Title
Uncommon nornardosinane, seconeolemnane and related sesquiterpenoids from Xisha soft coral Litophyton nigrum
Year
2020
Journal
Bioorganic Chemistry
Abstract
Three new nardosinane-type sesquiterpenoids linardosinenes A–C (1–3) and four new neolemnane-type sesquiterpenoids lineolemnenes A–D (4–7), together with the related known compound 4-acetoxy-2,8-neolemnadien-5-one (8), were isolated from the Xisha soft coral Litophyton nigrum. The structures of these new compounds were elucidated by comprehensive analyses of spectroscopic data, in association with modified Mosher's method and ECD calculations for configurational assignments and the absolute configuration of 8 was determined by X-ray diffraction analysis for the first time. Structurally uncommon nornardosinane and seconeolemnane skeletons for compounds 1 and 7, respectively, are rare carbon frameworks in naturally occurring sesquiterpenoids. The absolute configurations of 1, 7, and 8 were determined by modified Mosher's method, TDDFT ECD approach, and X-ray diffraction analysis, respectively. This is the first chemical study of L. nigrum and the first report of nornardosinane, seconeolemnane and related sesquiterpenoids from the genus Litophyton. The isolates 1–7 were evaluated for their cytotoxicity against THP-1, SNU-398, HT-29, Capan-1 and A549 cell lines and inhibitory activities against PTP1B, BRD4, HDAC1 and HDAC6 protein kinases. The results indicated that compounds 2–5 inhibited proliferation of human cancer cells. However, none of them were potent inhibitors of protein kinases.
Instrument
J-810
Keywords
Circular dichroism, Absolute configuration, Biochemistry, Pharmaceutical