狼毒甾体类化合物A - F，源自瑞香科植物狼毒（Stellera chamaejasme L.）根部的具有抗HIV活性的大环瑞香烷原酸酯

Stelleratenoids A-F, macrocyclic daphnane orthoesters with anti-HIV activity from the roots of Stellera chamaejasme L.

作者信息

Ding Kang, Wu Zi-Yao, Zhang Nuan, He Jun, Zhang Fan, Wu Jing-Jing, Bai Hong-Jin, Zhang Wei-Ku, Li Lin, Xu Jie-Kun

机构信息

School of Life Sciences & School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029, People's Republic of China; Institute of Clinical Medical Sciences & Department of Pharmacy, China-Japan Friendship Hospital, Beijing, 100029, People's Republic of China.

NMPA Key Laboratory for Research and Evaluation of Drug Metabolism, Guangdong Provincial Key Laboratory of New Drug Screening, School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515, People's Republic of China.

出版信息

Phytochemistry. 2023 Jun;210:113648. doi: 10.1016/j.phytochem.2023.113648. Epub 2023 Mar 22.

DOI:10.1016/j.phytochem.2023.113648

PMID:36963707

Abstract

Six undescribed macrocyclic daphnane orthoesters, stelleratenoids A-F (1-6), were isolated from the roots of Stellera chamaejasme L. Their structures were elucidated by extensive spectroscopic analyses, including HRESIMS and NMR spectra. Compound 1 features an unusual terminal double bond at C-2/C-19 in the 1α-alkyldaphnane lactone skeleton. Compounds 2-4 are unique in the presence of different long chain fatty acyl groups. Compounds 5 and 6 are unique examples of modified macrocyclic daphnane diterpenoids. All the isolates were evaluated for anti-HIV activity in MT-2 cells. Among them, compounds 1, 5 and 6 exhibited highly potent anti-HIV activity with EC values of 66.70, 10.62 and 55.10 nM, respectively, possessing high potential to develop new anti-HIV drugs.

摘要

从瑞香狼毒（Stellera chamaejasme L.）的根部分离出6个未描述的大环瑞香烷原酸酯，即狼毒萜类化合物A - F（1 - 6）。通过广泛的光谱分析，包括高分辨电喷雾电离质谱（HRESIMS）和核磁共振（NMR）光谱对其结构进行了阐明。化合物1在1α - 烷基瑞香烷内酯骨架的C - 2/C - 19处具有不寻常的末端双键。化合物2 - 4的独特之处在于存在不同的长链脂肪酰基。化合物5和6是修饰的大环瑞香烷二萜类化合物的独特实例。所有分离物均在MT - 2细胞中评估了抗HIV活性。其中，化合物1、5和6表现出高效的抗HIV活性，其半数有效浓度（EC）值分别为66.70、10.62和55.10 nM，具有开发新型抗HIV药物的高潜力。