Structure revision and cytotoxic activity of the scabrosin esters, epidithiopiperazinediones from the lichen Xanthoparmelia scabrosa

被引：41

作者：

Ernst-Russell, MA ^{[1
]}

Chai, CLL

Hurne, AM

Waring, P

Hockless, DCR

Elix, JA

机构：

[1] Australian Natl Univ, The Faculties, Dept Chem, Canberra, ACT 0200, Australia

[2] Australian Natl Univ, Inst Adv Studies, John Curtin Sch Med Res, Canberra, ACT 0200, Australia

[3] Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1999年 / 52卷 / 04期

基金：

澳大利亚研究理事会;

关键词：

D O I：

10.1071/C99019

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The scabrosin esters (1)-(4), isolated from the lichen Xanthoparmelia scabrosa, were reanalysed by modern one- and two-dimensional n.m.r. spectroscopic methods, including N-15 n.m.r. spectroscopy, and single-crystal X-ray structural analysis. This reinvestigation has resulted in the unambiguous structure elucidation and complete spectral assignment of these metabolites and established them to be a family of epidithiopiperazinedione derivatives. A new scabrosin ester, scabrosin butyrate hexanoate (5), has also been isolated and its structure determined, including assignment of absolute configuration. Several scabrosins were found to exhibit potent cytotoxic activity against the murine P815 mastocytomia cell line (IC50 c. 0.5 mu M) and the human breast MCF7 carcinoma cell line (IC50 c. 1 nM). Compounds which contain a dithiopiperazinedione moiety have not previously been identified in lichenized fungi.

引用

页码：279 / 283

页数：5

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