Antioxidant and Antiviral Activities of Plastoquinones from the Brown Alga &lt;i&gt;Sargassum micracanthum&lt;/i&gt;, and a New Chromene Derivative Converted from the Plastoquinones

Iwashima, Makoto; Mori, Jun; Xiang, Ting; Matsunaga, Takayuki; Hayashi, Kyoko; Shinoda, Daishi; Saito, Haruo; Sankawa, Ushio; Hayashi, Toshimitsu

doi:10.1248/bpb.28.374

Cited by 109 publications

(67 citation statements)

References 13 publications

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“…6) 1 and 3 exhibited antioxidant activity, while 2 and 3 exhibited antiviral effect on human cytomegalovirus. 6) Osteoporosis, a disease characterized by low bone mass and structural deterioration of bone tissue, has been widely recognized as one of major public health problems. In order to prevent or treat osteoporosis, it is quite important to find novel candidates of lead compound for the development of clinically useful drugs.…”

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confidence: 99%

Inhibitory Activities of Plastoquinones and Chromene Derivative from a Brown Alga Sagassum micracanthum on Bone Resorption

Komai

Miyahara

Mori

et al. 2006

Biological & Pharmaceutical Bulletin

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In recent years, many marine resources have attracted attention in the search for bioactive compounds to develop new drugs. We have taken note of brown algae of the genus Sargassum (Sargassacea, Fucales), which contain structurally unique secondary metabolites such as palstoquinones, 1,2) chromanol, 3,4) and chromenes. 5) In the course of studies on search for bioactive molecules of algae, we isolated plastoquinones [hydroquinone (1) and quinone (2)] together with a novel chromene derivative (3) from a brown alga, Sargassum micracanthum (KUETZING) ENDLICHER, "Togemoku" in Japanese (Fig. 1).6) 1 and 3 exhibited antioxidant activity, while 2 and 3 exhibited antiviral effect on human cytomegalovirus. 6)Osteoporosis, a disease characterized by low bone mass and structural deterioration of bone tissue, has been widely recognized as one of major public health problems. In order to prevent or treat osteoporosis, it is quite important to find novel candidates of lead compound for the development of clinically useful drugs. Thus, we evaluated the effects of 1, 2 and 3 on bone resorption. This paper describes their inhibitory effects on osteoclast-like cells (OCLs) formation, pit formation and survival of OCLs. MATERIALS AND METHODS Preparation of Osteoclast-Like CellsBone marrow cells were isolated from 7-week-old male ddY mice (Sankyo Lab. Service) as described previously.7) The bone marrow cells (1ϫ10 7 cells) were suspended in 10 ml of a-MEM supplemented with 10% FBS, and incubated for 24 h with 10 ng/ml macrophage-colony stimulating factor (M-CSF) (recombinant human, Wako Pure Chemical Industries, Ltd.). Nonadherent cells were used as osteoclast progenitor cells [M-CSF-dependent (MD) cells] in the OCL formation and survival experiments. MD cells (1ϫ10 5 cells/100 ml) were added to 96-well plates with 10 ng/ml M-CSF and 100 ng/ml sRANKL (recombinant human, Wako Ltd.) in the absence or presence of test compounds and cultured for 6 d. Adherent cells were then stained for tartrate-resistant acid phosphatase (TRAP) activity as previously described. 7) TRAP(ϩ) multinucleated cells having three or more nuclei were counted as OCLs. Ϫ6 M PGE 2 (Sigma) using collagen-precoated dishes. After culturing for 7 d, the dishes were treated with 0.2% bacterial collagenase, and the OCLs were collected and resuspended in a-MEMϩ10% FBS to be used to assay pit formation assay. Coculture of Mouse Bone Marrow Cells and Osteoblast-Like CellsDentin Resorption Assay The assay for dentine resorption by OCLs was performed as previously described. 9)Briefly, the dentine slices were placed into the wells of 96-well plate containing 0.1 ml a-MEM supplemented with 10% FBS. OCL preparation (1.3ϫ10 3 cells) suspended in 0.1 ml of the same medium was transferred onto the slices. After incubation for 90 min at 37°C, the slices were placed into the wells of 24-well plates containing a-MEMϩ10% Medicine and Pharmaceutical Sciences, University of Toyama; 2630 Sugitani, Toyama 930-0194, Japan: and b Department of Pharmaceutical Research, Lead Chemical Co....

