Puupehenol, a Potent Antioxidant Antimicrobial Meroterpenoid from a Hawaiian Deep-Water Dactylospongia sp Sponge

被引:35
作者
Hagiwara, Kehau [1 ]
Hernandez, Jaaziel E. Garcia [1 ]
Harper, Mary Kay [2 ]
Carroll, Anthony [3 ]
Motti, Cherie A. [4 ]
Awaya, Jonathan [5 ]
Hoang-Yen Nguyen [5 ]
Wright, Anthony D. [1 ]
机构
[1] Univ Hawaii, DKI Coll Pharm, Hilo, HI 96720 USA
[2] Univ Utah, Dept Med Chem, Salt Lake City, UT 84112 USA
[3] Griffith Univ, Sch Environm, Brisbane, Qld 4222, Australia
[4] Australian Inst Marine Sci, Townsville, Qld 4810, Australia
[5] Univ Hawaii, Dept Biol, Hilo, HI 96720 USA
来源
JOURNAL OF NATURAL PRODUCTS | 2015年 / 78卷 / 02期
关键词
SESQUITERPENOID QUINONE; ABSOLUTE-CONFIGURATIONS; MARINE; STEREOCHEMISTRY; METABOLITES; POWER; ACID;
D O I
10.1021/np500793g
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
From the organic extract of a deep-water Hawaiian sponge Dactylospongia sp., a new potent antioxidant and antimicrobial meroterpenoid, puupehenol (1), was isolated. The structure of 1 was determined using spectroscopic techniques (H-1 and C-13 NMR, MS, IR, UV, [alpha](D)). The known compound puupehenone (2) was also isolated and suggested as a probable artifact of the isolation procedures. Complete unambiguous H-1 and C-13 NMR data are provided for compounds 1 and 2. Bioassays performed with 1 and 2 showed them both to be very effective antioxidants and to have antimicrobial properties.
引用
收藏
页码:325 / 329
页数:5
相关论文
共 24 条
[1]  
Benzie IFF, 1999, METHOD ENZYMOL, V299, P15
[2]   The ferric reducing ability of plasma (FRAP) as a measure of ''antioxidant power'': The FRAP assay [J].
Benzie, IFF ;
Strain, JJ .
ANALYTICAL BIOCHEMISTRY, 1996, 239 (01) :70-76
[3]   A REVISION OF THE ABSOLUTE STEREOCHEMISTRY OF ILIMAQUINONE [J].
CAPON, RJ ;
MACLEOD, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) :5059-5060
[4]   Natural product extracts of plant and marine origin having antileukemia potential. The NCI experience [J].
Cragg, GM ;
Newman, DJ ;
Yang, SS .
JOURNAL OF NATURAL PRODUCTS, 2006, 69 (03) :488-498
[5]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[6]   Pelorol from the tropical marine sponge Dactylospongia elegans [J].
Goclik, E ;
König, GM ;
Wright, AD ;
Kaminsky, R .
JOURNAL OF NATURAL PRODUCTS, 2000, 63 (08) :1150-1152
[7]   GENERAL-METHOD FOR DETERMINING ABSOLUTE-CONFIGURATIONS OF ACYCLIC ALLYLIC ALCOHOLS [J].
GONNELLA, NC ;
NAKANISHI, K ;
MARTIN, VS ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (13) :3775-3776
[8]   The Importance of 1H-Nuclear Magnetic Resonance Spectroscopy for Reference Standard Validation in Analytical Sciences [J].
Kelman, Dovi ;
Wright, Anthony D. .
PLOS ONE, 2012, 7 (07)
[9]   Spongian diterpenoids from marine sponges [J].
Keyzers, RA ;
Northcote, PT ;
Davies-Coleman, MT .
NATURAL PRODUCT REPORTS, 2006, 23 (02) :321-334
[10]   METABOLITES OF THE PALAUAN SPONGE DACTYLOSPONGIA SP [J].
KUSHLAN, DM ;
FAULKNER, DJ ;
PARKANYI, L ;
CLARDY, J .
TETRAHEDRON, 1989, 45 (11) :3307-3312