title: Sesterterpenoids Isolated from the Sponge Phorbas sp. Activate Latent HIV-1 Provirus Expression.
abstract: Eight new sesterterpenoids, alotaketals D (8) and E (9), ansellones D (10), E (11), F (12), and G (13), and anvilones A (14) and B (15), have been isolated from extracts of the marine sponge Phorbas sp. collected in Howe Sound British Columbia, and their structures have been elucidated by analysis of NMR and MS data. Ansellone F (12) contains a rare 1,2-3,4-bis-epoxydecalin substructure. Anvilones A (14) and B (15) have an unprecedented tetracylic anvilane terpenoid carbon skeleton. Using a cell culture model of latent HIV-1 infection, ansellone A (3), alotaketal D (8), and anvilone A (14) were found to induce HIV proviral gene expression similar to the control compound prostratin (1), while the known sesterterpenoid alotaketal C (2), isolated from the same extract, was more potent and gave a stronger response than prostratin (1). Like prostratin (1), all of the Phorbas sesterterpenoids with latency reversal agent properties appear to activate protein kinase C signaling.
authors: Departments of Chemistry and Earth, Oceans & Atmospheric Sciences, University of British Columbia , 2036 Main Mall, Vancouver, British Columbia, Canada V6T 1Z1.
authors: Meng
authors: M
authors: Wang
authors: Faculty of Health Sciences, Simon Fraser University , Burnaby, British Columbia, Canada V5A 1S6.
authors: Ian
authors: I
authors: Tietjen
authors: Departments of Chemistry and Earth, Oceans & Atmospheric Sciences, University of British Columbia , 2036 Main Mall, Vancouver, British Columbia, Canada V6T 1Z1.
authors: Min
authors: M
authors: Chen
authors: Departments of Chemistry and Earth, Oceans & Atmospheric Sciences, University of British Columbia , 2036 Main Mall, Vancouver, British Columbia, Canada V6T 1Z1.
authors: David E
authors: DE
authors: Williams
authors: Departments of Chemistry and Earth, Oceans & Atmospheric Sciences, University of British Columbia , 2036 Main Mall, Vancouver, British Columbia, Canada V6T 1Z1.
authors: Julie
authors: J
authors: Daoust
authors: Faculty of Health Sciences, Simon Fraser University , Burnaby, British Columbia, Canada V5A 1S6.|British Columbia Centre for Excellence in HIV/AIDS, St. Paul's Hospital , Vancouver, British Columbia, Canada V6Z 1Y6.|Department of Molecular Biology and Biochemistry, Simon Fraser University , Burnaby, British Columbia, Canada V5A 1S6.
authors: Mark A
authors: MA
authors: Brockman
authors: Departments of Chemistry and Earth, Oceans & Atmospheric Sciences, University of British Columbia , 2036 Main Mall, Vancouver, British Columbia, Canada V6T 1Z1.
authors: Raymond J
authors: RJ
authors: Andersen
mesh_terms: D000818:Animals; D015496:CD4-Positive T-Lymphocytes / Q000821:virology; D002460:Cell Line; D015497:HIV-1 / Q000187:drug effects* / Q000502:physiology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D011533:Proviruses / Q000187:drug effects* / Q000502:physiology; D054830:Sesterterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D021241:Spectrometry, Mass, Electrospray Ionization; D013056:Spectrophotometry, Ultraviolet; D014775:Virus Activation / Q000187:drug effects*; D017735:Virus Latency
chemical_list: D054830:Sesterterpenes