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Titolo:
Chlorinated alkaloids in Menispermum dauricum DC. Root culture
Autore:
Sugimoto, Y; Babiker, HAA; Saisho, T; Furumoto, T; Inanaga, S; Kato, M;
Indirizzi:
Tottori Univ, Arid Land Res Ctr, Tottori 6800001, Japan Tottori Univ Tottori Japan 6800001 Land Res Ctr, Tottori 6800001, Japan Nara Womens Univ, Grad Sch Human Culture, Div Mat Sci, Nara 6308506, JapanNara Womens Univ Nara Japan 6308506 re, Div Mat Sci, Nara 6308506, Japan
Titolo Testata:
JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 10, volume: 66, anno: 2001,
pagine: 3299 - 3302
SICI:
0022-3263(20010518)66:10<3299:CAIMDD>2.0.ZU;2-O
Fonte:
ISI
Lingua:
ENG
Soggetto:
ACUTUMINE; DECHLOROACUTUMINE; BIOSYNTHESIS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
16
Recensione:
Indirizzi per estratti:
Indirizzo: Sugimoto, Y Tottori Univ, Arid Land Res Ctr, 1390 Hamasaka, Tottori 6800001, Japan Tottori Univ 1390 Hamasaka Tottori Japan 6800001 00001, Japan
Citazione:
Y. Sugimoto et al., "Chlorinated alkaloids in Menispermum dauricum DC. Root culture", J ORG CHEM, 66(10), 2001, pp. 3299-3302

Abstract

Feeding experiments using Cl-36 showed that Melzispermum,dauricum root culture produces four alkaloids containing chlorine. They included the novel alkaloids dauricumine and dauricumidine as well as the known alkaloids acutumine and acutumidine. The structures of novel alkaloids were established byspectroscopic, crystallographic, and chemical methods. These four alkaloids were labeled with Cl-36, isolated, and fed independently to root cultures. Mutual conversion between acutumine and acutumidine, and between dauricumine and dauricumidine by N-methylation and N-demethylation, was demonstrated. Moreover, dauricumine was converted to acutumine and acutumidine. Epimerization of acutumidine to dauricumidine or vice versa was not observed. These results suggest that dauricumine is the first chlorinated alkaloid formed in cultured M. dauricum roots. Skewed distribution of radioactivity derived from labeled dauricumine is proof that epimerization at C-l proceeds at a lower rate than N-demethylation.

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Documento generato il 22/10/20 alle ore 08:50:07