Antioxidant Properties of the Manzamenones from the Tropical Marine Sponge Plakortis sp.

A new manzamenone derivative (4) and four known manzamenones were isolated from the tropical marine sponge Plakortis sp. These compounds exhibited an improved inhibitory effect against the copper-induced low-density lipoprotein oxidation. To identify their structural properties for antioxidant effects, 43-O-methylmanzamenone A (2) has been exposed oxidative conditions such as hydrogen peroxide, mCPBA and primary alkyl amines to give various derivatives (6)-(9). The structures of the compounds were determined by spectroscopic analyses and comparison with literature values.

[1]  Hyi-Seung Lee,et al.  Cytotoxic psammaplysin analogues from a Suberea sp. marine sponge and the role of the spirooxepinisoxazoline in their activity. , 2013, Journal of natural products.

[2]  J. Kobayashi,et al.  Manzamenone O, new trimeric fatty acid derivative from a marine sponge Plakortis sp. , 2013, Organic letters.

[3]  J. Kobayashi,et al.  Manzamenones L-N, new dimeric fatty-acid derivatives from an Okinawan marine sponge Plakortis sp. , 2013, Bioorganic & medicinal chemistry letters.

[4]  G. Hwang,et al.  Total synthsis of (+)-ambuic acid: α-bromination with 1,2-dibromotetrachloroethane. , 2012, The Journal of organic chemistry.

[5]  J. Kobayashi,et al.  Untenolide A, a new polyketide from an Okinawan marine sponge Plakortis sp. , 2010 .

[6]  R. Takeuchi,et al.  Synthetic analogues of the manzamenones and plakoridines which inhibit DNA polymerase. , 2006, Bioorganic & medicinal chemistry letters.

[7]  F. Reyes,et al.  New Bioactive Cyclic Peroxides from the Caribbean Marine Sponge Plakortis zyggompha. , 2006 .

[8]  F. Reyes,et al.  New bioactive cyclic peroxides from the Caribbean marine sponge Plakortis zyggompha , 2005 .

[9]  Yohei Tanaka,et al.  Chemical constituents of Morinda citrifolia fruits inhibit copper-induced low-density lipoprotein oxidation. , 2004, Journal of agricultural and food chemistry.

[10]  R. Whitehead,et al.  Predisposition in Synthesis: Efficient Routes to (.+-.)-Untenone A and (.+-.)-Manzamenones A, C, and F. , 2000 .

[11]  R. Whitehead,et al.  Predisposition in synthesis: Efficient routes to (±)-untenone A and (±)-manzamenones A, C and F , 2000 .

[12]  S. Takeuchi,et al.  Three new oxylipins related to 3,6-dioxo-4-docosenoic acid from Okinawan marine sponges, Plakortis spp , 1995 .

[13]  S. Takeuchi,et al.  Plakoridine A, a new tyramine-containing pyrrolidine alkaloid from the Okinawan marine sponge Plakortis sp. , 1994 .

[14]  S. Takeuchi,et al.  Untenone A, a new cyclopentenone from the Okinawan marine sponge Plakortis sp. corresponding to the dienophile in the biosynthesis of manzamenones , 1993 .

[15]  S. Takeuchi,et al.  Manzamenones A-F from the Okinawan marine sponges Plakortis Sp.: novel dimeric fatty acid derivatives possessing a bicyclo[4.3.0]nonane skeleton , 1992 .

[16]  D. Stierle,et al.  Metabolites of three marine sponges of the genus Plakortis , 1980 .