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从苦梓树(D. Don)Benn.的叶子中分离得到 C、C 和 C 型土沉香三萜类化合物的结构阐明和绝对构型确定

Structure elucidation and absolute configuration determination of C, C and C tirucallane triterpenoids from the leaves of Picrasma quassioides (D. Don) Benn.

机构信息

Key Laboratory of Computational Chemistry Based Natural Antitumor Drug Research & Development, Liaoning Province, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, 110016, China.

School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang, 110016, China.

出版信息

Phytochemistry. 2021 Apr;184:112675. doi: 10.1016/j.phytochem.2021.112675. Epub 2021 Feb 4.

Abstract

Seven undescribed tirucallane-type triterpenoids, kumunorquassins A‒E and kumuquassins K and L, along with nine known analogues, have been isolated from the leaves of Picrasma quassioides (D. Don) Benn. Their structures and absolute configurations were elucidated based on comprehensive spectroscopic analyses, single-crystal X-ray diffraction analysis and electronic circular dichroism (ECD). The absolute configuration of cornusalterin J was unequivocally determined by X-ray diffraction based on its p-bromobenzoate derivative. A brief approach was presented in our study, which could rapidly and conveniently determine the relative and absolute configurations of OCH-23 of kumuquassin L and cornusalterins J, H and G depending on the chemical shift differences (Δδ) of C-24 and C-25 and the chemical shifts of C-23, H-23 and H-24. In addition, the cytotoxicities of these compounds against two human tumour cell lines (HepG2 and Hep3B) were evaluated.

摘要

从苦槛蓝(Picrasma quassioides(D. Don)Benn.)的叶子中分离得到了 7 个未描述的三萜类化合物,即 kumunorquassins A-E 和 kumuquassins K 和 L,以及 9 个已知类似物。基于综合光谱分析、单晶 X 射线衍射分析和电子圆二色性(ECD),确定了它们的结构和绝对构型。通过 X 射线衍射,基于其对溴苯甲酸酯衍生物,Cornusalterin J 的绝对构型得到了明确的确定。在我们的研究中提出了一种简单的方法,可以根据 C-24 和 C-25 的化学位移差异(Δδ)以及 C-23、H-23 和 H-24 的化学位移,快速方便地确定 kumuquassin L 和 Cornusalterins J、H 和 G 的 OCH-23 的相对和绝对构型。此外,还评估了这些化合物对两种人肿瘤细胞系(HepG2 和 Hep3B)的细胞毒性。

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