol with stirring for 2 days at room temperature. The filtrate was concentrated under reduced pressure. The extract (105 g) was suspended in water (1.0 L), and successively partitioned into n-hexane, methylene chloride, ethyl acetate, and n-butanol fractions. The fraction of methylene chloride (7 g), being dissolved in solvent, mixed with celite, and evaporated using a rotary vacuum evaporator. After lyophilization, it was chromatographed and eluted by using the solvents 500 mL of into n-hexane, methylene chloride/ethyl acetate (10:1, 5:1, 2:1), methylene chloride, ethyl acetate, and methanol in order. The hexane fraction was chromatographed over a silica gel column using n-hexane:EtOAc (3:1) in order to obtain 10 sub-fractions (F-1 to F-10). All fractions containing the same constituent(s) identified on the TLC plates were combined and the solvents were evaporated using a rotary vacuum evaporator. Structures of fraction 10 of them (F10, 2.3 g) were determined using proton-nuclear magnetic resonance (1H NMR) and 13C NMR. The compound’s structural identity was determined by one-and two-dimensional nuclear magnetic resonance (NMR) spectroscopic analysis (Additional file 1) and comparison to published values. Structures of these compounds are given in Figure 1.

Bottom Line: S. muticum is a traditional Korean food stuff and has pharmacological functions including anti-inflammatory effects.Apo-9'-fucoxanthinone effectively suppressed LPS-induced nitric oxide (NO) and prostaglandin E2 (PGE2) production.This is the first report describing effective anti-inflammatory activity for apo-9'-fucoxanthinone'-fucoxanthnone isolated from S. muticum.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, Cosmetic Science Center, Jeju National University, Jeju 690-756, Korea. cghyun@jejunu.ac.kr.

ABSTRACT

Background: The marine environment is a unique source of bioactive natural products, of which Sargassum muticum (Yendo) Fensholt is an important brown algae distributed in Jeju Island, Korea. S. muticum is a traditional Korean food stuff and has pharmacological functions including anti-inflammatory effects. However, the active ingredients from S. muticum have not been characterized.

Methods: Bioguided fractionation of the ethanolic extract of S. muticum, collected from Jeju island, led to the isolation of a norisoprenoid. Its structure was determined by analysis of the spectroscopic data. In vitro anti-inflammatory activity and mechanisms of action of this compound were examined using lipopolysaccharide (LPS)-stimulated RAW 264.7 cells through ELISA assays and Western blot analysis.

Results: Apo-9'-fucoxanthinone, belonging to the norisoprenoid family were identified. Apo-9'-fucoxanthinone effectively suppressed LPS-induced nitric oxide (NO) and prostaglandin E2 (PGE2) production. This compound also exerted their anti-inflammatory actions by down-regulating of NF-κB activation via suppression of IκB-α in macrophages.

Conclusions: This is the first report describing effective anti-inflammatory activity for apo-9'-fucoxanthinone'-fucoxanthnone isolated from S. muticum. Apo-9'-fucoxanthinone may be a good candidate for delaying the progression of human inflammatory diseases and warrants further studies.

No MeSH data available.


Related in: MedlinePlus