The new cembrane diterpene (3E,11E)-cembra-3,8(19),11,15-tetraene-7alpha-ol (1), nephthenol (2), and all-trans-peridinin (3) have been isolated from the soft coral Litophyton arboreum. The tetraterpene 3, (+)-7,8-epoxy-7,8-dihydrocembrene C (4), emblide (5), sarcophytoxide (6), sarcoglaucol-16-one (7), guajacophine (8), and 1,4-peroxymuurol-5-ene (9) have been obtained from the soft coral Sarcophyton ehrenbergi. The compounds were characterized primarily by NMR spectroscopy. Some of the terpenes were tested for their antiproliferative activity against the cell lines HUVEC and K-562 and for cytotoxicity against the cell line HeLa, and they showed moderate activities.
Abstract9-Hydroxy-10,11-dehydro-sarcotrocheliol (1), a new pyrane-based cembranoid diterpene, has been isolated along with three other known compounds, namely, sarcotrocheliol acetate (2), (+)-sarcophytol A (3), and (−)-sarcophytonin A (4), from the organic extract of the soft coral Sarcophyton trocheliophorum. The chemical structures of compounds 1–4 were determined on the basis of their 1D and 2D NMR [1H, 13C, 1H–1H correlation spectroscopy, heteronuclear multiple-quantum coherence, heteronuclear multiple-bond correlation, and nuclear Overhauser effect (NOE)] and mass spectra [electron ionization (EI), electrospray ionization, and high resolution mass spectrometry (HRMS)], and by comparison with related structures. The compounds 1–4 showed neither antimicrobial activity against 11 diverse tested microorganisms, nor cytotoxicity against brine shrimp, whereas the soft coral extract showed low cytotoxicity with a mortality rate of 1.7%.
During our continual searching programme for novel bioactive metabolites from Sarcophyton trocheliophorum, collected from Red Sea, we describe herein the isolation and structural elucidation of further two new pyrane-based cembranoid diterpenes: 9-hydroxy-7,8-dehydro-sarcotrocheliol (1) and 8,9-expoy-sarcotrocheliol acetate (2), along with the well-known sarcotrocheliol acetate (3), (+)-sarcophine (4), (+)-sarcophytoxide (5) and (-)-sarcophytoxide (6). The chemical structures of compounds 1 and 2 were determined on the basis of 1D and 2D NMR (H, C,H-H COSY, HMQC, HMBC and NOE), mass spectra (ESI and HR-ESIMS) and by comparison with related structures. The antimicrobial activities of the reported compounds 1-6 were investigated. According to the molecular docking study of compounds 1-6 using 3D structure of α,β tubulin in complex with taxol (PDB code 1JFF) and epothilone A (PDB code 1TVK), sarcophine (4) displayed the highest affinity towards both crystal structures, followed by 5 and 6, meanwhile pyrane-based cembranoid diterpenes (1-3) showed less affinity.
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