Bioactive α,β-conjugated 3-keto-steroids from the Australian brown alga Cystophora xiphocarpa

Holland I 1 , Bakri YM 2 , Sakoff J 3 , Zaleta Pinet D 1 , Motti C 4 , van Altena I 5

Affiliations 

  • 1 Chemistry, School of Environmental and Life Sciences, Faculty of Science, The University of Newcastle, Callaghan, NSW, 2308, Australia
  • 2 Chemistry, School of Environmental and Life Sciences, Faculty of Science, The University of Newcastle, Callaghan, NSW, 2308, Australia; Department of Chemistry, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, Tanjong Malim, 35900, Perak, Malaysia
  • 3 Chemistry, School of Environmental and Life Sciences, Faculty of Science, The University of Newcastle, Callaghan, NSW, 2308, Australia; Department of Medical Oncology, Calvary Mater Newcastle Hospital, NSW, 2298, Australia
  • 4 Australian Institute of Marine Science, PMB 3, Townsville MC, 4810, QLD, Australia
  • 5 Chemistry, School of Environmental and Life Sciences, Faculty of Science, The University of Newcastle, Callaghan, NSW, 2308, Australia. Electronic address: Ian.vanAltena@newcastle.edu.au
Phytochemistry, 2021 Aug;188:112798.
PMID: 34020274 DOI: 10.1016/j.phytochem.2021.112798

Abstract

As part of our ongoing study of the specialised metabolites present in brown algae belonging to the Cystophora genus, eight new steroids including three pairs of diastereoisomers were isolated from Cystophora xiphocarpa (Harvey) (Sargassacea, Fucales). The metabolites identified by standard spectrometric methods are (16S,22S)-16,22-dihydroxyergosta-4,24(28)-dien-3-one and (16S,22R)-16,22-dihydroxyergosta-4,24(28)-dien-3-one, (16S,22S,24R)-16,22,24-trihydroxyporifera-4,28-dien-3-one and (16S,22S,24S)-16,22,24-trihydroxystigma-4,28-dien-3-one along with (16S,22S,24E)-16,22-dihydroxystigma-4,24(28)-dien-3-one and (16S,20S)-16,20-dihydroxyergosta-4,24(28)-dien-3-one. (16S,22S,24E)-16,22-Dihydroxystigma-4,24(28)-dien-3-one possessed the most potent cytotoxicity of the steroids in this series with cell growth inhibitions of GI50 8.7 ± 0.7 μM against colon cancer HT29, GI50 5.6 ± 0.8 μM against the breast cancer line MCF-7 and GI50 4.5 ± 0.2 μM against the ovarian cancer cell line A2780. (16S,22R)-16,22-dihydroxyergosta-4,24(28)-dien-3-one was found to be active against the ovarian cancer cell line A2780 with a GI50 of 6.2 ± 0.1 μM.

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