An unusual series of thiomethylated canthin-6-ones from the North American mushroom Boletus curtisii

被引：20

作者：

Bröckelmann, MG

Dasenbrock, J

Steffan, B

Steglich, W

Wang, YK

Raabe, G

Fleischhauer, A

机构：

[1] Univ Munich, Dept Chem, D-81377 Munich, Germany

[2] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 23期

关键词：

natural products; canthin-6-ones; indole alkaloids; chiral sulfoxides; quantum chemical calculations;

D O I：

10.1002/ejoc.20040519

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A unique set of thiomethylated canthin-6-one derivatives was isolated from Boletus curtisii. The bright yellow color of this mushroom is caused by two optically active canthin-6-one sulfoxides for which the names curtisin and 9-deoxycurtisin are proposed. The structures of the new compounds were established by MS and NMR methods and the absolute configuration of the sulfoxides determined by quantum chemical calculations. This is the first occurrence of canthin-6-one alkaloids outside of higher plants. The chemotaxonomic implications of these findings are discussed. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

引用

页码：4856 / 4863

页数：8

共 22 条

[1]

AHLRICHS R, 2004, TURBOMOLE VERSION 5

[2] STUDIES ON AILANTHUS-ALTISSIMA CELL-SUSPENSION CULTURES - PRECURSOR FEEDING OF [METHYLENE-C-14]L-TRYPTOPHAN AND L-TRYPTOPHAN [J].