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Bioactive chemical constituents from the brown alga Homoeostrichus formosana.

Fang HY, Chokkalingam U, Chiou SF, Hwang TL, Chen SL, Wang WL, Sheu JH - Int J Mol Sci (2014)

Bottom Line: The structure of 1 was determined by extensive 1D and 2D spectroscopic analyses.Acetylation of 1 yielded the monoacetylated derivative 2-(4',8'-dimethylnona-3'E,7'-dienyl)-8-acetyl-2,6-dimethyl-2H-chromene (6).Compound 2 was found to display potent in vitro anti-inflammatory activity by inhibiting the generation of superoxide anion (IC50 0.22 ± 0.03 μg/mL) and elastase release (IC50 0.48 ± 0.11 μg/mL) in FMLP/CB-induced human neutrophils.

View Article: PubMed Central - PubMed

Affiliation: Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 80424, Taiwan. ahui0220@yahoo.com.tw.

ABSTRACT
A new chromene derivative, 2-(4',8'-dimethylnona-3'E,7'-dienyl)-8-hydroxy-2,6-dimethyl-2H-chromene (1) together with four known natural products, methylfarnesylquinone (2), isololiolide (3), pheophytin a (4), and β-carotene (5) were isolated from the brown alga Homoeostrichus formosana. The structure of 1 was determined by extensive 1D and 2D spectroscopic analyses. Acetylation of 1 yielded the monoacetylated derivative 2-(4',8'-dimethylnona-3'E,7'-dienyl)-8-acetyl-2,6-dimethyl-2H-chromene (6). Compounds 1-6 exhibited various levels of cytotoxic, antibacterial, and anti-inflammatory activities. Compound 2 was found to display potent in vitro anti-inflammatory activity by inhibiting the generation of superoxide anion (IC50 0.22 ± 0.03 μg/mL) and elastase release (IC50 0.48 ± 0.11 μg/mL) in FMLP/CB-induced human neutrophils.

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Structures of metabolites 1–6.
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ijms-16-00736-f001: Structures of metabolites 1–6.

Mentions: In continuation of our search for bioactive chemical constituents from marine alga [1,2,3,4,5,6], we found that a crude acetone extract of Homoeostrichus formosana (Dictyotaceae, Phaeophyceae) [7] displayed significant cytotoxic and anti-inflammatory properties. A novel chromene 2-(4',8'-dimethylnona-3'E,7'-dienyl)-8-hydroxy-2,6-dimethyl-2H-chromene (1), along with four known compounds methylfarnesylquinone (2) [8], isololiolide (3) [9], pheophytin a (4) [10,11], and β-carotene (5) [12] (Chart 1) were identified for the first time using a bioassay-directed fractionation method. Meroterpenoids of the chromene skeleton and related structural units incorporated with a polyprenyl chain, are particularly abundant in brown alga (division Phaeophyta), which makes chromenes one of the representative groups of secondary metabolites of these organisms [13,14,15]. 2-Substituted 2H-chromenes and their analogs are pervasive molecular structures in chemistry, biology, and medicine. Many of these compounds possess various interesting biological properties that includes antidiabetic [16], cytotoxic [17], antifungal [18], anti-HIV [19], antibacterial [20], antitumor [21] and potent antioxidant (vitamin E) [22,23] activities. Recently, we also reported cytotoxic, anti-inflammatory, and antibacterial properties of sulfur-containing polybromoindoles from the Formosan red alga Laurencia brongniartii [24]. Consequently, the study has been undertaken to assess the cytotoxic, antibacterial, and anti-inflammatory activities of isolated compounds 1–6. Compounds 1, 2, and 4–6 were tested for cytotoxicity against HepG2, A-549, and MDA-MB-231 cancer cell lines as well as antibacterial activity against Bacillus cereus, Staphylococcus aureus, Salmonella typhimurium, Pseudomonas aeruginosa, Serratia marcescens and Yersinia entercocolitica. The abilities of 1, 2, 5, and 6 to inhibit superoxide anion generation and elastase release in FMLP/CB induced human neutrophils were also studied. Herein, we describe the isolation and structure elucidation of compound 1, and the results of biological activity assays of compounds 1–6.


