New γ-pyrone propionates from the Indian Ocean sacoglossan Placobranchus ocellatus

被引:42
作者
Manzo, E
Ciavatta, ML
Gavagnin, M
Mollo, E
Wahidulla, S
Cimino, G
机构
[1] CNR, Ist Chim Biol, I-80078 Puzzuoli, NA, Italy
[2] CSIR, Natl Inst Oceanog, Panaji, Goa, India
关键词
gamma-pyrone propionates; sacoglossan; Placobranchus ocellatus; bicyclo octane;
D O I
10.1016/j.tetlet.2004.11.085
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new gamma-pyrone propionate, compound 9, and its peroxy derivative 10 have been isolated from the sacoglossan Placobranchus ocellatus. The structure and the relative stereochemistry of the new molecules. which displayed an unprecedented carbon skeleton characterised by a bicyclo [4.2.0] octane. have been determined by both spectroscopic method, and comparison with model Compounds. By analogy with photodeoxytridachione (2), a sunscreen protective role could be also suggested for compound 9 in living P. ocellatus. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:465 / 468
页数:4
相关论文
共 9 条
[1]  
Cimino G, 1999, CURR ORG CHEM, V3, P327
[2]   New polypropionate pyrones from the Philippine sacoglossan mollusc Placobranchus ocellatus [J].
Fu, X ;
Hong, EP ;
Schmitz, FJ .
TETRAHEDRON, 2000, 56 (46) :8989-8993
[3]   SECONDARY METABOLITES FROM MEDITERRANEAN ELYSIOIDEA - ORIGIN AND BIOLOGICAL ROLE [J].
GAVAGNIN, M ;
MARIN, A ;
MOLLO, E ;
CRISPINO, A ;
VILLANI, G ;
CIMINO, G .
COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY B-BIOCHEMISTRY & MOLECULAR BIOLOGY, 1994, 108 (01) :107-115
[4]   Chemical studies of Caribbean sacoglossans: Dietary relationships with green algae and ecological implications [J].
Gavagnin, M ;
Mollo, E ;
Montanaro, D ;
Ortea, J ;
Cimino, G .
JOURNAL OF CHEMICAL ECOLOGY, 2000, 26 (07) :1563-1578
[5]   A new gamma-dihydropyrone-propionate from the Caribbean sacoglossan Tridachia crispata. [J].
Gavagnin, M ;
Mollo, E ;
Cimino, G ;
Ortea, J .
TETRAHEDRON LETTERS, 1996, 37 (24) :4259-4262
[6]   POLYPROPIONATES FROM THE MEDITERRANEAN MOLLUSK ELYSIA-TIMIDA [J].
GAVAGNIN, M ;
SPINELLA, A ;
CASTELLUCCIO, F ;
CIMINO, G ;
MARIN, A .
JOURNAL OF NATURAL PRODUCTS, 1994, 57 (02) :298-304
[7]   THE METABOLITES OF THE MARINE MOLLUSKS TRIDACHIELLA-DIOMEDEA AND TRIDACHIA-CRISPATA [J].
IRELAND, C ;
FAULKNER, J .
TETRAHEDRON, 1981, 37 :233-240
[8]   PHOTOSYNTHETIC MARINE MOLLUSKS - INVIVO C-14 INCORPORATION INTO METABOLITES OF THE SACOGLOSSAN PLACOBRANCHUS-OCELLATUS [J].
IRELAND, C ;
SCHEUER, PJ .
SCIENCE, 1979, 205 (4409) :922-923
[9]  
IRELAND C, 1978, J AM CHEM SOC, P1002