Production of octadienal in the marine diatom Skeletonema costatum

被引：62

作者：

d'Ippolito, G

Romano, G

Caruso, T

Spinella, A

Cimino, G

Fontana, A

机构：

[1] CNR, ICB, I-80078 Pozzuoli, Napoli, Italy

[2] Staz Zool Anton Dohrn, I-80121 Naples, Italy

[3] Univ Salerno, Dipartimento Chim, Fac Sci, I-84041 Baronissi, Salerno, Italy

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 06期

关键词：

D O I：

10.1021/ol034057c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Marine diatoms produce alpha,beta,gamma,delta-unsaturated aldehydes that have detrimental effects on the reproduction of their natural predators. The production of these defensive metabolites is suggested to involve enzymatic oxidation of. polyunsaturated fatty acids. In this paper, feeding experiments with labeled precursor provide clear evidence in support of the origin of octadienals 1 and 2 from 6,9,12-hexadecatrienoic acid (5), thus proving the involvement of novel lipoxygenase/lyase activity for the oxidation of C-16 fatty acids.

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页码：885 / 887

页数：3

相关论文

共 12 条

[1] REASSESSMENT OF LIPID-COMPOSITION OF THE DIATOM, SKELETONEMA-COSTATUM [J].

BERGE, JP ;

GOUYGOU, JP ;

DUBACQ, JP ;

DURAND, P .

PHYTOCHEMISTRY, 1995, 39 (05) :1017-1021

[2] First total synthesis of natural aplyolides C and E, ichthyotoxic macrolides isolated from the skin of the marine mollusc Aplysia depilans [J].

Caruso, T ;

Spinella, A .

TETRAHEDRON-ASYMMETRY, 2002, 13 (19) :2071-2073

[3] New birth-control aldehydes from the marine diatom Skeletonema costatum:: characterization and biogenesis [J].

d'Ippolito, G ;

Romano, G ;

Iadicicco, O ;

Miralto, A ;

Ianora, A ;

Cimino, G ;

Fontana, A .

TETRAHEDRON LETTERS, 2002, 43 (35) :6133-6136

[4] Detection of short-chain aldehydes in marine organisms:: the diatom Thalassiosira rotula [J].

d'Ippolito, G ;

Iadicicco, I ;

Romano, G ;

Fontana, A .

TETRAHEDRON LETTERS, 2002, 43 (35) :6137-6140

[5] Copepod hatching success in marine ecosystems with high diatom concentrations [J].

Irigoien, X ;

Harris, RP ;

Verheye, HM ;

Joly, P ;

Runge, J ;

Starr, M ;

Pond, D ;

Campbell, R ;

Shreeve, R ;

Ward, P ;

Smith, AN ;

Dam, HG ;

Peterson, W ;

Tirelli, V ;

Koski, M ;

Smith, T ;

Harbour, D ;

Davidson, R .

NATURE, 2002, 419 (6905) :387-389

[6] The insidious effect of diatoms on copepod reproduction [J].

Miralto, A ;

Barone, G ;

Romano, G ;

Poulet, SA ;

Ianora, A ;

Russo, GL ;

Buttino, I ;

Mazzarella, G ;

Laabir, M ;

Cabrini, M ;

Giacobbe, MG .

NATURE, 1999, 402 (6758) :173-176

[7] Are volatile unsaturated aldehydes from diatoms the main line of chemical defence against copepods? [J].

Pohnert, G ;

Lumineau, O ;

Cueff, A ;

Adolph, S ;

Cordevant, C ;

Lange, M ;

Poulet, S .

MARINE ECOLOGY PROGRESS SERIES, 2002, 245 :33-45

[8] Phospholipase A2 activity triggers the wound-activated chemical defense in the diatom Thalassiosira rotula [J].

Pohnert, G .

PLANT PHYSIOLOGY, 2002, 129 (01) :103-111

[9] First total synthesis of natural aplyolides B and D, ichthyotoxic macrolides isolated from the skin of the marine mollusk Aplysia depilans [J].

Spinella, A ;

Caruso, T ;

Coluccini, C .

TETRAHEDRON LETTERS, 2002, 43 (09) :1681-1683

[10]

Spinella A, 2001, SYNLETT, P1971