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Titolo:
BIOSYNTHETIC INTERMEDIATES OF INDOLE-DITERPENOID MYCOTOXINS FROM SELECTED TRANSFORMATIONS AT C-10 OF PAXILLINE
Autore:
PENN J; MANTLE PG;
Indirizzi:
UNIV LONDON IMPERIAL COLL SCI TECHNOL & MED,DEPT BIOCHEM LONDON SW7 2AY ENGLAND UNIV LONDON IMPERIAL COLL SCI TECHNOL & MED,DEPT BIOCHEM LONDON SW7 2AY ENGLAND
Titolo Testata:
Phytochemistry
fascicolo: 4, volume: 35, anno: 1994,
pagine: 921 - 926
SICI:
0031-9422(1994)35:4<921:BIOIMF>2.0.ZU;2-N
Fonte:
ISI
Lingua:
ENG
Soggetto:
TREMORGENIC MYCO-TOXINS; PENICILLIUM-CRUSTOSUM; STRUCTURE ELUCIDATION; PENITREM-A; SUBMERGED FERMENTATION; CLAVICEPS-PASPALI; LOLITREM-B; NEUROTOXINS; METABOLITES; PRECURSORS;
Keywords:
PENICILLIUM SP; BIOSYNTHESIS; PAXILLINE; PENITREMS; JANTHITREMS; PAXITRIOLS; LOLITREMS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
25
Recensione:
Indirizzi per estratti:
Citazione:
J. Penn e P.G. Mantle, "BIOSYNTHETIC INTERMEDIATES OF INDOLE-DITERPENOID MYCOTOXINS FROM SELECTED TRANSFORMATIONS AT C-10 OF PAXILLINE", Phytochemistry, 35(4), 1994, pp. 921-926

Abstract

The products of NaBH4 reduction of the 10-keto group of paxilline, biosynthetically radiolabelled with C-14 in the diterpenoid moiety, resolved into alpha and beta isomers, were fed to submerged fermentations of Penicillium janczewskii and P. janthinellum producing penitrem and janthitrem alkaloids, respectively. Incorporation into the alkaloids was compared with that of [C-14]paxilline, 13.7 and 23.2% of which was found in penitrems and janthitrems, respectively. 10beta-Hydroxy[C-14]paxilline (beta-paxitriol) was incorporated 10.7% into penitrems and 34.5% into janthitrems, providing compelling evidence that both paxilline and its 10beta-hydroxy derivative are intermediates in the biosynthesis of these aromatic-substituted indole-diterpenoids. Low (approximately 1%) incorporation values for 10alpha-hydroxy[C-14]paxilline (alpha-paxitriol) indicated that this isomer is not an intermediate but that the fungi, particularly P. janthinellum, may possess some isomerase activity. 10beta-O-Acetyl[C-14]paxilline was incorporated (4.5%) into janthitrems B and C, probably via deacetylation to beta-[C-14]paxitriol. 10alpha-O-Acetyl[C-14]paxilline was not significantly incorporated.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 02/07/20 alle ore 22:36:54