Three unusual 4-oxo-20-nor-taxanes from the cell cultures of Taxus × media

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-02-13 DOI:10.1016/j.tetlet.2025.155503

Yuxin Wang , Changkang Li , Songyang Sui, Jimei Liu, Jungui Dai

引用次数: 0

Abstract

Mediataxanes A–C (1–3), three unusual 4-oxo-20-nor-taxanes with 6/8/6 ring system were isolated from Taxus × media cell cultures. Their structures were determined by extensive spectroscopic data, and the absolute configurations were confirmed by X-ray crystallographic analysis (1 and 2) and NMR data comparison (3). Biological assay revealed that 1 exhibited moderate cytotoxicity against gastric carcinoma BGC823 and cervical cancer HeLa cells. In addition, a plausible mechanism for the oxidative cleavage of 4(20)-exocyclic-double bond and the formation of 4-carbonyl group in 1–3 is proposed.

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红豆杉x培养基细胞培养中三种不寻常的4-氧-20-不紫杉烷

Mediataxanes A-C(1-3)，从Taxus ×培养基细胞中分离到3个具有6/8/6环体系的4-氧-20-不紫杉烷。通过广泛的光谱数据确定了它们的结构，并通过x射线晶体分析（1和2）和核磁共振数据比较(3)证实了它们的绝对构型。生物实验表明，1对胃癌BGC823和宫颈癌HeLa细胞具有中等的细胞毒性。此外，还提出了4(20)-外环双键氧化裂解和1-3中4-羰基形成的可能机制。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.