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Inhibitory Activities of Plastoquinones and Chromene Derivative from a Brown Alga Sagassum micracanthum on Bone Resorption

Komai

Miyahara

Mori

et al. 2006

Biological & Pharmaceutical Bulletin

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“…[6][7][8][9][10] We have reported that the tyrosinase inhibitory activity of 1 was stronger than that of arbutin. Furthermore, 1 also showed potent antioxidant activity.…”

Section: Abstract: Daedalea Dickinsii; Chroman; Tyrosinase; Antioxidantmentioning

confidence: 98%

Daedalin A, a Metabolite ofDaedalea dickinsii, Inhibits Melanin Synthesis in anin VitroHuman Skin Model

Morimura

Hiramatsu

Yamazaki

et al. 2009

Bioscience, Biotechnology, and Biochemistry

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“…Extracts of S. micracanthum have been shown to exhibit antioxidant, anti-viral and selective vasodilation effects. 4,5,8 As part of our ongoing effort to find natural antioxidants, we have isolated a new free-radical scavenger, designated sargassumol (1, Figure 1), from the methanolic extract of S. micracanthum. In this paper, the isolation, structure determination and free radical scavenging activity of 1 are described.…”

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“…It comprises more than 400 species. These are known to produce diverse bioactive entities including plastoquinones, 4 chromanol, 5 cyclopentenone 6 and polysaccharides. 7 S. micracanthum is found in Japan and South Korea, mainly on the south and east coasts.…”

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Sargassumol, a novel antioxidant from the brown alga Sargassum micracanthum

et al. 2011

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Free radicals have been implicated in the pathogenesis of diseases such as ischemia, arteriosclerosis, diabetes, rheumatoid arthritis, inflammation and the initiation of cancer. [1][2][3] There is considerable evidence that antioxidants may help prevent illnesses caused by oxidative stress due to their capacity to quench free radicals, thereby protecting cells and tissues from oxidative damage. Thus, the demand for alternative antioxidants from natural sources is gradually growing.The genus Sargassum (Sargassaceae), which belongs to the large brown algae, is distributed mainly throughout temperate Pacific coastal regions, areas of the Indian Ocean and along the Australian coast. It comprises more than 400 species. These are known to produce diverse bioactive entities including plastoquinones, 4 chromanol, 5 cyclopentenone 6 and polysaccharides. 7 S. micracanthum is found in Japan and South Korea, mainly on the south and east coasts. Extracts of S. micracanthum have been shown to exhibit antioxidant, anti-viral and selective vasodilation effects. 4,5,8 As part of our ongoing effort to find natural antioxidants, we have isolated a new free-radical scavenger, designated sargassumol (1, Figure 1), from the methanolic extract of S. micracanthum. In this paper, the isolation, structure determination and free radical scavenging activity of 1 are described.Dried S. micracanthum (122 g) collected at Wando county, Jeonnam province, Korea was ground and extracted with methanol at room temperature. This methanolic extract was concentrated under reduced pressure and the aqueous resultant was consecutively partitioned with hexane, chloroform, ethyl acetate and n-butanol. The ethyl acetatesoluble portion, exhibiting potent radical scavenging activity, was concentrated under reduced pressure, subjected to Sephadex LH-20 column chromatography and eluted with 70% aqueous methanol. An antioxidant fraction was further separated by preparative reversedphase HPLC eluted with a gradient of methanol concentrations increasing to 40% in water acidified with 0.04% trifluoroacetic acid to afford compound 1 (2 mg). Table 1. In an 1 H-1 H COSY spectrum, the methine proton at d 4.82 (H-3) showed a cross-peak with the methine proton at d 4.17 (H-1), suggesting their allylic relationship (Figure 2). The structure of compound 1 was determined by HMBC spectrum, as shown in Figure 2. A long-range correlation of the methine proton at d 4.82 (H-3) to the oxygenated sp 2 quaternary carbon at d 173.7 (C-2) and the chemical shift value of the carbonyl carbon at d 197.1 (C-4) suggested the presence of an a,b-unsaturated ketone moiety. In addition, the methine proton at d 4.82 (H-3) revealed a long-range correlation to the oxygenated sp 3 quaternary carbon at d 79.9 (C-5), and the hydroxyl protons at d 5.66 and 5.53 revealed crucial HMBC correlations to the carbons at d 79.9 (C-5), 75.6 (C-9), and 48.5 (C-6) and 79.9 (C-5), 75.6 (C-9) and 52.5 (C-1), respectively, establishing a six-membered

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Antioxidant and Antiviral Activities of Plastoquinones from the Brown Alga <i>Sargassum micracanthum</i>, and a New Chromene Derivative Converted from the Plastoquinones

Cited by 109 publications

References 13 publications

Inhibitory Activities of Plastoquinones and Chromene Derivative from a Brown Alga Sagassum micracanthum on Bone Resorption

Inhibitory Activities of Plastoquinones and Chromene Derivative from a Brown Alga Sagassum micracanthum on Bone Resorption

Daedalin A, a Metabolite ofDaedalea dickinsii, Inhibits Melanin Synthesis in anin VitroHuman Skin Model

Sargassumol, a novel antioxidant from the brown alga Sargassum micracanthum

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