HIV-inhibitory cembrane derivatives from a Philippines collection of the soft coral Lobophytum species
HIV-inhibitory cembrane derivatives from a Philippines collection of the soft coral Lobophytum species
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DOI：
10.1021/np990372p
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发表时间：
2000-04-01
影响因子：
5.1
通讯作者：
Boyd, MR
中科院分区：
文献类型：
--
作者：
Rashid, MA;Gustafson, KR;Boyd, MR
生物测定指导分馏的菲律宾群岛收集的软珊瑚Lobophytum物种的水提取物，浓缩其HIV抑制活性到馏分中富含西松烷二萜。从这些组分中通过HPLC纯化了lobohedlexide（1），（7Z）-lobohedlexide（2）和一个新化合物17-dimethylaminobohedlexide（3）。化合物1-3的结构通过光谱分析和与文献报道的光谱数据的比较进行了鉴定。通过一维NOESY实验确定了3的γ-内酯环取代基的相对立体化学。虽然已经从软珊瑚Sinularia sp.中报道了几种含有二甲基氨基官能团的其他西松烷类化合物，化合物3代表第一个从Lobophytum物种中分离的具有该官能团的西松膜二萜。在基于细胞的体外抗HIV测定中，二萜类化合物1-3表现出中等的HIV抑制活性（EC 50约3-5 μ g/mL）。
Bioassay-guided fractionation of an aqueous extract of a Philippine Islands collection of the soft coral Lobophytum sp, concentrated its HIV-inhibitory activity into fractions rich in cembranoid diterpenes. Lobohedleolide (1), (7Z)-lobohedleolide (2), and a new compound, 17-dimethylaminolobohedleolide (3), were purified from these fractions by HPLC. The structures of compounds 1-3 were elucidated by spectroscopic analyses and by comparison of their spectral data with previously reported values. The relative stereochemistry of the gamma-lactone ring substituents of 3 was determined by 1D NOESY experiments. While several other cembranoids that contain a dimethylamino functional group have been reported from the soft coral Sinularia sp., compound 3 represents the first cembrane diterpene with this functional group isolated from a Lobophytum species. Diterpenoids 1-3 exhibited moderate HIV-inhibitory activity (EC50 approximately 3-5 mu g/mL) in a cell-based in vitro anti-HIV assay.