Department of Pharmacognosy, School of Pharmacy and ‡State Key Laboratory of Medical Neurobiology, Fudan University , 826 Zhang Heng Road, Shanghai 201203, China.
J Org Chem. 2017 Feb 3;82(3):1632-1637. doi: 10.1021/acs.joc.6b02800. Epub 2017 Jan 12.
Chemical investigation on the aerial parts of Rhododendron capitatum resulted in the discovery of five enantiomeric pairs of new meroterpenoids, (+)-/(-)-rhodonoids C (1a and 1b), E (3a and 3b), F (4a and 4b), and (-)-/(+)-rhodonoids D (2a and 2b) and G (5a and 5b). These enantiomeric pairs existed as partial racemates in a plant and were obtained by chiral HPLC separation. Their structures with absolute configurations were assigned by spectroscopic data, single-crystal X-ray diffraction, and ECD analysis. Compounds 1a and 1b are the first pair of meromonoterpenes incorporating an unprecedented 6/6/6/5 ring system, and 1a showed antiviral activity against herpes simplex virus type 1 (HSV-1) in vitro. Compounds 2a and 2b are the first examples of meromonoterpenes featuring a unique 6/6/5/5 ring system.
对绵头雪莲地上部分的化学研究导致发现了五个对映体对新的倍半萜类化合物，（+）/-（-）绵头菌素 C（1a 和 1b）、E（3a 和 3b）、F（4a 和 4b）和（-）/（+）绵头菌素 D（2a 和 2b）和 G（5a 和 5b）。这些对映体对在植物中以部分外消旋体存在，并通过手性 HPLC 分离得到。通过光谱数据、单晶 X 射线衍射和 ECD 分析确定了它们的绝对构型。化合物 1a 和 1b 是第一对包含前所未有的 6/6/6/5 环系统的单萜类化合物，化合物 1a 在体外显示出抗单纯疱疹病毒 1（HSV-1）的抗病毒活性。化合物 2a 和 2b 是具有独特 6/6/5/5 环系统的单萜类化合物的首例。
