Phoriospongin A and B:: Two new nematocidal depsipeptides from the Australian marine sponges Phoriospongia sp and Callyspongia bilamellata

被引:37
作者
Capon, RJ [1 ]
Ford, J
Lacey, E
Gill, JH
Heiland, K
Friedel, T
机构
[1] Univ Melbourne, Sch Chem, Parkville, Vic 3010, Australia
[2] Microbial Screening Technol Pty Ltd, Kemps Creek, NSW 2171, Australia
[3] Novartis Anim Hlth Australia Pty Ltd, Kemps Creek, NSW 2171, Australia
来源
JOURNAL OF NATURAL PRODUCTS | 2002年 / 65卷 / 03期
关键词
D O I
10.1021/np010329d
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Bioassay-directed fractionation of two southern Australian sponges, Phoriospongia sp. and Callyspongia bilamellata, yielded two new nematocidal depsipeptides, identified as phoriospongins A (1) and B (2). The structures of the phoriospongins were determined by detailed spectroscopic analysis and comparison with the previously reported sponge depsipeptide cyclolithistide A (3), as well as ESIMS and HPLC analysis of acid hydrolysates. It is noteworthy that the unique and yet structurally related metabolites 1-3 are found in sponges spanning three taxonomic orders, Poescilosclerida, Haplosclerida, and Lithistida.
引用
收藏
页码:358 / 363
页数:6
相关论文
共 21 条
[1]   ASYMMETRIC-SYNTHESIS OF N-METHYL-ALPHA-AMINO ESTERS FROM A GLYOXAL DERIVED CHIRAL HETEROCYCLE [J].
AGAMI, C ;
COUTY, F ;
PRINCE, B ;
PUCHOT, C .
TETRAHEDRON, 1991, 47 (25) :4343-4354
[2]   EPOXY LIPIDS FROM THE AUSTRALIAN EPIPHYTIC BROWN ALGA NOTHEIA-ANOMALA [J].
BARROW, RA ;
CAPON, RJ .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1990, 43 (05) :895-911
[3]   Two classes of metabolites from Theonella swinhoei are localized in distinct populations of bacterial symbionts [J].
Bewley, CA ;
Holland, ND ;
Faulkner, DJ .
EXPERIENTIA, 1996, 52 (07) :716-722
[4]   Geodin A magnesium salt:: A novel nematocide from a southern Australian marine sponge, Geodia [J].
Capon, RJ ;
Skene, C ;
Lacey, E ;
Gill, JH ;
Wadsworth, D ;
Friedel, T .
JOURNAL OF NATURAL PRODUCTS, 1999, 62 (09) :1256-1259
[5]   The isolation and synthesis of novel nematocidal dithiocyanates from an Australian marine sponge, Oceanapia sp. [J].
Capon, RJ ;
Skene, C ;
Liu, EHT ;
Lacey, E ;
Gill, JH ;
Heiland, K ;
Friedel, T .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) :7765-7769
[6]   Marine nematocides:: Tetrahydrofurans from a southern Australian brown alga, Notheia anomala. [J].
Capon, RJ ;
Barrow, RA ;
Rochfort, S ;
Jobling, M ;
Skene, C ;
Lacey, E ;
Gill, JH ;
Friedel, T ;
Wadsworth, D .
TETRAHEDRON, 1998, 54 (10) :2227-2242
[7]   New chiral didehydroamino acid derivatives from a cyclic glycine template with 3,6-dihydro-2H-1,4-oxazin-2-one structure:: Applications to the asymmetric synthesis of nonproteinogenic α-amino acids [J].
Chinchilla, R ;
Falvello, LR ;
Galindo, N ;
Nájera, C .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) :3034-3041
[8]   An antifungal cyclodepsipeptide, cyclolithistide A, from the sponge Theonella swinhoei [J].
Clark, DP ;
Carroll, J ;
Naylor, S ;
Crews, P .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (24) :8757-8764
[9]   BIOACTIVE SPONGE PEPTIDES [J].
FUSETANI, N ;
MATSUNAGA, S .
CHEMICAL REVIEWS, 1993, 93 (05) :1793-1806
[10]   AVERMECTIN INHIBITION OF LARVAL DEVELOPMENT IN HAEMONCHUS-CONTORTUS - EFFECTS OF IVERMECTIN RESISTANCE [J].
GILL, JH ;
REDWIN, JM ;
VANWYK, JA ;
LACEY, E .
INTERNATIONAL JOURNAL FOR PARASITOLOGY, 1995, 25 (04) :463-470