Polyhydroxylated steroids from the Vietnamese starfish Luidia maculata.

Applying various chromatographic separations, six polyhydroxylated steroids including four new ones, maculasteroids A-D (1-4), were isolated from the Vietnamese starfish Luidia maculata. Their structures were elucidated by detailed analysis of 1D, 2D NMR and HR QTOF mass spectra. The 3β,5,6β,7α,15α,16β-hexol 15-sulfate (1 and 2) and 2β,3β,5,6β,7α,15α,16β-heptol 15-sulfate (3) steroid cores were reported for the first time in polyhydroxylated steroids to date. In addition, the best antiproliferative activity among the isolated compounds was recorded for 5α-cholestane-3β,5,6β,7α,15α,16β,26-heptol (5) on all five cell lines SK-LU-1 (lung carcinoma), HepG2 (hepatocarcinoma), MCF7 (breast carcinoma), LNCaP (prostate carcinoma), and KB (carcinoma in the mouth) and 5α-cholestane-3β,6β,7α,15α,16β,26-hexol (6) on LNCaP and KB cell lines with IC50 values ranging from 10.40 ± 0.38 to 19.91 ± 1.22 µM.