Antifouling Activity of Simple Synthetic Diterpenoids against Larvae of the Barnacle Balanus albicostatus Pilsbry

被引：11

作者：

Chen, Jun-De ^{[1
,2
]}

Yi, Rui-Zao ^{[2
]}

Sun, Cui-Ling ^{[3
]}

Feng, Dan-Qing ^{[4
]}

Lin, Yi-Ming ^{[1
]}

机构：

[1] Xiamen Univ, Sch Life Sci, Dept Biol, Xiamen 361005, Peoples R China

[2] State Ocean Adm, Inst Oceanog 3, Res Ctr Chem & Chem Engn Marine Biol Resource, Xiamen 361005, Peoples R China

[3] Xiamen Univ, Inst Biomed Res, Dept Nat Prod Chem, Xiamen 361005, Peoples R China

[4] Xiamen Univ, Dept Oceanog, Coll Oceanog & Environm Sci, Xiamen 361005, Peoples R China

来源：

MOLECULES | 2010年 / 15卷 / 11期

关键词：

pimarane diterpenoid; synthesis; antifouling activity; structure-activity relationship; MARINE SPONGE; METABOLITES; ENVIRONMENT;

D O I：

10.3390/molecules15118072

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Five new pimarane diterpenoids 1-5 were synthesized using ent-8(14)-pimarene-15R,16-diol as starting material. The structures were elucidated by means of extensive NMR and MS analysis. The antifouling activity against larval settlement of the barnacle Balanus albicostatus were evaluated using capsaicin as a positive control. Compounds 1-3 and 5 showed more potent antifouling activity than capsaicin. Compound 5, which exhibited almost the same antifouling activity as starting material, showed better stability than starting material. These compounds all showed antifouling activity in a non-toxic way against larval settlement of the barnacle B. albicostatus. Analysis of structure-activity relationships (SAR) demonstrated that the substituents on the C-15 and C-16 position of pimarane diterpenoid were responsible for the antifouling activity.

引用

页码：8072 / 8081

页数：10

共 23 条

[1]

[Anonymous], EUR J ORG CHEM

[2]

[Anonymous], J ORG CHEM

[3] Esterolytic peptide dendrimers with a hydrophobic core and catalytic residues at the surface [J].

Clouet, A ;

Darbre, T ;

Reymond, JL .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1195-1204

[4] Antifouling metabolites from the mangrove plant Ceriops tagal [J].

De Chen, Jun ;

Feng, Dan Qin ;

Yang, Zhi Wei ;

Wang, Zhan Chang ;

Qiu, Yan ;

Lin, Yi Ming .

MOLECULES, 2008, 13 (02) :212-219

[5] NEW DANGEROUS CHEMICALS IN THE ENVIRONMENT - LESSONS FROM TBT [J].

ELLIS, DV .

MARINE POLLUTION BULLETIN, 1991, 22 (01) :8-10

[6] Pyrethroids as Promising Marine Antifoulants: Laboratory and Field Studies [J].

Feng, Danqing ;

Ke, Caihuan ;

Li, Shaojing ;

Lu, Changyi ;

Guo, Feng .

MARINE BIOTECHNOLOGY, 2009, 11 (02) :153-160

[7]

Fischer K. J., 1993, US Patent, Patent No. 5226380

[8]

Fusetani N, 1996, J NAT TOXINS, V5, P249

[9] TRIMMED SPEARMAN-KARBER METHOD FOR ESTIMATING MEDIAN LETHAL CONCENTRATIONS IN TOXICITY BIOASSAYS [J].

HAMILTON, MA ;

RUSSO, RC ;

THURSTON, RV .

ENVIRONMENTAL SCIENCE & TECHNOLOGY, 1977, 11 (07) :714-719

[10] Inhibitory effects of Mediterranean sponge extracts and metabolites on larval settlement of the barnacle Balanus amphitrite [J].

Hellio, C ;

Tsoukatou, M ;

Maréchal, JP ;

Aldred, N ;

Beaupoil, C ;

Clare, AS ;

Vagias, C ;

Roussis, V .

MARINE BIOTECHNOLOGY, 2005, 7 (04) :297-305

← 1 2 3 →