Dihydroisocoumarin derivatives with antifouling activities from a gorgonian-derived Eurotium sp. fungus

被引：40

作者：

Chen, Min ^{[1
]}

Shao, Chang-Lun ^{[1
]}

Wang, Kai-Ling ^{[1
,3
]}

Xu, Ying ^{[2
,3
]}

She, Zhi-Gang ^{[4
]}

Wang, Chang-Yun ^{[1
]}

机构：

[1] Ocean Univ China, Sch Med & Pharm, Minist Educ China, Key Lab Marine Drugs, Qingdao 266003, Peoples R China

[2] Shenzhen Univ, Coll Life Sci, Shenzhen 518060, Peoples R China

[3] Hong Kong Univ Sci & Technol, Div Life Sci, Hong Kong, Hong Kong, Peoples R China

[4] Sun Yat Sen Univ, Sch Chem & Chem Engn, Guangzhou 510275, Guangdong, Peoples R China

来源：

TETRAHEDRON | 2014年 / 70卷 / 47期

基金：

中国国家自然科学基金;

关键词：

Gorgonian-derived fungus; Eurotium sp; Dihydroisocoumarin derivatives; Enantiomeric separation; Antifouling activity; STRUCTURE ELUCIDATION; METABOLITES; PRODUCTS; LACTONES;

D O I：

10.1016/j.tet.2014.08.055

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Five pairs of new dihydroisocoumarin enantiomers, (+/-)-eurotiumitles A-E, and two related racemates, (+/-)-eurotiumides F and G, were isolated from a gorgonian-derived fungus, Eurotium sp. XS-200900E6. The enantiomeric separations for (+/-)-eurotiumides A E were achieved by chiral-HPLC, and their absolute configurations were determined by ECD spectra. All of the isolated compounds are rare dihydroisocoumarin derivatives with a methoxy at C-4. (+)- And (-)-eurotiumides B and D with cis configurations of H-3/H-4 exhibited potent antifouling activities against the larval settlement of the barnacle Balanus amphitrite with the EC50 values ranging from 0.7 to 2.3 mu g/mL, and displayed high therapeutic ratios (LC50/EC50 >15). The tested compounds also showed extensive antibacterial activities. It was the first report of antifouling activities for dihydroisocoumarin derivatives. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：9132 / 9138

页数：7

共 24 条

[1] Aurocitrin and related polyketide metabolites from the wood-decay fungus Hypocrea sp BCC 14122 [J].

Berkaew, Pitchapa ;

Soonthornchareonnon, Noppamas ;

Salasawadee, Kitlada ;

Chanthaket, Rungtiwa ;

Isaka, Masahiko .

JOURNAL OF NATURAL PRODUCTS, 2008, 71 (05) :902-904

[2] Bioactive Indole Alkaloids and Phenyl Ether Derivatives from a Marine-Derived Aspergillus sp Fungus [J].

Chen, Min ;

Shao, Chang-Lun ;

Fu, Xiu-Mei ;

Xu, Ru-Fang ;

Zheng, Juan-Juan ;

Zhao, Dong-Lin ;

She, Zhi-Gang ;

Wang, Chang-Yun .

JOURNAL OF NATURAL PRODUCTS, 2013, 76 (04) :547-553

[3] LC-MS Guided Isolation of (±)-Sweriledugenin A, a Pair of Enantiomeric Lactones, from Swertia leducii [J].

Geng, Chang-An ;

Chen, Xing-Long ;

Zhou, Ning-Jia ;

Chen, Hao ;

Ma, Yun-Bao ;

Huang, Xiao-Yan ;

Zhang, Xue-Mei ;

Chen, Ji-Jun .

ORGANIC LETTERS, 2014, 16 (02) :370-373

[4] Dihydroisocoumarin from Xyris pterygoblephara active against dermatophyte fungi [J].

Guimaraes, Keller Guilherme ;

Filho, Jose Dias de Souza ;

Dos Mares-Guia, Thiago Renno ;

Braga, Fernao Castro .

PHYTOCHEMISTRY, 2008, 69 (02) :439-444

[5] Oxidative rearrangements of isobenzofurans: Studies toward the synthesis of the ajudazols [J].

Hobson, Stephen J. ;

Parkin, Andrew ;

Marquez, Rodolfo .

ORGANIC LETTERS, 2008, 10 (13) :2813-2816

[6] ALKOXIDE-INDUCED RING-OPENING OF METHOXYMETHYLIDENE-SUBSTITUTED HOMOPHTHALIC ANHYDRIDE .2. STRUCTURE AND CONFORMATIONAL-ANALYSIS OF THE DIHYDROISOCOUMARIN PRODUCTS [J].

HUTCHINGS, MG ;

CHIPPENDALE, AM ;

SHUKLA, R ;

MCPARTLIN, M .

TETRAHEDRON, 1991, 47 (37) :7869-7874

[7]

Jansen R, 2002, EUR J ORG CHEM, V2002, P917

[8] Antimalarial dihydroisocoumarins produced by Geotrichum sp., an endophytic fungus of Crassocephalum crepidioides [J].

Kongsaeree, P ;

Prabpai, S ;

Sriubolmas, N ;

Vongvein, C ;

Wiyakrutta, S .

JOURNAL OF NATURAL PRODUCTS, 2003, 66 (05) :709-711

[9] Dihydroisocoumarins from fungi: Isolation, structure elucidation, circular dichroism and biological activity [J].

Krohn, K ;

Bahramsari, R ;

Florke, U ;

Ludewig, K ;

KlicheSpory, C ;

Michel, A ;

Aust, HJ ;

Draeger, S ;

Schulz, B ;

Antus, S .

PHYTOCHEMISTRY, 1997, 45 (02) :313-320

[10] Cembranoids from the Soft Coral Sinularia rigida with Antifouling Activities [J].

Lai, Daowan ;

Geng, Zhufeng ;

Deng, Zhiwei ;

van Ofwegen, Leen ;

Proksch, Peter ;

Lin, Wenhan .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2013, 61 (19) :4585-4592

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