来自短密青霉的新型生物活性短叶螺二萜类化合物。

Novel bioactive breviane spiroditerpenoids from Penicillium brevicompactum Dierckx.

作者信息

Macías F A, Varela R M, Simonet A M, Cutler H G, Cutler S J, Dugan F M, Hill R A

机构信息

Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Apdo. 40, 11510-Puerto Real, Cádiz, Spain.

出版信息

J Org Chem. 2000 Dec 29;65(26):9039-46. doi: 10.1021/jo0011078.

DOI:10.1021/jo0011078

PMID:11149849

Abstract

The structures of four new, naturally occurring bioactive spiroditerpenoids, (+)-breviones B, C, D, and E, potential allelopathic agents, have been determined from extracts of semisolid fermented Penicillium brevicompactum Dierckx. The structures display the novel breviane spiroditerpenoid skeleton. Structure elucidation was performed by chemical transformations and by homo- and heteronuclear 2D-NMR spectral data. On the basis of combined studies of the theoretical conformations and NOEDIFF data, their relative stereochemistry is proposed. A mixed biogenesis for this novel family of spiroditerpenoids is tendered. The levels of activity shown by breviones B, C, and E in the etiolated wheat coleoptiles bioassay, especially breviones E (100% inhibition) and C (80% inhibition) both at 10(-4) M, suggest them as lead compounds for new agrochemicals.

摘要

从短密青霉（Penicillium brevicompactum Dierckx）半固体发酵提取物中确定了四种新的天然存在的具有生物活性的螺二萜类化合物，即（+）-短密青霉素B、C、D和E，它们可能是化感物质。这些化合物的结构呈现出新颖的短密青霉螺二萜骨架。通过化学转化以及同核和异核二维核磁共振光谱数据进行结构解析。基于理论构象和NOEDIFF数据的综合研究，提出了它们的相对立体化学。对于这个新的螺二萜类化合物家族，提出了一种混合生源合成途径。短密青霉素B、C和E在黄化小麦胚芽鞘生物测定中所显示的活性水平，特别是在10⁻⁴ M时短密青霉素E（100%抑制）和C（80%抑制），表明它们可作为新型农用化学品的先导化合物。