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来自萨赫德丹参根部的新型重排枞酸型二萜类化合物。

Novel rearranged abietane diterpenoids from the roots of Salvia sahendica.

作者信息

Jassbi Amir Reza, Mehrdad Morteza, Eghtesadi Farrokh, Ebrahimi Samad Nejad, Baldwin Ian T

机构信息

Department of Molecular Ecology, Max Planck Institute for Chemical Ecology, Hans-Knöll-Strasse 8, D-07745 Jena.

出版信息

Chem Biodivers. 2006 Aug;3(8):916-22. doi: 10.1002/cbdv.200690093.

Abstract

Two naphthoquinone diterpenoids, 1 and 2, one tricyclic, and one tetracyclic rearranged abietane ('4,5-seco-10,5-friedo-abietane') diterpenoids, 3 and 4, respectively, together with horminone (5) have been isolated from the roots of Salvia sahendica. Compounds 2 and 3 are new, and the 13C-NMR assignment for compound 4 was modified using ' Heteronuclear Multiple-Bond Correlation' (HMBC) spectroscopic data. The structures of the compounds have been established by using different spectral data including 1D- and 2D-NMR, IR, UV, and MS. The elemental composition for the major peaks of 3 and 4 were determined by ' High-Resolution Electron Impact Mass Spectrometry' (HR-EI-MS). The relative configurations of the new compounds were determined by 1H-NMR and 'Rotating-Frame NOES' (ROESY) spectroscopy. Compounds 1, 2, and 5 showed antifungal activities when tested on Blakeslea trispora. Lapachol, a prelynated naphthoquinone, was used as a positive control. The biological activities of the related naphthoquinones and abietane diterpenoids were discussed.

摘要

从伊朗丹参(Salvia sahendica)的根部已分离出两种萘醌二萜类化合物1和2、一种三环和一种四环重排的枞酸型二萜类化合物3和4,以及荷米酮(5)。化合物2和3是新化合物,并且使用“异核多键相关”(HMBC)光谱数据对化合物4的13C-NMR归属进行了修正。这些化合物的结构已通过使用包括一维和二维NMR、IR、UV和MS在内的不同光谱数据得以确定。通过“高分辨电子轰击质谱”(HR-EI-MS)确定了化合物3和4主要峰的元素组成。新化合物的相对构型通过1H-NMR和“旋转坐标系NOESY”(ROESY)光谱确定。当在三孢布拉氏霉(Blakeslea trispora)上进行测试时,化合物1、2和5表现出抗真菌活性。拉帕醇,一种预萘醌化的萘醌,用作阳性对照。讨论了相关萘醌和枞酸型二萜类化合物的生物活性。

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