Bioactive chemical constituents from the brown alga Homoeostrichus formosana.

Fang HY, Chokkalingam U, Chiou SF, Hwang TL, Chen SL, Wang WL, Sheu JH - Int J Mol Sci (2014)

Structures of metabolites 1–6.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4307272&req=5

ijms-16-00736-f001: Structures of metabolites 1–6.
Mentions: In continuation of our search for bioactive chemical constituents from marine alga [1,2,3,4,5,6], we found that a crude acetone extract of Homoeostrichus formosana (Dictyotaceae, Phaeophyceae) [7] displayed significant cytotoxic and anti-inflammatory properties. A novel chromene 2-(4',8'-dimethylnona-3'E,7'-dienyl)-8-hydroxy-2,6-dimethyl-2H-chromene (1), along with four known compounds methylfarnesylquinone (2) [8], isololiolide (3) [9], pheophytin a (4) [10,11], and β-carotene (5) [12] (Chart 1) were identified for the first time using a bioassay-directed fractionation method. Meroterpenoids of the chromene skeleton and related structural units incorporated with a polyprenyl chain, are particularly abundant in brown alga (division Phaeophyta), which makes chromenes one of the representative groups of secondary metabolites of these organisms [13,14,15]. 2-Substituted 2H-chromenes and their analogs are pervasive molecular structures in chemistry, biology, and medicine. Many of these compounds possess various interesting biological properties that includes antidiabetic [16], cytotoxic [17], antifungal [18], anti-HIV [19], antibacterial [20], antitumor [21] and potent antioxidant (vitamin E) [22,23] activities. Recently, we also reported cytotoxic, anti-inflammatory, and antibacterial properties of sulfur-containing polybromoindoles from the Formosan red alga Laurencia brongniartii [24]. Consequently, the study has been undertaken to assess the cytotoxic, antibacterial, and anti-inflammatory activities of isolated compounds 1–6. Compounds 1, 2, and 4–6 were tested for cytotoxicity against HepG2, A-549, and MDA-MB-231 cancer cell lines as well as antibacterial activity against Bacillus cereus, Staphylococcus aureus, Salmonella typhimurium, Pseudomonas aeruginosa, Serratia marcescens and Yersinia entercocolitica. The abilities of 1, 2, 5, and 6 to inhibit superoxide anion generation and elastase release in FMLP/CB induced human neutrophils were also studied. Herein, we describe the isolation and structure elucidation of compound 1, and the results of biological activity assays of compounds 1–6.

Bottom Line: The structure of 1 was determined by extensive 1D and 2D spectroscopic analyses.Acetylation of 1 yielded the monoacetylated derivative 2-(4',8'-dimethylnona-3'E,7'-dienyl)-8-acetyl-2,6-dimethyl-2H-chromene (6).Compound 2 was found to display potent in vitro anti-inflammatory activity by inhibiting the generation of superoxide anion (IC50 0.22 ± 0.03 μg/mL) and elastase release (IC50 0.48 ± 0.11 μg/mL) in FMLP/CB-induced human neutrophils.

View Article: PubMed Central - PubMed

Affiliation: Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 80424, Taiwan. ahui0220@yahoo.com.tw.

ABSTRACT
A new chromene derivative, 2-(4',8'-dimethylnona-3'E,7'-dienyl)-8-hydroxy-2,6-dimethyl-2H-chromene (1) together with four known natural products, methylfarnesylquinone (2), isololiolide (3), pheophytin a (4), and β-carotene (5) were isolated from the brown alga Homoeostrichus formosana. The structure of 1 was determined by extensive 1D and 2D spectroscopic analyses. Acetylation of 1 yielded the monoacetylated derivative 2-(4',8'-dimethylnona-3'E,7'-dienyl)-8-acetyl-2,6-dimethyl-2H-chromene (6). Compounds 1-6 exhibited various levels of cytotoxic, antibacterial, and anti-inflammatory activities. Compound 2 was found to display potent in vitro anti-inflammatory activity by inhibiting the generation of superoxide anion (IC50 0.22 ± 0.03 μg/mL) and elastase release (IC50 0.48 ± 0.11 μg/mL) in FMLP/CB-induced human neutrophils.

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