唇形科鞘蕊花中的具有抗炎和抗增殖作用的二萜类化合物。

Anti-inflammatory and antiproliferative diterpenoids from Plectranthus scutellarioides.

机构信息

School of Pharmaceutical Sciences, University of Geneva, University of Lausanne, Rue Michel-Servet 1, 1211 Geneva 4, Switzerland.

C-TAC, UMR 8638 CNRS, Université Paris Descartes, Sorbonne Paris Cité, Faculté de Pharmacie de Paris, Avenue de l'Observatoire 4, 75006 Paris, France.

出版信息

Phytochemistry. 2018 Oct;154:39-46. doi: 10.1016/j.phytochem.2018.06.012. Epub 2018 Jun 28.

DOI:10.1016/j.phytochem.2018.06.012

PMID:29960256

Abstract

Chemical investigation of the dichloromethane extract of the aerial parts of Plectranthus scutellarioides led to the isolation and characterization of 10 diterpenoids with an abietane skeleton and one cembrane-type diterpenoid. Among them, six have not yet been described in the literature. Their structures were established by 1D and 2D NMR, UV and IR spectroscopy, and HRESIMS. The relative configuration was determined by Gauge-Independent Atomic Orbital NMR chemical shift calculations supported by the advanced statistical method DP4 plus and further confirmed by electronic circular dichroism. The isolated constituents were evaluated for their in vitro NF-κB inhibitory activity, as well as for their cytotoxic effects in human multiple myeloma cancer stem cells and RPMI 8226 tumor cell line. Coleon O, coleon G, lanugone K and 6-acetylfredericone B showed the highest inhibitory effect against NF-κB, displaying IC of 11.2, 11.0, 4.5 and 9.7 μM, respectively. Coleon O exhibited also a significant activity towards human multiple myeloma cancer stem cells and RPMI 8226 cells with IC of 9.2 and 8.4 μM, respectively.

摘要

从假荆芥（Plectranthus scutellarioides）地上部分的二氯甲烷提取物中进行化学研究，分离并鉴定出 10 个具有扁柏烷骨架的二萜和 1 个柏烷型二萜。其中，有 6 个尚未在文献中描述。通过 1D 和 2D NMR、UV 和 IR 光谱以及 HRESIMS 确定了它们的结构。通过 Gauge-Independent Atomic Orbital NMR 化学位移计算确定相对构型，并通过先进的统计方法 DP4 plus 进行支持，进一步通过电子圆二色性证实。对分离得到的成分进行了体外 NF-κB 抑制活性以及对人多发性骨髓瘤肿瘤干细胞和 RPMI 8226 肿瘤细胞系的细胞毒性作用评估。Coleon O、coleon G、lanugone K 和 6-acetylfredericone B 对 NF-κB 的抑制作用最强，IC 分别为 11.2、11.0、4.5 和 9.7 μM。Coleon O 对人多发性骨髓瘤肿瘤干细胞和 RPMI 8226 细胞也表现出显著的活性，IC 分别为 9.2 和 8.4 μM。