Cytotoxic Nitrogenous Terpenoids from Two South China Sea Nudibranchs Phyllidiella pustulosa, Phyllidia coelestis, and Their Sponge-Prey Acanthella cavernosa
Qihao Wu,
Wen-Ting Chen,
Song-Wei Li,
Jian-Yu Ye,
Xia-Juan Huan,
Margherita Gavagnin,
Li-Gong Yao,
Hong Wang,
Ze-Hong Miao,
Xu-Wen Li,
Yue-Wei Guo
Affiliations
Qihao Wu
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zuchongzhi Road 555 Zhangjiang Hi-Tech Park, Shanghai 201203, China
Wen-Ting Chen
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zuchongzhi Road 555 Zhangjiang Hi-Tech Park, Shanghai 201203, China
Song-Wei Li
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zuchongzhi Road 555 Zhangjiang Hi-Tech Park, Shanghai 201203, China
Jian-Yu Ye
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zuchongzhi Road 555 Zhangjiang Hi-Tech Park, Shanghai 201203, China
Xia-Juan Huan
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zuchongzhi Road 555 Zhangjiang Hi-Tech Park, Shanghai 201203, China
Margherita Gavagnin
Consiglio Nazionale delle Ricerche (CNR), Istituto di Chimica Biomolecolare (ICB), Via Campi Flegrei, 34, 80078 Pozzuoli (Na), Italy
Li-Gong Yao
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zuchongzhi Road 555 Zhangjiang Hi-Tech Park, Shanghai 201203, China
Hong Wang
College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, China
Ze-Hong Miao
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zuchongzhi Road 555 Zhangjiang Hi-Tech Park, Shanghai 201203, China
Xu-Wen Li
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zuchongzhi Road 555 Zhangjiang Hi-Tech Park, Shanghai 201203, China
Yue-Wei Guo
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zuchongzhi Road 555 Zhangjiang Hi-Tech Park, Shanghai 201203, China
A detailed chemical investigation of two South China Sea nudibranchs Phyllidiella pustulosa and Phyllidia coelestis, as well as their possible sponge-prey Acanthella cavernosa, led to the isolation of one new nitrogenous cadinane-type sesquiterpenoid xidaoisocyanate A (1), one new naturally occurring nitrogen-containing kalihinane-type diterpenoid bisformamidokalihinol A (16), along with 17 known nitrogenous terpenoids (2–15, 17–19). The structures of all the isolates were elucidated by detailed spectroscopic analysis and by the comparison of their spectroscopic data with those reported in the literature. In addition, the absolute stereochemistry of the previously reported axiriabiline A (5) was determined by X-ray diffraction (XRD) analysis. In a bioassay, the bisabolane-type sesquiterpenoids 8, 10, and 11 exhibited cytotoxicity against several human cancer cell lines.
