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Titolo:
Uracil moiety is required for toxicity of the cyanobacterial hepatotoxin cylindrospermopsin
Autore:
Banker, R; Carmeli, S; Werman, M; Teltsch, B; Porat, R; Sukenik, A;
Indirizzi:
Israel Oceanog & Limnol Res, Yigal Allon Kinneret Limnol Lab, IL-14102 Tiberias, Israel Israel Oceanog & Limnol Res Tiberias Israel IL-14102 02 Tiberias, Israel Tel Aviv Univ, Raymond & Beverly Sackler Fac Exact Sci, Sch Chem, IL-69978Tel Aviv, Israel Tel Aviv Univ Tel Aviv Israel IL-69978 ch Chem, IL-69978Tel Aviv, Israel Technion Israel Inst Technol, Dept Food Engn & Biotechnol, IL-32000 Haifa,Israel Technion Israel Inst Technol Haifa Israel IL-32000 IL-32000 Haifa,Israel Mekorot Natl Water Co, Cent Lab, Nazareth Illit, Israel Mekorot Natl WaterCo Nazareth Illit Israel Lab, Nazareth Illit, Israel
Titolo Testata:
JOURNAL OF TOXICOLOGY AND ENVIRONMENTAL HEALTH-PART A
fascicolo: 4, volume: 62, anno: 2001,
pagine: 281 - 288
SICI:
1528-7394(200102)62:4<281:UMIRFT>2.0.ZU;2-G
Fonte:
ISI
Lingua:
ENG
Soggetto:
APHANIZOMENON-OVALISPORUM FORTI; CULTURED RAT HEPATOCYTES; LAKE-KINNERET; ALKALOID CYLINDROSPERMOPSIN; UMEZAKIA NATANS; RACIBORSKII; ISRAEL; GLUTATHIONE; QUEENSLAND;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Agriculture,Biology & Environmental Sciences
Life Sciences
Citazioni:
17
Recensione:
Indirizzi per estratti:
Indirizzo: Sukenik, A Israel Oceanog & Limnol Res, Yigal Allon Kinneret Limnol Lab, POB 345, IL-14102 Tiberias, Israel Israel Oceanog & Limnol Res POB 345 Tiberias Israel IL-14102 l
Citazione:
R. Banker et al., "Uracil moiety is required for toxicity of the cyanobacterial hepatotoxin cylindrospermopsin", J TOX E H A, 62(4), 2001, pp. 281-288

Abstract

A new natural derivative of the sulfated guanidinium zwitterionic toxin cylindrospermopsin, 7-epi-cylindrospermopsin, was recently isolated from the cyanobacterium Aphanizomenon ovalisporum (Forti). The toxicity of the molecule (LD50 ip 5 d), estimated by mouse bioassay, was 200 mug/kg mouse, a value similar to that of cylindrospermopsin. Treatment of cylindrospermopsin with chlorine solution or chlorine-related oxidants produced two new derivatives. The chemical structure of these products was elucidated by nuclear magnetic resonance (NMR) and mass spectrometry (MS) techniques and toxicity was determined. In the first derivative, the vinylic proton at position 5 ofthe pyrimidine ring was substituted by chlorine to yield 5-chlorocylindrospermopsin. The other product is a truncated one, where C-6 of the pyrimidine ring was oxidized to a carboxylic acid. A trivial name, cylindrospermic acid, was given to this compound. Both products showed no toxic effects evenat doses 50 times higher than the LD50 of cylindrospermopsin (10 mg/kg mouse ip). Based on these results, the pyrimidine ring is postulated as the molecule component essential for the toxicity of cylindrospermopsin.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 05/04/20 alle ore 19:36:30