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Comparative Study
. 2012 Dec 10;10(12):2766-81.
doi: 10.3390/md10122766.

Phlorotannin extracts from fucales characterized by HPLC-DAD-ESI-MSn: approaches to hyaluronidase inhibitory capacity and antioxidant properties

Federico Ferreres  1 , Graciliana Lopes, Angel Gil-Izquierdo, Paula B Andrade, Carla Sousa, Teresa Mouga, Patrícia Valentão
Affiliations
Comparative Study

Phlorotannin extracts from fucales characterized by HPLC-DAD-ESI-MSn: approaches to hyaluronidase inhibitory capacity and antioxidant properties

Federico Ferreres et al. Mar Drugs. .

Abstract

Purified phlorotannin extracts from four brown seaweeds (Cystoseira nodicaulis (Withering) M. Roberts, Cystoseira tamariscifolia (Hudson) Papenfuss, Cystoseira usneoides (Linnaeus) M. Roberts and Fucus spiralis Linnaeus), were characterized by HPLC-DAD-ESI-MSn. Fucophloroethol, fucodiphloroethol, fucotriphloroethol, 7-phloroeckol, phlorofucofuroeckol and bieckol/dieckol were identified. The antioxidant activity and the hyaluronidase (HAase) inhibitory capacity exhibited by the extracts were also assessed. A correlation between the extracts activity and their chemical composition was established. F. spiralis, the species presenting higher molecular weight phlorotannins, generally displayed the strongest lipid peroxidation inhibitory activity (IC₅₀ = 2.32 mg/mL dry weight) and the strongest HAase inhibitory capacity (IC₅₀ = 0.73 mg/mL dry weight). As for superoxide radical scavenging, C. nodicaulis was the most efficient species (IC₅₀ = 0.93 mg/mL dry weight), followed by F. spiralis (IC₅₀ = 1.30 mg/mL dry weight). These results show that purified phlorotannin extracts have potent capabilities for preventing and slowing down the skin aging process, which is mainly associated with free radical damage and with the reduction of hyaluronic acid concentration, characteristic of the process.

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Figures

Figure 1
Figure 1
Extracted Ion Chromatogram (EIC) of purified phlorotannin extracts of F. spiralis, C. usneoides, C. tamariscifolia and C. nodicaulis. [M + H]+ (m/z): 1, 499; 2, 747; 3–5, 871; 6–8, 995; 9 and 11, 375; 10, 499; 12, 623; 13, 499; 14, 497; 15–17, 499; 18–19, 497; 20–21, 603; 22, 743.
Figure 2
Figure 2
UV chromatograms of the purified phlorotannin extracts of F. spiralis, C. usneoides, C. tamariscifolia and C. nodicaulis, recorded at 280 nm. Identity of compounds as in Figure 1.
Figure 3
Figure 3
Hypothetical structure of the identified phlorotannins: Identity of compounds as in Figure 1.
Figure 4
Figure 4
+MS2[M + H]+ analysis of (A) compound 9 from C. usneoides and (B) compound 6 from F. spiralis.
Figure 5
Figure 5
Activity of purified phlorotannin extracts against superoxide radical (A) and lipid peroxidation (B). Results are expressed as percentage relative to control (mean ± standard deviation of three independent assays).
Figure 6
Figure 6
Inhibitory activity of purified phlorotannin extracts against hyaluronidase. Results are expressed as percentage of hyaluronidase inhibition relative to control (mean ± standard deviation of three independent assays).
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