Bifunctionalized Amphilectane Diterpenes from the Sponge Stylissa cf. massa

被引:18
作者
Chanthathamrongsiri, Naphatson [1 ]
Yuenyongsawad, Supreeya [1 ]
Wattanapiromsakul, Chatchai [1 ]
Plubrukarn, Anuchit [1 ]
机构
[1] Prince Songkla Univ, Marine Nat Prod Res Unit, Dept Pharmacognosy & Pharmaceut Bot, Fac Pharmaceut Sci, Hat Yai 90112, Songkhla, Thailand
来源
JOURNAL OF NATURAL PRODUCTS | 2012年 / 75卷 / 04期
关键词
MARINE SPONGE; ANTIMALARIAL ACTIVITY; ADVANCED PRECURSORS; CYMBASTELA-HOOPERI; ISOTHIOCYANATE AMPHILECTENES; CYCLIC HEPTAPEPTIDES; CRIBOCHALINA SP; BIOSYNTHESIS; ISONITRILES; CARIBICA;
D O I
10.1021/np200959j
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Two new amphilectane-type diterpenes, 8-isocyanato-15-formamidoamphilect-11(20)-ene (1) and 8-isothiocyanato-15-formamidoamphilect-11(20)-ene (2), along with two known derivatives, 8-isocyano-15-formarnidoamphilect-11(20)-ene (3) and 7-formamidoamphilect-11(20),15-diene (4), were isolated from the sponge Stylissa cf. massa. Diterpenes bearing two different isonitrile-related functionalities, as in 1-3, are rare. The coexistence of these compounds, all of which possess the identical carbon skeleton, in the same sponge specimen suggests interconversion among them. All the isolated compounds were tested for antimalarial activity. Compound 3 proved approximately 10 times more active than 1 and 2, indicating the importance of the isonitrile moiety to antimalarial activity versus the isocyanate and isothiocyanate groups, respectively. Compound 4, which contains only the formamide group, was inactive at the highest concentration tested.
引用
收藏
页码:789 / 792
页数:4
相关论文
共 25 条
[1]   ANTIMALARIAL ACTIVITY OF SESQUITERPENES FROM THE MARINE SPONGE ACANTHELLA-KLETHRA [J].
ANGERHOFER, CK ;
PEZZUTO, JM ;
KONIG, GM ;
WRIGHT, AD ;
STICHER, O .
JOURNAL OF NATURAL PRODUCTS, 1992, 55 (12) :1787-1789
[2]   New antifeedant bromopyrrole alkaloid from the Caribbean sponge Stylissa caribica [J].
Assmann, M ;
van Soest, RWM ;
Köck, M .
JOURNAL OF NATURAL PRODUCTS, 2001, 64 (10) :1345-1347
[3]   Advanced precursors in marine biosynthetic study.: Part 3:: The biosynthesis of dichloroimines in the tropical marine sponge Stylotella aurantium [J].
Brust, A ;
Garson, MJ .
TETRAHEDRON LETTERS, 2003, 44 (02) :327-330
[4]   Structural and stereochemical revision of isocyanide and isothiocyanate amphilectenes from the Caribbean marine sponge Cribochalina sp. [J].
Ciavatta, ML ;
Gavagnin, M ;
Manzo, E ;
Puliti, R ;
Mattia, CA ;
Mazzarella, L ;
Cimino, G ;
Simpson, JS ;
Garson, MJ .
TETRAHEDRON, 2005, 61 (33) :8049-8053
[5]   Structures and absolute stereochemistry of isocyanide and isothiocyanate amphilectenes from the Caribbean sponge Cribochalina sp. [J].
Ciavatta, ML ;
Fontana, A ;
Puliti, R ;
Scognamiglio, G ;
Cimino, G .
TETRAHEDRON, 1999, 55 (43) :12629-12636
[6]   Stylissamides E and F, Cyclic Heptapeptides from the Caribbean Sponge Stylissa caribica [J].
Cychon, Christine ;
Koeck, Matthias .
JOURNAL OF NATURAL PRODUCTS, 2010, 73 (04) :738-742
[7]   QUANTITATIVE ASSESSMENT OF ANTI-MALARIAL ACTIVITY INVITRO BY A SEMIAUTOMATED MICRODILUTION TECHNIQUE [J].
DESJARDINS, RE ;
CANFIELD, CJ ;
HAYNES, JD ;
CHULAY, JD .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1979, 16 (06) :710-718
[9]   Oxocyclostylidol, an intramolecular cyclized oroidin derivative from the marine sponge Stylissa caribica [J].
Grube, Achim ;
Koeck, Matthias .
JOURNAL OF NATURAL PRODUCTS, 2006, 69 (08) :1212-1214
[10]   Novel potent antimalarial diterpene isocyanates, isothiocyanates, and isonitriles from the tropical marine sponge Cymbastela hooperi [J].
Konig, GM ;
Wright, AD ;
Angerhofer, CK .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3259-3267