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. 2018 Oct;8(6):944-955.
doi: 10.1016/j.apsb.2018.06.004. Epub 2018 Jun 19.

Cembrane-type diterpenoids from the South China Sea soft coral Sarcophyton mililatensis

Songwei Li  1   2 , Fei Ye  1 , Zhengdan Zhu  1 , Hui Huang  3 , Shuichun Mao  2 , Yuewei Guo  1
Affiliations

Cembrane-type diterpenoids from the South China Sea soft coral Sarcophyton mililatensis

Songwei Li et al. Acta Pharm Sin B. 2018 Oct.

Abstract

Eight cembrane-type diterpenoids, namely, (+)-(6R)-6-hydroxyisosarcophytoxide (1), (+)-(6R)-6-acetoxyisosarcophytoxide (2), (+)-17-hydroxyisosarcophytoxide (3), sarcomililatins A-D (4-7), and sarcomililatol (8), were isolated from the soft coral Sarcophyton mililatensis collected from Weizhou Island, Guangxi Autonomous Region, together with 2 known related analogues, (+)-isosarcophytoxide (9) and (+)-isosarcophine (10). The structures of these compounds were elucidated by a combination of detailed spectroscopic analyses, chemical methods, and comparison with reported data. The absolute configuration of compound 1 was established by the modified Mosher׳s method, while the absolute configurations of compounds 4 and 5 were assigned by electronic circular dichroism (ECD) spectroscopy and that of compound 8 was established by time-dependent density functional theory electronic circular dichroism (TD-DFT ECD) calculation. In in vitro bioassays, compound 9 displayed significant cytotoxicity against the human cancer cell lines human promyelocytic leukemia cells (HL-60) and human lung adenocarcinoma cells (A-549) with IC50 values of 0.78±0.21 and 1.26±0.80 μmol/L, respectively. Compounds 4 and 9 also showed moderate inhibitory effects on the TNFα-induced Nuclear factor kappa B (NF-κB, a therapeutical target in cancer) activation, showing IC50 values of 35.23±12.42 and 22.52±4.44 μmol/L, respectively.

Keywords: Cembrane-type diterpe-noids; Cytotoxicity; ECD calculation; Modified Mosher׳s method; NF-κB inhibitory activity; Sarcophyton; Sarcophyton mililatensis; Soft coral.

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Figures

fx1
Graphical abstract
Figure 1
Figure 1
Chemical structures of compounds 1–10.
Figure 2
Figure 2
Selected 1H–1H COSY and HMBC correlations of 1, 4, 6, and 8.
Figure 3
Figure 3
Key NOESY correlations for compounds 1, 4, 6, and 8.
Figure 4
Figure 4
∆δH values [∆δ (in ppm) = δS–δR] obtained for (S)- and (R)-MTPA esters of compound 1 in pyridine-d5.
Figure 5
Figure 5
ECD spectra for compounds 4 (0.0014 mol/L, CH3CN, cell length 2 cm) and 5 (0.0014 mol/L, CH3CN, cell length 2 cm).
Figure 6
Figure 6
Experimental ECD spectrum of 8 [0.0016 mol/L, CH3CN, cell length 2 cm] (black) compared with the calculated ECD spectra of 8 (red) and its enantiomer (blue).
Scheme 1
Scheme 1
Putative biosynthetic pathways toward the formation of compounds 4–6.
See this image and copyright information in PMC

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