Marine natural products as novel antioxidant prototypes
Marine natural products as novel antioxidant prototypes
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DOI：
10.1021/np0204038
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发表时间：
2003-05-01
影响因子：
5.1
通讯作者：
Nagle, DG
中科院分区：
文献类型：
--
作者：
Takamatsu, S;Hodges, TW;Nagle, DG
使用基于 2,2-二苯基-1-三硝基苯肼自由基 (DPPH) 溶液的化学测定和基于 2',7'-二氯二氢荧光素二乙酸酯 (DCFH-DA) 细胞的测定，检查从海绵、藻类和蓝藻中分离的纯天然产品的抗氧化活性。 DCFH 系统仅检测穿透细胞膜的抗氧化剂。确定了有效的抗氧化剂，并对每个系统的结果进行了比较。藻类代谢物 cymopol (1)、avrainvilleol (3) 和 fragilamide (4) 以及无脊椎动物成分 puupehenone (5) 在两个系统中均表现出很强的抗氧化活性。几种化合物在 DPPH 测定中具有活性，但在 DCFH 系统中活性明显较低。从Cymopolia barbata 中分离出绿藻代谢物7-羟基cymopol (2) 并确定了其结构。化合物 2 在 DCFH 系统中的活性明显低于 cymopol (1)。海绵代谢物 (1S)-(+)-姜黄酚 (6)、aaptamine (7)、isoaaptamine (8) 和 curcudiol (9) 以及蓝藻色素 scytonemin (10) 在 DPPH 测定中表现出很强的抗氧化活性，但在 DCFH 系统中相对不活跃。因此，细胞摄取极大地影响仅使用 DPPH 测定发现的抗氧化剂的潜在意义。明显的“促抗氧化剂”激素胺 A 二乙酸酯 (11) 和劳伦西亚单体二乙酸酯 (12) 需要代谢激活才能发挥抗氧化活性。使用基于溶液和基于细胞的测定来发现新的抗氧化剂具有显着的优势。
Pure natural products isolated from marine sponges, algae, and cyanobacteria were examined for antioxidant activity using a 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) solution-based chemical assay and a 2',7'-dichlorodihydrofluorescein diacetate (DCFH-DA) cellular-based assay. The DCFH system detects only antioxidants that penetrate cellular membranes. Potent antioxidants were identified and the results from each system compared. The algal metabolites cymopol (1), avrainvilleol (3), and fragilamide (4), and the invertebrate constituent puupehenone (5) showed strong antioxidant activity in both systems. Several compounds were active in the DPPH assay but significantly less active in the DCFH system. The green algal metabolite 7-hydroxycymopol (2) was isolated from Cymopolia barbata and its structure determined. Compound 2 was significantly less active in the DCFH system than cymopol (1). The sponge metabolites (1S)-(+)-curcuphenol (6), aaptamine (7), isoaaptamine (8), and curcudiol (9) and the cyanobacterial pigment scytonemin (10) showed strong antioxidant activity in the DPPH assay, but were relatively inactive in the DCFH system. Thus, cellular uptake dramatically affects the potential significance of antioxidants discovered using only the DPPH assay. The apparent "proantioxidants" hormothamnione A diacetate (11) and Laurencia monomer diacetate (12) require metabolic activation for antioxidant activity. Significant advantages are achieved using both a solution- and cellular-based assay to discover new antioxidants.